Anonymous: Hi. I’m a 20yo French man, and I’m with my beautiful, lovely girlfriend since more than two months (sorry for my english). I love anal sex so much, and always loved it, but she can’t cum by being fucked anally. And I would like to make her cum this way, and “convert” her to anal only, cus I love it so freaking much, but she just like “appreciate” it, she’s doing it for my pleasure and I don’t like it.. How could I do ?

Does she actually enjoy anal and just not cum from it directly? A lot of women can’t cum from just anal (just as most can’t cum from just vaginal) but still love and enjoy it, so those are two separate issues. If she doesn’t really enjoy it and is just doing it for your pleasure, it sounds like you need to work together to help her really enjoy it and work towards making her cum frequently while receiving anal penetration, rather than the more difficult initial goal of cumming from anal penetration. Finger her ass or use a butt plug on her while eating her pussy or rubbing her clit. Use a vibrator on her during anal sex. And so on. Clit denial can be a lot of fun and great for a lot of people, but you’ve got to already enjoy anal on its own before you can really try that, and the most common way to do that is to associate anal with existing sources of pleasure—the clit being the obvious answer.

The original poster responded:

Wow, you answered pretty fast! 🙂 It’s not that she dislik anal sex, but just enjoy it a little bit. And i try to touch or finger her ass while we’re having “normal” sex, but most of time she doesn’t want, cus she’s always scared by being dirty… And i don”t want to force her at anything, i want her to enjoy it as much as i do. I love her, and her pleasure is my pleasure.

So it sounds like she does enjoy it but there’s a phobia about its cleanliness which interferes with her full enjoyment sometimes. The fact is that unless she has to go to the bathroom right then, her rectum is generally going to be empty and quite clean, especially if she has a balanced diet with a healthy amount of fiber. Perhaps through positive reinforcement and talking about how much you love her ass and how much it turns you on to play with her ass and talking with her about her fears of cleanliness you can gradually open her up to… letting you open her up, as it were.

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

disobedient-kitkat: Please don’t force her. I’m so so glad you aren’t pushing her. I suffer from cleanliness ocd, and i figure the only way I can engage comfortably in anal play is if there is a barrier between the finger/penis and the rectum, such as a glove or condom. Toys or objects used for ass play I would also avoid using orally. Its obviously no where near ideal, and I wish I wouldn’t have to worry about such things, but maybe talk to her about options like this…? Even if my rectum is clean and I’ve used an enema for extra certainty, I’m unable to avoid this paranoia. If she’s similar then maybe she has some loopholes like I mentioned that might work for you guys.

Anonymous: Hi I’m a guy who have a relationship with a girl for more than 3 year. When we start dating she never tried anal before so I tried anal with her and she liked so much. There was a lot of anal sex even anal only weeks. we move together about 5 months since then she don’t want to have anal anymore even don’t let me touch her ass. I really want to break with her what should I do?

Talk to her. Ask her why she doesn’t want to have anything to do with anal anymore when she seemed to really enjoy it at first. Communication is usually the first and most important step in any of these situations.

Anonymous: Anal Only September girl going to class wearing a butt plug for the first time today (because I crave my ass filled all the time these days…)! How exciting… should make a boring lecture far more entertaining!

That’s great! Hope it went well! I think you’ll find that craving will grow even more the more you plug your ass—fortunately, it’s a craving that’s easily satisfied and far better for you than many cravings!

Anonymous: Hi, i’m a virgin, because was saving myself till marriage. I’m already 38 years old and still single. I start to hate myself the world and etc. Actually i don’t expect getting married, at least any time soon, so there’s no point of not having sex. Also i having regular sex with some random guy would be so boring and first time painful, because i still have a hymen. I’m considering to become sexual freak or smth. Maybe I should be AO? Any suggestions?

If you no longer have a strong reason to continue retaining your virginity, then yes, you might consider starting to have sex. I personally don’t subscribe to the whole “saving yourself for marriage” concept, but I recognize that it’s important to some people and is obviously each person’s choice. I do think sex is a fun and important thing in life and something people should make the most of and enjoy, so if you’re at a point in life now where you want to enjoy it, then I would suggest you do so.

Anal and vaginal both have the potential to be painful or at least uncomfortable when you first experience them, though neither have to be. If you do decide to retain your vaginal virginity and become anal only, I would strongly suggest exploring that part of your body on your own first if you haven’t already, and learning how to enjoy anal penetration and stimulation, so that when you first try anal with a partner, you’re ready and will be able to enjoy it. Have you tried masturbating anally? Do you know whether you enjoy it?

If you’d like further advice or to continue conversation on this topic, you can either reply with another anonymous ask, contact me via tumblr’s messenger, or join the Anal Only Lifestyle Forum or Discord server to chat with a group of people. (The forum has a few active members who are anal only vaginal virgins and may be able to provide you a perspective closest to your own.)

Anonymous: Week 3 of Anal Only September and honestly, I’m going another month. At least… 😉

I’m not surprised, but I am thrilled to hear it’s going so well for you. When someone does an anal only month as a personal challenge or to try something new sexually (as opposed to it being, say, a punishment or something in a D/s context) I find a majority want to keep going after.

I think the reasons for this are twofold—general enjoyment of being anal only, the thrill of succeeding at their challenge, and not wanting it to end; and the fact that they’ve been having regular anal sex makes it a lot easier in general to do anal, the more frequently you’re getting it up the butt, the better it feels and the less warmup and preparation you need each time.

Enjoy! (I know you will.)

Anonymous: How can i gape my ass hole

With lots of practice. Masturbate anally, have anal sex, and wear butt plugs often. The more you do, the more you’ll increase the range your ass can easily expand, and train your anal muscles to relax more easily. Then, after working up in size, push out to relax your muscles while spreading your ass, and you should start to gape.

zephyrrb: My wife loves anal sex but doesn’t orgasm, I don’t want to go back to vaginal but how do I get her to orgasm thru anal sex? Thx

Does she combine clitoral play with anal sex? Most women need clitoral stimulation to orgasm, at least without further practice/training. Some lucky women find themselves able to orgasm from anal alone, with zero clitoral stimulation, but in my experience at least that’s relatively uncommon.

Aside from that, here are a few (but not an exhaustive list of) things you can try to work towards a fully anal orgasm.

1. Try having her go a few days or more (actual length of time can vary depending on how long it takes her to get extremely horny) without any orgasm to boost her level of arousal and make her more sensitive. Edging can help during this time as well to amplify and speed up the process. Then when she’s so horny she can barely take it anymore, have anal sex and see if she can manage to orgasm from it in that aroused state.
2. Related to the previous, an edging session to get her aroused and sensitive, followed by anal sex with just a little bit of clitoral stimulation to try and get as close to the edge as she can and then letting go to try and let the anal carry her over the edge into orgasm. Repeated practice of this can lead to less and less clitoral stimulation needed, and may over time let her orgasm just from anal.
3. Try having anal sex while she has a full bladder. This can make her both more sensitive and reposition things a bit inside to make anal penetration more likely to also stimulate her orgasm trigger points.

The original version of this post on Tumblr received this response:

masters-rabbit-hole: Also try to have her not touch her clit at all until she cums some other way. That’s how I’ve trained all the women I’ve been with throughout the years to cum via penetration. Latest success is my slave can now cum via anal penetration alone. She says they’re the largest orgasms she’s ever had. She also now has a hard time cuming with her Hitachi on her clit. To her brain that is not ‘sex’ anymore; penetration is.

I think the biggest reason some women can’t cum via penetration is they can’t keep their fingers off their clit. This can be the same for men if they jack off too much. The brain is trained, over years for most people, to only associate masturbation with sex. You have to retrain the brain. Takes months, from my experience 4 or more.

There’s been a Ted talk on this subject. It was slightly different, about the association of young men with ED and their masturbatory habits. They removed masturbation and it retrained their brain on ‘what is sex’ ‘what should evoke a sexual response.’

Anonymous: I honestly thought there was something wrong with me. I learned early that the easiest way to cum was from anal stimulation. None of my partners until recently wanted to even try anal, but my current lover is a self proclaimed Ass Man & eagerly fucks my ass, but likes to play with my pussy when he does. I get very wet when my ass gets fucked, & he’s fascinated. The problem is I cum really easily from my clit, but the orgasm from anal is much better & stronger! How can I convince him “hands off”?

I would just come straight out—maybe not during sex itself, but before you have sex sometime—and explain the situation to him. Tell him that while you don’t dislike the feeling of him playing with your pussy or clit while he fucks your ass, you love cumming from anal itself, and when he rubs your clit it short circuits that process and prevents you from getting the bigger orgasm you’d enjoy even more because you cum from your clit before you can get the orgasm to build from just anal. Most people are eager to help their partner get the most pleasure they can from sex, and should understand the appeal of what you want.

You could also phrase it a bit differently—asking him if he wants to see you cum just from his cock in your ass and nothing else, and to avoid touching your pussy in order to try, then when you do, tell him that you enjoy cumming that way even more.

Anonymous: So I never did anal but my daddy wants me to become an anal and mouth slut only, and I can’t say no to my daddy. But he wants it to be hard for me so he makes me come every days by my pussy and my clit. He wants to be sure I’m ready to abandon everything for him so he makes me addict to pussy/clit orgasm before the day he will choose, I have to abandon that and become anal only. And he doesn’t want me to touch my ass because he wants to wait until he says so. So I wait for him.

This isn’t really an approach I recommend, because it’s generally advisable for most people to transition into anal only in order to best enjoy it, and while some find they do right away and can cum from it without clit play, most need a more gradual approach to get to that point, if they can at all. But, if you’re determined to do it this way, good luck.

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.