I punched her number into my phone. I had to take a deep breath because I realized I hadn’t taken a breath in nearly a whole minute. I could feel that my face was turning red. I pressed the dial button. The phone started to ring. I took another deep breath.
“This is Erin,” a surprisingly feminine voice answered—but it wasn’t perfectly feminine. There was a tinge to the voice that gave away that extra fun between her legs. Though would it have given her away had I not known any better? Would she be as convincing in person as she was in her ad? Or was I setting up a date with a man in a dress?
“Hi Erin, this is… uh… this is a client looking to—I mean—a potential client, and I… uh…” I wasn’t able to get my thoughts straight. I was even overwhelmed by her voice in my phone. How was I going to go through with spending a night with her?
“You want to set up a date? Are you free tonight? You can meet me at eight at the Delta Lounge. Sound good?”
I was silent for a moment as my brain begged me to say no—but my newly adrenaline addicted heart was begging me to say yes. “Sounds good,” I said.
“See you tonight,” she said. And then she hung up. It all happened so quickly. Didn’t she have any questions for me? Was that all there was to hiring a prostitute? Was the deed done? Had I already broken the law?
It was only 3:00 PM. I had to endure five tedious hours before my date. I spent most of that five hours pacing around my apartment, trying to talk myself out of the stupidity that I was getting myself into. What if I was meeting with a cop? Would I end up on one of those pubic lists? Would I show as a red dot whenever a young family searched their area for sexual deviants?
I took a long shower. “What’s wrong with you?” I asked myself over and over. But still, I continued to get ready for my date. I ironed my best dress shirt and my best pair of dress pants. I even shined my dress shoes, which probably wasn’t necessary as I’d only worn them a couple of times since buying them. I must have brushed my teeth eight times. I was terrified of having bad breath. I tried to eat dinner, but I was only able to stomach a few bites as the adrenaline churned in my gut. Finally, after a gruelling four hours and a half, it was time to leave for my date. My joints were stiff as I walked out to my car. My hands were trembling as I curled my fingers around the steering wheel. I begged myself one last time to turn around, and then I started my engine and headed off towards the Delta Lounge.
I couldn’t even remember why I was seeing Erin. For what reason was I meeting with a tranny prostitute? What was I trying to prove to myself? Did this have something to do with getting Angie back? Or had I lost my sanity at some point over the past few lonely months?
I pulled up to the Delta Lounge with ten minutes to spare. I spent those ten minutes in the car, staring at the door, waiting for her to show up. I wanted to see her before I committed to meeting with her. But I didn’t see her walk through that door. She was either late or already inside waiting for me. My watch beeped, letting me know it was time to face the horribly uncomfortable destiny I’d created for myself. I stepped out from my car slowly and then I tried to shake out the rigidity in my legs. I looked around at all of the cars, to see if any of them looked like they could belong to undercover cops. But why would a cop go undercover as a tranny? Was there a transgender on the police force?
I walked into the lounge slowly and scanned the whole area. It was dimly lit, with quiet music playing through the speakers above. There were a few nicely dressed women at the bar, and a couple of guys in suits drinking at a table. I wondered if I would even recognize Erin. I couldn’t remember what she looked like now that I was trying to recognize her. Was she one of the girls at the bar?
Then I saw her at a booth in the back, and I knew it was her instantly. My heart stuttered and I remembered every little detail of that ad, right down to shade of her lipstick in that schoolgirl photo. Would she put on that schoolgirl outfit once we were up in her room?
Before I could run away, she looked over at me and smiled. She lifted her hand into the air and waved me over. I had to take a deep breath before the ability to walk returned to my legs.
She was wearing a nice red dress, with a lipstick that matched perfectly. Her eyeliner was dark, contrasting the platinum colour of her hair. “You came,” she said with a grin as I approached the table. I could still hear that slight masculine tinge in her voice.
I had to clear my voice before replying. “Of course I came,” I said, forcing a smile. I stood next to the table, not sure what to do next.
“Are you going to sit?” she asked.
So I took a seat. I straightened my shirt and then I straightened my back. I wasn’t sure what to say. I looked into her eyes and she looked back into mine with a grin that made butterflies flutter in my chest as if I was on a rollercoaster that was just starting to drop down a steep hill. “You look nice,” I said.
“Thank you.”
I was suddenly aware of all the other people in that lounge. I didn’t look over at them, but I could feel them looking over at me, knowing that I was meeting with a whore. I wondered if they were cops—maybe the tranny’s partners. There was a glass of ice water on the table; I reached for it and took three big gulps. “Thirsty?” she asked.
“I guess so,” I said. I still wasn’t sure what I was supposed to say. What was the point of the initial meeting? Was it just to make sure that I wasn’t a serial killer? Or was I supposed to be saying something to win her over? “Did I say that you look very nice?”
She laughed. “You did,” she said. Then she looked past me and waved her hand in the air. My heart skipped a beat. Was she waving over her police friends? Was I about to be busted? A waiter was suddenly next to our table, making me jump. “Could he get a whiskey? A double—and make it neat. And two shots of something strong —just surprise us.” The waiter went off to get the drinks, and then Erin looked back into my eyes. “You need to relax. We’re going to have fun tonight.”
I nodded my head slowly while forcing a smile. “Of course,” I said. I couldn’t think of anything else to say. I was relieved when the drinks showed up. She slid one shot towards me and then grabbed the other.
“Cheers,” she said before pounding it back. She drank it without flinching, the way a man would take a shot. I slammed mine back. It was stronger than I was expecting, making me cringe and cough. I nearly spat it up, but I managed to get it all into my stomach. She laughed. “That will help,” she said.
“Thanks,” I said. And then she slid the whiskey towards me, and I realized she ordered it for me. I picked it up and draft half of it in a single gulp, hoping it would cut my nerves. And then I noticed that she was still staring into my eyes, without flinching, still with that grin on her face, as if something about me was funny. My skin was crawling and cold. I really was living through one of my own nightmares—and I was putting myself through it.
“Once you’re done that drink, we can go up to my room and just get to it,” she said with a calm, casual voice. She continued to stare into my eyes with that grin, as if she was enjoying my uncomfortable reaction. I knew that I could just leave. No one was forcing me to go up to that room with her. She didn’t even know my name, or anything about me for that matter. Once I was gone, I would no longer exist to her and she would no longer exist to me. So what was keeping me in that seat?
CHAPTER V
She had a small room on the second floor, with a view of the parking lot. As soon as we walked in, she walked over to that parking lot view and shut the curtains. “You’ll just have to give me a few minutes to change,” she said. She walked over to a suitcase and then pulled out a handful of clothes. I saw pink and black, with sheer lace and tulle, all scrunched into one of her hands. It must have been a small outfit. I caught a whiff of her sensational perfume as she stepped by me. At least she smelled just like a woman—and she looked like a woman too. At least I wasn’t about to sleep with an obvious man: some guy with broad shoulders and some five o’clock shadow. Though she was
still technically a man, at least as far as doctors were concerned.
I stepped into the room and looked around. There was a television on the dresser, but I left it off. I took a seat on the edge of the bed and wondered if I was supposed to get myself undressed. I reached down for my belt, and then I remembered the possibility that she was a police officer. What if she was in the bathroom calling her squad mates? I didn’t want to be naked when they burst through that door. So I just sat quietly, listening to the dying traffic outside, and the sound of my heart thudding against my ribcage. And I wondered: Am I really going to go through with this? And why?
The bathroom door opened, making me jump. She stepped out. Her legs were clad with black lace stockings and she was wearing that tiny schoolgirl outfit, which seemed especially tiny now, as if it had shrunk since she’d taken her escort profile pictures.
“What do you think?” she asked.
She was beautiful. Her breasts were perky and her curves were perfect. But it was only a few seconds before my eyes were drawn down to her crotch. I tried to see if I could spot the bulge. Her little skirt wasn’t quite long enough to cover her panties—it wasn’t quite long enough to cover anything at all. “You look nice,” I said. My voice cracked as if I was a thirteen year old seeing his first porno.
“You can come over and touch me if you want,” she said.
I took a deep breath and slowly rose to my feet. My body trembled with a combination of terror and excitement. I really did want to touch her, even though I knew that I would be touching a man. I gently placed my hands on her bare sides. Her skin was warm and soft. I moved those hands up, onto her soft black top. I could feel the sides of her breasts. She had implants, but they were soft and professionally done. “You can touch them,” she said. She saw that I was staring at them. So I moved my hands onto them carefully. Surely if she was a cop, she would have stopped me by now—right? Now police officer would let a stranger fondle her breasts…
I squeezed. I could feel her hard nipples through the thin fabric of her shirt. I took another deep breath. She was gently biting her bottom lip, as if my squeezing actually felt good—and maybe it did. “Everyone tells me that my ass is my best feature,” she said.
So I reached down with both hands, around her body. I put my hands on her ass. And she was right. It was the perfect mixture of perky and squishy—not too big and not too small. I squeezed and spread her cheeks, and then she let a little moan slip out from her lips. Suddenly, she had both of her hands on my belt buckle. Things were starting now—soon there would be no turning back.
Her perfume was strong as I stood inches away from her. While she was looking down at my crotch, I took a moment to inspect her body completely, trying to see if there were any signs that she truly was biologically male. But she had narrow shoulders, wide hips, long, soft hair, and I couldn’t spot an Adam’s apple at all. I was beginning to wonder whether or not I’d read the ad correctly—maybe that extra fun between her legs was just her pussy—and maybe that ‘T’ next to gender was just a typo. Maybe those breasts weren’t implants at all. I reached up and squeezed them again, trying to make a final determination. But before my brain could process anything, her hand slipped down my pants and her fingers curled around my cock.
“Ooh,” she said. “You’re big.” Her grip was firm but delicate. She started to stroke and massage my length. My mind was suddenly blank. What was I thinking about before? What was I so worried about?
She moved with expert precision, pumping and massaging and stroking. She did this little move where she rolled my tip gently with her thumb and pointer finger. I’m not sure I’d ever gotten so hard so fast in my life. She used her free hand to tug down my pants.
“I never got your name,” she said.
“George,” I replied. And then I realized I should have given her a fake name—but it was too late. And it probably didn’t matter. It’s not like she could have tracked me down with my first name alone. There were probably thousands of people named George in that city—and as far as she knew, I wasn’t even from that city. Maybe I was just a guy on business from out of town.
She ran her clenched fist up and down my throbbing length. I was starting to worry that I would come before ever finding out if she was truly a trap or not. “You’re really good at that,” I said. I bit down on my tongue in an attempt to chase away the euphoria. I wanted to last a long time. I was paying three hundred bucks for the hour—so I figured I should at least last half and hour.
“So it’s your hour. What do you want to do?” she asked.
I bit down on my tongue. What did I want to do? A part of me just wanted to bend her over and stick it in her asshole, without pulling her panties too far to the side, so I could remain oblivious to her reality. But another part of me wanted to push my comfort zone and face my fears. “I just want to see where this goes,” I said, taking a deep breath. She took a step closer to me, pressing her chest against mine. I grabbed her hand and moved it off of my cock, so that I could be just a bit closer to her, with nothing between us. Then I looked into her eyes. “Can I kiss you, or is that weird?”
“Kiss away,” she said. So I closed my eyes and kissed her. My heart fluttered and she probably felt it against her chest. I was kissing a biological man—but strangely, it didn’t feel weird. Her lips felt just like the lips of all the girls I’d kissed before her. In fact, her lips seemed even softer and more delicate, but her tongue was more confident. She pushed it through my lips and wrapped it around my tongue, and it felt nice. I moved my hands up and down her sides. I felt that perfect ass again, and then I even spread her cheeks and pressed a finger under her panties, to tease her little asshole. She let a little giggle slip. She had a cute giggle.
And then I felt the reality I was looking for: her cock, hardening in her tight panties, pressed against my erection. I could feel her throbbing and getting bigger. I didn’t move. I continued to rub myself against her, grinding my throbber against hers. She seemed to like it. She was getting hard fast. After getting my shirt off, she gently dug her nails into the skin of my chest. “You’re a good kisser,” she said.
“Thanks. You are too.”
I reached down with both hands and tugged her panties down to her thighs, letting her erection spring out. Then I grabbed it and pressed it against my cock. I used my fist to jerk us both off at the same time. Her body trembled and a whimper slipped out from her lips. Her cock wasn’t quite as big as mine, but it was certainly just as hard, as if she was just as aroused. “Fuck, that feels so good,” she moaned.
She brought her hand up to her mouth and then spat into the palm of her hand. Then, she lowered that hand. I let go of out cocks and she took over, spreading her warm spit up and down our lengths. It felt good—too good. I was once again worried that I was about to bust before we were even finished with foreplay.
I suddenly spun her around, acting on impulse. I bent her over the bed and I spread her beautiful butt cheeks. I sighed at the sight of her puckering asshole. I took my saliva-coated cock and pressed the tip against that little hole. She let a little groan slip. “Be gentle,” she said.
“Maybe,” I replied. And then I started to press my cock into her. She clenched my dick hard, and it felt nice. I waited a moment for her to relax before sinking deeper and deeper. She’d obviously taken a cock before. Her asshole remained mostly relaxed until I was completely inside of her, with my pelvis pressed against her soft tush. “You’re so tight,” I said.
“Just fuck me.”
So I started to pump. I reached around and grabbed her hard erection and gently massaged it while I used her tight anal walls to massage my own rod. I loved the way she moaned and squirmed, and I loved the way her cock throbbed in my fist. I caught another strong whiff of that perfect perfume. I hoped that smell would stay on me for at least a few days, so I could revel in this amazing euphoria for a bit longer. I slapped her ass, making her asshole clench. It was a great feeling so I slapped her ass a few more t
imes, leaving large red marks behind—but she didn’t seem to mind.
“Goddamnit, that feels so good,” she groaned. And then she started moaning consistently, as if she was on the verge of an orgasm. Unfortunately, I didn’t have enough in me to let her get to that amazing finale. I tried to hold back, but the pleasure was too intense. I filled her tight back door with my hot load. I pulled out and watched as it started to pour out of her, and then I stuck my cock back in, pushing that load in deep again.
She stumbled to her feet. Her face was red and her eyes were glowing. She reached out for my hands. I took her hands and she led me to the spot she was just in. She put a hand on my back, so I bent over. My heart was pounding so fast; I was worried it was just going to stop, leaving me dead in a hotel room with a prostitute. She stepped around behind me. She slapped my ass and then spread my cheeks. “Is this your first time?” she asked.
“Yeah,” I said.
“You’re in for a treat.” I felt her warm tip press up against my hole. I tried to remain open for her, but my nerves kept clenching me shut. I bit down on my tongue and took a deep breath, and then she started to push in.
Her cock was thick—thicker than the blue dildo from the board game. She sunk in slowly without stopping. She didn’t even stop when I clenched. I heard her moan and I could feel her veins throbbing inside of me. I clenched two handfuls of bed sheets, and then I curled my toes into the carpet below my feet.
“How does that feel?” she asked.
“So fucking good,” I said. And I wasn’t lying. Her warm tip was pressed right against that sweet spot. She let it linger for a moment before pulling back. I could feel the hard ridge of her tip sliding through me. Then she came down hard, slapping her pelvis against my ass. I gasped. She did it again, and again, and again—faster and faster. I was starting to relax. I could hear myself moaning, but I couldn’t make myself stop. I was squirming and grasping at the bed sheets. She was holding my hips firmly. I planted my face into a pillow and let myself scream out in pleasure. I could hear her groaning loudly as her fingernails dug into my skin. And then I felt it: the hot burst of her cum inside of my asshole.
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