dumbandpretty: A fellow mom, whom I’ve gotten close to the last little while, asked me how I keep B interested in sex.

I said one word:

Anal.

She said “oh” and that was the end of that. I am optimistic, however, because it was more a curious “oh” than a disgusted or disappointed “oh.” I will update you guys when I speak to her again this weekend.

Anonymous: Confession: to train myself into an anal slut, I’ve started inducing pain on my clit, like clamping it and leaving the clamps there for a long time… to learn that my clit is something filthy and unpleasant and awful. Anal is where the pleasure is.

I definitely encourage people to experiment with clitoral denial once they’ve become familiar and comfortable with enjoying anal. Not everyone needs it at all, but many can benefit from clitoral play during their initial introduction to anal. After the initial stage and when you can regularly enjoy anal, it can be beneficial to experiment with enjoying anal stimulation entirely on its own and learning more about its subtleties without the distraction of clitoral. Not everyone will decide it’s for them, and that’s okay, but some will find they love the experience of pure anal, uninfluenced by clitoral stimulation alongside and over the top of it.

Anonymous: How do you prepare for anal? It frightens me to think that something big would force in there.

You don’t force anything in, to begin with. You start with something small and lubricated (always lubricated) that you can fit in comfortably (like a finger), and you combine gently inserting that with rubbing your clit or using a vibrator. You masturbate like that often, trying to orgasm while something is in your ass. As you become more comfortable with that, you try something a little larger (maybe two fingers) and repeat. After you can fit around the size of three fingers in without difficulty, buy a small/medium buttplug (something around the size of the Tantus Ryder) and work towards being able to insert that easily and wear it during masturbation or sex and even other times as well.

Continue gradually increasing in size until you feel comfortable trying with a trusted partner who will take care to go slowly at first and let you adjust and get used to his size. If anything hurts, take a break and do more warmup with something smaller.

Anonymous: I’m so glad to hear chastity piercings are something the two of you are now considering. I think you’d be a perfect candidate for them, and even though I know you don’t need them to stay devoted to anal only at this point, they would provide lovely symbolism.

dumbandpretty: I know, right? I’ve had all the kids I want to have, my vagina has served its purpose. I think forced retirement is in order!

Anonymous: So bored with vaginal to be quite honest. If I don’t get the back door enough from my girlfriend and another girl offers it should I take it?

Don’t cheat on your girlfriend, that’s never okay. If you’re unsatisfied with your relationship, either try to improve things or do her the favor of officially breaking things off before doing anything with another partner. You’ll have to decide how important anal is to you, and whether not having it as much as you want outweighs everything else you have with your girlfriend. Sex isn’t everything in a relationship, even though it is an important component.

Anonymous: I have had anal before, but my boyfriend hasn’t. I really enjoyed it and want to have anal with my boyfriend. I’ve mentioned it before and he said he wanted to try it. He’s never tried it or said anything about it though. Is he maybe waiting to see if I bring it up again? How do I bring it up to him? I enjoy vaginal sex with him, but I want his dick in my asshole. Any advice?

Most guys want to try anal if they haven’t already, if only out of curiosity. Many, however, are also sensitive to the myth that women don’t like anal and so may have a hangup about doing it if they think it’s going to hurt their partner or she won’t enjoy it. Since you brought it up, he probably does want to do it but may not want to appear too eager or selfish for bring it up again himself now. I would mention it again, and be sure to reinforce it with the fact that you really enjoy anal and want to share it with him.

You could also take the more direct approach and prepare yourself for anal before having sex sometime and asking him partway through to put it in your (pre-warmed up and -lubed) ass.

allstrawberry: every time i see porn with something in a vagina, my brain goes “that would be better if it was in her asshole”

Anonymous: Hi! Me and my boyfriend have been trying anal recently and it has been incredible, but last time it started out really good but then it started feeling uncomfortable. When I went to the bathroom to wipe up, I noticed some very, very faint blood on the tissue and it was just a little spot. Is this normal, or something I should be concerned about?

It’s not abnormal while starting to have anal for the first time, and it’s not generally serious, but it is a sign that you may have been doing a little too much too fast without enough warmup or practice. Once it starts to become uncomfortable or you notice blood, I recommend always stopping and reassessing. If there’s blood, stop immediately and wait a few days (or until any pain is gone) before trying again, just to make sure it heals well. Very few injuries from regular anal sex are serious on their own, but they can get aggravated and harder to heal if you continue stressing them by pressing on through the pain or continuing to have anal sex before they’ve healed. A tiny spot of blood is likely just a minor abrasion/tear that will heal in a few days, however, and I wouldn’t worry about it.

Do make sure that you’re both using enough lube and engaging in enough warmup before sex. Wearing a butt plug for half an hour or so before sex can really help with getting relaxed and warmed up, but fingering can as well. Sometimes you can seemingly do everything right but still—especially when relatively new to anal—notice a little spot of blood here or there. When that happens, just take a little break from anal and try again in a few days.

Anonymous: I tried anal for the first time yesterday, and loved it! so much, we did it a second time. it’s definitely going to become a regular thing now. and who knows, eventually I might try anal only for a bit

Congratulations! Anal can be a lot of fun. Have fun with it, explore it further, discover your limits, and once you’ve really gotten familiar with it over a period of time, then consider trying anal only for a while.

While it certainly works for some to go anal only with little experience—for example, those who do so while still vaginal virgins—in general I recommend more of an easing into it just because anal can require a little more care, practice and patience at first for the best results for everyone, so if you have the opportunity to do so, learning to love anal and discovering its nuances without any obligation to have it every time just yet is my recommendation to most, then if you still really love it down the road, try a month of anal only.

That’s not to say that’s the only way to go about it, though—some people just really want to try going anal only, and if someone is motivated to do that, it can work for them!

thedirtycode: What was your first anal experience?

sweetcumkitten: I was really horny one night in my room that I was rubbing my pussy against my big fluffy stuffed bear. Grinding and felt it rubbing against my ass which made me go nuts. Got some cream and started fingering it. I enjoyed out so much I went and got a toy. Prefer anal sex over my pussy fucked. ?