The first time I met up with a stranger for casual fun was when I was living in the South London/Kent area.

I’d got together a nice collection of gear, and was on a chat room of a crossdressing site, when someone local popped up. He was considerably older than me, in his 60s, and I was late 20s at this time, and quite heavy set, where I was still pretty slim.

We spoke for a bit, and he had the house to himself that morning, and was looking to be dominated. He hadn’t ever been wrapped in cling film before, and this was something I was interested in trying out.

He had an old jaw injury that meant he was unable to open wide enough to take a cock, and said that he didn’t like anal, but there were plenty of other ways that I’d be able to abuse him that we agreed on.

I dressed partially: black stockings and suspender belt, a black bra stuffed with balled-up socks, a pink g-string with a front zip opening (under the suspender straps), pink silk panties (over the suspender straps), and a tight fitting sleeveless black top. I put on my jeans and a jacket over the top of this, and slipped on some black ballet pumps for the very nervous drive over.

He opened the door cautiously, just peeping his head round, and I could see why once he’d closed the door behind me. He was wearing a knee length floral dress and red knee-high stiletto boots. He looked nervous too, which helped me to relax a little. I said something about needing to get changed, and he directed me to an upstairs room.

He’d laid out some things on the bed in there: an inflatable dildo, several clothes pegs, a rubber executioner-style hood, and a pair of dirty panties (which turned out to be his wife’s). I added the rolls of cling film, and a hood with detachable gag and blindfold that I’d bought along to the stack, and stripped off my outer clothes. I pulled on a tight black thigh-length skirt and a spandex black hood with eye and mouth holes, and slipped on some black stilettos with a 3” heel and ankle strap. I called out that I was ready, but I wasn’t really sure if I was… I was determined to realise some of my kinky desires though!

He came up stairs and entered: I was pleased with the positive reaction when he saw me. His mature and masculine face stood out a bit much for me though, so getting a hood on him was the first thing to be done. I instructed him to kneel – he was taller than me, so I wanted some better access.

I selected the hood that I’d bought with me. He unfortunately couldn’t take the gag, so I left this out. There was still a panel that fit over the mouth though, and the blindfold too. I left these both off for now, and I instructed him to stand again, and could see him shudder with nerves.

I crouched and caressed his boots, running my hands up to his stockinged thighs, and lifting his dress. As I got to his panties – another pair of his wife’s, plain black and used, it was clear that he was erect, although his cock was comically tiny: only a couple of inches or so.

I lifted the dress off of him, with his arms raised, and tweaked his nipples, pleased to find that they were sensitive. I felt compelled to kiss him then, and took exactly what I wanted, our wet tongues meeting as I groped at him. He had his hands on my hips and hungrily kissed me back.

I knelt him down, and sat on the edge of the bed, crossing my legs in front of him, and offering him a shoe to worship. He kissed and licked at it, sucking the heel, and running his hands up my stocking-clad legs. I dug the second stiletto into his tiny cock, and twisted it, before pushing him away, and doing the same to his nipples with both shoes as he whimpered. It was time to get him immobile.

I attached the blindfold to the hood, and stood him up again. I began to cover his torso and chest in cling film, with his arms folded behind his back until he could no longer use them. I pushed him back onto the bed, and he wriggled until he was straight and on his back.

I hitched up my skirt, and peeled off my outer panties. My cock was solid, and relatively huge. I wanted to try getting it in his mouth, just to see how much might fit, so I straddled his chest, facing his head. I poked at his mouth, but he genuinely couldn’t get anywhere near wide enough to let it in. I felt pity for him, knowing he’d never get cock in his mouth. He had a thorough lick of the tip though, and my balls too. After that, I nudged myself forward, pulling my g-string aside, and presented my ass to him. He licked it deeply and hungrily, and I rode his tongue for a good five minutes or so, really enjoying my first experience of having my ass eaten: my cock remained solid right the way through.

I took up the dirty panties from next to us, and offered him the crotch to lick at. After a few seconds, I pushed them inside, and kept going until they filled his mouth, before adding the mouth cover to the hood to keep them inside.

I turned my attention to his sensitive areas, and pulled his panties aside to expose his tiny package. I was still sitting above him, but now facing the other way, in a 69 position. I’d never had a cock in my mouth before, so I lowered my head and took the whole thing in. It was a disappointing first one to take, but something that I could now I say I’d done! He began to enjoy it a little too much, so I gently bit into him instead, and then reached for the clothes pegs.

He winced as the first one went on, but I didn’t let up. I just kept going until I couldn’t fit any more on his cock and scrotum. He took them well though, and didn’t complain. I carefully maneuvered his panties back into place, trapping them all inside.

I was getting ready to cum, and would have to leave quite soon, but there was one more special thing that we’d both wanted to do. I lead him to the bathroom, and helped him to climb into the bath, before removing his gag. He knew what was coming, and opened as wide as he could.

My piss splashed out straight onto his tongue, and I kept it to a steady stream as he drank every drop of it. I was impressed… I’d tried a little of my own in my solo kinky play, but struggled to get very far at all. As I finished and he swallowed the last gulp, he thanked me.

I quickly got myself hard again, and wanked as he licked at my balls and my hole again. Within a couple of minutes, I was ready to blow, and my seed followed my piss into his mouth, which he also swallowed.

Straight after cumming, I wanted to be gone. I felt dirty and ashamed… It was a very familiar feeling; the same every time I masturbated. But here, there was a stranger wrapped in cling film who’d just swallowed my piss and cum. I remained civil, but made a quick exit and said goodbye after returning to the state that I arrived in.

We never met again: there was a lot about my first meet that was disappointing – I would have liked to have a hole available to fuck, for one thing. It was mostly the shame of the situation though: I retreated from that world for a while, and soon deleted my accounts on hook-up sites. Looking back though, that morning was a lot of fun, and I’m definitely glad I did it.