
Originally Posted by
RisingBi
I agree with into_it_all: buy yourself a slim dildo, even the slimmest one you can find, with a pointy cockhead instead of a round, bulbous one. Lie in bed and imagine it's a real man's cock, and begin slowly making love to it with your lips, tongue, mouth, and eventually throat. Maybe while you're sucking it, put a ton of saliva in your hand, and reach around and put it on your asshole, and spread it around your opening, imagining it's another guy licking your asshole with a hunger like you've never seen before. You can imagine that you are in a 69 and sucking his cock while he's rimming you, or imagine you're with two guys, sucking one, with the other rimming you.
Keep putting huge amounts of saliva into your hand and putting it back there. Then you can begin to push your index finger against your outer sphincter, feeling the excitement of even the tiniest bit of penetration from another man, even though he's just using his fingertip so far. You can switch around and lay on your back on the bed, and if you wish you can keep shoving that dildo cock in your mouth, or just focus on your asshole. Add tons of more saliva down there, rubbing it all over your beautiful asshole opening. Totally super relax your asshole as you push a little bit more of your index finger inside. Relaxation of your sphincter is entirely key. Begin moving your finger deeper and deeper, pulling out almost all the way, before pushing deeper, and repeat.
Finally you may have your entire finger deep inside you. Maybe it's on a different day, it doesn't matter. Keep working it, with lots and lots of saliva, or if you really want, you can also go for lube. I personally have been training myself with my own saliva, because I find it more sexy. Begin to fuck yourself with your finger, pulling it almost out, and then all the way in, out and in, really fucking yourself. Enjoying the feeling. It's actually a wonderful feeling! Eventually get two fingers in there all the way, and begin to fuck yourself with them, imagining your lover is fingerfucking you, opening you up for his cock.
Then you can finally move up to involving your dildo cock. Get on your hands and knees in bed, and go to town sucking that beautiful penis. Use lots and lots of saliva, and get it really soaking wet. Meanwhile, also add even more saliva to your asshole, getting it soaking wet even more. Then you are ready. Shimmy your body over on top of "his" cock, and lower yourself down until the cockhead is touching the outside of your opening. Move it around and around, rubbing the head against your opening, imagining that's what you're doing to the man underneath you. Insert your asshole down over top of that head, and very very gently push it a little bit inside of yourself. You're going to feel resistance. It's going to feel weird. If the resistance seems to be too much, and it's just not going anywhere, again, relax relax relax, and maybe even push out like you're trying to push while going to the bathroom while a bit constipated. I know it sounds contrary to what you're trying to accomplish, but pushing a little out opens up your sphincter a little to allow his rubber cock to enter.
And as you lower a little bit more, you're going to start feeling a little bit of pain. The key here is to really focus all of your mind in relaxing that sphincter. And also don't let your mind believe it's bad pain and needs to be stopped. It's normal pain. You're not damaging your sphincter and asshole in any way by doing this. It's just part of the process of anal intercourse, so you just have to very gently work your way through the pain, until eventually it's gone entirely. From what I read from bottoms, 99.9% of the time the pain eventually goes away after a cock is deep in you and he begins to fuck you, and that's been my own experience fucking my dildos.
Pull up a little, and gently go a little lower, relax relax relax, letting it just move deeper, and imagine you're giving yourself to another man, you are sitting your ass down on top of his cock, you are pushing his cock inside of you, little by little, inside YOUR ass, an ass that was meant to be filled with another man's cock. Maybe it will take more than one session to get there. But I promise you, eventually you'll have that entire "penis" inside your ass. It will definitely feel weird. It will certainly feel filled. But remember that it's a wonderful filled. Imagine it's another man's cock filling you completely. It's what you've wanted for so long. It's training for the real thing.
And then you can slowly begin to move up and down on his cock, slowly fucking you're man in the cowgirl position. I personally found this position to be best to take my dildo virginity. I also have loved it ever since, because I can hold the dildo at the base with one hand, against my bedspread, and balance myself with the other hand, and begin to ride and fuck it. Eventually I find that perfect position where the "cock" hits my prostate as I'm fucking myself. The feeling is out of this world. It almost feels like you need to pee, or something else. It's a weird feeling, but an amazing feeling as you begin to continue. And so you can begin to massage your prostate gland through your fucking motions. I have given myself a number of hands-free prostate orgasms this way. Trust me, when you have your first prostate orgasm, tons of pre-cum and then eventually full on blasts of your semen will shoot out of your cock, in an orgasm like you've never had before. It is out of this world!
Then you can go out and buy a slightly bigger dildo, and suck and fuck that, getting used to its size. I am now up to an 8 inch, relatively thick dildo cock, which is why I am now so ready for a real man. My profiles on gay hookup sites now express that desire that I'm very eager to lose my bottom virginity. And I know that now, more than ever, because my ex-girlfriend, whom I broke up with just before the pandemic hit, loved the dominance feeling she got by pegging me, mounting my ass with her 8 inch strap on dildo, and fucking me like crazy. But all I was thinking about each time while she was fucking my ass was how I wished this was a real guy with a real man-cock fucking me. I know it's going to happen, and hopefully soon.
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