Eddie Miller was Ollie's roommate. They'd been randomly assigned together on the LGBT-friendly floor and had hit it off from the beginning. They bonded over their shared love of makeup, video and music production, and queer lit. Compared to Ollie's petite frame, Eddie was a tall and lanky boy with a sharp face and big green eyes with curly light brown hair. He had a slight British accent from his childhood and was always up for having fun, which made him an easy friend for Ollie to make in his new surroundings.
At first, Ollie was timid and reserved when he arrived on campus; but Eddie saw potential in him that no one else did. He encouraged Ollie to express himself more freely through fashion, makeup, and gender exploration - something they both enjoyed doing together in their room. Eddie loved getting Ollie to come out of his shell and prance around their floor together like fools. Ollie enjoyed Eddie's unapologetic confidence and queerness, and was clearly envious of his sexual experiences.
One night in mid-October, Eddie was in bed on his phone after a late film class when Ollie came home from a gay mixer event in tears, pale as a ghost. When Eddie asked him what happened, all Ollie would tell him was that he'd had a tough night and needed to think. Eddie pressed him, but Ollie clearly wasn't ready to talk.
Eddie noticed a change in Ollie after that night. On the one hand he seemed more confident and independent; yet somehow he became more distant at the same time, like he'd built walls around himself that even Eddie wasn't allowed inside. He knew better than to press him too hard, so he tried to give Ollie space and be understanding of what had happened - whatever it was.
Ollie's affect changed again a week later; he still seemed more confident, but he'd often zone out with a sparkle in his eyes and flushed cheeks.
'Aha!' Ollie thought. 'So it's a boy,' as Ollie absentmindedly spun back and forth in his desk chair with a content face staring off into nothing.
"So," Eddie asked tentatively, "who's this guy?"
Ollie was surprised by Eddie's question, his eyes wide with shock. He hadn't expected his roommate to pick up on the subtle changes in him so quickly.
"What guy?" he asked, trying to play dumb as he shifted in his chair and avoided eye contact.
Eddie just smiled and said "Come on, I can see it all over your face!" He gestured at Ollie's flushed cheeks. "You don't need to be embarrassed," Eddie continued reassuringly. "I'm here for you no matter what."
Finally, Ollie sighed dreamily. "His name is Tyler," he said with a mischievous grin, "and I think I'm addicted to him." His voice was low and trembling as if he were trying not to give away too much emotion.
Eddie raised an eyebrow skeptically. "Addicted? What do you mean?"
Ollie blushed and shifted uncomfortably on the bed before finally looking up at Eddie with big blue eyes filled with longing. "He...he makes me feel so alive when we're together," Ollie began hesitantly, but words began spilling out faster as his excitement grew, "We've only been seeing each other for a couple weeks but already I can't get enough of him! He's like my drug; every time we kiss or touch it feels like electricity running through me!"
Eddie smiled knowingly; so it sounded like this Tyler had taken Ollie's v-card and now he was riding high. He gave his friend an encouraging nod before gesturing for him to continue talking.
"He's so hot," Ollie said, his voice heavy with desire. "Like... SO hot, Eddie. And you would not believe how big his cock is. It's like, seriously huge!" He fanned himself with one hand and Eddie couldn't help but chuckle at his enthusiasm.
"He, like, trained me how to take his whole cock down my throat, it's so wild," Ollie continued, his voice full of awe as he lightly clutched his throat with his hand. "And then he made me put in this huge butt plug to train my ass and get me ready for his cock. I was so desperate for him to fuck me." His cheeks were flushed and Eddie could tell that just talking about it was turning him on.
"And then," Ollie said, leaning in close and lowering his voice conspiratorially, "he gave me poppers for the first time as we fucked - oh man! It felt so amazing when he filled me up with every inch; I swear sometimes I thought I was going to pass out from the pleasure!" He shivered at the memory, his eyes distant as if he were reliving the experience again.
Eddie listened in awe. It was clear that Ollie had found something truly special with this Tyler guy, and he couldn't help but be a bit envious - and aroused.
"He's so possessive," Ollie said with a sigh, his eyes softening at the thought. "It's like I'm the only one who exists for him when we're together; he looks at me and touches me and talks to me like he owns me!"
Eddie smiled softly as his friend continued to talk, but his words set off a red flag in his mind. He had seen how intense relationships could take a turn and how things could get out of hand if both parties weren't careful. Eddie knew that this guy had taken Ollie's virginity; he hoped Ollie wasn't getting in too fast too deep with this more experienced guy.
"Are you sure this is what you want?" Eddie asked cautiously, not wanting to sound too judgmental or unsupportive. "I just want to make sure that whatever happens between you two stays healthy and consensual."
Ollie nodded earnestly, his cheeks flushing slightly under Eddie's gaze. "Yes," he said firmly, determination glinting in his eyes. "I know it might seem strange but I really do love it - I feel safe with him like nothing else matters."
Eddie accepts that but he's still nervous. "So how did you meet this guy anyway? I can't believe this is the first I'm hearing about this, boo! I mean I thought you'd have come running to tell me when you lost your virginity!" Ollie blushed deeper as Eddie's words sunk in. He knew his roommate was right; normally he told him everything! But this time had been different.
"Erm, yeah," Ollie said sheepishly, looking away from Eddie's gaze. "Well... it happened at that queer mixer I went to.. the one you couldn't go to..." His voice trailed off and he fidgeted with a pillow on his lap nervously. Eddie froze; the night of the mixer was when Ollie had come home in tears...
"Ollie," Eddie said slowly, carefully choosing his words. "Please tell me you and this guy... that it was consensual?" His heart raced as he waited for an answer; if Ollie had been hurt or taken advantage of by some stranger then Eddie would make sure the guy paid!
Ollie looked up at Eddie, his blue eyes sad and serious. He didn't say anything for a long time. "Yes," he said softly, almost with uncertainty. "Yes, it was consensual. It wasn't what I expected it to be, but... but now I want it. I want it so bad, Eddie."
Eddie let out a breath; So Ollie had found someone who could make him feel safe and alive; that was all that mattered. He smiled gently and reached out to give Ollie's hand an encouraging squeeze before pulling him into a hug.
Despite his relief Eddie still felt concerned; Tyler sounded like a dangerous and irresistible force in Ollie's life, and he still wasn't sure about what Ollie had said about the night of the mixer. The red flags were still waving in his mind. But Ollie seemed clear about what he wanted, and all he could do now was support and protect him as best he could as a friend and roommate. He hugged Ollie tight and whispered in his ear, "I'm here for you no matter what happens."
The next few weeks Ollie only saw Tyler twice. It was like Tyler was deliberately keeping him on edge so that when they finally would meet, Ollie was practically falling over himself to please him. Tyler kept training Ollie's submissive instincts and always left him absolutely ruined and dripping with cum.
It was shortly before Thanksgiving break and Ollie hadn't seen Tyler in nearly a week. He was starting to go crazy with need, but Tyler only gave minimal responses to his texts. When Ollie got a notice about a package for him in the Resident Director's office, he was confused; he hadn't ordered anything, nor had his parents said they were sending anything. He was surprised to find a fairly large box with no return address. As he carried it back to his room he noticed that the box smelled faintly of Tyler's cologne; as though the older boy had spritzed it before mailing it. His heart started to race as he wondered what was inside the box.
Ollie blushed as he opened the parcel, revealing a note from Tyler saying, "I know you like girly things, little twink. Try this. I want you over here wearing them soon." He could feel his face heating up as he unfolded the crisp white blouse and plaid skirt, along with knee-high white socks, garters, panties, and a long wavy brunette wig. A schoolgirl's outfit. A quality one. His hands shook slightly as he held each piece up to his reflection in the mirror.
He'd always liked feminine things, but hadn't really experimented much with genderbending fashion. Something about the idea of wearing these clothes for Tyler stirred something inside of him that was both exciting and embarrassing all at once. Finally mustering up enough courage to try it on, Ollie slowly began dressing himself in front of the mirror - starting with the pale pink panties that ran up his ass due to the ill-fit in the front -- not designed for a cock and balls to be taking up space. Then he put on the skirt which hugged his hips and ass just right. The pleating of the skirt fanned out from the structured waist and the hem fell only a few inches below the cup of his ass. He blushed as he turned back and forth, admiring his ass in the skirt before slipping into the snugly fitting white blouse; buttoning it up tightly against his chest.
Once finished dressing himself in all its components, Ollie stared at his reflection for what felt like an eternity before finally placing on the finishing touch - the soft brunette wig that cascaded wavy hair down past his shoulders; giving him an almost otherworldly femininity that left him breathless.
Suddenly Eddie burst through the door of their dorm room with a loud, enthusiastic "Ollie!" His eyes widened as he took in his roommate's transformation. Ollie had always been beautiful to Eddie, but this was something else entirely - like seeing a whole new side of him that Eddie hadn't known existed before now.
He couldn't help but giggle at how cute and embarrassed Ollie seemed; it only made him look even more adorable. He walked over to where Ollie stood nervously in front of the mirror and gave him an excited hug from behind, squeezing his petite frame tightly against himself as he said, "You look amazing, boo! I'm so proud of you for experimenting with your gender expression like this! Where did this even come from?"
Ollie blushed and explained the parcel from Tyler and what it contained. Eddie snatched the note and read it, smiling knowingly. "Oh hunny, he must be so into you if he sent you this," he said before pecking Ollie's cheek gently. "Can I do your makeup? You're gonna look sooo pretty!"
Ollie smiled and nodded, feeling a little more relaxed now that Eddie was here. As Eddie began to apply eye shadow, Ollie couldn't help but feel a strange sense of pride in his own femininity; something about all this definitely felt thrilling and he was glad he was brave enough to explore.
Eddie took his time applying eyes, blush, and lips for a natural but sexy look. When he was finished Ollie looked at his reflection in the mirror, blushing a little as he took in Eddie's handiwork. He was amazed at how different he looked; like a completely different person! He was beautiful! His cheeks were flushed and his eyes sparkled with excitement under the sultry fake lashes Eddie had applied.
"You look amazing, Ollie," Eddie said proudly. "I think you make an excellent trap!"
"What's a trap?" Ollie asked curiously, playing with his hair as he continued to stare at himself in the mirror. He had heard the term before but wasn't quite sure what it meant.
Eddie explained that a 'trap' is someone who looks like a cute girl but is actually a guy. "It's a part of gender expression that some people really enjoy exploring," he said. "It's not really like drag because it's not performance, and it's obvi not being trans. It's more about exploring genderplay in public but secretly. And you look so good! For real no one would ever guess you're a boy under there." Eddie playfully flipped up Ollie's skirt and laughed.
Ollie laughed back, blushing and thanked Eddie. He played with his hair and the hem of his skirt as he looked at himself in the mirror, feeling more confident than before. He did look pretty. And Eddie was damn good with makeup. He couldn't wait to show Tyler his new look!
Ollie nervously made his way up the stairs to Tyler's apartment, feeling a mixture of excitement and embarrassment. He had been so anxious walking from campus to the apartment in the school girl's uniform wondering if people knew that he was really a boy. He definitely caught some hungry looks from guys on his walk. When he got to the door, he hesitated for a moment before mustering up enough courage to knock. The door opened and there was Tyler, looking handsome as always in jeans and a fitted t-shirt that accentuated his muscular frame. His mouth fell open as he saw Ollie and the outfit he was wearing.
"Um... come in," Tyler said, his voice full of desire. He pulled Ollie into the apartment and closed the door behind him. His hands immediately went to Ollie's hips as he looked at him approvingly from head to toe.
"You look incredible, little Ollie," Tyler said, leaning in for a passionate kiss that left them both breathless. He ran his hands down Ollie's body before pulling away with a smirk on his face. "Let me see you twirl around," he commanded playfully, stepping back to watch as Ollie slowly spun around in front of him, feeling self-conscious but also aroused by Tyler's gaze on his body. He felt his little cock harden in the soft panties he had on under the skirt.
When Ollie finished spinning, Tyler stepped forward and pulled him into his arms. "You're so sexy," he murmured in Ollie's ear before pressing his lips against the boy's neck. "I love that you put this on for me." Ollie murmured happily in Tyler's arms, reveling in the praise. "Tell me baby," Tyler said huskily, looking Ollie in his eyes, sultry with makeup. "Do you want to wrap those pretty lips around your man's big cock?" Ollie felt a flush creeping up his neck and cheeks as he nodded, feeling unable to speak.
Tyler smiled down at Ollie as he slowly pushed him to his knees. He ran his hands through the long brown wig and curled one of Ollie's ringlets around his finger, marveling at how different he looked in that outfit.
"My little twink," Tyler murmured, brushing a gentle kiss on Ollie's forehead. "You make such a beautiful girl." He cupped Ollie's face in both of his hands before leaning down to press their lips together; the kiss was soft and slow - an invitation for more.
Pulling away from the kiss, Tyler held onto Ollie's cheeks with a tenderness that belied the roughness of what they were about to do next. His deep brown eyes locked into Ollie's big blue ones, swimming behind the lashes and eyeliner like stars shining brightly against a night sky.
"Are you ready?" Tyler asked quietly; not wanting to break whatever spell had been cast between them as they stared into each other's eyes.
Ollie nodded shyly before finally finding his voice again: "Yes, Tyler" he whispered, barely audible but still full of longing and desire for this man who was taking him past all boundaries he'd ever known before now. It had been too long. Ollie needed this.
Without another word, Tyler released his cock from his jeans and draped it across Ollie's painted face. It was huge, long and thick - a sight that made Ollie feel both intimidated and aroused all at once. He could smell the musky scent of Tyler's arousal emanating off of him; it was intoxicating
"Look how big I am compared to your face, baby," Tyler said; his cock covering Ollie's face from chin to forehead. Tyler rubbed his hard shaft along one cheek, over his nose and to the other side of his face. The smell of his musk was overpowering to Ollie.
Slowly, Tyler began to run the tip of his dick along Ollie's lips, teasing them into submission as he looked down upon him with an intensity that left no room for doubt about what was going to happen next. Ollie opened his mouth slightly, letting out little whimpers as Tyler continued to trace circles around his soft lips with the head of his cock.
"Go ahead," Tyler said in a low voice. "Take me into your mouth, baby girl." He ran one hand through Ollie's wig while placing the other on the back of his head, gently guiding him towards taking all of Tyler inside himself.
Ollie closed his eyes, finally taking him in between his lips and sliding his mouth down Tyler's cock. He felt his throat stretch around Tyler's cock as he took it deeper and deeper into himself, his lipstick-coated lips sliding down the thick shaft as his done-up eyes looked up at Tyler, watering from the exertion.
Tyler groaned in pleasure, running his fingers through Ollie's wig and gripping the back of his head firmly as he thrust himself into Ollie's throat. He felt like he was about to burst from all the pleasure that was coursing through him - it was overwhelming and beautiful at the same time.
He looked down at the trap beneath him; his little twink with a big cock in his mouth. It was pure perfection, and Tyler knew that Ollie would do anything he asked of him now. As Ollie sucked Tyler's cock in his trap outfit, Tyler began to dirty talk about Ollie being a pretty girl.
"That's it baby doll," he said in a low voice full of lust. "Take all of me into your pretty mouth; show me how much you want it."
Ollie felt like a slut in the outfit, sucking Tyler's big cock. But he loved it; he loved how dirty and naughty Tyler was making him feel - it was as if all of his inhibitions had melted away in that one moment.
Tyler continued to talk dirtier and dirtier, pushing Ollie further and further into subspace with each word. "That's my girl," he said gruffly. "You love sucking this big dick don't you? You want me to fuck your tight little pussy?"
Ollie moaned in response, the words making his cock twitch with pleasure in the girly underwear. He felt like he was melting into a puddle of pure ecstasy as he bobbed on Tyler's cock and he kept talking to him.
"You love being my little slut. You want me to fuck you hard and take all of your innocence away?" Ollie's eyes fluttered at these words, feeling heat rush through his body at the thought of Tyler dominating him so completely.
He pulled his mouth off the slick cock, dripping with thick drool. "Yes," he whispered, barely audible but enough for Tyler to hear.
Tyler smiled and grabbed Ollie's chin, pulling him up for a passionate kiss. "You're so fucking beautiful," he said against his lips.
As Tyler's hand moved under Ollie's skirt, he felt a wave of arousal course through his body. He looked up at Tyler and saw the same hunger in his eyes that he was feeling himself; it made him feel more alive than ever before. His breathing quickened as Tyler teased the soft skin of his inner thighs with gentle strokes.
Tyler leaned down and kissed Ollie deeply, exploring every inch of his mouth with passionate intensity. His hands kept playing underneath the fabric teasingly, making Ollie moan against him.
"You like this don't you, baby girl?" asked Tyler as he pulled aside the panties to slip a finger inside of Ollie's tight hole.
"Mmmhmmm," moaned Ollie in response, pushing back against Tyler's finger.
Ollie shivered as Tyler explored his ass with one hand, and teased his little cock with the other. His breathing quickened as Tyler slipped in a second finger, expertly moving in and out, slowly stretching him open until he was moaning.
Tyler loved how his little trap twink reacted to his touch; the way he would moan and push back against him, begging for more. He felt a thrill run through him as Ollie shivered under his hands, feeling truly alive in that moment.
He pushed his fingers deeper inside of Ollie's tight hole, gradually increasing the depth until he felt like he was about to come undone from pleasure. Tyler watched with delight as Ollie moaned louder and louder from Tyler's ministrations, pushing himself further and further into subspace until Tyler could feel every inch of him quivering beneath him.
"You're so fucking hot, baby doll" Tyler murmured between kisses as he continued to curl his fingers into Ollie's prostate.
Tyler pulled his fingers out and pushed Ollie onto the bed. His hands moved down to unbutton Ollie's blouse; revealing what was underneath - two small pert nipples on a slender chest. He leaned in to take one of them into his mouth as he spread Ollie's legs wider apart with his free hand.
Tyler slowly slipped Ollie's panties down, leaving the skirt on as he admired the twink's body. Ollie felt exposed and vulnerable in this position; a twink boy in a wig and a skirt with his cock out and his asshole twitching from anticipation. He could feel Tyler's eyes burning into him as he moved lower, kissing down Ollie's stomach before finally reaching his hard little cock.
Tyler licked up the length of it, swirling his tongue around its tip before taking it all into his mouth at once; causing Ollie to gasp at the sudden sensation. "You like it when I suck your little clit, baby girl?" Tyler said.
Ollie nodded, unable to form words as Tyler continued to pleasure him with his mouth and talk to him like he was a girl. He felt like he was going to explode at any moment; the sensations were too much for him to handle.
"You want me to eat your tight little pussy, baby?" Tyler said, stroking Ollie's cock lightly.
"Fuck yes," Ollie whimpered, his voice barely audible through the pleasure.
"Yes what, baby doll?" Tyler asked.
"Yes daddy!" Ollie said.
Tyler smiled in surprise as he heard Ollie call him daddy. The twink was really getting into the roleplay. He moved his hands to Ollie's hips and flipped him over onto all fours; he lifted the skirt and grabbed hold of his ass cheeks, pulling them apart gently.
"Say it again," Tyler said in a low voice. "Tell me what you want, baby." He gently blows cool air on Ollie's tight hole.
"Yes Daddy! Please eat my tight little pussy." Ollie moaned, squirming in pleasure as Tyler's skilled fingers lightly teased his tight hole.
"That's my good girl," Tyler said before dragging his hot wet tongue over Ollie's asshole. Ollie gasped, feeling like he was going to lose his mind from the pleasure. He grabbed onto the sheets as Tyler licked and sucked him into oblivion.
"Your pussy tastes so good baby," Tyler murmured between licks. Ollie loved how Tyler's tongue felt on his ass and his mind warped as he called his asshole a pussy. He was almost at the brink of orgasm when Tyler finally stopped and pulled away.
Tyler smiled as he watched Ollie's body tremble in pleasure; his little twink had been so responsive to all his dirty talk, it made him want to do more. But for now, he wanted to make sure that Ollie would never forget this night - the night his Daddy turned him into a slutty trap girl.
"You ready for Daddy's big cock to fuck your little pussy, baby?" Tyler said, his voice dripping with lust. Ollie nodded eagerly in response, feeling a thrill of anticipation at the thought of being taken by Tyler while in the skirt.
"Good girl," Tyler said as he climbed on top of Ollie and lined himself up between his legs. He grabbed hold of Ollie's hips tightly before pushing himself inside; slowly sliding his slick cock into him until he filled every inch of his ass.
Ollie gasped loudly as he felt all 9 inches of Tyler slide into him; it was probably too much for him to take without more prep but he couldn't help but moan in pleasure despite the pain.
"You like this baby girl?" Tyler asked huskily; his thrusts becoming harder and faster as Ollie's body writhed beneath him. "You like having Daddy's big cock in your slutty pussy?"
"Fuck yes, Daddy!" Ollie said, as his eyes rolled back into his head from the overwhelming stretch in his ass. Tyler smiled as he continued to slowly thrust deep inside of Ollie.
"You want me to put a baby in you? My thick seed planting inside your womb?" Tyler asked, his voice low and full of lust.
Ollie felt himself get lost in the fantasy of being a girl; his body trembling and twitching with pleasure as Tyler thrust deeper and harder inside of him. His mind drifted away to another place, one where he was truly female - complete with a womb that could grow new life from his Daddy's seed.
"Yes," Ollie whispered breathlessly, playing along with Tyler. "I want your baby inside me."
Tyler felt his cock swell with pleasure as Ollie whispered the words he had been longing to hear. He grabbed onto Ollie's hips and started thrusting into him harder and faster, letting out a loud groan of pleasure with each movement.
"Fuck yeah you slut," Tyler said, pushing himself even deeper inside. "Take all of my huge cock; I'm gonna make sure you're pregnant with my son, baby."
Ollie moaned in response; his body trembling beneath Tyler's powerful thrusts as he felt himself getting closer and closer to orgasm. He could feel every inch of Tyler's thick throbbing shaft penetrating deep within him and it was almost too much for him to take without releasing a scream of pure ecstasy.
"Fuck me, Daddy!" Ollie begged desperately, his voice becoming more desperate with each word. His eyes were closed tightly as he imagined being taken by this strong alpha male who wanted nothing more than impregnating him with their own child - something that made Ollie feel both scared and excited at the same time as he imagined being a woman.
"Put a baby in my pussy," Ollie whined, his voice trembling with pleasure as Tyler continued to thrust inside of him.
Tyler groaned as he felt himself getting close; the thought of planting his seed deep within Ollie's tight little pussy was too much for him to handle. He let out a loud moan and grabbed onto Ollie's hips tightly, pushing himself into him harder and faster until he could no longer hold back.
"Take it all, baby girl!" Tyler shouted before finally cumming a massive load in Ollie's boy hole.
Ollie gasped as he felt Tyler's thick cum filling him up; his body trembling with pleasure at the sensation of being filled by this alpha male. He felt like a new person - one who was no longer scared of taking on any challenge that life threw at them.
Tyler pulled out slowly before collapsing beside Ollie, panting heavily from the intense experience. "That was amazing," he whispered breathlessly, pulling Ollie closer to him for an embrace.
"Yes it was," Ollie replied sleepily, snuggling into Tyler's chest and feeling safe in his arms. Tyler held Ollie close in his arms, feeling a deep satisfaction as he looked down at his beautiful femboy looking like jailbait in the open blouse and skirt with cum seeping out of his ass.
"You're mine," he said possessively, squeezing Ollie's ass as they both smiled.