But now his secret was out. All of the guys knew it, and everyone who would win their spot in the Kappa Delta Pi fraternity would soon know it too. So there was no sense in not trying. He no longer had anything to lose—though his task seemed more or less impossible.
He had to go out and find a trans woman, have sex with her, and film it—and he only had six hours left to accomplish that goal. He had no idea where to start. He wasn’t even sure if he’d ever seen a trans woman outside of the Internet before—so even if he could find one, how was he going to convince her to sleep with him? And how was he going to convince her to let him film it? And what if he couldn’t go through with it? What if he saw her cock and froze up?
Louis had only ever been with one girl before, and even that was a stressful scenario. He couldn’t imaging being with a transgender, seeing a cock inches from his face. Even if he just flipped her over and stuck it in her ass—he would still know there was a cock dangling on the other side… What if he couldn’t come? It didn’t matter if he came or not—the task was to film sex. No one ever said anything about finishing…
He liked watching tranny porn—it was his go-to masturbation material. And it was a secret he’d kept hidden for many years, but it wasn’t entirely a secret anymore. He’d always gotten off to images of beautiful women with big, hard cocks. He especially loved videos where the trannies were on top, getting reach-arounds from their male dates. He never liked the videos where the guys were on top—they always made weird, uncomfortable faces. His favourite videos were when there were two trannies sucking each other off—but he’d always suspected the reality would be different. He’d always suspected touching a cock in real life would be much different than looking at one on a computer screen.
There were probably smells—manly smells that can’t be eliminated by hormones. Louis wasn’t sure how he would be able to look at a real life shemale and not imagine what she looked like before the surgeries and hormone replacement therapy. He liked his perfect porno fantasy and he didn’t want to ruin it with gross, smelly reality. But he had no choice; the clock was ticking and she still had no idea where to start.
He remembered the ads on the side of the pornography websites that said things like, ‘Want to fuck a real tranny? Join our site now and find the hottest local trannies!’ He always assumed they were just scams and click bait, but he was desperate. So he went and found one of those ads and clicked on it. He signed up for one of the websites, even paying the 10$ fee with his credit card. He quickly made a profile and then started scanning through local profiles. They all seemed fake, but he messaged a few of them anyway, paying 5$ per message. Within the next hour, he received a few responses. Louis got right to the point with the girls.
“I want to have sex tonight, and I want to film it. No one will see the footage—I promise.” But the trans girls he was talking to didn’t give him a straight response. They just wanted to continue talking, at 5$ per message. Louis realized he was being scammed, so he closed the website and tried not to think of the fact he’d just spent over fifty dollars messaging fake trannies.
But what else could he do? How was he supposed to accomplish his task? The only solution he could think of was to beg a gay male friend to dress up like a girl and go along with it—but then Louis would have to have gay sex with a guy dressed as a woman But how was that any different from having sex with a tranny? Was a tranny not just a gay man dressed as a woman?
Louis couldn’t bare the thought. He sunk back down onto his bed and stared up at the ceiling. He’d endured the liquor and the bugs and the humiliation for nothing.
He found himself on Facebook, looking through his friends’ feeds, mostly just so he could keep his mind off of the humiliating end to his initiation. And then he noticed an ad on the side of the screen—a new ad, based on his most recent search history (which was done without private browsing, seeing as private browsing was apparently useless). The ad was for a new gay bar down the street. “Come on down for karaoke night!”
Louis’s heart skipped a beat. In the picture was a group of three people with their arms over each other’s shoulders. Two of the people were obviously gay men, and the third person was a girl with the slight bulge of an Adam’s apple: a transgender. Louis perked up. Maybe he could go down to the new gay bar and find himself a transgender date for the night. But how would he convince her to let him film them fucking? That probably wouldn’t happen.
So Louis set up his webcam on his computer, and he set it to record. He had to delete half of the files on his computer, knowing the all-night recording would probably be a massive file. He started the recording before leaving the house. He dimmed the brightness of his screen so that it appeared black, so that his date wouldn’t see herself being recorded. And then he grabbed his coat and headed for the gay bar with nothing to lose and everything to gain.
CHAPTER V
Jacob’s trip to his parents’ house did not go smoothly. First, he forgot his wallet and didn’t realize until he was thirty minutes from his house. His car was out of gas and none of the customers at the gas station would give him a pity five bucks so he could loop back and grab his wallet, so he could fill up again closer to his house. So he had to leave his car at the gas station and hop on a bus. It was almost two hours before he returned to that gas station with his wallet. The sun had already gone down.
His trip kept getting worse. He knew he didn’t have long—he still wasn’t sure how he was going to get onto his stepsister’s phone. So he pressed his foot hard onto the gas pedal and ten minutes later, he found himself pulled over on the side of the highway with flashing red and blue lights behind him. The cop took nearly fifteen minutes just to get out of the car, and another fifteen minutes to give Jacob a stern talking to. “Yeah, yeah, just give me the ticket,” Jacob said, waving his hand at the cop, motioning for the ticket.
His hurried attitude did not impress the officer. “You know we can impound your car, because you were going more than forty kilometres per hour over the speed limit, right?”
“No you can’t,” Jacob said, calling the officer out on his bluff. And then Jacob found himself standing on the side of the road as a tow truck pulled up to haul off his car. He ended up hitchhiking the last fifty kilometres to Cassidy, but it took over an hour to get a ride, and the truck that picked him up ended up making two stops: once to the use the bathroom and once to buy a chocolate bar from a gas station. Each stop took nearly twenty minutes, though Jacob had no idea why. When he finally got to his parents house in Cassidy, it was 10:00 PM.
Jacob ran up to the front door. He didn’t bother ringing the doorbell. He knew his parents always kept the doors unlocked. The lights in the house were already off. Jacob went straight towards his sister’s bedroom, but his sister wasn’t in the room. The bed was nicely made. So Jacob ran to his parents’ room. He knew he was going to give them a scare when he ran into the room, but he was running low on time and didn’t have any other choice. He threw their bedroom door open and said, “Mom, where’s Michelle? Why isn’t she in her room?”
But his parents’ bedroom was empty too. No one was home. Jacob tried calling his sister, but she didn’t pick up. So he tried calling his parents. He got through to his mother. “Where is everyone?”
“Your father and I are spending the night in the city. We were going to put on dinner, but you were all too busy, so we decided to go into the city and have a date night. Do you want to talk to your stepfather?”
“No, mom. Where’s Michelle? Is she with you?”
“Michelle is out with friends tonight. She said she wouldn’t be home until the morning. Why do you sound so out of breath? What’s going on with you?”
“I can’t explain right now, mom. Good night.” Jacob hung up the phone and looked at his watch. Now it was 10:30 PM. He only had an hour and a half to get lewd photos off of his stepsister to send to Roger and the Kappa guys.
He tried messaging Michelle on Facebook, but he had no luck. He tried
messaging a few of Michelle’s friends—the only few he knew. But none of them answered either, except for one who said, “I haven’t talked to Michelle in three years.” Jacob’s heart was pounding. He paced his parents’ house and tried to think of a plan. He found himself in Michelle’s room, hoping desperately to find something hidden in her drawers. Maybe she had an old phone with old pictures on it, or maybe she had some sexy Polaroid photos kicking around. Jacob did find an old phone, but it was dead. He spent another ten minutes tracking down the charger for it, but the charger wouldn’t bring it back to life. It had probably died by drowning in a nightclub toilet.
But Jacob did find a few particular items, which gave him a crazy idea. In her closet he found a wig—the wig Michelle wore for three months after she cut her hair short and immediately regretted it. It was long and dyed a strawberry blonde colour. He also found a drawer full of sexy lingerie: lots of lace and satin and frills and straps. There were fresh razors in the bathroom, and Jacob even found a spare pair of Michelle’s glasses—the same exact style she always wore, with big black frames.
Jacob didn’t have much time left, so he got started right away. He ran a tub full of warm water and got himself undressed. He only spent ten minutes getting his legs and crotch area shaved smooth. He felt like a complete dunce doing it, but he was desperate. He even used a fresh razor to get a close shave on his face, even though his facial hair was thin and blonde. In the bathroom he found a little jar of red nail polish—the same shade Michelle had always used to paint her nails. So he quickly did his fingers and he didn’t bother with his toes.
Then he started to squeeze his body into Michelle’s lingerie. Roger said that he wanted sexy photos—he didn’t say anything about nude photos. Michelle didn’t have much of a rack, so a couple of socks were enough to create a realistic bust. Jacob was able to use the wig to cover most of his face, but to be safe, he used a bit of Michelle’s makeup—some lip gloss, a bit of blush, and some eyeliner. He didn’t plan on getting his eyes in any of the shots, or even his lips for that matter, but he wanted to be safe.
He looked in the mirror and cracked a grin. He looked a bit like Michelle—almost like they could be biological siblings. He didn’t look like her twin by any means, but as long as he kept most of his face out of the shots, he knew he would be fine. He stared at himself for a few minutes, until he heard the living room clock chime—it was 11:30 PM.
So he migrated back to Michelle’s bedroom and he used her full-length mirror as his canvas. He posed his body and snapped dozens of shots. He only planned on using a couple, but he wanted to get as much material as possible to work with. It was 11:45 PM when he was satisfied with his selection of photos. He sent them off to Roger. His heart was pounding. After the photos were sent, he found himself staring closely at each one, trying to make sure there were no obvious signs that he was the one in the photos. The last thing he wanted was for there to be his face in some window reflection. But the photos seemed relatively safe. And they really did look like pictures of a chick posing in lingerie. Jacob smiled—at least that was one benefit of having a petite frame…
CHAPTER VI
It was 11:15 when Louis stumbled back into his dorm room with his date under his arm. He was drunk and so was she—but he wasn’t drunk enough that he would forget what he’d done in the morning.
The trans girl he picked up was convincing—at least she was convincing after a few shots, a couple glasses of champagne, and a few pints of beer. She had long hair and a thin body. From behind, Louis couldn’t tell the difference. Even from the front, she wasn’t bad when her head was tilted down to hide her large Adam’s apple. She had big eyes and dark eyelashes, which were probably fake—but Louis didn’t have time to be picky. He only had forty-five minutes to fuck her and get the footage sent off to Roger. He knew it would probably take ten or fifteen minutes just to save and export the footage once it was recorded, and another few minutes to travel across the Internet to Roger—so he really only had about twenty minutes to stuff his tranny date.
Thankfully, she was eager to start as soon as they were behind the closed door of Louis’s dorm room. She threw herself at him and started sucking on his lips. She wasn’t a gentle lover, but at least her lips were soft. She moaned softly as they kissed. She had a deeper moan than Louis would have liked. Her voice in general was deep, as if she wasn’t putting much effort into sounding feminine. She’d told Louis at the bar that she’d only been taking hormones for six weeks, and that her voice would only get more feminine as the weeks went by.
But with plenty of liquor in his system, Louis found her deeper voice to be strangely arousing. He wanted to hear it while they were making out. “Tell me how badly you want to suck my cock,” he said.
“I want to suck your cock so badly, baby,” she said.
“Say it like you mean it.”
“I want your fucking cock so badly,” she said. He smiled. He loved hearing that voice—it wasn’t overly masculine but it was obviously not feminine either.
Louis looked down and saw the bulge of her erection against her skirt. “Oops,” she said, reaching down under her skirt. “She popped loose.” She slipped her cock back into her little thong. Now the bulge was gone, but Louis knew it was still there.
His heart was pounding mercilessly. He tried to take a breath in, but his lungs were frozen stiff, so he was only able to breathe in shallow, short breaths. He looked back down at her skirt and found himself picturing her cock. He wondered if she shaved her pubic hair or if she had a bit of fuzz down there. When he looked back up, his trans date was staring him in the eyes. She had a big drunken smirk on her face. “Do you want to play with it?” she asked with that voice that made Louis so nervous and crazy at the same time.
“Really?” he said, his voice cracking.
“Go ahead,” she said.
Louis looked back down as she rose up her skirt, showing off the big bulge in her thong. There was plenty of flesh billowing out from that thin strip of fabric: the sides of her testicles and the edges of her long shaft. Louis reached down slowly, slipping his fingers over the whole package. It was warm and he could feel it throbbing. His heart skipped a beat and he let a strange sound out from his lips that was something like a whimper. He started to rub her package, rubbing harder and harder. Then he remembered that he was on a time limit. He looked over at the alarm clock at his bedside. It was 11:30 PM.
“Can I fuck you in the ass?” he said.
“Yeah darling, we’ll get there. Don’t worry.”
“No, I want to do it now. Get on my bed, on your stomach,” Louis said. His heart started pounding even harder, which he didn’t realize was possible. He stared his trans date in the eyes and watched as her smirk grew large.
“Okay,” she said. “You just can’t wait, huh?”
“No,” he said. But he was terrified. He wished he could wait and spend some extra time building up the courage he needed—though he knew that courage would probably never come. His hands were trembling and his legs were beginning to feel numb and weak. He kept looking over at the clock, wondering if he was going to have enough time. What if he couldn’t come right away?
He had an idea. While his date was getting comfortable on her stomach, he pulled out his phone. He quickly turned the volume off of his phone and then he dialled Roger via FaceTime. He flipped his camera around so it was recording out the back of his phone. He didn’t have time to save and export video files. He needed a faster solution.
Roger answered the FaceTime. Louis saw his lips moving but the volume was muted. So Louis just quickly pointed the camera at his laptop’s webcam, with its small glowing red light, and then he propped the phone up on his desk, so it was aimed at his date. Then, he went to join his date on the bed.
He undressed quickly. He was already erect. He felt terribly exposed and vulnerable, not sure how many Kappa members were huddled around Roger’s phone, watching. He climbed up onto the bed and he flipped up his mostly-femin
ine date’s skirt, exposing her round tush. Then he yanked down her little thong. He spread her perfect cheeks and he spat into her asshole, giving himself some lubricant. He didn’t have time earlier to pick any lubricant or even any condoms up from the store on his way to the gay bar. Spit would do just fine.
He started pushing his cock into his well-hung date. She was tight, but she didn’t clench. She knew how to remain relaxed while he penetrated her—this probably wasn’t her first stuffing. He sunk deeper and deeper and deeper. She started moaning louder and louder, still with that slightly deep moan.
It occurred to Louis that it wasn’t obvious that his date was a transgender, as she was laying on her stomach with her cock nestled into his bed sheets. So he gently rolled her onto her side without pulling his cock out from her ass. He tried not to look into that little lens that was watching his every move as he reached around and slipped his fingers around her cock, showing his audience that he was indeed accomplishing his task.
He looked over at the clock. It was 11:55 PM now. He’d finished his task just in time. No one said he had to climax before midnight—he just had to have sex with a trans chick, which was exactly what he was doing. So with a wave of relief washing over him, he started to pump his trans date with his long shaft. She grunted with each penetration. He could hear the big grin on her face as she began to moan. He watched closely as she reached down and started rubbing the tip of her cock as if it was her clit. “Oh yeah, baby. Make me come,” she said, her body bouncing to the rhythm of his thrusting.
Louis ran his fingers up and down his date’s smooth legs. She felt surprisingly feminine, and he found himself wondering if it was just because her hair was shaved off, or if it had something to do with the hormones she’d been taking for six weeks. Would six weeks of HRT have any noticeable effects? Was Louis just caressing a man with long hair and makeup? He tried not to think about it.
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