I'll tell you my name is Pilar and I'm 20 years old, and my story begins like this. In reality, my name is Juan, but since I was 16, I've been living as Pilar. The thing is that since I was 12 or 13 years old, which is when you start seeing girls and getting interested in that stuff, it didn't happen to me much. Like, nothing interested me until I was 14, then I realized some things were happening, I played volleyball and when we'd shower, half the time I'd be looking at my naked teammates and feeling like something attracted me to that, but I didn't really understand what it was.
I clarify that I've always been very skinny, with red hair, always on or above my shoulders, and prominent buttocks, and my teammates would always tease me saying I had a girl's booty, and I'd always be clean-shaven. After some time when I was 15 or 16 years old, I realized better that girls didn't interest me as much and that when I saw porn videos, I'd get excited thinking it was the girl in the video and being able to do what they did in the videos, and masturbating thinking about that and honestly, it really got me excited.
By the end of the school year, if you had passed all your subjects by mid-November, you didn't have to go back to school, and as I was a good student, I didn't have to, so I'd spend my days at home messing around and watching hot videos and things that got me excited, and since my mom wasn't home, it was going great. It was then when I started seeing videos of guys with guys or trans or sissys, and they really turned me on. So in a moment, I started chatting with guys to talk about it, and that's when I adopted the name Pilar, and started talking to guys and it was super good and I had a lot of fun until one day I got along great with a guy named Raul and we started chatting on WhatsApp, things were going really well until he started asking for photos, he knew I was a guy but he'd ask me to take pictures in thong or naked and then send them back, which didn't make sense to me, especially where I'd get those. woman's underwear and clearly not my mom's jaja. And then I realized I had a bigger sister who when I was 15 left to live in Spain and left a lot of clothes, shoes, makeup, etc. in her room. And like the truth is that this guy Raúl was worth it and I couldn't stop sending him photos of him, so I grabbed some of my sister's underwear and went into her room and started trying on her lingerie, it was at that moment that my little secret did a click and knew there was no going back, when I put on the first thong inside my Booty and put on a bra I felt like the most slutty, but since I wanted to do it right I went to the bathroom and shaved all my legs, genital area, and pubic hair, I wanted to be perfect for the photos, so I took a lot of photos with different underwear and clothes from my sister's that had a lot of high-waisted pants and jeans that made me look like a Booty barbara and sent them to this guy.
As the days went by I spent most of my time in my sister's room getting dressed up and looking for things in the drawers, until one day I found a half-hidden box when I opened it had some sets with portaligas and that style, some plugs and a vibrator, obviously I tried on all her lingerie and got curious about the toys, I was playing with my fingers in my Booty and some little thing, gave me many desires to try them out and started using the plugs, and that's when the second click happened, I loved feeling that in my Booty that made it swell and get excited, it gave me a lot of pleasure, it became a daily routine for me.
Clearly I started chatting with more guys and they would ask for photos so I spent all day dressed up like a girl and that was amazing, already had passed a month and started looking at tutorials on how to make myself up and how to style my hair and those things. And the truth is that I loved it, I liked seeing myself as feminine.
Almost in January and starting to get hot, I couldn't stay locked up chatting like this so since I had a pool in my house I would go out and sunbathe and get into the swimming pool, and since I was dressed up like a girl all the time one day I thought it would be fun to wear one of my sister's bikinis, so I did, and spent the afternoon at the swimming pool with a super sexy bikini, but as I'm stupid when I left the swimming pool I realized I had gotten burned from the bikini marks and people could tell I was wearing nothing, so after that I only wore the part underneath the mesh and would sunbathe like a lizard, by the 10th day I was black as coal with white thong marks but honestly I didn't care and honestly I liked having those marks. During those summer days my mom told me if I didn't behave she could spend the weekends at her boyfriend's place and if I didn't misbehave I'd have to stay alone, so I imagined saying I'd be able to do whatever I wanted. So I took advantage of the weekends, got ready, put on a lot of clothes, I was already a woman, all I needed was a man and while I chatted with many guys or did video chat, I never committed to anyone because I was scared. One day Martin, one of my teammates from the volleyball team, who was 17 years old, handsome, 1.85 meters tall, muscular, and very well-endowed, sent me a message saying he didn't know anything about me and what I was doing, so I told him to come over to my house to the swimming pool and we could catch up, which he did, changing into one of those boxers that left little to the imagination, uff it drove me crazy, I clearly had a crush on him and seeing him like that was beautiful, I was wearing normal shorts and I almost died from wanting to be in a bikini, we spent the day at the swimming pool, fooling around and fighting, and at one point he leaned against me and I felt something and it made me laugh, he left soon after and I told him if he wanted to come back the next day. The next day he came back with the same boxers and I had decided to wear one too What marks my Booty bad, I should clarify that Martin was the one who used to annoy me most about my Booty, always telling me I had a better ass than women, and that made me think he liked it and I decided to test him. At a moment I bent down to grab something and did so showing him my Booty well and looked to see what Martin was doing and it's there when I see him looking at my Booty and biting his lip and seeing how he moves his mouth saying good ass, obviously without saying it. And then I realized that I had a chance, jaj, we went to the swimming pool and started playing and fighting, grabbing each other making faces and fooling around, until Martin got left behind me, trapping my arms and not wanting to want supporting his penis in my Booty and which felt very hard, at that moment I melted and let myself be taken by Martin, he started rubbing his penis on my Booty, he pressed it very hard and that made me crazy, at a moment I turned my head back and he starts kissing my neck, the earlobes, until I turn my head and he starts kissing, I couldn't believe Martin was kissing me, grabs me and turns me around facing each other and we start kissing passionately, sticking our tongues in each other's mouths, I was in heaven, and that's when he started touching my Booty again, massaging it like he had wanted to for a long time, at the same time feeling his hard penis pressed against my abdomen, I couldn't be happier. We stayed like that at the swimming pool until he told me to go to my room so we could be more comfortable. Already in my room he took off his underwear and put on a boxer brief and I went to change in the bathroom to get rid of my bikini marks, when he came in without saying anything and saw my bikini marks, well, and then I had to explain what I had done the last few months, to my surprise he told me he loves it when I dress up like a girl and that he can't wait to see me dressed like that again, and instead of putting on underwear I put on a thong and a short top-like shirt when he saw me.
So he jumped on top of me and started kissing me like a wild man, touching my booty full-on. We lay down in my bed and started kissing, when suddenly he grabbed my hand and took it to his penis through his boxer shorts so I could touch it. That lasted for a few seconds because the boxer came off and he asked me to masturbate him, which I did very well until I filled my hand with his warm semen. I cleaned my hand, didn't deny that I tasted a little of his semen's flavor haha. We got dressed and just as Martin arrived with a message from my mom saying she was almost there, we got dressed and Martin left. The next day at night, Martin sent me a message saying 'Pili had an excellent time, can't wait to see you again', I died that he called me Pili, thought it was a little girl's name and I fell in love with him badly haha, so I told him to come over the next day. The next day he arrived and I was waiting for him in a red bikini that fit me perfectly, when he saw me he jumped on top of me again. That day we went to the swimming pool and we had a great time, didn't stop touching each other until we got to my room, where he asked me to masturbate him again while he sat in an armchair. He told me I could suck it, I said yes but I'd never done it before, he told me to just go for it, so I started giving him kisses and passing my tongue over his hard cock, which was about 16 cm thick, it was a dream come true. After being there for a few minutes, I started sucking his cock and tasting it, the flavor was rich and delicious, at 10 minutes in I could say he was almost coming in my mouth and I'd look up at him and see his face as he was coming and moaning, I stayed like that for 30 minutes and couldn't stop, I loved it. And then he told me to take his cum, so I said yes, started... to let out thick and hot streams in my mouth that would swallow me whole and tell me to open my mouth and show it, I open my mouth and then swallow it, I don't know but if there's something tasty it's the cum of my enemies I'm thinking of taking it, after that he sucks it a little more until it's clean. Days passed and Martin came every day to the house, clearly we were having fun in my room masturbating him and sucking him off, by the end of the week I was an expert cocksucker, on Friday of that week we were going at it in bed and since I'm flat I got on top of him and he started supporting his penis on the edge of my labia and running his fingers over my anus, putting them inside, which made me very hot, and he told me if I wanted to have relations with him, obviously I did but seemed like a teenager and wanted it to be special and then he said maybe but Saturday since my mom was leaving for the weekend we could relax so I told him to come at 9 pm that night prepared. On Saturday morning I woke up early and got into my sister's room and tried on a million things until I found a black dress that fit me well, with red shoes and it went perfect with a black set of clothes, and the rest of the afternoon I spent painting my nails, making myself up and styling my hair, when I finished I couldn't believe how I looked. At 9 pm Martin arrived when he saw me I couldn't believe it, I opened the door and told him come love and be super passionate, two seconds later we were already grabbing each other's Booty and squeezing it, he tells me I'm beautiful and makes me turn around, I had prepared a dinner with wine we ate a little took some wine but all that passed quickly because the two of us wanted to eat dessert haha so Martin went to the couch and I went to retouch my lip gloss, on the couch we started getting super passionate, I couldn't contain myself and started touching his cock and Booty and small tits, and in a moment he pulls out his cock And he tells me to suck it and how good a girlfriend I am because already she started sucking it, I don't know how long I was doing it but it was like 20 or 30 minutes until without telling me he filled my mouth with his delicious semen and I took it all and left his cock impeccable. From there we went to my room where we started undressing and when he saw me in the doorway he went crazy and took a thousand photos of me making thousands of positions, only wearing a thong and made me put on 4 and then lowered the thong slowly and started sucking my Booty, it felt so tasty and apart from that he was putting his fingers in while doing it, I didn't have to dilate because I used plugs daily, he kept me like that for half an hour until he made me turn over and put a pillow on my waist, opened my legs and supported myself on my little virgin and slowly introduced and pulled out, what a yummy sensation I was dying of pleasure, feeling some pain but the pleasure was all, and still hadn't had it all inside, after a few minutes his cock was surfing my Booty at its own pace and I couldn't help but moan like a slut in heat, what pleasure, I wanted to feel it all day inside me, he kept going for 40 minutes like a stud until I felt his semen coming out thick and heavy inside me. That night he had me, he took me in various positions, sucked my cock several times and so continued the whole weekend, I was his girl, girlfriend and slut, obviously we'll be together for a long time and did many pranks, all year we were together.
I clarify that I've always been very skinny, with red hair, always on or above my shoulders, and prominent buttocks, and my teammates would always tease me saying I had a girl's booty, and I'd always be clean-shaven. After some time when I was 15 or 16 years old, I realized better that girls didn't interest me as much and that when I saw porn videos, I'd get excited thinking it was the girl in the video and being able to do what they did in the videos, and masturbating thinking about that and honestly, it really got me excited.
By the end of the school year, if you had passed all your subjects by mid-November, you didn't have to go back to school, and as I was a good student, I didn't have to, so I'd spend my days at home messing around and watching hot videos and things that got me excited, and since my mom wasn't home, it was going great. It was then when I started seeing videos of guys with guys or trans or sissys, and they really turned me on. So in a moment, I started chatting with guys to talk about it, and that's when I adopted the name Pilar, and started talking to guys and it was super good and I had a lot of fun until one day I got along great with a guy named Raul and we started chatting on WhatsApp, things were going really well until he started asking for photos, he knew I was a guy but he'd ask me to take pictures in thong or naked and then send them back, which didn't make sense to me, especially where I'd get those. woman's underwear and clearly not my mom's jaja. And then I realized I had a bigger sister who when I was 15 left to live in Spain and left a lot of clothes, shoes, makeup, etc. in her room. And like the truth is that this guy Raúl was worth it and I couldn't stop sending him photos of him, so I grabbed some of my sister's underwear and went into her room and started trying on her lingerie, it was at that moment that my little secret did a click and knew there was no going back, when I put on the first thong inside my Booty and put on a bra I felt like the most slutty, but since I wanted to do it right I went to the bathroom and shaved all my legs, genital area, and pubic hair, I wanted to be perfect for the photos, so I took a lot of photos with different underwear and clothes from my sister's that had a lot of high-waisted pants and jeans that made me look like a Booty barbara and sent them to this guy.
As the days went by I spent most of my time in my sister's room getting dressed up and looking for things in the drawers, until one day I found a half-hidden box when I opened it had some sets with portaligas and that style, some plugs and a vibrator, obviously I tried on all her lingerie and got curious about the toys, I was playing with my fingers in my Booty and some little thing, gave me many desires to try them out and started using the plugs, and that's when the second click happened, I loved feeling that in my Booty that made it swell and get excited, it gave me a lot of pleasure, it became a daily routine for me.
Clearly I started chatting with more guys and they would ask for photos so I spent all day dressed up like a girl and that was amazing, already had passed a month and started looking at tutorials on how to make myself up and how to style my hair and those things. And the truth is that I loved it, I liked seeing myself as feminine.
Almost in January and starting to get hot, I couldn't stay locked up chatting like this so since I had a pool in my house I would go out and sunbathe and get into the swimming pool, and since I was dressed up like a girl all the time one day I thought it would be fun to wear one of my sister's bikinis, so I did, and spent the afternoon at the swimming pool with a super sexy bikini, but as I'm stupid when I left the swimming pool I realized I had gotten burned from the bikini marks and people could tell I was wearing nothing, so after that I only wore the part underneath the mesh and would sunbathe like a lizard, by the 10th day I was black as coal with white thong marks but honestly I didn't care and honestly I liked having those marks. During those summer days my mom told me if I didn't behave she could spend the weekends at her boyfriend's place and if I didn't misbehave I'd have to stay alone, so I imagined saying I'd be able to do whatever I wanted. So I took advantage of the weekends, got ready, put on a lot of clothes, I was already a woman, all I needed was a man and while I chatted with many guys or did video chat, I never committed to anyone because I was scared. One day Martin, one of my teammates from the volleyball team, who was 17 years old, handsome, 1.85 meters tall, muscular, and very well-endowed, sent me a message saying he didn't know anything about me and what I was doing, so I told him to come over to my house to the swimming pool and we could catch up, which he did, changing into one of those boxers that left little to the imagination, uff it drove me crazy, I clearly had a crush on him and seeing him like that was beautiful, I was wearing normal shorts and I almost died from wanting to be in a bikini, we spent the day at the swimming pool, fooling around and fighting, and at one point he leaned against me and I felt something and it made me laugh, he left soon after and I told him if he wanted to come back the next day. The next day he came back with the same boxers and I had decided to wear one too What marks my Booty bad, I should clarify that Martin was the one who used to annoy me most about my Booty, always telling me I had a better ass than women, and that made me think he liked it and I decided to test him. At a moment I bent down to grab something and did so showing him my Booty well and looked to see what Martin was doing and it's there when I see him looking at my Booty and biting his lip and seeing how he moves his mouth saying good ass, obviously without saying it. And then I realized that I had a chance, jaj, we went to the swimming pool and started playing and fighting, grabbing each other making faces and fooling around, until Martin got left behind me, trapping my arms and not wanting to want supporting his penis in my Booty and which felt very hard, at that moment I melted and let myself be taken by Martin, he started rubbing his penis on my Booty, he pressed it very hard and that made me crazy, at a moment I turned my head back and he starts kissing my neck, the earlobes, until I turn my head and he starts kissing, I couldn't believe Martin was kissing me, grabs me and turns me around facing each other and we start kissing passionately, sticking our tongues in each other's mouths, I was in heaven, and that's when he started touching my Booty again, massaging it like he had wanted to for a long time, at the same time feeling his hard penis pressed against my abdomen, I couldn't be happier. We stayed like that at the swimming pool until he told me to go to my room so we could be more comfortable. Already in my room he took off his underwear and put on a boxer brief and I went to change in the bathroom to get rid of my bikini marks, when he came in without saying anything and saw my bikini marks, well, and then I had to explain what I had done the last few months, to my surprise he told me he loves it when I dress up like a girl and that he can't wait to see me dressed like that again, and instead of putting on underwear I put on a thong and a short top-like shirt when he saw me.
So he jumped on top of me and started kissing me like a wild man, touching my booty full-on. We lay down in my bed and started kissing, when suddenly he grabbed my hand and took it to his penis through his boxer shorts so I could touch it. That lasted for a few seconds because the boxer came off and he asked me to masturbate him, which I did very well until I filled my hand with his warm semen. I cleaned my hand, didn't deny that I tasted a little of his semen's flavor haha. We got dressed and just as Martin arrived with a message from my mom saying she was almost there, we got dressed and Martin left. The next day at night, Martin sent me a message saying 'Pili had an excellent time, can't wait to see you again', I died that he called me Pili, thought it was a little girl's name and I fell in love with him badly haha, so I told him to come over the next day. The next day he arrived and I was waiting for him in a red bikini that fit me perfectly, when he saw me he jumped on top of me again. That day we went to the swimming pool and we had a great time, didn't stop touching each other until we got to my room, where he asked me to masturbate him again while he sat in an armchair. He told me I could suck it, I said yes but I'd never done it before, he told me to just go for it, so I started giving him kisses and passing my tongue over his hard cock, which was about 16 cm thick, it was a dream come true. After being there for a few minutes, I started sucking his cock and tasting it, the flavor was rich and delicious, at 10 minutes in I could say he was almost coming in my mouth and I'd look up at him and see his face as he was coming and moaning, I stayed like that for 30 minutes and couldn't stop, I loved it. And then he told me to take his cum, so I said yes, started... to let out thick and hot streams in my mouth that would swallow me whole and tell me to open my mouth and show it, I open my mouth and then swallow it, I don't know but if there's something tasty it's the cum of my enemies I'm thinking of taking it, after that he sucks it a little more until it's clean. Days passed and Martin came every day to the house, clearly we were having fun in my room masturbating him and sucking him off, by the end of the week I was an expert cocksucker, on Friday of that week we were going at it in bed and since I'm flat I got on top of him and he started supporting his penis on the edge of my labia and running his fingers over my anus, putting them inside, which made me very hot, and he told me if I wanted to have relations with him, obviously I did but seemed like a teenager and wanted it to be special and then he said maybe but Saturday since my mom was leaving for the weekend we could relax so I told him to come at 9 pm that night prepared. On Saturday morning I woke up early and got into my sister's room and tried on a million things until I found a black dress that fit me well, with red shoes and it went perfect with a black set of clothes, and the rest of the afternoon I spent painting my nails, making myself up and styling my hair, when I finished I couldn't believe how I looked. At 9 pm Martin arrived when he saw me I couldn't believe it, I opened the door and told him come love and be super passionate, two seconds later we were already grabbing each other's Booty and squeezing it, he tells me I'm beautiful and makes me turn around, I had prepared a dinner with wine we ate a little took some wine but all that passed quickly because the two of us wanted to eat dessert haha so Martin went to the couch and I went to retouch my lip gloss, on the couch we started getting super passionate, I couldn't contain myself and started touching his cock and Booty and small tits, and in a moment he pulls out his cock And he tells me to suck it and how good a girlfriend I am because already she started sucking it, I don't know how long I was doing it but it was like 20 or 30 minutes until without telling me he filled my mouth with his delicious semen and I took it all and left his cock impeccable. From there we went to my room where we started undressing and when he saw me in the doorway he went crazy and took a thousand photos of me making thousands of positions, only wearing a thong and made me put on 4 and then lowered the thong slowly and started sucking my Booty, it felt so tasty and apart from that he was putting his fingers in while doing it, I didn't have to dilate because I used plugs daily, he kept me like that for half an hour until he made me turn over and put a pillow on my waist, opened my legs and supported myself on my little virgin and slowly introduced and pulled out, what a yummy sensation I was dying of pleasure, feeling some pain but the pleasure was all, and still hadn't had it all inside, after a few minutes his cock was surfing my Booty at its own pace and I couldn't help but moan like a slut in heat, what pleasure, I wanted to feel it all day inside me, he kept going for 40 minutes like a stud until I felt his semen coming out thick and heavy inside me. That night he had me, he took me in various positions, sucked my cock several times and so continued the whole weekend, I was his girl, girlfriend and slut, obviously we'll be together for a long time and did many pranks, all year we were together.
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