Being a bisexual male I enjoyed sex with both men and women. I had a natural submissive streak so whenever I was with either a male or a female, or sometimes both, as had been the case once in the past, I liked to be instructed on what to do, whether that was giving or receiving. Over the past two years I had favored male company, and while I hadn't settled down, I had a number of relationships, short though they were, as I wasn't ready to settle down with either sex. I wanted to play the field and do as much exploring and experimenting as possible before doing the whole commitment thing. 

With my last boyfriend, I was very open about my submissive side and my bisexual side. Straight away I told him that I was bisexual and enjoyed sex with both males and females and that I was unlikely to want to commit to anything long term with him while I was in what I dubbed my 'free period' of experimenting and trying new things. Jack, being a gay male, was very open in return with me and very understanding, which I appreciated, but things broke down after four short months. He wanted more commitment than I was willing to give. He wanted more from me, while I was happy with the casual sexual relationship we had. I couldn't help but think that the breakdown in communication in our relationship and the widening gap between us had something to do with a fantasy I had disclosed to Jack one night. He was asking me questions about my experimentation period and I was answering very truthfully, telling him about my desire for both men and women. 

I told him about a fantasy I'd had ever since the age of twenty or so when I first started exploring my bisexuality. The fantasy involved a transsexual woman, and her pounding my ass and doing all sorts of crazy wild things to me. Jack didn't take too well to my disclosure of such a fantasy and it was after that, that we started arguing more and a very obvious gap came between us. We broke up easily enough, both of us deciding that there was no love lost. I started frequenting gay bars often after that, usually going home with someone or at least receiving and giving a quick a suck and fondle in the bathrooms.

But my sojourns to gay bars and clubs was put to an end temporarily when I was sent travelling for my job. I would be away for a month, travelling to four different locations and staying in each location for just under a week at a time. It was fine for the first two weeks while I was in New York first and then Baltimore. I was kept busy and so didn't have enough time to go and check out the club scene with both men and women. Heck, I barely even had time to masturbate. Not even on the weekends when my company had very kindly told me I could 'take a break' from work and travel.

On my third week of yet more business meetings and conferences in another city, I was exhausted. I was absolutely tired, despite the four total days I had been given off so far, which were spent in airports. Not much of a break. I decided that evening, after going back to the Hotel I had been kindly put up in by the company, that the next day I would do as little work as possible. I would make up some bullshit excuse to get me out of the meetings and postpone them for a day or so, maybe even half a day. I just wanted proper sleep and time to relax. I was also incredibly horny. It was quite a shock to my system to go from my prior sex-fueled, club crawling lifestyle, to be sitting in board rooms and conference rooms all day until late in the evening, and then getting in, being so tired that I couldn't even jack off. 

I set an alarm for early the next morning and rang up the people in charge of the meetings and conferences while I was in Orlando. I made up some crappy excuses, pulled some strings and got the day off. As soon as that phone call was over, I turned my cell phone off, rolled over and went back to sleep for another few hours, not rising from bed until nearly ten am. I had a leisurely shower and wash and then headed downstairs for brunch, where I perused the local paper. 

I was still incredibly horny at this stage, the previous night's quick masturbation session not alleviating my horny, sexual desires. I looked over the classifieds, wondering what the paid sex scene was like in Orlando. I had no problem with using call girls and prostitutes. I had only done it twice before in the past, but I had enjoyed the experience. I didn't see any issue with it, after all, that was their job. They were paid to have sex with horny guys such as myself. 

One ad, in particular, caught my eye after I read and then dismissed the other girls. I asked one of the servers for a pen and paper and quickly scribbled down the details of the ad for this girl. I dashed back up to my room and rang the number I had written. 

"Hi honey," came the voice of the girl on the other end. Initially, I asked her to have dinner with me that night at the Hotel, as I wanted decent companionship and conversation as well as sex. 

"What time can you be here?" I asked her. 

"I can be there by eight," she said. 

"Excellent, see you then," I beamed. For the rest of the day, I lazed around my Hotel room, watching old Westerns on TV, heading down to the pool and steam room for a quick dip and doing a spot of shopping and sightseeing in Orlando, as I had not had a chance to do this in New York or Baltimore. At six thirty I headed back to my room to start getting ready for my dinner date with the call girl. I was a bag of nerves while I was getting ready. True I had used the services of escorts and call girls before, but this seemed different. This seemed to be a new experience for me. A first. 

I found myself so excited and jittery that I headed downstairs to the restaurant a full half-hour early. I sat at the bar and ordered a scotch to try and calm my nerves before she arrived. I didn't know what she looked like, apart from a few details she had given me over the phone. I knew she would be wearing a red evening dress, a rope of pearls around her neck, and that she had long black hair. She also told me that she was tall. At the time I thought I could remember all that, but sitting here at the bar waiting for her, I decided that she hadn't given me enough details about herself. That could be anyone! I thought with alarm. 

It turns out I didn't need to be worried. I saw her approach the bar looking exactly as she had described, yet better. Her long black hair was glossy and shiny and her skin was a warm tan color. Her red evening dress clung to her body and breasts, the pearls around her neck accentuating her perfect looking tits. 

"V-Veronica?" I asked shakily, trying to gain composure in front of this beautiful woman. 

"You must be Jim?" she asked. "Pleasure to meet you." 

We exchanged pleasantries for a few short moments and then I escorted her to the table where we dined and made witty intelligent conversation. It was nice to talk to someone about something other than sales conferences and business meetings. Here was a woman who could hold a decent conversation, paid attention to the news, both local and international and knew what she was talking about when it came to not only her job but sales, as she knew a little bit about what I did. She was happy to answer my questions about her job as a paid sex worker, she was very open with me about the process and how she came to be a call-girl. 

We stayed and talked for hours, the conversation just kept flowing between us. When I looked at my watch after we had finished the final cheese and fruit course, I saw that it was nearing midnight.

I had stayed for dinner with Veronica longer than I would have liked, but I did not mind. It was more than fine by me. I paid for the dinner and then took her back to my room, my cock throbbing with excitement at the night, or more accurately, the early morning ahead of us. 

I showed Veronica to my room and offered her a seat on the small sofa and asked if she would like a drink. She declined the offer and I decided that I did not need any more alcohol in me, for fear of it interfering with my performance. I went and sat down next to Veronica and breathed in the scent of her perfume, which was a warm, slightly spiced smell. It was very sexy and exotic and just added to her overall 'dark' look and persona. She definitely suited her perfume. 

Breathing in and out deeply to steady myself, I placed my hand on her thigh and looked deep into her eyes. I leaned in and kissed her, a soft little kiss. When I saw that she was smiling at me, I leaned in and kissed her once more, but this time with more heat and passion, as my cock started to wake up and harden in my suit pants. I slid my own hand up Veronica's thigh and gently brushed it over her crotch. I knew what was there, underneath her dress, that was part of the reason I had picked Veronica over the ad's of the other girls in the newspaper, but it still surprised me a little and it took some getting used to. Veronica was so sexy and womanly that I had forgotten about it throughout the evening, only remembering about it now when I felt her own cock harden under my soft grip as we kissed. 

Seeming to know exactly what I wanted, Veronica started to unzip my pants and released my cock, gripping it and moving her hand up and down the shaft. With her other hand she cupped my balls and then, breaking away from the kiss, she got down on her knees and took my erect cock in her mouth. It had been a while since I'd last had a blowjob, so I was in heaven, sitting on the sofa in my Hotel room while the beautiful Veronica sucked me off like an expert. She rolled her tongue around the head, and then had it flat against the underside of my cock as she took me deeper into her mouth, very slowly. I threw my head back and moaned loudly, running my fingers through her gorgeous black hair and holding her head as she bobbed it back and forth. 

"You're gonna make me cum if you don't stop," I warned her. Deciding that the blowjob was over, Veronica stood up and smiled at me, unzipping her dress from the back and letting it fall to the floor, revealing her incredible body. Her breasts were obviously fake, but they were high and perky, two full rounds that would fit my palms perfectly. As she took off her bra, her breasts bounced with the motion and my cock twitched visibly. I couldn't wait to grab them, or perhaps feel them on my cock. I then looked further down her body and saw that she was not wearing panties. Her cock jutted out proudly, erect and ready. 

Standing up quickly and undressing myself the rest of the way, I went over to Veronica, kissed her deeply and then got on my knees, staring directly at her cock, which was circumcised and a healthy seven and a half inches and rather thick. I kissed the tip of it, some of the pre-cum leaking out and coating my lips as I engulfed the head and sucked on it. It had been a while since I had last sucked cock, and I vowed then and there that I would do it more often, as I was rather enjoying being down on my knees and servicing a gorgeous trans call-girl. 

I held her cock at the base and ran my tongue up and down her length, tracing the veins and then returning to the head, where I sucked it once more, taking it deeper into my mouth. I could only take it so far before I gagged, but I kind of enjoyed the sensation of gagging on a cock, and Veronica seemed to enjoy the experience also, moaning loudly and rocking her hips. 

"You like my cock don't you?" she asked in a husky, sexy voice. 

"I do," I answered, taking a break from sucking to speak to her. 

"Get up on the bed, on all fours," she said in a voice that was soft and feminine but had a commanding tone to it. I stood up and went over to the bed, sliding into the centre and positioning myself on all fours, as instructed. I felt Veronica behind me, running her finger up and down my ass crack before gently probing at my hole. I expected her to slip a finger fully into my asshole, but instead I was surprised with the sensation of a warm tongue tickling my hole, and then probing at it. 

"Oh God," I muttered when I felt her tongue darting back and forth over the hole and then pressing at it, trying to gain entry. When I felt her tongue get past the ring of muscle I cried out in pure joy. It was an incredible feeling having a tongue at my asshole, licking and probing with it. The warmth from her tongue was briefly gone as she took her face away from my ass and started using her fingers once more. 

"You like my tongue on your ass?" she asked. 

"Fuck yes I do," I mumbled as I felt a finger slip inside me, gently moving back and forth. 

"I think you're nearly ready," she said. I could hear the grin in her voice as she added a second finger and pushed into me with them, preparing me for what was soon to happen. She pulled her fingers from my ass and her tongue very briefly returned, lubricating it further. I then felt her run the tip of her cock up and down my crack, smearing some of the pre-cum around. One hand on my hip and the other I imagine holding her cock, I felt it gently pressing at my ass. 

It was a slow process but my ass was used to taking cocks, so the head slipped in after a while. With the head past the ring of muscle, Veronica was free to take gentle thrusts and push her thick cock further into my ass. It hurt a little at first, not having sufficient lubricant around, but the pain soon faded until all I could feel was the pleasure of having my asshole stretched by Veronica's thick, hard cock. She managed to find a rhythm, thrusting firmly into my ass, her hips starting to bang against mine. 

"You've got a tight ass," I heard her say from behind me. Placing both her hands on my hips, she drove her cock the rest of the way inside me and we both moaned loudly. As she fucked me from behind, I grabbed my cock and started jacking myself off, loving the dual stimulation I was receiving from Veronica and my hand. My fantasy was coming true. I was being fucked by a gorgeous trans woman with a thick cock, and I was loving it. But it was all getting too much for me. I felt my orgasm building up, my balls tightening as the cum was forced out. 

"I'm going to cum!" I told her, feeling the warmth overwhelm my body. The tingle was starting from my cock and radiating out. "Cumming," I groaned as the first drops of pearly white cum dotted the quilt below. Veronica kept fucking me, her moans getting louder as I came. I wanted more than anything to feel her cum in my ass, so I started asking for it. "Please cum in my ass. Please," I said. 

"Oh fuck," Veronica moaned. "Where do you want my cum?"

"In my ass," I told her. 

"I'm gonna cum in your ass," she replied. 

"Oh fuck yes," I said as I felt the first powerful jet hit my insides. I stayed hard as she came inside me, thoroughly coating me. It wasn't until she pulled her cock from my ass that we both started to soften. I lay down next to Veronica and kissed her deeply. "I hope you'll be ready for round two," I told her. "Because I'll be fucking you."