I met up with this guy and it was very clear that his pictures didn’t lie. I was almost brave enough to drive over in my full outfit but I ended up wearing it under some other clothes… but I was wearing a skimpy schoolgirl out, black high rise g-string and a cute, matching bra.

When I got there we went straight to the bedroom and he stripped off, revealing what was already an impressive cock even though it was only semi hard. It was about 8” and a little bit thick, when I’ve only ever had 6” before.

I lay down and he knelt beside me, so it was clear what he wanted. After a bit of stroking, I took him in my mouth and it felt so full. I worked my way down as far as I could but could only get halfway. I guess I need more training!

After about 5 minutes he told me to get on my knees and bend over. At first I couldn’t take it so I asked if I could ride him so I could take him at my own pace. Eventually I got it in and boy did I feel a stretch!

He fucked me slowly from below for about 10 minutes and was again only half way in. I then lay on my back so he could be in full control and he built up slowly until he was all the way inside. He stayed there for a minute so I could adjust before starting to fuck me, getting harder and faster. Eventually we rolled so I was riding him again and I gave it my all, it felt so so good and we were both panting and moaning and covered in sweat.

We took a quick breather before I lay on my stomach and he entered me again with ease. This time there was nothing slow or gentle about it. He pounded my sissy ass hard for what seemed like a lifetime, changing speed occasionally but always ramming it home. He was going hard and fast before saying he was going to cum, and then he pulled out and came all over my ass and sissy pussy, as well as my soaking panties. It felt so good being covered in his cum.

He got up and left me lying there to catch my breath, which took a few minutes! I knew he didn’t want me to hang around so I got dressed and left. Now I’m lying on my bed with my panties still wet and still on wishing I could go another round.

What a BIG night on my sissy journey :) I hope you enjoyed my story x