Press Your Luck 29 (Patreon)

The next morning, Lucy stretched her arms high above her head. She looked at the slumbering hunk of a man beside her and smiled with a wistful sigh. He was such a sweetheart, she wished she could do more than just sex to pay him back. Shrugging, she gently kissed him on the cheek. Standing up and planting her heeled feet on the floor Lucy walked into the bathroom, otherwise naked, enjoying the sway of her hips and the slight jiggle of her breasts, unaware of the dried cum that had leaked out of her ass during the night but distinctly aware of the dried cum between her legs she had left herself. She had lost count of how many orgasms she had before Daniel finally relented. At one point she thought he was done after her second orgasm and his first, but he had only stopped to catch his breath and pin her face down in the pillow once more.

“Ugh, I am, like, such a mess.” She said at first as she caught sight of the dried cum around her lips. “Thought I got all of you.” She giggled as she ran a finger over her lips and licked it clean.

Standing in front of the mirror she examined her naked body for the first time in a long while. She ran her hand through her hair, shaking out the post-coital bedhead before she smiled at her reflection for the first time with genuine happiness. “I take it back. Girl, you are, like, super sexy.” She giggled, kissing her reflection. Val was right, she should be nicer to herself. She felt silly coming up with nice things to say about herself but…silly wasn’t always bad. “You…I have such a sexy body.” She giggled, “My smile is, like, a million whats.” She paused, scrunching up her nose… "Wait…is that right?" Lucy shrugged.

Val always insisted she come up with something that wasn’t just about her looks. ‘Why’s she gotta, like, make everything so hard.’ In her silent contemplation she couldn’t help but catch sight of her hair and examine it more closely. Taking note of her blonde roots. “Aw.” She pouted, “Guess I’ll have to get that touched up.” Scrunching up her nose she smiled once more, “I wonder if Daniel would like me as a blonde?”

She shrugged and kissed her reflection once more before stopping turning her attention to the tub and examining several bottles on the raised platform around the tub itself. She poured a couple of nice smelling bottles in the water as it filled, immediately watching as the bubbles exploded over the surface of the water. After a few minutes she took off her heels with a small reflexive pout before sliding into the hot water. She couldn’t put her finger on it, but something felt different about that morning. She felt…lighter? Something in the air made her…happy?

She started innocently enough just trying to spread warmth to the rest of her naked body. But as her hand grazed her nipple she felt her cheeks begin to burn. Curiously, she gently massaged her breasts and her body alight with new sensations. Had her nipples always been so sensitive? Or did her surgeries change something? With one hand she tweaked her nipple, feeling a jolt of pure pleasure shoot through her body like a lightning bolt ending at the tip of her penis that twitched freely between her thighs.

Biting her lip she took her penis between her forefinger and thumb . She never considered herself small before, she didn’t compare to the male pornstars she had seen on the internet when she would grow tired of the usual girl on girl action. In the past she had told women she was a grower to protect her male ego with the escorts she had hired over the years. But after seeing, and feeling, a few of them in person she had to admit she was at best average. Shouldn’t she want it smaller? Or bigger? Or even…gone? Wasn’t that what that hospital therapist was talking about?

With a pout Lucy rubbed her head, all of this was too complicated. “What would Val say if she could see us now?” She giggled as she caught herself continuously stroking her flaccid penis. Today was a good day, following a great night, she could worry about all  the heavy and complicated thoughts later. Right now, all she wanted was to close her eyes and reminisce about last night with Daniel. Maybe she could wake him up with a special surprise once she got finished and they could see about breaking their previous record.

Unfortunately a repeat performance never came. After her bath, Lucy crawled under the covers and began to stroke Daniel’s penis before putting it in her mouth, only for him to wake up and pull her up by her hair. Initially she thought nothing of it until he quietly stood up and walked into the bathroom.  “Ooh better idea! I’ll join you.” She giggled and followed him to the bathroom. Only to find the door locked. The drive home was at least better. When she tried to cheer up her silent boyfriend with some road head he pushed her hand away with an annoyed grunt. “Driving.”

"I just wanna cheer you up." She smiled.

"Do you?"  He growled.

She nodded eagerly. "Uh-huh!"

"You wanna make me happy, huh?" He asked, turning to face Lucy after stopping at a light and placed his hand behind her neck.

Lucy shifted in her seat, pulling her knees underneath her and smiled hungrily. "Duh." She pulled his hand to her lips and gave it a gentle kiss.

For a moment Daniel's stern face broke into a smile but stopped before it fully formed. "Then get to work." He pulled her head into his lap. Lucy shrieked in momentary surprise before she giggled and unzipped his cock and fished out his cock. With her knees firmly in the seat, her head down and ass up, she pulled her dress down, or rather up, putting her cheeky panties and ass on full display to anyone who happened to look as they drove by. Already she could feel her penis leaking limply into her panties at the thought.

Later that night, after dinner, Lucy decided to dress to impress for bed. Daniel had his fun on the ride home, but it left Lucy on edge and her panties drenched. In her baby blue negligee her dick was already leaking at the anticipation of the night ahead and the memories of the honking cars and cheering men on the way home.

She sauntered into their shared bedroom and found Daniel laying in bed in just his boxers and the covers kicked to the side. “Well hello.” She added even more breathiness to her already breathy voice as she crawled from the foot of the bed until she was on top of Daniel. “I, like, didn’t know it was Christmas already.”

“Huh?”

“Cause you’ve got me a present.” She giggled, massaging the bulge in his boxers. “Can I go ahead and unwrap it?”

Daniel was silent for a moment, “Speaking of, we’re out of condoms.”

Lucy pouted,  he was right, they did need to keep using condoms for now just to be safe from h…her former life. “I think we can, def make an exception for tonight.” She smiled, climbing further atop her man.

Daniel sighed, “No.”

“...no?” She pouted again. “You don’t…want to?”

“I’m tired and I have to get up pretty early in the morning.”

“Oh…okay. Tomorrow then. I’ll totally make sure to stock up on condoms.” Lucy faked a smile as she layed on top of him, pulling the covers over them. His job was important and it paid well, so she shouldn’t really be upset by his rejection but that didn’t change how she felt.

“Okay.” He said as he wrapped his arms around Lucy and rolled over. For a moment she smiled for real as he held her closer until he let go and rolled over, turning his back towards her.

The next day didn’t see Daniel’s mood improving.The next morning he left immediately after breakfast and was in such a hurry he forgot to kiss her goodbye. After she finished cleaning and her other chores and exercising with Val they both left for the store. Valerie of course teased Lucy for using “so many” condoms in such a short period of time as they walked in the house. “Obvi, you can’t count. It’s not like we do it all the time and we, like, already ran out.”

“Still more than I’ve been getting.”

“Maybe if you dress better.”

“You are so not about to give me fashion advice.” She glared as she sat her armful of groceries on the counter.

“Why not?” She asked as she sat her own bags down and searched for her box of condoms, “You totally need it.” Valerie suddenly slapped Lucy’s ass causing her to jump and giggle, “What the he-ck?”

“It’s the code of the streets, girly. Talk shit, get hit.”

“Ooh, you’re totally gonna have to put a chip in the jar.”

“We’ll see about that. Remember, like, I’m the one who gets to dec-deci-figure out what you’re punishment’s gonna be.”

“Are you gonna spank me?!” Lucy asked, bouncing on the balls of her feet causing her breasts to bounce with her.

“Maybe.”

Lucy smirked, stepping in closer to the busty blonde,“Then totally do it harder next time.”

Valerie rolled her eyes, shoving the box of condoms into Lucy’s hands. “Go put up your condoms, slut.”

“I love it when you talk dirty to me.”

“Go before I, like, shove a wine bottle up your ass or something worse!” Lucy giggled as she sauntered away, making sure to wiggle her ass for added measure. Valerie shook her head, ‘...if she weren’t dating Danny…’ she thought absently as she continued putting away the groceries. “Fuck I need to get laid!”

In Lucy and Daniel’s room she opened the nightstand to put the condoms away when she was surprised to discover that they still had a half pack of condoms. Lucy pouted as she looked from it to the new box in her hand, “...he must have, like, not seen them.” she told herself, “We def have enough tonight.” She giggled, placing the new box in the nightstand and closing it before going back about her day.

When Daniel returned home, Lucy prepared a roast with carrots and plenty of gravy knowing how much he loved gravy and thought, hoped, to enjoy Daniel's gravy later on. Meanwhile Daniel worked out in the garage listening to music. After dinner she thought she would take up her usual spot but Daniel returned to the garage. After cleaning up she went to their room and found Daniel already asleep.

The next morning, Lucy prepared for the day, as she always did, before she set out to start breakfast for her man. So it was a bit of a surprise when she found Daniel already up and at the table eating cereal. “Hi…you’re up early.”

"Couldn't sleep." He shrugged, taking another spoonful of coco puffs.

Lucy walked around the table, hugging him from behind and wrapping her arms around the big man. "Did you have a bad day yesterday?"

"Just a long day." He shrugged.

"That stinks." Lucy gave him a kiss on Daniel's fuzzy cheek, "Is there, like, anything I can do to make you feel better?"

Daniel sat silently simply stroking her arm for a moment before he looked at her. Her short skirt and loose halter top with her full breasts exposed to him stirring things inside of him. He loved how short her skirts always were for him. For someone who claimed to be reluctant she sure loved to show off her ever increasingly feminine body. Not that he could be too upset with her, it would be a crime to hide her creamy thighs from the world. Of all the changes he enjoyed about Lucy, her legs had to be at the top of the list.“I’m fine.” He lied. It wasn’t lost on him that her legs and thighs were what changed the least as Harlow transitioned further into Lucy. Outside of possibly shaving them…though he couldn’t recall if he ever noticed hair on Harlow’s legs before.

“...Are you sure? Cause, like, last night we were going too…I mean, I totally get it if you had a rough day and were too tired for us but if…Val says talking is good.”

“There is one thing.” He stood, quickly wrapping his arms around her waist and lifting her on the table sending the bowl clattering to the floor.

“Daniel?!” She gasped quietly. “...what if Val hears us?” She whispered. Despite her questioning Lucy couldn’t help but bite her lip as one hand braced herself on the table, and the other rubbed his bulge pressed against her thighs.

“Shh.” He hushed with a wicked smile as his hand slid under her soft velvet skirt, “Then you better work fast.” He cupped her ass in his hands and bit her neck.

Lucy moaned excitedly, “Fu-fine!” She lay back on the table and pulled her panties off of one leg, allowing Daniel access to her ass and her still freed penis.

“I knew you would be a good little slut for Daddy.” He whispered before grabbing her hips and throwing her legs over both shoulders. Her five inch purple stilettos knocked against one another with every aggressive thrust.

Lucy tried her best to keep her voice down, and for several minutes she succeeded until the table started moving back with Daniel chasing after, his hand wrapped around her throat. “Fu-!” she let out a strangled gasp. If not for the strong hand squeezing her throat she would surely shout like a cat in heat. Why was this turning her on so much?! Lucy’s train of thought was interrupted by the sound of the table scraping across the floor with every thrust until finally it loudly and repeatedly slammed against the back wall.

"Da-Dani-" Lucy's eyes rolling in the back of her head, as she tried to choke out a feeble attempt to beg Daniel to be quiet and not wake Val.

Daniel released her throat and gripped Lucy's hips, pulling her up onto his hips as he thrust his dick into her.

Lucy slapped the table, ignoring the brief pain she slapped her hand over her mouth in time to catch the loud moan that escaped her lips. Her toes curled as his cock pressed against her prostate. Her Heel clattered to the floor Lucy threw her arms around Daniel and pulled herself onto him. ‘Gawd!’ she thought, ‘If someone just, like, told me this is what I was training for I would’ve totally started dancing years ago!’

With her legs still over his shoulders Daniel lifted her off of the table as he continued, now moving Lucy up and down the length of his cock. Lucy dug her nails into Daniel’s back as she bit his neck, her penis leaking freely as she came on Daniel’s cock.

Placing her feet on the floor and bending her over the table Daniel took no time in shoving his cock inside of Lucy’s sensitive hole. Lucy kicked her other heel off to join the first to keep her balance as her legs quivered under Daniel’s powerful thrusts. Lucy couldn’t help but shout in pleasure. Daniel pulled her to standing by her long hair and she gasped again in pleasure. Daniel took the opportunity to shove her panties into Lucy’s open mouth drenched by her own juices and fallen after he sat her down. They now filled her mouth to muffle her cries even as her tongue licked away at her cum.

In no time at all as he used Lucy as his own personal fuck doll Daniel came inside of her. ‘I hope I don’t get pregnant!’ she giggled internally.

Just as he came they both heard the familiar sound of Val’s door opening. The couple scrambled to get away. Lucy hurried to pull her skirt down while Daniel simply turned around and put his cock away. When he turned back he caught sight of Lucy rushing off on the balls of her feet down the hall.

"Good morning, Loosey Goosey!" Val slapped Lucy's ass with a giggle as she passed her in the hall. Lucy giggled and shrieked as she passed while her face burned a brighter shade of red, her humiliation mixing with the stinging on her cheek and the strange arousal from being spanked by both Daniel and Val. 'She totally heard us!' Lucy giggled nervously and scampered off to the bathroom. In the kitchen Valerie took out her ear plugs and grabbed a bowl of cereal. She froze when she walked into the dining room. Why was the table pushed up against the wall?

In the bedroom, Lucy spat out her panties and grabbed a new pair, preparing for her second shower of the morning when she stopped. ‘If Val hears me in the shower she’ll totally glue my…little friend away again.’ She pouted. ‘Ugh that sh..stuff hurts. Like, so much.’ Lucy briefly scanned the bedroom before settling on an unopened box of pads Valerie had insisted she place in the bedroom she shared with Daniel. “Waste not.” She giggled as she opened the box and grabbed one of the pads inside before pulling her purple panties part way up her thighs. She stopped and sat for a moment on the bed as she examined the small square packaging for instructions. “Hmm.” She took her best guess and placed the pantyliner tape down in the back of her panties. Pulling them up felt…odd. The thickness was something she couldn’t force herself not to notice. “How do other girls, like, get used to this?” She wondered out loud.

“Lucy?” Val asked as she knocked on the open door.

“Hi-hi!” Lucy giggled nervously. “You look so pretty!”

Val giggled back, “You’re not wrong.” She smiled back confidently. “Danny wanted me to give you something.”

“...did he leave?”

Val nodded, “He has work, sweetie.” Lucy pouted but nodded as she stood. Immediately regretting it, did Val hear her pad crinkling?! “First, he said you dropped these.” She smirked, holding out Lucy’s heels.

“Oopsie.” She blushed and took the heels.

“Second, he said Elana said you needed to have this.” Valerie placed a small gift box in Lucy’s hands.

“Ooh!” Lucy giggled excitedly as she opened the box. She wasn’t sure what to expect, she had never been given a gift before, let alone from a girl. Everything she had she earned using her wit or skill.

Opening the box her grin fell into a pout. “A…phone?” She asked, confused. How did Elana even know she needed a phone?

“Yeah!” Val cheered, “So, like, apparently your, sweeter than sweet, boyfriend told her you needed one and poof. Phone.”

Lucy frowned. She needed the phone so she could call someone for help but all of those options were burned by Benjamin. “There’s no one from my old life to call.”

Valerie frowned as she wrapped her arm around her friend. Lucy’s mother was gone and in hiding and it was doubtful the people Lucy used to hang out with would be as accepting as her and Danny. “But,” she began, “you have new and, like, way better friends now.” She smiled for the pretty girl beside her. “Danny and I already put our numbers in your phone.”

Lucy turned to face Val, this girl had tormented and threatened her for the last few months but maybe that really was just to help her. “Cause we’re friends?”

She didn’t miss Lucy’s eyes watering as she asked so weakly, “Of course.” Val was surprised when Lucy suddenly threw her arms around her. For a few minutes they simply sat there and hugged one another. “Okay,” Val sniffed sharply, “we should get ready and you totally need to fix your makeup.”

Lucy checked her reflection in the smartphone and saw her mascara had started to run, “Oh shoot!” She swore and ran out of the room on the balls of her feet.

“Are your feet okay?”

“Sooo much better!” Val shrugged it off as Lucy’s Barbie-like personality. “So, like, where are we going?”

“Grocery shopping mostly, plus I have, like, this package I’m sposed to pick up.”

“Oh? A package? How big is this…package? ” Lucy giggled as she leaned out of the bathroom door and winked at Val.

“Shut up, slut!” She giggled as she threw a sock at Lucy.

“You sound just like your brother!”

“Ew! I so don’t wanna know!”

A few hours later, Lucy returned home. Valerie had dropped her off before she headed off to school. With no new list of chores for the day Lucy finished what little needed to be done before she started playing with her new phone and noticed she already had a text message from Elana, or “Bestie!” with several hearts surrounding it on both sides, as she was named in her phone. The only reason Lucy knew who it was, was the traditional selfie Elana had already added to her contact info.

Bestie!: Luuuuuucy!

Bestie!: I hope you love your new phone!

Lucky Lucy: I do! Thank you like so much!!!!

Bestie!: :p pfft no big

Bestie!: its what rich friends are for

Bestie!: hehe!

Lucy giggled and rolled her eyes and continued texting her new “bff”. Lucky Lucy: Aren’t you supposed to be in school?

Bestie!: Who says im not? ;-)

Lucky Lucy: Dont get in trouble and get grounded again.

Bestie!: let em try and catch me hehe

Over the next couple of hours Lucy continued texting Elana on and off while she played on her new phone and Elana pretended to pay attention in class.  When the school day was done Lucy received a selfie of Elana standing outside of the driver side window of her family’s town car and Daniel smiling awkwardly.

Lucky Lucy: Ooh! Who’s the handsome boy!

She giggled as she typed.

Bestie!: My totally hawt driver!

Lucky Lucy: You should hook me up

Bestie!: I would but shame…I think he already has a girlfriend.

Lucky Lucy: Does he now?

Bestie!: He says she’s totally hot too

Lucky Lucy: Not as hot as me ;)

Lucky Lucy: You should still hook me up!

Bestie!: I’ll try. I GOT to go to the mall.

Lucky Lucy: Lucky!

Lucky Lucy: I need to get my nails done.

She pouted at the chipped nails on her fingers, remnants from her aggressive love making with Daniel.

Bestie!: OMG YOU SHOULD TOTALLY COME WITH US!

Lucky Lucy: 4 rel?!

Bestie!: We cn totly hit up a spa!

Lucky Lucy: totally!

Lucky Lucy: Can Val com?

Bestie!: The more the merrier :D

Lucky Lucy: Tell the cutie to cum to my place then!

Lucy locked her phone and eagerly ran into Val’s room where she had spent the last hour hiding. Well, she called it “studying” but being hot as she was she didn’t need to bother with studying. “Hey sexy momma!” Lucy giggled as she bounded onto Val’s bed. Pouting for a second in pain. The weight of her breasts jerk suddenly downward. “Ugh! Fudgicles!”

“What’s wrong?” Valerie asked with concern. Noting the fact Lucy still was censoring herself.

“My boobies…” She groaned as she massaged the large globes.

“Yeah, the good lord giveth and the good lord taketh away.” She giggled.

Lucy giggled back, “Or Dr. Ngyuen.” She pouted, still rubbing her chest in pain.

Val’s smile faded for a moment, “About that…”

“What?”

“I mean, like, about your…extra bits…down there.” She said, pointing to Lucy’s crotch. ‘Ugh, this was totally easier when she was a guy in a dress!’ She frowned angrily at herself, ‘No she was always a girl. I have to remember that.’

“Oh…that.” Lucy pouted, “Can we not?”

“I get that, like, it’s strefs…stressful but we need to-”

“I don’t want it.” Lucy said sharply.

“You don’t want it?” Lucy nodded, not daring to look at Valerie’s no doubt angry eyes. Val took a deep breath, “I know…I mentioned a couple months ago there were, like, these alter…these uh other ways to hide…that until…you didn’t have too anymore. Would you like that instead?”

Lucy wanted to jump on the chance but new better, Val may be her friend now but that didn’t change the fact she could be talking about getting some cartoonishly large pair of scissors and cutting her cock and balls off. “Depends on what.”

Valerie stood and took a box out of her drawer, “I guess today’s your birthday with all these gifts you’re getting.” She smiled awkwardly, very much like her brother. ‘I wonder if she knows they’re totally the same person?’ Lucy wondered as she took the box.

Opening this new box, Lucy was met with more confusion. “Is that, like, what I think it is?!” She couldn’t tell exactly what it was. Whatever it was, it was made of flesh-like rubber and looked like a thong from the silence of the lambs. If Lucy didn’t know better she would swear it was a vagina, complete with a small tuft of red hair above.

“The woman at the store said you can wear it and still, like, go to the bathroom or…have sex?”

Lucy blushed, ‘Wonder if Daniel would like this better?’ She thought. “Well?”

Lucy smiled and almost immediately said yes, it being better than the painful glue! But she stopped herself and nodded slowly, there was always a catch and she needed to be careful, “What do you, like, want in return?”

Val smiled. She knew Lucy would love it as a temporary alternative to the gender reassignment surgery she no doubt wanted, but Lucy’s trauma still required her to gamble or trade. She would keep playing along, for now.