Lola's First Anal Orgasm (Trans woman has her mind blown)
Hot Hook Up - A True Story - 29 Dec 2025
I remember when we first met. I was in the chemist's waiting on my estrogen when I noticed a guy across from me look at me, then his phone, and then me again. I instantly knew he recognised me from Grindr. I live in a rural area, and there are not many trans women around here, so I often get messages like "I saw you in the supermarket today", so I didn't think much of it. Later, in another store, he introduced himself and asked for my number. I wasn't comfortable giving it out in public, so I confirmed with him that he was from "the app" and told him to hit me up there.
I thought he'd never gotten back to me, but it turned out he had, and we'd been talking for some time. It wasn't until he showed up on Facebook's "People you may know" section that I realised it was the same guy I met in the store that day. I'd always been hesitant to meet up with a random guy I was talking to, but knowing it was him and remembering how fine he is, immediately put me at ease and arranged to hook up with him later that week.
He's Sri Lankan, and I've always had a thing for South Asian men and wanted to sleep with one, but for one reason or another, it hasn't happened for me, until today. He picked me up and took me back to his place, which was a palace compared to my tiny house. I took one look at his house and thought, "This is going to be the fanciest place I've ever gotten railed." He led me to his room and then did the last thing I expected: He gave me a hug. I'd had a bad week, so I needed a hug, but ruined the moment by starting to suck on his neck.
He pulled away from me, looked me in the eyes and told me I was beautiful. I kissed him and told him he was gorgeous, and we got into some heavy petting. Once we were both warmed up, he suggested we move over to the bed. We both started stripping down, him to his boxers and me completely naked. I think I surprised him with how quickly and easily I stripped off. What can I say? I have it down to an art. I joined him on the bed, and we started making out.
I took his cock out of his boxers and started stroking it while he sucked on my tits. I love having attention paid to my tits, so once again, he was giving me just what I needed. He'd sent me pictures of his cock, but they did not do it justice. I don't know if it's the biggest dick I've ever seen (I'd say about equal), but it was definitely the thickest with a big, beautiful head. I was a little intimidated, but I was not going to back down. I wanted him. All of him.
On the way over, he told me that I would be his first trans woman and like every guy with their first trans woman, he was keen to suck on my little girlcock. I enjoyed it, of course, but the whole time I was dying to get that big fat cock in my mouth. I finally got my chance and got confirmation that he was enjoying his first trans experience, as I was greeted with the taste of precum on my lips as soon as I kissed the tip of his gorgeous cock.
I love sucking cock, and when I go down on a guy, I want them to know how much I love sucking cock. If I've done that, then I know I've done a good job. Licking the shaft, sucking the balls and seeing how much I can jam down my throat are some of my favourite ways to worship a cock. Once I was done, I kissed him and then whispered, "Wanna fuck me?" "You want to fuck?" he asked, seeming surprised, and I nodded breathlessly. I got into my natural position (on my back), and he climbed on top of me and slid his monstrous cock inside me.
As much as I love sucking cock, I love being fucked even more. The feeling of fullness of having a cock in me, the pleasure of it moving in and out of me and the ultimate prize of being filled full of hot cum. I think it may have been his first time doing anal, and there was an adjustment period, but once he acclimatised to it, it was perfect. Despite his size and girth, there was no discomfort, and due to that big, beautiful head of his, he was soon hitting my G-spot.
He jerked my little girlcock while he fucked me, and I could feel the pressure start to build from the base of my shaft. "Oh fuck, he's gonna make me cum." I thought, shocked. It has been about 8 years since anyone apart from me had made me cum, and he was very close. He had to stop jerking me to steady himself, so I took over, but once braced, he fucked me harder, and the pleasure of him pummeling my prostate caused my brain to shut down and body to take on a life of its own.
I could hear myself moaning in a way that would embarrass me looking back, extremely loud and high-pitched, then suddenly, intense pleasure spread throughout my body like euphoric flame. Once I regained my faculties, I playfully asked, "You gonna cum?" He nodded and said he was close, so I whispered temptingly, "Cum in me, baby!" which sent him over the edge, finishing inside me. Afterwards, I cuddled into him and lightly caressed his chest while we had pillow talk.
When I tried to stand later, my legs were shaking. Once he dropped me off at home, I had to Google what the hell happened to me. Turns out I had my first anal orgasm. It was like nothing I'd felt before, and now I've experienced it, nothing short of that same bliss could ever satisfy. I'm seeing him again next week. I understand that he may never want to make me his girlfriend or little wifey, and I'm fine with that. I just want him to keep fucking me like that.
I thought he'd never gotten back to me, but it turned out he had, and we'd been talking for some time. It wasn't until he showed up on Facebook's "People you may know" section that I realised it was the same guy I met in the store that day. I'd always been hesitant to meet up with a random guy I was talking to, but knowing it was him and remembering how fine he is, immediately put me at ease and arranged to hook up with him later that week.
He's Sri Lankan, and I've always had a thing for South Asian men and wanted to sleep with one, but for one reason or another, it hasn't happened for me, until today. He picked me up and took me back to his place, which was a palace compared to my tiny house. I took one look at his house and thought, "This is going to be the fanciest place I've ever gotten railed." He led me to his room and then did the last thing I expected: He gave me a hug. I'd had a bad week, so I needed a hug, but ruined the moment by starting to suck on his neck.
He pulled away from me, looked me in the eyes and told me I was beautiful. I kissed him and told him he was gorgeous, and we got into some heavy petting. Once we were both warmed up, he suggested we move over to the bed. We both started stripping down, him to his boxers and me completely naked. I think I surprised him with how quickly and easily I stripped off. What can I say? I have it down to an art. I joined him on the bed, and we started making out.
I took his cock out of his boxers and started stroking it while he sucked on my tits. I love having attention paid to my tits, so once again, he was giving me just what I needed. He'd sent me pictures of his cock, but they did not do it justice. I don't know if it's the biggest dick I've ever seen (I'd say about equal), but it was definitely the thickest with a big, beautiful head. I was a little intimidated, but I was not going to back down. I wanted him. All of him.
On the way over, he told me that I would be his first trans woman and like every guy with their first trans woman, he was keen to suck on my little girlcock. I enjoyed it, of course, but the whole time I was dying to get that big fat cock in my mouth. I finally got my chance and got confirmation that he was enjoying his first trans experience, as I was greeted with the taste of precum on my lips as soon as I kissed the tip of his gorgeous cock.
I love sucking cock, and when I go down on a guy, I want them to know how much I love sucking cock. If I've done that, then I know I've done a good job. Licking the shaft, sucking the balls and seeing how much I can jam down my throat are some of my favourite ways to worship a cock. Once I was done, I kissed him and then whispered, "Wanna fuck me?" "You want to fuck?" he asked, seeming surprised, and I nodded breathlessly. I got into my natural position (on my back), and he climbed on top of me and slid his monstrous cock inside me.
As much as I love sucking cock, I love being fucked even more. The feeling of fullness of having a cock in me, the pleasure of it moving in and out of me and the ultimate prize of being filled full of hot cum. I think it may have been his first time doing anal, and there was an adjustment period, but once he acclimatised to it, it was perfect. Despite his size and girth, there was no discomfort, and due to that big, beautiful head of his, he was soon hitting my G-spot.
He jerked my little girlcock while he fucked me, and I could feel the pressure start to build from the base of my shaft. "Oh fuck, he's gonna make me cum." I thought, shocked. It has been about 8 years since anyone apart from me had made me cum, and he was very close. He had to stop jerking me to steady himself, so I took over, but once braced, he fucked me harder, and the pleasure of him pummeling my prostate caused my brain to shut down and body to take on a life of its own.
I could hear myself moaning in a way that would embarrass me looking back, extremely loud and high-pitched, then suddenly, intense pleasure spread throughout my body like euphoric flame. Once I regained my faculties, I playfully asked, "You gonna cum?" He nodded and said he was close, so I whispered temptingly, "Cum in me, baby!" which sent him over the edge, finishing inside me. Afterwards, I cuddled into him and lightly caressed his chest while we had pillow talk.
When I tried to stand later, my legs were shaking. Once he dropped me off at home, I had to Google what the hell happened to me. Turns out I had my first anal orgasm. It was like nothing I'd felt before, and now I've experienced it, nothing short of that same bliss could ever satisfy. I'm seeing him again next week. I understand that he may never want to make me his girlfriend or little wifey, and I'm fine with that. I just want him to keep fucking me like that.
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