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We maybe do it once every couple of months. There's nothing fun about it for me. It's not that it's painful, it's just mildly uncomfortable and really not my thing.
The guy I was seeing wanted to do it, and I was resistant but eventually gave in. He tried to put it in, but it just hurt too much.
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I don't think he used lube, and it's just really tight. Maybe I'd do it again with the right person if I had a lot of trust in him. Either way, it's not something at the top of my list.
My high school sweetheart was raised strictly Catholic and was 'saving it for marriage. His being exceedingly well-endowed made taking it slowly and using plenty of lube the obvious choice.
The oddest thing I noticed was that the initial penetration would generate a tight sensation in my throat, similar to what you might feel after a bad scare. But it was an exciting feeling, not scary at all. It's a slow but pleasantly luxurious sensation of being gently and benignly pulled inside out.
It certainly was extremely erotic, and I felt aware of my entire body as an erogenous zone. I discovered I was able to orgasm via anal penetration, and anal play is something I enjoy to this day. At one point in high school, I was having more anal than regular sex. He feels bigger than ever and completely fills you up.
That means lots of lube, starting small with a pinky finger just like in Fifty Shadesthen working your way up to small toys or butt plugs. After that, anal can be amazing! It is super-intense, and your lover has to be extremely delicate and careful and be a good listener and super patient-and you as the receiver have to have a lot of trust in that.
The anus is, after all, an exit, not an entrance, and so it could really, really hurt. This is not an act that should ever be undertaken with a random dude or at a random moment; you both have to want it, and you both have to be prepared. No assholes allowed in the asshole!
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I think that's one of the best parts of the whole ordeal. It takes so much time, trust, and communication that it just amplifies everything physical going on because you are so connected with your partner. Lots of lube, slow, gentle motions, and patience move it quickly to the next phase, which is an exciting, pleasurable pressure.
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I find that I can have stronger orgasms while being penetrated anally, but these are clitoral or vaginal orgasms, not anal orgasms-those are quite elusive. For me, it's probably the added stimulation, the intimacy, and the emotional intensity of anal that make orgasms stronger.
But if the angle is wrong in anal sex, with too much of a sharp upward or downward angle, a sting-y and unpleasant pain can be the result.
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Having the right angle of entry is important for me. Also, pegging someone with a strap-on can be very pleasurable with an insert-able double-ended dildo, or even just the harness or base of the strap-on grinding up against the clitoris.
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