tagTransgender & CrossdressersCase of the Jealous Transsexual Ch. 01

Case of the Jealous Transsexual Ch. 01


I met her on a free amateur’s web site. I have to admit that I was not particularly looking for a transsexual at the time. I had posted some naked pictures of myself on the site and had been going through the tons of emails that I had gotten in response when I ran across Dee as she called herself. She had sent me a picture and a simple email stating that she lived in the area. The picture didn’t show her face, nor did it show her penis. It was a picture of her bent of, her ass facing me. A nice ass, thick, even toned.

I had contacted her through the AOL messenger service and we learned a little of each other for about a week before moving to the phone. She had the sexiest voice ever. There was no indication whatsoever of her being a transsexual. She had described herself as standing 5’6, 160, plump, thick, nice pussy, 36 b cup breast with big dark nipples. Dark chocolate complexion, medium length hair, full soft lips, and sexy eyes. I must admit after meeting her, the description was pretty close to the truth.

We had never really made any plans on meeting. It happened on the spur of the moment. We were on the phone and I asked her in a flirting manner if I could possibly stop by her place and finally meet her. She, to my surprise agreed. I remember her asking how long it would take me to get there. I still had to shower and dress. It was late, about 11 but I had worked out earlier that evening and had yet to freshen up. Well I told her it would take me about 30 minutes to get ready and 15 minutes to get to her place, and that I would call her on my way out of the door. I had skipped on the shower getting dressed, and called her. She picked up the phone, she said she was about to get in the shower. I told her not to, that I’d like her to wait until I got there so we could shower together. She giggled and said yeah that it was a great idea. Then all over a sudden she took on a different tone.

It really upset me when she said that she changed her mind, saying that she was not the type of female I was looking for. I really didn’t know what the hell she was talking about so I asked her “what kind of female are you then?”. That’s when she told me that she was a transsexual. She proceeded to explain that a transsexual is a man that feels that he is or changes himself into a woman, or vice versa. She added that she was a pre opt transsexual, meaning that she still had a penis that was fully functional, that her breast were real, she has not has any surgery of any kind, just hormone treatment which is why her voice was so feminine. After telling me the truth, she was happy to hear that I did not mind at all, that I had been with transsexuals in the past, and that they turned me on, and yes I still wanted to meet her. I took a cab to her place. I didn’t want to drive because she mentioned that she had drinks at the place and I didn’t want the burden of driving home drunk, in case I didn’t spend the night there, which I did not.

I arrived at her apartment with some Chinese food; she mentioned on the phone that she was hungry. Her studio apartment was very cozy. She had really set the mood for a sensual evening. The place was dimly lit with candles all over. The temperature was perfect. She had a straight porno tape showing on a large screen television. A black couple was going at it strong.

She complimented me on my looks even though she had seen a picture of me already via email; she said I looked even better in person. She took my coat and invited me to sit down on her couch. I sat and she brought me a shot of Hennessy and a bottle of Heineken. She also fixed me a plate of the food I had brought over. We made small talk while eating. The food was good and it gave us time to get a little bit more comfortable. She had decided on showering before I had gotten there, but I was still sweaty from my earlier workout. I told her that I still needed to shower and she said it was fine; she would get me some towels.

As she got up to put away the dirty dishes she knelt in front of me and began to undo my pants, she pulled down my zipper and undid my belt. I raised my ass a little so that she could slide my pants and boxers down. She took the hint and my pants were down to my ankles before I knew it, and my semi hard dick was in her mouth. She was showing me why her AOL screen name was “blkoraldr” or something like that. I’m not quite sure. Well anyhow my dick grew in her mouth to its full 8 ½ inches. She slurped as she sucked like a vacuum. She rubbed my inner thigh and followed with long lick from my thighs to my balls, all this as she stroked my dick. She sucked each of my balls, gently, one by one, and licked the area right before my ass hole. Her mouth was so warm. She kept this up for about 20 minutes.

During this time she would not let me use my hands to do anything.

I tried touching her, caressing her face, grabbing her head, reaching for her breast, but she stopped ever attempt and asked me to just sit there and enjoy myself. It didn’t take me long to accept her request, especially the way she sucked on the tip and licked the hole so gently. She expertly stopped me from coming about 5 times, each time switching up the stroke so as to raise the great sensation I would feel from this orgasm. By this time I she had taken my shirt of as well and played with my nipples with her hands and tongue. She gave me sweet kisses and licks on my neck and ears. She licked my eyebrows, and kissed my eyelids and she kept a stroke on my penis with her hands. She licked down my chest back down to my balls and up my shaft. “Look at me” she said. When I looked down I could see the whites of her eyes looking up at me as she sucked on my dick ferociously. Up and down, in and out of her mouth. I knew this time she would not stop me from unloading in her mouth. She felt me tighten up and began to rub my asshole with a wet finger.

I could feel the cum making its way up my shaft and so did she. She kept with the same even paced mouth stroke. Just as she heard me moan out loud that I was coming she stuck her index finger half way up my ass hole, and braced herself for my load. It shot straight to the back of her throat. I know because it made her gag for a half second. She somehow made the adjustment and was able to swallow every last drop. It was the first time my orgasm had gotten to that level of intensity. I was shaking like when a woman does when she has a great orgasm. Dee-Dee kept sucking me dry as I calmed down. When she was done she took a swig of beer and told me to go ahead and shower. I was so relaxed in the shower. The water was a perfect 80 degrees; she even had the very same brand of soap that I use. I took about 15 minutes in the shower.

When I came out she invited me lay down in her bed, and she herself went in the bathroom for a few moments. Dee-Dee joined me in the bed. She was naked as I was. Before she lay down with me I told her to stand so I could get a look at her body. She had not missed a beat in her description, except for the 5 inch penis sticking out at me, inviting me to take it in my mouth and reciprocate what had been done to me so well. I grabbed Dee-Dee by her penis and pulled her towards me in the bed. She lay down and we started kissing. Her lips were so soft. This time I whispered for her to just lay there as I took my time exploring her body.

Her skin was so soft and sweet. I kissed her all over; I sucked on her nice breast. She moaned every time I went near them so I always made sure that they were being stimulated at all times. When I finally got to her fully hard dick I took it all in my mouth. I had deep throated a dick at least as big as mine on more than one occasion so 5 inches was nothing. As I sucked her she moaned even louder and I felt her hand squeezing tightly on top of my hand, the one holding on to her breast. I sucked her just enough to get her really hot, even though she was as hot as she could ever get by this time. I licked down to her balls and pushed her legs up to get at her asshole to eat her out. I licked her sweet ass hole until I felt it was good and ready for my hard pole. I put on a condom and Dee-Dee surprised me once again. She told me she wanted to start out on top. She had a bottle of this great lubrication. She lubed herself and poured a little bit on me also. I lay on my back as she straddled herself on to my dick. She took her time sliding all 8 and ½ inches into her deep ass hole. When it was all the way in she increased the speed of the stroke. I grabbed on to her hips and guided her as she rode me. She would lean back and massage my balls as I squeezed on her tits. I was in heaven, Dee-Dee felt so good. This was definitely the best piece of ass I had ever gotten.

Although I enjoyed the way she was riding me, it was time for me to take control of the situation. I told Dee-Dee to get up so that I could fuck her doggy style. She obliged by getting on all fours at the edge of the bed. I stood, feet on the floor, behind her and entered her once again. I had told her to arch her back and put her face to the pillow. I grabbed her hips as I guided myself into her tight ass hole. Once fully in, I started my long stroke motion. At a even pace I fucked Dee-Dee with long strokes, in and out, in and out as she moaned and begged for. As I got more and more into it, my pace increased. Within 10 minutes I was banging the hell out of her. I know that the next door neighbors had to be listening to us by this time. It would not have been hard, Dee-Dee was yelling to the top of her lungs. Fuck me, Fuck me!! Oh yes Daddy fuck me!!

I wanted to see her facial expression as I fucked the life out of her so I made her turn around on her back. I pushed her legs back, as far as I could and entered her once more. This time I really got into her the way I wanted to. She tried pushing me back, but I persisted and she just gave in. I could see the tears coming from her eyes, and the lost look of extreme ecstasy on her face. As I continued to fuck her a shot of cum came streaming out of her penis. This was without any direct stimulation of any kind. She just came and it landed all over her nice tits, and some got on her lips, which she licked and swallowed. The rest she ate off of my fingers like some Halloween candy. Dee-Dee was the best. I wanted so much to cum in her that I took the condom off right before I was going to cum and unloaded my second one deep in her rectum. She held me as tight as she could, feeling my dick pulsating in her ass. As I pulled out she tightened so as to squeeze out any remaining cum.

I know you’re wondering where the jealousy comes in… Well I first had to tell you how Dee-Dee and I met. Next I will let you in on our 3rd encounter. See the second was pretty much the same. But the third time I saw Dee-Dee she invited me over to meet her cousin from Florida, Alexis. She told me Alexis wanted to have a 3-some but it didn’t quite turn out that way… And so the jealousy took over. Stay tuned for part 2.

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