My unexpected first threesome and bisexual encounter

This is a true story, only the names have been changed.

It is the story of how I came to have my first threesome and bisexual experience.

I am a six-foot three bisexual male, with a reasonable build for my age. I am married and have been since the mid 90’s. My wife knows that I have a strong interest or curiosity in bisexuality but does not know I am actively bisexual.

I had been bi-curious for a very long time and have been interested in trying anal sex since I was in my early 20’s. I have never wanted to penetrate another guy, rather I wanted to be penetrated by him, to feel his cock inside me.

I did not have my first proper bisexual experience until I was nearly 30. The desire to give it a go came after watching an old bisexual movie in the mid 90’s by mistake. The movie was called “The Big Switch”, I'll never forget it.

I never really had an idea of what my first experience would be like, or how I would approach the idea with someone. I certainly never expected it to be with a work colleague and his girlfriend.

Ashley was a good-looking guy and was about ten years older than me. He too was six-foot three and had a good body for his age. I had heard a whisper that he may have been bisexual, or at least had some kind of bisexual encounter in the past. His girlfriend, Karen, was a reasonably good-looking girl. She was a lot of fun, the life of the party, especially when she had been drinking. After she’d had a few drinks, she would often flash her tits at us at the drop of a hat. I always thought she might be a player while she was drunk.

We were all part of a large group of friends, and we all would get together at one of our homes on most Friday or Saturday nights, for a few drinks and something to eat. We also would listen to music and dance. On some occasions, usually after many drinks had been consumed, the group chat would drift towards sex. The girls in the group would talk about their sexual experiences and the various toys they each had. As most of our group lived on the same street, it often meant they would go home, get their toys, and bring them back for a show and tell. The toys were only brought out for a laugh, and I never saw the toys being used on themselves or each other.

On one of these drink nights, we were at Ashley and Karen’s home. We had all been drinking, and as usual the conversation and antics had drifted towards sex. As this night came to an end, everybody had gone home and I found that I was the last one there, alone with Ashley and Karen.

The conversation during that night was about girls giving head jobs. Ashley and I were sitting on the front veranda having our last drink of many, when he told me that Karen loved to give head jobs and was very good at it. He turned to me and said, “she would give you one!”. This caught me off guard, and I didn’t know what to say. He went on to say that he could probably get her to give us both a head job at the same time and asked if I wanted to have a bit of fun and see if she would? I really thought he was joking, but I said, “Why not!” A short while later he got up and told me to follow him into their bedroom.

What Ashley didn’t know was that Karen had already given me a very quick head job, only recently. It was only a very brief one, that had come about because of a truth or dare game at a previous drink’s night.

Once in the bedroom, Ashley told me to take off my pants and jocks and sit on the end of the bed. He did the same, sat on the bed next to me and called Karen into the room. When Karen walked into the bedroom, she stopped just inside the doorway. With her hands on her hips, she looked at us both and started to laugh. She too was very much intoxicated, so I thought she would tell us to fuck off, turn around and leave the room. She did not.

Karen dropped her hand to her sides and said, “Are we really doing this?” Ashley and I looked at each other, then back at her and said “yep”. I still thought this was a joke that they were both playing on me. I was about to find out it was not.

Karen came over to us on the bed, knelt on the floor between us and began masturbating us both at the same time. Ashley had a good-sized thick cock, very similar to mine, and now we were both hard. She gave Ashley a head job, while continuing to masturbate me. After a short while she lifted her head off his cock, turned towards mine and lowered her mouth over it. She was giving me a head job, and as Ashley had said, she was very good at it. Karen continued to masturbate both of us, swapping between our cocks to give head jobs. At one stage I was ready to explode, but she must have sensed that and stopped, switching back to Ashley’s cock before I’d cum.

This went on for 10 minutes or so, at which time Karen stopped. She stood up, took off her pants and knickers and said, "it's my turn." I knew what she meant, but I wasn’t sure if I was supposed to be the one to do it. I loved going down on women, but she was Ashley's girlfriend. Ashley got up off the bed and she lay down where he had been. He then knelt between her legs and went down on her well-kept, trimmed pussy.

I watched for the first couple minutes. It was the hottest thing I had ever witnessed in person. Karen invited me to play with her breasts, which I tentatively did. A little while later, I saw Karen begin to shudder, she let out a few whimpers and came with a loud moan. She flopped her arms on the bed above her head and just lay there. She looked very relaxed. Ashley got up and walked out of the bedroom, saying he was going to get a drink.

After he left, Karen turned to me and asked if I’d like to help her stir him up, like he did to her. I said sure, not really knowing what I was getting myself into. She told me that when Ashley had been drinking, he often had bisexual tendencies. She said that he had fucked other men before, but only after he had heaps to drink. She said she thought he was at that stage now. She said we should give him a choice and see what he did. She said that we would both get naked, get onto our knees on the bed, with our bums facing the door. When he returns to the room, she said she would tell him to take his pick.

I was intoxicated, but not to a point where I didn't know what I was doing or had no control of myself. I was also extremely horny, so I said, “why not?”. Even if nothing happened, it would be a bit of fun.

I didn’t remember ever telling Karen that I was bi-curious, so I wasn’t sure how or why she thought I would go along with her plan. I did think she was kidding about Ashley being bisexual, as I had known him for a long time and never had any clue. I didn't have any expectations that something would happen anyway.

We did as Karen said, got naked, and got onto our knees and elbows on the bed. With our hips touching and bums facing the door, we waited. It wasn’t too long before I could hear Ashley coming down the hallway. I started to tense up with anticipation, not knowing what he was going to say or do.

Ashley entered the bedroom and stopped. Like Karen, he stood there and started to laugh.
Karen was gently bouncing her hips against mine, putting on a playful display. I started to get an erection and I could feel my cock swinging from side to side, banging against my inner thighs. No doubt he would have been able to see it too.

Karen told him to take his pick! As he stood there, I could see he was becoming erect. He put his drink on the dresser and said, “not a word Johnny, not a word.” He approached Karen and without a hesitation, drove his erect cock into what had to have been a very wet pussy. I looked at her and she back at me, we smiled at each other. I went to get up, but she reached out with her hand, took hold of my forearm and whispered, “stay there!" I got back down onto my elbows and watched him sliding in and out of her pussy. This went on for a while and I was enjoying my very close, front row seat. It was the first time I had been in a room watching a couple fuck in real life. I knew I was enjoying it because my cock was rock-hard and dripping pre-cum.

Ashley stopped and pulled out of Karen. I saw that his cock was still hard and was dripping with her juices. He moved around behind me, and I felt him put both of his hands on my hips.
I still wasn’t sure if he was going to do anything, I still wasn’t convinced that he was bisexual as Karen has said, so I expected him to simply go back to fucking her!

Ashley took his right hand off my hip, but as his other hand was still on my left hip. I wondered what he was doing. Suddenly I felt something push against my anus, not with a lot of force, but just enough to let me know something was there. I had a look between my legs to see if I could see what it was. It could have been his thumb, but it felt more like a dildo. It may have been his cock, but I had never felt one against my anus like this, so I had no way of knowing. Whatever it was, it did feel warm.

He started to gently thrust it against my anus. This went on for about 30 seconds and felt good.

Ashley backed away from me. I felt some cold fluid land on the top of my arse. I felt it run down my arse crack and over my anus. I felt something against my anus again, and he was rubbing it up and down to spread what I guessed was lubricant. I looked between my legs and saw that he had his cock in his hand, and that it was the head of it he was using to spread the lube.

I knew things were getting real, and I was now starting to wonder what I would do. I had always loved anal play with dildos, cucumbers, and had always wondered what a real cock would feel like inside me. I knew there was a very real chance I was about to find out, but would I chicken out or just take it? This would be my first time, it meant that I would have been fucked by a man. This is something that I could never change, and there was no going back.

Ashley was still rubbing the head of his cock and down the crack of my arse. As it went over my anus, he would thrust in a little, getting a little harder each time. Finally, he stopped directly on my anus and began thrusting against it, going in a bit and then backing away. He continued to thrust, slowly getting the head of his cock deeper in me each time he did.

It was at that moment; I made a conscious decision that I was going to take his cock inside me. After all, I had wanted to feel a cock inside me for a very long time. I had a stumbled across a willing bisexual male and I knew I may not get the opportunity presented to me so easily like this again.

I relaxed my anus and felt Ashley’s big thick cock slide into me. He was only just inside me; I could feel the head pulsing gently. I started to gently push back onto him as he thrust into me. Each time he thrust I pushed back a little harder, feeling his cock slide further inside me. He wasn’t completely inside of me yet, so with one last gentle push back, I slid back onto him, taking all of him inside me. I could feel his hips against my arse cheeks and his balls touching against mine.

I had passed the point of no return, and it felt good. No, it felt fucking great. I let out a moan. It felt like my cock was ready to explode, I don’t think I had ever felt it pulse that hard before.

I paused as I comprehended what I had finally done. I had a cock in my arse; I had been fucked by a man. I never thought that Ashley would be my first, but nonetheless a cock was a cock, and his was a very nice one. I looked at Karen and smiled. She moved closer and was playing with her clit with one hand, while gently masturbating my cock with her other hand. Ashley was thrusting in and out, pounding his hips into my arse with every thrust. Every few thrusts he would pull out completely and thrust it back in again. This felt awesome too.

Ashley pulled out and went over to Karen, fucked her for a while before coming back to fuck me some more. He only did this a couple of times before he came inside her. I knew he wasn’t wearing a condom, but I hadn’t even considered but that he might come inside me. I wasn’t sure I wanted him to do that, so fortunately I didn’t have to make that choice.

Karen told me to roll over onto my back on the bed, so she could give me head and masturbate me. She told me she wanted me to come in her mouth and it wasn’t long before I did exactly that. She showed me my come in her mouth, on top of her tongue, then swallowed it down.

Then just like that, it was all over. My first time was in the books. I got up, got dressed and went home.

It was the one and only time that I did it with Ashley and Karen. Working together initially made things a little awkward, but we soon realised it was just sex, a bit of fun, and moved on. We all continued to drink and party together like before, but just never had sex together again.

It took me almost twelve months to find and fuck my next man. It was only because I didn’t really know how to go about finding men who wanted the same things as I did, and most importantly, a man I knew I could trust.

Since that first time I have gone ahead leaps and bounds. I learnt how to find other bisexual and gay men and have had lots of sexual encounters with them. Most are with just a single male, but several have been with multiple men. I love giving and receiving head jobs. I am happy to be a top or a bottom, I am a versatile man. I will give the guy the choice of whatever he wants to do. Most chose to be a top. If I get the choice I will go bottom every time. I love the feeling of a cock inside me; especially the feeling of warm cum being unloaded inside me. It is the best feeling.

I have a few conditions I would like a man must meet but I have one strict rule. No body hair.
I will accept a trimmed pubic area, definitely no facial or anal hair. I keep my body hair free; I shave or wax all my pubic hair off. I find that a shaved arse makes it much easier for the cock to go into the anus, and reduces the amount of lube needed, which in turn increases the sensation. I normally do not wear condoms and do not expect them to. I will though if they specifically ask for it. I am normally only a one-on-one guy, but I have had a couple threesomes though, only with guys.

One memorable threesome was a very spontaneous hook up with a gay couple one night.
They were visitors to the town, whom I met at the pub one night. After the pub closed, we went back to their cabin at the local caravan park. I got to watch them play with and fuck each other before they asked me to join them. They introduced me to being spit-roasted and I got to be a top and bottom at the same time. That was an interesting and very enjoyable night.

I have never had sex with another woman. The closest I have come was with my first encounter, with Karen and Ashley. I have had the same male for sex for a few years now. Michael is a local married man, so we both have something to lose if one of us speaks. We are not exclusive to each other, and we both still have the odd casual encounters with other men.

The sex is just awesome, but it’s just that, sex. A way of getting off. I do not consider myself gay; I just like having sex with men, I like fucking and being fucked by men. I have never had an emotional or romantic connection with any of the men I have fucked. It is purely a business arrangement, for want of a better description.

I do enjoy it very much. Sometimes I think it is better than straight sex. The best part is the thrill of meeting a new guy. It gets the adrenaline pumping, knowing I will be fucking someone new.

I will tell my wife one day, but I honestly think she already knows but chooses not to say anything. She is happy with sex once a week, so while I am leaving her alone, she's happy.

I am happy, and our relationship is awesome because of it.