A Tranny Whores Tale

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His adventures with a sexy and raunchy tgirl.
3.1k words
4.18
139.7k
53

Part 1 of the 2 part series

Updated 06/07/2023
Created 01/22/2009
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Ok, so I love tgirls. Absolutely adore them. I've had many experiences at this point, but want to share one. I looked around in the local paper and found this one TS escort. It was early morning (about 5am) and I went to see her. Even though I have had experiences, I get enthralled with nerves and excitement every time. It's almost paralyzing. So I go into her apartment and she walks me to the living room. As usual I'm listening for someone hiding in other rooms and trying to convince myself to do it. She was stunning. About 5'8" 150 or so, dark brown, what looked like c ups, long jet black hair, a seductive look, feminine and smooth skin. We exchanged the usual pleasantries as she hinted towards her offering ($$$). I stalled, completely a nervous wreck. I love when I'm like that. It usually means I'm so in need of a tgirl I'm completely losing it. I told her that I was very nervous and just wasn't sure. She was really cool and didn't rush to kick me out as many probably would. I stayed for about ten minutes, before I got up and said "I'm too nervous". She chuckled at me almost as if I were a Lil boy. The embarrassment charged me. But I still gathered my self and left. I told her I would call again, if I got the nerve and left.

A few days later, I was drinking a Lil in the house late night. I went through my usual ritual of calling and text messaging all the ladies I knew, looking for a Lil company. No one was available so I click on a Lil internet porn. Of course it charged me and that mixed with the alcohol charged me and began thinking of all the pretty t girls. I looked at a some t girl porn and then began going through my phone looking for my patient t girl friend (we'll call her Elle). I called her and she was kind enough to chat with me a bit. I told her how nervous I was that night and we chuckled. She asked me some of my interest and suggested we get together that night. She happened to be only about ten minutes away and suggested I pick her up and go to her "brothers' apartment. Being a Lil more courageous I said sure, took one last large swig of the potion and was on my way. I reached to the intersection she informed me of and she was there waiting. She was with 2 other t girls. She said bye to her girls and walked towards my car. She was dressed like a whore and I loved it. She had a tight yellow tee shirt on with one of those cute jackets that stop at the rib cage and a very tight pair of, what almost looked like boys shirts or very short spandex biker shorts. The shorts were yellow also and she had knee high black boots with heels. As she walked to the car I became more and more pumped. I though to myself "wow, I'm going to fuck her good". She got in, said hello and we began to drive. She gave directions as I went. We talked casually about our last meeting and discussed more of my interest. I told her I really wanted to suck her and fuck her.

We reached our destination. I parked and she immediately got out and began walking towards the apartment building. I jumped out to follow. She walked ahead of me as I attempted to catch up. I watched her whore ass as it jiggled in front of me. I looked around the neighborhood I was in and wondered if anyone was up and watching me as I followed this t girl hooker into the pits of lust. "Was there anyone, who knew who she was and was taking enjoyment in seeing me walk towards my fate? Are they calling me a cocksucker or fagot as they watched me walk down the street?" The thought turn me on.

We climbed the three flights of stairs, walked pass a number of apartment doors and again I thought about any tenants who might be up listening to Elle's high heel clicks up the steps or through the hallway, being all to familiar of the sound at this hour. Maybe there was someone who was thinking "There goes that whore fagging out another man whore" I loved it. Maybe a friend or a friend of a friend also lived in the building. After all I wasn't in a totally unfamiliar neighborhood. The thought of being recognized made my heart pump so fast; I had to take deep breaths as we approached her door. She knocked on the door. I guess her brother was there. The door opened and she said she'd be right back. I waited in the hall hoping no one would come out and see me. After 2 minutes or so she came out and following her was an apparently open gay guy. He stopped and looked at me with a look that suggested "hurry up and finish cocksucker" as he walked down the hallway away from us two. Perhaps he was sleep and upset to be disturbed. Either way, the fact he saw me and the look he gave was humiliating. I didn't want anyone to see me, but he did. The danger encouraged me.

Elle and I walked into the apartment and it was relatively dark. I could make out the layout, but couldn't tell you the colors in the room. At this point something changed. Having done this before I pulled out Elle "offering", raised it up for her to see and walked to the table next to the TV and placed it down. All she said was "take your clothes off. I stripped to my undershirt and boxers and she said "take off everything. Socks too." I did as I was told. She casually walked to the kitchen and back, still full clothed and stood and the living room entrance and stared at me. I immediately walked to her and boldly wrapped my hands and arms around her in total desperation for her touch. I kissed her neck and felt her curves. At this point the alcohol is in full effect, I was pretty drunk. I said to her "I want to suck it and I want to fuck you. I'm going to fuck you right?" I thought her answer would be a confident yes because we talked about it a lil on the phone and on the way. I told her how I went to see another girl who said we would fuck and when I got there she refused. So I thought it was a sure thing. She said "no, I'm going to fuck you". This startled and excited me. I didn't plan on doing that. I only received anal once prior (great story, remind me to tell you about it) and she was somewhat small, it didn't last long, and I wouldn't let her do very much.

I said to her playfully and aggressively "no, I'm fucking you" as I grab one of her supple breast hard and pulled her closer. She responded with her own aggression and repeated the phrase "no, I'm going to Fuck YOU". Then pushed me a bit, grabbed my arm and turned me around. Now, I am stronger than her, that I was sure of, but her aggression caused me to respond passively and I turned as she attempted to control my body. With my back to her, completely naked, she put her arm around my waist and grabbed my cock. Then she patted my ass lightly and chuckled. She squeezed my nipple and wrapped her hand around my throat. Never letting go of my cock, she spun me around to face her. Still fully dressed and clamping my stiff dick, she approached my left ear and said "get on your knees and suck this dick". I got down immediately, although still concerned about fucking her. She stepped back and pulled her tight little shorts off. I don't know how she did it, but she had a sweet 7 " or so chocolate bar stuff in there. It sprang lose. She reached into a vase nearby and got a few condoms. I remained on my knees. She put it on, threw the others on the couch and stepped back towards me. She held the crown of my head and simply said "open". Oooo, I was so fucking ashamed for being sub pig for this girl, but I opened and started sucking. She kept telling me to look up at her when I sucked her dick. I paused and said to her in mid suck "you going to let me fuck you?" I had lost masculine/dominant hand ten minutes ago and knew it. She pulled it out of my wet mouth occasionally and slapped me with it. She began calling me names. "You bitch", "dick hungry faggot" and more.

She suddenly stopped fucking my mouth and told me to get on the floor. By this time I was hers for anything. I crawled to the center of the living room and laid on my back. She grabbed some lube from the same vase and parked herself on the floor right at my base. Without any words she lifted my legs and greased my hole. It felt like I was 2 years old again, getting my diaper changed. I had never been in that position before. I was nervous, drunk and overwhelmed with lust in my blood. She lathered me up and just entered me with reckless abandonment. It hurt.

She put my legs on her shoulders and tried to drill a hole to China. I tried desperately to clamp my ass closed. I pushed with my hands at her hips to attempt to slow her momentum. I thought about how stretched out my asshole would be. "What if my ass retains a huge gape?!! What am I to do if the next woman I'm with sees or feels how open my ass is?! That can't happen!" It added to the experience. I bitched, I moaned and I staggered her thrust in attempts to minimize the damage and pain. I did not give my ass away, it was being taken from me. It didn't belong to me at that time.

She began to get frustrated because I wouldn't allow her to tee off on my born again virgin ass. She said "Come on now, give me that fucking ass, you can fucking take it...open that ass up for me!" She then, jumped up and sat on one of the two couches and told me to come to her. I did what I was told. She straddled my hips and had me ride her. An inch or two slid into me, but I still resisted much more. She pumped upwards and got up to about four inches in me. I moaned and howled. I almost did not recognize my own voice.

This still did not satisfy her! She pushed me off of her like the many times I have, while ravaging a willing female subject. I fell back a bit and stumbled. I couldn't look her in the eye being so humiliated. She went to the other couch and sat down and again told me to come. I did what I was told. She told me to go back to the other couch. I started walking back and she said "no, fucking crawl over there and then crawl back". I did what I was told. When I got back she grabbed me by the back of the neck and said "You don't wanna take this dick, bitch? You know you love being my faggot. Don't you? Huh? Don't you, you little fucking whore?" I didn't answer, but she shook my head up and down like I was I voluntarily nodding in agreement. It was humiliating. Her dick stood straight up inches from my face. She put another condom on and pushed her cock into my esophagus. I sucked. I loved it. She began rubbing my face gently seemingly admiring and caressing my facial features. I have been on the opposing end of this exchange many times. There's nothing like a pretty, soft skinned female sweetly numbing on my cock. I usually feel and massage a woman's face while receiving a good dick suck. I guess Elle was showing the same sentiment to me as I savored her shemale cock. I felt soft, almost loved and appreciated the way she touched my face, and then she slapped the shit out of me, SLAP! It was hard but not bruise causing. It completely woke me up. It drove me crazy.

When she noticed I enjoyed it she did it again and then again. Each time she did it off beat and tried to catch me by surprise. Elle even put in a few combos Slap! Slap! I sucked and moaned and craved it all she cursed me, and then complimented me. Caressed me, and then stung me. I think I lost my mind with pleasure.

She suddenly stopped, withdrew her rod from my mouth and pushed me off of her. I stayed on my knees, she got up. Elle bent down and lifted me by the hips, another exchange I recall seeing from the other end. I was on the couch on my knees, forearms on top of the head rest, ass spread wide. She treated me like the whores you see in porn by playing and spreading my ass. Elle slapped it and chuckled. She was enjoying herself. She crouched over and sucked my balls and managed to pull my dick from behind and suck it. She grabbed the lube and got my ready. She kept sucking and violated my asshole with two fingers. The feeling had me convinced I would follow this bitch wherever she goes, if that's what she wanted.

Elle stopped and laid on the floor next to the couch. I got up immediately and got on the floor too. She grabbed me by the hips and placed me on top of her again. She did it casually, like she had been packing my asshole every morning for years and expected it. By now I was a cock craving nut. I no longer held back. I sat on that dick and let it push my insides aside and get to the hilt. I hurt soo good. I didn't care about my gaping ass anymore, I wanted to be fucked. I began bouncing, increasing my frequency with each reinsertion. I got into it. Elle noticed and smile and said with a belittling tone "OO, look at you. Are you riding dick? You taking dick faggot? You are going to be my Friday pussy. You like that, sweetie?" I began responding "Yes I want you to have this ass. Yes. Take my hole. Stick it up in me..." Our sweat was building. Then she stopped again, to my disappointment. Again she pushed me off of her like I didn't matter and stood back up, asked me if I wanted some milk. I knew what that meant. She snapped her fingers and pointed towards the couch. I got back on the couch on my knees. She pushed into my ass with a even stiffer cock than before. All this drove me mad. I pushed my ass muscles outward to accommodate Elle's' sweet milk muscle. I wanted it all the way in now. I released sounds out of my mouth I couldn't duplicate today (unless she was here). I growled, I moaned, I yelled and encouraged her to penetrate and savagely interrogate my hot hole. We continued in this position for about five minutes when her pace increased and Elle started breathing even heavier than previously.

She pumped and pumped and the sound of her soft skin slapping up against the back of my thighs balls and ass was resounding. She began moaning, mouth open wide "Ughhh, ughhh, ughhh, I'm cumming in your ass boy, Oooo, yeah I'm going coat you asshole." Then her hardest stroke ever, she slammed into my ass one last time and stayed there as she began shooting hot fresh cum into my ass. I went quiet, face tight with pleasure and pain. I wanted to pay attention to her cock as it pulsated from shooting streams of nectar. I listened to her moan. I felt her dick jolt with each shot. I could feel the warmth in my ass. It was something. I took the moment in. I felt how her hands felt on my hips and back. I took in the sub position I was in with a big live wire rod up my ass. I just stayed there.

She eventually pulled out. I still remained in the same position, overwhelmed. She chuckled and asked "You ok?" I nodded yes. She reached around at my cock. I was hyper sensitive. She lubed me up and started jerking me from behind. I got into a rhythm. She stopped and told me to put on my boxers. I did it and got back in position on my knees. She jerked me a minute or two from behind and whispered in my ear "I don't want you to ever forget this so I'm going to give you a souvenir" The feeling of her voice vibrating my ear drum, the nights' humiliation and her gooey hand jerking my dick inside of my draws caused me to flood my boxers (boxer briefs). The stream of nut seamed endless. It was all over her hand, my cock and balls, and the front of boxers. She casually removed her hand and went to the bathroom to clean herself. She came right out and said "That's your souvenir...now take it home" and she handed me my shirt and smiled at me kindly. I thought to myself what a fucking mess, but just got dressed to complete the experience. Fully dressed I could feel my own cum flowing down my crotch and trickling to my ass, but my sick ass like that thought too. I told her "ok I'm leaving" very nonchalantly and started to the door. She sat down on the couch and grabbed my wrist when I started walking pass her and brought me close. She gave me one more slap, but softer, toying with the thought of earlier smacks. She then gave me a peck kiss and hugged me around my shoulders and neck warmly. It concluded, I left the apartment. As I walked down the stairs I see the gay guy at the lobby area. He looked at me, knowing to some extent, what had happened. The humiliation made me want more of it. He gave me a final glare as I left the building, with dry mouth, stretch hole, raw cheek, cum souvenir and all. That's it.

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4 Comments
wolf9696wolf9696over 11 years ago

loved it, want lots more, maybe throw in some face spitting

PetiteWendyPetiteWendyover 13 years ago
Superior

Not usually my cup of tea but this is really superior, intelligent, authentic, sexy.

AnonymousAnonymousover 13 years ago
F#CK!

That was soo descriptive and hot!! Write more!! please!

TheBiOneTheBiOneabout 15 years ago
Great Work!

Keep 'em cum-ing :D

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