Been a while since I shared any of my old stories and trying here instead of the other sub I used to post to as I think it’s more fitting.

So once again we find ourselves back in the good ole’ days of Craigslist. Again before I met my wife and was single and enjoyed doing whatever I pleased.

I was bored and browsing the personals for some fun when I came across an interesting one in the T4M with a title to the effect of Fist fuck my ass. This was something I had seen in a few pics and vid’s but had never actually tried so I was intrigued. Even more so when I found out they were only about 30 minutes from me.

A couple messages back and forth, a reminder that they were actually a boy on HRT (trap, femboi, etc weren’t as widely used then, at least that I knew) and a meet was set up. I was going to visit them and bring some vodka to loosen us both up.

I arrived and was let in by a cute, feminine boi in lace panties and a fishnet crop top. Long brown hair, a touch of makeup, sexy pink lip gloss and a nice bubble but as they turned around and led me inside a little studio apartment. If I recall they were about 21 or so at the time, I was around 28 or so.

I poured us some drinks and we sat and chatted for a little while. It turns out that we had messaged each other about a year before that and we both remembered the situation but we were unable to make anything happen at that time.

After the second or third drink and a bunch of talk of shared kinks, the time had come. Panties were discarded and a cute, soft floppy dick nice brown ringed asshole was revealed In doggy position. A big bottle of lube was brought out and soon my hand was being stroked like a cock to cover it completely and a generous amount was applied to her (gonna switch to that even though I have no idea what pronouns were preferred at the time but think she would approve) asshole. Looking at it I originally thought there was no way I was getting my whole fist in there but I soon learned looks can be deceiving.

I started out kinda slow, one finger, then two, then at her urging jumped to four. The bridge of my knuckles were stretching her anal muscles every time I pushed in and pulled back out and her moans matched the feeling of them gripping me.

I asked if she was ready and with a ‘do it already’ I tucked my thumb in and pushed hard. This ass was no stranger to being stretched as there was some slight resistance but my hand with four fingers out and thumb tucked in kinda popped in and she moaned in pleasure, maybe a little pain but I think that was the draw.

I paused my push just a little past the wrist and just started moving my hand inside her. Twisting from right to left, moving my fingers around, just kinda in awe that my whole hand was inside of someone as I let her get used to it.

After a couple minutes of light movements I felt her pushing back against it and decided it was time to just go for it. I flexed my fingers a few times and ended with them in an actual fist and started pumping into her. I went as deep as I felt I could and then backed off a little and went back to twisting it inside of her. Deep again and opening my hand a bit to feel her insides as I stroked it in and out.

This went on for a solid 10 minutes or so before she shot off a load of cum onto the floor and collapsed in front of me whimpering. I slowly pulled my hand out, still in a fist to make it as big as possible, and she shuddered and think she came again.

I met up with her to repeat this a couple more times over the next 6-8 months but that first time was the best and is something I’ll always remember.