T's First Escort


I'd been waiting for about twenty minutes before the doorbell rang. Earlier that evening I decided I would finally take the plunge. I went online to Craigslist and, under the Casual Encounters Section, I found the list for Men Seeking Transsexuals and another list for Transsexuals Seeking Men. Of course, pretty much all of the ads were for escorts.

A few years ago I came across a site involving shemales (a term I now know is not preferred). At first I was just curious but that quickly turned into fascinated. The women were incredibly beautiful and I was instantly hooked. I find myself now desiring to be submissive to a transsexual "top".

I have joined sites as well as found many free ones to spur on my fantasies. I joined a transsexual dating site about a year ago but have had no success in meeting anyone in my area. It seems that every other state has many more "tops" than here (the grass is always greener). I have recently started looking into TS escorts and have found a few sites.

After several months of searching and working up the nerve I decided it was time to just go for it. Several sites show escorts that are visiting the area, but I was weary of them. I chose to contact a girl that lives locally as I figured it would be a safer bet.

I chose an ad for a woman named Carol and after several starts and stops called her. It was a Thursday afternoon leading into a four-day weekend. She answered the phone and I was greeted to an extremely sexy feminine voice. I told her about myself and, I learned that she was 28 years old 5 foot 9 and having seen her picture in the ad I knew she was sexy. We talked for about 5 minutes and she asked me when I would like to meet her. We settled on the next day (Friday) at 7:00 pm. I told her I was looking forward to it and we hung up.

The ring of the bell startled me out of my train of thought and I went to answer the door.I opened it to a tall, busty, blonde, wearing a black dress, covered by an overcoat. Her dress was split to the thigh, revealing a set of long, slim legs. Her bust was spilling over top of her neckline.She was a very feminine girl with big, round eyes and lovely curves. She was magnificent. I had never hoped for someone as beautiful as her to be a shemale. She wasn't just pretty for a shemale either. She was pretty even by regular girl standards

"Hi, I'm Carol," she said. I nervously introduced myself and ushered her inside as she giggled.

"Why are you so nervous sweetie? Is this your first time with a girl like me?" She asked sweetly. I nodded. "Great, I love first timers. Why don't we move this into the bedroom?" She took my hand and led me to the room.

"Take your pants off." I hesitated a little before starting to comply.

"Now!" she screamed as I hastily pulled my shoes and pants off, "Underwear too!"

My raging hard cock sprang free immediately, standing at full attention and a tiny bead of cum was visible leaking from the tip already.

"Mm," she said as she began to stroke it softly. She continued stroking it slowly at first. I groaned, leaning my head back and waiting for her to give me more. Her hand felt great, but I wanted something else. I wanted to feel her warm wet lips, the same wet lips that had kissed me all over a few minutes ago, wrapped around my cock sucking me dry.

She must have read my mind, and it wasn't long before I had gotten exactly what I wanted. She started out by teasing me with her tongue, licking the tip for a few seconds and then moved down to my balls.

She licked and sucked each one, one at a time, and I groaned at the incredible sensation. From there, she ran her tongue up the length of my seven inch cock to the head, swirling it around the head before finally swallowing me whole. She took my entire length all the way to the back of her mouth and immediately began bobbing her head in a perfect rhythm. I was in heaven, as she sucked and stroked me

I could feel the pressure building up in my balls, and I knew if I did not stop her soon I was going to cum way too soon for my own comfort; grunting, I tensed up and bit my lip. "S-Stop," I struggled to say., "I'm gonna...cum."

"Mm," she hummed with my dick still in her mouth. The vibrations sent shivers up and down my spine and I gasped, lightly pulling her hair but not hard enough to hurt her.

"I'm going to cum...if you don't stop,"

"Good," she said stopping. She stood up and started taking off her dress. She took off her dress, revealing the most amazing breasts I've ever seen. Big but still perky, I'd guess a C cup, maybe even a D. I knew they were fake, but I didn't care. They were perfect for her tall frame. She took off her jeans, and I saw that she tucks her cock between her legs. She had lace panties and through them I saw she had a small bush of red hair as I noticed the carpet matched the drapes. She took her panties off, and out flopped the most impressive cock I've ever seen. It was easily 9 inches and so thick, but I could tell it wasn't even fully hard. My heart skipped a beat when I saw this monster, when we were texting I told her that I'd like to try taking her in my ass, but I was starting to have second thoughts seeing it in person.

"I see you like my toy." she said with a wicked grin as she sat on the bed. "This is when we really start having fun."

I could feel the heat coming off of it on my face, and smell the musky aroma as I stuck out my tongue slowly, and licked the tip of her shaft as though it were some kind of taffy. There wasn't much taste to it really, a little salty, and a bit warm too. I gave it another lick, and then a third, slowly getting over the uneasiness of it all and finally gathering enough courage to actually take her into my mouth.

I closed my mouth around the head, and my wet lips slid down over the length of her shaft, taking in as much of her as I could manage before she hit the back of my throat and I gagged. I pulled back up slightly, and then moved back down a little further, but not far enough to gag myself again.

My tongue swirled around the head of her shaft, and Alice moaned, leaning her head back and running her hand loosely through my hair.

"That a boy," she sighed, "suck that cock baby, just like that."

I started moving my head up and down a little faster, sucking harder and also stroking as I sucked. It was surprising how well I was doing with this, considering I had never even considered sucking dick in my life. Carol did not seem totally convinced that was true though, and she brought it up as I sucked and licked at her dick.

"You sure you've never done this before?"

"Mmff," was all I could manage, since my mouth was quite full. Alice laughed, and then moaned again.

"Well, you're pretty good for a first timer. I'm very impressed right now."

She pushed me away suddenly, stood up from the edge of the bed and shoved me back onto the mattress before climbing on top of me. At first I had no clue what she was doing, until she planted her ass on my chest, her cock inches from my lips and then she slid forward and shoved it back into my mouth.

She leaned over me now, thrusting her cock down my throat gagging me in the process. I grunted, choking, saliva running down the corners of my mouth. I could feel her wet balls pressing against my chin as she fucked my throat with such skill, I almost felt for a moment like it was supposed to be this way. Like I was supposed to be laying here, being treated like a cock sucking whore by a hot ass fucking shemale. Just as I was starting to adapt to what I was doing, Carol put an end to it by pulling her dick from my throat and slipping off of me quickly.

"Turn over and get on your hands and knees, right now."


"I said turn over, on your hands and knees, right now you little whore!"

Wow...she had suddenly become very demanding. Oddly enough though, the way she spoke to me seemed to turn me on even more now. I obeyed, turning over, but apparently not fast enough because as I rolled over I felt the searing hot sensation of her hand smacking me across the ass.

"You little bitch," she said. "I'm going to pop your anal cherry, right now."

I believed she would; I knew she was going to ram that big cock up my tight virgin asshole, robbing me of my heterosexuality. And' yet I was still so aroused, I stayed in the position waiting for her to do so...why was I so aroused?

"You want my cock, you whore?"

"Agh," I yelped as she slapped my ass again.

"Say it," she yelled. "Say you want my fucking dick."

"Ah, I want your fucking dick!"

"You'll call me Mistress!"

"Yes Mistress, I want your fucking big dick Mistress!"

"Good fucking boy...I'll give you just what you want you little slut."

She spread them wide, examining my hole, and tracing her index finger over it before leaning in and starting to lick my ass crack. Her wet tongue lapped at my crack and I moaned, surprised that it felt so good. This was the first time I had ever received a rim job, and I was actually disappointed that I had waited so long... I should have tried it much sooner.

As she continued eating my ass, her tongue diving into my hole, she reached between my legs and took hold of my cock and started stroking. I moaned, biting my lip at the combined pleasure of her wet tongue on my ass and her hand firmly gripping my cock and jerking me. She stroked my cock faster and faster, until I was just about ready to cum... and then she stopped, delivering yet another stinging smack to my ass causing me to jump in surprise. I heard her laughing behind me, and again felt her pulling my cheeks wide apart. Then I felt a finger pressing against my now wet and well-lubricated hole pushing into me. I tensed up a bit at first, and she rubbed my back. "Don't tense up," she instructed me. "It'll make it hurt more."

I listened, and tried to relax and felt her finger slide deeper into me without much of a problem at all really. She started moving in and out, and rubbing my prostate, and I moaned, my cock stiffening almost instantly. She sensed the increase in my pleasure and started working to carefully insert a second finger into me and spread me a little wider.

"Fuck," I hissed as I felt my hole stretching, two fingers pushing deep into me now. It was the weirdest thing I had ever experienced in my life, no doubt about it, and yet at the same time it still felt strangely good. I gripped the bed sheets, panting as she started slowly thrusting her fingers in and out of me, fucking my ass with her hand.

"Your spreading real well for me slut toy," I heard her whisper to me, "You like the way my fingers feel in your ass?"

"Oh fuck...yes,"

"Yes...yes Mistress you mean?"

"Yes...Mistress Carol," I corrected myself.

"Good boy," she said happily. "Let's try three fingers now."

Three fingers, knuckles deep in my tight virgin ass... and very soon, she would replace them with something much bigger than fingers. I wondered how that was going to feel... if I would even be able to handle something like that. Something that big, eight inches total I assumed, deep in my ass.

"Does my little slut like having his ass played with?" Carol's voice cut through the fog her fingers were making in my mind. Her kinky words only further heightened my arousal.

"Oh God yes Mistress, I love it."

She removed the three fingers from my hole, and gave me a hard smack on the ass causing me to jump and bite down on my lower lip. I felt both hands on my hips, and movement behind me, the bed shaking slightly as she slid closely behind me. I felt something hot being pressed against my hole.

"You ready to take this big dick up your little virgin ass?" she said.

"Yes," I panted. I didn't realize my breathing had become so heavy. I felt overcome with anticipation as I felt her cock rub up against my ass. I had used toys on myself, but this was going to be my first cock. And, I had never had anything quite as big as Carol's cock in my ass before. Suddenly, the head was pressing into me. My asshole was resisting and I tried to relax it. I felt Carol push hard, and the first couple of inches invaded my ass.

"OH! Oh shit! Oh shit!" I screamed. I hadn't expected Carol to push it in so fast. It hurt and felt like there was a small flame inside of me. Carol moaned deeply, tilting her head back.

"Oh, wow," she said. "You're so fucking tight. I don't remember the last time I fucked an ass this tight." She pushed forward and another few inches slid in.

"Oh God!" I pleaded. Carol very slowly started to slide her cock out. Soon, only the head was still inside me. I was anxious for her to take it all the way out so I could recover from the initial shock. Carol didn't move for a little bit, finally letting me adjust to her thickness. It took some time, but, finally, most of the initial pain began to fade. Then she slowly started to thrust in and out of me.

"You're so fucking tight slut," she whispered softly. "Your ass feels so fucking good on my dick"

She pulled almost all the way out and pushed back in, she repeated this action slow and tenderly allowing me to get a good feeling. Each time she did this, I felt less and less pain until it was almost entirely evaporated. By then, she had already built up a pretty good rhythm. she was moving at an incredible speed, slapping my ass for her own enjoyment, our moans and the sounds of her slapping against me filled the room as she started to pound me into submission. I could only cry her name as she continued to slam inside of me harder, grabbing onto my hair roughly.

"Fuck... ya like that don't ya," she panted out, "You've been a bad boy and you deserve this big, hard cock in your ass don't you?" Again I was unable to respond, but apparently this was unacceptable to her this time. She slammed her cock all the way into me and stopped there. "I asked you a question Lance. What do you deserve?" she barked at me.

"Guh... ahh... uh... a cock..." I managed to gasp out. I felt the wave beginning to subside and wanted it back badly. She slapped my ass again.

"Tell me what you deserve Nick?" she yelled at me. I could actually feel her physically making her cock throb inside of me.

"Uhn... your big cock..." I continued. Another slap. I really wanted her to keep pounding me now. The wave of pleasure kept ebbing away further and further. I tried to bump or grind against her but she held me tight against her.

"What do you deserve Nick?" she yelled again.

"Your big, hard cock in my ass!" I pleaded, "Please fuck me! Please pound me with your huge cock." Part of me couldn't believe the words coming out of my mouth, but at that point I'd have said anything to get her to continue fucking me.

"Please fuck me...?" she paused clearly looking for another response.

"Mistress!" I yelped. "Please fuck me mistress! Please, mistress pound me with your huge cock!"

"Oh Nick! You learn so fast! I'm so proud of my new playtoy!" she cooed to me. Then she reared back and slapped my ass one last time before laying both hands on my hips and plowed my ass with renewed vigor. The subsiding wave of pleasure surged forward again as she plumbed new depths inside of my newly explored love canal. I could hear and feel myself panting harder as the wave crept closer. I began rocking back into Carol as she crashed into me with ever more powerful strokes. I wanted this. I needed this! Harder and harder she slammed into me pushing me forward on the bed. Now she was moving at an incredible speed, slapping my ass for her own enjoyment, our moans and the sounds of her slapping against me filled the room as she started to pound me into submission. I could only cry her name as she continued to slam inside of me harder, grabbing onto my hair roughly.

"Do you like that Nick." she asked breathing heavy. "Do you like my fucking cock in your ass baby?"

"Yes......Mistress," I struggled to say with the way she was fucking me.

"Say it louder Nick," she yelled, smacking my ass hard as she continued to slam inside of me.

"I love your cock in my ass Mistress!"

"Do you like being treated like a dirty little whore, Nick?"

"Yes Mistress, I do."

"Yeah? Mm, I bet you do. You love my cock in your ass, because your a dirty little cock slut, aren't you?"

"I do Mistress, I do love your cock in my slutty ass."

"Good," she replied as she gave my ass another slap and pulled out. She grabbed some pillows and prompted her back against the headboard making her cock stand straight up. She motioned for me to get on her and ride her cock. I quickly oblige and swung my leg over so I was staring into her eyes.

But instead of immediately forcing herself in, she applied slow pressure all the while intensely staring into my eyes. The head of her cock popped into my ass and a moan involuntarily escaped my lips. She released my balls and placed both hands on my hips, pushing me further onto her prick. She felt huge inside me, a burning pressure that only seemed to be getting worse as I slowly sank down her length. My breathing became shallow as I tried to deal with the discomfort of taking this gorgeous woman's dick in my ass. She seemed to delight in my expressions of pain, her cock growing fatter within me every time I moaned in distress. Just when I thought she would surely kill me with the length of her cock, my ass came to rest on her thighs and she bottomed out inside me.

I was trembling from the intensity of being fully skewered by her, I leaned forward, holding onto her neck for support. "You did it, slut.," she praised me. "I'm all the way inside you. Now comes the fun part." She started pulling out, only slightly at first, then sliding her prick back home. Gradually she pulled further and further out until she was truly fucking me, sliding me up and down her cock with every thrust. I began rocking back and forth on her dick. Back and forth I rocked, feeling her moving around inside of me, rubbing against my sweet spot and sending waves of pleasure rolling through my body. She was loving it just as much as I was, I could tell. I started moving up and down, riding her cock, slowly at first.

Each time that I came down on her dick, I would clamp my ass around it and she would moan softly. Then back up I would lift myself...right before bringing myself all the way back down again. I had adjusted well enough by now that there was nothing to it, really. It felt incredible, and it was much easier for me to be a little more aggressive than I had been. She flipped me over, putting me on my back with my legs wrapped tightly around her, in missionary. My hands moved up and down her back as she started thrusting in and out.

"Oh shit," I gasped, as she was pushing me hard into the mattress with her body weight as she drove her cock as deep into my ass as it would go. She was hitting just the exact right spot as she was making me moan loud. My moans grew louder and louder with every thrust, at this point I didn't care if any of the neighbors heard. I was in complete ecstasy as Carol continued to pummel my ass. The slapping of her groin up against my ass was nearly as loud as my moans. Carol was now fucking me as hard as she could. Her groin slammed up against my ass over and over again and she fucked me with all the energy she could find. As she slammed in and out, I started to moan and pant and writhe around underneath of her. I couldn't help but note how unmasculine I sounded...it bothered me just a little, but not enough to stop me from continuing on. It felt too good to stop just because of the sounds that I was making.

"Oh fuck yeah," said Carol. "Is this why you came here? Is this what you wanted?"

"Yes," I managed to say over the loud sounds of my ass getting fucked silly. "Yes, fuck me hard."

Carol carried on, slamming in and out, grunting and panting as she shoved her breasts in my face. Moaning, I started sucking on her nipples as I raised my legs a little higher, allowing her better access. By now, any thoughts of pain or discomfort were gone and I was absolutely consumed by the pleasure of her cock. My cock began to swell up and I knew I was getting close to an orgasm. My whole body went into a fit of spasms as I cried out in pleasure. I managed to lift my head off the pillow and saw that my dick was literally squirting cum all over myself.

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byHORNYWRITERTS© 6 comments/ 30017 views/ 56 favorites

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