His life was off the rails now. He was a slave to the naughty excitement of cross-dressing and sissification. He was starting to worry that he wouldn’t be able to save himself. He was no longer setting out to prove how manly he was, so why was he still listening to the tapes? Why was he getting dressed up in his office at work? Why couldn’t he stop himself?
After lunch, he navigated over to one of the popular online communities for sissy hypno recovery. Suddenly, he could relate to all of the posters. There were many people who only made it to the fifth tape. “I listened to that fifth tape a month ago and then I stopped, but I can’t make the urges go away,” complained one poster.
“They never go away. You need to learn to live with them and to control them,” replied a senior member of the website. Kent’s gut turned. He didn’t like what he was reading. He didn’t like the thought that he would be stuck this way forever.
“You could consider going all the way,” said another poster. “If you feel the urges are this strong after just five tapes, then you could just finish out the series and surrender to your sissy side.” Surprisingly, this was the advice of many of the men on the website. “Once you swallow the whole sissy pill, at least the agony goes away for most people. As long as your friends and family can handle your new lifestyle.”
“So there’s really no hope for going back?” asked the original poster.
“Sorry, friend. The urges do get more manageable over time though.”
Kent felt sick. He felt like he’d made a gigantic mistake—and he had. He’d done irreversible damage to his brain, voluntarily, because he was obsessed with the idea of proving his manliness. But it wasn’t his fault, was it? It’s not like he actually believed the tapes were real. He thought the posters on these websites were just roleplaying, adding to the lore of the silly sissy mythology. He thought this was all just a big rouse to entertain high school kids, and now he was essentially stuck with irreversible brain damage.
And he was stuck with the agony of knowing he was now a freak, a pervert, and a sexual deviant. He was stuck with the agony, unless he did what those posters were suggesting: swallow the whole sissy pill, go further down the rabbit hole, finish the last two tapes and become like the traps in the diner. They may have been freaks as far as Kent was concerned, but they were happy freaks. They didn’t appear to be suffering any agony. They were smiling and even flirting with strangers, as if they didn’t care what anyone around them thought. And it didn’t help that people like Andrew couldn’t even tell the difference.
Though maybe there were more than just those few traps at the diner and the few at the house party. Maybe they were everywhere and Kent couldn’t tell the difference. When Kent looked at himself in the mirror, he thought he really looked like a woman, especially after the Playboy Playmate did his makeup. All he really needed was a wig and a bit of makeup practice—maybe a bit of voice work and a decent wardrobe…
Kent had another blackout moment during his last hour at work. He looked up at the clock and saw that it was already time to go home, even though it seemed like he’d just looked up at his clock a moment later and it was only 3:00 PM. Then he looked down at his computer screen and saw, in big letters: ORDER COMPLETE. A chill crept down Kent’s spine. He opened up his e-mail and saw that he didn’t just have one unread e-receipt; there were ten separate e-receipts. He’d spent over a thousand dollars on dresses and skirts and shoes and lingerie and makeup. “Shit,” he mumbled. He clicked on the first e-mail and went to the website where he could manage his order. His plan was to cancel all of them, get his money back and pretend like it never happened. And then he saw the items that he ordered.
He froze and found himself staring at the cute little dresses. There was a little black bodycon dress that would actually look so cute on him. And in another order was a pair of strappy heels that would match the dress perfectly. Maybe he didn’t need to cancel the orders. Maybe having some outfits at his house was a good thing, so it would be easier to resist the urge of stealing clothes from his friends and neighbours. It was better that he kept his newfound obsessed within the walls of his own apartment. So he didn’t cancel anything.
But if he was going to keep the clothes and makeup, then he was going to need a wig. What was the point in spending over a thousand dollars on a wardrobe and makeup if he wasn’t going to go all the way? He looked up local wig stores on his phone and found that there was one conveniently on his way home from work. So he got off the bus a few stops early and he wandered into a shop called Best Wigs.
The store was surprisingly large, with too many options to consider. Kent walked through the room slowly, noticing the price tags hanging down from some of the hair bundles: five, six, even seven hundred dollars for some of the more realistic units. And of course Kent needed to get a realistic unit if he was going to commit to this crazy endeavour.
“Can I help you?” asked a feminine voice behind Kent. He spun around with a jump. He was on edge and had been on edge for days now. “Looking for a wig?” The storeowner was a tall, pretty woman with big, stunning eyes. She had a confident smile that beamed down on Kent, making him feel small.
“Um, yeah,” he said. “It’s, uh, for my wife.”
“Is she okay?” the storeowner asked.
Kent quickly nodded his head. “Yeah. She, uh, just got a bad haircut. The hairdresser screwed up and she ended up having to shave it all off. So she, uh, needs a wig.” He forced a smile. He knew it sounded far-fetched.
The storeowner was looking down, at Kent’s hands, which were awkwardly fumbling down at his waist. He thought she was looking at his nervously fidgeting fingers, and then he realized she was looking down at his lack of a wedding ring. He quickly buried his hands into his pockets, even though he already knew it was too late. So he just forced another smile as he felt his cheeks turning red.
“Does she want to be blonde, brunette, redhead—or something funky?” asked the store owner, who was now grinning. She knew. She could see right through Kent’s awkward demeanour. She probably got lots of cross-dressers into her store. Kent squirmed at the thought of being one of them, even though he was. He hated the term ‘cross-dresser’. It sounded so ugly and so freakish. Kent had always thought that cross-dressers were just mentally ill men. And maybe that’s exactly what Kent was, now with his blackouts and his powerful urges that he couldn’t always deny. “Well?” the store clerk asked.
“Maybe blonde,” Kent said with a quiet voice.
“Long or short?”
Kent scanned the options. There was already a wig that stood out to him. He kept looking around but his gaze kept travelling back to that one wig on the wall. It was long and blonde, with dark roots. It was straight with a bit of volume, and Kent was already imagining which outfits to pair it with. “That one,” he said, pointing at the wig.
“Do you want to try it on?” the clerk asked as she took the wig down from the wall.
“Sure,” Kent said. And then he froze up as he realized he’d just outed himself as a cross-dresser. “I mean—my head is about the same size as my wife’s head.” He felt warm blood rushing into his cheeks. He didn’t know why he was still bothering with his whole married farce. He knew the clerk was onto him. But he was just too embarrassed to reveal himself fully.
The pretty storeowner stepped around Kent and got the wig situated on top of his head. She adjusted it slightly, ruffling up the hair a bit to make it look realistic. Then she turned Kent towards the mirror and said, “I think it looks pretty good, don’t you?” she said.
Kent slowly nodded his head. The wig was perfect. It looked real. He reached up slowly and ran his fingers through the soft strands of hair. “Yeah,” he said, his voice nearly a whisper.
Even without a feminine outfit or a lick of makeup, he looked like a girl. It was amazing how much that wig changed his appearance. It changed the shape of his face and it even seemed to change the figure of his body—not that his figure wasn’t feminine to begin with.
“How much?” he asked.
“It’s on sale. Four hundred and fifty,” she said. “Down from eight hundred. It’s a steal, really.”
“I’ll take it,” Kent said. And now he couldn’t wait for his new wardrobe to show up. He couldn’t wait to get dolled up. He was even starting to think about taking his feminine persona out of the house once he had all of the elements put together. Maybe he would go for a jaunt down at the dog park. Maybe he would take a ride on the bus, just to see if he could get a guy or two to look his way. Maybe he would go down to the bar and try to get a guy to buy him a drink. But what would he call himself? He was going to need a name for his new female persona…
“Are you okay?” the store clerk asked.
“Huh? Me? Yeah. I’m fine.” Kent was now standing at the checkout counter. He couldn’t remember how he got there. He must have blacked out again, but for how long? Had he said anything embarrassing? Had he done anything he was going to regret? He looked into the store clerk’s eyes and saw that she was smirking—or was it just her normal smile? He looked away quickly. “You don’t have a bathroom I could use, do you?” he asked. He didn’t need to use the bathroom, but he needed to splash some cold water on his face. Cold water was the only thing that seemed to stop the sissy urges from taking over completely. Cold water was the only thing ensuring Kent still had a little bit of sanity.
“We don’t but the store next door has—” She cut herself off. “Actually, if you don’t mind walking a couple of blocks, there’s a gas station just at the end of the road. The bathrooms are around back. If I were you, I would use the women’s bathroom. It’s much cleaner and much less busy.”
Kent stared at the woman for a moment, trying to figure out why she was suggesting a bathroom two blocks away, and why she was suggesting the women’s bathroom instead of the men’s bathroom. But he didn’t question it. He wanted to get out of that wig store and away from the woman who could see right through Kent’s anxious character. He made his way down the road to that gas station. It was a busy little gas station, with cars lined up nearly to the street.
Kent skirted around behind the station and then he spotted the bathrooms. He watched a man slip into the men’s bathroom. He looked around to make sure no one was watching before slipping into the women’s. And he was pleasantly surprised by how clean and spacious it was. He locked the door and went straight to the sink. He ran the water cold and then splashed it on his face. He took a deep breath and then he noticed a glimmer of red out of the corner of his eye.
‘Tap for a little bit of fun,’ was written on the wall with deep red lipstick. With the same lipstick, someone had drawn a long arrow pointing from those words to a hole in the wall, a hole that connected the two bathrooms. Kent’s heart skipped a beat.
Next to the sink was a little tube of red lipstick—probably the same that was used to write on the wall. Kent picked it up carefully and spun out the deep red pillar. He ran the tap again, rinsing off the tip of that red pillar. Then he brought it to his lips. His heart was pounding hard—so hard, he was worried it was going to explode inside of his chest. “What the hell are you doing?” he whispered to himself. But he couldn’t stop himself.
He reached into his briefcase and pulled out his new wig. He ripped off the tag and got it onto his head. He ruffled up the hair until it looked nice and natural on his head, then he slipped out from his dress shirt and put on the crop top he stole from his neighbour. And while he was at it, he took off his pants and put on his skirt—his stockings were still on underneath his slacks.
He did a little pose in the mirror, biting his lip in an attempt to contain his big, goofy smile. He looked cute, even without makeup. The lipstick was enough—though a bit of eyeliner and maybe some blush would have been nice too.
He heard someone enter the room next door. It was game time, time to have a little bit of fun, according to the wall. Kent walked over with his pounding heart and then he tapped on the wall. He squirmed and took a series of deep breaths, trying to calm his racing heart. He didn’t actually plan on doing anything if a cock slipped through that hole, did he? He wasn’t really going to suck off some stranger, or even touch another man’s penis. Just because he was having strange urges—it didn’t mean he was suddenly gay. Or was he suddenly gay? Were those tapes turning him gay?
A minute passed and no cock came through that hole. Maybe that hole was just a joke—surely it was just a joke. What man would be dumb enough to risk sticking his cock through a random hole in a gas station bathroom? There was nothing stopping some crazed psychopath from chopping a stray cock off—and there was nothing stopping a man from sucking off another man.
Kent tapped again, giving his heart another surge of energy. He kept his gaze glued to that hole. After a long silence, that hole became dark as if large figure had crossed behind it. Kent could hear a subtle rustling. And then a long, flaccid cock came through the opening. Kent nearly jumped back at the sight of it. It was thick and veiny and uncircumcised.
Kent’s lips parted and his heart fluttered down into his gut. Now what? He’d invited the cock through, but now he didn’t know what to do with it. There was a very vulnerable man on the other side of that wall, waiting for some action.
Kent slowly dropped down to his knees. He felt the cold bathroom floor with his bare skin, but he did like the feeling of the draft teasing up his skirt, tickling his bum and his barely covered cock.
He looked at the cock and couldn’t believe how thick it was. It must have belonged to a big guy. He reached up slowly and hovered his fingers around the man’s girth. He was terrified to touch it, but he knew he had to. He knew he would be left unsatisfied until he went through with it. So he closed his eyes and closed his hand into a fist around the soft, warm cock. His heart skipped a beat. He was doing it—he was touching a cock. And a moment later, he was gently pulling back the man’s foreskin, exposing his bulbous tip. It was only a few seconds before that cock was throbbing and growing in Kent’s grip—getting bigger and harder by the second.
And it was kind of fun, knowing that it was Kent’s sensual fingers that were making the man aroused, and soon he would be getting the man off too.
He tugged on the cock until it was hard, and then he watched as it throbbed magnificently. It was a strangely arousing sight, but only because Kent knew that erection was for him. But the man didn’t stick his cock through a dangerous hole just for a handjob. Kent needed to give the man more. So he took a deep breath, leaned forward, and opened his mouth. The cock slid onto his wet tongue. It didn’t taste like anything, which was nice because Kent was expecting the worst. In a weird way, it was even kind of satisfying, the way it slid back and forth. He could feel the veins throbbing. He could feel the whole cock bloating and twitching. And it was only a minute or two before he could feel it tensing up all over, getting ready to burst.
He slipped the cock out from his mouth and aimed it away. Then he watched as it spewed long strands of cum all over the bathroom floor. He heard the man on the other side groaning, and then the man’s lipstick-stained cock slipped back, leaving that hole empty. He got the lipstick washed off of his lips and his sissy outfit back into his briefcase, then he took off for home, hiding his face as he left the bathroom, just in case there was someone there waiting to see him. Thankfully, the coast was clear.
But that wasn’t the end of Kent’s sissy fun that afternoon. That night, he got dressed up again and he went about his normal routine. He cooked his dinner in that little skirt, and he even sat around and watched TV in his whole cute ensemble. When it was time for bed, he decided to sleep in his panties, with his headphones on his head and that sixth tape playing into his ears.
“Oh my God, look at you,” the British woman said in that recording. “I hardly recognized you. You look stunning. And how’s your voice sounding? Have you been practising? It will take a while to get it right, but don’t worry about that now. Now, we’re just going to have some fun. We still have a lot of work to do�
��but let’s not think of it as work. Let’s just think of it as fun, shall we?”
Kent dozed off quickly that night. There was something hypnotic about the British woman’s voice. It had the strangest ability to make Kent fall right to sleep. Even sleeping pills didn’t work that quickly.
CHAPTER VIII
Kent woke up with the worst dread trembling inside of his gut. He jumped out of bed and rushed over to the mirror and he stared at himself. His eyes were heavy and his skin was flushed. “What are you doing to yourself?” he said before slapping himself on the cheek. “Pull yourself out of this. You’re just one recording away.” And it was true—if Kent could stop himself from becoming a full-blown sissy in just the next twenty-four hours, then his original goal would be a success. Sure, there were some speed bumps along the way. He’d spent almost two thousand dollars on women’s clothing, makeup, shoes, and a wig. He’d sucked a cock in a gas station bathroom. He’d allowed a Playboy Playmate to fuck him in the ass with a giant strap-on—but those were just speed bumps. He could still come out the other end as a man, unlike all of those poor souls on those sissy websites, and those trannies in the diner.
He just had to get through one more tape. So he went back to that support group online community and read through some posts. He found a few made by people who only reached that sixth tape. “I’m too afraid to listen to the last one. I don’t want to lose myself,” said one poster. And surprisingly, many people replied saying they only reached that sixth tape. Apparently, on their sixth day, something happened that was too much for them. But none of them were brave enough to say what. They just kept saying “the incident”, and everyone seemed to know exactly what they were talking about. But Kent had no idea, and he was terrified of having ‘the incident’ happen while he was at work.
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