My first transsexual I am Eduardo, 39 years old. Married with two still small children. We live in Madrid. I have a very normal life, as a father and husband, with a normal job. I try to do what I can to dedicate myself to my family and I think I achieve it. But you have to have a defect, and I, like so many other men, am quite a womanizer. It's not that I'm a real whore, but come on, two or three times a year, some woman who isn't mine, I put under her. I consider myself the macho type of man, educated only to fuck women. No other sexual relationship that wasn't with them had even crossed my mind. But I have learned that it cannot be said that I will not drink this water and hence the reason for this story, so that whoever feels touched and tempted by other experiences can count on mine in case it turns out to be beneficial. In the neighborhood where I live, very close, Tomás has his bar. Almost the entire neighborhood passes by there, since it provides good service, everything is very clean, and a lot of friendliness to the clientele. I got along very well with Tomás, because he is also a good womanizer and he keeps me very well informed of all the gossip that circulates in the neighborhood, if so-and-so is easygoing, if the other cheats on her husband, etc. It was a Saturday morning, around 1:00 p.m. I was having a vermouth at the bar, reading the press. Tomás approached me and motioned with his head to make me pay attention to my right. So I did and I met a girl who had just entered, stunning, exquisite. A young woman, tall, beautiful, very well proportioned, exquisitely dressed, something that was not common in the neighborhood. She was wearing a light mid-season coat, open, which allowed her to show off a daring miniskirt that left her perfect legs free, clad in black stockings and high-heeled shoes. Blonde, very well haired and discreetly made up. She looked about thirty years old and certainly a woman of distinction, one of those that you necessarily have to look back at as you pass by. Of course, when I have a woman like that nearby, I keep my eye on her, because if nothing else can be done, at least our eyes will be happy. So I put the newspaper away a little and ran my eyes over the woman's splendid silhouette, delighting in so much beauty. She realized it perfectly and was not bothered by it, as she moved her head a little to look at me and gave me a brief nod in greeting, with a slight smile. I loved his reaction. A woman who knows how to be, who knows how to appreciate the admiration that a man shows her, not like some other close ones, who look at them (without being disrespectful, of course, that is, without it being an insistent, rude look), and they get upset. But there has to be everything, of course. She was also nice. She addressed Tomás (she was already a regular customer), but with a lot of self-confidence and a wide smile. - Tomás, is my paella ready? Tomás also had a takeaway service. He gave the girl a bag with a container, she paid and said goodbye politely. As he passed by me, a new smile and a slight farewell. "See you later, good afternoon," he said. "Goodbye, beautiful," I replied, as I followed her with my eyes as she left. When Tomás freed himself from work and there were fewer clients, he approached me, leaning on the bar, to confide in me. - It's good, huh - Great, damn, the little girl has a lot of dust... - Hahahahahahaha….. - What are you laughing at? - Because the girl thing… ahahahaha…. It's a saying. He is a transsexual… - ¡¡¡ Joderrrrrrrrrrrrrrrrrrrrr …¡¡¡ No me lo puedo creer. She is quite a woman. Are you sure he has a cock? - Yes, it has, without a doubt, I have informed myself well. If Tomás said it, there was no doubt. Nothing escaped him, he perfectly controlled the entire neighborhood. - Didn't you say that you gave him a good fuck...haahaha? - Damn, not now... knowing that he's a guy. - Nooooooooo, don't be confused. Nothing about a guy, she's a transsexual and gorgeous, don't insult her with that guy thing, don't be old. In bed she is possibly an exceptional woman. - Yeah, yeah, but... Look, Tomás, I've fucked almost all the women I've slept with. But I can't imagine fucking a person's ass, reaching out and finding a big cock instead of a pussy... I can't even imagine it, come on. - A matter of taste, Eduardo. Nowadays these topics are seen with much more freedom and naturalness. I said goodbye to Tomás to go to lunch, not knowing that the next day, Sunday, a surprise awaited me. I was in the park, with the two children. I usually wear them for an hour before eating, while my wife takes the opportunity to go shopping. My cell phone rang. On the other side, a soft and sweet woman's voice spoke to me. - Hello... are you Eduardo? - Yes, it's me... tell me. - Well, I'm Elvira. My name doesn't mean anything to you. But I think you'll soon know who I am. - Now I'm not falling, sorry. - Sure, normal. Remember yesterday at noon, at Tomás' bar, okay? - Yes, I was there, certainly. - Clear. And a blonde lady came in to pick up a paella... At that moment it dawned on me. I was about to put my foot in it and say…Yessssss, the transsexual……. Fortunately I bit my tongue in time. - Yes, yes, I know who you are. - Sorry for calling you, if I bother you, tell me. It was Tomás, who gave me your phone number. I thought to myself that Tomás was a big bastard. He gave him my phone number to make fun of me, the bastard, you'll see when he sees it. She continued speaking, with her sweet, melodious voice. I was in quite a hurry, despite boasting of being a man of the world. - Well, I suppose Tomás has already informed you what kind of woman I am. He told me about you, your taste in women, etc. Have you ever been with a woman like me? He pronounced the word woman with a different accent, as if emphasizing his condition different from usual. - Well no, I have never been... I think I wouldn't dare, I don't know... - Look, Eduardo, life gives us a very varied sexuality. But they have constricted us with repressed education, they have loaded us with taboos. I listened, without saying anything. - And believe me, after seeing you at the bar, I liked you, you seemed like a very interesting man. And really, it's not that I dedicate myself to hunting and capturing guys, but this time I made an exception, and speaking with Tomás he also told me that you might be interested in something different... Is that so? - Well…. I think that's a bit of a tease from Tomás, he's very funny and to have a little fun, he gave you my phone number - I didn't know where to go. - Well, look. I know many men. I interact normally with them and I don't necessarily have to end up in bed. Sometimes we have drinks, talk, etc. Would you like to exchange opinions for a little chat with me? - Ehhhh, this…. Well, okay... I'll think about it. I will call you. - Thanks for thinking about it. I'll wait for you. See you later…. I didn't want to give him a hard no, because I'm not rude. But I hung up the phone with the certainty that I would never speak to her again. But during the week my curiosity was awakening. I didn't want to go to the bar, so as not to get into a fight with Tomás. But I couldn't get the girl out of my mind. What if I dared? What could I lose? If I don't like it - he told me, to convince me - just don't come back, then everything will be settled. I didn't really feel attracted to her being a transsexual, deep down I saw her as an extraordinary woman, one of those women who, if you can get them, become part of your life, even if it's just in one encounter. Anyway, the week went by and the following Sunday arrived. Me again in the park with my children. My cell phone in my hand, turning it over, I wanted to call, I tried to dial, then I regretted it. After a long moment of indecision, finally in a burst of will, I made the call. He picked up the phone and spoke to me without giving me time to say anything. -Hellooooo…..Eduardo……….thanks for calling. He had my number engraved with my name and he immediately knew it was me. His answer to the call, so natural, so kind, emboldened me a little. - Well, I just wanted to say hello, know how you're doing. - You know, Eduardo? I was waiting for your call, really, I've thought about it all week and I wasn't sure if you were going to decide in the end, thank you very much. We talked for a long time about inconsequential things. I didn't dare to make any specific request, and it had to be her who decided. And I got carried away, without thinking about it very well. -Eduardo... when can we have some beers? - Okay... whenever you want. Shall we see you at the bar? - No, no... It's not discreet, neither for you nor for me. Better at home, I'm in the building next to Tomás' bar. Will I wait for you tomorrow afternoon? - Okay…. He gave me the address and we met at five in the afternoon. On Sundays after lunch the kids would watch cartoons on TV and my wife would relax with a nap. I took the opportunity to go out and play sports. That's how I announced it. - Honey, I'm going for a walk. I'll be back in like a couple of hours. - Okay, when you come you stay with the kids and I'll go out for a drink with Amalia. Amalia was my wife's best friend. More than once, as a husband, I thought about whether those outings with Amalia were not really some encounter that they both had with some stranger. Being a whore as I am, one is suspicious thinking that everyone is the same as oneself. But hey, that's a separate thing now. I arrived at Elvira's house at the agreed time. She greeted me very sexy, with a short white nightgown, quite low-cut, and her stiletto shoes. Truly exquisite. Deliciously scented. Upon entering the small hallway of the apartment, two open doors showed the living room on one side and the kitchen on the other. - Do you want a coffee...? Yes?.. Well, make yourself comfortable, go to the living room and I'll serve it to you now. - No, if you don't mind, I prefer in the kitchen, so you don't bother coming and going. I like kitchens, they seem more personal to me, less cold than living rooms, especially of course if they are not jumbled. In this case it was a perfect example of cleanliness, everything neat and impeccable. I sat at the table while she heated up the coffee. I could see her perfect body, shapely legs, round hips and butt. The nightgown, although short, was made of non-transparent fabric, which did not allow us to guess her intimate attributes. He served the coffees and we chatted for a long time. Cultured woman, very pleasant in conversation, knowing how to be. His good preparation was evident. I asked him where he was from, he was twenty-nine years old at the time. - I am from a small provincial city. I came to Madrid, because in those cities everyone knows each other and situations like mine are not well tolerated, and I also did not want to cause pain to my parents with the comments. I came when I came of age. He continued commenting on things about his life. - It was clear to me very soon that I felt very much like a woman. When I arrived in Madrid I started hormone treatment, with medical supervision. I also take good care of myself. That has allowed me to be as I am...See?....Hahahaha. She moved from side to side, flirtatious, showing off her radiant beauty. - My figure is that of a real woman. Look…. She brazenly lowered the strap of her nightgown and left her left breast free. A delicious breast, totally round, firm, with a well-developed nipple. -No silicone, eh... Totally natural. They develop like this with hormones. You'll see later how pleasant they feel. - Damn - I said to myself - she doesn't cut a hair, it's already been announced to me that I will touch her tits. -And look at the legs...what do you think? She raised her nightgown a little, showing perfect thighs, not a hint of hair, glowing, perfectly hydrated skin. - Sorry, Elvira, for asking you... Do you charge for your meetings? - No, honey, I'm not a whore. I have a good job, clerking in a luxury clothing store. I earn enough for myself. But I'm not going to deny that once, if a man became very infatuated with me, and took me in a moment of financial trouble, I did charge him well. But only on rare occasions - Tell me, are you active or passive? - I can do what they ask me, I have no problems. - Women too? - Of course, most transsexuals are bisexual. After all, we have male organs and male hormones do not disappear completely. And that's why we like to put it in a pussy, there is no problem, at least for me. -And what kind of women have you dated? - Mostly co-workers who are looking for something morbid in their routine life. They are usually married women, some with some lesbian inclination. They want something different and with me they satisfy two desires, one, to have inside a cock different from their husband's, and another, to sleep with a woman. Everyone is delighted. We finish the coffee and also a drink. Then she got up, grabbed my arm and led me to the back of the apartment, without saying anything, but with a very tender and reassuring smile. - You'll see how comfortable you are with me...Calm down. The bed was already open, with impeccable, ironed white sheets. The bedroom with very dim light, almost in darkness. He got into bed, while inviting me to undress. She covered herself with the sheet up to her waist and took off her small nightgown. Then, without removing the sheet, she also took off a white lace panty, which she dropped to the side of the bed. I understood that this way of undressing was not for her own modesty, but for mine, since she wanted to avoid the negative impact that her male genitalia could have on me. After also undressing, I entered the bed, also covering myself up to the waist. My member was flaccid, a product of nervousness. "What a bad feeling," I said to myself, "you'll see how I hit the trigger and it looks terrible." She leaned on me a little and began to treat me to a long series of kisses. I will never forget them, no other woman had ever kissed me with such mastery. She handled the inner cushion of her full lips and soft tongue like no other. He had fresh breath which I loved. I let myself do it, now somewhat more relaxed. Such was the delight of those kisses that I became completely hard on, but without even realizing it. I fell into the situation when she put her hand on my member. - Ayyyyyyyyyyyy, Eduardo….. that's good… ahahaha, what a hard cock….. Already aware of my erection, I began to act, less worried. I put my hands on her ass, pert, fleshy, soft. You could tell she was a gym friend. And the tits…uuuuffff. I was right, a very pleasant touch, a little harder than usual. I put the nipples in my mouth, sucking for a long time, while she continued with a gentle massage of my cock. I don't know how much time I would spend with those preliminaries. She decided the next moment, and so she did. - Honey, I think I have to be yours...I can't wait any longer. From the table he took a box of condoms and put one on me. She then stood with her back to me, lying on her left side, drawing up her bent legs and leaving her ass well exposed. He already moved the sheet aside so that he had a full view of her naked. I placed myself close to his back, a little across the bed, for a better fit. I pushed Elvira's upper buttock away with one hand. It was of course not the first time I had faced a dark hole. But this time it was different. On other occasions, a juicy female slit also appeared. Not this time. In their place appeared two beautiful, round, fat testicles. The entire area was exquisitely shaved. The presence of the glands did not cause me any type of rejection. On the contrary, it was like a new attraction. Aside from that, the view of the girl from behind was something out of the ordinary. A perfect woman silhouette. A back of exquisite skin, without any stain, very soft, smooth. Round, pert buttocks and warm thighs. I spent a good amount of time caressing his entire body, with my greatest interest and with flattering comments about his physique. She let herself be done, flattered. Without wanting to penetrate her yet, I spent a long time with my cock wedged between her buttocks, rubbing up and down. When I have done it other times, after rubbing the anal part like this, the member then fits into the wet pussy, back and forth. Now the tip of my cock was against my testicles, which prevented me from going any further. I pressed hard against them, delighted by the new sensation and went back to repeat the movement. She moaned sweetly. I had the stake like a post, my fears were over. I considered that the moment had arrived. But I was a little embarrassed to start penetration without adequate lubrication. - Honey... don't you want me to put some cream on you? - No honey, it's not necessary. You have me very excited, I feel very open from behind. Plus, the condom already has lubricant, don't worry. But of course, be careful, don't be abrupt, please... I raised my upper buttock again with one hand and with the other I grabbed my cock, bringing it to her entrance. She was right, it was pretty easy. I squeezed gently, but firmly, and fit half his member without any difficulty. - How delicious, darling... - I exclaimed, sincerely. It would be the novelty or I don't know what. But the sensation was much more delicious than the one I had felt when screwing the women who had been my lovers. She appreciated my care. - You are a very delicate man... They were all like that, really... Thank you. I also love that you are inside me and that you enjoy it so much. She had slightly raised her right leg to facilitate my penetration. Now I could see his entire testicles and his virile member. Elvira had a more or less normal member, perhaps a little bigger than usual, but not out of the ordinary. I didn't have a full erection, I was just black pudding. I pressed a little more and very slowly, I introduced everything that was missing, without the slightest complaint on his part. Motionless, he let himself be done without protests. I also enjoyed silence. He held her very well. My left arm went under her neck and that hand grabbed one of her tits. With the other hand he continued caressing her ass, thighs and everything he could of her body. Still shy on my part, I didn't dare put my hand on his genitals. She had to be the one to act again. He grabbed my hand and brought it to his penis. - Touch me there, honey, I really want to… I handled the member he offered me. It was a strange sensation, I was so attached to her that when I masturbated her it seemed like I was touching my own penis. I also had no feeling of rejection. While stimulating her, I pumped slowly into her rectum, enjoying the narrow passage. She became fully erect, which pleased me greatly, as I felt satisfied to make her enjoy herself. Another long moment passed, of mutual complacency. She then pushed me aside. - Rest a little honey, I'm about to cum and it's still early. - Well, thank goodness you said it, I didn't lack anything either. Now he made me lie face down. - Relax, I'll give you a good massage. He took off my condom. He spread a generous amount of moisturizing oil over my entire body and performed a thorough, very erotic massage. The shoulders, the neck, the spine, he worked with great experience. He then went down to my ass and thighs, making me open them as much as possible. She smeared my testicles well, squeezing them carefully. He also smeared the ass crack well and rubbed the virgin hole. With well-oiled hands he inserted a finger into my anus and moved it in circles. When he had it slightly dilated, he inserted two fingers and repeated again. The sensation was extremely pleasant. After about fifteen minutes, he turned me over and put me on my back. He repeated the massage on my chest and belly. Also on the cock, but very briefly, since I had a tremendous erection and she, an expert, knew that I could cum at any moment. Then he made me lift my ass to put the pillow under my hips. That way my pubes were raised. He now made me open my legs wide, as if I were a female. And she placed herself between them, completely lying on top of me, all of her skin on top of my body. Their genitals were rubbing and feeling his cock rub against mine was the strangest sensation I've ever had, but without a doubt one of the most pleasant. His testicles felt good to sway over mine, then rise, rubbing them along the shaft of my cock. I can't barely describe such an exciting situation, I lack words. It made me enjoy a lot. I already had to tell her that the end was near. - I can't take it anymore, Elvira, I can't take it anymore... - Eh, eh... no, no. Still, still, we still have a long way to go. He withdrew without touching me and let a couple of minutes pass, looking at me slyly. - Are you okay, honey? - In glory, Elvira, you don't know it well, you are wonderful. After that brief time, in which I had cooled down somewhat and was not in danger of finishing, he bent over to the table and grabbed another condom, putting it on his own cock. I imagined what was going to happen. I had the last burst of repressed machismo and made to stand up, but she grabbed me by the shoulders and made me lie down again. - Don't worry, Eduardo, don't worry, it's easier than it seems, you'll see. Positioned on her knees between my open legs (I looked like a real whore in that position), she leaned on one outstretched arm and with her other hand she grabbed my erect member, ready to attack me without further ado. In the position I was in, with the pillow under my ass, it was quite easy for her to access my butt, although it requires a little cooperation as well. - Relax, don't think about anything, let yourself go... Open your buttocks a little, please. I, obediently, spread my buttocks with both hands and waited for whatever had to come, at that point I had to endure. There I was. A complete alpha male, unrepentant fucker of women. About to be assfucked. I would never have imagined it, but now I had a woman on top of me, delicious, of immense beauty. I didn't think at that moment that this woman had a phallus and that she was willing to insert it into me. That, despite everything, was almost a secondary issue. Now I wanted her to enjoy me, as I had done with her. Tremendous adoration for her and great submission overwhelmed me. I was like an object man, submitted, surrendered. A feminine and unknown facet until then had emerged in my mind and in my body, and without ceasing to be the man in me, I was now discovering, as she had told me, that sexuality is much more than the penetration of a man into a woman. She repeated again to calm me down. - Relaxed, honey, relaxed, don't press, don't press inwards, it would hurt. Leave your ass to its own devices, as if nothing were happening. Forget everything... I felt the pressure of the tip of the member. In my experience as an assfucker of women, I knew well that the worst moment was the entrance, the dilation of the sphincter. I tried to relax, as she advised me. - Ayyyyyyyyyyyyyyyyyyy, ayyyyyyyyyyyyyyy…. I complained a little, but not much. The anus was already slightly dilated with his fingers and the lubricant from the condom made entry easier. I continued with my eyes closed, I was really embarrassed to look at her. The glans had entered and she waited for me to adjust. He continued to encourage me, he was certainly a charming person, infinitely sweet. She was very attentive to the reaction on my face. If he noticed a gesture of pain on my part, he would stop and withdraw a few millimeters. If he saw that my gesture was one of pleasure, he pressed a little harder. She is on top, she dominated. - Don't worry, my love, you're doing very well, you're holding up perfectly. Keep it up, relaxed, good, good... I held onto her waist, to better carry the trance and at the same time feel that it was her, to feel her body and her heat. He still didn't open his eyes, shy, dedicated. She gave me a very long kiss for my good behavior, while taking out almost the entire member, leaving only the strict tip inside to prevent it from closing me. The slight back and forth movement helped me begin to enjoy myself. And now he pushed again decisively. She took a look at my lower abdomen, to check the situation. - Damn, honey, how are you, your cock is bursting... - Well, you... ahahahahaha. You have me totally impaled. - Impaled, but happy, I hope. - Well yes, why deny it, I'm comfortable. I completely relaxed now. Without fears, without reservations. At that moment I became a penetrated man, without complex macho nights. I enjoyed feeling the hard flesh of the woman inside me. She realized it and pushed all the way, until his testicles stuck to my buttocks. I opened my eyes a little and could see his radiant face. She was still very attentive to my reactions, in case the penetration bothered me and she had to withdraw something. But it was no longer like that, for my part there would have been no problems even if she had had it bigger. What's more, the situation was so surprising that I was even satisfied, proud, of having responded so well to my first incarnation. And as if I were a real slut, I returned with my hands to spread my buttocks. She realized my good disposition and now the push was tremendous, with all the strength of her hips, and delicacy could be put aside, Elvira knew that she could now fuck me almost ruthlessly, unleashing an overflowing passion. This time yes, I complained, of course, about the tremendous stake. - Ohhhhhhh, Ayyyyyyyyyyyyyy, ayyyyyyyyyyyyyy, not so much, not so much, Elvira. But she already knew that despite those inconveniences she could continue, she knew that I was already a man given over to his lust, that he could do whatever he wanted with me. So the strong pushing continued, although fortunately, it bothered me less and less. My ass had already gotten used to it. With his entire cock inserted into my ass like this, he let himself fall completely on top of me, equally relaxed, capturing the sweet sensations. - You look great, darling... -he told me- You have a virgin, tight, delicious, very hot little ass. You make me enjoy it a lot. I almost wanted to laugh. That they told me what I had said so many times to other women when I penetrated them, was still funny. We both remained almost motionless, feeling the intimate contact of our bodies. To make those sensations more intense, she would take it out halfway and put it back in all the way, sometimes with gentle movements, other times she returned to strong thrusts. I was so dilated that I didn't feel the slightest pain, only pleasure. So that she could accommodate herself well, I had spread my legs completely, like a whore and fucked female. When I sodomized them, some women told me that the anal area is rich in nerve endings and that is why you can also feel great pleasure. But I never imagined that I would receive the same coin. I don't know how much time passed. I lost track of it. We were so comfortable that none of us made any intention of leaving. Both with a terrible erection, I felt my member very hard and crushed by her belly. The sensation was that he was about to ejaculate, but without reaching it, in a state of continuous pre-orgasm that he had never felt. My testicles started to hurt. - Elvira, my love... I can't take it anymore, now I do, now I have to finish. - Okay, honey, we'll finish together. She sat up a little, just enough to reach between our bellies and grab my cock with her hand. He again started a faster and more powerful pumping in my ass, no longer feeling sorry for me. At the same time she handled my phallus well with expert movements, squeezing the head of the glans. I almost fainted with pleasure. - Ahhaaaaaaaaghhhhhhhhhhhhhh, ayyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyy. The exclamations were from both of us, simultaneous our respective orgasms. This time I opened my eyes wide, to look at his radiant face. She, on the other hand, had closed them, concentrated. Even more beautiful. I perfectly felt the contractions of his scrotum, which were transmitted to my rectum through Elvira's virile member when he deposited his jets of sperm into the condom, I perfectly felt that there were at least three of them. I only regretted that the usual precaution that must be taken in these cases forced us to use a condom, I would have liked to receive those jets directly inside me and take them with me as a precious treasure. While she came she didn't stop manipulating my member and at the same time she orgasmed I also released all my testicular contents onto my own belly, like a copious snowfall. She fell back on me, exhausted, not caring about also staining her belly with my sperm. But he did not remove the member from inside me, his youth allowed him to keep it very erect despite having ejaculated. We both continued for several more minutes enjoying such an intimate union. In the end the member came out alone, limp, exhausted, squeezed. He took the sheath off his cock and dropped it on the side of the bed. He again showed his gratitude. - Uffffff, Eduardo, you left me dry. What a delight, I think it was the best fuck I've ever had. - Well, I also say the same thing, Elvira... You have taken out everything I had inside me. You've made me a real man and... a real woman, damn. I never would have imagined it. Have I become gay? - No honey, you're not gay. Not at all. A true man who has discovered new sensations. Don't have any complex. You have made me very happy, thank you. - I was going to tell off Tomás, but I think I have to invite him to share a bottle of good wine...ahahaha. - Hahahahaha, yes, yes. Without a doubt, he was wise to give me your phone number. - I'm leaving quickly, Elvira, I'm late. I took a shower and he said goodbye to me at the door, with the warmest of his kisses. - Will you come back? - What do you think? I was Elvira's lover for a year. They are the most beautiful memories I can have. She was transferred from the city for work reasons and I lost track of her. Later I had an encounter with another trans, but nothing, nothing to do with her. Disappointed and certain that I was not going to find someone so extraordinary, I gave up new encounters with transsexuals. But everything she taught me in that year, which was a lot, I applied to my encounters with women and in that way I continue to remember and honor her.
