Busting cherries 101
How are you? I am Vince, and I just have a question (or should I say, “I need you advice?”). My boyfriend and I have been together for three years now. But the thing is, we haven’t had anal sex! Ever! Our physical intimacy is limited to oral. We finally decided to give fucking a try, but our problem is that we never had anything in our butts! As seen from gay porn, the models seem to do it (the penetration) quite easily. We are afraid that we might hurt our anatomy down there. Do you have any suggestions how we can prepare for our first session? We really want to make it memorable and enjoyable for both of us.
Hope to hear from you soon.
Thank you very much.
For your first anal session to go well, you should first look at the process for preparing to be the receptive partner. I wrote an entry about this that you can read by clicking here. That will take care of the internal hygiene, but here are what I consider to be the three important ingredients once you’ve prepped: 1) patience/sensitivity, 2) lube, 3) condoms.
I don’t want to scare you, and I hope you will see the humor in this, but I once saw a bumper sticker that said, “It only hurts the first 19 times.” Anal sex is INTENSE. I don’t suggest you both trying to be penetrated the same day. If you both want to experiment with being fucked, I suggest doing it on separate days. I say this, because whoever is getting penetrated is going to need a lot of time. You will need your boyfriend to go extraordinarily slow. Seriously: Every centimeter will feel like a foot at first. Even with relaxation, love, curiosity, and lust goading you on, you will need several minutes just to get him inside you (and then you’ll probably want him to be completely still for a while as you relax more deeply). To ease this process, he should first very thoroughly eat your ass for an extended amount of time, then gently and gradually finger fuck you with one finger and then two (keep the fingernails clipped short and with smooth edges, so the nails don’t tear your delicates!). Once you have relaxed a bit you can graduate up to getting the tip of his cock in; however, his prick is going to feel 10 times fatter than his fingers, so go slow!
Second, you can never have enough lube when you’re beginning. Well, yes, you can, but it won’t seem like it at first. As you get more experienced you will do more with less; however, at first you will want to keep your boyfriend freshly slicked up (and given how slowly he’ll be pushing into you, it’s okay to expect him to freshen the lube a little with each little nudge deeper inside you). It will be intense, but if you can you need to let him move inside you a little to maintain his erection. If he sits too still for too long with your bear trap clamping down on him in a death grip, he will probably deflate and all this will be for naught.
Lastly, you should use condoms. I know you’ve been with him for a while, but one of the most common ways of getting HIV is from “monogamous partners.” If you reject this emotionally or intellectually, or if your spirit is somehow reviled at the thought of not trusting your boyfriend, then consider this alternative, which will keep his dick naked and free to move about without restriction: Female condoms are pushed inside you by your partner’s penis, then stay in place as he moves in and out of you. It won’t look very cute with the opening of the condom hanging out of your booty, but it provides protection while not sheathing your boyfriend’s cock in a standard male condom (which may kill his erection if he’s never felt the type of squeezing condoms tend to apply at the base of the penis).
So, set aside at least a few hours of play time, get a brand new bottle of lube, keep the protection handy, and have a good time!