Hi all!

I am back yet again to share some of my sissy achievements! I just can't stay away! I am really starting to enjoy being a posting member of this community! If you haven't read my first two stories then what are ya doing? Go read them first.

Anyway, I am jumping a bit forward in my sissy history mostly because I want to talk about the first time I was ass fucked! So it started like any of my other sissy adventures! I met a guy on Grindr, surprise surprise, but we didn't hook up right away. We actually Snapchatted for a while first (probably about a week). I was sending him pictures and videos of me in different sissy outfits, and he was showing off his massive cock throughout the whole week. Needless to say we both were quite horny for each other and the sexual tension had definitely built to the point of explosion. Anyway, we both were busy during the week so we had to wait until the weekend which felt like forever, but we planned it out and somehow he convinced me to go over to his place (which at this point I would never do and even now I am very hesitant about going to meet up at some stranger's place. But he convinced me, probably because he had the legit perfect cock. I still have dreams about it to this day. We aren't in touch anymore, but wow if I could have one cock for the rest of my life it would 1000% be this guy's.

Anyway, let me get to the night it happened. So I dressed up super cute! Pink panties, well first I prepped and shaved and showered in my pink gem plug and then my pink panties, black lace stockings, my favorite black mini skirt and a cute tank top with a black jacket over top. I took a couple shots and a puff off a joint (as always, ahah) and started to drive over to his place! It was late at night, probably around 1:00 am so there wasn't anyone to see me outside, but as always I still had butterflies walking outside in my cute sissy outfit. He had roommates at his place (though they were asleep) so I was a bit nervous about going over there and I even almost backed out. But once I got there he came outside to calm my nerves and with that I was hooked.
Once we got up to his room and he shut the door, we talked for a while. He was a bit nervous, I could tell, but so was I, so it made me a lot more comfortable. He had me walk around his room and show off my outfit while he started rubbing himself through his shorts. I felt so hot strutting around his room and posing, showing off my ass for him! I still think about that moment a lot. He eventually ushered me to the floor in front of him, and I willingly dropped to my knees. I pulled down his shorts and was greeted with the greatest cock I have ever seen to this day. It was the perfect size, probably 7.5-8" with the perfect head and girth. I was instantly in love and knew I had to have it. Now, to give some context, I hadn't been fucked by a man at this point (not for a lack of trying though), but I had been training my ass regularly so I was ready and able, to say the least. But it didn't start with immediately fucking, no; first, I gave this man the best head he has ever received. I deep-throated his whole cock while maintaining deep eye contact. I was going crazy, the best performance of my life!

Soon he couldn't resist and stripped off my panties, skirt, and slowly pulled out my plug. I was so ready, but what I wasn't ready for was a kiss. This man grabbed my face and pulled me in for the hottest makeout session while fingering my ass. I didn't expect this, but I absolutely loved it. I was leaking like crazy and probably could've came just by his fingers if I didn't stop him and ask him to go get a condom (gotta be safe, girls). He grabbed it quickly and didn't waste any time throwing me on the bed on all fours. I was so amped at this point I didn't even care if he went slow, but this guy knew what he was doing and slowly inserted himself into me. I still dream about this feeling regularly; it was the most amazing feeling I have ever felt. Nothing can describe how good I felt when I felt him fully push himself all the way inside me. I felt complete. He rearranged my guts that night, and I am sure his roommates, if not his neighbors, heard me. I didn't hold back. He fucked me for probably over an hour before thrusting himself all the way in me and finishing deep in my ass. At that moment, I felt like my life was complete. I felt immense pride, not shame. I felt proud of myself.
He asked if I wanted to stay the night, but I was quite unsure how I would feel in the morning having to wake up in my sissy outfit in his bed and go home in the sissy outfit, so I declined. But in hindsight, damn I wish I stayed so I could've gotten that dick again. But alas, I got dressed and left. I got home and didn't even finish myself. I laid in bed and imagined what that man just did to me over and over and over again!

If you made it this far, thanks for reading! Stay tuned as I have plenty more stories to share and this, while one of my favorites, is definitely not my best;) As always don't be afraid to say Hi!!!!