So he downloaded the next tape, put on his headphones, and he went to sleep. He laughed at the tape’s absurdity before dozing off. “Today I have something really fun planned. Don’t be afraid—you will enjoy it, no matter how scary you think it is,” said the British woman. “But first, let’s get pretty. I found the cutest crop-top at the store. It will look so good on you. I also got you a little toy. You’ll have to keep it hidden under your mattress. It’s only for when you’re feeling really naughty and there’s nobody around. I hope your walls are well insulated. Your neighbours wouldn’t call the cops if they heard you screaming, would they?”
It all seemed so outrageous. So why was he still listening to the dumb tapes?
CHAPTER VI
When Kent woke up, he could feel something wet against his smooth left thigh. He reached down to feel, and he pulled his fingers back when he felt something sticky and cold. He threw off the blankets and rolled over. There was cum all over his bed sheets—not just one puddle, but three separate puddles, as if he came three different times in the night. One of the puddles was hardened, one was cold, and one was still warm, as if he just came twenty minutes before. He looked at his computer. It was still early—the recording probably only ended twenty minutes before.
“What the fuck?” he muttered to himself. Had he jerked himself off three different times in the night? Or were they all wet dreams?
A cold chill remained in his spine throughout his whole shower. What the hell was on that tape last night? What could that British woman have said to produce so much jizz? Maybe there was something to this whole sissy hypno thing. Maybe Kent was playing a game that really shouldn’t be touched by people who don’t want to lose their minds.
He went to work and locked himself in his office again. He did his best to stay away from his e-mail client, legitimately worried he would send off an e-mail that would leave him humiliated. He didn’t even leave his office for lunch. He didn’t mind the feeling of hunger churning in his gut—it was better than the potential embarrassment he knew he might receive if he went down and waiting in one of the lines for one of the food trucks. Being around people just wasn’t an option, until he knew what the hell was going on in his head—so he took a cab home when work was done.
Andrew called three times, but Kent didn’t pick up. Finally, Andrew left a message. “I know you have to work in the morning, but there’s this big party happening tonight. Miss February is going to be there! You know? From Playboy? I was invited and I have a plus one. Don’t miss this, buddy. You have to come!”
And Kent found himself squirming. He really couldn’t miss the party, but he really didn’t want the human exposure. Even if he went to the party and Miss February asked him to go up to a bedroom, he couldn’t do anything. He couldn’t risk the same embarrassment as the night before, when Cassie stuck her fingers up his asshole. He knew the sissy impulses had only gotten worse since then… But at the same time, how could he miss a party with a real Playboy Playmate?
He paced his apartment for a while, trying to talk himself out of wanting to go. But he couldn’t help but wonder: what could go wrong? If he had a weird urge, he could just fight it away. He hadn’t had one of his blackout moments since that conversation with the redhead, and even that wasn’t so bad. He just told her he liked makeup. It’s not like he told her he liked taking giant cocks in the ass—though what if he told that to Miss February?
He got dressed, in a nice dress shirt and slacks. Before he left his apartment, he checked down his pants to make sure he was wearing boxers and not lacy panties. He just had to be sure, to make sure he didn’t have one of his blackout moments while getting dressed.
He met up with Andrew down the block from the house. Andrew was teeming with excitement, practically skipping down the road towards the party. “Must be nice not having a job,” said Kent with a laugh.
“I have a job—it’s just… part-time.”
“How many hours did you work last week?” Kent asked.
“Six. Almost seven.”
“Not a job,” Kent said. “Just don’t expect me to stick around long. I have to be up early. I just want to be able to say that I was here.” The party wasn’t nearly as loud as the last one. The music wasn’t turned up terribly loud and the guests weren’t nearly as drunk. But Kent wished the party was just as loud and drunk, because maybe then no one would notice any potential little slips or embarrassments.
He went with Andrew to the kitchen to get a drink. Then it wasn’t long before he found himself mingling with the party guests and Andrew found himself outside smoking pot with some guys who probably weren’t invited. After a few drinks, Kent rediscovered his confidence. He found that people were drawn to him: men and women. Everyone wanted to talk to him, and everyone wanted to keep talking to him. They were all interested in his work and his hobbies. He spoke slowly and carefully, making sure to control each word out from his mouth. He figured as long as he was speaking slowly, he couldn’t accidentally blurt out some nonsense about lingerie or makeup.
Miss February really was at the party. She was much shorter than she looked in the magazine, and her hair was much shorter as well—though it was possible she’d gotten a hair cut. Her laugh could be heard throughout that party house. It was a bit of an obnoxious laugh, and always with the odd snort. But Kent thought it was pretty cute, and strangely addictive. He found himself laughing whenever he heard her laughing.
And then he had one of his blackout moments. This one was longer than any he’d ever had before. At one moment, he was in the kitchen getting a better. The next moment, he was out on the deck, chatting with Miss February. The drink in his hand was nearly empty, as if he’d been blacked out for nearly ten minutes. He felt the colour drain from his face. Miss February was laughing, covering her mouth so she wouldn’t spit up her drink. “My God, you’re funny,” she said. It didn’t help that she had a British accent, which didn’t sound too much different than the voice on that sissy hypno tape.
Kent had no idea what he’d said to her. But she was smiling and laughing and blushing, so maybe he said nothing harmful. Maybe everything was fine. “I hope you don’t mind me saying, but you’re really very beautiful,” Kent said.
She laughed again. “I know,” she said. “You just told me that.”
“Oh did I?” Kent said, blushing. “Well, it must be true then.”
She was grinning and gently biting her bottom lip. Kent knew what that meant. He knew she wanted a piece of him. He had no idea how buttered up she was, but he figured he should go for it regardless. He would regret not making a move on Miss February. So he leaned in and kissed her, and she actually kissed back. Her hands slipped around him and her fingernails gently dug into his skin. It felt good. She even slipped a bit of tongue into his mouth. She smelled magnificent, like flowers and fresh baking.
“There’s a room upstairs,” she said. Kent’s heart was pounding. He was about to go upstairs with Miss February, quite possibly one of the sexiest women on the planet. He took her by the hand and led her through the house. He felt all of the jealous gazes of party guests as they ran up the stairs, giggling with excitement. Once they were in the room, he made sure the door was locked before turning back to her for another kiss. “Are you really sure you want to do this?” she asked.
“Am I sure? I’ve never been more sure of anything in my life,” he said with a laugh. What sane man would turn down sex with a Playboy Playmate?
She pushed against his chest, pushing him down on the bed, and then she bent over and started undoing his belt. “You’re so naughty. I love it,” she said.
And Kent laughed. “Am I?” he said. She looked at him with wide eyes and nodded her head. “Alright,” he said.
She tugged down his pants and boxers. In the meantime, he took off his shirt, making himself fully naked. And then he remembered that he was clean shaved. He felt his cheeks turning dark red. Before he could say anything, Miss February said, “Wow, you really weren’t ki
dding.”
And he was slow to reply. “I wasn’t?” he said awkwardly.
She laughed as she stood up. She gently slipped the straps of her dress over her shoulders and let the whole garment fall to the floor, exposing her one-piece of lacy lingerie. Kent was fairly sure it was the same piece she wore in the magazine. His heart fluttered. He was expecting her to crawl on top of him in the sexy lingerie, but instead she took that off as well, exposing her perfect, perky tits and plump, hairless pussy. A whimper slipped out from his lips. He bit down on his tongue and prayed that he wouldn’t say anything that would ruin everything.
She tossed the one-piece at Kent. “Go ahead,” she said with a big smirk. She had the most beautiful naked body he’d ever seen.
“Go ahead, what?” he said.
“Put it on,” she said.
And then his heart skipped a beat. “What?”
“You said you wanted to wear my lingerie. There it is—try it on. I think it’ll look cute on you.”
His heart skipped a beat again, and then something worse started happening: his cock started to grown and harder. He couldn’t help it. The thought of putting on the lingerie made his heart rate spike. His whole body tingled. He tried to say something back, but he couldn’t muster up any words. He looked down at the lacy one-piece. It was so soft and sexy. He wanted it on his body so badly. And Miss February seemed to want it as well, so he couldn’t say no, could he? He sat up and started to slip the outfit onto his body. He liked the way it felt—no, he loved it. He bit down hard on his tongue in an attempt to suppress his big smile.
“You really do look cute. Hold on.” She spun around and then she started riffling through dresser drawers. “Ah ha! Here.” She came towards him with a little bag of makeup. “You just need a bit of eyeliner—maybe some mascara and a bit of blush.” She sat down next to him and told him to close his eyes. He didn’t resist. He couldn’t resist or even move. He was frozen with terror. He was apparently no longer in control of his impulses. His mind had gone astray. And his memory was starting to go with it.
He sat there and allowed Miss February to do his makeup for the next ten minutes. Then she stood up and looked down at him and said, “You’re so adorable!”
Kent looked over and saw himself in the mirror. She wasn’t wrong, though that only made him feel worse. That dread in his gut was overwhelming now, churning and gargling. He stood up slowly and turned to his side. He really looked like a chick. All he needed was a wig, and the illusion would have been complete.
Miss February took off her choker necklace and slung it around Kent’s throat. “This should help. There! That’s amazing.” She stepped back again and her face lit up. She was proud of her creation—or was it Kent’s creation?
“Now where’s this girls’ dildo?” she said, starting to dart around the room. “Every girl has a dildo.”
She ended up on her hands and knees, pulling out a large box from under the bed. And sure enough, that box was filled with sex toys: gags, dildos, bondage, whips, and a large object that appeared to be a folded up sex chair. Miss February dug through the box and then she pulled out a large strap-on dildo. The sight of it made Kent’s heart plunge into his stomach. “Just what you wanted!” she said. And had Kent told her that he wanted to be fucked by a strap-on? Did he say it during his ten-minute blackout, down on the deck?
He stuttered and then said, “I said that?”
She laughed. “Get on your stomach. This is going to be fun. And make sure you’re facing the mirror—it’s only fun if you can see yourself.”
And for some reason, Kent followed the command. He got on the bed, stomach down, facing the mirror. He looked into his own eyes, which he hardly recognized, and then he watched as the beautiful Miss February climbed up on top of him, with that strap-on strapped tightly to her body. It was black and probably ten inches long, making a nausea swirl deep inside of Kent’s body. “It might hurt a bit at first,” she said as she squirted plenty of lubricant onto the large cock. “This is going to be so much fun.” And still, Kent couldn’t get over how much she sounded like the girl in those recordings. Maybe that explained why he blacked out for so long.
He felt the tip of the cock press up between his cheeks, and then he felt her pushing down. She held his butt cheeks open with both hands, and it was only a moment later when she penetrated. He nearly screamed, but he didn’t want any attention turned towards that room. So he bit down on a pillow. She sunk deeper and deeper. He could feel the hard plastic ridges of the dildo’s fake veins. He could feel his asshole stretching, but it felt so good. He hated how it felt so good.
He started to moan and clench the bed sheets. He took a series of deep breaths. “It’s so tight,” she said behind him. “You’re such a filthy little slut, aren’t you?”
“Yes,” Kent replied. And strangely, the yes came out in a girly voice.
The cock pressed all the way up inside of him, nearly touching his sternum. And then she started to thrust back and forth. He couldn’t stop himself from moaning. He couldn’t believe how good it felt. He didn’t want it to end. He wanted more of her—he wanted that whole ten inches inside of him, plus more. “Call me a slut again,” he said.
“You’re a filthy fucking slut,” she said. “You just can’t get enough, can you, you little slut? You love it when I pound your little pussy, don’t you? You’re a slut and you like it.”
Kent’s head was spinning now. He was so aroused, trembling all over with euphoria. It was only ten seconds later when his cock started to unload on those bed sheets. “Fuck!” he screamed. Miss February giggled with her cute giggle, and then she even snorted a little bit. She slapped his ass, which he also loved, and then he begged her to keep calling him a slut. He had no idea why he liked it so much, but every time she said it his heart skipped a beat and a euphoria filled his body. He loved being fucked in the ass and slapped and called filthy names.
She reached around to feel his cock, and then she gasped. “Oh my God, you came?” she said.
“Yes,” he said with his cheeks turning red.
“Naughty girl. I want you to lick all of it up.” She pulled her thick cock out from his asshole and then he followed her command, crawling down to that big warm puddle. He licked it all up and swallowed it with a big grin on his face. Then she stuck her cock back into his tight hole while he was on his hands and knees and she continued to thrust. And two minutes later, his cock was unloading again with another large puddle of cum. She saw it happen this time, and she couldn’t stop herself from laughing. “Oh my God—you’re doing it again!” she said. “And you didn’t even touch your little cock!”
She reached down under his pelvis, scooped up the warm cum, and then she wiped it all over his hairless body, making him tremble with a warm euphoria. Why did he like this so much? Why was he so obsessed with this horrible level of humiliation? She pulled out and then he fell onto the bed, out of energy. She laughed and then she pulled her dress back onto her body. “I need to be going, but I had fun with you, you little slut.”
Kent didn’t have the energy to reply. She was gone for five minutes before he had the energy to even sit up.
And even though he was terribly humiliated and filled with dread, he still put on that fifth tape as soon as he was home and in his bed. Now, he couldn’t wait to see what would happen next. He couldn’t wait to feel the amazing euphoria that would come with another sissy hypno tape.
CHAPTER VII
Kent woke up with his heart pounding. He sprung up and threw off his blankets, and was surprised to see that there were no cum stains. But he did see that his body hair was starting to grow back as an even layer of stubble, so he made sure to shave up while he was in the shower. As he pulled his razor around his cock and pelvis, his cock suddenly started to become rock hard. He loved the way he looked with smooth, hairless skin. He put down the razor and held his feet close together, standing up straight and cute. His cock remained hard, but he wanted to see what it wou
ld look like out of the picture, so he awkwardly stuffed it between his thighs, along with his ball sack. It hurt a bit, being bent down while so hard, but it was worth the sight.
He reached around back, where the tip of his cock was just beneath his butthole, and then he started to rub: both his tip and his hole. It was only a minute before he was squirming, and another minute before he came backwards for the first time in his life. He didn’t even know such a thing was possible. He was shocked when he turned around and saw how much cum was dribbling down his shower wall. He was about to spray it off the wall when he got the naughty idea of licking it up. His heart began to race and then he sunk down to his knees, pressed his palms against the tile wall, and he took a big, long lick of his own product.
And then he realized he was running late for work, so he got dressed quickly, putting on his red panties instead of his usual boxer shorts. Before running out the door, he made sure to stuff his skimpy stolen outfit into his briefcase. He didn’t know what he planned on doing with it, and he knew bringing it out of the house with him could have only been a terrible idea, but he couldn’t resist the exciting urge. He held that briefcase close to him on the bus. His heart wouldn’t stop pounding. It was a miracle the men and women around him couldn’t hear that heart as it tried to slam through his ribcage.
Once again, he made sure his office door was closed and locked and his blinds were shut. Then, he slipped out from his pants and into his skirt and stockings. He didn’t get much work done, constantly staring down at her perfect legs, and then freezing up every time someone walked past his office door. His co-workers knew he was in there, and it was just a matter of time before one of them needed something. He was playing a dangerous game and he knew it all too well. It was around lunchtime when he had the sense to change back into his normal work attire (still with those panties under his slacks). He found himself in the mirror, splashing cold water on his face, trying to convince himself to pull his life back together.
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