“It’s a nice room,” she said with a forced smile.
And then I found myself staring at her, into her eyes, trying to think of something else to say. I was still trying to come up with that excuse, but at this point it was obvious that I didn’t have an excuse. “So you’re a working girl,” I said, and then I regretted saying it. It didn’t matter what I said—I would have regretted saying anything. I was regretting everything already. I hated that I was still standing in that room.
“I guess so,” she said, looking down at her heeled feet. And that’s when I realized she was wearing the same outfit we shot in: the poofy lace dress with the sheer chest and arms, the black choker, and the lacy cat ears. She was even wearing the same costume jewellery, and that same intoxicating perfume. I got a good whiff of it as she skirted by me again on her way to the mini bar. She pulled out a small bottle of whiskey and took a big swig, straight from the bottle. I didn’t blame her—I could have used a swig of it—though I wished she would have taken a swig of something a bit more feminine than whiskey. I didn’t need the reminder that I was in a room with a biologically male prostitute. “Should we just get right to it then?” she asked.
And I wasn’t sure how to respond. I still wasn’t sure I even wanted to fuck her. I mean—I did want to fuck her, but not under the circumstances. I certainly didn’t want to sleep with a girl who didn’t want to sleep with me. But at this point, what other choice did I have? I’d come this far. I’d made her keep her entire night clear. She probably needed the money… Maybe I could just give her the money and leave, and then pretend like this night never happened. It wasn’t a ton of money—nothing I would miss too seriously.
But if I left, then that lingering curiosity would never go away. I had to go through with it. I had to sleep with Jenn—or Trisha, or whatever her name was.
I walked over to the bed. I took a deep breath as I pulled my shirt over my head, leaving my chest exposed. Jenn walked up behind me and reached around my body. She pressed the palms of her hands against my chest and began to rub. “What are you doing?” I asked, suddenly tense.
“Massage is part of the package,” she said. So I let her go on. I didn’t want to throw a wrench into her routine. I looked down and watched as her hands moved in sensual circles, slowly up and down my torso. It felt kind of nice until I started to stare closer at those hands and think about the fact they really belonged to a man. I closed my eyes and tried to picture her face. But the only image that came to my mind was her cock.
But that’s exactly why I was there, was it not? If she were just a regular biological woman, I wouldn’t have been in that hotel room. I wouldn’t endure this much anxiety for some boring male-female sex. Or maybe I would still have gone through with it—maybe I was there for Jenn and not for what Jenn had between her legs.
Her massaging hands managed to get my belt undone without me noticing. She was skilled with her hands, well worth the money. Her fingertips were starting to tease their way down the front of my pants, underneath the elastic waistband of my boxer shorts. I closed my eyes again. I could feel those fingers worming down across my pubic bone, towards my shaft. “Are you sure you want to do this?” I asked before opening my eyes.
She paused. “Do you not?” she asked. The tension in the room was terrible. I could already tell that this was going to be something I regretted. I was literally paying money to have a regret that would probably stick with me for the rest of my life. “It’s your money,” she added.
“I want to,” I said, and I felt like I had more to say, but the words didn’t come. So she resumed her routine, pressing her hands down further. I felt her fingertips slipping onto the shaft of my cock. My heart stuttered and I took a sharp breath in.
She took a step closer, pressing her body against mine. “Oh, I forgot,” she said, suddenly stepping away from me, taking her warm body and hands with her. I looked back at her and watched as she tapped something on her phone. I suddenly had a terrible thought in my head: what if Jenn was a cop? What if this was all a big sting operation? What if she was now alerting her squad, telling them to move in? I felt dizzy and faint.
And then some soft music came on. She’d used her phone to turn on a Bluetooth speaker. She placed the phone down and walked back over to me, putting her hands right back to where they were: one on my chest, one pressed down the front of my boxers. And now she was swaying to the music, rubbing her body against mine. I could feel the tickle of her black lace, and I could feel the slight bulge of her chest—or maybe I just imagined that bulge. Maybe I just wanted there to be a bulge, so I wouldn’t feel like I was fooling around with a man. She wasn’t a man—she was a beautiful woman. She just happened to have a cock.
The image of that cock was suddenly back in my head—and I could feel the bulge between her legs rubbing against my bum, through her skirt. That bulge was real. I knew I wasn’t imagining it.
CHAPTER VI
She had her fingers wrapped around my cock now. She was massaging expertly. It felt good, but everything about it still felt wrong. I didn’t care that she was a trap—but I hated that she was being paid. Would she fool around with me if I didn’t give her money? Probably not. I was just a sleazy John, just another pervert she had to put up with so that she could make a living. She was probably hoping I would come quickly so that she could get on with her night—get in the shower and forget I ever existed. Hell, she probably wished I would drop dead so she wouldn’t have to go through with the paid romp.
At least that’s what I thought, and then I felt something move: her cock. It suddenly felt harder, and I was pretty sure I could feel it throbbing, even through her panties and skirt and my pants and boxer shorts. She was getting hard—faster than me. Was she more aroused than me? Or had she taken a pill before I arrived? Maybe she had to take pills in order to get it up with perverts like me—or maybe she was really attracted to me…
I looked back at her, over my shoulder. Her cheeks were red. Her eyes were heavy and lethargic. She was gently biting her bottom lip. I was no body language expert, but it certainly looked like she was aroused. Or maybe she was just a very good actor. Surely acting is a skill that every successful prostitute needs to have, right?
But surely no actor can get a stiffy without actually feeling aroused—how could that be fake? Unless she took a pill—but the timing was just too perfect. It couldn’t have been an erection from a pill.
Suddenly, my cock was rock hard, throbbing in her tight grip. She wasn’t just massaging anymore. Now she was tugging and stroking. Her fingernails were gently digging into the skin of my chest. And she was rock hard against my bum. I carefully reached back and pulled up the skirt of her dress, so there was less between her and me. I wiggled down my pants and boxers, so her warm rob was bare against my skin. I liked the way it felt. I liked the way it made my heart race. And I was pretty sure I could feel her heart racing against my back as she continued to sway to the music.
“You’re my first,” she said without prompt.
“What?” I said.
“You’re my first client.” She continued to sway, still tugging my cock up and down.
“How is that possible?” I asked. I didn’t believe her. Surely she was just lying to me. She probably told all of her first time clients the same thing, to make them feel more comfortable and excited.
“No one’s messaged me. You were the first.”
“That’s hard to believe. You were by far the most convincing girl on that site.” I realized how creepy that sounded once I said it. Now she probably thought that I was a frequent user of prostitute websites—not that it made any difference.
“Maybe that’s the problem,” she said with her cute little laugh. “Maybe no one actually believed that I’m trans.”
She tightened her grip on my cock and I felt her cock twitch. She let a little moan slip out from her lips. I became tense, suddenly overwhelmed by the same euphoria that had hit her. “You’re big,” she said.
“Thanks,” I said. I nearly said ‘I get that a lot’, but I managed to stop myself.
But I couldn’t stop my next urge: to reach around and feel her erection. I still hadn’t looked at it. I still wasn’t entirely convinced that it was real. But once my fingers were around that warm, throbbing shaft, all of that uncertainty vanished. The cock in my hand was real, and it was really hard. I looked back and down. She was all shaved, so her cock looked big, even though it wasn’t even as big as mine. Her tip was a shade of pink and there was a wet glimmer dribbling out from the tip.
“Do you want to suck it?” she asked with a timid voice.
I didn’t answer. I was too afraid to answer. I just spun around and slowly dropped down to my knees. I’d never sucked a cock before. I’d never even touched one that wasn’t my own. But I wanted to do it. I had to do it. I grabbed it, aimed it down, and I opened my lips. First, I stuck out my tongue for a little taste. I ran the tip of my tongue across the tip of her cock, tasting that little wet dribble. It was salty, but not off-putting. She moaned slightly.
I watched it throb for a moment, and then I leaned forward, allowing it into my mouth. I closed my eyes as it slid down the length of my tongue, towards the back of my throat. I closed my lips firmly around her girth and I began to suck, bobbing my head slowly. It wasn’t gross like I was half-expecting. It was actually strangely satisfying, the way it sat perfectly on the flat of my tongue. I liked the feeling of her veins pulsating against my tongue and the insides of my cheeks. I especially loved the feeling of her fingers nestling into my hair as she began to gently thrust herself back and forth, using my head like a glorified sex toy.
I stopped bobbing and let her take over. She had her eyes closed and her head tilted back. Her lips were parted and moaning. I couldn’t believe how hard she was. Her foreskin was stretched far back—as far as it could possibly go. I used one of my hands to cradle her ball sack. I gently pulled on it, stretching it downwards. I loved the way her testicles swelled and contracted warmly in the palm of my hand.
She started thrusting harder and harder, gripping my hair tighter. Her tip was pushing into the back of my throat, but I managed not to gag—though drool was beginning to dribble out the corner of my lips, down my cheeks. My own cock was pressed firmly against my abdomen, throbbing intensely. I’d never been more aroused in my life. I loved sucking her cock. I loved massaging her ball sack. She didn’t even stop me when I reached around and began to push a finger into her butthole.
She pulled out suddenly. She was breathing heavily and quickly. A strand of saliva connected her tip to my lips. “Everything okay?” I asked with a pounding heart.
“I nearly came in your mouth,” she said.
“I wouldn’t mind,” I said.
“I don’t want to be done yet,” she said with dark red cheeks.
“Fuck me in the ass,” I said. And then I felt the colour drain from my face. Did I just say that? Did those words just escape my lips?
“Are you sure?” she asked.
I opened my mouth to reply, but no words came out. I was shocked into silence. Some sort of foreign presence had entered my body and was now in control. Instead of replying, I climbed up onto the bed and I laid myself flat on my stomach. It was only a few seconds later when she climbed up on top of me, her lacy skirt teasing across my skin as she got herself positioned. I felt her warm cock slap down between my butt cheeks. Her knees were planted firmly at my hips and her bum was pressed down on my thighs.
“Have you ever done this before?” she asked.
“No,” I managed to say.
“It might hurt a bit then,” she said.
I didn’t reply. I was ready for it. I was ready to feel her warm throbbing pushing down inside of my body. I couldn’t wait to feel her cock stretching out my asshole. I wanted to feel her sticky cum filling up my tight hole. I needed it.
She lined her tip up with my hole. She was gentle at first, carefully mashing herself down until her tip penetrated slightly. Then she paused, waiting for my body to relax. I was biting down on my tongue, trying my best to stay relaxed and unclenched.
She sunk in deeper, at least an inch. I clenched again but then I managed to relax after she stopped for a second. “Don’t stop,” I said suddenly. “I don’t want you to stop. Just fuck me. Use me like a sex doll.” My heart was pounding harder than ever before. My cock was so hard—it was drooling all over those hotel bed sheets.
She didn’t reply. She just started pushing in. And she was right—it hurt, but I managed not to scream. I just bit down on my tongue and kept my face pressed firmly into the pillow. I squirmed a bit and then I began to groan and moan. But she kept pushing until her pelvis was pressed against my ass. “You’re so tight,” she said. But I couldn’t reply.
She started to thrust in and out, slowly at first. The pain was intense. I felt like my asshole was being stretched as wide as a coke can, but I knew it wasn’t that bad. Her cock was big, but it wasn’t that big. “Fuck,” I finally groaned, but she didn’t stop. Good—I didn’t want her stop.
Her hands gripped my waist tightly. She clenched her knees tight against my hips, holding me from squirming. She came down hard with loud slaps. The pain was finally starting to go away, being replaced by a swirling euphoria—the euphoria I knew I would feel. I could feel every inch of her throbbing dick inside of my body. I could feel her bulbous tip exploring my back door, pushing against my prostate, making my legs tremble. There was a nice tingle in the tip of my cock.
“Oh God, it feels so good,” I moaned. There were tears in my eyes, pooling on the pillow.
I gripped two handfuls of bed sheets. I pulled them hard, still squirming and groaning. She was coming down hard now—and fast, fucking me like I was her dirty whore. God, it felt so good. I didn’t want it to end. I wanted her to last forever—but I could already feel her cock bloating up. I could hear her straining to hold back her cumshot. I knew she wasn’t far—I knew she wouldn’t last long. But I didn’t realize I wouldn’t last long, even though I wasn’t even touching myself.
I could feel a warm pooling between my legs. It took a moment for me to realize I was feeling cum—my own cum. She was making me have an orgasm. She was pressing against the perfect spot in my asshole. I screamed out and began to tremble, and that warm puddle continued to grow. And then I felt another warmth, deep inside of my ass. She was coming, filling me up deep. A big smile crossed my face and I felt more satisfaction than I’d ever felt in my life.
But it was short lived. Once my cock was finally empty, a new thought came into my head: she was a prostitute. After this night, she was going to go and find new guys to fuck, new guys to fuck her. She wasn’t mine. She would probably feel the same euphoria with other guys—and that made me sad. I wanted her to be mine. I wanted to be hers.
“Don’t do it,” I said as she stepped back and grabbed a tissue to wipe her cock.
She looked at me with wide eyes. “Do what?” she asked.
“This—don’t be a prostitute—or an escort, or whatever you call it. Don’t do it.”
A slight smile crossed her face. “I have to.”
“Why?”
“Because I need the money,” she said.
“Get a different job.”
“Easy for you to say,” she said. “You’ve got a skill that you can turn into work. I don’t have that. The only special thing I’ve got is this cock.”
“You’re beautiful,” I said.
“That’s not a skill,” she said.
“Are you kidding me? Do you know how much money photographers like me pay to shoot beautiful models? I know models who charge a thousand dollars an hour—and they get more work than they can handle.”
I watched as a glimmer grew in her eyes. But it disappeared quickly. “But I’m no model. You saw me the other day.”
“You were one of the best models I’ve ever worked with. You just need a portfolio and a bit of experience.”
And that glimmer
returned again: maybe she didn’t have to sell herself for money—at least not sexually.
My heart was pounding. I sprung to my feet and then I felt her warm cum dribbling out of my gaping asshole. “We can do a bunch of shoots and get a portfolio going. I’ll make some calls to photographer friends, so you can get some more experience. I even know some runway guys who need new faces. It’s easy—all you have to do is walk up and down a runway. There’s a certain way you have to walk, but you can figure that out with YouTube or whatever, I’m sure of it. And hell, you can stay with me until you’re established,” I said. “And, I don’t know, maybe you can stick around. Just don’t go back to this—don’t let strangers have their way with you. There are creeps out there, and some of them will hurt you. Be a model—you’ll be a great model.”
She stared into my eyes with a conflicted smile, like she wasn’t sure if I was pulling her leg or not. “Really?” she said.
“Those pictures I took of you were some of the best pictures I’ve ever taken. You’ll blow up fast. You have to believe me.”
“No—I mean, I can really stay with you?”
“I’d love it if you stayed with me,” I said. “I’ve only got the one bed though, so I hope you don’t mind sleeping with me.”
Her smile grew. She tried to hide it with her hand, as if she was embarrassed by how happy she was. “Okay, I guess I can give it a shot.”
I bit down hard on my tongue in an attempt to hide my own smile. I couldn’t wait to get started. There were so many shoots I wanted to do with her, and there was so much I wanted to do with her in the bedroom. I now had my very own pretty model, and maybe a sexy trap girlfriend on top of it.
THE END
SISSY HYPNO
Kent is a regular ladies man, until he has his confidence rattled when a beautiful blonde mistakes him for a woman. Now he’s desperate to get his confidence back and he’s willing to do anything.
Big Hard Girls Page 38
