Anonymous: I’m a girl who’s never masturbated or played with my clit much, I like the idea of sex being more about mutual pleasure and it just seems selfish to rub my clit and makes me feel bad. I’ve been reading your blog for a while and I want to go anal only, and my boyfriend is on board, but I need to train my ass before I can do it every day. We do it sometimes together but I need to do it more often than he has time for. How can I get past the feeling of it being masturbation so I can do it more?

Inherently there’s nothing wrong with masturbation, but I’ve known a number of women who have a similar perspective as your own, and as long as you’re happy and it’s what you want, there’s nothing wrong with avoiding it either, especially if you have a healthy sex life.

I’ve also talked with other women in similar scenarios, where they or their partner wants to be anal only but struggle with pain/discomfort from doing it too frequently and need more practice, but don’t want to masturbate and so end up in a somewhat frustrating cycle.

I’d suggest considering it as not being something selfish because you’re preparing and training yourself for a mutually pleasurable anal only future together. Make your boyfriend a part of it as often as you can, but think of your solo anal masturbation time as anal training for when you are together, and I think it will come a lot easier to you and you’ll be able and eager to go anal only sooner than you think.

Anonymous: How should I go about beginning anal play? I’m worried about the hygiene and the comfort and I feel like that will make me too tense to enjoy it. Advice?

Try it while taking a shower after having gone to the bathroom already. Lubricate a finger and gently insert it. Massage around the outside for a few minutes first if you feel tense until you relax a bit. If it hurts, stop and try again another time. If it’s dirty, just wash off in the shower.

Anonymous: do you have any tips for somebody who wants to try anal for the first time (by themself)? I’ve been curious about it but have been too nervous to find some info about it ;;

I do! That advice, in short summary form, is: start small, go slow, use lube, and practice frequently.

Start by just massaging the outside of your asshole with a lubricated finger, running it in circles around and across. As you start to relax and get into how it feels, slide a finger inside. If something hurts, go back a step and try again in a few minutes, repeating as needed until you can do it without it hurting. Once one finger feels great and you’re ready to move in, try adding a second finger. Keep repeating this process of slow increases in size up to 3 or 4 fingers, then get a butt plug and dildo or two to try with too. Always use lube.

Simply doing this on occasion, however, won’t really help in the long term. If after the first time or two you enjoy how it feels and want more, I’d suggest making it a regular part of your masturbation routine, which both helps really start to unlock the pleasure of anal, and helps with anal training so you can advance to bigger and better things going forward.

Hi, it’s the girl you tagged 20180705 again, I didn’t answer for two weeks because my boyfriend and I were on vacation. I thought a lot during those vacations (and we fucked a lot, too), and I realized my main issue right now is less about my pleasure (which I was worried about first) than about pleasing my boyfriend. Learning that he spent four years taking care about my vagina and clitoris even though he hated them shocked me even more than I thought it did initially (and that was a LOT).

Both to regain my pride as a woman and to reward his dedication, I realize I sort of feel like I must repay him with at least four years of anal sex only, to make him feel good, and to simply see if it works for me. In fact, to me, it’s like I let him down, and I’m looking to seduce him again. I know it may seems like I’m submitting to him (but hey, he did submit to me all those years), but to me, it’s the opposite, learning how to turn him on and make him crazy with lust for me is empowerment.

I think people will get that sort of impression of submission to him at the expense of what you want, but ultimately it sounds like that’s not how you see it and in fact are enjoying this change. And even if it were a form of submission, there’s nothing wrong with submission so long as it’s your choice and gives you what you ultimately need. (And sometimes what some people need is denial of their own desires and a focus on pleasing their partner instead. There’s nothing wrong with that dynamic if it’s what works for you.)

Does this make sense to you? To that end, I’m still “exercising” my ass in secret with my “almost my boyfriend’s” dildo, wearing lingerie a lot more often, taking attitudes and poses during sex that STRONGLY suggest I’m craving anal sex, I’m more verbal during sex, I’m entirely ignoring my vagina and pussy (including in private while I “exercise”, like you and my gay friend suggested), and I even fingered my ass then licked my fingers in front of my boyfriend, which turned him crazy.

Sounds like you’ve gotten your routine down and pretty well figured out. Acting like you love and crave and need anal, both to him and to yourself, has the added benefit of ultimately making you love and crave and need it for yourself, so that’s really a good way to sort of “retrain” your own thinking about it too.

I also never fail to compliment him after sex, which isn’t very hard for me, because like my friend foretold, the more I do all those things, the better he gets as a lover: more passionate, tender, harder, hotter, more creative, etc. He’s also more assertive in general, even outside of sex, which is very rewarding to me. The only thing is, before, he always waited for me to have an orgasm before ending sex, and now, he basically stops after he cums, like my orgasms are irrelevant.

I’m not sure why exactly. In fact, since we’ve had “that talk” more than three months ago, I haven’t had a single orgasm, which started to weigh heavily on me. The last times we’ve had sex (lately it’s generally more than once per day, before “that talk” it was about three times a week) I felt really close to come, and I may have caused it by touching my clitoris, but I avoided it both because it felt wrong, and because I actually wanted my ass fucked harder instead, which felt weird.

Even weirder, even though I felt close to orgasm those last few times and our sex stopped abruptly because he suddenly came into my ass, it didn’t feel frustrating, rather, strangely rewarding. Also, it sort of felt hot and made me look forward our next intercourse, which was oddly satisfying. I think I sort of like the idea of my boyfriend not “bothering” with me: he faked pleasure for four years, so I enjoy when it’s obvious he’s just having his own fun and not making any sort of effort.

It can take some time for a lot of women to get to where anal orgasms are a regular thing for them, especially with a lifetime of vaginal/clitoral stimulation to overcome. It can get frustrating to not orgasm for that long, but that frustration and arousal can ultimately help to make sex a lot better, and over time further develop anal stimulation into your primary source of pleasure and ultimately an outlet for orgasm as well. It sounds like it’s become less of a priority for you to desperately seek orgasm, which helps as well—trying constantly for it rather than just enjoying anal for what it is can keep you from getting there, which seems kind of counterintuitive, but orgasms are weird that way. It sounds like you’re gradually getting to the point that some anal only women find themselves at, where in time they enjoy not orgasming and enjoy the constant pleasure and anal stimulation and denial more than an orgasm, and get satisfaction out of pleasing their partner more than their own release.

So long as you are happy with the arrangement, even with its challenges for you, and are willing to go forward with it, I see no problem with that. Just remember that even if you’re consenting to it now, if ultimately this dynamic doesn’t work for you and you need it to change, that’s absolutely your right.

The original version of this post on Tumblr received the following response.

debaucherycat: This inspires me so much. I’m almost envious. And horrified at the same time.

It took me ages to find courage and ask my man to take control of my orgasms. Our current arrangement is that I get to cum on Saturdays, if I collect my „cum points“ over a week. I get them by giving pleasure to him and edging mostly. And when the day comes, he grants me an orgasm. If I’ve earned it. And if he is in the mood. And sometimes he just isn’t. Which adds a lovely twist to it. Along with me being anal only. Basically, he gets to fuck my ass or my mouth whenever he likes. And I get to edge and hope for the best.

But reading the story of that girl, who abandoned all of her pleasure for her boyfriend… Well, let’s just say, it gives me ideas. And that’s terrifying. Not so long ago orgasm denial was only an arousing idea. Something I liked to fantasize about. And now I’m living it.

Abandoning my clit for good is an arousing idea too. Maybe even more so…

I’m so fucked.

Anonymous: How Deep?? I watch videos with super long dildos that don’t seem to have any problem getting past the colon. When my wife pegs me, I can only take 6″ before it hurts to much to go deeper. Can you injure yourself going deeper? She can take all of me about 7″ but its uncomfortable when all the way in. I can take a large butt plug so girth is not an issue. What advice do you have for us. We both want to have deeper anal play. We LOVE your blog!! You have inspired us to go AO and we love it.

For the majority of people, anal sex takes place within the rectum. To go deeper than the rectum requires going past a bend into the sigmoid colon. Trying to push something straight or rigid past that point will result in pain and could cause injury if not properly prepared for it.

To do deeper play, use a long and flexible dildo. The 18″ double-ended dildos are a good option for this. It shouldn’t be terribly thick to begin with. Slide it in as deep as it comfortably will go, and then try adjusting its angle and rotating it gently while applying pressure—not enough for it to hurt, but enough to feel the pressure. Eventually you should feel it pop through the bend. With practice, you can do this to straighten out that bend temporarily through warming up with a smaller and more flexible dildo and then work up to something bigger and/or more stiff.

As with any new anal frontier, go slow, take your time, listen to your body, avoid anything that hurts significantly, and stop and take a break for a day or two if you experience any signs of injury.

Anonymous: I’m interested. Problem is I don’t have any toys, and no boyfriend. What should i use as a makeshift dildo for now?

Start with just your fingers. Add some lube, massage around your anus with a finger, rubbing across it and around it in circles, let yourself get into it and relax. As it starts to want to open up a bit more, slide one of your fingers inside and move it in and out a bit. Keep adding another finger as you feel yourself relaxing further and wanting more. If something hurts, go back down in size again. It might take multiple play sessions to go up in size. Listen to your body and go at a pace that works for you. Once you can fit three or four fingers with relative ease, then you would be ready for something more.

A cucumber and similar vegetables can make for a reasonable makeshift dildo if you don’t have anything better available. Wash it and make sure it doesn’t have any sharp points on it before trying, and if you have a condom available, try putting that over it as well. Some make do with small bottles as well. But real dildos and butt plugs are best, as they’re designed to go in your ass, so I would recommend getting some.

Good luck!

anal-princess-plugged: I’ve been trying to get into regular anal sex and wearing a plug as often as possible since last November. Despite all the training I’ve done, I still get digestive issues (constipation, gas, bloating) and have to stop anal play for a while before I can comfortably get back into it. I really want to be able to always do anal and wear my plug most of the time. Any advice for helping my body adjust to regular anal sex?

I’d say to keep an eye out on whether there are any dietary factors that may effect your digestion in those ways more than others and adjust as needed to try and optimize things. A generally balanced diet with a healthy amount of dietary fiber is a good baseline for anal usually, though some may need to adjust further if they have any particular food intolerances, etc. that can cause increased gas or bloating.

You may also want to try some different types of lube—some lube can cause different reactions in different people, and if you’ve primarily stuck to a particular type, trying a few different ones might be a good idea.

Beyond that, I’d suggest not starting with the goal of plugging as often as possible right away. Instead, try it for a smaller period of time each day—maybe an hour a day for the first week?—and if you’re comfortable with that, bump it up a bit, and keep going from there. If you find a point where it starts getting uncomfortable to maintain, try sticking with a shorter length of time per day for a bit longer or split it up across the day a bit more before trying again. Your body needs time to adjust to the new change and suddenly being plugged all the time can cause things to get a bit out of whack and cause discomfort, etc.

Hope that helps a little bit or gives you some ideas to try and that with time you’ll be able to plug and have anal sex regularly!

Anonymous: I want to try anal, it’s been a fantasy of mine for awhile…but I don’t have anyone I could ask. Have any advice for training myself?

There was a recent post on this very subject, so I’d suggest you check this out first as well as looking at the Anal Advice category! If you have any other specific followup questions, please feel free to ask!

Anonymous: It’s crazy how training on a daily basis makes a huge difference and help you progress, I moved up two sizes in the span of four days( the bigger one is still kinda uncomfortable but the good kind of uncomfortable). Moral of the story : train daily for the best and quickest results

Absolutely! If you’re struggling with anal, making anal play/training into a daily routine—especially just making it into a normal part of your masturbation routine (or replacing your masturbation routine with anal play if working towards being fully anal only)—is one of the best things you can do, and it’s amazing how quickly you can get into it and master anal once you’ve done so.

Anonymous: Can you give me a step by step guide to help get my partner into anal. We have all the toys and I’ve tried getting her to wear them but she’s very vanilla

There’s no one-size-fits-all answer.

In general, start small and focus on her pleasure and enjoyment of it, without rushing things. Try rimming her, and massaging her anus externally with a lubricated finger. If she enjoys these things, incorporate them into your regular and frequent routine together. Over time, move on to fingering her ass too, both on its own and during other stimulation she enjoys. Work up slowly from there, with fingers and the toys you’ve gotten, until she can comfortably fit something penis-sized, and enjoys the sensation.

Always keep communicating, express to her how much you love her ass and how sexy it is and how much you like playing with it and pleasuring it and how you want to focus on her enjoying it too, and if you stick with what she enjoys and keep gradually expanding that, I’m sure you’ll be able to get to where she’s eager to not only keep doing it, she’ll probably want to have anal sex with you as well.