Anonymous: You said that the thing you miss about being anal only is being able to get fingered or have your ass played with during sex. Do you not miss your pussy being fucked very much, then?

reguara: Not really. I enjoy clit stimulation, but i don’t miss the penetration.

littleuselesslillie: I have gotten this question a lot: “do you orgasm with anal?”

Yes, and it is incredible. I cum harder with anal fucking than pussy.

During my visit with Master Daddy last week, there was absolutely no pussy fucking…working towards anal only whore.

Anonymous: What made you decide to try becoming an anal only girl?

reguara: I was already an anal always. At first I thought it was a joke, but soon enough I realized it was the natural next steep.

Anonymous: I cant get butt plugs but love anal stimulation, what can i use?

Fingers are always a good option that many people have available with them at all times. Make sure your nails are trimmed and filed to avoid any rough edges. Some hairbrush handles, if there’s nothing sharp or rough or pointy, can work as impromptu household anal toys. Some people work up to small plastic bottles, etc. Don’t use anything glass that isn’t designed to be a sex toy, don’t use anything potentially sharp, and don’t use anything that could get easily lost inside like a ball or anything of the sort. Anal toys have a flared base for a reason, so you can’t get them stuck inside. Good luck and enjoy!

Anonymous: So my gf loves what I lick her butthole and use my finger but is afraid to try anal sex. Any tips on how I can at least get her to try it?

Get there gradually. It’s a big jump to go from a finger to a penis. Work with her to increase size gradually over time. Don’t make it about getting to having anal sex as fast as you can just yet, just make it part of anal play and focus it all on her enjoying it and learning to relax and open up comfortably. Try working up to a second finger, then a third. Then get her a butt plug she can wear during sex and masturbation, etc. Continue with gradual toy size increases over time as she gets comfortable with each, and if at some point she feels ready to try having anal sex, then try that.

kinkyplaymate22: When starting to try out anal sex, I’ve been wearing plugs here and there. Last night we were successful. Yay! Lots of fun! But I was wondering do you take a few days in-between and start again or go for a couple days then take a break?

Yay indeed! You’ll have to play it by ear and see what works best for you. If you’re getting sore and it’s noticeably uncomfortable, then take a break. If everything’s still great and you feel fine, keep going.

Anonymous: my daddy gave me my first plug for Christmas today, yay!

Congratulations, and merry Christmas! I think butt plugs make for excellent gifts for any holiday and occasion, for a partner or even a close friend. The utilitarian value is one part of it, and a great way to start introducing someone to anal pleasure.

But it’s more than just that, and with so many aesthetically beautiful plugs out there these days as well, they really can and should be seen as a form of jewelry as well.

Anonymous: My girlfriend loves anal sex. We do it more often anal than vaginal on her initiative. She often says her pussy is too sensitive. I wonder if she wants to do anal only. I am not sure I would, although I love licking and fucking her ass. How would you broach that subject?

Just ask her, without pressure either way. You could ask her if she’d like to try just doing anal every time for a while since it seems like she doesn’t enjoy vaginal very much. Neither of you needs to commit to it long term right now, just consider trying it out together and see how it works for you. It’s possible she’s only doing vaginal for you and not enjoying it very much. Talk to her and discuss it openly with each other.

Anonymous: Found your blog. I absolutely adore it. I’m 22 and I’ve used toys but have never had sex with a man. I love the idea of my pussy being “closed”. But not with tape or piercings. How can I get my pussy to never, even accidentally, gape? Is it just a matter of never using it? Or is there something else I can do… I’m a fan of the open/closed configuration 😉

Thanks! It’s going to primarily be a combination of individual anatomical differences between people, and a lack of use. So I would definitely encourage only playing with and penetrating yourself anally, both solo and with future partners, to help maintain that unused and more closed appearance vaginally.

evangoldman1: Do you have any tips for a guy who wants to give anal, but never has?

Do a lot of reading on the topic. Read through the Anal Advice category here, search for anal advice, how to enjoy anal, etc. on google and read a wide range of articles from a variety of perspectives, including ones targeted at women so you have an understanding of what they need to do to relax and open up for anal, too.

Essentially, communicate, and work together with your partner to get to the point where she’s ready to try anal. Go slow. Warm her up first, gradually easing up through sizes. If anything hurts for her, stop. Figure out why it’s hurting—not enough lube? Too much too quickly? Not warmed up enough?—and try going back down in size for a few minutes before trying again, etc. Lube and gradual warmup through the sizes are the basic keys to preparing a partner for anal.

If she’s more experienced at anal, she may not need as much warmup. Everybody’s different. Talk and work with her to do what she needs to enjoy anal.