I have an almost insatiable sexual appetite and am usually willing to have sex with someone after a few dates if I find them attractive and they treat me decently. However, I never suspected I might find myself in a situation where I would be having sex for money. That changed when I met a really sweet older man who just wanted someone to help him feel alive again.
I am a very passable shemale who loves to dress in revealing clothing and get a lot of attention from men. I have been told I am a very talented sexual partner, especially when it comes to oral sex. I love to suck cock and love to have my mouth full of hot, creamy cum. I like the feel of a thick, hard cock in my ass almost as much.
I spend a lot of time in the outdoors and regularly hike the various trails near my home. It was there I met the man who would make me his personal whore. His name was Sebastian.
I met Sebastian on one of the local hiking trails near my condo. I usually hike in very skimpy shorts, walking shoes, and skimpy tops because I like the attention I get. At the time I met Sebastian I was in my early twenties and everything was firm and toned. I am about five-foot-eleven and at the time I weighed about a hundred and fifty pounds. I have long tanned legs and a round firm ass, with very feminine curves and a “Demi Moore” voice. I used some mastectomy breast forms that give me a DD rack. I have very small dangly bits that tape very flat.
I had seen Sebastian several times on my various walks. I always said “hi” as I walked past him and he seemed pleasant. He seemed friendly and had an air of sophistication about him. I had noticed him checking out my ass several times and he would look at me admiringly but was never creepy. He never spoke to me directly until one day when we unexpectedly met where two trails came together. He introduced himself and asked if I would mind if he walked along with me. I told him I would like the company and we continued on together.
“I’ve seen you walking here a lot. Aren’t you afraid to walk by yourself?” he asked.
“I’ve never had a problem here,” I said. “There are always people around so I feel pretty safe.”
“I guess so,” he said. “My name’s Sebastian. What’s yours?”
“Gina,” I replied. “Nice to meet you.”
Sebastian and I made small talk as we walked. He went on to tell me he was a widower and had lost his wife about three years before. He was sixty three years old and lived alone in a house near the outer boundaries of the park where we were walking. Sebastian was an attractive man, slim but not skinny, and seemed to be in pretty good shape. As we walked he told me how pretty I was and commented on what great shape I was in. I thanked him for his compliments. As we walked, he asked me if I was dating anyone or was married. I told him I wasn’t in a relationship at the moment. As we continued to walk on the trail, he asked me if I would come to his house for coffee.
I hesitated for a moment, not sure if that was a good idea since I had really just met him and didn’t know him from Adam. For all I knew he could be a serial killer. I think he thought he had been a little too forward and began to apologize profusely. I assured him I wasn’t offended. I sensed he was lonely so I agreed to go with him.
We walked for a few more minutes and came to a beautiful house just outside the park. He invited me in and I immediately noticed the house was immaculate and there were photos of Sebastian and people I assumed were family members on the walls. I noticed one photo of a much younger Sebastian with a pretty woman he identified as his late wife.
We had coffee on his patio and chatted for awhile. We sat close together at a bistro table in his yard and at one point, he brushed my bare knee with his hand as he talked. I let it pass and he did it again, resting his hand on my knee for a second or two before moving it off. I could see he was interested in more than coffee. I smiled at him and said, “Sebastian, if you touch my leg again, I’m gonna think you like me.”
“I do like you, Gina,” he said. “I have been very lonely since my wife passed and have been starved for a woman’s company.”
For some reason, he looked so sad my heart went out to him. “How long has it been since you have been with a woman?” I asked.
“Since my wife died,” he said. “I just haven’t met anyone who really seemed interested in me except for a few old grandmas who want someone to support them while they play with their grandkids.”
He went on to tell me how lonely he has been and how infrequently he had visitors. He told me about his life and asked me about mine. I shared some things but I didn’t tell him I was a transexual. I didn’t want to embarrass him or make him mad when he realized he had made a pass at a shemale.
For reasons I can’t explain, I stood up and walked up next to him. I took his face in my hands and kissed him lightly on the lips. He stared at me with a surprised look on his face and I kissed him again, this time a little longer. This time he responded and his tongue slipped through my lips and met mine. We kissed for a few moments. His kisses were gentle and sensual.
I pulled back and took him by the hand. Right then I decided I would reach out to him and make him feel important and ease his tension.
I led him back into the house and to the sofa in the living room, where I told him to sit down. He complied. I decided to deviate from my usual parameters for sex and had decided to do something that was unusual even for a cum guzzling slut like me. I was going to sexually pleasure this total stranger if he let me.
I kneeled in front of him and looked into his eyes. He held a steady gaze as I gently separated his legs. He moaned softly as I undid his pants and released his penis from the front of his pants. I noticed that in spite of his age, his cock was firm and substantial. I looked into his eyes as I took his cock into my mouth, slowly rolling my tongue around the head and licking the shaft while I stroked him slowly. I drooled saliva on his throbbing dick and began to suck him off deeply and slowly. He moaned softly as I sucked him off, taking more and more of his cock down my throat until my nose pressed against his abdomen. He gently ran his fingers through my long hair and pressed my head down on his cock. He softly moaned my name as I sucked away.
I sucked his cock like a street whore hungry for cum for about ten minutes, alternately taking him deep then teasing him with my tongue and teeth. I could taste his pre-cum and noticed he was starting to tense up as if to cum. Before he did, he whispered, “I want to make love to you Gina.”
“You may not want to if you knew the truth about me,” I said.
“You don’t have to say anything,” he said. “I know you are not what you appear. You were not born a woman.”
I was floored. At the time, I looked and sounded like a very sexy genetic woman. I was totally surprised he could tell I was a guy.
“How did you know?” I said.
“Your hands,” he said. “A real woman’s index and ring fingers are usually the same length. Yours are not. Otherwise, I might have been fooled. It doesn’t matter to me, Gina. It would not be the first time I have been with a pretty man dressed like a woman.”
I was completely unaware of this detail. “Sebastian, I don’t usually have sexual relations with someone I just met. I really feel you are sincere when you said you are starving for female company. Today I am willing to do whatever you want to please you, as long as you don’t try to hurt me.”
“I would never do that, beautiful Gina,” he said. He walked out of the room for a minute and returned with a bottle of lotion. He set the lotion down and took me into his arms and began kissing me on the lips and my neck, running his hands up and down my back and over my ass, squeezing my buttocks hard. Our tongues melted together when we kissed. He put his hand under my shorts and ran his fingers down my ass crack then began rubbing my dick. I slowly pulled down my shorts and I removed the tape holding down my little dick and balls. He moved down to my cock and kneeled in front of me, slowly licking the pre-cum off the tip of my dick before taking it into his mouth and sucking it slowly. He did this for several minutes and I was shaking when he stopped.
He lubed his cock and my ass with the lotion, fingering my asshole as he did so. After he fingered my ass for a few minutes and licked up and down my spine, he had me kneel on the sofa facing away from him. He moved behind me, placing one of his hands on my hip and grabbing my hair with the other hand, pulling my head back gently. I felt the tip of his cock against my asshole as he pressed his cockhead against my tight man pussy, His hard cock suddenly popped inside me. There was no pain and I easily took him in. It felt so good to feel each inch slide inside me. He slowly buried his cock inside me until I felt his balls slap against my thighs.
I hadn’t planned on being fucked in the ass that day and had not prepared. I guess I just happened to be clean because he began fucking me enthusiastically, grabbing me by the hip and pulling my hair at the same time. There was no indication of smell or leakage other than lotion oozing down my ass crack and balls. He pistoned his cock into me for some time as I felt my own orgasm starting to build.
Sebastian suddenly moaned louder and his body shuddered. I knew he had shot his load of cum inside my ass. He pulled me against him and buried his cock deep inside me as he came. I was stroking my cock while he fucked me and my orgasm let go. It felt so good to have his cock inside me while I shot my load onto the hardwood floor. Sebastian still gripped my hips while he buried his cock in me. He stayed inside me for several minutes before pulling out.
I went into the bathroom to clean up and when I returned, he was dressed and kneeling by the couch, cleaning up my man juice from the floor.
Sebastian walked up to me and extended his hand. I saw he was holding a wad of twenty dollar bills. He started handing them to me and I stopped him and said, “Sebastian, I’m no pro. I just wanted to make you happy today. You don’t have to pay me anything.”
“Please Gina, I know you were just being kind, and probably wouldn’t do this again on your own,” he said. “I was hoping we could do this again. In fact, it would be worth it to me to pay you not to be with anyone else, and just visit me once or twice a week. Just tell me what it would take for you to be my girl until I can’t get it up anymore.”
I told Sebastian I would think about it. I really enjoyed having sex with Sebastian but had never thought about selling myself. After thinking about it, the thought of being his sex slave kind of turned me on. I decided I was willing to be his exclusive sex toy if he was willing to pay.
I met him a few days later on the trail and we walked together. I told him if he would give me $100 for a blowjob, or $200 for a blowjob and a fuck, I would be willing to be his concubine. He readily agreed and we began an almost three-year relationship of regular sexual rendezvous. We experimented with many different kinds of sexual activities, including bondage and role playing. He especially liked it when he tied me up and he made me beg him to fuck me or let me suck his cock so he would release me. He loved to cum all over my face and in my mouth as I swallowed his cream all down then licked him clean. Although he would sometimes be domineering when I was being his sex slave, he was always sweet afterward and always paid in cash after our visits. He would sometimes pay me much more for my services than we had agreed on.
Unfortunately, he wasn’t able to keep things going and eventually we stopped meeting. He passed away about five years after we met. I can only hope I made his final years more enjoyable.
A few years later I again found myself fucking my boss and his friends for money but that didn’t last very long. I found that I liked being lusted after and used as a sex toy by otherwise straight-laced men with kinky fantasies. As long as the clients didn’t get too carried away and get violent, I was happy to bring their fantasies to life.