Summary: Sidney is reluctantly persuaded into submitting to Ellen’s humiliating wishes. His sister is along for the ride and gets to humiliate him a bit as well. In the end, Sydney questions his identity.
All characters are 18 or older. Tags include feminization, crossdressing, pegging, femdom, mff, incest.
~~~~~
Angie loved to bully her little brother Sidney. Perhaps it was the adorable way he whined, or the girly way he pouted. Or maybe it was the power surge she got from the ease at which she could manipulate him. Regardless there was a single reason that she refused to consider.
“Jealous?” She laughed at the suggestion. “Really? Of him?”
Her friend Ellen looked contemplative, “He is really cute. You know how many boys have tried asking him out? They didn’t even know he’s a he, you know?”
“Heh,” Angie laughed again, “Yea, what a sissy right?”
“I mean, how many boys have asked you out recently?” Ellen asked.
“Look.” Angie didn’t like how much sense Ellen was making. “He’s small, okay. Girly? Sure. But look at me!” She motioned to her body and spun around, “Almost a D cup!” She bragged. “And I’ve got twenty-twenty vision! Unlike Sidney four eyes.” She added. “And top of my class!”
“Ahem,”
“Well, tied with you.” She admitted. “You know what I mean.”
Ellen thoughtfully ran a hand through her blond hair, “Both of you have pretty black hair and blue yes, cute face, he’s short and flat yes, but in terms of temperament-” Angie raised an eyebrow, “A lot of boys feel threatened by you, I mean.” Ellen added, “You know, you can be a bit harsh!”
“I just speak my mind.” Angie shrugged. “You always get creepy when you talk like that by the way.” Ellen responded with a chuckle, “Anyway, I’m not a coward like my brother. He’s never even asked a girl out.”
“Well, actually-” Ellen paused and let Angie take a guess.
“No.”
“Yep.” Ellen giggled. “Just this morning. It looked like he was having a heart attack. It was so cute!”
“Did you tell him to fuck off?”
“I said I’d think about it.” She wiggled naughtily.
Angie was astounded, “Ellen!” She tried organizing the millions of reasons why this was terrible, “He’s only eighteen. And he’s my brother!” Angie reiterated, “What the hell?”
“Well, I’m not saying he’s really my usual type.” Ellen admitted, twirling some of her long hair around her pointer finger, “But I think I can have some fun with him.”
“What do you-” Angie stopped when she saw her friend give a crafty smile, “Oh.” Angie understood. “Oh, what are you planning?”
“Well,” Ellen leaned in close and began to whisper, “Actually, I’ve always been a bit envious of you. I’d love to get some pointers on how to have some fun with him.”
Angie’s temperament changed, “Oh, I have some ideas.” She leaned in and whispered even lower, “But only if I get to be a part of it.”
They discussed plans as Sidney waited anxiously for a text or call from Ellen. He’d seen her around the house over the summer as he waited for his first semester at the local community college. To hide his embarrassingly small shoulders, wide hips, and lack of muscle he wore a thick sweater down below his waist and jeans continued down from there. He adjusted his glasses and tried to concentrate on the textbook on his lap. It was a dense brick of equations for a class he wouldn’t have to take for another year, but learning was fun for him. He only regretted that his hormones forced his mind to pursue other interests.
He thought of Ellen the way he saw her just yesterday. She and his sister had gone jogging in tight black spandex shorts and thin running shirts. His sister had returned exhausted, heaving, and bouncing in an unseemly way. Ellen had returned with a sweat oiled, tight, lean body. The sun shone from her slick skin and her athletic body was strong and thin above her full hips. She had given Sidney a look that he still dreamed about. He couldn’t tell if it was one of a predator, or prey, but it was inviting and terrifying all at the same time.
Suddenly, he got a call. He fumbled with the phone before answering, “E-Ellen? Yes, it’s Sidney.”
“Hi! So, I was thinking about our date-” Sidney gulped. His hands were already sweaty. “I wont really be free for the next few weeks. Really busy with back-to-school stuff. I don’t think I’ll be able to get to a movie or go out for dinner.” His heart sank, but he also felt a wave of relief. “But, I think I can make a compromise.” His heart beat rapidly once more. “I’m going to have a sleepover with your sister, and I was wondering if you wanted to come too!”
“That’s, uh,” Sidney wasn’t sure what to make of that.
“We haven’t had one in ages, but I’d really like to you come!” She continued, “I just got some new pajamas, and wanted to show them off.” She said it with such a tone that Sidney wasn’t sure if it was flirting or not, “Were going to have so much fun!”
“That’s,” Sidney paused, “Great.” He scratched his head, “So, that means, my sister will be there,” His voice was pitched high in a whine, or a question, “at our” he hesitated Ümraniye Yabancı Escort before he use the word, “date?”
“Sidney.” She said seriously. He listened carefully, “I know how weird this idea is, but I want you to know that my type of guy is,” He heard her take in a deep breath before continuing, “Brave.” She said soundly. “If you can do this for me, I’ll really appreciate it. I really do want to get to know you better.”
“I don’t know.” Sidney was fidgeting. This sounded like a trap.
“I understand. Your sister can be scary. We should both just concentrate on our studies-“
“I’m not scared.” Sidney lied.
“Great!” He heard her quickly add, “My place at seven, don’t be late!” And then the phone clicked. Sidney groaned and fell back on the bed. This was going to be so weird. But it was going to be his first date with a girl. He sighed, he’d heard most guys liked to pretend their first date didn’t count. He might as well get it over with.
—
“Sidney!” Ellen had her hair down, her green eyes almost glowed in the dark. Her silk pajamas were breathtaking. He could see bits of bare flesh between buttons. He swallowed hard. “Come on in!”
She did seem happy to see him. “S-So,” He asked just as the door was locked behind him, “What are we going to do?”
“First things first,” Sidney flinched when he heard his sisters voice. He turned and saw her. She was judgmentally looking down at him with disdain. Her own pajamas strained against her womanly assets and Sidney tried not to notice. Then, suddenly, she smiled, “Makeovers!”
“M-Makeovers?” Sidney blinked.
“Of course!” Ellen stood close to Sidney, about his height. She was almost touching him. “We already did each other before you got here.” Sidney realized how pretty she looked with her eyes outlined, face blushed, and lips a dark red.
“Look, I don’t know about this.” Sidney started. He felt like the walls were closing in on him. “Maybe I should-“
“Sidney.” Ellen looked nervous. “Can I talk to you in private?” Sidney looked to his sister. She seemed upset but walked away in a huff. Sidney sighed as she left the room. He looked at Ellen and nodded. She took his hand and bit her lip in anxiety. She led him to a nearby closet and squeezed them both in. She closed the door and in the darkness he could barely make out her form. It quickly became hot and sweaty.
He could hear his own heartbeat as he let her speak, “This is really big.” She started with a whisper, still holding his hand, “This has always been a girls-only thing you know? And it wasn’t easy for me to change that, and convince your sister to let you come. I did it because I really wanted to see you.”
“Oh.” Sidney felt a little guilty for being ungrateful.
“But.” Ellen spoke quietly and cutely, “I convinced her you could come if you agreed to be an honorary girl for the night.”
“W-What does that mean?” Sidney gulped.
“Just doing all the things we usually do.” Ellen giggled. “I know that you are sensitive about, well, being a bit sensitive.” He twitched, “But I think that’s sweet, and I really like that about you. If you can be brave enough to try this with me, well,” She stepped even closer to him, close enough to kiss, “Maybe I could be brave enough to try new things too.” He could feel her chest on his. The two sides of his brain fought one another for dominance.
“Okay.” Sidney’s cock had made the deciding vote. He nodded. “Honorary girl. Got it.”
“Great!” She opened the door to let the cool air in. “Here!” She took his bag and gave him another, “Try this on! Don’t worry, your sister told me your size.” She left him alone in the closet.
“You bought this for me?”
“Couples give each other gifts right?” Ellen said with false naivete. “Go on! I want to see how it fits! I have a lot more where that came from!”
Playing dress up was not on Sidney’s list of fun activities. He grimaced as she closed the door before turning on the closet light and taking a look at the clothing. It was in fact his size, but he groaned when he noticed the tags, “These are girls Pajamas!” He said from inside the room.
“What? Really?” He couldn’t tell if Ellen was surprised or not, “Oh, I’m sorry, I didn’t realize! Does it still fit?”
“Well, yea, but-“
“Just put them on!” he heard his sister order. He had agreed to be an honorary girl.
He was unhappy but willing. “Hey!” He felt a chill when he saw something else in the bag, “Uh, I think you left your underwear in here!”
“I bought that for you too.” Ellen’s voice seemed demure, sweet, and scared, “Is- Is that okay?” She mumbled. He wondered if that stutter was an act. He looked down at the underwear. It would actually fit perfectly, and it seemed expensive.
He grumbled as he stripped and changed. His junk was snug, and he wasn’t use to the way the cloth curved around his rear or pushed lightly on his lungs. He didn’t like how high the shorts were, or how his midriff and bra straps showed under the pink tank top.
“You’re beautiful!” He heard as he stepped out. Ümraniye Yeni Escort He was very aware of how horizontal his chest had become, and how much more air he felt around his thighs and stomach. The baby blue shorts legs were higher than his wrists and barely hid the panties underneath. He tried to be a good sport about it and pretend he didn’t care too much. “Lets do her hair next!” Ellen was giddy and bouncing. Sidney was happy that she was happy. He guessed that they were changing his pronouns. He sighed. No going back now.
Sidney tried to enjoy getting his hair and nails done. “Hey,” he heard his sister say as a ribbon was tied into a bow on the side of his scalp, “If Sidney is an honorary girl, does that make her my sister?” She smiled. Sidney rolled his eyes. “That’s means he’s my little sissy!” She chuckled. Somehow he knew that this was going to be a long night.
“Next,” Ellen took out a razor, “Your legs!”
“A-are you sure?” Sidney stuttered.
“I want you to be as cute and cuddly as can be!” She begged. Sidney whined. “See,” He saw her stand and put her hands on her own long pajama pants. Without any warning she pulled them down to her knees. “Smooth, and pretty,” She grabbed his hand and put it between her legs to feel her skin, “Like this.”
“Ah.” Sidney gulped, trying not to look at her panties and trying to suppress the manhood in his shorts. “Right.” Was this really how girls acted with other girls?
“You getting exited little sissy?” Angie smirked. Sidney covered his crotch.
Ellen took his hand away from her legs and lifted her pants once more. “Off with the shorts!”
He did not fight back as she lowered his pants and revealed the bulge in his panties. She wet his legs and he tried not to make eye contact as she made sure his thighs were moist and ready. She spread his legs and he felt far too open and vulnerable. His sister giggled and watched. Ellen’s hands felt cold. Once he was ready she took the blade from the shelf and began to cut. He felt metal on his ankle and felt her shave up to his knees, and then from there to his modesty. She was neat and delicate, touching him lovingly and carefully. He was more scared and embarrassed the higher she went. He felt her fingers fondle the seams of the panties as she stretched the skin and ran the silver razor across.
“Done!” Ellen clapped her hands. “Look!” She was delighted to give Sidney the hand mirror. Sidney was scared to look, but did so slowly. Sidney saw a very cute girl wearing his glasses and features. She had a bow in her hair and a blush on her face. She looked nervous, scared even at her own reflection. They had even darkened her eyes and brightened her lips and cheeks. Her throat went tight upon seeing what was written on her shirt. Her hot pink top had the words, “Dirty Girl” written across her tiny tits in glittering sequin letters. Her midriff was lean and curved into tight hips with smooth, long, pale legs. The only strange thing about her was the bump that pulled the panties tight and strained against the fabric. Sydney pulled the shorts back up. The girl in the reflection was almost crying. She tried to desperately cover the manly part. “She’s so cute!” Ellen hugged Sidney from the side, pressing herself into him. Her arms were strong and tight. It was uncomfortable, but immensely pleasurable. She cuddled him like he was a toy and let him go with a kiss on the cheek. She was as happy as could be. Sidney wanted to make her happier, despite his embarrassment.
“N-Not that cute!” Angie seemed insulted. “He’s-” She coughed, “She’s just my little sissy. She can’t be that pretty!”
“I don’t know.” Ellen smiled, not letting go, “The boys like her more. And she’s pure, and cute, and sweet, and look at that blush!” Sidney was both happy and humiliated in her arms and by her complements. It was the closest he’d been to a girl. He felt his manhood awakening in her clutches and tried desperately to hold it down. “I bet If I text her picture, and yours, to anyone on my contacts, any of them would say Sidney’s cuter.”
“You’re on!” Angie grinned aggressively. “What’s the wager?”
“D-Do I have a say in-” Sidney whined.
“Hush sweat baby.” Ellen stroked his head. He obeyed. “How about,” Ellen thought for a moment, “If I win the bet, you go topless for the rest of the night!”
“Ew, in front of my sissy? No one wants to see that!”
“If you win, I’ll do it.” Sidney breathlessly felt Ellen cuddle closer to him. “I’ll go topless for the rest of the night!”
“Fine, but I get to choose who you send it to!” Ellen released Sidney and handed her phone to her friend. Angie searched, “Yea, here, this guy!”
“Hey! Didn’t you date him a year ago? I think that’s a bit unfair.”
“You giving up?”
Ellen’s competitive grin showed fierce and she took the phone back, “Strike a pose!” Angie smiled, blew a kiss to the screen and gave a peace sign. “Now you!” She turned the screen to Sidney. He stood and clasped his fists together at his waist over his shorts. He smiled and turned his head. “Adorable.”
“Well? Verdict?” Ümraniye Masaj Salonu Angie asked before the text had even been sent.
“And-” Ellen sent the message. “We just have to wait till,” A ping announced the reply. Ellen held her mouth and gasped, then burst out laughing, “He asked for Sidney’s number!” Sidney really hoped she wouldn’t give it.
“Th-That’s not an answer!” Angie protested. Ellen was almost laughing to hard to stand after another text, “W-What?”
“I said that’s Angie’s sister, and he said he chose the wrong one!”
“W-Well-” Angie looked down in defeat. “Fuck him. What does he know?” In her defense, Sidney didn’t feel great about that statement either.
“Pay up.” Ellen smiled flirtatiously.
“Jesus Ellen,” Angie seemed uncomfortable. “Sometimes you weird me out. In front of Sidney?” Angie met his eyes and then sighed, “A bets a bet,” She unbuttoned and lifted her shirt. She wore nothing underneath. Her puppies barreled out and bounced when she fixed her hair. After a moment of thought she decided it would be more graceful to keep her hands on her wide hips and not even try to cover herself.
“Well.” Angie awkwardly tried to face Sidney with pride, and Sidney tried to find something other than his sister’s tits to stare at, “I guess we need to settle this score!”
“What do you mean?” Ellen grinned in victory.
“You think you are so hot.” Angie grinned, “I bet he’ll say my sissy is way hotter than you too!”
“Are you serious?” Ellen asked raising an eyebrow.
“Loser goes bottomless.”
“W-Wait a minute!” Sidney tried to stop the bet, “I’m not sure if I like where this is going!”
“Sure,” Ellen thought about it more, “I think that’s fair.” She gave a duck face and sent it. Sidney wondered silently if she even cared. “Well.” She grimaced. “At least he was polite about it.”
“Hah!” Angie’s breasts shook when she pointed, “Pay up!” Ellen rose and slowly let her bottoms cascade down her ass and let them drop to her ankles. He’d seen it before, but seeing it again, and knowing he’d see more, told his dick all it needed to know. She toyed with her panties and made sure to cover all her naughty bits along the way to keep Sidney from having a good look. He was having a terrible time keeping his manhood down as Ellen put her butt to the wall and shyly, coo’ed, “There, we good?”
Angie looked at Sidney. “You like the show numb nuts?” Sidney didn’t know what to say.
“Don’t be so mean.” Ellen wiggled, half seductively and half embarrassed.
“I bet that pervert is turned on right now.” Angie accused. Sidney swallowed hard.
“My pure little angle?” Ellen looked to him expectantly.
“N-No I’m not!” Sidney tried defending himself.
“Then it’s a bet!” Angie smiled. Sidney’s blood went cold. “If I see a boner, you have to show it, and Ellen shaves it too! If not, I’ll go buck naked.”
“Th-That’s not fair!” Sidney cried out. He knew what they would see if he removed his fists from his groin.
“So you are a pervert! A perverted little sissy!”
“Sh-Shut up!”
“It’s okay.” He heard Ellen speak up. He turned to her. She shyly eased her hands from her waist and showed her shaved clean womanhood glistening in the light. Her smooth thighs were dripping. Sidney was speechless, “I’m turned on too.”
“Oh my god ew gross.” Angie turned away.
“Show me.” Ellen looked down at Sidney’s crotch. He was on the brink of tears, but he obeyed and let his hands fall to his sides. His little pecker was pointing up and out at attention. “Now pay up.” She continued. He bit his lip and slowly lowered the waistband to show his pulsing manhood peaking out from under the elastic.
“Shit, I forgot it was that small.” His sister laughed. It was about four inches. He tried not to cry. “And, wow, you shaved it yourself already?”
“I-It’s sanitary!” He tried to defend himself and his bare balls.
“It’s cute.” He heard Ellen murmur. Sidney tried to take it as a complement.
“Hey Sidney, I have another bet for you.” Angie barked. Sidney was listening. “I bet-” Sidney bit his lower lip in anticipation. She grinned smugly, “I bet you wont last a minute if Ellen give you a handjob.”
Sidney’s cold blood cemented into ice. “W-What?”
“I’ve heard you in the shower in the mornings. Sometimes it’s even less!” Sidney was aghast. He looked at Ellen, but she avoided eye contact. She was giggling to herself and peaking glances at Sidney’s tiny cock.
“Keep me out of this.” Ellen said in-between chuckles, “Though-“
“Thought what?” Angie asked.
“No, never mind.” Ellen rolled her eyes, “I was going to say you should do it, but it’s obvious you can’t please a man.”
“Ew. And what?” Angie was disgusted and insulted. “No. I’m not going to jack off Sissy Sidney over here. But if I did, he’d get off in seconds I assure you.”
“Wanna bet?” Angie was very uncomfortable. Ellen was licking her lips. She really was a weirdo. Did Sidney really want a piece of her? “We’ll make it a three way- bet I mean.” She giggled madly, “Angie, if you can’t get him off, I’ll let him put whatever he wants, wherever he wants in me.” Sidney was slack jawed. She looked over him hungrily, “And if you do get him off, I get to put whatever I want, where ever I want in him.” Sidney felt his cock twitch in the air. “You don’t lose anything either way Angie.”
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