Top or Botton? When and why?

Setting aside for a moment those who identify as "versatile", when and why did you choose to identify as a top or bottom? I ran away from an attempted pass when I was 17 years old. But I spent the next 20 years wondering about it and during a situation similar to that time in my youth I said what the hell and accepted the pass, but as a top, and for the next decade or so I topped exclusively. Then I encountered a very powerful woman and began a faily long-lasting affair with her. She was a sexual athelete and we would fuck our brains out in every way imaginable. And then one night she told me she wanted to feminize me, and she did, and we had fun with a psuedo lesbian scene, and some weeks later she said she wanted to fuck me. And she did, with a very serious and expensive strap on, and I was hooked. Which led to me cheating on her with men, which led to our breakup, and I've been a sometimes cross-dressed but always 100 percent bottom since. I recently had the opportunity to top a woman, and while it was pleasant enough, to me at least, it doesn't compare to opening my legs and surrendering myself to a dominant man. The freedom of abandoning all responsibilities while being fucked is highly addictive.

For me, it was pretty simple. I tried the bottom a couple of times and it did nothing for me but I do love to top a nice ass that really enjoys getting fucked.

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Originally Posted by Neonaught

For me, it was pretty simple. I tried the bottom a couple of times and it did nothing for me but I do love to top a nice ass that really enjoys getting fucked.

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You sound so amazingly fun. I realized I was a bottom type only a couple years ago or more. I found myself excited about a dick and cum. I like what a dick does and responds and cums. I like the mouth full of warm rubbery cock and hearing a guy as I suck like a slut. I have been trying to find a guy that would take my ass first time. I have a smaller round girly firm ass for an older guy. Love to be submissive facing away and get dick in me like that. I just dont want to fuck a guy but maybe if younger and feminine I guess?

I have always liked being anally stimulated. After using various substitutes for cocks I wanted to experience the real thing. I asked a guy to fuck me. After the initial discomfort the pleasure took over. I knew I am not a top. I did discover that while being fucked that I wanted to be sucking cock at the same time.

I'm a Top with women, I do love a tight pussy & a nice pair of boobs. I used to be a Top with guys, but that was when i was at college. These days I usually Bottom for a hard cock sticking out of a hot guy because he can give me pleasures in areas no woman can reach, not even with a strapon dildo. The real thing always feels better.

18, the first guy I was with we were exploring, he wanted me to top him, I maybe got in 5 thrusts, he didn’t like the bit of pain or the feeling at all, so he asked me if I wanted to try bottoming, sure I was 18, high, and horny as hell. It hurt a bit at first, we had some starts and stops, add more lube, but there finally came a moment where he was in, good missionary tempo, and I was really surprised by how much I enjoyed it, he was very into it too, it really felt good to me. I came pretty hard from him jacking me, and everything else that was going on. That’s the only time I’ve topped a guy.

I have always loved ass play and being anally stimulated. Long before I ever discovered my bi side, the first time a girl touched my asshole while we were fucking I started cumming. The first time I ever fucked a girl in the ass I was hooked on anal sex and fucked most of my girlfriends in the ass after that. My cock is 7" and pretty thick so I had some girlfriends who couldn't take it in the ass.
I first started getting into guys after really getting into Tranny porn. I had fantasies about fucking and being fucked by these beautiful chicks with dicks. Well that got me chatting on bi and gay sites and hooking up with my first guy. He was a younger guy and it was his first time too.
He asked if he could wear stockings and I was all for it. I really didn't know what was going to happen but I wanted to find out. I sucked his cock first for a bit and loved the feeling of his cock in my mouth, the he sucked me for awhile and that was nice too. We decided to move to the bedroom and got into a 69 and I was loving it and wanted it to last as long as possible. Then to my surprise he asked me to fuck him.
I put on a condom and lubed us both up but when I finally got my cock about halfway in his super tight ass he said it hurt to much and wanted me to stop. Truth of the matter was that was the tightest ass I ever had my cock in and I wanted to fuck it really bad but I took it out. Then he wanted to leave and left me with a case of blue balls thinking I should have just raped his little ass.
The next guy I hooked up with saw a picture of my cock and asked me if I wanted to fuck his tight ass. He was a young fem gay guy and I fucked his tight ass real good. After that I kept hooking up with younger smooth bottoms who liked to get fucked.
I hooked up with one Asian guy once that we flipped fucked, it was ok but I enjoyed fucking him more than being fucked by him.
So I'm a top for the most part, I have fucked a lot of sexy guys over the years. The ones I have enjoyed the most are guys who can cum while getting fucked. I always love making a girl cum and that goes for guys too.

I started sucking cock about 4 years ago and bottomed for the first time last year. For me, there's a submissive aspect that I enjoy acting out in getting on my knees or bending over to accommodate another man's sexual wants and needs. I'm not attracted to men, so sex with men still feels taboo. I'm not into actual pain but I do enjoy when a man tries to force his cock down my throat, even when he's cumming, and I enjoy the discomfort I feel in my ass when a man is thrusting intensely inside me. I also feel oddly feminized when a man is thrusting inside me and when he's cumming inside me. Because of all that, I'm not interested in topping another man or being sucked off by another man.

When I first started having sex with men (age 22) I had no desire to have any kind of anal sex. I told who ever I was having sex with upfront that I was into giving and receiving hand jobs and that I really loved giving and receiving blowjobs, I would also tell them I loved sucking a man's cock and having him cum in my mouth and swallowing his cum.

Years later (age 26) when I became involved with a very good friend who was gay my attitude about anal sex began to change.. Having regular oral sex with him changed the way I felt about anal. One time he was giving me one of his always excellent blowjobs when he suddenly lifted both of my legs up in the air (I was sitting on his couch with him kneeling on the floor in front of me). He took his mouth off of my cock and started licking my asshole. I was startled but I decided to let him lick and kiss my asshole because it felt absolutely amazing. This went on for a good 30 minutes. It was pure ecstasy. and in some ways was more pleasurable than having him suck my cock. He didn't need to ask me if I liked it because my groans and squirming told him that I loved it.

After that session I started thinking about having anal sex with him. The more I thought about it the more I knew I wanted him to fuck me. Because we were friends and he knew I was an anal virgin I knew he would be gentle. I had absolutely no interest in being a top so I focused on being a bottom. Could I actually let another man fuck me? It was one thing to give a BJ or HJ to a man and have him reciprocate but letting another man put his cock in my ass was a huge step in my bi-curious experiences.

As time went by I became more comfortable with wanting to find out what it felt like to be fucked by a man. One night, after many very hot BJ/HJ sessions over the previous months I came right out and told him I wanted him to fuck me. We were both naked when I said this so he got up and came back with some lube and began preparing his very large (8-9 inches) and very thick cock to penetrate my ass. Terry had a very large mushroom cock head and I knew it might be difficult for my ass to accept his cock. He told me that it might be painful but he would be as gentle as possible. I got into the doggy position and he rubbed some of the lube on and around my asshole. I felt one, then two and finally three of his fingers enter me in an effort to loosen me up. It felt really good having his fingers in me. He then told me he was going to put his cock in me. All of a sudden I felt an excruciating pain shoot through my lower body. I immediately made him stop but I still wanted his cock in my ass so we tried again a couple of more times but I was just too tense and inexperienced to relax and let him enter me.

Many years went by and whenever I was with a man it was always just blowjobs and hand jobs, always where I had the guy cum in my mouth and I would swallow him. Then I met a gay couple on the internet and we started e-mailing each other. I told them I wanted to suck them both off and have them cum in my mouth. I also told them that if the chemistry was right they could fuck me with the condition that they would not cum in me so I could suck them both off after they were done fucking me...

Well, the chemistry was right and when one of them said "Let's have some fucking". I asked the other one if he wanted to fuck me and he said yes and I said OK and he went to get some lube. I wondered if he would also bring back condoms with him.

While he was gone, I started sucking his partners cock to get him ready to fuck me. When the other man returned to the living room with the lube he did not have condoms. They were going to bareback me. After all these years I was going to finally find out what it is like to have a cock in my ass and I was going to do it bareback.

We had exchanged pictures and I knew I could handle the size of these two men's cocks (both about six inches or so and cut) if they decided they wanted to fuck me.. I got in the doggy position and spread my legs. I wanted it to be easy for him. I felt him put his hand on my hip and his lubed cock slid right into my ass with no resistance. He wasted no time in getting into thrusting his cock into me repeatedly and after getting used to the sensation of his cock in me I started to really like the feeling of being fucked, of knowing the cock I had been sucking earlier was now in my ass.

After about 20 minutes it was time for the other man, the one who had said "Let's have some fucking" to take his turn.. I was actually attracted to this man and not just his cock. This was very rare for me. Only three times in my life was I actually attracted to the man and his cock and this was the third time. He was a tall, lean athletic man and doggy would not work for him so he had me get down on all fours and bend at the waist so that my head went down to the floor and he entered me. .

By now I was really enjoying it. I started making noises, saying "fuck me, fuck me" and moving my ass back and forth on his cock He kept fucking me for another 15 minutes or so and then he pulled out. It was time for me to suck them off and have them cum in my mouth.

This was my first and only time in all male threesome so I was really excited about getting to suck two cocks off and swallow their cum in one night.. The first guy who fucked me said he wasn't ready yet so I told the second man I would do him first. I really like to suck cock, taking my time and exploring the man's cock and balls, finding the more sensitive spots on both when I give a blowjob. I give a really long and sensuous BJ and while I was sucking this guy off it struck me that we had gone straight from him fucking me to me taking his cock into my mouth and that this was my first ass to mouth blowjob. It wasn't long before he was cumming in my mouth with me savoring his cum, the texture and the taste. After I took my mouth off his cock I squeezed his cock and a large droplet of cum appeared on the slit at the end of his cock. I put my mouth around his cock and sucked all the cum that had not already cum out. I then did his friend and got my second load of sweet cum to swallow..

In my case, just as I was beginning to explore sexually, I developed a pretty severe case of ED. I tried a variety of things for a while, but eventually came to realize that I liked bottom things. It’s remained my focus to this day.