At HIS Expense! Written by Max Swan (133 pages) (Patreon)

At His Expense!

Written by Max Swan

Concept by Devin Dickie

© 2019-2030 QoS Comix All Rights Reserved
No part of this publication may be reproduced, distributed or transmitted in any form or by any means, including photocopying, recording, or other electronic or mechanical methods, without the prior written permission of the publisher, except in the case of brief quotations embodied in critical reviews and certain other noncommercial uses permitted by copyright law. For permission requests, email to Devinwhitegurl@gmail.com

This is a work of fiction. Names, characters, places, and incidents are a product of the author’s imagination. Locales and public names are sometimes used for atmospheric purposes. Any resemblance to actual people, living or dead, or to businesses, companies, events, institutions, or locales is completely coincidental.

***DEVIN DICKIE NOTE***
All characters are OVER 18 years of AGE! This is a bullying fantasy and not real. The acts in the following written work are only consensual sexual choices and fantasy humiliation scenarios. Bullying is NOT OKAY and If you or someone you

know is being bullied, please alert the authorities.

At His Expense!

Written by Max Swan Concept by Devin Dickie

Contents:

Chapter 1 Chapter 2 Chapter 3 Chapter 4 Chapter 5 Epilogue

Chapter 1

After moving to New York from Denver, paralegal Deborah Hewson’s life was complicated. She left behind a man she felt very attracted to, a black man who was also very well hung. They kept the long-distance thing going for a while, but it became clear to Deborah that her beau back in Denver wasn’t being faithful. She felt upset about it, but she knew that it would be impossible for someone like Garth to stay celibate for her. The man was a sex machine, and he’d naturally be sniffing around for some hot woman to fuck now Deborah was gone. She resented it but, deep down, accepted that it was inevitable. As she soon learns, men like Garth cannot be controlled from a

distance. Controlling men, especially lovers, is something Deborah excels at. She likes to make them think they’re the boss, but she knows how to manipulate a man’s ego like the best.

For this reason, she was head-hunted to a law firm in New York with double pay and a condo in Manhattan. Her new boss, a black woman, called Nancy King from the law firm: ‘Goldman, King, and Peters,’ spotted her talents when consulting on a criminal case in Denver. Nancy saw how Deborah somehow got the man accused of embezzling fifty million dollars from a high-profile corporation to hand over all the information they needed in the case. The man was reluctant to cooperate with his defense team because he worried he might further incriminate himself.

However, Deborah convinced the man to hand over everything he had, which impressed everyone.

Her preference for well-hung black men was something she discovered was in abundance in New York City. Deborah is a busty curvy woman around five foot five, with brown hair, blue eyes, and porcelain-like white skin. She’s beautiful. But finding a man still proves a somewhat

elusive prospect for her. Take her latest attempt to find a black boyfriend in New York. On Tinder, she met Calvin, or ‘Cal’ as he preferred to be called, and they dated for a while. Until the faithful evening when things went sour for Deborah.

*****

They returned to Deborah’s condo after a night of dancing and drinking at a nightclub. Calvin puts his hands on Deborah’s shoulders and pushes her to her knees. Eyeing the swelling in his pants, Deborah undoes his belt, her hands wandering over the growing bulge. She unbuttons the waist and quickly pulls the zipper down. She grabs the sides of his pants and briefs and pulls them together until his massive black cock pops loose. Her eyes widen as she peers on in amazement at the girth of the beast in front of her.

“Oh, I can never get over just how big you are,” she murmurs as she wraps a hand on the shaft, nowhere close to getting her fingers around.

Using both hands to lift the hefty member, she leans under it, putting her tongue at the base. She starts by

playing with his massive balls, licking them, and taking them into her mouth one at a time. Then slowly, she runs her tongue up to the still shrouded head. Her tongue circled the head, licking up and tasting the pre-cum forming there.

“Hmmm.”

She wraps her lips around the head and continues to play with it.

“Oh yeah, you like that cock. You’ve never had a cock this good,” Calvin says as he sees Deborah servicing him.

The alpha male that he is begins to take over. Deborah tries to put more of the massive cock in her mouth, but there isn’t any more room for much more past the head.

“We’ll work on that later,” Calvin says as he grabs Deborah’s shoulders and stands her up.

He turns her back toward the bed and slowly lowers her down on it. Deborah lifts her legs and spreads her knees for the bull about to ride her. Calvin grabs each thigh and pushes Deborah up the bed until her head is almost to the headboard. He then plants his face between her legs and licks her sopping wet pussy. Deborah moans as she closes

her eyes, leans her head back, and grabs the sheets in each hand. Her first orgasm is already hitting her.

Another orgasm hits Deborah as she squirms under Calvin’s tongue lashing. Satisfied with his work, Calvin moves up her body, kissing her belly and breathing softly over her skin as he reaches her breasts. Spending some time on each side, he licks and sucks her nipples. Deborah moans as he does this and puts her hands on his head. Calvin moves the rest of the way up, and he looks into her eyes. She’s staring back with overwhelming ecstasy.

“Are you ready?” he asks as he grabs her arms and pins them above her head.

She nods yes. As they look lustfully into each other’s eyes, Calvin slowly begins to push the head of his massive black cock past her wet pussy lips. Deborah gasps as her mouth open wider, and her eyes show worry. Calvin hesitates to give her a chance to adapt to the immense cock penetrating her.

“That’s it, girl. I love how you take my big cock.”

Calvin grins as he starts to push in again. Deborah gasps again as the head moves past her pussy lips, and the

shaft begins to enter her cunt. Calvin leans down and begins to kiss her. Distracting her as he continues to slide his cock deeper into her stretched, tight vagina. Deborah’s muffled moans are louder the more bottomless Calvin’s cock gets. He broke off the kiss as the last few inches of cock disappeared into her cunt. All ten inches of black cock are now in her body. Deborah wraps her legs tight around him, pulling him in closer, letting out a louder moan. Slowly, Calvin began pulling out and pushing inside again. Just a few inches at first, but more of his cock as his speed increases.

Letting go of her arms, Calvin lies on top of Deborah. With her arms free, she wraps them tight around Calvin and pulls him in as close as she can while he pounds her cunt. Harder and faster, Calvin fucks her. Her orgasms coming one after another, she goes between moaning and screaming in ways only a big cock can give that kind of primal fucking.

Calvin stops the relentless hammering long enough to sit up, roll Deborah over, and ram his cock back into her vagina. The hard impalement causes her to scream and lift

her body, but Calvin quickly grabs her arms, pinning them out to the side as he lies on her and continues his ruthless pounding of her cunt.

“Stay down,” Calvin commands. The man’s grunts turn into moans as he finally begins to climax. “Where do you want it? Where do you want my cum?”

“In my pussy,” she screams between moans and the impact of Calvin’s cock. “Fill me with your cum.”

“AAGHH,” Calvin moans as he forcefully slams into Deborah, leaning back as he plunges his black cock deep.

“OHHHH,” Deborah squeals.

Calvin loosens his grip on Deborah’s arms and lowers her back down, gently kissing the back of her neck. The two lay there, catching their breath, while Calvin’s cock still fills Deborah’s cunt. She pulls Calvin’s arms into her as she enjoys her post-climax high and closeness. After a few minutes, Calvin’s still massive cock shrinks and falls out of Deborah’s sloppy vagina. Calvin rolls off of Deborah and lies on his back next to her. It’s now that things went wrong for Deborah.

“Babe,” Calvin said, grabbing her leg and squeezing. “We need to talk.”

Deborah opens her eyes and turns her head to face her man. “What’s up, Cal?”

“Well, I been thinking, and I know we talked about being exclusive, but I’ve changed my mind.”

“What do you mean?” she asks and frowns.

“I got too much going on, babe,” he said with a shrug. “There are many fine ladies out there who want to ride my monster cock. I can’t tie myself down to just one.”

Her eyes bulge. She sits up in bed and slaps down on his face. “Get out. GET OUT, NOW.”

Calvin rubs his cheek, wincing some. “Don’t be like that, babe,” he tries to soothe her. “We can still have fun together.”

“GET OUT OF HERE NOW,” Deborah shouts.

Calvin gives in. There’s plenty of willing pussy in the city for him. He doesn’t need this bitch getting all needy. He climbs out of her bed, grabs his clothes and shoes off the floor, and heads to the door.

Before leaving her bedroom, he said, “If you change your mind, you have my number.”

“GET OUT.”

He shrugs and leaves the bedroom. A few minutes later (after he’s dressed), Deborah hears the front door open and close. She falls onto the bed and starts crying. The depth of feeling she was experiencing told her how hard she had fallen for the black man and his gigantic cock. ‘Was I that lonely?’ she wonders. ‘I fell for the first big cock that came along. God, what an idiot.’ Deborah gets out of bed, goes to the kitchen, and pours herself a glass of wine. She can’t get over how Calvin infected her life so quickly. ‘I guess I was ripe for the picking,’ she thought glumly. ‘A lonely woman new to New York. What would Nancy say if she found out that her maneater was a pussycat.’

She sits on her sofa and flicks the TV on to distract herself from her pain. ‘I need to get my mojo back,’ she thought, sipping her. ‘I need to find a man I can control, but where? Not on Tinder, that’s for sure. No, I need a more respectable guy. Maybe a type I don’t usually date

for a change.’ Deborah sniffles. Having your heart broken hurts on many levels. She had believed Calvin and she had a long-term future. Maybe even marriage and children if things worked out. The tears come rolling out, and she grabs a tissue and wipes her eyes. ‘I just need to find a way to meet this new guy that’s not online dating,’ she thought.

As if the gods had heard her plea, an ad begins on TV promoting short courses at a nearby community college. These courses are held at night and include pottery, leadlighting, learning piano, guitar, etc. So, she gets her laptop and looks up the college. As she scrolls through the various courses offered, Deborah finds one that piques her interest. It’s a beginner’s photography course. ‘Yeah, what a great place to practice photography,’ she thought. ‘New York has so many interesting places and weird people. It’ll give me an excuse to use that expensive SLR camera dad gave me as a going-away present.’

The idea perked her up, and the betrayal and loss at losing Calvin seemed to fade a little. After a few more sips

of wine, Deborah signs up for the course that starts in a week.

*****

She arrives at the college on the first night of the photography course a little late due to some issues at work. Nothing serious, just annoying. There’s only one seat available, and after apologizing for being late, she sits next to this good-looking brown-haired man around her age. The instructor, an older man in his fifties, runs through the basics of how a camera works. All the other students have their cameras in their hands, and instead of getting hers out and disrupting the class, she gazes at the guy next to her.

“You don’t mind if I look at your camera for now,” she whispers to him.

He turns, and his bright blue eyes flash. “Sure, no problems,” he whispers.

The class progresses, and she does get her camera out when the instructor suggests she had better, so she gets accustomed to it. Deborah pulls out a Canon 5D, and the man beside her nods his approval.

“Nice camera,” the man said with a smile. “That’s nearly top of the range.”

Deborah shrugs. “It was a gift,” she said. “I know nothing about things like that.”

By the end of the first class, the teacher showed them some basic settings and how to work the cameras each person brought. There were various cameras, from old film ones to the latest point-and-shoot digital cameras. He assigned them homework, namely, taking a photo of ten favorite things. The images can be of people, objects, and places.

As the class was packing up, the man beside her suddenly said, “I’m Sebastian.” Deborah smiles and introduces herself. Then he said, “I’m not usually this forward, but I wondered if you’d like to go out for a drink tonight?”

‘No way,’ she immediately thought. Then Deborah remembered her pact to date a guy she wouldn’t usually go for. Sebastian is an attractive man, but something about him seems so beta already. Deborah can generally sense it immediately in men; it’s part of her ability to break them

down and get them to talk. ‘Maybe a drink won’t hurt,’ she decides. ‘Besides, I got nothing better to do.’

“Sure, that would be nice,” Deborah said and smiled sweetly. “I know a bar not far from here. Maybe you can show me how to work this damn contraption.”

Sebastian chuckles. “A 5D is a lot of camera for a beginner,” he said. “But, great. I’m happy to help a fellow student.”

They walk to the bar, following many students with the same idea. Deborah tells Sebastian she’s a paralegal who recently moved to New York from Denver. Sebastian tells her he grew up in New York and has made a fortune in cryptocurrency speculation and the stock market.

“So, you do nothing?” she asks as they enter the bar.

He laughs. “I keep myself busy,” he said merrily. “But I don’t have a job like a regular person.”

“Cos, you’re rich?”
“Something like that,” he said.
“Well, in that case, you’re buying,” Deborah said, and

they both laughed.

“Why don’t you grab a booth, and I’ll get us some drinks. What’s your poison?”

“I’ll have a cosmopolitan,” she said and sat at a vacant booth.

Not long after, Sebastian returns with a cosmopolitan for her and a beer for himself. After he sits, he asks Deborah, “So, are you dating anyone now?”

She frowns. “Why do you want to know?”

He shrugs. “I wanna know where the boundaries are. I like you. I think you’re a beautiful woman, but it’s good to know at the outset if nothing happens between us. Saves all that hassle of getting your hopes up only to be let down.”

Deborah laughs. “I see. Sounds like you’re talking from experience.”

He grimaces. “Too much experience.”

“Well, I recently broke up with a guy,” she said, feeling awkward. “So, while I am single, I’m also not looking for anything serious.”

Sebastian nods and swills his beer. “Ah, I know what it’s like to have your heart broken,” he said sympathetically.

“My last girlfriend cheated on me. I can tell you it was a real kick in the guts.”

Deborah nods. “Yes, the guy I just dumped had the gall to tell me he wanted to see other women while seeing me. I told him to F off.”

He notices she’s finished her cosmopolitan. “Another round?” he asks.

“Why not. But I can’t drink too much. I have to work tomorrow. Unlike some rich people I know.”

He laughs and goes and buys them another round. When he returns, he proposes a toast. “Here’s to those who wish us well, and to those who don’t, go to hell,” he said, holding his beer aloft.

Deborah clinks his glass with hers, and they drink.

“You’re funny,” she said. “When did you break up with this cheating woman?”

“Oh, about four months ago,” he said. “I think she was only into me for my money.”

“That sucks. Maybe you shouldn’t flash it around so much,” Deborah suggests. “It only attracts the wrong sort.”

“I don’t flash it around,” Sebastian said, clasping his arms over his chest.

“You couldn’t wait to tell me how rich you were,” she teased. “That’s flashing it around.”

He frowns. “Oh, I suppose so. People ask me what I do, and I don’t know how to answer.”

“Hmmm, you could say you’re an investment broker, maybe. Give her the impression you have a regular job.”

He smiles. “You’re full of good advice. But should a paralegal be telling me to lie?”

Deborah laughs. “Only in matters of the heart,” she said. “Oh, and tell her your cock is bigger than it is.”

He nearly spits his beer out. “WHAT?”

“Don’t exaggerate it, but put a little mayo on it to get her into your bed.”

He stares at her for a moment and bursts out laughing. “You’re something else,” he said, slapping the tabletop.

“It works, though. If she dumps you after all that, you dodged a bullet. If she stays with you even though she thinks you’re just an average guy with a boring job, you know she likes you, well, for you.”

“Well, this night took a strange turn,” he said, grabbing his empty glass and hers and buying another round.

The two seem to talk for hours and slowly get drunk. Eventually, she calls an UBER, and he walks her to the car when it arrives. They go to kiss goodnight, and what was meant to be a peck is unexpectedly French kissing. They stand like that for a good few minutes until the driver complains.

“Why don’t you come back to my place,” Deborah whispers.

*****

Deborah smiled, scooting over so that Sebastian had room to get in beside her. The UBER driver glanced at the two in the back seat. He suppressed it if he was the type to comment on certain things. The address suggested the possibility of an above-average tip, and he wasn’t about to jeopardize that. The ride is spent in silence. Deborah occasionally glances sideways at Sebastian. The UBER only takes ten minutes to reach its destination as the roads are pretty empty. Once they arrive, Sebastian gets out of

the UBER first, holding the door open for Deborah while she tips the driver.

One step into the lobby of the building made it evident that Deborah lived very well, if only because they were greeted by a doorman who was more neatly dressed than Sebastian.

“Good evening, Ms. Hewson.” he smiled at Deborah with a nod of acknowledgment for Sebastian. “How was your photography class tonight?”

“Oh, it was interesting,” Deborah said as they passed the man.

As they enter the lobby, Sebastian takes in her surroundings. The floor is a pleasantly geometric pattern of black and white marble, converging about two-thirds of the way between the elevator and the doors they had entered. Some strategically placed couches and plants broke up the acoustics enough to stop footsteps from echoing too loudly. Everything is illuminated by soft yellow light coming from a chandelier hanging in the center of the open area, a modern thing of steel and glass

pipes, with wall-mounted lights picking up some of its slack around the edges.

One of the elevators opens in response to Deborah producing a key fob from her purse and holding it up against a panel of matte black glass. It wasn’t until the doors closed that he turned to her and said, “You never told me your building has a doorman.”

“I never expected you to come to my apartment.” Deborah shrugged before adding, “He’s not going to breathe a word about you coming home with me if that’s what you’re worried about.”

Sebastian smiles. “No, I didn’t mean that,” he said. “It’s just how you talked about being a working stiff, living in upper Manhattan.”

“My place belongs to the firm I work for,” she explains. “I could never afford a place like this on my salary.”

The high hallway they step into has a subtly vaulted ceiling, with circles of pale yellow light running along the very top of the arch, forming an illumination line on the black marble floors. Their footsteps create soft echoes as they move.

Sebastian watches as Deborah pulls out her keys. “Um. I didn’t exactly expect guests,” she said, holding the doorknob.

Sebastian gives a slight shrug. He has a hard time imagining Deborah’s apartment being anything other than pristine, even if she wasn’t expecting visitors. Much to his relief, his assessment turned out to be correct. The front door opens up into the darkness. Sebastian can just make out the silhouettes of the furniture with what little light comes in from the windows. They move into a living room of modern minimalism, the furniture primarily black and white, with framed art prints on the wall to create color. The only thing that seems out of place is a red fleece blanket pooled on the black leather couch.

turns to find that Deborah has taken off her coat and shoes, making her about an inch and a half shorter than she has been in her heels. She held out her arm. “Can I take your coat?” she asked softly.

Sebastian nods and sheds it, handing it to Deborah. He watches her briefly retreat to the front door to hang them from the coat rack. Then Deborah turns back to Sebastian.

“So, how would you like to do this?” he asks.

“Well,” she smiled as she moved toward Sebastian. She takes the man’s hands in hers, bringing them to her lips and softly kissing along the knuckles. All the while, she holds eye contact. “That depends. Would you like to sit and talk for a while? We could have another drink. We could also just go to the bedroom, and, you know.”

Her left-hand lets go of Sebastian’s right, but she uses the other to guide Sebastian along. The man smiled and let himself be led, stepping out of his shoes as he followed Deborah’s lead. Their destination turns out to be a door to the main bedroom. As Deborah turns on the light, Sebastian sees that the general aesthetic matches the living room, although smaller than he imagined. He was still taking it all in when Deborah released his hand.

“I’m just going to take a moment to change. I’ll be right back.”

Sebastian nods, watching Deborah disappear into what he assumed to be a walk-in closet. The woman closes the door behind her, so Sebastian decides to take in the city views. He became so lost in the view that he didn’t realize

Deborah had returned until the woman placed a hand on his shoulder.

Sebastian turns and is caught off guard. He’s just barely allowed to take in the sight of Deborah wearing some wonderfully lacy underwear in a dark red color that has been picked out to complement the porcelain tones of her skin. Then he’s deprived of that view by Deborah’s hands pushing against his shoulders, pressing him into the gauze curtains. The man feels his back pressing into the glass of the window. The kiss is deep and full of need. Their lips meet, and soon their tongues do the same, and Sebastian gives himself over to her desires. He will remember the moment later, the first time he let Deborah take charge.

After a few moments, he feels Deborah’s arms wrap around him in an embrace. He let Deborah pull him forward. The king-sized bed looms behind them. Just as he becomes aware of its presence, Deborah pushes him, making Sebastian pivot on the spot. He let out a surprised giggle as the edge of the bed hit the back of his legs, leaving Deborah with barely any need to push to send him tumbling onto it. A moment later, Deborah straddles him.

“It’s been a while since I had someone up here.” Deborah grins.

“Well, you have me here now.” Sebastian smiled. “But let me do the honors.”

Deborah nods, reaching up to stroke Sebastian’s neck and face. “We have all night.” Deborah paused. She can see the tension in Sebastian’s eyes, something that hadn’t been there before. “Hey?” she asks. “You alright?”

“Yes, yes,” Sebastian said. “It’s just—” He glances down. “Sorry, I didn’t exactly plan to get undressed in front of anyone tonight.”

A moment later, Deborah’s hands find Sebastian’s, pinning them over his head as she leans in, their lips meeting again. Sebastian feels a shudder run through his body as he closes his eyes. And then Deborah’s mouth detaches itself, but only so she can slide hower, unbuttoning his shirt as she goes and exposing his surprisingly ripped body. There are playful nips of teeth between the kisses, enough to draw small gasps from Sebastian’s lips even if they aren’t strong enough to mark his skin. The intimate contact makes Sebastian grateful he

has worn his favorite cologne tonight. His hands curled into fists as Deborah helped herself to his body.

Sebastian sighs as he feels his torso explored by Deborah’s mouth and lips. “Please, let me,” he said, his eyes pleading, which Deborah finds odd but charming.

“If you insist,” Deborah said, feeling playful.

He rolls Deborah over swiftly, so she’s now lying on the bed, and he’s on top.

Then, just as Deborah is about to lift her hips to make further removal of her panties easier, Sebastian says, “On your stomach.”

Deborah licks her lips and nods. His lips gently press on Deborah’s neck, kissing her among her ringlets. Deborah’s fingers grasp two handfuls of the sheets as she arches her spine delicately. His fingers drag along Deborah’s slit even as her teeth gently graze over the skin of her backside.

“Oh, yes,” is all Deborah said.

She trusted Sebastian utterly, and now it’s rewarded by pressure against her right butt cheek that soon leaves her tight little pucker exposed. Sebastian’s tongue against it is electricity. He drags it upward slowly, tensing the nimble

muscle as he teases it along the crinkled skin. The sensation mingled with those teasing fingers between her folds left Deborah gasping softly, her nostrils flaring, the sheets bunching in her grasping fingers. The brown-haired woman can hear Sebastian sigh behind her, clearly pleased with the reactions he’s drawing out of her. The sound escapes Deborah’s throat as he teases the sensitive skin of her taint between a gasp and a squeal, full of surprise at Sebastian’s inventiveness.

She gazes over her shoulder to see that Sebastian has a grin on his face. That grin disappears between her cheeks a moment later, and Deborah is left to gasp and shiver again. Sebastian’s tongue probes her anus to set off little bursts of pleasure in the pit of her stomach. She spreads her legs wider, giving Sebastian’s fingers an opening to probe further against her pussy. Despite the awkward angle, Sebastian knows what he’s doing between the woman’s thighs. Deborah’s hips give little jerks, usually accompanied by soft gasps, as Sebastian’s lips, tongue, or fingers find a susceptible area to tease.

All Deborah has to do is lie there and make a mess of the bed for her part. She keeps grabbing fresh handfuls of cotton, drawing more and more of the sheets toward herself as she writhed underneath Sebastian’s manipulations of her curvy body.

Deborah’s breath comes out in hitching gasps and quivering moans. She can feel a tightness in her abdominal muscles that tells her Sebastian’s work has its intended effect between her legs. She squeezes her eyes tighter as the waves of pleasure begin to crest, and Sebastian is given a more direct taste of her most intimate fluids. Her hips jerk erratically in time with the contractions of her pelvic muscles. Sebastian purrs against the tight ring, enjoying the feeling of Deborah’s body tightening around his probing digits.

Eventually, the haze of orgasm lifts, and what is left is an incredible sensitivity in Deborah’s loins. He pulls away reluctantly, and she tries to roll over onto her back.

“Where do you think you’re going?” he asked, his voice husky.

“I need you to fuck me,” Deborah moans. “I need to feel your big cock inside me.”

Chapter 2

Sebastian gets off the bed and starts taking off his jeans and boxers. The room is dark, and Deborah can’t see anything from the bed. “Oh, babe, I can’t wait to fuck you,” Sebastian moans, finally getting his jeans off.

“I need it so bad,” Deborah moans, spreading her legs as he climbs on top of her.

The kiss, tongues probing each other’s mouth as he positions himself to plunge his erect penis inside her vagina. Then he firmly thrusts and enters her cunt, feeling the velvety warmth inside envelope him.

“Oh God, that feels so good,” Sebastian said, thrusting his hips to fuck Deborah harder.

He goes on like this for a minute, enjoying himself immensely, while she lies there with a frown forming on her face. “Can you go deeper?” Deborah suddenly asks.

“I’m trying, but I am already balls-deep,” Sebastian said, pushing harder inside her.

“Try to put your tip as close to the cervix as possible. I don’t feel anything.” He thrusts into her, reveling in the silky sensations of her cuntal walls around his cock, when she asks, “Is that it?”

He gazes down at her knowing immediately what’s happening. “What do you mean?” Sebastian asks, knowing full well what she means.

“I mean, your, err, dick. I can barely feel it. How big is it?” Deborah asks with annoyance creeping into her voice.

“It’s big enough,” he said, but she burst out laughing, shutting him up.

His erection fades fast, and Deborah pushes him off her, so he lies beside her. She leans over and turns on the light. Then, she holds up the covers, looks at his groin, and inspects the goods.

“Wow, that’s a small one. I can usually spot guys like you. I have to admit you fooled me a little.”

The way she looks at him, rolling her eyes while smirking, conjures those feelings of inadequacy in Sebastian only a tiny dick man can know.

“It’s not that small,” he said weakly, feeling his face go hot.

Deborah climbs out of bed, reaching for her robe and putting it on. She turns and looks at him, and for a moment, he thought he saw pity in her eyes. “How big is it anyway?” she asks.

He shrugs. “I’ve never measured it.”

Deborah laughs in a way that makes him shiver. “Don’t lie to me,” she said, amused. “All guys measure their dicks. Especially those with little ones like you. You can tell me. I won’t tell anyone about it, I promise.”

He swallows. “Um, it’s four and a half inches hard and two and a half inches soft,” he said, staring down at the sheets below.

There’s silence. He’s expecting her to laugh or do something nasty, and he waits for her reaction to fall like an avalanche of shame to cover his soul. Then, to his

surprise, he feels Deborah get on the bed and put her arm around him in a tender embrace.

“That was brave of you,” she said. “I know women can sometimes be cruel to guys like you.”

Her words shake him from his stupor, and he slowly turns his head to gaze into her blue eyes. “You don’t mind?” he asks disbelievingly. His eyes are wide and innocent.

Deborah shrugs. “You’re a nice guy, Sebastian. I sense that about you,” she said softly. “I’m sorry if what I said hurt you. I’m just not used to having sex with smaller, err, dicks. Besides, your oral skills must be the best I’ve experienced from a guy.”

“Thanks, I guess,” he mumbles.
“I feel a ‘but’ coming on,” she said and smiled.
He nods. “But I wanna make a woman cum with my

dick to feel like a man.”
“Have you ever done that?”
He shakes his head with a pout. “No, they never feel it.” Deborah giggles. “Maybe we can try it. I know some

positions that could help.”

His eyes bulge. “You’d do that?”
“Why not? I’m not a bitch,” she said sweetly. “What positions do you think might work?” “Hmm, let me see,” she said, forming a cute frown.

“Maybe from behind while you’re spooning me. That way, I can squeeze down on you.”

He nods and grins excitedly. They got into position, and he poked his boner between her ass cheeks. Sebastian tries to enter her vagina but can’t get much inside. Big surprise. “Can you feel it?” he asks.

“No. You’re too short.”

He kept trying and couldn’t find a good spot or angle to get more inside, so he asked for her help. Deborah feels around, grabs the head of his tiny boner, puts it at the entrance, and says, “OK, can you reach it?”

He started a little thrust and said, “There we go. Does it feel good?”

“Not really. I can’t feel it much. Let’s try something else.”

Sebastian moves between her legs as Deborah rolls onto her back, and he slides his tiny boner inside and starts thrusting.

“I’m sorry I’m so small,” he said.
“It’s fine. It’s not your fault you were born this way.” He shrugs and says, “Yeah, I guess.”
“Let’s go. You have thirty seconds,” she said, reaching

around to find his balls. “Wow, even your balls are tiny. I can barely find them.”

She squeezes them hard. “Well, maybe we can try spooning again later, and I can move around a bit, and it’ll feel better,” he said.

“We could, but you’re too small, so I doubt I’ll feel anything.”

Then Sebastian climaxes. He grunts and shivers as he spurts his jizz into her cunt. Deborah is amused at his orgasm face, but she doesn’t feel much from his efforts.

“OK, I think you’ve left quite a mess there,” Deborah said. “Your poor little balls have been saving that up, eh? You know what to do.”

She wanted him to lick her dripping pussy, so he did. As he worked his way down the bed so his face was in front of her pussy, she leaned back and parted her knees. Gazing between Deborah’s legs, she confirms the obvious.

“Touch it,” she said. “Tell me what you think.”

The sexual aroma wafts to Sebastian’s sinuses. It was exciting to see how wet and horny she was, but the intensity of that aroma instantly drove him wild with lust.

Seemingly enjoying the sensation of Sebastian’s massaging fingers, Deborah closes her eyes as he squishes the liquid puddle in her crotch. Knowing just how much she likes his pussy licking skills. He sees his opening and takes it. However, he’s inspired to be a little creative. Her eyes were still closed. Sebastian decides to demonstrate just how much he craves her secretions. He begins licking and nibbling at her pussy lips and clit. She flinches. Surprised by Sebastian’s direct oral attack, her eyelids fly open.

Then with a crooked smile, “God, I’ve never known a man who can eat pussy like you.”

As he begins to lick, her juices' intense flavor and thickness stun him. It’s so thick he can hardly draw it through her pussy lips. His mind numbs from the aroma and taste. Sebastian’s tongue retrieves more. It seems so erotic for her cunt to be so full of hot fluid and for him to be sucking so hard to draw it out. Deborah moans with pleasure while parting her legs further. But the longer he licks, the hotter and more lust-filled he becomes. He's eager to get even more of her excellent slime mixed with his jizz.

“Go on. Finish what you started,” Deborah commands. “Lick it up.”

Looking at Deborah’s pussy, a semi-clear, almost pearl-like fluid covers the trimmed pubic hairs and the insides of her thighs. The juices begin to flow much thicker, sticky, and plentiful. It was the most erotic thing he had ever seen. Sebastian’s brain goes into lust-filled overload. He had never experienced a pussy so full, secretions so creamy, smelling so strongly, or looking so inviting. He then dives into her open flower tongue first.

Lustful wishes want to believe this is all because she’s super-horny for Sebastian’s ‘talented tongue,’ as she said. He’s convinced Deborah wants him, and he isn’t about to let her down. It probably wouldn’t have mattered what it tasted like. To Sebastian’s way of thinking, anything flowing from this woman’s pussy must taste great. Pulling her hips toward him and placing her legs over his shoulders, he buries his face into her womanhood, working harder than ever to suck the hot flowing nectar.

“God, why are you so good at this,” she said between moans. “I don’t think even another woman could do it better.”

He tilts his head to show her how much he appreciated what she had done for him, letting her see some of the secretions filling his mouth. When she sees her pussy slime mixed with his jizz, Deborah swoons.

“This makes up for your tiny dick, Sebastian,” she said.

He groans his approval. While the man slurps away, she purrs and whispers about how good it all feels. Then, as he moves to suck on her clit, her orgasm triggers, and Deborah starts writhing on the bed. He keeps sucking on

her clit, pushing her through multiple orgasms as he fingers her contracting cunt.

“Oh, God. Cumming. It’s so good,” Deborah moans.

He licks the last remnants of her creampie, feeling proud it was his jizz inside her cunt and how hard he had made her orgasm. Eventually, they fell asleep in an exhausted mess of sticky bodies. Sebastian goes to sleep, hoping his luck has finally changed and he’s met a woman who can appreciate him.

*****

Deborah dates Sebastian frequently over the next few months, developing quite a bond. She sticks with him because he’s rich and can eat pussy like a demon. Without these incentives, she would have dumped him after the first night and moved on pretty quickly. Sebastian naturally doesn’t know this and thinks all his Christmases have come at once. He’s more used to the woman dumping him, so to have one stick around has made him very happy. Still, Deborah finds that hanging out with Sebastian has helped her adjust to New York City. She’s

now made some friends and feels more at home in the city that never sleeps.

When Sebastian’s birthday came around, Deborah decided to give him a surprise gift. So, after a lovely evening out with him, they return to her apartment, and she has him sit on the sofa. A chair stands in the middle of the room. Deborah clicks a remote at her stereo player. She then goes over and stands beside a chair. She felt her legs turning to jelly as the first music track starts.

Sebastian sits directly in front of her. His eyes never leave her. She is beginning to feel good. ‘It’s getting hot in here’ starts playing, and Deborah starts dancing sensually, touching her body suggestively as she moves. The first track ends. Deborah feels more confident. The dancing warms her up, and the nervousness has all but gone. She slips out of her dress almost as soon as the second track starts; it’s Rocket by Beyonce.

She placed her dress carefully over the back of the chair. Then she sits on the chair, her back to Sebastian. She reaches behind her back for the clasp on her bra. Deborah can feel his eyes boring into her back. It fills her with an

excitement she hasn’t felt for a long time. Deborah let the bra straps fall from her shoulders and slipped each arm after waiting a moment. Holding the bra cup to her body, she stands and turns to face him. Sebastian’s eyes are on her as she turns again and lifts her bra above her head. She gazes down at her DD-cup breasts. She likes what she sees. Then she spins round to face him again.

Showing her breasts was easy. She senses Sebastian is getting excited. ‘As he should,’ Deborah thought. ‘I have a great body, and I’m proud to show it off.’ She keeps smiling. Sitting in the chair again, she spreads her legs to reveal her panty-covered crotch making Sebastian moan and squirm. His reaction encouraged her. She gazes into Sebastian’s eyes.

Deborah is on the chair facing him just as the second song ends. She stares straight at Sebastian. Another song starts; it’s ‘Buttons’ by the Pussycat Dolls. Deborah raises her legs toward the ceiling and slips her panties past her bottom as the groove takes hold. It’s just enough to give a little glimpse, but as she holds her legs firmly together, a glance is all Sebastian gets. She brings her legs down

gracefully and slips her panties past her ankles. She then stands and kicks them aside. Sebastian first sees her nudity as she dances around the room.

Again, she sits on the chair, facing him. She leaned back on the chair and raised her legs in a vee, far apart. A hand still hides her secret place. She leers at Sebastian and raises her hand. He keeps eye contact with her, to her amazement, instead of staring at her now shaved pussy. Then he weakens and casts his eyes down at her beautiful pussy. Deborah slides herself forward off the chair, her legs still wide apart for most of this third track. She’s now sitting with her back against the chair. She gently pushes the chair back until she’s lying on her back. Again, she lifts her legs into a vee offering Sebastian a perfect view. She rolls onto her side, still keeping her legs apart. Sebastian is drooling.

Deborah gets to her feet and takes one stride to the front of the panting man. She then steps onto the sofa and lowers herself onto Sebastian’s face. Her pussy is now inches away from him. She’s enjoying it more than she expected. As the music stops, she’s elated beyond belief.

“Happy birthday,” she said softly, feeling his hot breath on her pussy lips.

“Oh, God. I love you, Deborah,” Sebastian almost moans and starts licking her pussy to taste her juices. “I love you so much.”

“Oh, Sebastian,” she moans, feeling his tongue slide deep into her cunt.

Another night of pussy eating ensues. She lets him fuck her but doesn’t feel his tiny dick and afterward makes him eat her creampie. It’s not the perfect relationship for Deborah, but her intense feelings for Sebastian stop her from craving alpha cock for now, and she takes that as a sign this partner is right for her for the moment.

*****

The following day at breakfast, Deborah tells Sebastian her work has asked her to find new accommodation as they will need the apartment soon for some out-of-town clients.

“Move in with me,” Sebastian said with a smile.

She frowns. “I don’t know. We haven’t been dating for that long. It’s a big step.”

“My apartment is just as nice as this one. Maybe nicer.” She laughs. “OK, Mr. Money Bags. I get it. You’re rich.” “Plus, it’s closer to your work,” Sebastian presses.

“Besides, do you know how hard it is to find a decent apartment in New York? From what I’ve heard and read, it’s a nightmare.”

“You make a good argument,” Deborah said, sipping her coffee.

“The rent is cheap.”
“How much?”
“Zero dollars, just like here,” he said and laughed. “How can I refuse,” Deborah said, pushing her hand

across the table, and they shook on it.
“Good, we’ll move you in next weekend,” he said

excitedly. “I’ll get you a key.”
“And if it doesn’t work? What happens then?”
He frowns. “What do you mean? Why shouldn’t it

work?”
Deborah sips her coffee again to stall for time while she

thinks of the wording of her response to his question. While her time with Sebastian has been fun, she feels

something is missing in her life. Something Sebastian can’t give her—a proper fucking with a large cock.

“Come on, spit it out,” Sebastian urges. “Whatever it is, I’m sure we can figure it out.”

She takes a deep breath. “Well, I feel guilty saying this just after your birthday, and the great time we had last night. Your oral skills are unbelievable.”

“But?” he asks with a raised eyebrow.

“I told you on our first night together that I dated men with big cocks before you. ‘The bigger the better’ was my motto. Before you, the guy I dated had a ten-inch hog between his legs.”

Sebastian’s face turns bright red. “Are you breaking up with me now?” he asks, feeling his stomach roil. “I thought you were moving in with me?”

“No, not at all,” she said, waving her hands in a conciliatory manner. “I just want to be honest with you. Isn’t that the good foundation of any relationship—honest communication?”

“I guess.”

“I want you to know the kind of woman you’re living with. I’m sure you have things you haven’t told me or want me to understand about you.”

He gazes down at the table. She immediately recognizes the gesture as a paralegal all her years as a deflection. ‘He’s hiding something,’ she thought. ‘Something he wants to tell me but isn’t sure if he can.’

“Whatever it is, you can tell me,” she said, taking his hand in a loving gesture.

His head rises, and his eyes meet hers. “It’s silly, nothing to worry about.”

“I don’t think so,” Deborah said calmly. “It means enough to you to feel hesitant about it. You can trust me.” Sebastian shrugs. “When I was younger, I liked to dress

in my mom’s clothes.”
The brunette woman sits back, keeping her smile

planted but feeling awkward. “What like dress-ups when you were a kid?” she asks, hoping this is all it was.

“No, when I was fifteen, I started dressing in her panties and bras cos it made me feel sexy. I would pretend I was a girl.”

The smile on Deborah’s face is still there, but there’s no feeling behind it now. Her eyes are cold. ‘God, I knew he was on the beta side of the male spectrum, but this is something else,’ she thought. ‘Is he a sissy too? It can’t be, or I would have picked it by now. Then again, why make this confession to me? Does he want to wear my clothes?’

“Are you mad at me?” he asks pensively.

“I just don’t understand why you would tell me that,” she said, colder than she meant. “I mean, are you still into crossdressing? Is this what you’re trying to tell me?”

His face is so red that Deborah can almost feel the heat from his cheeks. “No. I-I don’t know why I told you that,” his shoulders sank. “I haven’t even thought about it for years now. I’m sorry, I’m such an idiot.”

‘Yes, you are,’ Deborah thought. ‘Why do insecure men always self-sabotage their lives? I see it all the time. He has the chance to be with me, and he drops that bomb to see if our relationship will implode or maybe to sow the seeds of our eventual end.’

“So, I’m not going to come home one day and find you in my panties and bra?” she asks, stifling a laugh at the mental image in her mind.

“Oh, heavens no,” he said, shaking his head. “I promise I’ll never do that. You have my word as a gentleman.”

Deborah stands and refills her coffee. I can’t dump the guy just because he tried crossdressing once. Guys are just awful when they’re teenagers. I bet he jerked off in his mommy’s panties like a little pervert. I’ll have to see how it goes.’

“OK. Let’s not speak of it again then,” she snaps. “Let’s pretend this conversation never took place. It’s for the best.”

“What about your big cock desires? Can I take it we’ll forget about that too?” Sebastian asks sarcastically.

She sits back, snapping her head high. “I’ll make you a promise, Sebastian. If we’re together, I will never have sex with a big cock unless you ask me to.”

“I’ll never ask you that,” he said, shaking his head. Deborah smiles. ‘We’ll see,’ she thought. ‘We’ll see.’

Chapter 3

Deborah moves in with Sebastian in his apartment in the West Village. The place owned by her work was pretty swanky, but Deborah soon realizes Sebastian’s apartment is another level above that. It’s in a high-rise building with a doorman, and the apartment covers half of the twentieth floor. The view is incredible. A well-known New York sports celebrity owns the other half, which she didn’t discover until moving in. Sebastian was dismissive when she asked him why he never told her about his famous neighbor.

“Number one rule of living here,” he said. “Neighbors respect each other’s privacy at all times. No matter who you see here, you never speak of it to anyone.”

Deborah laughed. “Spoilsport,” she said.

“I’m not kidding. You’ll see famous people here, and while that may excite you, they are still people. They and their guests deserve to feel comfortable in their homes without being gawked at or reading about stuff that happens here in the rags.”

“OK. OK, I get it,” she said, waving her hands defensively. “My lips are sealed.”

“Good. So, what do you want to do tonight to celebrate moving in?”

She thinks for a moment. “How about we go out to a nightclub? There are some excellent ones in the West Village.”

He nods. “I know the owner of ‘Provocateur.’ I can call him and get our names on the list?”

Her eyes bulge. ‘Provocateur? Oh my God, why have you withheld this information from me before? I tried getting in there once, and they wouldn’t let me in.”

“Yeah, it’s pretty snobbish if you ask me,” Sebastian said, shaking his head. “I find that whole scene distasteful.”

“How do you know the owner?” she asks.
“We are old friends from college,” is all Sebastian said. “Then call him. I want to go to that club,” Deborah

urges, and he gets his cell phone out and calls. *****

Later that night, Sebastian enjoys seeing Deborah prepare for the date to the nightclub Provocateur. Her lithe body always turns Sebastian on when she moves around, especially naked. Her DD breasts bouncing or her butt wiggling does it for him every time. He cannot resist, so he gets behind her as she’s looking in her wardrobe for an outfit for tonight and wraps his arms around her. Then moving her brown hair out of the way, he nuzzles into her neck, tasting her soft, fresh skin and making her laugh as he teases her ear with his tongue.

Sebastian spins Deborah around and pushes her onto the king-size bed, not letting her go. He groans excitedly as he takes one of her large hard nipples into his mouth and rolls the tender teat around with his tongue. Sebastian’s rewarded with a low moan as he trails his kisses lower. He pushes open her slit, slides his tongue over her clit, and thrusts against her tight vagina.

Deborah starts to giggle. “Hey, our cab will be here soon,” she said, lifting her head off the bed and staring at Sebastian with raised eyebrows.

She vainly pushes at his head, yet he soon gets past her passive resistance and puts the thought out of her mind as he attacks her clit with his tongue. Her knees come up as she squirms while the warm, sweet taste of her pussy juices fills his mouth. When Deborah orgasms, she gets mildly tender around her clit, and he always pushes the limits and gently licks at her love button while she tries to move his head away from between her legs.

“Stop it, God, I can’t take anymore,” she moans, pushing on his head.

Smiling and wiping his chin, he pulls her up, so she’s face to face with his dick. He stands proudly, pre-cum dripping off the swollen end just inches from her face. Her big blue eyes glance at Sebastian’s face, and she slaps his small dick making him jump.

“Get your dicklette outta my face,” she said with a smirk. “Now get on the bed, and I’ll ride it.”

Sebastian gets on the bed, and she rolls a condom down his little rocket, and to make sure it stays in place, she snaps the latex over his balls. Her hot, tight, juicy cunt is on his dick in one swift motion, rolling her ass around.

“It’s inside me, but I can’t feel much, Sebastian,” she said. “It’s like I have my little finger up there.”

He’s never sure if she’s taking the piss or if she means it. Sebastian shoots his load with a grunt. After his orgasm fades, he opens his eyes to see her smiling face staring down at him.

“Look who’s a horny boy tonight,” she teases.

“I guess I like having my girlfriend living with me,” he said happily.

Sebastian wants to go again, yet the cab is due now. He watches her quickly jump into the shower and wash again. He feels like a lucky man with a sexy girlfriend as he watches her slide her soapy hands over her curvy body. Sebastian dumps the used condom into the bin and washes his dick in the sink.

Soon they’re dressed and waiting for the doorman to buzz them to tell them the cab is waiting for them. Deborah wears a short black cocktail dress with no stockings. Her legs appear enticing as he follows the soft curve of her legs from her heels to her bubble butt hidden beneath the hem of her dress. She squeezes her ample

cleavage to tease Sebastian. He can’t help himself and slides a hand over her back to trace her curves. A slight feeling of disappointment takes him as he’s about to lift her dress and squeeze her ass because the intercom buzzes.

*****

Deborah orders the driver to take them to Provocateur when they're in the cab.

“This is so exciting,” she said and kissed Sebastian. “I can’t wait to see what it’s like inside.”

“It looks like any nightclub, to be honest,” Sebastian said. “So, you wanna party, eh?”

“Fuck, yeah. I wanna dance the night away.”

Eventually, they arrive, and the queue outside Provocateur is long. Most hopefuls want to get are young and attractive and dressed in the latest designer clothes. But that is still not enough to enter this nightclub. Sebastian understands that if he didn’t know the owner of this place, he and Deborah probably wouldn’t get in either. As they approach the door, the security eyes them off at first until one of them says, “Hey, Seb. It’s been a while.”

“Thanks, Garth. I think Johnny put us on the VIP list. This is my girlfriend, Deborah.”

Garth scans the list and says, “Yeah, you’re on here. You can go in. Have a good night.”

They soon get in, and the place is packed with sweaty dancing bodies. Deborah finds a spot on the corner of the dance floor, and Sebastian heads to the bar for the drinks. The drinks take ages to get, as it’s so crowded and he’s short. So, to get served, he must shout and wave his arms. He orders three doubles for them to save coming back, then squeezes through the crowd toward Deborah, who’s doing her thing to the thumping dance music.

He gasps, and his body stiffens when he sees her dancing people. Sebastian doesn’t consider himself jealous, yet something troubles him as he watches Deborah dancing with a black man. He knows from past experiences that Deborah has always been the type to dance with anyone, and given any chance, she loves to show off her moves. The dance floor is crowded, so the two are dancing close. When she sees Sebastian watching,

she gives him a cheeky smile as the black man’s hands slide over her body in time with the music.

After a few more tracks, she makes her way through the people to Sebastian, and the black guy follows her. The black man is at least six feet four, so he towers over Deborah and Sebastian.

She takes her drink and shouts in his ear, “This is Rick.”

Sebastian’s hands hold the drinks, so he nods his head to the black man, who nods back with a grin. His teeth are blue due to the ultraviolet light of the club.

“I hope you don’t mind me dancing with your girl,” Rick said, shaking Sebastian’s hand.

‘I do mind,’ Sebastian thought insolently. ‘I wish you’d just fuck off.’ However, as he gazes at the buff man, a feeling of inadequacy springs from his loins, making Sebastian squeak. Yes, the sense of weakness emanates from his tiny dick. Rick’s brown eyes bore into his, measuring what kind of man Sebastian is. Deborah watches, fascinated by the interaction. She’s wondering if her boyfriend is man enough to tell Rick she is taken.

“I don’t mind, I suppose,” Sebastian said as Rick let go of his hand.

“What a good sport,” Rick said in a condescending tone. “I promise I’ll return her to you in one piece.”

“Why don’t you get us a booth, honey,” Deborah said. “I won’t be too long, I promise.”

After downing her drink, Deborah grabs Rick and pulls him back onto the dance floor. Rick has all the moves as he gyrates and bumps against Deborah, and she grinds her back into his crotch. He loses sight of Deborah in the sea of sweaty bodies and grabs a vacant booth.

Meanwhile, Deborah is busily swatting Rick away because, like all alpha men that sniff out some easy prey, he’s going in for the kill. She is attracted to Rick, and his noticeable bulge indicates he has a big cock, but she’s more interested in how Sebastian handles the situation. The way he backed down when he met Rick annoyed her on one level, but seeing him be so weak also turned her on a little. She decides to test it out to see how her boyfriend might react.

“Let’s go get a drink,” she shouts to Rick over the music, and he nods.

They go to the booth where Sebastian sits glumly, drinking imported beer from a bottle. Rick leaves them to go to the bar, and Deborah sits.

“How are you, honey,” she asks with a smile.

“Just great,” he says sarcastically. “Rick and you seem to be getting along well.”

She shrugs and takes the vodka and Red Bull drink Sebastian had waiting for her. “He’s a nice guy,” she said. Then she notices his petulant gaze. “You’re welcome to come up and dance with me. I can’t help it if men are attracted to me.”

Sebastian is about to say something he would regret when Rick suddenly sits in the booth next to Deborah. He holds his tongue. Rick smiles and Deborah and nods at Sebastian.

“Hey, what’s the story with you two?” he asks Sebastian. “What do you mean?”

I don’t know. Maybe you’re one of those affluent kinky white couples looking for a hung black stud. You know what I mean?”

Sebastian glares at Deborah. “No, I don’t,” he said coldly to Rick.

Deborah is watching it all unfold, enjoying the show.

Rick continues. “What do they call it? Um, cuckolding, yeah, that’s it, cuckolding. Are you a cuck, Sebastian? Have you got one of those little white boy dicks that can’t satisfy Deborah?”

Sebastian seems to shrink in his chair at Rick’s bold words. Deborah feels a gush of wetness dribble into her pussy lips. She doesn’t know why, but this strange conversation makes her horny. ‘A real man would tell Rick to fuck off,’ she thought. ‘Then again, Sebastian isn’t a real man. He’s a little boy who likes to wear his mommy’s panties.’

“I think Sebastian is more a wannabe cuckold,” she said to Rick. “He certainly meets the criteria.”

Sebastian gasps, and his eyes bulge. “Deborah,” he groans, shaking his head.

She shrugs. “Well, you have a little dick, so Rick isn’t wrong about that.”

“You bitch,” Sebastian shouts, gets out of the booth and disappears into the crowd of hot bodies.

Rick laughs coldly. “That was pretty harsh, Deborah,” he said.

“You started it,” she said, punching his arm.

“Only cos you told me too on the dance floor. I’d never say shit like that to anyone, even if I thought it. I’m not like that.”

“I just wanted to see if my boyfriend was a man.”

Rick shakes his head. “Well, I need to go pee. I’ll see you around.”

The black man leaves her alone, and she doesn’t see him again. However, Deborah isn’t fazed. She wonders if she can manipulate Sebastian into crossdressing again. ‘God, that would be funny,’ she thought. ‘It might spice up our sex life too. But I can’t let him know I’m doing it on purpose.’ She gets up and finds Sebastian sulking at the bar. After cuddling up to him and sweet-talking him for a time, they leave and go home.

*****

A few nights later, they meet Deborah’s boss Nancy and her husband, Ted, at a restaurant in Queens. Nancy and Ted are the bores Sebastian had suspected they would be at the restaurant. Ted, a man in his late forties, is stiff with boring political chatter. Then there’s Nancy, who wants to talk about nothing but work with Deborah. ‘Fuck. Somebody kill me,’ Sebastian thought and settled in for a long night with Deborah’s friends.

Suddenly, Deborah reaches for something on the table and knocks Ted’s beer into his lap.

“Oh, crap,” Ted roared, pushing himself back in the chair while rubbing at his groin.

The beer soaks Ted’s pants, and Deborah grabs her napkin and starts trying to dry him, rubbing it over his groin.

Nancy then half-jokingly quips, “Great, Ted, now you’ll have to take off your pants.”

Deborah purrs playfully at this insolent comment, especially when he starts doing just that in the restaurant. The women laugh as Ted acts as if he’s going to take his

pants off. Sebastian can’t see what’s happening as he’s sitting on the opposite side of the table. Unknown to him, Ted manages to undo his pants and pull them down enough to flash his big cock at Deborah’s staring eyes.

“TED!” Nancy suddenly said with an insolent grin. “You’ll get us arrested.”

Ted grins and hurries forward to hide his exposed cock beneath the table. However, he doesn’t put it away. Deborah shakes her head and chuckles as she didn’t expect Ted to be so naughty.

“Your husband is a lark, Nancy,” Deborah said, slipping her hand under the table into Ted’s lap to feel the impressive black cock. She can feel its thickness and veins.

“Oh yeah, you can’t take him anywhere,” Nancy said, rolling her eyes. “He’s quite a handful.”

The women laugh knowingly as Ted’s black cock grows in Deborah’s stroking hand, and the balding man’s grin grows wider.

“That’s why I married a lawyer,” Ted said, enjoying the grope. “To keep me out of trouble.”

“It’s a big brief, that’s for sure,” Deborah said, and Nancy laughed.

“So, Nancy,” Sebastian said, not knowing what was happening. “Deborah told me you might be sponsoring her to study for her law degree.”

Her eyes practically shine. “Deborah has a natural talent when it comes to law. Don’t you think so, Ted?” Ted grunts. “I like her hands-on approach,” he said.

Then to Sebastian, he said, “Nancy can’t stop talking about Deborah’s talent at work. You’re a lucky man to have a woman like her.”

Deborah’s mouth grows tight. She sits so Sebastian can’t see her giving Ted a handjob under the table. “Really?” she asks wide-eyed. “That’s nice. But I’m still thinking about it. I have my hands full at the moment.”

“I think you should do it, honey,” Sebastian encouraged Deborah. “But only if you want to, of course.”

“Oh yeah, Deb,” Nancy said, leaning across the table and speaking in a harsh whisper. Her movement also distracts Sebastian from seeing Deborah and Ted’s intimate

moment. “Only if you want to, but I think you have a good grip on the opportunity.”

A hungry, sexy look crosses Deborah’s face. “I can barely get a grip on it,” she said softly and chuckled.

“How did you and Ted meet?” Sebastian asks, trying to make sense of the conversation.

Nancy chuckles. “I met him in college. He was streaking at the time as part of some fraternity prank. The first thing I saw was his massive cock.”

Deborah laughs. “Oh, he is a naughty man.”

“Oh, it was love at first sight. Ted would be naked all the time if he could. He loves to show his wang off,” Nancy said.

“I can tell. Sebastian would never let anyone see him naked for the opposite reason.”

The women laugh heartily, and Sebastian blushes every shade of red. There’s a visible sweat line on his forehead, and he grimaces, feeling lightheaded at the sound of the women laughing. Add to this the smugness from Ted, and Sebastian feels his stomach drop. By Nancy pointing out her husband wouldn’t be embarrassed to be naked in

public because he has a big black cock, Deborah just shamed him by implying he would be embarrassed because of his small dick. Ted suddenly lurches forward and grunts as his cock climaxes under the table. Deborah’s hand suddenly appears, and she starts licking her fingers.

“The food here is tasty,” she said to Nancy. “I love the sauce.”

Her hand disappears, then returns to her mouth for more sucking and licking of her fingers.

“There’s more where that came from if you want?” Nancy said.

“We’ll see,” Deborah said with a wink.

Sebastian feels uncomfortable for the rest of the evening, thinking Deborah ousted him to her boss about his small penis size. He can’t seem to concentrate on anything. The conversation is echoing around him, and he feels isolated from it. He hears them laughing and thinks it’s about him. His thoughts are muddled. ‘This can’t be happening,’ he thought.

Eventually, Deborah takes his hand and asks, “Are you OK, Sebastian?”

He forces a smile. “I’m OK,” he said. “I have a bit of a headache coming on.”

“Oh, poor dear,” Nancy mothers him. “I have some Tylenol in my purse.”

As she grabbed some tablets for Sebastian, Ted said, “Sorry if all this legal talk is boring you, Sebastian.”

“Oh, that’s OK,” Sebastian said, taking the pills and downing them. “Thanks, Nancy.”

“No problems, young man. Deborah tells me you’re a keeper.”

“Thanks.”

“Tell us about your crypto investments,” Ted asks. “I keep hearing it’s an extremely volatile market.”

So, the conversation rambles along, and Sebastian feels more comfortable by the night’s end. But the knowledge Deborah shamed him in front of these people burns deeply. He again feels his inadequacy burning in his loins. A feeling that’s happening more and more lately. Worst of all, he’s starting to have thoughts he hasn’t had in years.

*****

Over some time, he wants to feel the feminine comfort he felt as a teenager. He shaves his legs and body of any hair one day. It makes him feel better. Then before he knows it, he’s staring into Deborah’s panty drawer, picking out his favorite ones and trying them on. The soft material makes his little dick hard and wet, and he jerks off in them, careful not to stain the panties themselves. After an intense orgasm, he feels guilty because he promised Deborah he wasn’t into crossdressing anymore. He quickly put everything away to hide his secret but would soon be wishing he could wear them all the time.

However, Deborah had set up teddy bears with nanny cams in them and saw everything he did. It disgusted her that he would use her undergarments in such a way, but the fact that Sebastian was mentally unwinding aroused her. A new dating dynamic has developed between them. She starts to openly comment about other men in front of him with her friends. Jokes coated with confusing sweetness at his expense. This drives his tingling sense of inadequacy as a man, leading to him wearing her panties, bras, and stockings when Deborah isn’t home.

After doing this for a few months, Deborah decides to see how far she can emasculate him before making his crossdressing public.

*****

Deborah felt a surge of power as she realized just how much of a wimp Sebastian turned out to be as she watched the videos of him crossdressing in her underwear and jerking off his tiny dick. She knows she’s dealing with a small dick sissy. She noticed he had confidence problems and could make him do anything. Deborah had underestimated how quickly her manipulations would cause Sebastian to fall. She felt a little sorry for him but laughed hard that she got him to dress in panties so quickly. Now she’s ready to take control. She has plans for Sebastian, a coming out of sorts.

To get him in a vulnerable moment, she decided to catch him in the act of wearing her underthings. She had determined from the nanny cams that he often did it about midday when she was at work. So, the day came when she came home to catch him, knowing he’d be so embarrassed that he’d let her emasculate him in the worst possible way.

She enters the bedroom to find him in some recently bought black lingerie. He has it all on. The lacey thong and bra, and her thigh-high stockings.

“SEBASTIAN,” she screams. “You dirty little pervert.”

His face goes red, and he tries to cover his tiny boner with his hands. “Deb? Deb, what are you doing home?”

“That doesn’t matter,” she said. “Why are you wearing my lingerie, you dirty little pervert? You told me you didn’t do this shit anymore.”

“But honey—” he begins.

“You think I don’t know about your little adventures in my drawers,” Deborah said, rolling her eyes. “What do you do with them? Do you jerk off in my panties? Are you wearing my stockings? I keep finding runs in them. Is that you?”

His shoulders sag, and he stares guiltily down at the floor.

Deborah laughs coldly. “It is you. Are you gay?”

He gazes up at her, his cheeks red. “No, I’m not gay. I just like—”

“You like what? Dressing up like a girl?”

Sebastian tries to explain it away, but it’s useless. She kneels in front of him to look closely at his outfit. “Do you have any more secrets like this? Have you been wearing my dresses too?”

“Um, no.”

She grabs his dick and starts stroking it in her panties. “Don’t lie to me anymore,” Deborah said hotly, feeling his dick grow hard. “Anyway, it seems these clothes have a terrible effect on you. I have never seen your little dicklette so hard.”

Deborah’s right. Sebastian’s dick is as hard as it can be and stands proudly at four inches and as thick as a finger. His head is red and leaking pre-cum, and the smooth white shaft throbs with every stroke. She lets go of his small dick because he may blow at any time, and Deborah has more in mind than just giving him a quick tug. The woman grabs him forcefully by the chin and pulls Sebastian close. Her blue eyes are cold and steely, and her voice is harsh.

“Do you use my lipstick too? My blush?” her words are like accusations.

No, no, honey. I swear,” Sebastian squeaks, emasculated by the power of her womanhood.

“No matter,” she said and suddenly smiled. “What if you just finish off your face like a girl? That might be fun.”

Deborah grabs his hand and leads a reluctant Sebastian into the bathroom. The man feels a tingling sweep up the back of his neck and across his face. His chest goes tight as his cheeks burn hot. He wants to fight this as he can’t make sense of Deborah’s sudden behavior change.

“OK, sit,” Deborah said, pointing to a chair. “Time to do your makeup.”

Deborah decides to block out Sebastian’s eyebrows. It’s a simple enough but time-consuming process using Pritt-Stick and foundation. The skillful part is drawing on Sebastian’s new eyebrows. Deborah does an excellent job of penciling on the thin, feminine arches. Deborah gives Sebastian full foundation, even brushing his ears. She carefully and expertly applies the rest of Sebastian’s makeup.

Deborah does a fantastic job on Sebastian’s eyes. She also applies blush. The power of contouring makes

Sebastian’s face, especially his nose, appear a lot more feminine and changes the shape of his face. The lipstick and gloss are a sensual shade of red. She eventually steps back and admires his work.

“That looks good,” she said with a smile.

“If you say so,” Sebastian said, blushing. He does like it, though.

She grabs a bottle of nail polish. “OK, hold your hands out,” she orders and quickly coats all ten nails in a similar red to the lipstick. “Blow on them, so the nail polish dries.”

Deborah leaves and returns with a long blonde-haired wig. She goes to Sebastian, puts the wig on him, and makes final adjustments. Deborah says, “Not so bad with this old wig,” as they stare into the mirror. She smirks and adds, “Rather passable for a sissy girl.” Then she laughs.

“Oh, please, honey,” Sebastian squeaks, staring at his female visage in the mirror in wide-eyed shock.

Deborah suddenly turns Sebastian and pushes him against the basin. She sneers at him and grabs his crotch

squeezing it hard. “So what? Don’t you enjoy this crap? Don’t you want to please me?”

He can feel his dick getting hard again. “Ooh, yes, I do.”

“Then shut the fuck up and obey me,” she shouts. “Bring me my ‘fuck-me’ pumps.”

Stepping aside, Sebastian runs to the bedroom and gets the shoes. When he returns, Deborah is sitting on the chair. She says, “On your knees, sissy girl.”

Sebastian kneels and starts to put on the pumps. His mind is racing about this change to his girlfriend.

“Hmm, what a pretty slut you are,” Deborah mocks as she watches him.

“I’m not a—”

“Didn’t I say shut up?” Deborah shouts. “Now finish my shoes. I might dress you like this more often. It suits you.”

They go back into the bedroom, and Deborah sits while Sebastian stands shivering at this new side he’s witnessing to Deborah. She spreads her legs to reveal her shaved pussy, her labia are reddish and swollen, and her slit glistens with vaginal slime. The waft of her heat fills the

room with its tangy scent, and as her legs spread, her pussy lips unstick, revealing her inner flesh and making her vagina gape.

She gazes at him with a sultry disposition and says, “Please me with your tongue, sissy slut.”

Sebastian kneels, delves between her thighs, and licks her pussy slit and clit. Her clit is hard, poking through the hood. She smells musky as Sebastian licks her from asshole to clit with long licks. Deborah almost screams, pulling her legs together, while Sebastian locks his lips around her clit and sucks instinctively.

“Easy, slut. Take it slow,” Deborah moans. “Very slow.”

She thrashes on the bed as Sebastian works just the tip of his finger into her cunt. He fingers her as her muscles spasm around them. His tongue flicked light and fast over her clit. Deborah loved it. Her hips move with Sebastian’s motions as she rides out a release. Deborah pants, her heart pounds, and her pussy flushes with moistened heat. The tingle in her pussy was overwhelming as she felt Sebastian’s tongue probe every part.

“Ha. You eat pussy like a girl,” Deborah teases. “So you might as well look like one while you do it, slut.” Suddenly, she pushes Sebastian away and gets to her feet. Gazing back at him with a mischievous smile, she says, “Come on, sissy. Eat my ass too.”

Sebastian slides his tongue into her butt crack, tasting her nutty ass flavors, and licks heartily at her shitter.

“Yes. Go on, bitch,” Deborah moans.

After she’s had enough of him rimming her and poking his tongue into her shitter, Deborah gets back on the bed, and Sebastian dives between her legs and starts sucking on clit and finger-banging her cunt. She shudders and groans, her chest rocking tightly as her body blasts into the most powerful, massive orgasm. Deborah arches and gurgles helplessly, overwhelmed by the sheets of crackling sexual lightning tearing through her body. The woman’s stunned, shocked at the mighty strength of the furious, howling sexual cataclysm that rocks her body. She trembles and quivers. Her ass is humping back against his face urging Sebastian to devour her pussy.

Eventually, the orgasm fades, and she pushes Sebastian’s head away. The man decides it’s time to have a turn and starts to climb on top of her while freeing his hard dick. Deborah opens her eyes and realizes what he wants.

“What do you think you’re doing?” Deborah asks harshly, making Sebastian stop and grimace.

He lowers his head and says softly, “I thought we could—”

“What? Make love?” Deborah said mockingly.

He nods. Deborah laughs, puts her foot in Sebastian’s groin, and uses it to rub his boner back in the panties.

“Oh, I see. The poor little sissy girl is all excited?” Deborah asks with a smirk. “Do you think I’d let a male dressed as a sissy slut fuck me? You can go finish yourself in the toilet if you want.”

Sebastian gasps.

Deborah adds, “And don’t make a mess in my panties. They’ll still be suitable for next time.

He stares at her bewildered. “But you’re not serious, right?” he groans.

“Just consider yourself lucky I’m letting you cum, bitch.”

Sebastian cuddles her leg, staring at her delicious pussy. “OK, I’ll do what you want.”

Deborah grabs Sebastian’s wig and pulls his head back sharply. Deborah glares at her sissy boyfriend and says coldly, “Oh, you will, eh? Now I’ve seen what a slut you can be. You will if you ever want to touch me again.”

He nods glumly.

“But from now on, we’ll be doing things my way. If you ever want to cum again,” she shouts as Sebastian goes to the bathroom to jerk off.

He gazes over his shoulder and says, “Yes, Deborah.”

Chapter 4

The following day Sebastian finds his beautiful girlfriend sitting in the living room, drinking a glass of wine, and listening to music when he gets home from some investment meetings.

“Hi, babe,” he said and bent to give her a soft kiss on the cheek.

Deborah smirks at him and says, “How’s my sissy bitch today?”

“Oh, Deborah,” he groans, blushing. “Can’t we move on from last night? I promise I won’t ever do it again.”

She laughs coldly. “Not a chance, bitch,” she said. Then she grabs a white box with a pink ribbon and hands it to Sebastian.

“Open it,” she urges.
“What is it?” he asks, shaking the box.
She rolls her eyes. “Open it and find out, silly.” Sebastian opens the box. He pulls away the tissue paper

to reveal a front fastening underwired bra, no padding, made of a decorative floral embroidery and satin fabric. It’s a matching bra and thong set with an adjustable suspender belt and leg straps. The material is see-through, and the floral embroidery is pink and purple. She sees him staring at the lingerie wide-eyed and shaking his head some. It doesn’t take him long to feel he’d opened pandora’s box. It seems Deborah is now ready to exploit his secrets fully.

“Do you like it?” Deborah asks, grinning.

“Um, I didn’t expect this,” he mumbles.

“Why don’t you be a good little sissy and go and try it on. I mean with your wig too. I wanna see the whole effect.” Sebastian takes the box upstairs to their bedroom and starts undressing from his suit. The man is worried that

things might be spiraling out of control since Deborah discovered his crossdressing secret last night. However, despite his reservations, Sebastian gets into his feminine underthings. He stares at himself in the mirror and gasps when he sees all his masculinity dissolve before his eyes. He hears a noise at the door and sees Deborah standing there, drink in hand, and smirking. She sachets into the bathroom with such silent sensuality that it arouses Sebastian.

“Well, it suits you perfectly,” Deborah said lushly, drinking him in with her eyes.

Sebastian gazes down at the floor and sighs, making Deborah raise an eyebrow in disapproval.

“Don’t you like it?” she asks. “Yes, but—” Sebastian begins.

“Don’t be silly,” Deborah said over him. “But I have another surprise for you. A treat.”

“Oh, what?”

“One of the girls at work has been going on and on about this comedy boat tour on the Hudson River,” she said. “I want us to go.”

“OK,” Sebastian said.

“I want you to go down tomorrow and buy tickets for this weekend for Melanie, Sarah, Nancy, Ted, and us.”

“I have a busy day tomorrow,” he said with a frown.

“Come on,” she said with a sneer. “You have plenty of time to dress in my underwear and jerk off all day, so you have time to do this.”

He sighs. “OK.”
*****
The following day, he goes to a harbor and buys the

tickets for the boat tour. The black woman behind the glass seemed surprised he wanted tickets, but Sebastian was too preoccupied with his problems to notice. Deborah was pleased to see the boat tour tickets on the hallway

table and rewarded Sebastian by buying him some more lingerie to wear.

When Saturday night arrives, they go down to a dock on the Hudson River to meet Deborah’s friends at eight PM. He hadn’t met Melanie or Sarah before and was surprised to find they were African American like Nancy and Ted King. As they approached the boat to board it, he couldn’t help but notice that he and Deborah were the only white people.

“You never told me this was a tour for black people?” he whispers to Deborah.

She turns and frowns at him. “You got a problem with black people?”

He grimaces, immediately worrying someone heard her. “No. No, of course not,” he said, blushing. “I would have liked a heads up, that’s all.”

The black men are especially intimidating for Sebastian, and he feels his balls tingle in the lacy panties he’s wearing.

Deborah chuckles. “Honey, don’t get your panties in a bunch. You came down here to buy the tickets. Didn’t you

see all these posters advertising the tour as a black comedy boat tour?”

He shrugs. “I admit I was too busy watching the exchange on my phone to notice,” he said glumly.

“Well, suck it up. This is going to be a lot of fun.”

She watches him go pale and knows he doesn’t think she’s right. He seems to shrink before her eyes, and Deborah decides she will have fun seeing him suffer for the next six hours.

*****

The partygoers are split into two groups. One will watch the comedy show, while the other spends time at a dance club on a lower level of the boat. There’s also a bar there, and Deborah tells him he’s been chosen to go down during the comedy show to get refills for everyone. So, they settle in to watch the first stand-up comedian, Latisha Lash, a black woman. The set is going well, and Deborah notices Sebastian has relaxed and enjoys the jokes.

Latisha suddenly asks the audience, “Are there any brave white people here tonight?”

Deborah and Sebastian raise their hands and a couple of others too, but there are few.

“Damn, it's not cuckold night tonight. White girls are bringing their small dick white boys here to lure our fine black men away,” Latisha cracks, and the audience laughs. “Just look at this white boy,” she said, pointing to Sebastian. “I can tell just by looking at him that he's got a dick the size of my pinky finger.”

The audience bursts out laughing as Latisha holds her pinky finger aloft.

“Stand up, white boy. Come on, stand up and be proud of your little dick heritage.”

Deborah elbows Sebastian in the side, saying, “Stand up. It's just a bit of fun.”

Sebastian forces a smile as he stands on shaky legs. A spotlight is shone on him, and the large woman on the stage takes in his small frame. Everyone can see Latisha’s mind is turning.

“Is that your girlfriend?” Latisha asks. Sebastian nods. “Well, not for much longer anyway. Cos, honey, once she goes black, your mother fucking baby dick will feel like a

hot dog in a hallway. All you gonna hear from her after tonight is, ‘Is it in yet? Is it in yet?’ That black motherfucking cock is gonna take her to places your white widdle diddle could never. Amirite? Amirite?”

The audience is laughing hysterically, and while Sebastian forces a smile, his face is red. The only thing is the bright spotlight makes him look pale, so no one notices his blushing except for Deborah, and the humiliation is making her wet.

“What’s your name, honey?” Latisha asks. “Sebastian,” he shouts,
“Well, thanks for being a good sport,” she said. “Just

remember it’s not the size that matters—Oh, who am I fucking kidding, the size always matters. No woman wants to fuck a guy with a small dick. Amirite, ladies? Fuck that shit.”

The women start cheering as Sebastian sits and sees Deborah is applauding too. He immediately pouts. Deborah grabs his hand and says, “Oh, don’t take it so personally. Why don’t you go downstairs to the bar and

get us some drinks? Latisha should be off the stage by the time you get back.”

He nods and sneaks out before Latisha unleashes on him again. As he refills the drinks, Sebastian realizes that the dance area downstairs is like a full-on hip-hop club, and the men are big and intimidating. He gets loads of nasty looks and shoves and bumps as the only white man there. But he manages to get to the bar and orders another round of drinks. The bartender puts the glasses on a tray, and Sebastian takes the drinks back upstairs to the comedy club.

As he enters the comedy club and makes his way to the table Deborah and her friends are sitting at, the light shines on him again. Then he hears a male comedian say, “Oh, look. Shrimp dick is back.”

The audience laughs. The black man on stage is a legendary local comic called Will Prior.

“He took so long to get drinks cos he needed to go to the toilet first. It takes a while to find a dick that small,” Prior said. “You need to sprinkle some pepper on it, and when it

pops out to sneeze, you gotta grab that motherfucker. Isn’t that right, shrimp dick?”

Sebastian smiles, “You seem to know all about it.”

The audience ‘oooooh’s’ at Sebastian’s comeback. Prior smiles. It’s all part of his plan.

“Oh, I’m only going by what your girlfriend Deborah told us while you were outside,” he said with a wink. “She told us your dick is so small the police filed it as a missing person. Deborah said your dick is so small that when you got circumcised, they used an electron microscope. Your dick is so small you could fuck a pasta strainer.”

The audience is again in hysterics. Sebastian shakes his head in that ‘yeah, yeah’ way with a fake smile to show he can take it. However, Deborah knows he’s nearly at breaking point already, which arouses her. Then Prior moves on to something else, and Sebastian is left alone for a time. Every comedian's comedy section of their night seems to go like this. Each time Sebastian goes for drinks, he gets the stink eye in the dance club, followed by whatever comedian is on stage doing their set ragging on him for having a small dick.

At some stage, he goes to the toilet and locks himself in a cubicle for half an hour to escape the scathing comments. As he came out, a black man said, “Did you find it this time, shrimp dick?” and laughed.

“Very funny,” Sebastian said coldly.

Eventually, he waits for Deborah and her friends outside the comedy room and is happy when the show is finally over. Deborah comes out and frowns at him. “Where have you been?” she asks.

“I needed some fresh air,” he said, brushing it off. “You’re not upset by what they said?”
He sighs. “What’s the point of being upset about it,” he

said glumly.
Ted slaps him on the back with a big grin on his face. “I

thought you were such a good sport in there. Don’t take it to heart. They probably do the same to every white guy on this trip.”

Nancy chimed in, “Yeah, fuck what they say, Sebastian. Now, let’s go dancing.”

*****

Deborah loves dancing. She’s often the first to get up and boogie to the music, encouraging others to join her because she’s a sexy woman. Sebastian has grown to love how she dances with different men and sometimes women and flirts with them and wraps them around her little finger. Knowing other men find her attractive and sexy gives him pride that she goes home with him at the night’s end. The others in the hip-hop nightclub on this boat tour find the curvy brunette attractive.

Sebastian doesn't like places like this, but he likes seeing her happy and enjoys watching her dance. Therefore, he stands back as Deborah goes to the dance floor with her friends and starts dancing most sensually. It isn’t long before several black men dance around her, trying to get her attention. She dances through several songs and returns to Sebastian to have a drink.

“You seem very popular here,” Sebastian said with a slight sneer.

“Oh, I bet it gets your little clit hard thinking of those men lusting after me,” Deborah whispers.

She smiles as she watches him gasp and decides tonight is the night to push him beyond anything she’s done to him before. Once she’s finished her drink, Deborah’s back dancing again. Several times Sebastian is sure he can see her black lacy panties when her dress flips, and he finds it exciting to watch. A guy gets a bit too aggressive in touching Deborah, and before Sebastian can react, a huge man, a bouncer, is on the stranger dragging him off the dancefloor. He was standing with Ted when it happened.

“You know, if you dance with her, maybe that wouldn’t happen,” Ted said, drinking a beer.

“I hate dancing,” Sebastian said with a shrug. “I prefer to watch.”

“One of these days, a man will sweep her off her feet on the dance floor. What will you do then? Just watch?”

Sebastian laughs. “She wouldn’t have the guts to do that,” he said.

The bouncer returns and speaks with Deborah. She’s whispering in the big black man’s ear, and he’s nodding. Then she points toward Sebastian, and the bouncer sees him and nods.

‘I wonder what that’s all about?’ Sebastian thought. *****
Not long after, Deborah watches Sebastian walk to the

bar to get another drink. She goes to the bouncer again and whispers seductively in his ear. “If you can give my boyfriend a hard time, I could give you a good time,” she said.

The bouncer’s name on his badge is Whale, a nickname due to his size. He’s a big man. The barrel chest of a weightlifter, with arms and legs like tree trunks. His bald head shines with a light sheen of sweat. His pants bulge with what can only be a python of a cock. Whale frowns, considering Deborah’s offer.

“Why? Is he roughing you up or something?” Whale asks with a deep frown.

“No, he’s a wimp with a tiny white dick,” Deborah said and smiled. “I wanna see how far I can break him.”

“Oh, you’re one of them, eh? OK, but you owe me some sweet pussy if I do it.”

“If you can make him do something so nasty, so out of character for him, you’ve got a deal.”

“Challenge accepted.”

She smiles as she watches the hulk of a man. Her friend Sarah is nearby and takes her arm. Sarah asks with a grin, “What are you up to?”

“Oh, I’m just playing a game with Sebastian,” she said, worried her friends might think she’s a bitch. “Don’t worry. We do this all the time. It spices up our sex life.”

Sarah laughs. “You go, girl,” she said, and they returned to the dance floor.

However, Sarah keeps an eye on her sissy boyfriend, wondering how much more he can take before he cracks.

*****

As Sebastian is buying a drink, some woman bumps into him. Then her eyes bulged, and she slapped his face hard. He drops his beer, and the bottle shatters, sending beer and glass everywhere. He’s stunned, rubbing his cheek because it stings.

“You dirty pervert,” the woman screams.
People stop and stare.
“What? What did I do?” Sebastian said, still rubbing his

red cheek.

“I felt you grope me, you pig.”

Then Whale steps in and pushes the woman away from Sebastian. “Come on, you two. Break it up. What’s going on here?”

Before Sebastian could speak, the woman said, “This creep put his hand under my dress and fingered me.”

“I did not,” Sebastian said wide-eyed. “It must’ve been someone else, but it wasn’t me.”

The bouncer seems unimpressed and grabs Sebastian roughly. Over on the dancefloor, Deborah laughs but distracts her friends so they don’t see what’s happening.

“You better come with me,” Whale said. “I think you need a time out.”

As several bouncers push the diminutive white man out of the nightclub, Sebastian decries his innocence the whole time. They force him to the bow of the ferry-like boat. The air is brisk and chilly outside as the New York City skyline rolls past each side. You cannot hear the music or the comedians out there, just the breeze and the chug of the diesel engines.

“Stop you’re whining, white boy,” Whale eventually said, and Sebastian fell quiet. “Now, that woman says she’s going to press charges. She said you put your finger inside her pussy. What you say to that?”

“I promise, I didn’t do it,” Sebastian said, wringing his hands. “I had my back to her when she ran into me. I swear.”

“She’s pretty sure it was you,” another big man said. “We just might let the cops sort it out.”

Sebastian gasps. “No, no, please. It wasn’t me.”
“It’s not our problem,” Whale said dismissively.
“Hey, aren’t you the guy all the comedians were ragging

on?” the other black man said.
“What are you talking about, Willis?”
But another guy butts in, saying, “Yeah, they were

dissing some white guy calling him ‘shrimp dick.’ Latisha told me she knew it was true cos of the way he reacted.”

The three Black bouncers chuckle, and Sebastian blushes deeply. Those feelings of inadequacy tingle again in his tiny balls and radiate throughout his body.

“Is that right?” Whale said, eyeing Sebastian mischievously. “Have you got a shrimp dick?” he asks Sebastian.

“What has that got to do with anything?” Sebastian said with a pout.

“Well, groping a woman in public takes big cock energy,” Whale explains. “If you got a tiny dick, we’ll know it wasn’t you.”

“Yeah, show us your dick, dawg,” Willis said and smiled at his friends.

“I’m not showing you anything,” Sebastian snaps, suddenly feeling the night air’s chill.

The other black man with ‘Mikey’ on his badge shouts, “If you prove to us you’re a small dick beta wimp, then we’ll tell that chick we checked the footage, and it wasn’t you.”

“Why don’t you do that anyway?”

Whale rolls his eyes. “Cos we have no fucking footage, you moron. But she’ll believe us if we tell her that, and you won’t have the hassle of explaining it all to the cops when we reach the shore.”

“No, I will not. I’m innocent,” Sebastian said, shivering.

Mikey steps closer with a deep frown. “Don’t make us take them off for you,” he growls. “You won’t like that.”

Sebastian cowers. Stepping back, his butt hits the railing of the boat. He turns sharply to see the bow breaking through the choppy, cold water. He has nowhere to go. He undoes his pants and pulls them down to his ankles with a deep sigh. The bouncer called Whale has his phone out and starts the flashlight app, shining the light at Sebastian’s groin.

“Shit, are you wearing women’s underwear?” Mikey said wide-eyed.

Sebastian hangs his head. He doesn’t want to answer as shame courses through him. The material’s transparency makes it plain to see he has a tiny dick. The cold night air rushing by causes it to shrink to the point where it’s become an inny.

“I don’t think he has a dick,” Willis said, peering closely.

“Jesus, how the fuck does a bitch like you get a woman like Deborah?” Whale asks.

“He’s not just a beta wimp,” Mikey said sharply. “He’s a sissy bitch as well.”

“I guess you’ve verified your story,” Whale said, taking pictures. “No small dick sissy bitch is going to grope a woman. He’d be too timid for such a thing. Groping is what alpha men do.”

“I need more proof,” Willis said.
Sebastian’s eyes bulge. “What?” he asks.
Willis unceremoniously undoes his pants and pulls them

down to his lower thighs and his underwear. The coldness of the outside air causes their breath to fog. Sebastian stares at his exposed black manhood. The cock is semi-hard and already nine inches

long, and very thick. The sissy can see the large veins protruding from the surface. The man is uncircumcised, and drops of pre-cum dribble from the slightly exposed purplish head.

“Suck my cock, bitch,” Willis said. “Then you’re free to go.”

Sebastian is shaking. He feels his dicklette go even further inside his body. “I’m not, ah, gay,” he said weakly.

“No, you’re a sissy. Having you suck my cock is the same as if a chick did it.” Willis grabs it with his hand and shakes it a bit. “Well, bitch, what do you think?” he asks with a sly grin. “I bet you’ve never tasted a real man’s cock before?”

“I don’t suck men’s cocks,” Sebastian said wide-eyed. “Oh, sure you do. Have a taste. See if you like it.” Mikey grabs Sebastian and forces him onto his knees in

front of Willis’s superior cock. Sebastian hesitates as his nostrils fill with Willis’s manly musk. He could refuse to suck it and then complain to the cops later. This is rape, but it would be his word against theirs, which never goes well.

“Oh, what the hell,” he finally said.

He took the bouncer’s cock in his fingers and rubbed it. Bending, Sebastian lowers his head to the black cock and opens his mouth. However, before his tongue could have a lick, Willis stops him.

“You have to say the words, bitch. Tell me what you want.”

Staring into Willis’s big brown eyes, Sebastian whispers, “I wanna taste your cock. I wanna suck on it,” and his tongue snakes out to lick the head.

‘Not bad,’ thought Sebastian on the first lick. Sebastian works his tongue into the pee slit and licks around the large head. The aroma of this black bouncer’s groin is pungent. Sebastian cradles Willis’s loose balls with his free hand and yanks the shaft with the other. The sissy’s lips caressed the smooth head and then gracefully engulfed it. Willis moans, so sensitive to Sebastian’s attentive touch.

Soon, Sebastian took this unfamiliar black cock deep in his throat, bobbing and working his saliva-coated shaft. For a full ten minutes on the bow of the tour boat, as the New York City surrounds them, Sebastian sucks and pulls, strokes and kisses, pumps and worships the giant joystick of the black bouncer. He’s physically pleading with the cock to drain itself into his warm mouth without complaining.

Sebastian taps the cock on his outstretched tongue and then, without warning, overwhelms Willis by taking the massive phallus down his throat. The feel of the cock flesh against his throat was exquisite. Sebastian drools as the arousal surges through him. Wrapping his left hand around the shaft and tickling Willis’s hairy sack with his right, he jerks the black cock boldly, wanting Willis’s semen and enjoying the effort to achieve it.

Sebastian gazes up at Willis’s face for a moment and, in a breathless voice, says, “I don’t want you making a mess on my clothes, so you’ll have to let me know when you’re gonna cum, OK?”

“It won’t be long now,” Willis moans.

Sebastian licks his lips and stuffs the big black cock deep in his mouth and throat. Willis’s big throbbing cock begins shooting burst after burst of thick pasty semen into Sebastian’s mouth. The sissy accepts the black man’s wet orgasm and swallows the molasses-like evidence happily without losing a single drop. His clitty dick is hard. Sebastian soaks his panties with pre-cum as the thick semen propels down his gullet.

Sebastian comes up for air. “Thanks for not making a mess on me,” he said.

“Sissy bitches always give great head,” Willis said, putting his cock and balls away in his pants.

“Fuck, look at his boner,” Whale said. “My pinkie finger is bigger.”

Mikey laughs. “Stand up, bitch. We want pictures of it. Pull those panties down at the front so we can see it—balls and all.”

“Just as well he shaves. He wouldn’t be able to find it otherwise,” Willis said. “Do you guys wanna blowjob too?” “Nah, we’ve wasted too much time on this loser already,”

Whale said, and Mikey agreed.
After taking many photos, Sebastian is finally allowed to

pull his pants up again, and they leave him alone, promising they’ll sort it all out with the black woman. He turns and grabs the rail and stares at the New York City views rolling past. ‘What the fuck have I done?’ Sebastian wonders.

Chapter 5

When the boat finally pulls into the harbor again, Deborah can’t find Sebastian anywhere as the revelers are leaving the ship to head to the nearest bars and clubs to continue their night. After searching for Sebastian on the other side of the tour boat, Ted and Nancy come to her with glum faces.

“Can’t find him anywhere,” Nancy said with a shrug.

“I checked the bathrooms too. He’s not there,” Ted added.

Sarah and Melanie arrive with the bouncer called Whale. Melanie said, “Whale saw him leave.”

Deborah takes the black bouncer by the arm and pulls him away to speak to him without the other’s hearing. “What did you guys do to him?” she asks with a raised eyebrow.

Whale chuckles. He pulls out his phone and shows Deborah the pictures he took of Sebastian’s tiny boner. “We exposed his little secret,” the man said in his baritone voice.

Behind them, a female voice shouts, “Oh my god, is that a kid’s dick?”

It was Sarah, staring wide-eyed at the phone screen.

“No,” Whale said, shaking his head. “It was some guy we had here.” He hands Sarah the phone while smirking at Deborah.

“Fuck, that’s such a tiny dick to be on a grown man,” Sarah said, showing Melanie.

Ted and Nancy look at it too. “White men and their tiny dicks,” Ted said, shaking his head.

“Was he wearing women’s underwear?” Nancy asks, handing the phone back to Whale.

“Yeah, he was a sissy wimp,” the bouncer said. Then gazing at Sarah said, “I have no idea how his girlfriend put up with it.”

“He had a girlfriend?” Sarah asks wide-eyed.

Whale nods and, still gazing at Deborah, says, “A fucking hot girlfriend. I wanted to bone her too.”

Melanie sneers. “He must have money. No woman would waste her time on a dick like that. He deserves to be pussy free for life.”

Deborah is getting horny listening to the others insult the guy with the little dick, knowing it was a picture of Sebastian’s dick. She knows he must’ve gotten off the tour boat as soon as it docked. No doubt embarrassed and humiliated by what the bouncers did to him. But she has to keep playing her game.

“You said you saw my boyfriend leave?” Deborah asks. Whale nods. “He was the first one off the boat.” Nancy said, “You’ve been stood up, Deb. Did you two

fight tonight?”
Deborah shrugs. “He was a gloomy Gus after those

comedians picked on him.”
Sarah stifles a laugh. “They should’ve picked on the guy

in that photo instead,” she said. “He was the real shrimp dick on the boat.”

“Oh my God, right?” Melanie adds, doing the small dick sign.

Deborah ignores the comments. “Can you guys give me a ride back to West Village,” she asks her friends. “I’ll never get a cab at this hour.”

“We’ll have to squeeze you in,” Nancy said. “We brought Sarah and Melanie, remember.”

Suddenly, Whale said, “I’m going to West Village. I can give you a lift if you’d like.”

“Would you?” Deborah asks the bouncer. She feels her pussy gush.

“Yeah, I don’t mind.”

Deborah turns to her friends and says, “That’s if you all don’t mind. West Village is so out of your way. This is a good solution. Besides, Whale is a good guy.”

It’s agreed, and Deborah says goodbye to her friends and waits for Whale to finish his work. It doesn’t take long before they drive back to Deborah’s place.

*****

Whale puts his hand on her leg in an intimate gesture on the trip.

“What’s your real name?” Deborah asks. “I can’t call you Whale.”

He glances at her with a smile. “My name is Reggie. Can I ask you something, Deb?”

“Is it about why I’m with Sebastian?”

He nods. “It doesn’t make sense to me why a gorgeous woman like you would waste your time on a guy like that. Is he rich or something?”

Deborah smiles. “He is rich, but that’s not why. I don’t need his money.”

“Then why?”

“When I met him, I was lonely, and Sebastian is a nice guy. His dick is small, but he eats pussy well.”

“Typical,” Reggie eventually said. “Losers like him can’t make a woman cum with their tiny dicks, so they have to eat cunt instead. They’re not men at all. They’re bottom feeders. How long have you been together?”

She frowns. “Eight months, maybe a bit longer.”

Reggie shakes his head. “Eight months of just getting your pussy eaten and not pounded would be torture for a woman like you. Unless you’re secretly a lesbian?”

Deborah laughs. “No, I ain’t no lesbian. But I miss a big black cock pounding me until I cum and cum and cum. But when I discovered Sebastian was a sissy, I started trying to push him to go the whole way. I’ve been messing with him ever since.”

“You made him wear that lingerie tonight,” Reggie asks with a raised eyebrow.

“Hardly. Oh, Sebastian thinks I did, but it took little pressure. I want to make him go the whole way, though. Dress entirely as a woman. Then I’ll know I’ve broken him for good before I dump him.”

“You’re nasty. I like that. I can help you with Sebastian,” Reggie said with a smirk.

“Oh, how?”

Reggie is silent for a moment. “Before I answer,” he eventually said. “Are we going to fuck tonight?”

“Yes,” Deborah said softly, feeling her heat rise substantially.

“Good. It’s time you got some proper cock in that cunt of yours,” he said. “OK, when we get to your place, let’s make Sebastian’s worst nightmares come true.”

“God, I’m so hot right now,” Deborah groans.
*****
“This is going to be fun,” Deborah said to Reggie as she

pounded on the front door to the apartment. “Open the door, bitch,” she shouts.

“But err, honey, I’m about to go to bed,” Sebastian calls out, wondering why she doesn’t use her key.

“Do you mean you’re naked?”
“No, I’m dressed,” Sebastian said.
Deborah shouts, “So open the fucking door. We’re

thirsty.”
Sebastian opens the door. “Deb, I’m sorry I ditched you

at the boat,” he said, head bowed.
Reggie smiled and said, “Hey, shrimp dick. I bet you

didn’t expect to see me again.”
Sebastian’s head pops up. His eyes bulged, and he

gasped as he saw the big bouncer from the boat. Deborah laughed as they entered the apartment. “Reggie’s been telling me some interesting things about you,” she said to a wide-eyed Sebastian.

“Why did you bring him home?” Sebastian whines. “Do you know what he did to me? I should call the cops and report him.”

“Hey, I never made you suck Willis’s cock. You did that of your own accord,” Reggie said, waving his hand

dismissively. “And you enjoyed it. You swallowed every drop of cum.”

“You dirty little pervert,” Deborah said, waggling her finger at Sebastian. Deborah wraps her arms around Sebastian from behind, slides her hand inside the sissy’s pants, and grabs his dick. Sebastian can smell the alcohol on her breath.

“Oh, yes. He’s got a little boner just talking about it,” she said huskily.

“Please, Deb,” Sebastian begs as he blushes.

“Go and prepare a nightcap for our guest,” she said, releasing him. “And put on some music,” Deborah shouts to Sebastian as he retreats toward the living room.

Reggie admires Sebastian’s sissy form. “Hmm, he’ll look good as a woman,” he said.

Deborah slaps his arm and says, “We’ll see cos tonight’s the night.”

*****

As the two drink the Martini Sebastian made for them in the living room, Deborah makes him strip to his lingerie and dance sexily while they talk and enjoy their drink.

Sebastian had never felt so humiliated, but an inevitable part of him became aroused, showing off like this to Reggie again.

“Go on,” Deborah would shout drunkenly at her husband. “Keep dancing and make it sexy, bitch.”

Not knowing what would come next made Sebastian nervous, but still, he finds himself acting like a whore. Moving sensuously to the music for this man who humiliated him badly on the boat. His little boner was poking into the see-through panties he had on and dribbling pre-cum already.

“Hey, this shit is a bit gay,” Reggie said, shaking his head at the sissy dancing. “I only like women.”

Deborah asks, “Do you want me to dance for you instead?”

“I want you here,” Reggie said. “Can’t you make him dress like a woman for me?”

Sebastian gasps. Deborah gazes at her boyfriend and smirks. “He knows how to do it without my help, don’t you, Sebastian.”

“I, ah, I—” Sebastian begins.

“Shut the fuck up,” Deborah said. “Go to the bedroom and get yourself pretty for our guest. You can wear that pink babydoll nighty I have and the pink panties that go with it. I know you like it.”

Sebastian grimaces and blushes. He asks, “Please, Deb. Why are you doing this to me?”

“You did this to yourself,” she said with a sneer. “One more thing, bitch. Do I have your permission to fuck and suck Reggie tonight?”

Sebastian simultaneously shakes his head and blinks rapidly. He was so confused. One moment Deborah is bossing him around. Now she’s asking for his permission to cheat on him.

“Why are you asking me?

“I told you before I moved in here I would never fuck a black cock unless you gave me permission,” she said coldly. “Now, I’m asking.”

Reggie laughs. “Dang, girl, you’re hardcore,” he said through his chortles.

But Deborah isn’t laughing. She just glares at her pathetic boyfriend. Sebastian is shaking. His boner has gone. “If it’s what you want,” he said red-faced.

“No,” Deborah shouts. “It has to be what you want. Now, say it.”

Sebastian swallows hard. The words he’s about to utter are the most soul-crushing words he’s ever said. “I give you permission to have sex with Reggie,” he said, feeling his balls tingle his utter inadequacy as a male.

Deborah urges, “Why do you give me permission?”

He hesitates, thinking about the answer. But it is all too obvious, even for Sebastian. “I give you permission to have sex with Reggie because my dick is too small to please you like a man’s cock can.”

“Good, boy. Now go get properly dressed for Reggie,” Deborah said, waving him away with her hand, and the sissy left with his head bowed.

*****

Reggie said after he was gone, “That was easier than I thought.”

Deborah snuggles into the big man. “I told you. Sebastian’s my bitch now.”

“After tonight, you’ll be my bitch,” Reggie said and unzipped his fly. “Time you started to kiss me where it counts.”

“Oh, yes,” Deborah moans as she slides her hand inside his pants and pulls out his big meaty black cock.

Reggie’s cock is a masterpiece. Deborah strokes it to hardness and marvels at its size and girth. The man’s circumcised glans is dark and purple and have a perfect helmet shape. Thick veins on the surface twist wickedly, popping out

and pulsating as the man’s blood rushes through them. She places her hands on his thighs and bends to kiss his cockhead. She gently licks the base of his shaft, leaving trails of hot passion where her lips had been. Then slowly moving to the head again.

She did this on the other side and few more times, and after several times she rested when she came to the tip of Reggie’s throbbing black cock. She puts her lips over the

tip, only covering the head, and she can feel the erotic rim of his penis in her mouth. While the head is in her mouth, her tongue dances softly around it while she gently sucks. Reggie’s depositing pre-cum into her mouth as she continues this, arousing her even more. Reggie pulls her dark hair away from her face, admiring her beauty and sensuality as she makes love to him with her mouth.

Deborah slowly takes five inches of the cock inside her mouth, easing down his hard shaft while her tongue twirls in her hot mouth, pleasing him. She softly caresses his balls, which are tight and firm. Reggie moans and tries to hold himself back. However, it’s becoming increasingly difficult not to climax. This is arousing Deborah beyond measure. Reggie starts gently grinding his groin with the rhythm of her oral kisses. She returns to his hard cock, drinking up his pre-cum accumulating while she had been sucking his balls.

As Deborah enjoys the feeling of the massive cock in her mouth, Devin returns wearing the pink babydoll nighty. He has the blonde wig on and is in full makeup. His

fingernails and toenails have pink nail polish, and he’s wearing some white strap-on heels.

“Motherfucker,” Reggie moans. “You do look like a chick.”

He grabs his phone and starts taking pictures of Sebastian. The sissy blushes and whines, “Please don’t take pictures.”

Deborah’s head rose from Reggie’s cock and said, “Shut up, bitch, and do as your told.”

“Turn around and show me your ass, sissy bitch,” Reggie shouts.

Sebastian sighs. He turns, bends, and pulls his pink panties down like an utter slut, exposing his firm, girly butt and the back of his small, shaved balls. He gazes back to see Reggie’s cock still in Deborah’s mouth. The sissy’s eyes bulge as the black cock is so big and as thick as Deborah’s wrist. The brown-haired woman is sucking on the giant black cock with enthusiasm. Reggie’s hands are on Deborah’s breasts, squeezing them.

Deborah peers up at Reggie. She says, “Hmm, it’s been a long time since I had a real cock.”

Sebastian stands stunned, watching his partner’s mouth slide up and down the dark cock. The veins pop out, the head a purplish-brown, and Reggie’s balls gently swing with the motion. And what big balls Reggie has, especially compared to Sebastian’s small grape-sized testes. The sounds of sucking and lip-smacking fill the room as Deborah goes down on this black man with all her worth. After sucking that throbbing mountain of man meat for another fifteen minutes, she turns her gaze to see her useless sissy boyfriend watching.

“What are you looking at?” she asks derisively between licking Reggie’s big black balls.

Sebastian shudders. “The end of us,” he said weakly. “Do a strip tease for our guest. He likes you.”
“Yes, Deborah.”
Reggie suddenly said, “Why don’t you tell your bitch to

stroke it.”
Sebastian feels ashamed seeing his girlfriend acting like

a slut, but he chooses to obey and act like a stripper. The sissy is rock hard, and as he strokes his tiny boner, it sends

sensuous shocks through his sissy body. Pre-cum dribbled from his little head.

“I wanna fuck you, baby,” Reggie said to Deborah.

As if she wanted to humiliate Sebastian, she says, “Hmm, let’s do anal first,” something she had never given Sebastian.

Reggie quickly slides two fingers into her asshole as they kiss. She clenched the fingers inside of her asshole. Sebastian clenched in sympathy. Reggie’s fingers were like sausages.

“Relax,” Reggie said.

She moans again but obeys. After a few minutes of fingering, Deborah feels herself become looser, and Reggie sits back, withdrawing his fingers from her. She spots his raging hard-on between his legs and shuffles forward, lying on her stomach in front of him. She gazes up at Reggie as she swallows his black cock. The man’s mouth falls open, and he grabs her hair, holding her in place while his cock is deep in her throat.

“Deborah, holy shit,” Reggie moans.

The woman bobs, ensuring that Reggie’s massive cock is wet because she knows its next destination is her asshole. It’s like Reggie reads her thoughts, and she feels his fingers on her anal sphincter. He pushes inside, and Deborah moans around his cock. She rocks back and forth, fucking herself on his finger while sucking his giant cock. Soon, she’s moaning, groaning, panting, and her orgasm is nearing. Reggie pulls his cock out of her mouth and his fingers out of her ass.

“Why’d you stop me?” Deborah asks.

“I want you to cum with my cock in your ass,” he said simply. “Turn around.”

Deborah turns around so she’s on all fours, and Reggie slaps her butt. He slips his fingers back inside her asshole, and she grips the floor. He pumps them in and out a couple of times before sliding them out, then something more complex and girthy replaces them. His cock. Sebastian shudders when Reggie pushes the tip inside of her ass.

“Please be gentle with her,” Sebastian begs.

Reggie glances at the sissy and smirks. “I’ll go slow at first, but once I’m inside your girlfriend’s asshole, I will fuck it hard.”

“Do it,” Deborah moans.

He’s true to his word and slowly slides the rest of his twelve-inch cock inside her. Deborah tries her hardest to relax as his cock stretches her like never before. It feels like Reggie is attempting to rip her open from the inside out, and she breathes through the pain. When all of his cock is inside her, he holds himself still.

“Breathe, baby. You gotta lot of cock in that asshole.”

“I’m trying,” Deborah whines while Reggie gives her gentle kisses all over her neck and back.

“Are you OK, Deb?” Sebastian asks, still dancing sexily to the music.

“More than OK,” Deborah said.

The woman squeezes and relaxes her ass, and slowly the cock filling her body feels natural. Deborah doesn’t have the chance to say she’s ready before Reggie pulls out and slams himself into her again. Her knuckles turn white from gripping the rug as hard as possible as Reggie begins

fucking her ass to his heart’s desire. It takes maybe three more thrusts before the pain turns into unbelievable pleasure. It’s the tightest fit imaginable and overwhelming in an orgasmic way. There are new pleasure points in her body, the cocks triggering, and she loves every minute. Reggie is inside the most intimate part of her body, taking her anal virginity.

With this in mind, she wants Sebastian to see. “Bitch, I want to see you what a real man’s cock is capable of doing. Compare that to your useless clit of a dick,” she said hurriedly.

That got Sebastian’s attention immediately.

Suddenly, Reggie flips her over, so she’s underneath him. Without skipping a beat, he goes back to fucking her in earnest. This time Deborah has the opportunity to stare into his brown eyes and see how this feels for him. Reggie appears to be having the time of his life.

“You’re so fucking tight, Deborah. Fuck, this is great,” he said.

He cradled her face in his hands and kissed her deeply. She lifts her upper body to reach him and kiss Reggie back.

When the black man’s tongue swipes her bottom lip, she let him in, forcing her mouth open. One specific thrust sent a shockwave to her pussy, and Deborah realized her vagina needed attention.

She turns to Sebastian and shouts, “Sissy, get down there and lick my pussy while Reggie owns my asshole.”

Sebastian doesn’t hesitate and is soon flicking her clit with his tongue. He knows she likes that technique. With all these sensations combined, Deborah feels like her brain exploded. She let out a long-drawn-out moan at the sensory overload. Reggie pushes her knees up near her chest to give Sebastian better access, and the sissy goes to town. Sebastian’s fingers slide inside of her cunt, and she groans. He can feel the giant cock sliding in and out of her asshole through the membrane that separates her colon and vagina.

“That’s so fucking hot,” Reggie moans but never slows. “Fuck me harder,” Deborah whines.
Sebastian seriously didn’t think it was possible when

Deborah said it, but Reggie proceeded to fuck her harder. The black bouncer pushes one of her legs over the other,

forcing her onto her side, and he leans over her. One of his hands grips her throat while Sebastian adjusts so he can keep licking and fingering her pussy. Deborah never wants this to end.

“Yes, just like that. Oh my God, yes,” she moans.

Deborah’s asshole and pussy are tightening around the various appendages inside her, and she’s close. Sebastian knows because he’s seen it before and presses his thumb against her clit like her orgasm button. It works. Deborah screams as she squirts on her sissy husband’s fingers.

“AHHHHHHHHHHHHHHHHHHHHHHHH.”

Reggie doesn’t let up and fucks her ass like she just didn’t have an earth-shattering orgasm. Deborah’s mewling at this point, her cunt is spasming around Sebastian’s fingers, but she can do nothing but take it. It isn’t long before Reggie swears, and Deborah feels him unload inside her bowels. He pulls his cock out of her, and she feels the jizz leak out of her gaping asshole.

“Push,” he commands. Deborah does as he asks and more of his semen drizzles out of her asshole. “Fuck, that’s

beautiful.” He scoops up what escapes and holds it out to Sebastian. “Eat it, sissy,” he said.

Sebastian takes those sausage-like black fingers covered in jizz and shit into his mouth and savors the taste. The sissy’s eyes never leave Reggie’s as he cleans the fingers, swirling his tongue around the fingertips for good measure before releasing them. Reggie collapses next to Deborah, turns her head toward his, and captures her lips in a kiss.

“That was hot,” Reggie said, still breathing heavily.

“Let’s go to the bedroom and keep fucking,” Deborah said.

“As you wish, honey.”

Sebastian gasps. He wonders if this is a dream or a nightmare.

*****

Reggie walks into Deborah’s bedroom with the confident ease only an alpha man could. Deborah stops her sissy husband at the door and smirks at him. You can edge your baby dick, but no cumming.”

“OK,” Sebastian said glumly.

Suddenly, Reggie burst out laughing at the sight of Sebastian’s dick. “Damn, woman, why you go hook up with a dick that short?” he asked Deborah.

Sebastian blushes.

“A moment of weakness,” she said and grinned. “He eats pussy like a dyke, so it’s not that bad.”

“I ain’t ever seen a cock that small before,” Reggie continues. “Any wonder he likes dressing up in women’s clothes. He practically is one already.”

Deborah laughs. “Oh, Reggie. You say the nicest things,” she said and shut the door in Sebastian’s face.

In the spare room, Sebastian can hear them through the wall. The sounds of their fucking make his little dick as hard as it’s ever been, and he dares not touch it because he knows one touch will make him ejaculate. His only thoughts are of himself, even though the sounds coming through the wall shake him to the core.

“Yes. Fuck me. Fuck me. Make me your bitch,” Deborah screams in the other room.

It goes on all night, but eventually, the next door falls quiet.

*****

Sebastian has never felt so ashamed and humiliated listening to Deborah orgasm repeatedly on the giant black cock. His little boner is still raging even though everything has stopped for now. It demonstrates how torn and broken he is inside. He feels defeated and depressed by what’s happened since the start of the boat tour, but his dick tells a different story. Somehow, Sebastian’s reveling in the sexual humiliation he’s suffered. It’s like the ultimate mind fuck. He does fall asleep, but his phone buzzes before even that can calm the sissy male.

It's a text message from Deborah. It says: ‘Get in here, bitch.’

After quickly straitening his makeup and wig, Sebastian entered the main bedroom to find the two smoking a joint. It’s just gone seven am. They ignore Sebastian until he’s standing meekly by the bed.

Then, without looking at him, Deborah said coldly, “Did you enjoy yourself last night, bitch?”

Sebastian grimaces. “I beg your pardon?” he asks, feeling his stomach roil.

“Do you think we didn’t hear you jerking off all night?”

He gasps, wondering how they could hear anything with all the noise they made. “I’m sorry if I made any noise,” he said softly.

“I’ve been thinking, “Deborah said, making Sebastian shudder. “I think it’s time you learned what a real cock feels like.”

“Do you mean he, ah, he wants to—” Sebastian begins.

“Sissy bitches like you don’t get the right to choose what they want,” Deborah snaps. “So, shut up, and bend that pretty butt over the bed.”

“But, honey, I’m not gay.”

Deborah gets out of the bed and grabs Sebastian from behind. “Is that what you said before you sucked that bouncer off last night?”

“He coerced me into doing it. I didn’t do it by choice,” Sebastian whines.

Reggie butts in, saying, “Maybe, but once you started, you sure enjoyed yourself,” and laughs.

Grabbing the swooning sissy by the shoulders, Deborah says, “You need to learn. Let’s start with a little cocksucking to get Reggie nice and hard.”

“No, no, not again,” Sebastian groans as Deborah pushes him onto his knees.

Reggie scoots across the bed and swings his legs over the side. As the sissy’s face gets closer to the soft black cock the stank of sex hits him making him gag. That cock is covered in the secretions of all Deborah’s holes. Deborah grabs the sissy’s face and slides her fingers into his mouth to force him to open up.

“Open wide, Bitch,” she said. “Get as much in there as you can.”

The thick head of the black cock slides inside Sebastian’s sissy mouth and toward his throat.

Reggie grunts. “Hey, watch the teeth, bitch.”

That cock slides deeper and deeper, going down the sissy’s throat. The taste is rank and humiliating. An intense wave of odor rolls out of his crotch—thick, musky, and superheated. Sebastian swallows a mouthful of spit before it leaks from the corners of his mouth, then plunges

his face into that hairy, meaty, smelly crotch. Reggie’s cock is sticky with sweat, pussy, asshole, and semen. Deborah laughs. “What a sissy fag,” she scolds. “I

should tell your mother how well you suck cock.” “That’s it, sissy. Suck me,” Reggie moans. “You’ll

sacrifice your self-respect and dignity just to lick my hairy balls. It’s what you were born for, sissy. Not licking pussy like a stupid cuck.”

Sebastian sucks Reggie’s testicles into his mouth and washes each with his tongue. Then he licks the backside of the ball sack before moving up the valley between those fat thighs and scrotum to take the black cock into his mouth and start bobbing. As the sissy sucks and licks and bobs, he tastes a steady flow of pre-cum. The inside of the sissy’s mouth is gooey with the stuff.

Then Deborah pulls him off the cock and throws Sebastian onto the bed. Reggie gets up and positions his stiff cock into the sissy’s butt cheeks. The sissy feels him push it inside his anus slightly. The pain instantly hits as Reggie forces it inside Sebastian’s asshole.

“Oh, God, it’s too big,” Sebastian screamed. Reggie is as hard as iron, slowly pushing his cock inside the sissy’s asshole. The sissy inhales sharply at the pain. “It hurts. Please stop,” Sebastian screams.

“Yeah, take it. He’s pushing it inside you,” Deborah shouts. “He’s taking your sissy virginity.”

The enormous cock forces itself past the flesh, impaling Sebastian and ripping him open.

“Ooh, bitch, it feels good,” Reggie moans.

“Wait. Please wait. Just wait,” Sebastian begs. “Give me a chance to get used to it.”

The poor sissy has his fist in his mouth to stop him from screaming.

Reggie pulls his cock out some, then shoves it back in hard. “Oh, yeah. Your pussy is tight,” he moans softly as his cock slides in and out.

It’s burning his asshole from the sheer force of twelve inches of Reggie’s thick cock plundering Sebastian’s bowels.

“Shit, I’m cumming,” Reggie moans and shoves his cock in hard, so his balls are touching Sebastian’s butt cheeks.

All twelve inches of Reggie’s massive cock is inside Sebastian’s belly, shooting hot semen. Sebastian suddenly feels an orgasm rush over him, and a dribble of jizz comes from his little boner. The black man pulls his cock free and heads for a shower.

“Come on, Deb. Let’s hit the shower,” he said.

She nods. “OK, babe,” she said. “Let’s leave this sissy bitch to wallow in his shame.”

Epilogue

It was a lousy month for Sebastian. Deborah had multiple black men over and made Sebastian serve them dressed as a woman. Every time he complained, she would tell him she’ll release the hours of the video she now has of him dressed as a woman and sucking and fucking big black cocks. Sebastian quickly relented. Deborah was in charge now.

He could dress in his male clothes while he worked (except for the lingerie and his butt plug) but had to be fully dressed as a sissy woman by the time Deborah got

home from work. He’d have to go the whole way. He’d have lingerie, a corset, and a bra with fake breasts, giving the sissy a D-cup. There’d be a suspender belt and stockings and high heel shoes. He’d also be in full makeup with a wig and a short black dress he wore a frilly white apron over.

If she had a guest over, Sebastian would serve them dinner while Deborah made fun of him and exposed his tiny bald dick to make her guest laugh. They made the sissy do many photo shoots and videos doing all kinds of depraved things. Eventually, Deborah grew tired of the game she was playing and called the sissy into her bedroom one night for a chat.

“Sit down, bitch,” she said, indicating a chair across the room. As Sebastian sat, she said, “Spread your legs and show me your little clit.”

He did so, revealing the crotchless panties he wore and his little nubbin of a soft dick and tiny balls poking through the slit. “Do you need something, mistress?” he asks, head-bowed.

“I’ve been thinking,” she said. “I can’t have the people from work finding out about this little arrangement. So, I’m dumping you.”

Sebastian’s head pops up, his eyes wide. “Have I done something wrong?” he asks.

“Apart from being a sissy wimp with a tiny dick?”
He sighs. “Sorry, mistress.”
“I want you to move out tomorrow.”
Sebastian gasps. “But this is my apartment. You can’t

make me move out. You should be the one moving out.” Deborah lies back on the bed and laughs coldly. “I have

so many photos and videos of you doing nasty shit dressed as a sissy fag. Do you want me to send that shit to everyone you know?”

“No, mistress.”

“Good. You’ll sign over the title and deeds to me,” she said coldly. “Where you go, I couldn’t care less. But I might need you now and then to help me entertain company.”

“Yes, mistress,” he said, feeling his soul crushed.

“You’ll also pay my bills here. I know you can afford it,” Deborah said. Sebastian has his eyes closed as the enormity of it all sinks into his mind. But Deborah isn’t finished with him yet. “To show me you will do as you’re told, I want you to come over and eat my pussy. It has a few loads of Reggie’s cum in it. Come over and taste your shame, bitch.”

Sebastian sits there for a moment. He’s shaking. Deborah has not just mind fucked him but is now blackmailing him too. He decides nothing can be done about it for now except give in to her demands. He stands and moves slowly to the bed. Deborah parted her legs to reveal her shaved, sticky pussy. The waft of recent sex is pungent in Sebastian’s nose. Soon, his tongue is snaking inside her cunt and tasting a mixture of pussy slime and alpha jizz.

“Good, girl,” Deborah said, holding Sebastian’s head against her pussy. “I knew you’d do as I told you. Little dick sissies are weak and need to be controlled. Mmmmm.”

Sebastian licks away for a long time. His mind is racing, though. He has to move out of his home. No, it’s not his home anymore. It now belongs to Deborah. Whatever will he do?

The End.