My First Male Anal Orgasm

Yesterday I experienced my first male anal orgasm, it was the most intense climax of my life and I want to shout about it from the rooftops. Hence me looking for more information today on the internet, and ending up on this site. Every man should experience this, at least once. Osman writes about his first super “o”, anal orgasm

Some background first

I have enjoyed being penetrated by fingers, vibrators or dildos during oral sex and masturbation with partners for some time now. On many occasions, I have solo masturbated with dildos but have never achieved a climax, without also stimulating my cock by my hand at the same time. I read that a small percentage of men can climax purely from anal stimulation and wanted to explore this. I now believe that many or most men could achieve this if they would only:

1 Learn to explore and understand their own bodies.

2 Become less cock oriented.

3 Learn to take their time over sex.

4 Loose their fears about anal play being indicative of homosexuality and so reflecting negatively on their masculinity.

The Orgasm

I had the house to myself and so I went to bed in the early evening. My girlfriend has been away because of work for the past week, and I haven’t cum since she left. We both regularly use a variety of sex toys, so I had many to choose from. I have tried realistic dildos before and found the “veins, ridges and folds” uncomfortable, so I took the smoothest longest (easier to hold) smooth bodied soft vinyl dildo we had. It seemed very large (250mm X 45mm), and a little intimidating, but I knew that because of its size I would have to take things slowly. I covered it with a plain condom and applied most of a tube of KY to the head and shaft of the dildo; then placed a blob on my anus. To insert the dildo I lay on my left side with my knees drawn up to my chest. I relaxed and concentrated on my breathing. I took the slippery shaft in my right hand and curled my first and second fingers around the flared base end to enable me to apply a penetrating pressure. I reached around my right thigh and placed the head against my anus and pushed gently. I am used to being anally penetrated but it took several minutes for my body to adjust to the large diameter. I just lay there and relaxed, keeping the pressure on and the dildo in place.

Eventually, I breathed deeply, exhaled and pushed the dildo deeper into me. Then I rolled onto my back with my legs bent and my knees wide apart and upright. When I first inserted the dildo my cock became a little hard, as I paused to allow my anus to adjust, my cock quickly softened. After this my cock was soft for the whole session and just lay upon my belly. Not once did I stimulate or touch my cock in anyway. In fact, I forgot about my cock entirely, probably the best thing that I could have done. I began to move the dildo in and out of my body very slowly. I focused on the sensations I could feel centred about the dildo. I tried different depths, angles, and speeds of penetration and withdrawal. Several times I withdrew the dildo and reapplied lube to dildo or hole whenever I felt I needed it. I must emphasise that I used the dildo for over 30 minutes before I orgasmed. There was a very wide range of sensations, some were very pleasurable, some were just novel and different. Finally, I just seemed to settle into an easy rhythm, with the dildo moving in and out for a few inches of the centre of my body.

I noticed that as I began to enjoy the dildo more, my hips began to move like a woman’s, up to meet the penetrating thrust. This surprised me, as did the pleasure I was getting from nothing more than penetration. Then I realised that I was beginning to experience the sensations that usually precede my climax. I looked down at my cock and could see my whole cock contract and expand, the cum hole was in a series of spasms. In effect I was having a dry climax, I was still enjoying the sensations coming from the dildo and so I continued moving it in and out, but with a faster rhythm that felt right. Then I ejaculated, just a little of a clear liquid, much less than normal. The dildo still felt good, so I continued to use it. Although for a second I thought I had wet myself not cum. Then I ejaculated again with the same clear liquid, but a more usual amount. I continued to move the dildo inside me, which now felt really good. Suddenly I came again. This time, I shot a forceful stream of clear cum from my soft cock resting on my belly, up my body, across my chest and onto my shoulder. If my head had been positioned slightly differently I would probably have shot cum into my own mouth. I continued to use the dildo and climaxed in the same violent way 3 more times. Suddenly I felt tired and very satisfied. I slipped the slick, body heated dildo out of my behind and laid it on my belly alongside my soft cock. It had taken me the best part of 40 minutes, and I had cum 6 times in less than 3 minutes.


The feeling of cumming was intense and very different to a normal climax. It does take longer than a quick ‘solo stroke’, although (I hope) this may get quicker and easier with more experience. Actually, it was so good, that I’m not sure that I could handle it every day. It was very very intense. Having said that I must also say that I am very keen to experience it again, although in a slightly different form. Today I ordered a really hot leather dildo strap-on harness for my girlfriend. We both love anal, and it means we can now share the experience even more. I can’t wait to have her fuck me using the harness and a big beautiful dildo, although we may need a slightly thinner, shorter dildo if she’s in control, as I was really full and stretched.


I enjoy being anally penetrated and I was psychologically ready for this and to some extent I was physically ready also. If this is new to you, take it slow and easy. Good anal doesn’t hurt. Remember I only used about the first two-thirds of the dildo, so a shorter one should be fine, but it may be harder to grip. I don’t know if the large diameter, or the smooth surface and large rounded end helped; you’ll have to experiment yourself. I would also give the advice to put on much more lube than you think you’ll need, and to re-lube frequently. I would also advise you to relax as much as possible, forget that your cock exists, and concentrate on the sensations in your behind. It will also take time, it can’t be rushed; it could take several sessions before you can orgasm. The cum will be different, more of a clear liquid and the climax intense. Whatever you do, try this at least once, it could change your whole sex life. This must be tried to be believed. Bi/Osman

Don’t forget to tell us about your male anal orgasms bi leaving a reply below!

6 thoughts on “My First Male Anal Orgasm

  1. I recently bought a 10 inch dildo. (I have been using a rolling pin for a while). Once I’m alone on the house again I am going to try this as I want to experience this orgasm more than anything.

  2. Having read what Osman had to say about his first anal orgasm i decided to have a go myself. I took a chuch candle, lubed it up & went to shoving that thing up my ass.I got on all fours & being a spunk lover i wasn’t going to waste a single drop,so i placed a glass under my cock to catch every drop and got down to some serious ass fuckin.Just about melted that fuck off candle.Osman my man,how fuckin great does it feel when you shoot. Anyway i took that glass of cum & drank down every last drop. FanFUCKINtastic.

  3. I experienced an anal orgasm two times in my life, and I am 30 now (there’s still hope I’ll have more ?)
    My first one was when I was still in the closet, and at the time I would mostly gain sexual satisfaction from solo play or cybersex at home. I usually just played with my extremely sensitive nipples and masturbated, but as one of my regular cyber sex partners once asked for a visual of me being penetrated, I quickly looked around my room and saw a can of body spray that had a blunt bottom edge, and I thought it suitable for that purpose. I was a bit concerned about the thickness of the container, since at the time I’d never had anything of such girth penetrate me anally. In any case by the time we got there we had lots of foreplay where he simulated nipple play and I simulated fellatio. We were both very verbal and pretty much uninhibited, but one thing I never did with him during foreplay – masturbate. I would usually get so excited that my natural lubricants would pour out of my penis. By the time he is close to ejaculating from masturbating all the time, I would usually just need a few strokes to match him and we would climax together. This time he wanted to “be inside me” so I scooped the juices that leaked from my penis onto my belly and applied some to my anus and the container of body spray. As I started working it into me, I instantly felt unusual sensations that hit the tips of my penis and nipples. My natural self usually gets somewhat womanly and slutty when having sex, but this time for whatever reason it felt like I was truly a woman and I had this urge to get out from the experience bred and pregnant. Anyways, it didn’t take long before my gentle attempts at penetrating my anus and the very idea of being penetrated with such a “thick” object sent me over the edge. It caught me off guard, and I didn’t mean to ejaculate, but it just happened. It was a usual way in which I ejaculated, except that my penis did twitch and contract and expand well before the orgasm itself as well as during. My second time happened 7 or 8 years later. I met and got married to a man with a huge 8″ penis. We eventually ended up divorcing and if there’s anything I’ll miss about him it’s actually the girth of his penis (and his hairy body ?) which, as it was proportionate to his length, could fill me just enough to touch my prostate. The length itself actually turned out to be quite uncomfortable. Anyways, I was able to get myself to experience those same sensations and orgasm while on top and facing him (unfortunately as a pathological control freak that he is, at all times he had to have the lead and he’d usually just penetrate me from the back, so my joy ride was sadly a one-time experience). Now I’m on the lookout for a disproportionate penis (i.e. not too long, but thick) attached to a mentally sane and stable man (which in reality takes precedence over anything else; otherwise I would have stayed with my ex husband) who won’t mind letting loose in the process of love-making and accepting my (actually very sensitive) effeminate bedtime side.

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