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The next Saturday I was still in the mood. For most of the week I argued with my woman and that day I got a little drunk (not too much actually). It had been a while since I'd started living the night owl's life without her knowledge and I did the same again that night. I got into my car and began to wander aimlessly through the streets of the city, a little to pass the effects of alcohol, a little to calm down and a little (mostly) to run into a particular adventure. I must say that in those years I had several adventures with women and not only with men (to tell the truth, only one) and transsexuals; adventures that were not wanted and not paid for. I hoped to be lucky that evening, but it was not so, it was raining and there were not many people around, it was also quite late. I passed by piazzale Lodi and there I saw some transsexuals (they had their tits almost out, under the umbrella) who were beating, so I went around the square a couple of times to look at them better until I stopped near one of them; I asked him if he wanted to go for a ride with me, of course he laughed at me saying that without money you can't sing masses. I went away but a little later I came back, by now I was determined and I wanted to do it (so I thought) and I told him that I had only 20,000; nothing doing, he didn't move from there. After a few more rounds of the square I stopped again and showed him the only 35,000 I had in my wallet; a little annoyed, a little because in all that time no one else stopped besides me, he accepted. Before then I had never paid anyone for sex and in a short time that was the third time I had contracted (although I had a woman at home who was sleeping). My car didn't fit him (or maybe he was cold, who knows) and he decided to take me to his place. He got into his car and took me to Viale Ortles, where he had a small room; he told me that he was from Puglia and that he shared the bed and the room with another transsexual. She had come to Milan to make her fortune and in a few years she found herself with an extra pair of tits and a broken ass. He told me he liked me and began to touch me and slowly undressed me; in the meantime he began to kiss me in the mouth and then on the chest while he took my limp cock in his hand to make it hard, he went down further and further, up to him and with his mouth he put a condom on me and began to suck it with tight lips. The usual alcohol fumes or who knows what else was not getting me hard enough for decent penetration. After several attempts he gave up; then we started kissing again in a different way and this time I took his cock in my mouth, he/she had a hard on, but he/she didn't want to do it without a condom. It was strange to suck a cock with a condom, that taste that was not of a cock but of slimy rubber (or cellulose, I don't know). He had a cock that I didn't like, very wide at the base but short and ending in a point, white, but it was quite hard. In the meantime I was totally naked while he/she had gotten rid of the thong and had remained in black garter belts and hold-ups with a pair of stiletto heels with a size 44/45, approximately; in fact he/she was big in physique and apart from the tits had nothing feminine (maybe the soul). In short, I settled on the bed, very eager and ready to welcome him inside; to be fucked by a semi-woman in my favorite underwear. I lay on my stomach, on my knees but with my back very low, my face and chest were resting on the mattress and my ass was high, my knees were wide so that my thighs and ass were spread as wide as possible; he licked my hole for a while and immediately after he smeared a cream on me, he leaned with his hands on my ass, I liked all this, I liked to feel the head resting on the hole, I liked to feel it forcing the hole (always quite tight). However, when he entered inside it hurt and I asked him to take it easy, because his cock was spreading my ass very much. Despite everything I didn't realize how good it was because after a few seconds and a few nice words but not very exciting he came inside (on the condom), I didn't even feel him pumping and slamming his balls against my ass (maybe he wasn't used to give it but only to take it). Anyway he told me it was wonderful (I began to understand women who didn't enjoy it because of their men) and he slumped down on top of me. He collapsed into me kissing my back. Although I had been disappointed by the whole thing my cock was a little hard from the excitement I had experienced during foreplay (those were better), so I told him it was my turn to enjoy. He begged me not to put it in his ass because he couldn't take it anymore. He convinced me and I was "satisfied" with a hand job; he didn't even take it in his mouth because he had run out of condoms; I had to believe it. The hand job and the cumshot were not so good. The feeling of disgust and nausea was stronger than other times and I wanted to leave immediately. To repay me the tranny gave me back 15,000 lire. I went home, by now my hangover was over, I put myself in bed and began to touch myself; this time I really got a nice hard cock; I took my woman's hand (who hadn't noticed anything) and I taught her how to use the car gearshift; we made up again.
After a few years without perverse thoughts, because of other thoughts, I found myself alone, without my woman. Alone I was no longer able to think of stories with men or transvestites/transsexuals but I needed a steady company of female sex, maybe I simply needed love but my dull mind was not able to understand who could give it to me but could only understand what should be her sex; maybe for a certain type of education received from my family, maybe for shame of the same and of friends and acquaintances as well as relatives, maybe for fear of revealing to myself what is my true sex.
By chance I met another woman. She was far from me and our love (or need, attachment, in short, call it what you want) was initially only platonic and only later real. Once I got back on track with a partner, the desire to transgress came back to me. I lived alone and strangely enough one evening I found myself walking again along the Navigli of Milan, near the park where was located the local trans; I took courage and entered, after a cocktail I left. The next evening I returned again to the club and watched the show, always alone; after the usual cocktail I left. I was about to return for the third time to the club when someone made an appreciation towards me; I had not noticed that there was a tranny sitting with half-open thighs on the stairs of a building near the club, perhaps he was resting, half-hidden. I approached and began to get acquainted. He told me he was new to the area. After a while we found ourselves (this time without having to bargain) climbing over a nearby gate that led to some stairs in a basement. I helped him climb over the gate by placing my hands on his ass to push him to the other side. There I fucked him, standing up. We began to kiss, he was sexting and very handsome, he had breasts a little small but very hard and well made, he looked like one of those I had dreamed of fucking while flipping through the porn magazines. I had him in front of me, we were both horny, I couldn't believe it, this time my dick was bursting under my pants, he was massaging it well, we were so horny and I was so hard we couldn't undo the buttons of my fly, finally we did it; he knelt down and took me in his mouth, he was sucking well with that hot mouth but I couldn't do it, I wanted to fuck him right away; but he was a bit taller than me, and he had to bend his knees a bit, he had his hands resting on the edge of the staircase, the miniskirt pulled up and the pantyhose lowered to half ass, it was not easy to possess him in that position, after a few unsuccessful attempts he gave a good push back and took almost all of him, how hot was his bowels, we stayed like that for a few seconds (just remembering this scene I'm getting excited), one inside the other, then I fucked him (or he fucked me), my pelvis and his went in perfect sync, he slammed his ass against me and did not stop, he wanted it, he groaned not caring about the danger he created, if some passerby could hear us or something, I began to grunt, like a pig, inside of him, his stockings hurt a little because they rubbed on my cock, as well as his panties (always thong), they also rubbed on the cock, but the pain made room for an immense pleasure. In that position we went on for quite a while because it was uncomfortable and a bit dangerous but in the end I managed to flood his bowels with a wonderful cumshot, full, loaded; I squirted him several times and he felt all those squirts inside because every time he gave tremendous blows backwards with his ass, he was still hard when he moved and took it off to bend over his knees and take it in my mouth, he sucked it making me suffer for the sucks that he gave, after having cum my head became very sensitive and with it my whole body and just a light touch of his tongue to make me tremble with pain and pleasure. We kissed again in the mouth. It was really a beautiful thing. She looked like a sexting girl in love and willing, because she put her arms around my shoulders and pushed her belly against my cock (which was now more hard than limp) to feel it all, she kissed me with an unexpected eagerness and then rested her head on my shoulders, I could not help but tighten my arms around her body to keep it forever clinging to mine.
Yet I made a mistake...I wanted him to enjoy it too... so I started kissing him again and my hand went to squeeze his ass and massage it, the other was on his breast but slowly went down; I felt his cock quite hard and his tongue at that moment became deeper; I lowered myself and pulled it out; his cock was brown and almost as big as mine, except that it had a slight downward curve, yet I liked it, I liked that cock (perhaps because it belonged to someone I liked), it was hard, very hard and so I took it into his mouth, how hot it was. But he turned cold and left me suddenly telling me he had to leave. With a jump (unimaginable until before) he went through the gate and left me there, with my cock still out and again super-excited. I sat and thought on the steps where he had been sitting until an hour before; I realized that I had lost him forever; maybe he really felt like a woman and wanted a man, a male and not the usual one looking for adventures. I didn't look for him and didn't go to that park anymore.
Now I've moved and recently married and I make love well, with love, I'm happy, yet the thoughts and cravings pervade me again.
I don't know how but I'm involving my wife (slowly, it's clear, she doesn't know about any of this); to take away her fear of taking it in the ass I lick her intimates for quite some time and then I just put the tip of my index finger in her ass, I limit myself on the condition that she does the same with me; she licks me under my balls and then moves on to my asshole and sticks the tip of her index finger in me and so, in strange positions we bugger each other with our fingers, without going further and without hurting too much. She likes to be put on her stomach and I on top of her but lately she amazed me; I was fucking her in her pussy in that position when, suddenly, she lifted a foot and put it on my ass, with her heel she made her way up to center my hole and started to push. That heel widened my buttocks a lot and at the same time it gave me a sense of fullness because it filled the entire entrance of my hole, almost widened it, doing so her calf rubbed against my balls giving me a wonderful feeling, I imagined I had the head of a cock resting on it. The result was that with every thrust of her heel on my ass in her pussy her balls were entering too, almost. I enjoyed in her pussy all my pleasure and without a condom too; now I can afford it, or not!!!?
I enjoyed it but I don't know the real reason why I wrote all this; maybe because I'm always looking for things out of the ordinary for me?
I hope you enjoyed reading my story.
After a few years without perverse thoughts, because of other thoughts, I found myself alone, without my woman. Alone I was no longer able to think of stories with men or transvestites/transsexuals but I needed a steady company of female sex, maybe I simply needed love but my dull mind was not able to understand who could give it to me but could only understand what should be her sex; maybe for a certain type of education received from my family, maybe for shame of the same and of friends and acquaintances as well as relatives, maybe for fear of revealing to myself what is my true sex.
By chance I met another woman. She was far from me and our love (or need, attachment, in short, call it what you want) was initially only platonic and only later real. Once I got back on track with a partner, the desire to transgress came back to me. I lived alone and strangely enough one evening I found myself walking again along the Navigli of Milan, near the park where was located the local trans; I took courage and entered, after a cocktail I left. The next evening I returned again to the club and watched the show, always alone; after the usual cocktail I left. I was about to return for the third time to the club when someone made an appreciation towards me; I had not noticed that there was a tranny sitting with half-open thighs on the stairs of a building near the club, perhaps he was resting, half-hidden. I approached and began to get acquainted. He told me he was new to the area. After a while we found ourselves (this time without having to bargain) climbing over a nearby gate that led to some stairs in a basement. I helped him climb over the gate by placing my hands on his ass to push him to the other side. There I fucked him, standing up. We began to kiss, he was sexting and very handsome, he had breasts a little small but very hard and well made, he looked like one of those I had dreamed of fucking while flipping through the porn magazines. I had him in front of me, we were both horny, I couldn't believe it, this time my dick was bursting under my pants, he was massaging it well, we were so horny and I was so hard we couldn't undo the buttons of my fly, finally we did it; he knelt down and took me in his mouth, he was sucking well with that hot mouth but I couldn't do it, I wanted to fuck him right away; but he was a bit taller than me, and he had to bend his knees a bit, he had his hands resting on the edge of the staircase, the miniskirt pulled up and the pantyhose lowered to half ass, it was not easy to possess him in that position, after a few unsuccessful attempts he gave a good push back and took almost all of him, how hot was his bowels, we stayed like that for a few seconds (just remembering this scene I'm getting excited), one inside the other, then I fucked him (or he fucked me), my pelvis and his went in perfect sync, he slammed his ass against me and did not stop, he wanted it, he groaned not caring about the danger he created, if some passerby could hear us or something, I began to grunt, like a pig, inside of him, his stockings hurt a little because they rubbed on my cock, as well as his panties (always thong), they also rubbed on the cock, but the pain made room for an immense pleasure. In that position we went on for quite a while because it was uncomfortable and a bit dangerous but in the end I managed to flood his bowels with a wonderful cumshot, full, loaded; I squirted him several times and he felt all those squirts inside because every time he gave tremendous blows backwards with his ass, he was still hard when he moved and took it off to bend over his knees and take it in my mouth, he sucked it making me suffer for the sucks that he gave, after having cum my head became very sensitive and with it my whole body and just a light touch of his tongue to make me tremble with pain and pleasure. We kissed again in the mouth. It was really a beautiful thing. She looked like a sexting girl in love and willing, because she put her arms around my shoulders and pushed her belly against my cock (which was now more hard than limp) to feel it all, she kissed me with an unexpected eagerness and then rested her head on my shoulders, I could not help but tighten my arms around her body to keep it forever clinging to mine.
Yet I made a mistake...I wanted him to enjoy it too... so I started kissing him again and my hand went to squeeze his ass and massage it, the other was on his breast but slowly went down; I felt his cock quite hard and his tongue at that moment became deeper; I lowered myself and pulled it out; his cock was brown and almost as big as mine, except that it had a slight downward curve, yet I liked it, I liked that cock (perhaps because it belonged to someone I liked), it was hard, very hard and so I took it into his mouth, how hot it was. But he turned cold and left me suddenly telling me he had to leave. With a jump (unimaginable until before) he went through the gate and left me there, with my cock still out and again super-excited. I sat and thought on the steps where he had been sitting until an hour before; I realized that I had lost him forever; maybe he really felt like a woman and wanted a man, a male and not the usual one looking for adventures. I didn't look for him and didn't go to that park anymore.
Now I've moved and recently married and I make love well, with love, I'm happy, yet the thoughts and cravings pervade me again.
I don't know how but I'm involving my wife (slowly, it's clear, she doesn't know about any of this); to take away her fear of taking it in the ass I lick her intimates for quite some time and then I just put the tip of my index finger in her ass, I limit myself on the condition that she does the same with me; she licks me under my balls and then moves on to my asshole and sticks the tip of her index finger in me and so, in strange positions we bugger each other with our fingers, without going further and without hurting too much. She likes to be put on her stomach and I on top of her but lately she amazed me; I was fucking her in her pussy in that position when, suddenly, she lifted a foot and put it on my ass, with her heel she made her way up to center my hole and started to push. That heel widened my buttocks a lot and at the same time it gave me a sense of fullness because it filled the entire entrance of my hole, almost widened it, doing so her calf rubbed against my balls giving me a wonderful feeling, I imagined I had the head of a cock resting on it. The result was that with every thrust of her heel on my ass in her pussy her balls were entering too, almost. I enjoyed in her pussy all my pleasure and without a condom too; now I can afford it, or not!!!?
I enjoyed it but I don't know the real reason why I wrote all this; maybe because I'm always looking for things out of the ordinary for me?
I hope you enjoyed reading my story.
