So he called in sick, taking one of his few sick days. He made a large pot of coffee and spent the morning at his kitchen table, drinking cup after cup. He had nothing else to do. There was lots he wanted to do outside, but he was set on remaining inside for the day. Under no circumstances would he leave his apartment.
At least that’s what he thought, until noon rolled around and there was a knock at his door. He carefully crept up to the peephole and looked out. His female neighbour was standing there. Kent wasn’t going to answer it, but she knocked again, and then again. What if she knew he stole her clothes? What if her next stop was at my building manager’s door, to get the key to get into Kent’s apartment and take back what was hers?
So Kent opened the door. “Hey,” he said, forcing a big smile. He was ready to dive back into his apartment if one of his weird urges came upon him. He held the door firmly.
“My pipes are all weird again and my husband still isn’t back. The building manager isn’t answering his door, and I heard your TV playing so I knew you were home. You don’t think you could come and help me, do you?” She looked desperate. Her eyes were glowing and her smile was irresistible.
“Just let me grab my tools,” Kent said. He was hardly breaking his own rule. He still wasn’t leaving his apartment building, and he wasn’t even leaving his own floor. He could be done and back in his apartment in a matter of minutes, before any impulses took over.
He sauntered into her place and headed straight for that sink. “Same problem?” he asked.
And then he heard his neighbour’s voice from the other room. “Same problem,” she said.
Kent got down and popped open the access panel. He looked in and saw that the same pipe was loose. Though it seemed impossible. A pipe can’t just pop loose so easily. Kent had screwed that pipe in firmly, and no amount of water pressure can unscrew a pipe in a matter of days. So Kent reached in with his wrench and he made it as tight as possible. He tested the sink and everything worked just fine, but he had a feeling that he wasn’t really there to fix her pipe.
He looked over when he heard her stepping up behind him, and he saw that she’d quickly gotten changed into a skimpy lingerie bodysuit. It was lace and clear. He could see her perky nipples trying to poke free from the tight garment. He opened his mouth to say something, but he didn’t know what to say. “Well?” she said.
“W—Well what?” Kent managed to stutter.
“Are you going to fuck me or not?” Her face was red and her eyes were shimmering, as if she was trying not to cry. Kent wasn’t sure what was happening. Why did she want to fuck him so badly? Was she just bored?
“I shouldn’t,” he said. “I should be getting back to my apartment.”
“Please fuck me,” she said. “My husband is always home but he won’t fuck me. He’s going to be back in a few hours and I don’t know when he’s leaving again. I need to be fucked. Please just fuck my little pussy. I’m begging you.” She came up to Kent and put her hands on her sides. She was squirming—literally unable to contain herself. She reached down and cupped Kent’s cock. She squeezed and massaged gently. “I’ll do anything,” she said.
Kent was about to reject her, even though she was beautiful and wet—and then he suddenly say her as his solution. He was attracted to her. He wanted to fuck her. And maybe a good fucking was all he needed in order to get his head straight, to remember that he was really a man and not some sissy. So he put his hands on her sides and he spun her around. He put a hand on her back and bent her over her own kitchen counter. She let a moan slip out from her lips. She was already halfway to having an orgasm, just from being touched by a man. Poor girl probably wasn’t lying—her plumber husband probably never fucked her.
Kent reached down and pulled away the thin strip of lace covering her pussy, revealing her plump, wet lips. The sight made Kent’s heart stutter—and he loved that stutter. He was still a man. He still loved women. Those tapes hadn’t corrupted his mind completely—not yet. He ran his fingers over those damp lips and then he tugged down his pants, letting his semi-erect cock fling out. He grabbed it and pressed it against her warm pussy. She let another moan slip out as she began to push her bum back, grinding herself along his hardening shaft.
Kent had the biggest smile on his face. There was still hope. He could still be the man he knew that he was. Though as he looked down at his pretty neighbour, he couldn’t help but wonder how that lingerie would look on him—and those heels; he’s still never worn a pair of heels before. He couldn’t wait for his shipment to come in the mail, so he could see how perfect his own legs would look with a cute pair of—
“Well? Are you going to fuck me or not?” she asked, still squirming, still desperate for his cock.
He was hard now, though not entirely because of her—but that didn’t matter. He was still going to fuck her and he was still going to come inside of her and he was still going to prove to himself that he was still a sane, straight man. He mashed his tip between her plump lips and then he pushed inside of her. She gasped and clenched and trembled and moaned. He squeezed her butt cheeks with both hands and spread them wide so he could watch his cock travelling deeper and deeper into her body.
He suddenly had the urge to ask her to reach around and stick her fingers into his asshole, but he resisted the urge. He bit down hard on his tongue and started thrusting. He had the urge to ask if he could put on her bodysuit, or maybe she would be interested in fucking him with the handle of his screwdriver—he resisted those urges as well, pumping her harder and faster. He just needed to come—he needed to get the fucking over with before one of these urges manifested into reality.
So he closed his eyes and focussed as hard as he could. He loved the way her wet pussy felt, clenching along his hard shaft. He loved the way fluid was dribbling down her thighs. He loved the sounds of her moaning, and he even loved the sounds of air escaping her pussy when he pulled his cock mostly out before plunging back down. And more than anything, he loved that he loved all of those things. He was still a man.
He dug his fingernails into her skin and then he thrusted himself forward with a heavy grunt. His cum filled up her tight snatch and she screamed out as she reached her long-awaited orgasm. More fluid gushed out of her and then Kent stumbled back to watch his creampie ooze out from her cunt. “I should be going,” he said before she was even able to pull herself off of the counter. She looked back at him with glowing eyes. “Whenever my husband is gone, can I count on you to come over?” she asked.
Kent shrugged his shoulders. “Why doesn’t your husband want to fuck you?” he asked.
“Because he always just wants me to fuck him. He makes me put on this stupid strap-on, and when I ask him to fuck me, he can’t get it up. So sometimes I ask him to put on the strap-on, but it’s just not the same. He even likes to wear my lingerie. I mean—he looks good in it, but I still have needs, you know?”
Kent forced a smile. His heart stuttered. And then he turned to leave. Maybe there were sissies everywhere. Maybe there was a couple of them on every floor of Kent’s apartment building. Maybe every second guy on the street was a secret sissy. Maybe it wasn’t such a terrible thing. Maybe Kent didn’t need to feel so ashamed, as if he was some freak of nature. At least he wasn’t like his neighbour’s husband. At least he could still find satisfaction in satisfying a woman.
He stayed locked up in his flat for the rest of the day. He ended up taking a sleeping pill around 8:00 PM, not that he needed it. Once he hit play on that final recording, he fell right asleep. He didn’t register the British woman’s first few words.
CHAPTER IX
Kent woke up to the loud screeching of his apartment’s buzzer. It took him a moment to realize he was no longer asleep and no longer dreaming. He pulled himself up as the buzzer rang again. He stumbled over to the unit on his wall and pressed the button. “What is it?” he said with a groggy voice. And then he noticed the clock on the wall that read 2:45 PM. He’d been asleep for almos
t eighteen hours—how did a single over-the-counter sleeping pill do that?
“I’ve got a few packages here for you—I need a signature,” said the man who was standing downstairs at the front door. “Mind hurrying up?”
“I’ll be right down,” Kent said. He went down in his pyjamas, rubbing the sleep out from his eyes as the slow elevator made its way down to the lobby. He was still in a daze, still unsure of how he managed to sleep for so long. Was it because of the sleeping pill? Or was it because of the tape.
He’d forgotten about the tape—the final sissy hypno tape. He was finished with the experiment. He was done the ultimate manliness test, and he’d passed. At least he was pretty sure he’d passed. He wasn’t currently fantasizing about sleeping with men or wishing he was wearing women’s clothing. The thought of a beautiful naked woman still got his heart racing.
He answered the front door of his apartment building with a big smile on his face. “Hey—you’ve got some packages for me?” he said. He had no idea what the packages were—he figured they had something to do with work. When he thought of work now, his gut turned. He was supposed to be at work. In fact, he was only an hour away from the end of his workday. Hopefully his boss just assumed he was still sick.
“Sign this,” the deliveryman said, thrusting a clipboard forward. Kent signed the paperwork and then he saw the large stack of boxes sitting next to the door. “Enjoy,” the deliveryman said as he turned and walked away. It took three trips back and forth to the elevator to get it loaded, and then it took three trips from the elevator to his apartment to get everything inside. He grabbed a box cutter from his toolbox and opened the first box.
Inside that first box was the black dress that he ordered, as well as a few other dresses and a skirt and a couple of tops. In another box was four pairs of cute high heels. In another box he found more dresses, and then in another box he found leggings and panties and lingerie. The smaller (and heavier) of the boxes was filled with makeup supplies. His eyes lit up as he looked down at the haul and an excitement filled his body. It would take a whole week just to try everything on, and he couldn’t wait to get started.
He grabbed that black dress and held it up to his body. Then he grabbed that box of makeup supplies and started towards the bathroom, to get started. But he only made it a few steps before he paused, his heart suddenly trembling. He looked down at the dress, which he knew was going to look so cute on him. “Just stop,” he said to himself. It wasn’t too late to return it—everything was still packaged, still with tags. He could get his money back, and more importantly, he could keep the last bit of his sanity.
If he went into that bathroom, then the sissy tapes won. If he got himself all dolled up and beautiful, then he didn’t survive the seven tapes. He would have become exactly what he was trying not to become: an emasculated sissy.
But he didn’t want to return the clothes. He wanted to wear them. He wanted to go out to the cafes and parks and bars in the little outfits. He wanted to feel the gazes of gawking men, and for once in his life, he wanted to know what it felt like to be ‘sexy’. Was it so wrong?
He still wanted to be a man. He wasn’t like those traps in the diner—he didn’t want to become a woman and stay a woman and be nothing but a woman. He knew that he was biologically male. He knew that there were people in the world who wouldn’t accept him in a skirt and a pair of black strappy heels. And he knew there would be plenty of times where he just wanted to be a man: at work, visiting family, at football parties, and so on.
He looked at the dress again, now with a head filled with confusion. He knew he couldn’t be both a man and a woman. He knew he couldn’t even technically be a woman, as far as biology was concerned. But maybe he could be a trap from time to time. Was that so outrageous? It would essentially be a hobby. He didn’t have to tell people about it—or maybe he would tell people about it. Who cares what other people think? He had friends who played Dungeons & Dragons—lots of people made fun of them, but was it wrong to play the game? Of course not. Different people like different things, and different people are raised to accept different things.
A smile crossed Kent’s face as he realized something: he was still a man. For quite possibly the first time in his life, he was confident in who he was. If some blonde Swedish woman accidentally called him a woman on the streets, it wouldn’t phase him. In fact, now he might think of it as a sort of compliment.
So he was successful with his experiment. He did prove to himself that he was a man, and he was more sure of that now than ever before: he was a man who was no longer afraid of being seen as a sissy or some closeted transgender. He was just human, like everyone else.
He went into that bathroom and put on that makeup and he tried on that dress. He looked stunning, especially once that blonde wig was on his head. He put on a pair of heels and then he stood in front of his mirror for a while, admiring his awesome figure and his beautiful face. He knew he was convincing and he knew he was going to turn heads. He couldn’t wait to get out onto the streets, to start experiencing life as a pretty trap.
But first, he was curious: what was on that last tape? What were the final words of that British woman? He went to his computer and pressed play on that final minute of recording. “Look at you now,” she said with her thick British accent. “Look at how beautiful you are. Look at how confident you are. You were born to wear that dress. Your legs were made for those heels. You’re perfect. You’re going to turn so many heads. And look how happy you are. Look at that smile! That smile is worth everything, don’t you think?”
And Kent really was smiling. He couldn’t help it—he really was happy. He couldn’t wait to step out that door and start his new life: the improved version of his old life.
THE END
STIFF COMPETITION
Ray and his roommates have a long running competition that restarts every week. The loser of the game has to buy the winner beer and do his chores. And the game is simple: you get one point for going on a date, another point for getting a kiss, another point for getting head, another point for going all the way, and maybe even a bonus point for unlocking the back door. But to get the points, the players have to show proof, usually in the form of a picture.
Ray is unfortunately used to losing. He’s lost count of how many cases of beer he’s bought for his roommates. But one week he suddenly has a stroke of luck when he lands a date with a beautiful blonde. She’s cute and funny and she’s even willing to go back to Ray’s house for a bit of fun. But she has a confession to make before they get started in Ray’s bedroom, and now Ray has to decide how badly he wants those points.
CHAPTER I
Losing didn’t easier for Ray, and still, he continued to lose week after week after week.
He was getting tired of walking into that liquor store across the street from his own house, buying four cases of beer that he wouldn’t even get to drink, and then walking back to his snickering roommates. “I’m sure you’ll win next time, Ray,” Mason would always say with a big, crooked grin on his face.
It wasn’t fair: Mason, Paul, and Aaron were all genetically gifted guys. They were athletes, spending whole days at the gym. They had rich parents, so they didn’t have to work much to get by. Ray wasn’t quite so lucky. Ray had to work his crappy job every day, just so he could keep up with the bills. He never played sports because his parents were always afraid he would get hurt. He always believed them, but now he resented them: he had a small, scrawny body that was incapable of packing on muscle, and he flinched every time a ball flew in his direction.
Ray didn’t want to participate in the weekly game of ‘Fuckeries’. He should have never agreed to it in the first place, knowing that it was a game invented by Mason: a guy who loved to brag and win and mock losers. The rules to Fuckeries were simple: one point for scoring a date with a girl (she had to be at least a six out of ten), another point for a kiss (you had to prove it happened), another point for a blowjob (again, it had to be prov
ed), and another point for sex (of course, it had to be confirmed). And of course, there were other ways to collect bonus points: anal was worth an extra point, and a video of the girl swallowing was worth another—but very, very hard to get (yet somehow, Mason got swallowing videos all the time).
Ray participated in Fuckeries with all of his roommates: Mason, Paul, and Aaron. The winner didn’t have to do chores for the week. The loser had to buy everyone a case of beer. Ray didn’t necessarily want to win—he just didn’t want to lose for another week in a row.
He tried Mason’s strategy, but it just didn’t work for him. Mason would go to every party on campus and he would single out the drunkest hot chick and then he would try to get her even drunker. He didn’t always get laid, but he usually got laid. Even Ray’s other roommates had accepted that Mason would probably always be the winner. It didn’t help that he looked an awful lot like a young George Clooney, and he was on the university’s football team—a team that was actually good and actually won lots of games. He was always bringing cheerleaders home, and then he would tape himself fucking them up in his bedroom.
Ray would show up at the parties, spot a drunk chick, and then he would freeze up, too afraid to approach her. He was terrified of being rejected, even though he knew the girl wouldn’t remember a thing. He was scared the girl would look down at his scrawny figure and laugh, and then everyone else would turn around and start to laugh. So at every party, Ray would end up standing in the corner with a drink clasped in both of his hands. He was invisible, and maybe that was for the best.
Paul was also on the football team. He looked more like a young Paul Rudd—not exactly every girl’s dream, but he made it work for himself. He never scored any touchdowns and he hardly got any time on the field, but apparently girls just want to be with guys on the team. Ray tried out for the team one summer, thinking he could possibly be the guy who kicked the ball across the field, or maybe even one of the guys who catches the ball and runs. He didn’t know a lot about football, but he figured it couldn’t be so hard. On his first day at the try-out, he was checked and knocked unconscious for nearly twenty seconds. The coach told him to go home. “And for your own good, don’t come back,” he said. Maybe Ray’s mom was right.
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