When I was 20 (32 now) I hooked up with a trans woman and it went a bit further than I anticipated. She was late 30s and a bit thick/curvy. I told her up front that I was submissive, which she leaned into. She started by stripping me completely, putting me in my knees, and guiding my mouth to her cock... which was massive. Decently long, 7 in or so, but I could barely get my mouth around it. It felt so good in my mouth, I began sucking like my life depended on it. She picked up on how into it I was and started getting more aggressive; a tighter hold on my hair, thrusting roughly into my mouth, then throat, gagging me. I started moaning with each thrust into my mouth. I had never been used like this before and it was driving me crazy. She kept feeding off of that and started slapping me around and calling me her little slut. I responded by jamming her cock further down my throat, though sadly I wasn’t actually able to take her all that deep. At a certain point she stops and tells me she wants my ass. I was a little scared as I had never been fucked before, and she was, again, huge. However, I was far more turned on than I was scared and was somewhat relishing the challenge. Still, I asked her to be very careful given my anal virginity. She agreed, put me on all fours, lubing and teasing my asshole. She quickly had me moaning again. I was pushing hard against her fingers with my ass, forcing her fingers into me. It took only a minute or two of that before I lost it and begged her to fuck me. I had always been so careful with condom use... but when she she told me she had to get a condom I just begged her to fuck me. She didn’t need a second invitation and started teasing my asshole with her cock. I was losing it. I felt like I would let her do anything to me that night. She slowly pushed into me and unsurprisingly, I could barely take it. She paused for a moment, allowing me to adjust, then patiently eased into me further and further while telling me how good my tight hole feels and what nasty slut I am, begging for her bare cock. I was eating that up, and frankly, it was objectively true at that point. Unfortunately she was barely able to get all the way into me before the pain took me out of it and I tapped out. She pulled out, but I was still eager to be a good slut for her so I immediately started sucking her again, cueing more degradation. She got a good grasp of my hair and aimed all of her sexual frustration at the back of my throat. I’m just trying to hold off my gag reflex, unable to do anything about my profuse drooling. After I’m gagging too much to continue, she lays me on my back and mounts my face, smothering me with her ass while jerking off. She grinds on my tongue until she’s at the edge, then pulls back a little and sprays her load all over my face. After I caught my breath she finished me off and I came so hard I added a bit more cum to the already substantial amount on my face. It was a surprisingly intense experience for a hookup and among the best sex I’ve had in my life, but I still regret not being able to take a fucking long enough for her to cum in me...