Yes this is quite possible for some people. By that I mean younger men have too stiff of an erection to be able to bend it enough to get in, and some anuses are further back than others and difficult to reach. And some men have a short or thick cock that make this technique difficult. Luckily my body has several attributes that make autopederasty possible. If you look on many porn sites, search self fuck you will be able to see for yourself. But for myself, I’ve discovered a wonderful sexual union that delivers amazing pleasure and been doing it for many years now. Now you might not know but one can orgasm without having a full erection, and older men like myself don’t get as hard as they used too, and so are able to find that his semi-erect penis can bend quite easily, and if you have a long enough penis and your anus is located up closer to your balls, it is in fact quite reachable. I am average penis size by the way.
First, I clean myself out with a shower and an enema, which warms and relaxes my anus. I’ve already had some practice fingering my hole and prostate, so it welcomes pleasure and opens easily. I like to introduce some lube into my rectum first and make it easy to slide in. Then I will stroke my dick with lotion until I have a full erection and then let it soften. Repeat several times. Edging is getting close but not cumming. Once my cock is warmed up good, and in a very aroused state, it is ready to cum but not fully erect. During this time, I usually put a good amount of vaseline around the hole and use lotion to grease my shaft and head. Moving my balls to one side, I place it downward with the natural curve at the entrance of my hole. Using my fingers, I try and push the head inside using the cooperation of the anal sphincter muscle to open and close on the tip. This flexing feels good and allows the anus to relax and open enough that the head will eventually get in with some manual forcing. The cock will excite and begin to harden once the head gets in there and my anal contractions provide a stimulation that feels warm and wonderful on my cock.
After awhile, my anus relaxes further and I can push it in deeper with my middle finger and soon my shaft and head are sliding in and pleasuring my prostate gland. Using my hand I rub and handle myself to pleasure my cock on the part that is still outside and as it hardens further, a fullness arrives and I can feel the bulbous head in there. The lotion I put in there earlier does its job, allowing some better movement within. Even though my penis is curved around backwards, its still getting good blood flow and I feel fully erect now while inside and my anus is equally excited and has tightened its grip on the shaft just behind the head. I add more vaseline around the opening and really start working it in deeper and deeper, back and forth, making the fuck happen. My heart is really pounding now and my breathing rate has increased too. I am totally into it, waiting for my climax which is very controllable at this point, and I find I can prolong these wonderful feelings. I think the bend keeps me from cumming too quickly, so that’s a real plus. Sometimes I just stop and let it soften and finger around inside to feel and stimulate the head of my penis, then start pumping it up again. Wonderful sensations. from both organs at the same time. My brain is overwhelmed as my orgasm happens and I actually cum inside. My anal contractions occur as my cock pulsates and ejaculates. I help it out by milking my shaft and not pulling out too soon before my erection subsides and until the semen can get through the kink in the hose and flows into my rectum. This act has become my favorite way of masturbation and is kinda addicting because it delivers such powerful feelings of intimacy and gives me access to the sex I desire anytime I want it. I wondered for years if I was somehow damaging my penis, but so far nothing bad has been noticed, other than my cock seems to have gotten a bit larger. So I think I’ll keep on doing it, but not giving up on sexual partners either. [Source]