I've not been able to meet a lot lately (2020...), but have engaged in a bit of solo play. Filmed my last session this week: I hadn't had anyone/thing in my ass for quite a while, and had bought a new dildo.
Got myself locked in chastity, hooded, and gagged, got clothes pegs on my nipples and had a nice ride for a few minutes. Want to do quite a bit more of this and see if I can get to the point where I can make myself leak from penetration. Quite a way to go, I think ;)
I filmed myself this week though: https://xhamster.com/videos/gagged-chastity-guy-rides-dildo-xhPBcSa.
I will get back to my experience stories at some point, this one's a quick departure.
So, saw some guy on Twitter who had humiliating pictures of himself saved in a Dropbox account - he shared the link with his username and password, and wanted to be locked out of it. So.. someone got in and locked it for him. Here's the link: https://www.dropbox.com/home/fag%20don%20willis%20for%20public%20exposure.
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!
Next up was a younger guy, after I'd moved up to Essex. We were both online of Fabguys late one night, and he could accommodate and had the place to himself. It was all quite straightforward - a simple 69 on the living room floor in the dark. We were both pretty tired though, and neither of us managed to cum. I left still feling horny, which made a nice change ;)
A little while after this I met an older guy when I was off "sick" ;) from work one day. I visited him where we both wore lingerie, watched porn together, and exchanged oral. He showed me some t-girl porn, a few of whom he'd slept with (as escorts) when he was in Thailand, and also some home made stuff he had of an ex - main thing I remember was her fucking herself with a courgette! He'd had a heavy night on the booze the previous evening and struggled to stay hard; I came in his mouth while he sucked me though.
I'd been chatting to a local tranny called Amanda for quite a while on various sites - she was the same age as me, also married to a vanilla wife, and we had a few other things in common too. One night, my wife had been out in London and she was home alone and dressed up. It was running a little close to my wife's return, so I was getting ready to call it a night and miss out on some discreet fun. Amanda and I opened up webcam, and she looked so cute... I couldn't resist her (I'd need to pick my wife up from the station, which reduced the risk a little). I got there as quick as I could and had a great twenty minutes or so with her, passionately kissing, and being sucked by her. I was expecting her to catch it all in her mouth, but she pulled away as I shot a massive load, all over my shirt! Had an awkward and quick walk back to the car (it was a warm summer evening, so nothing to cover up with), sped back home (about 90-95 most of the way up the A120), and then got a laundry on, just in time to get to the station...
My third, fourth, and fifth meets were all relatively vanilla, so I'll take care of them in one post.
The third was the first time I had my ass fucked. I was staying at my parents' again, and got talking to a guy on the Cottaging site really late one night. I drove over to his at probably 3 or 4am. He was older (probably late 40s), and shorter than me. He was top, and I'd been wanting to take cock for a while now. He started to strip me, fondling as he went.
Because crossdressing had always been an exciting part of things for me, I'd swiped a g-string from my sister's draws before I left, and he soon had me down to just this, which I was pleased he enjoyed ;) he put me on my knees and began to fuck my mouth, which I loved. He wasn't especially large, so his thrusts were fine to cope with, although I was gagging whenever he hit the back of my throat. This was the beginning of me wanting to become really good at deep-throating; something I've still not managed.
He moved me to his bed, and got me on my back before lifting my legs for a deep rimming - another first for me. Once he was satisfied that I was wet enough (and I was soon to find out that this was all he had in mind for lube!), he slipped inside (surprisingly easily), and pounded away for a good few minutes. At some point here, he drew my foreskin back, which is very painful for me: this is the moment that I found that out! I gingerly put it back in place as he apologised... He carried on, wanking me the whole time, and eventually pulled out to cum on me: my own soon joined his ;) I cleaned up and left soon after. We parted on friendly terms, but never met again.
Fourth one was a few months later, and was the second, and currently last time that I had my ass fucked. This one was arranged on Adult Friend Finder. While this ended up being a fairly vanilla session, we had both wanted to try out some pee play, and had both been drinking water to prepare.
I visited him in his home one day while his wife was at work, and his kids at school. We began by chatting a bit: I shared a bit about my limited experiences to that point, and he told me about he and his wife's experiences with swinging. She didn't know he was secretly meeting other guys on the side though.
We were both nervous to begin, but got going by helping each other to undress, and soon began to suck one another. After a little while, he grabbed some baby oil, and began to lube himself, inviting me in. I hadn't done this before, and was unfortunately just about ready to cum at that point, and trying to push in, I could feel myself about to erupt already! I tried to save embarassment by pulling away and waiting, letting things subside. It felt strange at that point though, which I wouldn't figure out until much later... We switched roles, and he oiled me up and began to take me from behind. I loved it ;)
We went for a few minutes before he wanted to delay his own orgasm. We went back to sucking and wanking each other, with him eventually pulling out of my mouth to cum on my chest - I had been planning on having him cum in my mouth, but in that moment felt glad that he hadn't in case it was a bit much for me. I did scoop some cum into my mouth to taste though.
I was finding myself unable to stay hard now, and we eventually gave up on me cumming. It was a few years later, when I developed an interest in chastity that I first read about ruined orgasms: I finally realised what I must have done to myself! We never id get round to the pee play though - still something I fantasise about trying though.
Fifth time out was the only one I've ever really regretted. Met another guy from Cottaging, and went to visit him. This one happened without seeing pictures beforehand, which was part of the later regret.
The host was friendly, but I didn't find him at all attractive. He was overweight (not necessarily a problem in itself), but the main thing was some questionable hygiene, particularly with how he kept his home (and being part way through a large McDonalds order didn't add to it much). I was feeling slutty though, and something about a guy who I'm not attracted to using me is appealing when I'm in certain moods, so I stuck it out.
We didn't get up to much: I came over his face after he sucked me, and then wanked him off (couldn't stomach sucking), and then got out politely, but as quickly as I could. I left with a lesson learned as he resumed his burger...
In the aftermath of that one, I was feeling quite disgusted with the whole thing, and tuned my back on all this pervyness for quite a while. I never met anyone else in the Kent area, and wouldn't resume my illicit activities until a while after I'd moved to Essex.
My second time was with an older crossdresser - I was staying at my parents' place in Bexley while they were away, and on the chatroom of TV Chix when a local popped up who I'd noticed before - as he was unable to accommodate, I'd never paid much attention other than perving over his pictures (great legs in nylon). He was looking, and I was in a rare position to accommodate, so made contact...
We spoke on the phone shortly afterward, and we both sounded nervous... we agreed on some things though. While I was also interested in, and indulged in, crossdressing, he made it clear that he only liked meeting with guys, and wanted to be the girl in the situation. There'd also be nothing anal on offer; that was all fine for me - I was still starting out, afterall.
He arrived looking like a normal guy in his fifties (which he was - I was still about 28 at this point), and hurredly retreated to a bedroom to get ready. I had a nervous wait for a few minutes while he transformed into a lovely looking MILF by the name of Gemma, wearing a short, tight black dress with black stockings and 4 inch heels, topped off with a brunette bob wig and well-applied make up. We sat together, not quite sure how to begin...
We talked for a while, as I recall, about how difficult it was to walk in her shoes, before my hand was guided onto her thighs and we began to kiss. This started escalating fast, and we were soon taking turns sucking each other, me naked once my robe had fallen away, and her with her dress hitched up and panties pulled aside. I came first, in her mouth - she told me afterwards that I was the first who had ever done that. I began to immediately feel that things were over for me, but didn't want to disappoint, but what had started as a desire to suck her and swallow her cum had scaled back to a hand job, leving her to cum all over my hands and her stomach. She was loud when she climaxed, and after she'd left, I noticed that the window had been open and was very hopeful that we hadn't been heard by the neighbours!
She left quickly after a quick change, and we parted on friendly terms, although never met again.
I have a very vanilla relationship with my wife, but have done some pretty exciting things with strangers that I've met online. I'll try to record some here.
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.
