This is an old pic of the now famous trans pornstar Ariel Demure. She sent me this selfie moments before our hookup. She was hot back then but she's lookin even hotter nowadays. Blessed to have spent that hour or so with her before she really blew up in popularity!
Not one I slayed but a story about one that got away. This was in 2003 and I'd gone to a friends house for a small get together involving weed and alcohol and we were all underage at the time so my friend was still living with her parents. I noticed there was this crossdresser there and at the time, I didn't think much of her and I mostly ignored her most of the night since I had no interest in CDs at the time. The first pic I linked is the closest i could find to this crossdresser's appearance. She was also dressed like the pic I have attached of Christina Aguilera from the early 2000s (so just use your best imagination). I was also going through a rough patch with my then gf and wasn't sure if we were still together or not. Basically I was just confused af at the time. Anyway sometime during our party we see the lights from a car pull into the driveway and the whole house gets quiet. We're all thinking the parents have come back and we all go into hiding. I ran into an upstairs closet to hide only to find the crossdresser was already in there. We make quick eye contact and I hide in there with her. As we're both hiding in there I notice she's in a squat position and her whale tail is showing. It looks very similar to the 3rd pic I posted, even the same kind of panties. My dick got so hard when I saw that! We made eye contact again but no words spoken. I moved closer to her and I put my left hand around the left side of her waist area gently caressing her waist and feeling her thong poking out of her jeans. We stared into each other's eyes while I was doing this (no making out even), and I'm certain if we were alone we probably would've had sex then and there. At that moment I was also thinking of my gf and our circle of people, and I didn't want any rumors to get out to other people we knew. After a while, our other friend yells out "Okay! They're gone!" So we exited the closet and resumed partying. We never spoke during the party and I left without getting her info. Not that it matters anymore, but I beat myself up over that now that I'm much more comfortable with myself now. Thinking about that moment still gets me hot and is a big "what if" in my life.