Staying in the family 7 (Patreon)

Shaun eagerly waited for his date in the living room, checking his breath one final time. He could smell a slight hint of alcohol on his breath so he quickly popped a stick of mint gum in his mouth. “Shaaaaaun.” Emma cooed playfully from the hallway, “I hope you’re ready.” The girl who followed behind his sister was not the same woman he expected to meet. She looked the same of course, different clothes and makeup obviously, but otherwise she was the same as the pictures he saw. The biggest difference was her demeanor. 

From her pictures he had almost expected her to stroll in with a cocky attitude, exuding the same power and control as the last photo which still burned into his mind. Instead Natalie minced in behind his sister on her high heels. One arm at her side, the other across her stomach, clutching her elbow in her hand. “S-shaun? Right?” She asked hesitantly and barely above a whisper without looking directly at him.

Shaun chuckled lightly, “That’s me.” ‘Damn!’ He thought, ‘What’s wrong with this girl?’ She was dressed like sex on wheels but she acted like she had been wearing a burlap sack her entire life up until this point.

“Thank you for taking me o-out tonight. It’s…uh, like, been awhile.” She

“No need to thank me. I’m just…lucky I guess.”

“Oh, Natalie! You left your purse in my room.”

“Silly me.” She giggled awkwardly before turning and mincing away on her heels.

“Oh my god!” Shaun groaned quietly, drooping his shoulders, “What’s with her?! She’s nothing like I expected from her photos.” 

“Those are old pictures.” ‘About two hours old.’ She held back a laugh and continued, “I told you she’s going through a lot right now.” Shaun groaned and Emma could tell he was close to bailing, “All she needs is a shot of confidence to boost her spirits.” She said as she adjusted his collar over his jacket, “And you, my dear brother, are just the man to give it to her.”

“You think so, huh?” he asked, more annoyed than in disbelief.

“Absolutely! You should’ve seen her when she saw your pictures. She thinks you’re a real hunk.”

“Does she now?” He gave a cocky smile to the hallway.

“Definitely. After everything she’s been through…she’s just worried you’ll want nothing to do with her. But once you show just how sexy you find her she’ll open up to you.”

“Alright…if it’s to help a poor damsel,” he laughed.

“How noble of you. I’ll go see what’s taking her so long. Lose the gum.” She commanded as she walked away from her brother and into her room.

In Emma’s room once again Nate, or Natalie, sat on the edge of her bed, biting his nails as Emma came in. “What are you doing?”

“I can’t find the purse you gave me.” Nate pulled on his black and white checkered side-slit skirt, trying to hide as much of his legs as he could.

Emma searched her room for less than thirty seconds before finding it on her desk, “Did you even try looking?”

“Oh…there it is.” He pulled at his off shoulder lettuce trim top before taking the small purse in hand with a frown. It took some time during their shopping trip but they managed to find a strapless pushup bra. That, with some clever padding, gave him the illusion he was pushing B cups. Not that she expected Shaun to give too much thought to it. Not with the amount of exposed legs, shoulders, and midriff he would get to stare at instead.

Emma noticed the hesitation behind Nate’s eyes as he took the purse in his hand, his red nails standing out against the small black leather clutch. She thought for a moment about telling him if he didn’t go out there and show her brother a good time she would call her mother and expose him right then and there, but a better and more sinister thought occurred to her. “I’ll make you a deal. Since you’ve been a…fairly good girl, if you go out there and act like the cute little love sick girl you are, I’ll delete the pictures we took today.”

“How do I know I can trust you? You’re blackmailing me.”

Emma chuckled, “You should remember why you’re being blackmailed in the first place.” Emma paused for a moment to let her words sink in, “Fine. I’ll give you the pics and you can do with them as you please. Heck, you may want to keep them.”

“Why on earth would I do that?” He narrowed his now neatly arched eyebrows as he glared at her through the curtain of mascara covered lashes. 

“Happy memories?” She shrugged, “Anyway, do we have a deal?”

Nate stood in his black ankle strap four inch block heel with a small amount of wobble, more from unfamiliarity. “Not much of one, but sure.” He grumbled

“Good. Now get out there and greet your date properly.” She practically shoved Nate out of her room. “And remember just what kind of girl you are, Natalie.”

In the living room once more Nate forced a smile onto his face, “Sorry I took so long. I just couldn’t find a thing in that mess.” Shaun heard her giggle.. Everytime Nate did that it felt like a small  piece of him was chiseled off, leaving something softer, something more feminine behind, but what choice did he really have? His own step daughter was blackmailing him, blackmailing him to do terrible things, but if just got through the night he would make it out of the dark tunnel that his life had turned into this day.

Shaun paused before smiling. For the first time Natalie spoke above a whisper and he was surprised at how sultry it sounded. Natalie’s voice was soft but it wasn’t the high pitched falsetto like most girls his age he had met before. Instead it was deeper,smokey, throaty. The only word he could think to describe it was husky. “A beauty like you is well worth the wait.” 

“Flattery will get you everywhere.” Nate forced a smile to his face, holding back the urge to roll his eyes and push his way past the feeling of shame that came along with a man… his step son call him a beauty. 

“One can hope.” Shaun offered his arm to the slim beauty in front of him, “Shall we?”

Forcing back a shudder Nate took the lumbering idiot’s arm and smiled, “With you? Totally!” Taking out a glittery phone from a small purse he held out his arm as high as he could and took a selfie of the two of them together. Snapping a second photo Nate held himself to his step son’s side in an attempt to make himself appear demure in the photo. Each one was a psychic nail to his ego, another piece of proof of what was happening. Emma had been clear on the type of girl her friend Natalie was and how he needed to remember just who “she was” in order to get out of this without things getting worse. Considering how things were, he didn’t want to consider worse, but did want to consider what he could do to get back at her once he climbed himself out of this hole.

Pressing his legs together as tightly as he could, Nate felt the car's air conditioning blow across his hairless legs, making him unable to forget even for a second how he looked, not that his feet stuck at an angle from the shoes wasn’t already a reminder. He could see out of the corner of his eye Shaun looking over at him every once in a while as they drove, each look making more apprehensive about the situation, driving his mind on to think of how he could get out of this without doing what Emma wanted him to do. “You really are gorgeous Natalie, I know Emma is your friend, but we…well sibling rivalry makes it so she doesn’t always do nice things for me, to me. It makes me wonder how I find myself in a situation like this.” His eyes focused on the girl's lips, sliding down her slim neck to her bust and then to her legs. Going out with her was exactly the thing he needed after the day he had.

“I’m here because of cheating.” Nate answered honestly, it would have been more accurate to say him being caught cheating he thought back to Emma coming home when she should have been at school. Sarah coddled her children too much, he had tried to bring it up once before, but quickly dropped the subject when he saw how upset it made her. He wasn’t their father, that man was gone and she was loaded…he didn’t marry her for the money, that was just a happy accident. The world rewarding him, and he wasn’t going to fuck that up by starting arguments. He wouldn’t even be risking fucking it up with seeing other girls if Sarah wasn’t always going out of town for long periods of time. Their relationship had always been a physical thing, the person really fucking with what he had was Sarah’s daughter Emma. The girl was a younger, sexier version of her mother and he had more than one fantasy of being in bed with the two of them. What he hadn’t ever dreamed about was the nightmare the girl would put him in.

“Someone cheated on you?” Shaun asked, moving his hand over to the girl's leg, his fingers resting between her tightly pressed together legs. “If you were mine, you would always have my full attention.” He gave the girl a smirk before his attention returned to the road, leaving his hand pressed to her warm flesh. ‘So long as you put out.’ He mentally added. 

As they pulled up to the valet Nate hurriedly took one more selfie, happy the hand was no longer on his leg as he snuck a quick kissy face to the camera in his phone. Nate couldn’t help but frown, his formerly basic black phone looked like it was ground zero at an explosion in a glitter factory. After their trip to the wig fairy Emma dragged him to the mall, he was at least grateful that the wig changed his overall appearance enough that no one could have possibly recognized him in the ridiculous get up he was forced to wear. Their first stop had been a small kiosk where Emma had Nate ask the faceless worker-drone to “make it cute as hell!” The worker had given him a strange look but did as he asked anyway.

Afterwards, Emma informed him how horrible his voice had sounded. As if he needed reminding, he tried his best to sound like a woman but sounded like a poor imitation a bad drag queen might do. The rest of their shopping excursion she used to instruct him on exactly how to speak, resulting in the husky voice that sounded more at home in a smoke filled jazz club, all while being forced to try on one outfit after the other and even pose in the stupid things.

Nate grimaced at the notion that Emma had more blackmail material over him now. He could only hope that the wig and makeup did their jobs well enough that he could make a convincing argument that it was photoshop or some random girl doppleganger. Of course, she claimed she would give them to Nate. 

Nate silently groaned as he allowed Shaun to escort him in the surprisingly expensive restaurant and pull out his chair. Nate smiled genuinely for the first time that night as he looked over the menu and it’s all too familiar lack of prices. Nate himself had only eaten there once before and with him and three friends splitting the check the meal still came out to over a hundred dollars a person, and that was before the price of the wine. ‘If these stupid kids wanna blow their allowance on this stupid little scheme, fine by me.’ He thought eagerly as he scanned the menu.

“I probably should have asked sooner,” Shaun chuckled while Natalie gawked over the menu, “A girl as drop dead gorgeous as you is probably a vegan. Right?”

A small part of Nate died inside as he was called gorgeous by his stepson. An even larger part fell away as he forced himself to giggle at the compliment, “Not even close.” He leaned over his menu, “I love meat.” Nate blushed, wide-eyed, realizing with how he was dressed and how it no doubt sounded to the horned up Shaun. “W-what’s good here?” he cleared his throat nervously.

Shaun chuckled lightly, one little comment and she was already begging for his meat? ‘The poor girl probably never ate so good.’ He gave a cocky smile as Natalie buried her face in the menu. A moment later the waiter came to the table. Shaun handed his and Natalie’s menus to the waiter as he ordered for the both of them. “We’ll have two braised boneless short ribs with mushroom risotto and herb and honey baby white carrots. And a bottle of Pinot grigio.”

Nate growled quietly, “Actually,” he cleared his throat, reminding himself to speak with his stupidly sultry voice, “we’ll have the Châteauneuf-du-Pape since that pairs better with red meat.”

“An excellent choice, miss.” The waiter said before walking away.

Shaun glared quietly, who did she think she was? She didn’t even know what to order and she had the gall to correct him?! Shaun felt the grin slowly crawl across his face as he continued to stare at the gentle slope of her neck reminding him what was in store later. “What?” she smirked as she twirled a loose strand of hair around her finger.

Shaun took her free hand in his with the same hungry smile “I like it when a girl can take control.” Shaun kissed the underside of her wrist softly, “But just because you’re beautiful don’t expect me to lay back and make it easy for you.” A shiver ran through Nate from the kiss. He had kissed girls there before after reading in an article how they loved it, but he had never experienced it before.

Nate groaned internally, Jeez!’ he thought as he pulled his hand free, ‘No wonder he can’t find a girlfriend if this is how he acts on a date.’ Nate frowned at his own thoughts. Clearing his throat again, “You can’t possibly think I’m beautiful.” He wrapped a finger around a strand of the wig Emma and that effeminate hairdresser of hers practically glued to his head.

Shaun frowned, he hated stuck up girls who would pretend to put themselves down just so someone would give them a compliment. but this girl was genuinely sexy and she couldn’t see that?  “I do. You are the sexiest woman, with the sexiest pair of legs of any woman I’ve ever met. When Emma showed me your pictures I about lost it.” Shaun smirked, imagining her completely nude except for her high heels. He always had a thing for women in heels and the way it made their asses look.

‘She showed him those?!’ Nate blushed furiously. Before Nate could deny Shaun’s statement or even explain away the photos Emma had forced him into after their mall excursion, the small glittery phone that sat silently in his lap vibrated to life.

Em: Remember to smile like the pretty girl you are!

Em: New idea!

Shaun loved the small blush that came to Natalie’s face. And the coquettish smile was enough to convince him to forgive her for checking her phone in the middle of their date. He ignored the buzzing nuisance when she looked around the restaurant before leaning back in her chair. He was about to ask what was wrong when suddenly he felt her foot pressing into his thigh, slowly massaging into his crotch. Shaun laughed nervously, checking that no one else could see them either. Natalie bit her lip while wrapping a finger around a strand of her long blonde hair. 

“I wasn’t kidding.” Shaun chuckled and grabbed the feminized man’s now bare foot as it rubbed into his crotch, “I love your legs.” It was Nate’s turn to be surprised as Shaun started massaging his leg, sending waves of pleasure rippling through his body. As Shaun stroked Nate’s sore leg he didn’t realize he was continuing to stroke Shaun’s growing cock through his pants, pressing his bare foot into his date’s crotch. Nate loved when Sarah wore heels, the way it made her legs look, the way it made her ass look in skirts, the way her hips swayed when she signaled she wanted him? He loved all of it! But he never knew just how much of a pain in the…legs they were! After only wearing them a few hours he was ready to gnaw his legs off like a fox trapped in a snare just to be free of the pain! But if there were a bright spot in all of this, it was this moment. As awkward as it was to be touched by his stepson only five years younger than himself. As much as he should not be enjoying it. As much as he hated Emma for texting him to do this. As much as he still feared she must be here somewhere watching them. He couldn’t help but let out a loud and shuddering moan of pleasure as Shaun worked a knot out of his thin calf that no previous masseuse had been able to work loose. Granted, those he had gone to for the happy ending more than any real quality massage.

For a brief moment he forgot about the blackmail, that he was in public, the fact it was another man touching him, that it was his stepson touching him as he let himself simply…enjoy this one moment of bliss. He was also completely unaware how loud he was moaning until a waitress suddenly appeared beside him and cleared her throat. Burning red, Nate pulled his foot away and sat up in his seat once again. “Your dinner, ma’am.” Nate refused to look at the woman as she placed a plate in front of him and a matching one in front of Shaun, who of course he could see out of the corner of his eye was smugly happy as he cut into his food.

Shaun did his best to hide the proud smile on his face, he had enjoyed watching Natalie moan and undulate under his touch and she clearly enjoyed it as well since she gave him a footjob through his pants under the table. He felt much like he did when at a strip club, horny and blue balled. There he could pay for some backroom release, but hearing his date’s reaction to his touch told him she was wet and just as horny as he was.

Feeling the now familiar buzz in between his thighs, Nate opened up the glittery phone and read the newest message from Emma.

Em: Since you’re such an instagirl you should take pictures of your food for everybody to see!

Nate felt his stomach turn when a second message appeared, this one came with two pictures attached. One of him shaving in front of the mirror, and another of him having makeup put on his smooth face.

Em: I have over two dozen pics of you. So far you’ve earned 2 back.

With great restraint Shaun managed not to roll his eyes as Natalie took out her phone and took not one but several pictures of her meal. The first one she took, paused and pouted, and clearly decided the lighting wasn’t perfect so took four more before typing away at her phone, even standing up to change the angle. Judging from the pretty artsy selfies Emma showed of her she was no doubt finding the perfect filters for whatever social media she was posting them too. Nate smiled as he took the photos, he hated doing this, he hated when he saw people doing this. Food was to be enjoyed, yes, but it was to be eaten.

While she busied herself with her posts Shaun gathered food onto his fork and offered it to her.

Nate licked his lips, smelling something delicious approaching. Tearing his eyes away from his phone he saw the source on Shaun’s fork. ‘Is it genetic?!’ He thought angrily. 

Less than a month after he and Sarah married, Sarah had gotten the idea in her head to feed him some pie off of her plate, when she had done it again he didn’t mind as much because her sexy ass  was sitting in his lap. Now her son was trying to do the same?  He still could remember how pissed she had gotten when he had ever so calmly told her he was not a damn toddler! It was actually one of their first fights as a married couple. He had actually thought they were going to divorce over the incident. It didn’t stop it from happening again, she often got her way.

Nate, remembering Emma’s warning that he needed to act like a love sick girl, slowly opened his mouth and let Shaun feed him. Despite feeling like an infant boy or a woman he smiled, focusing on the delicious and expensive food that melted in his mouth like butter instead of his humiliation at being fed like some child. “Mmmmm…. God, that’s just…soooo good.” he moaned. ‘At least the food is good.’ He thought.

“I hope everything you put in your mouth tonight is just as tasty.” Shaun whispered into Nate’s ear. His warm breath on Nate’s neck sent a shiver throughout his body. The smile on Shaun’s face touched his eyes as he saw the girl shiver in excitement. Seeing her visibly react to him wasn’t just something he enjoyed, it was exactly what he needed after being rejected for yet another job.

Swallowing the bile in his throat, Nate smiled and faced Shaun, “Promise–” Nate cut himself off, noticing the all too familiar look of a man about to shoot his shot and kiss the beautiful girl he was mere inches from. Panic fueled reflexes Nate grabbed his phone and traded the devil for a lesser demon as he took another selfie with himself and Shaun cheek to cheek in a romantic restaurant.

"Say…Ammirato!" Nate cheered and giggled playfully as he pressed his cheek into Shaun’s snapped the first picture. He may have had to play the part of a vapid, flirty, girl but he wasn’t about to french his step-son. “One more, for luck!” He couldn’t help but smile as he pulled him back into frame. Emma had no doubt set up this date to torture him, but as he caught a glimpse of the annoyance behind Shaun’s eyes he realized she couldn’t fault him if Shaun found “her” annoying and shallow for doing exactly what he was told. And if he was annoyed at the bubblegum blonde he wouldn’t be thinking of kissing “her”. A man will put up with a lot if it meant there was a one percent chance of getting laid. But, even so, every man had his limits.

Taking a sip of his wine, Nate took a deep breath. Promising himself once this was all over he would take what remained of his savings and drown this night out in an ocean of booze. With the selfies done Nate giggled giddily, or as much as he was capable, and did his best to imitate a few of the more annoying women he had encountered in his bar. “Oh my god, I just love this place!” He cheered, making sure to emphasize “love” as much as possible while reminding himself to talk with his hands as he did. “Where did you find it?!” Before Shaun could answer, Nate cut him off, “Shame on you though!” He giggled, “You haven’t said anything about my hair. And, I like, spent sooooo long on it!” Before Shaun could respond with a compliment Nate cut him off once again. And their conversation continued like that for the next ten minutes as Nate picked food off of Shaun’s plate, largely ignoring his own except for his wine. Nate took another sip of his wine, now on his second glass. “Mmmm…” Pairing this wine with this meal was a perfect choice. It would be a shame to not remember the food or alcohol of this evening, but everything needed to be scrubbed from his brain. He wanted to get drunk enough that he never remembered wearing a pair of heels for the rest of his life.

Finally the wine and nerves caught up to him, “Excuse me. I have to go to the little girls room and tinkle.” He giggled as he stood and hurried to the bathroom.

“Ma’am.” The waitress called after Nate as he opened the door to the bathroom, “That’s the men’s room.” 

Nate swallowed hard and checked, sure enough she was right, “Oh, oopsie.” He laughed, “I just saw a door and thought I had a fifty/fifty shot.” He said, rushing into the women’s room and quickly the stall. Taking the opportunity while he was seated and had a moment to breath, he sent the last selfies to Emma.

Em: You two make such a cute couple! Have you thought of what you will name the nephews and nieces the two of you will give me?

He growled.

Em: But this only counts as one.

Em: If u want more u gotta give more ;)

He rolled his eyes and continued about his business. Hiking up his dress Nate considered how much more work it was to go to the bathroom in a stall as a girl, when he stopped to let out a sigh realizing that he had thought of this as his dress, and that it was true.

Meanwhile, Shaun sat at the table by himself, enjoying the momentary silence and picking at what was left of his food and drinking his wine when his phone buzzed. 

Harpy Queen: How goes it?

He frowned at the message from Emma.

Shaun: How long is she staying again?

Harpy Queen: A while. Y?

Shaun checked over his shoulder towards the bathroom, making sure she wasn’t on her way back, before he quickly sent his sister a quick rundown of the hell Natalie had just put him through, leaving out what she had done with her foot.

Harpy Queen: Oh no! I was afraid this might happen.

Shaun: What? She a split personality or somethin?

Harpy Queen: No!

Harpy Queen: When she gets nervous she kinda amps things up to the nth degree.

Shaun: Good for her. Hope she doesnt get so nervous sleeping in YOUR bed!

Harpy Queen: Look! We had a deal. 

Harpy Queen: Besides she just wants you to kiss her!!

Shaun: Hell no

Harpy Queen: She’s acting this way cause shes afraid you dont like her. Show her that you do and she’ll calm down!

Shaun: Or shell wanna get married!

Harpy Queen: If I’m wrong…ill talk to her. 

Shaun shook his head, letting the conversation linger. He did want to kiss her, hell if he could he would bend the girl over the table and fuck her here. At first when she talked he hung on every word, she was close to his own personal phone sex operator, but the more she talked and what she talked about rubbed on him like sandpaper. He thought she could be a the perfect woman, if she was mute.

Harpy Queen: $200 says ur wrong

Shaun: you wanna bet on your friend?

Harpy Queen: cuz i know im right

Shaun: if your wrong you talk to her and she stays in your room. 

Shaun: and you still give me the $200

Harpy Queen: fine! But you cant be a dick to her.

Harpy Queen: I expect you to be the perfect gentleman.

Shaun: Arent i always?

A couple of minutes later, Natalie returned. She continued her rapid fire chatter and for a moment Shaun considered backing out of the bet. But through the constant topic changes, selfies, pics of the wine, pics of the small candle in the center of the table, and the near endless monologues she had begun to find more and more reason to touch him. When she did let him speak, usually because she had decided to take a sip of wine, she would wrap her finger around a strand of hair and gaze longingly into his eyes. ‘Fuck it!’ He thought as she scooted closer beside him, insisting on another picture of the two of them, ‘What have I got to lose?’

Nate only realized too late, in his haze, that he hadn’t opened the camera to take a picture. ‘Stupid thing!’ He pouted, waiting for his phone to load whatever app it was he had accidentally opened. ‘It’s these damn nails!’ he glared at his painted nails, they were almost imperceptibly longer but they made using his phone more difficult. “Natalie?” Shaun said softly in his ear. When Nate turned to acknowledge his fake name was called, Shaun’s lips suddenly pressed against his. Nate gasped, or tried too. Only succeeding in allowing Shaun’s tongue access to his mouth. Nate groaned, trying to push Shaun away with his one free hand. The combination did little to slow Shaun down as he continued to makeout with his own feminized step-father. It would have been comical to Nate had he not been the feminized step-father. Finally Shaun stopped when he heard the dull thunk of Nate’s phone on the table.

“Well…I didn’t expect that.” Emma giggled.  Nate froze like a deer in headlights. On his phone’s screen was Emma’s face.  “I hope you two kids brought protection. I’m not ready to be an aunty just yet, but I think Emma would be a great middle name for my future niece.” 

Natalie grabbed her phone, trying desperately to end the call. “Good night Emma.” Shaun smirked, repressing a laugh, as he took the phone from Natalie and hung up the phone.

“Now where were we?” Shaun asked, putting his hand on the girl's leg under the table, rubbing it gently, moving his thumb across her flesh as he leaned in close.

“I umm don’t think…” Nate’s heart started to beat faster.

“Shhhh… no need.” Shaun’s other hand moved up his date’s neck, his finger tips caressing her gently before holding her by the back of the neck to support her as he pressed his lips to hers once more. ‘Leave the thinking to me doll, it clearly isn’t what you are good at.’ Shaun thought as he greedily kissed the girl, thrilled to feel her shiver once again in excitement at his touch.