I have only ever orgasmed once during anal, i.e. ejaculated, and I was on my own masturbating anally. That said, I can have multiple ‘analgasms’ during anal sex that are not related to the prostate being stimulated. They are from my rectal muscles being stimulated by a penis or a dildo. This stimulation causes contractions of the rectal walls, sometimes a ‘fluttering’ of the muscles, which creates an intense feeling of pleasure. I’d imagine that it is similar to a vaginal orgasm, in that it takes time to build up and feels like it goes through your entire body, passes, then builds up again. When I have had the first analgasm more quickly follow, with shorter times between each.

If my lover is particularly large in length and hits my second sphincter I analgasm easily. This causes my muscles to clench and have contractions on the shaft of the penis, often causing a simultaneous orgasm, which is very satisfying. Penis size is not important, though average size and up is the basic requirement. A tiny penis will not get me off, though I am just as happy taking a small cock as I am with a larger one.

I had one lover, a Brazilian, who made me analgasm every time we had anal sex. Initially our relationship, for want of a better word, consisted of me sucking him off. He had a beautiful uncut penis, nearly 8 inches long with a good girth. We hooked up at a pub over some beers, me after work as my male self. He asked if I was bi, and would I like some action. I sculled my beer and we went to his place, almost next door.

 He was nervous, I told him to relax, let me do all the work. He sat down in his seat and pulled his cock out, and I got down on my knees and started to blow him. He cursed as I started to fellate him, and soon his sweet precum was flowing. He didn’t last long, I guess he hadn’t been sucked off in some time. I swallowed his big load and ran my thumb along the underside of his penis to get every last drop out of him. We talked for a while, he wanted to know why it felt so good, better than any blowjob he had ever gotten from a woman. I said that I was totally into sucking cock. I asked if he would like me to suck him off again, he nodded and pulled his cock out of his shorts again, already stiff. I told him to stand up, and tugged his shorts down. I kissed and licked the frenulum, then slowly worked my way down his shaft. I sucked on his large, pendulus balls. Then I worked my way back up his shaft, and started sucking on his glans as I stroked him. He lasted a bit longer this time, and his load was a bit smaller. I thank him and left.

So this continued on for a while, though he had some reservations due to his upbringing. I had dabbled in crossdressing before, and wondered if this would put him at ease. I put a blonde bobbed wig in my bag, and when I got to his place I put it on as I started to suck him. This created an instant change, when he looked down he saw a ‘feminine’ head. He had never touched me before, now he was stroking my hair and pushing me down onto his cock. He came hard and I swallowed and left.

Next time I saw him I had a crotchless bodystocking on under my office clothes. I had shaved my body hair off, and before leaving work, gave myself an enema and put some lubricant inside me. I had been horny all day, now I felt pangs of desire deep in my rectum. I met him at the pub, and we had a couple of drinks, this put him more at ease. We went around to his place and went into the bedroom. I put on the wig, and for the first time, starting to undress. He sat on the edge of the bed and looked at me. I lent down and kissed him, he responded and kissed me passionately. I undid his shirt and stroked his chest as I sucked on his nipples. He stood up and finished undressing and we got on the bed. I sucked him, my desire to have him deep inside me was going wild. I stop sucking and stroking his shaft, asked if he wanted to make love to me. He said yes, so I quickly got into the doggy position and he got behind me. He fingered my hole, and remarked how ‘wet’ I was. Then I felt his glans pressing against my sphincter, I pushed back and he slid into my rectum. I backed onto until I had him inside me down to the balls. As he fucked me I clenched my rectal muscles on his out stroke. It wasn’t long before the first analgasm hit, my ass-pussy gripping his shaft as he moaned with pleasure. On the in stroke I relaxed my muscles so that he could thrust his entire length into me, hitting a spot deep inside me that sent me into estacy. I was literally biting the pillow with intense pleasure. I kept cumming and he sped up, I came at the same time as he did, his fingers digging into my hips as his cock swelled and pulsed as he pumped his spunk deep in my rectum. He slowly pulled out and I tightened my ring muscle and milked every last drop of semen out of him. I turned around and took his still stiff member in my mouth and sucked him clean. I lay on the bed and for the first time he held me, telling me how much better my arsehole was compared with pussy. He said sex with me was amazing and that he could tell when I was cumming. I told him that his cock made me assgasm easily, and I loved feeling him inside me, feeling his foreskin roll as he plunged into my love tunnel. He dozed off, still holding me. I felt his love juices deep inside me, a warm spreading feeling. I was determined to keep them inside me.

When he woke he asked to make love to me again, his erection pressing against my buttocks. I reached back and grabbed his shaft and guided him into my hole. I turned my head and we kissed as he fucked me on my side. Pulling out of my now gaping hole, I sucked him, savouring the decedent flavour of cum and anal juices. I lay back and opened my legs and he pushed his cock inside me. He fucked me hard and I bit him as I came, then his breathing sped up as did his thrusts, and once again he deposited his ball juice deep in my guts. As he pulled out and lay next to me I could feel his warm spunk deep inside me. I clenched my ring hole to hold his essence inside me, and as I did I decided this was my new path in life.

Next time I would wear makeup and experiment with different lingerie. I kept my body smooth and hairless. When I saw him next I had a small case with me, this contained makeup, different wigs and more lingerie (though crotchless bodystockings are a personal favourite of mine). He would wait and see what I was wearing, and what hair colour and length I’d choose. The makeup made me look feminine and appealing and he enjoyed making love with me.

Eventually he moved on, though his legacy was my entry into cross dressing and how to seduce men. Soon I was frequenting bars dressed as a woman. Some nights I had multiple lovers, often a quick fuck in a park or down an alleyway. Some led to regular encounters with one or more men. My ability to analgasm easily and quickly was my drawcard, many had said that they had never had anal sex than with my pulsating ass-pussy. And to this day I love milking men’s cocks and making them cum inside me.