I finally let it happen!

Hi all! So I know these are pretty common on this sub, but I wanted to share! I had been with trans women before, but this was the first time I dressed as a sissy and let a man take me, and I think I loved it!

So for starters, I had just bought first big haul of sissy things. Skirts, thongs, bras, wigs, stockings, etc… I was so excited when I put it all on for the first time. I literally was so horny and self pleasured over and over again. I thought that I would hit PNC from this, but I didn’t. It would last maybe 5 minutes, but after that I was craving more.

I snapped some sexy pics that I shared here of course, and that only made me go deeper. I bought my sissy stuff to dress up on my own and that would be it. But the more I posted, the more people I talked to, the more I saw how men just wanted to fuck me..the more I really wanted it. This time was different, like I said I had been with trans women, but this crave was for a man. I wanted a man to dominate me, to fuck me like a girl, I wanted to really be a sissy.

So when my urge kept growing I found myself on Grindr. I posted my pics, and waited. I filtered through a couple of flakes or guys that just wanted me to do car stuff. I ended up finding this guy who was visiting and had a hotel room near by. He seemed discreet and showed me his huge cock. And I really mean huge. I agreed to go to his hotel room, but on the stipulation that I could get ready in his hotel bathroom. I have never been out in public as a sissy, so I needed somewhere to dress, and he agreed.

I put all my sissy stuff in a bag and started the 5 minute drive over, stopping at the store to get condoms and lube. My heart the whole ride over was pounding and I felt like a knot was on my stomach. But I kept driving, the idea to stop and turn around just wasn’t in my head. I got to his room and immediately ducked into the bathroom to get ready.

He wanted me to wear my red skirt, stockings, black top, and wig, so I did what he wanted. His room was dark and the only light on was from the TV. When I walked out of the bathroom, he stood up and immediately pulled his pants down. I didn’t think, didn’t hesitate, just started sucking his cock. Fuck was it big, even soft I mean it was massive. I wasn’t even doing Chasity, and yet I still looked like a baby shrimp compared to him.

I did my best to please him, licked from tip all the way down to his balls and back up again. I got his cock all wet so that it just glided in my hands and mouth. I was literally dripping pre-cum just from sucking him off. After a few minutes his dick was pretty hard. I stood up and he immediately bent me over the bed. I got on top of it, and arched my back like a good girl. He spanked me a couple times and rubbed his cock on my ass.

I wanted it so bad, I slid my thong down and waited for him to make me a real sissy. He took his huge cock and pushed it in. It was hurting so fucking bad, it was here that I realized maybe I should’ve found someone with a smaller dick lol. For the next few minutes he slowly pushed in and out as I fought through the pain, I’d ask for more lube and we’d repeat the process.

Eventually once he was finally all the way in, he started to fuck me silly. I could hear the clapping of my own ass as he thrusted into me. I was holding my ass open with my hands, inviting him to put more of his cock in me. I was moaning and it was just coming out naturally.

He then flipped me over and started to fuck me missionary. I laid on my back, eyes closed, one hand holding my clitty, and the other on his back pushing him to go deeper. Watching his massive cock move in and out of me felt like a fever dream. He fucked me like the sissy I was. I had to stop him after a while because my ass just couldn’t take it anymore. He was nice and let me shower and change before leaving.

Unfortunately once I left I felt a sense of PNC even though I didn’t cum, and I felt a sense of regret. I haven’t dressed up since. Idk where it all came from, it was so random to just all the sudden feel shame ):

I’ve been replying it in my head since it happened and it still gets me hornier than ever. I’m starting to crave it again, and I’m definitely not going to let the next guy get away without giving me load to swallow or fill me up.