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For a change I had a lot of cash laying around, so decided to go into city and see what kind of trouble was available. Put on a fresh pair of jeans, good walking shoes and caught the train south. An hour later was walking towards Times Square and all the porno shops there. Got a bunch of tokens at the first place I entered and watched the latest shemale tapes that had come in since my last visit. This was just about the time of the Brazilian’s flooding the market with tapes. Their shemales are really pretty but the tapes are dull and unimaginative. After an hour of this I could feel the fever building so bought a copy of Screw Magazine and walked up to a bar on 7th Ave. The place was empty at 2:30, so I picked a table with good light, ordered a scotch from the bored bartender and began to read the in-call ads for shemales and transsexuals.
It was a good week, three pages of ads for tranny incalls; I eliminated all but the mid-town ads and narrowed my choices down to three. Then with a fresh scotch and a pocket full of quarters went to the phone booth in the back. On the first two, which I had visited before, there was no answer, got an answer on the third. She sounded happy to get an early afternoon caller. Getting the directions, I gulped the last of my scotch and headed out to grab a cab. The address was a cross street on the East Side. From a mom and pop store on the corner called the number again and got the exact address, which was a half block up from there.
Walking quickly up the street rang the buzzer for the third floor apartment number she had given me and she buzzed me in. The building was clean and neat, that is encouraging. I climbed the stairs and she was waiting for me with the door half open.
The apartment was clean and well furnished. Large living room dining area and a railroad style kitchen. There was a guy sitting at the dining room table, the shemale assured me he would be leaving, which he did almost immediately by way of a back entrance. We then got down to business; the going rate at the time was $50 for a half hour and $100 for an hour. Not having come all this way for a quickie I opted for the hour and gave her a hundred.
She took the money into the bedroom, probably to a safe box. Coming back into the living room, she had changed. Now she was wearing a short robe, this displayed her tits nicely and a pair of high-heeled shoes, she walked with an exaggerated swing of the hips, which showed, off her charms below. She was very well hung, perhaps two inches longer than myself but not quite as thick. The cock peeked out at me through the folds of the robe.
“Lets get better acquainted, honey.” She said as she sat beside me on the couch. The one nice thing about incall is that most will neck with you a bit. We kissed and my hand immediately went to her cock, she opened her legs so I could explore her better. Next she helped me off with my clothes and doffed her robe. Now we were embracing skin to skin. Her breasts were quite nice I took a nipple in my mouth and began to suck it, then moved to the other.
I was getting excited and starting to get an erection. She moved my head into her lap and I took her cock in my mouth and began to lick and suck her, mine got harder. Her hand was on me as I sucked her, massaging my growing dick. What happened next and how it happened is unclear. Moving quickly she had me face down on the couch straddling me from behind. Her cock probing me until she found my opening. Guiding it forward she entered me, I could feel the foreskin role back and the pressure on my prostate, then the feeling of fullness one gets as the cock enters and you know you are about to be fucked.
The cock sliding into me took me back in time twenty years to my very first sexual experience that did not involve my own hand. I was going to school in California. Young far from home and lonely. One particular weeknight was with a group of fellow students at our local hangout, the club on the school grounds. Five or six of us were sitting there in the early evening talking about school, future assignments and in general telling lies about our other activities. About 8 PM we were joined by one of the instructors. This was unusual, and we were all impressed to one degree or another by his lowering himself to talk with mere students. It got even more impressive as he bought us a round of beer, then a second, while seeming interested in our mindless prattle. He was hunting.
One by one the other students left until by 10 PM it was only he and I. He bought me another beer; he was going to seduce me. At 10:30 the club was empty and he offered me a ride to my pad. I gladly accepted since I didn’t have a car at the time. Didn’t realize it but I was now his date for the evening. On the other hand by the time we got to his car and drove the two blocks I could have walked it twice.
He searched for just the right parking spot and found it, parking between two cars. No casual nightwalker would see us in the car. The radio was playing softly in the background some California station that could be described as music to fuck by. The front seat was illuminated by the streetlight.
His car was very impressive, for a Chevy/Ford kid from upstate, this was really something. He told me all about it, the car was a six year old Jaguar Sedan, the L model, stick shift with two jump seats in the back. The large back seat was also convenient for other purposes beyond sitting, as I would soon learn.
We talked some; there was a silence as two strangers were trying to think of something worthwhile to say. I would learn later that this pregnant silence is when the seducer is about to make his move and find out if he will get lucky with his date tonight.
Moving his seat back as far as it would go he unbuckled his pants and pushed them down exposing his cock and balls. I watched in the dim light fascinated because I had no idea what was going on. He rolled the foreskin of his dick back exposing its head, he was semi-erect. I felt a twinge in my own cock as I gazed at his. I had never really looked closely at another mans cock before and as I gazed at his mine began to harden. The car was getting warm. Then he turned to me and said: “Suck me.” I moved toward his groin and his right hand on my neck guided my head into his lap. Holding my neck he fed me his cock with his left, I took his cock in my mouth and began to suck. My balls pulled tight and I got hard as the cock entered my mouth. Sucking him seemed the most natural thing in the workd and he knew then, he was going to get lucky tonight.
Had you asked me an hour early if I would suck someone off, the answer would have been an emphatic no. Now I had a cock and my mouth sucking it and had a raging hard-on while doing it. As naïve as I was at that time couldn’t imagine anything beyond my sucking on his cock until he came in my mouth. There was a big surprise waiting for me in the back seat.
He let me suck until he was hard, then he said: “Get in the back seat.” The purpose of that large back seat was about to be revealed to me in a very intimate fashion. Clambering into the back, he followed behind me. He reached around and unbuckled my trousers pushing them and my shorts down to my knees. My cock got even harder something was going to happen, my cock didn't know what but it liked the anticipation. Reaching around front he felt my erection and seemed satisfied with it, he pushed me forward onto my chest.
His foreskin moving over my nether area gave me goose bumps as it searched for the place to relieve the pressure I had built up with my mouth. It found the target and entered me, very easily; I was ready to be taken. I could feel his long foreskin slide back as the head of his dick slid down that smooth channel until he was totally in me; the pressure on my prostrate got me even harder. I had a feeling of fullness and pressure from the cock now deeply inside of me, and it seemd as if I could feel his cock in the pit of my stomach. Then he commenced to fuck me, hard and deep. It was a warm evening and soon the back of the car smelled of sex as we both began to sweat from the effort. With his hands he pulled on my hips and I responded by pushing backwards so he could get deeper inside me.
The windows of the Jag were soonfogged over; anyone walking by now would know someone was being fucked in the car.
In retrospect I cannot say if I really turned him on with my mouth or he just liked ass in general, but he kept at my opening for a good half hour thrusting away, forcing me deeper into that back seat. He finally came with three or four very hard thrusts then held in me as he relaxed. His cock softened and he withdrew.
We didn’t say another word just dressed and parted company. I went into my place leaking cum, took a quick shower and went to bed, it was only midnight, and I slept very soundly.
Never in my wildest dreams did I think my first sexual experience was going to be as a girl blowing a guy so he could get hard and fuck me like a woman. Had always imagined that sex would involve a girl and pussy, something of a shock to find out I was the girl and had the pussy waiting to be fucked. I went into seclusion after that trying to deal with this new aspect of my personality.
Didn’t see the old guy again. Shortly thereafter moved to Wash. D.C.
I kept pretty much to myself at first still dealing with the new me. A very evocative phrase kept running throught my mind, almost biblical: I have lain with a man and he has know me as a woman. That kept reverberating through my mind.
One day the head of the file room where I was working handed me a file and said: “Read this, it is really disgusting.” That had my interest so I sat down and read the file. The part he was referring to was a psych report on a homosexual. It was a blow-by-blow account of his sexual activity from age fourteen till twenty-one. The report was more like pornography than a medical evaluation.
Two things happened one I began to realize I was not the only one in the world with this experience and the text caused a fever to start in me that I couldn’t explain.
The rest of the day I was on fire. Maybe the old clerk was attracted to me this and this was his way of coming on to me, don’t know. Later after work I went to a bar and had a few beers to try and calm down, that didn’t help. So I took a walk along Columbia Pike smoking and thinking about the report. I had been out for a few minutes walking in the dark of the early evening, when a car passed me and slowed. He turned at the next corner circled the block and drove slowly up behind me again. At first I thought it was a cop out to arrest me for loitering. That wasn’t the case; the guy rolled down the window and asked me if I wanted a ride. I got in.
“Where are you headed?”
“No place just out for a walk.”
“Well I am just out for a drive.” His right hand rubbed my thigh.
Ten minutes later we had parked on a dark side street, he ran his hand up my jeans to my cock which had gotten quite hard, I reached over and tentatively felt his which was also getting hard. He unzipped his pants pushed his trousers down and pulled his cock out and I followed suit and pulled my trousers down both of us now had our members out and began to play with one another. We felt each others growing erections. I ileaned over and laid my head in his groin and took him in my mouth and began to suck him. He grew harder in my mouth as I blew him, until finally he came deep in my mouth, I continued to suck him until he went soft. He then jerked me off. After that we pulled up our pants and he drove me back to where he had picked me up. The whole scene took less than 45 minutes. Now I knew how to put our the fever.
Thereafter I learned the file codes for this sort of activity and read every one of the psych reports that came through on homosexuals. While I wasn’t thrilled with the way they were treated when arrested, at least I knew there were lots of people out there with the same inclinations as mine. The Supremes and the their decision to allow pornography was still in the future so these were a great substitute and perfectly legal. While some of the reports were dry recitations, most were written as if the doctor was trying to get excited himself; or as titillation for subsequent readers, there were a lot more details than were necessary.
The reports served two purposes for me, these were ordinary individuals that had gotten swept up in raids and forced to detail their lives history. I didn’t want to be one of them so I was going to be careful. In addition to being good jerk-off reading they showed me just how wide spread these practices were, and to a degree put me more at peace with myself.
When I discovered shemales found the right combination of girlish charms that put me at ease. First it was video tapes from California that hit the market. Then found aforementioned magazine, published weekly with page after page of shemale incalls. So whenever I had some extra bucks would seek one out in the city. Have never had a bad experience with incalls, which is more than I can say for getting hustled at the shemale bars. Not to get to far off track, the Porn industry has failed to keep up, they are still operating with the 1930's mentality. Earlier was watching a tape of a couple, she was an extremely attractive brunett. The couple meets out of doors, he blows her to erection then she fucks him in a couple different realistic postions. However at the last moment she pulls out to and jerks herself off. No way does this happen in real life, you have her in you and you keep her there until she is done. Of course then the camera can't see it. A little upgrade is needed here. Sorry to run off like that.
Back in the apartment the shemale was deep in me doing a very comprehensive job of fucking. For only the second time in my life some one had found the secret of how to enter me and make me their woman. It was a very competent workman like job she did on me. As she came she grabbed my hips and raised them to get in as deep as possible as she shot her load in me. Then she collapsed on top of me. I could feel her cock soften in me, she pulled out, got up and went into the bathroom to wash me off her cock.
I sat up and felt her leaking out of me. She returned a couple of minutes later all cleaned up dressed only in the high heel shoes, hips swaying, cock swinging. “Did you like that honey?”
“Yes” I replied, “it was sort of unexpected thought.”
“You needed it, there is still some time on the clock.” She said as she sat down beside me.
So I got down on my knees between her legs and sucked her off. She let me lick and suck her until she was ready to pop again, then she pushed deeply into my mouth and held me there as she came.
Once we both calmed down I dressed and left. Had to take a cab and even that was uncomfortable due to the recent fucking my ass had been given.
Once I got by that initial pick up in D.C. became active, both with men and women. Over the years I tried on occasion to let my pick-ups fuck me, none of my encounters could enter me, either they were two soft, too inexperienced to know how or it hurt me. So gave up on that and confined myself to blowjobs both giving and receiving on my late night forays.
The first experience and the shemale all those years later had the touch I guess, either that or they would not be denied access to what they wanted. Looking back can think of three instances where offering myself up would have been the appropriate thing to do. Once was in D.C. with a very sophisticated guy. I was very coy that night due to a bad experience a couple weeks before. Should have let him use me, stretched out on the bed and given myself up to him, he would probably have been a through and thoughtful lover. As it was we just sucked each other off. Then once in Virginia went home with this young guy, he had his own apartment in his parents house with a separate entrance. It was a good place with the security you need, there is someone else that would have been competent and done a good job. The last one was a pick up upstate, he was very affectionate, we necked and played with each other for about an hour before getting into a 69 and bringing one another to orgasm with out mouths. He was such a nice individual he should have been rewarded. But life goes on and we can’t go back.
This all took place in the pre HIV/AIDS era, as you will note there is no mention of protection anywhere here, all bareback. On the distaff side the pill was just coming in and most of the girls were on it, so you didn’t need a condom with them either.
There are no earthshaking conclusions to be drawn from this, just a mildly interesting tale. -->
Sherry
- 30.06.2020
- 19
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