Michele Nylons' Stories Ch. 01

My cock had deflated and was semi-hard now even though I was excited to the extreme. She remedied that by taking my penis into her mouth; she gobbled it all the way in and gave it a concentrated tongue lashing as she sucked on it. My erection came back very quickly but Tanya had no problem keeping all of me in her mouth as she sucked me right down to the base of my member.

I bent my head and went back to sucking Tanya's hard penis. I gave my complete attention to fellating her and eventually I was able to get about half of her comfortably into my mouth without choking. I built up a steady rhythm and started to really like what I was doing; enjoying the experience of the fullness of her in my mouth and the taste and texture of her hard cock. I was feeling quite happy with myself, knowing that what I was doing was giving her pleasure. Then she said the words that both enthused and terrified me, "Would you like me to fuck you?" she asked. It took me about millisecond to respond, "Yes please."

I had earlier explained to Tanya that I was a virgin but that I had fucked myself with vibrators and dildos on many occasions and she explained to me that getting fucked by a cock was totally different, especially the first time. Tanya eased herself from under me and positioned me on my knees with my head down on the pillows and my arse high in the air. If she told me to relax once she told me a thousand times over the minutes that followed. Tanya lifted my negligee out of the way and pushed my panties to one side exposing my arse to her. She ripped open my pantyhose even further and I felt the cool air on my exposed buttocks.

Tanya reached over, took a large tube of lubricant off the bedside table and thoroughly lubricated the area around my arse bud. She massaged away gently and then I felt her start to slide a finger inside me and it was felt like heaven. She reached under me with her free hand and slowly squeezed and stroked my cock as she slowly worked her finger in and out of me, working it slowly deeper inside me. She complimented me on our progress so far and again reminded me to relax as she extricated her finger and I heard her unwrap a condom and fiddle about a bit behind me. I looked around in trepidation at what may be coming next and saw that she had slid the condom onto a medium sized dildo and was busy smearing lubricant all over it.

I put my head down again and tried to relax as I felt the hard plastic instrument against my rear entrance. I have to tell you that try as I might, I could not get relaxed enough for the implement to slide in easy. The tip slid in easy enough but as the wider girth of the dildo began to pass through my sphincter the pain started to mount. It was not a sharp pain, more like a stretching, burning pain. Tanya was as gentle as she could be and took her time and on several occasions asked me if I wanted her to stop. I refused to give in though; I wanted to be fucked tonight! Eventually after several winces and muffled groans the dildo was most of the way inside me. Tanya had had to remove it a few times and apply more lubricant until I would let her continue but once it was in me and she started to ease it back and forth I was able to relax sufficiently enough to start to enjoy the experience.

Tanya fucked me for several minutes with the dildo, gently milking my semi-erect cock as she did so. I never did get fully hard (and seldom do even now when being fucked) but it still felt wonderful. What I was experiencing now was similar to what I experience when I fuck myself; all of the other sensations become amplified. The feel of the nylons on my legs, my panties scrunched up around my arse, and the negligee rubbing its silkiness on my body. I also love taste of my makeup in these situations; the taste of my lipstick in particular; enhanced by the feel of my hair on my face, I feel very feminine and submissive. This time though, someone else was administering the dildo, and that made the experience even more intense. Then she asked me the fateful question, "Are you ready?" I knew what she meant and of course I answered "Yes!"

The dildo slid out of me very easily and then there was again the awkward experience of kneeling there with my arse in the air and my head down on the bed whilst Tanya fumbled with another condom wrapper and applied yet more lubricant to my sphincter. (A position that I am now quite familiar with!) Then I felt the bed stir and heard it squeak as Tanya positioned herself behind me and between my legs. She pushed my feet further apart so that she could get right in close and I felt her position herself close against my upraised arse and finally felt her member against my sphincter. For about the hundredth time she told me to relax and then she slowly pushed forward. I screamed in pain.

"Take it out! Take it out!" I moaned. Tanya slid the miniscule amount of penis that she had forced inside me out and apologised for the pain she had caused me. She was so considerate and asked me if I wanted to stop what we were doing but I was resolved to my purpose. I would like to report that the next few minutes were painless and that once she was fully inside me I was overcome with pleasure but I'm afraid the truth is that the next few minutes were very painful. (Unlike in most of my stories where once Michele has been entered; even against her will, she immediately starts to receive pleasure.)

After several attempts and half a tube of lubricant Tanya eventually had the head of her cock and some shaft inside me. We rested like that and I was able to relax my interior muscles and enjoy the fullness or Tanya's cock inside of me. When she sensed that all was ok Tanya commenced to slowly fuck me; easing more and more of herself into me with each thrust. Now I really started to feel pleasure; the fullness of her member was particularly nice and even covered in the latex sheath of the condom, the feel of a real penis was so different to the rubber substitutes with which I had pleasured myself on numerous occasions previously.

The most intense pleasure was coming from where my sphincter was stretched around her pole and where the head of her cock rubbed against my postrate; but I was also receiving stimulation from all along the walls of my back passage. I now started to rock back and forth in time with Tanya's thrusts and was wrapped up in the bliss of actually being fucked for the first time. Again all the senses of my body became more acute and I was so aware of my lingerie, makeup, shoes and wig; the sensuousness of my pantyhose and panties were particularly heightened when Tanya thrust against me and her body made contact with my legs and buttocks. I licked my lips and tasted my lippy and swung my head slowly from side to side feel the soft caress of my long blonde hair on my face, neck and shoulders.

After about ten minutes of slow, solid fucking I was close to orgasm and Tanya had settled into a steady rhythm which was gradually increasing in tempo. Occasionally a thrust would be mistimed and cause me slight discomfort but mostly I was experiencing a wonderful ride. Tanya then stopped and asked me if I would like to experience being fucked whilst I was on my back and I eagerly agreed to the proposal. She remained in control but was so thoughtful; how lucky I was to experience my first Transvestite sexual experience with such a caring person.

Tanya eased me onto my back and placed several pillows under me so that my groin was lifted up and positioned nicely for her to regain entry to me. It took a little while for me to relax again and her entry was slow but far less painful than before. We had soon regained our rhythm and now I was really getting aroused. Tanya lifted my legs right up high and spread them wide, but once she was comfortably deep inside me she lowered them and pushed my calves back so that my heels were near my shoulders, my legs wide, and her body leaning over mine.

Now she could lean forward and kiss me as she fucked me and I also loved the feel of her hands pressing on the backs of my nyloned thighs as she pushed my thighs down. She asked me if I was close to coming because she was close herself. Then she said something that I agree with and disagree with at the same time; she said, "Orgasm during anal sex is mostly mental you know." I agree that the brain is the biggest sex organ in the body, but I have to tell you I love the feeling of being fucked. She also asked if it was ok for her to come inside me; again being considerate. I indicated my acceptance and she began to fuck me earnestly.

I could sense her orgasm approaching as she thrust into me faster and deeper and I did my best, restricted by the position I was in, to fuck her back and meet her thrusts. Then the most earth shattering orgasm I had ever experienced shook my body. I could feel her cock throbbing inside me and her thrusting cock sent wave after wave of pleasure through my whole back passage and particularly my sphincter from which I felt the most intense pleasure. My cock, which had remained flaccid throughout most of the fucking, suddenly became semi-erect and shot stream after stream of hot semen onto my belly. Tanya squealed with joy and thrust hard into me, and although I couldn't feel the jets of her ejaculation through the condom, I could feel her cock pulsate inside me. She was panting and mewing and along with the extraordinary pleasure I was receiving from my own I orgasm; I also a real sense of accomplishment because I had made this Transsexual prostitute come. After we had both come down from our respective orgasmic highs, Tanya eased herself out of me and I was delighted to glimpse the tip of the condom hanging from her now shrinking hard-on was filled with creamy sperm; she wasn't faking it at all!

Tanya helped me undress and remove my makeup and allowed me to shower. We shared a drink and a cigarette whilst I slowly dressed and we discussed how the evening had gone. She gave me a few more makeup tips and then it was time to leave. I thanked her profusely for leading me through my first sexual encounter as Michele and she said she did enjoy it, even though it was 'work'. I left her apartment and went back to my hotel where I re-lived the event in my mind and masturbated before I fell asleep utterly content.

Epilogue

I swear to you good readers that the above account is true (as best as I recollect it anyway). I have been with other Transsexuals since, but it has never as good as it was in Sydney with Tanya. I have enjoyed the encounters, but the girls have always been unable to gain or maintain an erection; and lets face it girls, us Trannies love a big hard cock!

I thought my musings would be able to be kept to one single article; but as usual I have babbled on and this essay is already ten A4 pages long. I will publish part two a little later and include my experiences with a genetic female (GG), my first experience with another Transvestite, a couple of experiences with male Admirers and one of my group sex encounters. If my reading audience is not happy with this form writing though, please provide me with feedback and I will cease and desist.

Most of you have been positive about my story 'Michele and The Predator' and my intention is to complete that story before I continue with this essay.

To all of you who have provided feedback to me; I thank you all. Feel free to email me and I might even send you a picture or two of me at play! Once again thank you all for reading my stories.

XXX

Michele

To Be Continued......................