One evening, my wife and I were talking and she, out of the blue, said, “I want to watch you fuck a guy.” I shook my head like I wasn’t getting what she was saying and she repeated it, adding, “Up the ass, your dick in his ass.” We had been playing with guys before, I gave a guy, Paul, my first full blow job a couple of month before, managing to cover my face with his cum. She licked it off, which was surprising and I must admit, felt really weird but resulted in me getting blown by her. I still love it when she sucks my cock. She was never interested in being fucked in the ass. We did try it, but it has never been a feature of our sex lives together.
I knew Paul wasn’t interested in being fucked, so we had to look a little further. We advertised in the usual contact magazines we had then, and after a few weeks, we met up with a guy, a bottom. The kids were at their grandparents, we were hosting, and this guy turned up. Kevin was smaller then me, about 2 inches smaller, young, early twenties, and I thought was struggling a little with his sexual identity. Being bi- then was not something talked about a lot, it was one or the other, at least not until people like David Bowie came along and HIV forced the conversation.
We talked around a bit, had a few wines, then Mary decided to push it a little further. She’s a bit of a dom when she wants to be, gets into a mood. She ordered Kevin to get up, then strip. He looked at me, I didn’t move, didn’t nod, nothing, so Mary told him again in that no nonsense, patient voice all mothers acquire. He stood, turned and began to strip. He did try to cover himself a bit when he dropped his boxers, but Mary wasn’t having a bar of that. He was trim and fine boned, fit, but not so well muscled they were clearly defined. He was a bit shy, but Mary told him to take hold of his nuts and stroke his cock. With a bit of encouragement, he did.
Like most guys then, he had been cut and when he was erect, you could see a slight upward curve to his cock, a large light purple knob and a good size, girth and length, down to a loose ball sack. Mary had him turn around and his ass wasn’t flabby, not large either, but more flat than rounded. Mary gave me the eye and I got up, stood behind him and ran my hands over him. He tightened a bit and hunched, like a cat does when you stroke them on their back, I thought. I touched his ass, then ran my hand around and began caressing his tool.
Mary ordered Kevin to get on his knees and suck me. He knelt, undid the belt on my trousers, opened them up and eased them down, then my boxers. I was half erect so he eased my cock into his mouth. Mary moved to where she could see better then came close. She too got on her knees and told Kevin that I was going to fuck him in the ass. While I was doing that, he was going to be fucking her. Would that be okay with him? He was a little surprised, Mary told me later, but he nodded. She reached over and began pulling his dick.
He was actually a pretty skilled cocksucker, not as good as some but a lot better than many. We kept this up for a while, then went into the bedroom quickly got naked. Mary had me lay on the bed with Kevin sucking my dick while she sat on my face. I love a sixty-niner, always have, and this is the second best thing to it and Mary was always so tasty until chemotherapy really fucked her system up. She hasn’t tasted the same since, but until then, I loved munching on her muff.
Kevin’s lips and tongue were giving me a great deal of pleasure as they slip up and down my cock. Then we swapped around. I began sucking his cock, while he was being face sat by Mary. That didn’t last long, again, Mary later told me he wasn’t that good, a bit of a surprise to me, but it was what it was. She had Kevin lie across the bed, she stood on the floor, bent over to suck him and I was fucking her from behind. This went on for a while but even I could see that Kevin wasn’t really enjoying it much. Mary said he was most happy when I was sucking him or he was sucking me, but in the end, she didn’t fuck him at all.
After a time, Mary moved us around again. She had him lie, face down, legs spread, handing me the K-Y jel. I put a heap on my dick and spread it around, then used some to wipe over his asshole. Didn’t bother with condoms in those days which was, with the benefit of hindsight, really stupid, This was probably the last few months before we began hearing about this dreadful new disease that was killing gay men, so we were considerably more lucky than anything else, I have thought. Yet, even then we all knew about other STIs, but really didn’t think it could affect, or infect, us. Get a jab of penicillin if it did and we’d be cured, I think, didn’t know it could kill us.
I lay on top of his back, and tried to enter him, but only succeeded in making a bit of a mess on his ass with the lube. I pulled his hips up forcing him into a doggy position then probed his ass, looking for the hole. I engaged it, then slowly slid into him. I could feel the ring of muscle around my cock and it was tight. It was certainly different, instead of it being enveloped with a pussy my dick felt it had a rubber band around it, sliding up and down it as I pumped his ass. I get a movement going that meant I would pull out to touch my knob on the inside of his ring and push in to slap my pubis on his ass. That felt nice, and it got better as I relaxed into the rhythm more.
I don’t have an overly big dick, just a “nice size” as Mary describes it, long enough to get in to touch her insides and thick enough feel like she is being filled up, a nice mouthful, she says. It must have been okay for Kevin too as he only grunted when I first entered him, and he was able to relax enough for me to be able to move without forcing it too much. I did as Mary had asked, kept fucking him until I emptied my fluids into him.
I rested for a bit, after pulling out, and decided, it was okay, but may be better with another partner. After me fucking him like that, I had to blow him, Mary wasn’t fucking him. I sucked his cock until he came in my mouth, but there was something missing here. It took me a while to figure it out, but it was obvious. It’s me, my problem. I’m a romantic, always have been but it wasn’t until I fucked Kevin that I understood that and the implications of that. I need a certain level of emotional contact, before, during and after sex, with anyone, male or female. I’ve tried very hard to overcome that, but have failed miserably. Fucking Kevin was mechanical, nothing in it. I couldn’t make any sort of emotional contact with him at all. No idea why.
I have tried anal, on and off over the years, but it just doesn’t do anything for me, I have decided. I really dislike being fucked and have only done it because Mary asked me to. I love the intimacy of sucking cock, licking pussy. I can fuck a pussy without any issue at all, but an ass, it’s just not the same. The other issue, I think, is that I love to cuddle after. The warmth of holding the person you’ve just had sex with is part of the emotional contact I have with lovers, for me, an incredibly important part. I’ve not met any guy who wants to do that with me. It’s like shoot your nut then, “Yep, that was good,” put on your pants and leave. I have a couple of friends whom I may invite one or the other over when I finish a story, get them to read it while I’m sucking them off. Mary might watch or go out, she doesn’t join in any more, not since the second bout of cancer, but doesn’t begrudge me a little sex play. Even with them, we might sit and have coffee rather than cuddling afterward.
That was the first time I fucked a guy up the ass.
Source: reddit.com/r/sexystories/comments/m570i1/fucking_my_first_guy_mm