Posted by: littlegirlyone | November 25, 2008

ask the little girl: becoming an anal girl

I’m no sexpert, but I’ll always give honest answers. Lauren emailed me with the following question a couple of days ago. I gave them some thought, and sat down to write her back. I’m hoping this can be a new feature (plus, it will give me something to write about). So, go ahead and ask the little girl at littlegirlyone @ g mail . com. (Spaces inserted to foil spambots; you know what an email address looks like, right?)

Hi littlegirl,

I’ve been reading your blog for a few months now and I am slowly going back into the archives to read what I’ve missed so far. I read your posts today, ‘anal girl‘ and ‘never have i ever…‘ Now, I understand that you’re not an advice column but if you are ok with responding (I totally understand if you don’t want to, it’s pretty personal) I’d like to ask you a quick question. My boyfriend wants to have anal sex and I am TERRIFIED of it because I am the furthest thing from a painslut. I’ve had an enema before, which was not pleasurable like your experience, but I have never had anal sex. Are the feelings similar between the enema and anal? I just have a very low tolerance to pain and I can’t get my mind wrapped around how it can be pleasurable. So, I guess what I am asking is if you find it pleasurable because the essence of pain turns you on? Or if I am making a big deal out of nothing and it might not hurt as bad as I imagine?


hey lauren,

no worries about the advice columnist thing. i’m totally flattered. in fact, you have just given me an idea for a feature: ask the little girl! anyway. i think your question is: can i have anal sex, and will i enjoy it if i’m not a masochist? and, does anal feel like an enema?

to the first part, my answer is yes yes yes! you can enjoy anal without being a masochist because anal doesn’t have to hurt. granted, girls like me sort of *like* it to hurt, at least a little. hell, some like it to hurt a whole lot. but, it can be super sensual and feel amazing and not hurt at all, or at least, only for a little bit.

if you don’t like enemas, i wouldn’t suggest one. the two things i like most about them are 1) the warm water feels nice; and 2) then i don’t have to worry about messiness. just take a nice bath or something instead, and give your girl parts a good scrub with a washcloth (just for your own peace of mind, you know). basically, you want to feel as clean, sexy and soft as you can.

next, bust out the good lube. i don’t know if you’re using a condom or not. (water-based lube always for condoms!) i like slip inside, a water-based lube they used to sell at good vibrations. apparently, however, oil-bsed lubes are the gold standard for anal sex. (probably because they are thicker and more emollient.) use the thickest, slipperiest lube you can find that is appropriate for your situation. have your boy rub it all over yourass. he should definitely use some fingers, or a really small butt plug to get the lube inside you, as well as on the outside. he also needs to put lots and lots of lube on his cock. i can’t say this enough times: if you don’t want it to hurt, you can’t use too much lube. put it everywhere.

i think fingers are a nice way to start. they’re relatively small and, as long as there’s no long nails, smooth and easily controlled. start with one finger (yours or his). if it hurts, go slower and add more lube (it shouldn’t hurt). add another, maybe up to three. this should be sensual and make you feel hot and wanting. if you’re scared, you’re going to be tense and then you’re going to be tight, and that will make it hurt. the goal here is to get you to want him in your ass.

when you’re feeling ready, he can press the tip of his cock on your asshole. i mean it, the tip! don’t feel like you have to let him lead at this point, let him know the second it feels uncomfortable. if it hurts, go slower and add lube. he can slowly, slowly feed more of his cock into your ass. don’t be scared. tell him to pull back and add more lube anytime it hurts. take your time. work him in tiny bits at a time. relax, close your eyes, and feel him pushing into you. it should feel like stretching, but it shouldn’t feel painful. when he pushes in, think about opening to him. don’t get scared–you will tense up. if it helps, you be the one in control of penetration. you push your ass onto his cock when you are ready for more. tell him not to move, just to let you work it in yourself.

another trick is to change positions if it hurts. i have fantasies about having anal sex in the doggy style position, but thus far, i haven’t been able to take a cock in my ass without pain when i’m on my hands and knees. i have to be on my back, more like classic missionary. try that position first, if that doesn’t work, try laying on your stomach, or try being on top. basically, experiment and see because you might be able to take it in one position and not another.

once you get it all the way in, stop, breathe, and celebrate what a dirty little anal whore you are (if you like that kind of thing). this is where it can get fun. if your man likes to talk dirty, this would be a prime opportunity for him to comment on how hot you are, how your ass feels amazing, etc. he cannot just start banging away like he could in your pussy. he just has to accept that this is different, and that he will need to start slow and gentle, at least for now.

when you are ready, have him move it a bit. see what feels good. sometimes moving in circles feels better and is easier than thrusting in and out. play with the new sensations. touch your clit. if you’re anything like me, your clit will be begging for some attention at this point. (i’m almost always dripping wet when something fills my ass.) try to enjoy the fullness feeling, and you will enjoy the sensation more. if you can rub yourself to orgasm with his cock in your ass, be prepared for a head spinning, nonesense-making orgasm that will leave you weak in the knees. if you have one of those, i’ll bet you’ll be a little more interested the next time your man wants to do it like that. once i had an orgasm when my ass was full, i turned into a full on anal girl.

ok, all that talk of anal sex is making me wet. let’s move to your other question: does anal feel like an enema? the short answer is no. because anal involves a pretty solid and hard penetration, and enemas involve very small penetration by the nozzle, and then the sensation of water. enemas go farther up in your colon and anal canal than a cock ever can, though. so, if some of your dislike of enemas is that feeling of the water being deep inside, anal won’t give you that feeling. if enemas are painful/give you cramps, remember it’s the enema water up there causing all the commotion. his cock and the lube just won’t get that far up.

i hope this answered your questions. please let me know if there’s more i can tell you. i’m so worked up after writing all that, i think i might have to sneak off to the bathroom . . .

(*hides blushing face in hands*)


  1. Thanks again! :)I’m still nervous but I won’t back out now.

  2. phew… I think I am missing something

  3. Well the other thing is that sometimes you just have to get through the initial pain. I have pain in any position when he goes in, then once I breathe a bit, he rests for a bit, then starts to move, the pain starts to dissipate. A lot of him playing with your clit and sensitive bits will also help get rid of the pain and bring on the HELL yes please.xx milla

  4. When Master took my Anal cherry it did hurt. More than I expected or wanted it to. The sensation was unbelievable. I an’t wait to until next time!Slave Jo

  5. Lauren,The important thing is to go slowly and use lots of lube (as little girl says). You may simply want to experiment on your own. Explore with your fingers to get a sense of what he can do.I highly recommend cleaning out with a good enema because it also removes matter that can cause abrasions, and it makes for a more pleasant experience. It doesn’t sound like you like this all that much, but go slowly and gently. My girls sometimes take a half hour or more to prepare, so don’t rush it.Also, I’d recommend condoms and gloves generally. It makes everything easier to clean up. Just be sure to match them to the type of lubricant. If you use an oil-based lube then you can’t use latex–it will just break.For subs I’ve worked with the main point of pleasure is the submission, not the pain. So, I use a lot of fingering first to relax the sphincter muscle. One trick is to massage the entire area from inside the vagina and outside the body. Just be sure that your partner doesn’t put anything in your vagina that has fecal matter on it. Once it’s been anywhere close to the ass hole it can’t get anywhere close to the vagina. But, a good, gentle massage of the anal canal from the outside before any kind of penetration might make it easier. (He should put a finger or two in the vagina and a thumb on the outside of your body near your tail bone so that he can gently squeeze your anal canal between them, then massage.)Also, use a good (but old) towel underneath so that any spillage has some place to go. If it looks like a long session, I’ve put plastic wrap under the towel, too, to keep the mattress clean.And, girls can be face up or face down. We like the feeling of submission from having the girl bend over and take it, but the face to face contact is also quite nice. Are you ready to look him in the eye when he does it?Hope this helps you have a pleasant experience!–Rich

  6. […] me for advice. I’m not sure how many of you remember when I tried to start an advice feature before. But, since Potenta left her questions in a comment on one of my Project Orgasm posts, I figured she […]

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