I grew up in a small town, about an hour north of New York City. I had spent lots of time with Playboy and Penthouse magazine, but was not really active sexually through my teens or college years. I mean, I had steady girlfriends, and had sex, but I wasn't a Casanova type, chasing a different woman into bed every weekend.
When I graduated from college, I started going down to New York City to visit friends, and just hang out. On one such trip, I was checking out some hardcore pornography at a newspaper stand, and noticed Screw Magazine. I opened it up, and thumbed through it, and was startled to see the blatant advertisements for prostitutes.
I purchased the magazine, and, upon arriving home, began reading, and checking out the ads in more detail, slowly stroking my cock as I read. When I got to the last few pages of ads, my eyes popped out of my head.
Transsexuals. This was a first for me. I had never heard of them, let alone seen one. Here, in black and white, were several pages of them advertising their services. I spent many nights checking out the pictures they each had in the paper along with their ads. I started buying TS magazines, and as I got older, renting TS movies. I spent lots of time in the Times Square (before the city cleaned it up) bookstores, one of which had live transsexuals in show booths downstairs. Twenty years have past, and my minor distraction has become an active desire. The Internet provides movie clips of whatever you desire, but I was growing dissatisfied with merely viewing movies. I wanted to have sex with one of these wonderful, mysterious, erotic creatures.
I don't know if there are any transsexual escorts where I am living now, but I had decided that the next time I was in a large city, I would find one, and fulfill this long-lived fantasy.
As luck would have it, I had to spend a week in NYC for a business trade show. As soon as I found out I would be going, my heart started to pound. I could think of nothing else for the two weeks prior to my trip.
The day arrived, and I drove down to the city. I checked in to my hotel, and went wandering around the streets and avenues surrounding Times Square. The peep shows weren't on 42nd street anymore, but they were within a few blocks. I found a store with T-Girls, and spent several hours going from booth to booth. I was growing delirious with lust. I had to have one of them. I settled on one particular woman, and tipped her so she would slide a dildo up her ass while I watched. I jerked off while watching this, and shot my load on the window between the booths. I smiled at the object of my desire and left.
After dinner, I decided. That would give me time to recover so I could enjoy this long-time fantasy coming to fulfillment. I spent the rest of the day walking around the city. I didn't need to be at the convention center until 9:00 the next morning, so I was on my own for the day.
Finally, it was dinnertime. After eating, I returned to my hotel room, showered and dressed. I went to a newsstand not far from my hotel and picked up a copy of Screw. I returned to my room, and started reading the current ads. I saw several who looked good, and, believe it or not, several pictures which I remembered from 20 years ago. I figured either they were not photos of the girls, or they just didn't bother updating them. Either way, I passed on those. Finally, I found one.
She was lovely, at least her picture was. She was an ebony goddess. Her ad said she was 5'4, 115 pounds, 36c 26 36, 9" uncut. She claimed to be of Brazilian, African American and French ancestry. She went on to state that she was male to female and was still able to cum.
This is it, I thought to myself, and picked up the phone. A sultry, deep voice answered and we discussed my reason for calling. She said she did out calls, and knew the hotel I was in. An hour was $150, during which anything goes, with no limits as to how many times I could cum. She would bring the condoms. I asked it the picture I was looking at was really her. She told me to look through the peephole when she arrived. If I wasn't happy with how she looked, I should just not open the door and she would leave.
I said ok, I would love to see her, and she said she would be there in about an hour. I had a drink and tried to calm down, but my heart was racing. I could still back out by not opening the door, but I realized I would probably call another girl the next day if I didn't do this one.
I was looking out the window when I heard a knock on my door. I almost dropped the glass I was holding as I jumped. This was it. I put the glass on the table, and looked through the peephole. It was she all right, and she was a vision. I opened the door, and smiled at her, not knowing what else to do. She smiled back, and gave me a peck on the cheek. I stepped back so she could enter the room and closed the door behind her.
She was wearing a white halter-top, with no bra, her nipples plainly visible through the thin fabric. The halter left about eight inches of smooth, firm stomach visible above the waist of a red leather mini skirt, which was maybe 10 or 12 inches from waist to bottom hem. Red garter straps ran down from underneath her skirt to hold up her red, seamed thigh high stockings. Her shoes matched the stockings, and the heels were about six inches. I was taking in this vision of loveliness when she ran her finger along my ear. I jumped and looked at her. She asked if I was happy, or if she wanted me to leave. Not for at least an hour I told her. I offered her a drink, which she accepted, and we discussed what I would like to do. She said she was able to provide me with whatever fantasy I desired, but payment was up front. I handed her the cash, and asked if she would like to take a shower with me. She said she would like that, that most guys she ends up with haven't showered for hours, and don't smell all that pleasant. I took her hand, and led her to the bathroom, where I removed her clothes one piece at a time. When I had her down to shoes, stockings, garter and panties, which were a red thong, I stood back and looked at her. My cock was stiff as a board, and I my breathing was ragged. I knelt before her, and slowly pulled her thong down over her garter straps, watching as inch after lovely inch of her wonderful cock became visible. Once it was all exposed, I gasped. The ad said nine inches, but had mentioned nothing about its girth. It was huge. I watched with amazement as it slowly hardened, right before my eyes. When she was fully erect, it must have been 5.5 or 6 inches around. I moaned, and flicked the tip of my tongue up the bottom of this wonderful, black cock. I had to have it, and moved to take it in my mouth.
"Not so fast lover" she said, and pulled a condom out of her purse. She put it on, and leaned back against the sink. 'Ok, now, suck that cock".
I lost no time, taking her into my hot mouth. It took me three or four passed up and down, but I finally succeeded in getting the head of her cock lodged in my throat. I stayed down on her shaft, using my hands to play with her balls, which were warm, and hanging, loose and full. After a minute or so, I started sliding up and down, sometimes all of it, sometimes just a few inches. I was savoring my first cock sucking experience as well as my first shemale experience. I was on my knees for about ten minutes when she asked if this was how I wanted to spend my entire hour. I got up, and took her condom off. We showered, and then moved to the bed. I put another condom on her, and sucked her until she was hard again. I was playing with her tits and inhaling her freshly showered scent. I was intoxicated. My cock was rigid, and rubbing between my belly and the bed as I ate her cock.
She was running her hand through my hair, and pulled my face off her cock. Smiling at me, she got on her knees, and rolled me on my back. My cock was throbbing with my desire. She smiled at me again, and I could see she had a condom in her mouth. She lay on her stomach, and enveloped my cock, applying the condom as she sucked her way down my shaft. She came off my cock, and looked up at me.
"You're so excited, I want you to cum first so you can fuck me good" she said.
I was in her control whether she realized it or not. I would have done anything she wanted. She went back down on my cock, slowly sliding her hand up and down my wet shaft behind her lips. Very slowly she worked, flicking her tongue along the shaft as she want, flicking it across my glans as she came to the top. I started to squirm, and she sucked me all the way into her mouth, her nose was buried in my pubic hair. She had her hands under my ass, she was pulling me into her. I could not have been deeper into her mouth. Then it happened. I exploded. I had an orgasm the likes of which I had never experienced. She had inserted two fingers into my ass and was actively massaging my prostate. It felt like I came for ten minutes, pumping rope after rope of cum into the condom. Once I was finished, she pulled her fingers out of me, and slowly slid her lips off my condom-clad cock. I was gasping for breath as she pulled it off, holding it tip down. She had the tip, which contained my cum, in her mouth, and was flicking her tongue and lips around it. She lay it on my face, telling me she loves cum, but only from people she knows are safe. I could relate to that, so I smiled. She then asked me it I had ever eaten cum. I replied, telling her hers was the first cock I had sucked.
"Well then, open up baby" and she poured my load out of the condom into my surprised mouth. I was surprised, but found the taste all right. In fact, I enjoyed it. I rolled it around my mouth, savoring the bitter, salty taste. She watched me as I did this, smirking behind half lidded eyes.
"I love to watch men eat their own cum" she said, rocking her hips so her cock and balls rubbed on my chest. I reached across my chest and took her cock in both hands, feeling it's satiny hardness and warmth.
"You want to stick your cock up my ass now?" she asked, licking her lips as she tossed the condom in the wastebasket.
I told her yes, but I wanted to suck her cock first, so I grabbed a condom from the pile she had on the nightstand, and, copying her example, put it in my mouth, and rolled it down her cock with my wet lips.
"Very good, my little slut" she said, driving her hips slowly back and forth.
I was now lying on my side, with her kneeling over me, on her elbows and knees. My head was between her knees and elbows, on my side. She was fucking my face as if she were doing someone doggy style. I was motionless as her cock slid in and out of my stretched lips, and down my throat. I could see her balls swaying back and forth with her motion. I told her I wanted to taste her; I wanted her to cum in my mouth. She sat back on her heals, and told me for another $250, we could do the entire hour bareback. I quickly handed her the cash, and pulled the condom off her magnificent piece of meat. I engulfed it, making it a part of my mouth. I could feel the smooth, hot skin sliding up and down her shaft as she fucked my mouth. She used me like that for about ten minutes, finally telling me she was going to cum and asking if she should shoot right in my mouth, or pull out and jerk off on my face. I replied by moving my hands to her wonderful ass and pulling her deeper down my throat. I sucked for all I was worth, using one hand to gently squeeze her balls. I moved one finger to her tight rear hole and applied gentle pressure. I felt something wet on my finger, and realized she was squirting lubrication on it. I then slipped easily inside her warm ass and pressed against her prostate this time. She told me that was it, and grabbed the sides of my head, pulling out until just the head of her cock was in my mouth. She slid her hand up and down her cock. Her head was back and her mouth open emitting a lustful moan. I felt the first splash hit the roof of my mouth seconds later, to be quickly followed by three more. She started fucking my mouth again, driving in and out the full length of her meat. I pushed gently, and she backed off. I sat up and swallowed, looking at her as I did so.
"Your pretty hot, for a first timer". She then pushed me down on my back, took my cock in her hot mouth and sucked up and down several times. She then squatted over me, with her hands on my chest. She bent her thighs, and my cock penetrated her ass, with her still hard cock standing proud against her stomach. I switched my attention from my cock disappearing into her ass and her cock jutting up from her patch of pubic hair. I could feel the pressure build, and I guess she was able to see it on my face, because she raised herself off my cock and said "oh no, not yet, we still have time left.
"Roll over" she instructed, and once I was on my stomach, she pulled my hips up so I was on my elbows and knees. I then felt her tongue on my ass, and almost came as she stuck the tip into my rose bud.
"I'm going to fuck you baby" she said, "let me know if it hurts". I felt the cold lubricant hit my ass, then one, and then another finger find it's way inside me. She moved them around and in and out, loosening me up for her big cock. He fingers withdrew, to be replaced with her mushroom shaped head. I felt gentle pressure, and she told me to relax, then the pressure increased. He grabbed my hips for leverage, and kept pushing. I was trying to let myself stretch and admit her; I wanted to feel her inside me. Finally, my sphincter let loose, and the head popped inside. It felt like I was being torn apart. My rectum and anus were screaming in pain.
"You have to relax, let it stretch. It should only take about five or ten seconds."
I took deep breaths, and to my surprise, quickly stretched to accommodate her. She then started slowly plowing deeper and deeper. She would push in about two or three inches, stop for a few seconds, and then pull out. She would then push in a few more inches, and so on, until I felt her balls slapping my thighs. Once she was all the way inside me, she pressed herself to me, getting the last half-inch inside my stretched ass.
"You like that, don't you. You love cocks up your ass. I may be the first, but I won't be the last, will I?"
I had to admit, I loved it, the feel of her cock head as it moved inside my tight ass.
She began to saw in and out. Each time she pulled out, she pulled all the way out, so I had to stretch to take her again. After a few strokes, this was no longer an issue as my ass stayed open long enough for her to bury it inside me again. She fucked me for fifteen minutes, and then told me she was going to cum again. I scrambled off her cock, turned, and took her in my mouth, wanting to taste her again. This time, she drove her cock down my throat, pumping her juice directly into my stomach. As her final shudders rocked her, I pulled off, and gasped for breath. She lay back, panting, out of breath from her second orgasm. I put her legs over my shoulders, squirted some lube on my cock, and put it at the entrance to her hot rectum. I slowly pressed in, not sure how to do it.
"You have to push harder to get past my asshole baby," she instructed.
I moved closer to her, and pressed my hips forward, hard. I felt her ass give way and my cock entered her with a pop. I shouted. I had never felt anything like it. Her ass was tighter than any pussy I had ever fucked, and her rectum was hotter as well. I could not control myself. I was plowing in and out of her as fast as I could; driving my cock to the hilt each time I entered her. Faster and faster I moved, striving towards the orgasm I had to have. It only took about twenty strokes. I pulled out, and jerked off between her legs, shooting cum on her stomach and tits.
I lay back to catch my breath. Looking at the clock I saw we only had a few minutes left. I asked her if she would like to shower again before she left. She smiled, and said sure, that would be nice to not have to travel dirty. We took a nice, hot shower together, during which she got on her knees and first sucked me for five minutes or so, then soaped up my cock and gave me a long, slow, hot hand job that lasted fifteen minutes. We had gone over the hour, but she said not to worry about it, she could have gotten me off sooner if she wanted to. She went on to tell me she actually enjoyed watching my face in the shower as she slowly jerked me off. She kissed me goodbye, and left, walking out of my dream as she had entered it.
I have since found attractive shemale closer to home, and actually dated on for a year or so. I still love these beautiful creatures, and have been with men several times. I consider myself fully trisexual. I hope you enjoyed this actual piece of my past. For all you who are wondering, go for it. I guess going bareback was not all that wise, but I was caught up in my lust at the time. I have been tested and am fine. Be safe, and have fun.