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Dear TheMochaPeach: Am I being a Bit Too “ANAL?”

Dear TheMochaPeach:

Girl. I am not sure I can even explain this. I’ve been in a monogamous relationship with my boyfriend for about 8 months now. We have a really great sex life. He definitely knows how to please me and I think I do a good job of pleasing him.  He hasn’t had any real complaints.  However, lately, he’s been asking if we can do some “anal “ sex.  He said he likes it as an alternative if a) we cant have sex due to my menstrual flow and b) it’s tighter and naughty and will give me a greater orgasm. I don’t know about all of that. Now, I am not really down with that but I do want to please my partner. The other thing is, I mean him asking…does that make him gay? I mean I don’t know any brothers so adamant about doing it “in the butt” like this.

“Anal” Annie


Dear “Anal Annie”:

Well my dear, you are in a bit of a “sticky “situation, a “pickle’ if you will, and I know you don’t want to be a “stick in the mud” (lol.boy this letter is ripe for puns! LOL) Okay. Okay…let me stop.

In all seriousness, Miss Anal, I cannot help you. It’s not that I find the act of anal sex repulsive or anything.  I have never been a fan of that act for the sheer pain that it can cause. I’ve had far too many gastrointestinal issues to want to have anal sex (LOL)…BUT with that said. I too am curious as to how it works. I’ve also not had a partner who was even gentle or willing enough to try. (Well…one guy did try WITHOUT asking and I swiftly bowed that ninja in the gut!!)  I did, however, defer your issue to a good friend of mine who absolutely enjoys the act of anal sex.  She’s a lady in the streets and a freak in the sheets. Matter of fact, said person sent me a ton of uhm.”Anal friendly” videos as a “bridal shower gift”…so I think she was trying to get me to open my horizons. (LOL)

And here are her tips (with a little “back-story”…get it.HA! LOL):

I initially had reservations as well, with my primary concern being whether or not it would be painful. Obviously the orifice is smaller than a vagina, and not naturally lubricated, so for those reasons I was a little wary.

The first few times I tried it, much like the reader, it was at the request of a boyfriend. This was about 10 years ago - I was younger, less experienced sexually, and really doing it for him rather than me. All of those factors made the experience pretty unpleasant. It was painful and only barely tolerable. They enjoyed it way more than me.  Afterward I was sore and vowed that it wouldn't happen again, ever in life.

Years later I suddenly got into watching a lot of porn. I lived alone for the first time, wasn't in a relationship (and had been celibate for a few years)... and suddenly anal porn in particular started to really excite me. I’m not sure what made me start exploring that particular genre of porn - curiosity, maybe? But now it just looked really.... sexy. Perhaps this is also because I had been celibate for so long, and my body was aching for sexual intimacy. But suddenly I started getting aroused watching it, and I knew that I wanted to try it again in my next relationship. This time I felt it would be different... because I actually had a vested interest in it, versus doing it to "please" a partner.  I’m not saying anything is wrong with trying out a new, unfamiliar act to please a partner. But for me, personally, level of motivation seemed to play a role in my ability to enjoy it.

In my next relationship my partner and I did try it, and it was so much different than those earlier attempts. It may be a combination of my level of interest, as I mentioned, or perhaps my partner was just savvier. Either way, it felt so incredible and I even became able to orgasm that way.

Here are some tips:

- Start off by watching anal porn. If you find that it makes you uncomfortable, and you simply can't tolerate it (at least in the beginning), that is likely an indication that you aren't ready for the "in vivo" experience. After all, what's the difference? Once it starts becoming erotic to you (on video) it may be time to start experimenting. Also read some erotica/ literature if film pornography isn’t your thing.

- Ease into it with your partner. Come to some sort of compromise. You don't have to have anal sex the very first time. Maybe you can start getting comfortable with some anal play, ie, tongues, fingers, and VERY small toys. Go with your comfort level AND it should feel good. If it doesn't, slow down or perhaps take some time before doing again

- Lots of lube, always. Get a lube that is fragrance/parabin free and closer to your natural body fluids (Try Maximus). Also WEAR A CONDOM. We do not need any particulates from that region getting into your vaginal area. Plus you can get small tears in the anus. Because it is high-risk sex, you can easily get STDs. Change them (condoms) with each sex act.

- Once you're ready to go with the actual act, be sure you relax the sphincter (is that the right word?) muscles - because if you are tense, those muscles will be tense, and entry will be more difficult and/or impossible. Also, try to evacuate your bowls before hand or use an enema to do so (if you are worried about that aspect). Also, try taking a shower if you want to feel fresher.

- Some women find it helpful to have clitoral stimulation at the same time - using either your partner's fingers, your fingers, or a vibrator. That can help distract from an (initially) uncomfortable entry and, ultimately, can make for a more intense orgasm

- Be open with your partner about any fears, reservations, and also fantasies you may have. I think if he sees you are open/interested in trying, versus completely closed, he will be more willing to work with you and be patient

- Get over your fears of him being homosexual. Under NO circumstances do I think the two are correlated. Many straight men enjoy anal sex. Like your partner said, it's exciting because it's taboo and also just plain feels good (the tightness). But if, in the back of your mind, you are questioning your partner's sexuality, that is a major turn-off right there and could make the act even harder to follow thru to completion

My bottom line is that the act is much better when you're genuinely interested in trying it, versus trying to please someone. So if I were you, I'd be open and communicative with your partner.... and hope he is patient with you. In the meanwhile, see if you can't go about enjoying some anal porn (while masturbating to it - yes, I said it!) and if it doesn't "grow" on you eventually, then I would suggest NOT going forward with the real thing. Maybe revisit it again in the future.

So Dear "Anal Annie", I hope that these tips were helpful.  I think my girl pretty much covered everything you needed to know as far as anal sex (and she educated me as well!) In the meantime, be safe and have a happy love-making experience.

If you’d like to Ask TheMochaPeach, please send me an email! All questions will remain anonymous.


  1. May I also add that her partner needs to have patience, and the woman needs to be relaxed whether that's through drinking alcohol (get tipsy, not drunk) or other "recreational" aids.

  2. Wow, great tips! I'm not a big fan of it but have friend who swear by it! So good luck "Anal Annie"!

  3. I could've sworn I had already commented on this post! Maybe in my head I did....? *smh* Anyway, great advice from your lady/freak source! ;-)

  4. Oh yes..she was an EXCELLENT resource!!! :)

  5. It's a truly special something. I remember the first time that a woman asked me to have anal sex. I laughed so hard that I fell out of the bed and lost my erection. A week later when we actually tried it, showed me that clearly I didn't have a clue as to how good it would have felt. It was outstanding.....truly outstanding.


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