Next up was one of my favourites - an older guy who I got chatting to on alt.com. His wife and mine were both away on the same night, and he travelled up to Colchester from near Clacton wearing his wife’s panties and stockings under his regular clothes: this was to be his first time; my first time as a dom since my first meet; and my first time fucking ass.

It was late, and dark in my quiet road, and his instructions were to park up nearby (I’d given directions), let me know, and then approach the house once the outside light came on. He’d find the door unlocked, and then use the downstairs hallway to strip to his underwear, and then await me on his knees facing the door.

I was dressed all in black: 4” heels, open crotch tights, panties, mini skirt, tight fitting long-sleeved top; and a spandex hood with mouth and eye holes. This was to be anonymous - we planned to not see each other.

I approached him from behind, blindfolded him, and then gagged him with the socks I’d been wearing that day (telling them what they were as they went into his mouth). I added cuffs to his wrists and ankles, and put a belt around his neck, and used it as a leash to lead him upstairs to be used. I did, as we reached the top of the stairs, make a bit of an error and caused him to hit his head on a door… apologised straight away, but this was a bit awkward!

Once in the room, I instructed him to get on his back, and I attached all four cuffs to an under-bed webbing system that we have (the cheap kind you can find on eBay - escapable, but you can make a good go of it). I proceded to apply plenty of clothes pegs to his nipples, balls, and cock, and a few other places besides, plus a couple of strategically placed elastic bands around his cock and balls for extra torture. At some point - and I can’t remember when - I added some candle wax, in all the sensitive areas ;)

I removed my sock gag from his mouth to allow him to properly appreciate my ass, balls, and cock. It was the first time he’d done any of these, and seemed to really enjoy it, although I could tell he had a certain amount of disgust in himself too - he was reluctant to rim me, but went for it with gusto after a little while!

After a little while, I replaced his gag, but first stuffed a pair of my wife’s used panties into his mouth, again whispering what they were as I did so. He whimpered with excitement as I told him and pushed them in.

I released his wrists and ankles, raising his legs, and cuffing his wrists underneath them, so he was holding himself nice and exposed for me. I then pulled his panties aside, lubed up and fingered him - gently at first, but adding fingers and opening him up - until four went in quite comfortably.

I then dived in with cock! My first time fucking an ass, and I loved it. I was worried that I wouldn’t last long, and didn’t want a disappointing two-minuter, but was pleased when I seemed to be able to just keep going in a way that I’m only reliably able to do with my wife now. I pulled out and came on his ass, pulling his panties back in place.

This was probably the first time that I felt OK after cumming, but knew what it was like being early on in this life and letting go: I didn’t want him to regret anything before he’d left, so teased him a bit while he was restrained, but didn’t let him cum: he’d have to take care of that himself.

We did then talk for a few minutes, with faces on show - I don’t really know why - it was me who’d wanted it to be anonymous the whole time, but he asked to take off his blindfold, and then I felt a bit weird in the hood...

I did get pictures that night, but have unfortunately lost them in the meantime. Never met this chap again, but would have done so - I lost him when deleting accounts etc. a little while after. If you’re out there and reading this though, get in touch - I had fun!