ANONYMOUS GAY SEX - THE PLEASURES AND PITFALLS

The cock retreated and a condom was passed through with the hushed words, “Fuck me, please!”

The cock had tasted pleasantly of soap to I assumed the recipient of my cock was going to be suitable prepared for anal sex. I donned the condom and stuck my cock through the hole.

“Fucking Hell,” I heard reassuringly as he gazed on the piece of flesh about to enter him.

It took a bit of wiggling, his buttocks against the tip of my cock before I slowly entered his very tight hole. He pushed against me then started a rhythm while I stayed upright and didn’t move allowing him to be fucked rather than me fucking him. He was very, very tight and the grip on my cock was awesome. I could hear that the action was being appreciated from the other side.

After five minutes he gently slid off and as I went to pull my cock back, he gripped it with his hand and held me there. My assumption was he wanted more but just wanted to change position so I waited and sure enough, his buttocks pressed once more against me. He was still very tight and I couldn’t believe how difficult it was to re-enter. Usually once someone is opened, the second fuck is much easier. However I made it and the great thing was, the second fuck was even tighter and more awesome than the first. This time I gave him a great fucking which lasted around ten minutes before he slipped off again.

I pulled back and the cock came back through, straight into my mouth. As I sucked him he kept thrusting and the wall kept pushing towards me. It was like he was fucking the wall rather than my mouth. I heard a groan like someone cumming and prepared myself but nothing hit my throat. The action slowed slightly as his wall humping stopped but he still wanted sucked so I did and was, just a few minutes later rewarded with a generous mouthful of cum. He pulled back and the paper immediately blocked the hole.

I let him dress and leave before jumping up on my seat to watch the path, seeing two young sixth formers walking down the path smiling and gently touching each other’s hands. I assumed I had just been their first threesome and had fucked both of them only for one to fuck the other afterwards. I wanked myself off to the image of them walking across the park.

A Different Kind of Anonymous:

Rolling forward a few years to my late twenties, my wife had gone to stay with her parents on a “trial” separation and I was still leading the pretend life with straight mates and even the odd girl for company, never finding a new ‘Miss Right’ and with a small terraced main door house about ten minutes walk from town centre. Though a medium sized town it had quite a lot of peripheral industry which meant a lot of commercial visitors rather than tourists. The advantage of this was that an evening of lust could often be arranged with the use of Grindr or another similar app and the convenience of my little house made it easy to bring guys back should their hotel room be difficult. Most of the guys were the “my wife doesn’t understand me,” type but somehow I always felt their wives may never understand why they take a cock up their hole anyway.

It was a message on the gay version of a swingers app that perked my interest.

“Young guy working on contract in town for three days staying at a local budget hotel wants guys to fuck him while he lies blindfold on the bed in his hotel room.”

It was a “fuck and go” message which didn’t really appeal too much but the hotel was fifteen minutes drive from my house, I knew it had easy access as it was actually a motel where you paid when you arrived and could come and go without passing reception so I felt I had little to lose and might get to fuck a fit young workman. My ‘appointment’ was for 9.00pm and I was asked to be on time, go to the room, enter, close the door, fuck him, then leave with the door slightly ajar as I left.

Being naughty, I arrived early and sat opposite watching at 8.30pm. Sure enough a furtive looking thirty something guy wandered over and entered. He left at 8.45pm and the door was left ajar slightly. By my time no one else had come so I assumed he had made thirty minute intervals appointments but I wondered from when.

I went over, pushed open the door and closed it behind me. Sure enough the guy was lying splayed on the bed wearing a blindfold. He was very fit, tattoos on both arms and a leg, firm buttocks and short hair. He looked to be around twenty-two. The room was lit. I walked over and saw that his buttocks were covered in cum, I presume from previous visitors. There was a packet of condoms beside him and some lube so I was grateful the cum had been externally dumped on him. That was a turn on for me, less so than if someone had cum inside him. I fingered him as I one handedly tried to strip and he moaned as I did. He was thankfully very clean, if somewhat slippery.

I stripped completely and went back to playing with his shaven arsehole with my fingers. I inserted two digits and rolled my fingers around inside him reaching quite a depth into his rectum. I then rolled my cock around his buttocks spreading the cum over them as I did so. After a few minutes I put a condom and sat astride him getting ready to give him the full length of what I hoped was the biggest cock he was going to get that night. I positioned myself and pushed straight inside him in one go.

“Fuuuck!” he moaned as I pushed, “How fucking big is that?”

“Nearly nine inches mate and you are going to feel every one of them,” I said quietly.

I made sure he did. I fucked him as he had wanted, in the missionary position but decided to take more control and rolled him of his back, lifting his legs in the air and penetrating him straight up to the hilt. I fucked for around ten minutes not wishing to crash someone else’s appointment and shot my load with a heavy thrust inside his arse. I wasn’t sure of the protocol in these situations but felt we had already spoken and thought that was maybe “against the rules,” so kept quiet as I dressed.

“That was fucking awesome mate,” he said. “I hope we can do it again?”

“Sure thing,” I said, realising we had broken the rules twice.

I left as I saw a slightly overweight forty year old heading towards the room and realised there were some disadvantages in not knowing who was going to fuck you. I sat until he left and assumed he was the last, so departed.

Hosting anonymous sex:

“Looking for guys, singles or couples, for darkroom orgy. Must be fit, between eighteen and thirty and versatile for orgy in the area – time to be arranged.”

I decided to reply but any of these I had seen in the past had been from wishful thinking old guys who fancy a house full of youth. The reply interested me further as there were two pictures attached from a couple of very fit young guys I thought I had seen before. It took a minutes to realise it was the sixth formers from the glory hole a few years previously obviously still together, even more attractive and as horny as ever. There were a couple of face pics and cock pics. I replied with the same I received a very positive response when they saw my cock. They told me they had had another couple in their late twenties and pics were sent and were waiting to see if anyone else replied. I waited!

I had almost given up when the message came through to say they were hosting in a flat across town late one Friday evening. There was some pics of the two guys I knew, another couple who looked around thirty, a young, thin guy who was around twenty-one with a slightly geeky look but a cock that looked as though it might match mine and a small Chinese looking guy who didn’t give an age but looked young enough to be in the target group. The rule was we had to bring some beer or wine, condoms and lube. We had to be ultra clean and ready for action and it was suggested that some Viagra might help.

I was quite looking forward to this as, apart from the two lads, whom I really fancied anyway, I didn’t know any of the other people which surprised me in this little town.

I was there at the appointed time of 9.00pm on a cold November evening. The apartment was dark but had some dim lights around, I assume to stop us falling over the furniture. I was asked to strip to underwear and come through to the lounge are where furniture had been cleared back to the edges and the carpeting was sensibly had a couple of blow up beds and some towels strewn about. I had my drink in hand and introduced myself to the boys. It seems I was first so I used the opportunity to tell them we had met. I was surprised to find out they remembered the incident as it was the first time they had tried to have sex apart from with each other and both said they remembered my cock and looked forward to trying it again. Both kissed me on the lips and my cock reacted immediately. They both gave it a reassuring squeeze.

The second ones in were the other couple. They were gong to be the oldest but were both fine specimens so wouldn’t be the odd ones. Next the geek and the Chinese guy both turned up at the same time so we all ended up standing around knocking back wine, in our underwear.