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(Disclaimer: All characters are 18+. These stories are based on fiction and fantasy, never on reality. If you don’t enjoy themes of incest, femdom, sissification, gay encounters, and cross-dressing…this story may not be for you.)
*****
Kylie woke up to the cool Autumn morning air filtering into his room. He didn’t remember opening his window last night. That’s when he heard his curtains open, and he became temporarily blind as his eyes adjusted to the early sun.
“Rise and shine, sissy! Today’s gonna be a great day!” His sister Ava exclaimed and she threw open the blinds, letting the sun filter into his room. Kylie squinted through his eyes to see his sister trotting around his room in a pair of his old boy briefs and a purple and orange training bra.
“Ugh it’s too early… I still have more time to sleep.” Kylie said looking at his alarm clock. It was Friday, the best day of the week.
“No babe, you have to wake up and get all sissy’ed up for the day just like all the other girls do. We’re getting you ready to be the best girl ever, remember? So you need to get up!” Ava said in a sing song voice. As she said this, she ripped the covers off her sissy brother, exposing his extremely hard morning boner in his panties. Kylie’s hands shot down to cover his erection.
“Oh… well we’re gonna need to take care of that before you start getting dressed.” Ava said in a naughty tone. “Stay right here, I’ll be right back.” And the sexy sister bounced off to her room. Kylie rubbed his swollen cock a little, remembering the dream he was having about jerking off Brandon in the locker room. He sighed at his perverted thoughts as his sister walked back in the room.
“Okay sweetie, I’m gonna show you how girl’s like to get off, okay?” Ava said, holding a long, pink instrument with a round, rubber top and had several buttons on the sides.
“Is that… is that what I think it is?” Kylie asked shyly with wide eyes.
“Yep. This is my vibrator, Kylie. We’ll get you your own vibrator soon, but today we’ll have to be good sisters and share.” Ava said with a devious smile. “Now reach up and grab your headboard, and no matter what, do not let go.” Kylie saw her click a button and then heard the faithful BUZZZZZ of the vibrator.
“Okay, Ava. I’ll try my best.” Kylie said nervously.
“Honey, don’t be nervous. This will feel so good. Girls LOVE using these so you’ll need to get used to it. You can even leave your cute panties on.” Ava replied sweetly. She turned the vibrations to a steady medium pattern, and slowly touched it to the tip of her sissy brother’s cock.
Electric immediately shot through Kylie’s cock and balls, and spread through his legs and body. He tensed at the steady vibrations that racked his penis. He couldn’t believe how amazing this felt, and he wasn’t even touching himself.
“Oh my god! Ava… that feels so fucking good.” Kylie squealed and flexed his cock into the vibrator.
“Oh yeah? You really are such a good sissy for loving this vibrator. You’ll be a cute college girl in no time.” Ava quipped in a teasing tone. Kylie gripped his headboard with white knuckles as the vibrations brought him some of the most intense pleasure of his life. He moaned effeminately as his sister pressed the button to increase the vibration power by one notch.
“Ava… I had a dream last night.” Kylie heard himself say, not sure why he was admitting this but feeling compelled to tell his dominant older sister.
“Yeah? About what?” Ava pried, holding the vibrator on the very tip of her sissy brother’s cock, torturing him with pleasure.
“I dreamt that I was in the men’s locker room after one of the football games… and Brandon texted me to come jerk him off after everyone had left. So I came to his locker and totally jerked him off until he came all over the pl-pl-place.” Kylie said as his voice gave way at the vibration massaging his cock head.
Ava felt her own briefs get extremely damp at her sissy brother’s description of his dream. She shifted uncomfortably, feeling very aroused at the conversation.
“That’s a very dirty dream, Kylie. You must want his cock so bad.” Ava declared, rotating the vibrator around the head of Kylie’s cock.
“He’s just sooo hot. And he’s so cool and nice to me all the time.” Kylie admitted, realizing how much Brandon meant to him.
“Oooh sounds like somebody has their first crush on a boy!” Ava needled her sissy brother in a playful way.
“What? No I don’t! Brandon is with our sister Sammie, anyways.” Kylie blushed at the mention of having a crush on a boy. Ava abruptly shut off the vibrator and grabbed her brother’s cock and squeezed it aggressively.
“Ouch! Ava that hurts!” Kylie squealed in a feminine voice. He had been so close to cumming.
“Tell me how bad you want a real cock.” Ava said with venom in her voice. She was soaking her briefs at the domination of her brother.
“Ugh… I don’t know, Escort bayan okay!” Kylie said in a weak attempt to circumvent the question.
“Oh so you don’t want to cum? That’s fine by me.” She released his cock and started to walk away.
“No!! Okay… I want real cock so bad.” Kylie said in barely a whisper as his sister walked away. She turned back around.
“Say it louder.” She demanded, feeling a wet spot forming in her briefs.
“I want some real cock so bad, okay? I have dreams about it! But I like pussy too! Are you happy?” Kylie exclaimed in an embarrassing moment of desperation.
“Good sissy.” She said and lifted the front of his tight panties, exposing his incredibly hard cock in the front. She turned the vibrator to the highest power, jammed it down his panties and against his throbbing cock, and then let go of the waist band, trapping the vibrator under his panties. She took a step back, and watched the show.
Kylie gasped as his sister jammed the vibrator down his panties. She had perfectly lodged it against his cock head on the highest power, and he was already on edge from before. His cock flexed at the sudden stimulation, and then…it happened.
A massive orgasm tore through Kylie and he began spasming as his cock pumped rope after rope of thick cum into his panties. He gripped the bed sheets until his knuckles turned white, trying to ride out the most intense pleasure of his life. The vibrator continued to buzz away as his orgasm painted the inside of his precious girly panties that he had gotten from his mom. He imagined how many times her cum had soiled these panties, and it only redoubled the pleasure he was receiving.
Ava watched as her brother squirmed in the bed, the extremely powerful vibration causing him to lose control. She saw his eyes roll back, and his mouth drop open in a facial expression of pure ecstasy. She imagined this same look on his face as her strap-on cock pushed into him from behind and she nearly ruined her briefs, but gained her composure. There was a lot to do today! She needed to be on her toes.
Kylie came down from his incredible orgasm and felt his sensitive cock head being tortured by the vibrations. He whined and quickly pulled it out of the panties and tossed it on the bed at his side. He panted for air, trying to find his way back to earth from the cloud nine he had discovered. Ava grabbed her cum soaked vibrator and took it the bathroom to wash it off. She returned it to her underwear drawer, and gathered an outfit for Kylie.
“Oh. My. Gosh. I love that thing!” Kylie exclaimed as Ava stepped back into his room. She smiled and kissed her sissy brother on the cheek.
“Oh I could tell just from watching. You looked so sexy, Kylie.” She said in a soft purr and rubbed his thigh. “Okay, you need to get a shower now and I’ll help you get some light make-up on after that. But this will be your outfit for the day babe.” She laid it down on his gaming chair and went to get dress herself.
Kylie slowly rolled off his bed and examined the outfit laid out by his sister. The purple thong would be his panties for the day. He smiled at how perfect the color choice was for the October Halloween vibes. Then he saw the tight, spandex yoga leggings from Victoria’s Secret with “PINK” in big letters on the butt. Then for his shirt, a purple and white long sleeve cotton shirt with the same “PINK” branding on the arms and chest. His entire outfit was from the Victoria Secret clothing line.
Kylie felt nervous and excited at the thought of wearing this around campus. He was going to get so many looks from everyone in the form fitting, feminine outfit.
Kylie turned on the water to the walk-in shower and let it warm up. He stripped off his cum-soaked panties and threw them in his personal hamper that sat next to Ava’s. He couldn’t help but enjoy the sight of both his and his sister’s laundry hampers full of panties. He smiled and walked into the warm shower, letting it cascade down his chest and legs.
As he warmed up in the shower, Kylie thought about his new outfit for the day. Did he have the nerve to wear something so feminine, so quickly?
I mean he had just decided he would become a Sissy yesterday. What if he got a boner in the Victoria Secret leggings and it stuck out? He imagined walking out of class, his little sissy boner bouncing slightly side to side in the leggings as he tries to rush out of the room, passing the row of student-athletes would most certainly laugh at his situation. As he imagined this, he felt his cock growing in the shower. Despite just cumming from his sister’s excellent vibrator techniques, it was like he couldn’t keep his cock down recently. He heard Ava walk into the bathroom and he tried to hide his obvious erection.
“Kylie are you almost finished, hon?” Ava asked in a sing-song voice, peeking her head around the tile wall to look at her shaved, sissy brother. She spied his little Bayan escort cock standing at attention in the warm water. “Are you seriously already hard again? Thinking about some fat cock?” Ava teased her little brother relentlessly.
“Ugh, shut up! It’s just cuz of the warm water and since I’m all shaved now.” Kylie said weakly and smiled at his sister. He was so glad he had a sexy, powerful girl like her to help him through all of this.
“Suuuure, sissy.” Ava replied, smiling back at her cute sissy brother. She couldn’t keep her eyes off his cock. It might have been small, but it was so cute… and she loved playing and teasing with it. “Now come on out and get dried off so we can do your make-up.” She finished her sentence. Kylie turned off the warm water, letting the excess water run off his shaved body. He walked out of the large shower, and felt his cock bouncing ever so slightly as he stepped into the towel his sister had waiting for him. She dried off every portion of his body, making sure to spend a little too much time drying off his cock and balls. Kylie stood still and let his sister use the towel to both dry him off and tease his swollen cock.
“Okay, I think I’m all dry Ava…” Kylie said quietly as his sister spread his ass cheeks while pretending to dry him off. Kylie felt extremely self conscious about his sister pulling his butt cheeks apart and checking him out. Ava gave his bubble butt a firm slap that made him jump.
“Alright, cutie. Let’s do your make-up.” Ava said cheerfully. Kylie stepped to the mirror and pulled the towel around her chest and wrapped it tight, exactly like a college girl would do. He felt very feminine, and only got more excited when he looked down at his cock making a tent in the wrapped towel. He stood perfectly still as his sister worked her make-up magic.
“You’re gonna look so cute for your first day of school as a sissy, Kylie. Don’t worry, it’ll be light make-up until we can get your hair in a better feminine style to frame your cute face.” Ava said, applying a very soft, pale shade of pink on her sissy brother’s cheeks. She added a light shade of eyeshadow, and some stunning mascara that made Kylie’s eyes pop with their striking green color. It was the perfect amount of make-up to make Kylie look like a cute tomboy. “Oh, and I have a couple surprises coming for you in the mail. It should get here by this evening, Amazon is so fast usually.” Ava said and winked at her brother.
“Surprises? You didn’t have to get me anything, Ava.” Kylie said in a soft, kind voice.
“Oh let’s just say…they’ll be for the both of us.” Ava replied in sultry tone with a devious smile forming on her lips.
“Oh… that sounds… fun.” Kylie said and couldn’t help but look around nervously, feeling sort of like a girl being hit on by her horny boyfriend. Ava closed the door to the bathroom and talked in a more discreet voice level.
“So, I’m sure you’re worried about the tight leggings showing off your little package.” She said, reading Kylie’s mind almost perfectly. “But I did some research, and I have a perfect fix until we can get some of the things I ordered.” Ava told Kylie as she took a pink and purple cotton sock out of her make-up bag and a pair of scissors. She cut the soft, colorful sock in half, creating one long piece of material. She got down to her knees, eye level with Kylie’s cock.
“Spread your legs. I need to make sure this is done right.” Ava demanded, Kylie quickly following his sister’s orders and spreading his legs to provide her room to work. She cupped his cock and balls in one hand, making sure they stayed together as she had him hold one end of the cut up sock where his pubes would be if they weren’t shaved. She stretched the sock tightly under his legs, letting it encompass his small package and flatten it down. Then she taped the end of the sock to just above his butt cheeks, and then did the same to the end that Kylie had been holding over his penis, taping that down tightly. The tape would’ve been an issue if he hadn’t just shaved all his hair yesterday. But now, it was smooth and comfortable.
Kylie examined himself in the mirror and appreciated the work his sister had done. His small package was perfectly flattened down by the sock, creating a smooth effect that seemed like he had a feminine vagina down there. He felt himself getting around, and looked away in order to try and stop his erection. “Thank you so much, Ava. This will be perfect for my outfit today.” He hugged his sister tight in gratitude.
“It’s my pleasure, Kylie. I have a real gaff coming in the mail for you, so this makeshift one will have to do for a bit. Now go get dressed for the day.” She squeezed his ass cheek as she sent him off to get dressed.
Kylie skipped back to his room and let himself indulge in his sexy imagine in the full body mirror. He looked like a sexy girl, and it was driving him crazy to see that. The makeup and “cock Escort concealer” we’re perfect for his feminine body shape. He picked up the soft leggings off his bed and rubbed them, excited for the soft feeling of the material to be against his legs and butt all day.
He pulled the purple thong up his smooth legs and reveled in its tightness. He felt the thin strip of material contour to his body, making him feel sexy. He quickly grabbed the leggings and tugged them up his legs, feeling almost orgasmic at the first time wearing girl’s leggings. No wonder girls loved wearing these! They were so comfortable and rubbed him perfectly. He looked at his body in the mirror and was so excited he almost cheered when his groin was smooth and flat, like a girl’s. There wasn’t any bulge!
He turned around and checked out his ass in the tight pants. He could totally pass for a college girl with a bubble butt. He smiled and put on the purple and white Victoria Secret shirt. He loved the way it flowed down his body, sometimes catching the wind and exposing his midriff. He looked like the perfect college lady. Ava stepped into his room, wearing a pair of black jeans with holes in the thighs, and a t-shirt for the band “SLAYER.” She also had one very stylish black bead bracelets and a choker on her neck. She looked fabulous, and Kylie had always envied her impeccable fashion sense.
“Oh my gosh, you look so cute!” Came a voice from behind his sister Ava in the doorway. Kylie’s Mom peeked in the door and poured her eyes over her feminine son. “That is the perfect outfit for you, sweetie. Don’t let too many boys bother you, okay?” She kissed his forehead and headed back through his doorway, passing Ava. “Have a good day at college Ava… I’ll see you later tonight.” Riley Everson said with a hint of nerves to her voice. She let her hand linger for just a second too long on her daughter’s lower back, and then headed out to her office for the day. Ava smiled at the interaction, already knowing she had her Mom like putty in her hands.
“Ready for school, Kylie? You look gorgeous by the way. The leggings are perfect on your bottom.” Ava said, admiring her sissy brother in his first full girly outfit.
“Yes I think so… I’m just nervous. What will people think? I mean not that many people knew me before, but they’ll definitely notice me in this outfit.” Kylie said as his feminine voice shook with fear.
“Babe, don’t worry. I’ll be there if you need me. And plus, you’re a smoking hot girl. If anything, they’ll just want your number.” Ava said and smiled at her brother. Kylie couldn’t help but smile back at his sister’s encouraging words. He grabbed her hand and they marched to the car together, ready to face the world.
*****
Kylie and Ava arrived to campus with plenty of time before their first class. They sat in Ava’s Jeep Renegade and dipped coffee while they scrolled on their phones. They texted pictures of panties they both liked back and forth, and even gossiped about some of the boys who passed their car. At about 9:30am, Ava’s boyfriend Marcus came to the car.
Marcus was a really athletic, slim guy who was an avid rock climber. His forearms were like chiseled stone from all the upper body workouts he did to get better at climbing. He tapped on the window, and Ava rolled it down and kissed him deeply. Kylie thought he might feel jealous after kissing Ava so much the past day, but instead he immediately felt turned on by watching a strong guy like Marcus kiss his beautiful sister.
“Well hey there, Gorgeous. You look wonderful today.” Marcus complimented Ava, with an inviting smile on his face.
“Not so bad yourself, handsome.” Ava replied, pulling her backpack out of the car. Kylie got out and walked around the car to their side. Marcus immediately had a wide-eyed look like he knew it was Kyle under all that stuff but he couldn’t be sure. “Oh your remember my sister, Kylie.” Ava gave him a knowing look, asking him to follow her lead just with her eyes.
“Of course! Nice to see you, Kylie. You look very pretty today.” Marcus said, being kind during a strange situation.
“Oh thanks, Marcus.” Kylie said with a very feminine tone, blushing bright red as he thought about how he came all over himself while looking at at picture of Marcus’ cock yesterday.
Marcus looked at Kylie up and down, realizing that he really did find his girlfriend’s little brother very pretty. He shook it off and took Ava’s hand. “Ready for class?” He asked politely.
“Yeah, lets go. Have a good day, Kylie. Text me if you need anything.” Ava said kindly to her sissy brother, beginning to walk away towards class. Marcus looked back one last time, checking out Kylie’s bubble butt and shaking his head. Damn, Kylie looked good in those leggings.
Feeling confident at Marcus’ reaction, Kylie walked toward class with headphones in his ears. He listened to Frank Ocean while he tried to strut confidently across campus, feeling the mixture of eyes and reactions on him. He entered the building where his class was located, trying to keep a low profile as he made his way there. He was a little early, so he sat at one of the tables that butted against the wall in the hallway.