So I figured I would take advantage of the situation. “Do you mind if I put you into a pose? I have one in mind, but it’s too hard to explain.”
“Go for it,” she said. So I walked up to her and I gently spun her around. I put my hands on her side and bent her over slightly. Then I turned her shoulders before bringing my hands down to her hips.
“We’ll just turn your hips slightly,” I said. I was standing close to her, my pelvis nearly pressed against her ass. She decided it would be funny to press her bum back and grind it against my crotch. She giggled and snorted.
“What’s this pose? The doggy style pose?” she asked before snorting again.
“It’s a popular pin-up pose,” I said. I stepped back and snapped a few shots. She wiggled her bum in the air and then she started twerking. She giggled and snorted some more, and then she even flipped up her skirt and flashed me. I was slightly disappointed to see no bulge in her panties. She was just a normal girl with normal girl parts.
“How’s about this. I’ll lie on the ground and you straddle me. It’ll be good for some low-angle shots.” I smiled and got down onto my back. She didn’t hesitate, sitting down on my lap with that big, crooked grin on her face. She grinded her butt against my crotch and then let another little snort slip. I had to admit, her snorts were kind of cute. She didn’t need any direction. She put her hands behind her head and then she tilted her head back and closed her eyes. She got right into character, pretending to have an orgasm—and it actually made for a set of pretty good pictures.
Then she threw herself forward and planted her hands on my chest. She looked right into the camera lens with that teenaged seductive look. “Are you getting good shots?” she asked.
I nodded my head. “I think you’ll like them.”
“Do I look sexy?” she asked.
“I think you look sexy.” I felt my cheeks turning a shade of red.
She rubbed her bum against my crotch. “It doesn’t feel like you think I look sexy.” She had a big grin.
I let a nervous laugh slip. She sat back upright and then she reached down for my belt. She started undoing it. “I want these pictures to look sexy, so I need some way of knowing.” She yanked my belt away with a swift tug and then she tossed it aside. She didn’t hesitate before going for my fly. She unzipped it and reached in for my cock. She pulled it out and then giggled and snorted again. “See? If I was really being sexy, this would be much harder.” She lifted it up with one finger and then she let it fall down, limp on my pants.
I laughed nervously again.
“Keep snapping photos,” she said.
So I rose up my camera and continued to snap shots. She grabbed her tits again and squeezed them. Then she grabbed her top and pulled it down, over her rack, exposing the red lace of her bra. Her tits were huge. She unclasped her bra in the front and then pulled the cups aside, letting her amazing jugs fall loose. Her nipples were perky. She grabbed them between her thumbs and pointer fingers and gently rolled them, making them harder and perkier. Then she looked down at my cock. “Still not doing it, huh?” she said. I kept snapping photos. I could feel my cock throbbing and getting harder, but apparently it wasn’t enough for her.
She stood up with her heeled feet planted on either side of my chest. She hiked up her skirt and then she pulled her panties aside, exposing her plump and moist cunt. A small part of me was disappointed when a small cock didn’t flop out. She slipped two fingers between her plump lips and she started to rub. She giggled and let another little snort slip. “What about this?” she said. She rubbed fast, squirming slightly as she began to moan. I kept snapping pictures. She looked down at my cock again. “Better?”
I nodded my head. I changed my point of focus from her face to her dripping pussy.
She sat back down, rubbing her moist cunt on my abdomen, leaving a wet streak as she got herself repositioned over my erection. She used her right hand to stand my cock upright, and then she pushed it easily into her warm, wet hole. She started bouncing. “Am I naughty?” she asked.
I took a deep breath. It felt good, but it could feel better. I grabbed her by the hips and lifted her up, until my cock flopped out from her wet hole. Then I pulled her back down, closer towards me, so her asshole was lined up with my dick. She giggled nervously. “What are you doing?”
“You’ll like it,” I said, lining my throbbing tip up with her tight back door.
Her face was suddenly red. “I’ve never taken it up there before,” she said.
“You’ll like it,” I said again. And then I pulled her down by the hips, thrusting up with my hips. It took a second to penetrate. She gasped as soon as my tip was inside of her. I let a long, deep sigh out. Her eyes were closed tight and she was biting her lip hard. Her asshole was being stretched for the first time ever—it probably hurt a little bit, but I knew she would get used to it. I sunk my cock a little bit deeper. I loved the feeling of her tight anal walls throbbing against my cock. I let my head rest back and I closed my eyes and I imagined Jenn was sitting on my cock, with her ball sack and cock resting on my pelvis. I imagined my dick was sinking deeper and deeper into her tight trap hole. I let a sigh of my own slip through my lips.
“It hurts,” Kyla said as she continued to take more and more of my hard dick.
“Just give it a minute,” I said, hoping she would quiet up. Her voice was ruining my fantasy. I couldn’t picture Jenn as long as Kyla was talking.
Kyla squirmed and sunk deeper. She let a pained moan slip and then she planted the palms of her hands against my chest. Suddenly she was the one pulling her ass up and dropping it down, doing all of the work, stroking my shaft with her tight asshole. It felt nice. I closed my eyes and brought that image of Jenn back into my head. I imagined her cock getting harder and harder, lifting up off of my pelvis, dancing from side to side with every penetration. I imagined a bout of pre-cum oozing out from her erect cock.
And then Kyla started to moan. “Oh God, it’s so tight,” she said, taking me away from my fantasy. Her pussy was dripping warm juice onto my pelvis. I closed my eyes and tried to pretend like it was pre-cum—but there was just too much for it to be pre-cum, so I imagined Jenn was coming: a seemingly endless amount of warm cum, emptying out onto my pelvis. With my eyes still closed, I reached down and wiped that warm moisture up my abdomen, to my chest. Her asshole clenched my cock hard and she groaned again.
“Fucking take it,” I said, reaching for her hips and pulling her down hard.
“Oh God,” she cried again, once again erasing that image of Jenn from my mind. I strained to bring that image back, but now Kyla was becoming too vocal. “I love the feeling of your fucking cock throbbing in my asshole. Oh God, it feels good. Fuck my little asshole. Fuck my slutty little butt!” It was sexy, but not as sexy as Jenn. I couldn’t stop thinking about how I wasted my chance to fuck a beautiful trap. I couldn’t stop thinking about how badly I wished Jenn were there with me and not this eighteen year old slut who was skipping her last period class for this pointless photo shoot.
“I’m coming!” she yelled, and then a bout of warm fluid splashed down my lower half. She was a squirter in a big way. She squirmed and groaned and clenched two handfuls of my chest. And it was enough to make me come, deep in her asshole. She yelped and then giggled and snorted as she felt my hot load filling her up deep. Once I was empty, she stood up and reached around back to catch my creampie with her hand. “Oh my God, there’s so much!” she said as it pooled into the palm of her hand, out from her gaping asshole.
I forced a smile as a cold tingle ran down my spine. My trap fantasy was more overwhelming than ever before. I couldn’t stop thinking about it. I couldn’t stop hating myself for not making a move on Jenn. I needed to see her again. I needed to get her alone one more time, so that I wouldn’t end up with a lifetime of regret.
CHAPTER IV
I started by searching the Internet again for those pictures, to see if she ever ended up using them. My search once
again turned up no results. All of my anxiety from the week before came back to me. She probably hated the photos and she probably didn’t want to hear from me again. But I knew if I didn’t try, I would regret not trying forever.
So I wrote up an e-mail. “Hey Jenn, it’s Michael. Hope things are going well for you, and I hope you liked the pictures. I was wondering if you wanted to do another shoot. I’ve got a few ideas in my head and thought you might be interested. Okay, let me know!” I sent the message before I even read it over. And then I read it over and cringed at how stupid and desperate I sounded.
I couldn’t pry myself away from my computer. I kept refreshing my inbox, hoping her response would come quickly. It was 2019—everyone got their e-mail to their phone, and everyone had their phone on them at all times. So why wasn’t she replying right away? Surely she’d read the message, right? I paced around my apartment, feeling stupider and stupider, and then finally I heard the ding of my e-mail inbox. I rushed over to my computer.
“Hi Michael,” said Jenn. “The shoot was fun. Like I said, I really love the photos. But I’m out of town at the moment and not sure when I’ll be back. Cheers!” My heart sank into my stomach. It was an obvious rejection. Who leaves town without knowing when they’ll be back? And why wouldn’t she add something like, ‘I’ll let you know when I’m back so we can shoot again,’ unless she just didn’t want to see me again.
Did I make her uncomfortable during our shoot? Or did she really just hate my photos?
I went to my bed and planted my face into my pillow. I wanted to shout. I should have made a move. I shouldn’t have ended our session so abruptly. I should have spent more time processing each photo. Maybe she was expecting more than just twelve shots—maybe I should have sent her twenty-four, or even a hundred. Or maybe I just needed to accept the fact that she wasn’t interested in me.
It was later that night, after lots of anxious theorizing, when I decided to casually search through the Internet to see if there really was such a thing as a tranny escort website. Sure enough, there was, and it was shockingly easy to find. As I entered the page, I was overwhelmed by pictures of surprisingly pretty girls, though none of them were terribly convincing. They all tried to hide their big Adam’s apples with choker necklaces. But nothing could hide their broad shoulders.
Some of the girls were more convincing than others. And some were horribly unconvincing, though I assume there is a market for that. I was just curious to see if I could find a girl to satisfy my trap fantasy, which had only been getting worse and worse since my photo shoot with Jenn. I searched through pages and pages of girls. I couldn’t believe how many there were in my town: hundreds. Had I seen any of these girls out on the streets before? Had I flirted with them before? Had any of them ever asked to do a TFP shoot?
It was on the eighth page of results when I froze. On my screen was a picture that I took, of Jenn on the hotel bed. The image was cropped, which explained why it didn’t show up when I searched it on Google. Or maybe the tranny escort website blocked Google’s image search.
As I clicked on her profile, I noticed my hand was shaking. So my craziest theory was true: Jenn actually just needed the pictures for her escort website. She was selling herself online, and her rates weren’t even that bad. For two hundred bucks, I could have her and her slippery cock for an hour. I stared at that screen for fifteen minutes, flicking through those pictures that I took, and a few others that she took with her own camera phone. In one shot, she was naked and holding her hand in front of her cock, with her other arm over her tits. Her skin looked smooth and buttery. I suddenly remembered the smell of that amazing perfume she was wearing. I suddenly remembered that warm glimmer in her eyes when she smiled for the camera.
How could she have been a prostitute? She was too gentle and sweet and innocent. Even once she’d had a few drinks, she was still timid—almost too timid for being a model, never mind sleeping with strangers.
I stared at her profile for a long time as my mind spun around in circles. My heart was racing, and it took a few minutes before I realized why: I was considering buying her. I could afford her, no problem, and I knew she was in my area. I kept telling myself that I couldn’t do it—I couldn’t sleep with a prostitute, but my heart just continued to pound because I just couldn’t convince myself.
It was easy to come up with reasons why I should do it: she was affordable, I knew she was convincing and beautiful, I’d always wanted to sleep with a pretty trap… But there was another reason: I nearly tried to sleep with her when I had her in the hotel room. And what difference did it make if I had slept with her in that hotel room versus sleeping with her over an arranged date? At the end of the day, I was still sleeping with a transgender prostitute.
My mind was spinning so quickly and everything became a blur, as if I was nearly blackout drunk, unsure of how I got from one place to another. The next thing I remember, I was typing out an e-mail from a newly created e-mail address, with a fake name of course. I would have stopped myself had I been in the right state of mind, but the next thing I remember is checking my outgoing mail to see that the e-mail was there, sent, waiting to be read by the trap hooker I desperately wanted to sleep with.
And then I was in my bed, staring up at the ceiling, waiting for my computer to ding, worried that I wouldn’t hear it over the sound of my heart pounding against my ribcage. I’d just messaged a transgender prostitute, asking if she was available. Was I insane? At some point in the past few days I’d lost my mind, though I couldn’t pinpoint when exactly.
I’m not sure when I finally fell asleep. I wasn’t asleep for long before a crack of sunlight crept into the room to wake me up. And even though I’d hardly had any sleep, I sprung from my bed and bolted over to my computer. I saw the bold letters of an unread message, and it was from Jenn, who went by ‘Trisha’ when she was turning tricks.
“I’d love to meet up with you. Are you free tonight? I’ve got my whole night free,” she wrote. And I wrote back quickly, with many typos as my hands trembled across the keyboard.
“Tonight works. I can swing by around 8 PM.”
This time she replied quickly, as if she was at her computer when the e-mail reached her inbox. “8 PM works. I’m at the Berggren Hotel on 4th, room 301. See you there.”
I stood up and realized my legs were trembling even more intensely than my hands. A cold sweat bathed the back of my neck. I had a date with a trap prostitute. I had a date with one of the most beautiful girls I’d ever seen—definitely the most beautiful trap I’d ever seen. But was I really going to go through with it? Could I really sleep with a girl who slept with men for a living? Could I really sleep with a chick who was technically not a chick at all? What if I suddenly panicked once the pants were off? What if she became offended that I used a fake name and that I tracked her down? Could she sleep with me knowing I knew her true identity?
CHAPTER V
I couldn’t believe I was actually standing at that door, after a long day of pacing around my apartment with the worst anxiety I’d ever felt in my life. So many times I managed to convince myself that it was a bad idea—there was even a moment of relief when I finally sat down on my couch, convinced that I wasn’t going to show up at that hotel. I’m not sure when that relief fluttered away and I ended up back on my feet, pacing up and down the hallway. I couldn’t not do it. I knew that I was never going to feel satisfied until I gave it a try. I knew that Jenn would always be on that website, available for me whenever I was ready, so it made no sense to delay the inevitable.
I raised up my fist to knock on the door. The skin on my hand was white, and the skin on my face was probably just as white. I don’t know how I mustered up the courage to knock on that door—though maybe it wasn’t courage at all. Maybe it was just absurd stupidity. I still didn’t know how I managed to convince myself to show up for that date. I don’t know how I managed to get dressed in my best clothes, make the trip down to the ATM, and then travel across town to
my date with a well-hung prostitute.
I could hear her heels tapping as she approached the door. I could still turn around and run. I wanted to run but now my legs were frozen, my joints stiff. I tried to take a deep breath of air into my lungs but my lungs were also stiff. So all I could do was stand there with a terrified look on my face as she slowly pulled that door open.
And then somehow I managed to force a smile. “Hi,” I said, showing too much teeth.
I watched as her expression dropped and her eyes became wide. “M—Michael?” she said.
I slowly nodded my head. I hadn’t come up with a good excuse as to why I tracked her down and used a fake name. I knew it would look weird and maybe even creepy. I probably should have used some of my free time that day to come up with some sort of excuse—but what could I have said? What sequence of words could have made her feel relaxed, and not like a crazed photographer was stalking her?
She stepped aside and said, “Come on in,” with a timid voice. I entered the room slowly and looked around. I’d shot in that hotel before, so I was familiar with the layout of the rooms. In fact, I was pretty sure I’d shot in that very hotel room before, with another model—who sucked my cock on the very bed I was now looking at.
“Do you want something from the mini bar or anything?” she asked me as she awkwardly skirted by me. She was clearly uncomfortable, and I should have seen it coming. Why did I want this? Why did I want to sleep with a girl who would obviously be uncomfortable with the idea of sleeping with me? Was I actually insane? Was I actually a perverted stalker?
“I’m okay,” I said, taking off my coat and gently placing it on the back of the desk chair. “I’ve shot in this room before.” I don’t know why I said it—maybe just because it was the only sentence my mind could muster.
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