Dear Dr Ren,
I need your advice. I’ve been curious about anal sex for years. Lately, the only fantasy I have is someone doing anal to me. I’ve even browsed the web looking for TS girl escorts who would top me. I found out that I first need to practise having something inside me and I have to make my anus look presentable. I’ve been practising, but I can’t bring myself to hire a professional.
I’ve been thinking about asking my girlfriend to wear a strap-on and do anal to me, but I’m afraid if I tell her what I want she’ll think I’m gay or perverted. Can you give me any suggestions regarding how I can present this idea to her?
Dear Butt Bashful,
I am so glad you wrote with your questions instead of just fantasizing and feeling frustrated about butt fucking. I’m happy to clear up the common misconceptions that are keeping you from enjoying this new behaviour.
As to your search for “TS girl escorts who would top” you, I fear you may be seeking unicorns. You would necessarily need a pre-op woman who is not taking estrogen and can still attain erections, and MTF women generally prefer not to take the top role. This means you would be looking for transvestites or crossdressers, few of whom engage in escort services, and, of course, the gender role dilemma still holds. In other words, your search will likely be fruitless, not to mention the consequences your straying could have on your relationship and self-esteem.
Regarding the need for practising having something inside you, it really isn’t necessary. You need to learn how to relax your anal sphincter muscles so that insertion is not painful, and you already know how to do that. After all, you open those muscles regularly to do your daily duty. The difference with anal sex is overcoming inhibitions and relaxing willfully.
As for making your asshole look presentable, I assume you are referring to anal bleaching. Not necessary. Your rosebud looks just fine, or at least as fine as anyone else’s.
That covers what you don’t need to do.
It’s important for you to know some facts about anal sex. First, the whole pudendal area, the sling from our pubic bone to our tailbone, is loaded with sensitive nerve endings, in both men and women. When we are aroused, our whole genital area gets engorged and feels good to the touch, including our bum holes. That said, some of us like anal penetration and some of us don’t, just as some of us enjoy spanking/ kissing/porn and others don’t. It depends on preference, not on orientation, gender or mental health. We are all individuals, with an amazing range of erotic turn-ons.
May I suggest you get Dr Carol Queen’s DVD Bend Over Boyfriend and Joseph Kramer’s Anal Massage series. Watch them by yourself before introducing them to your girlfriend, and then show them to her in combination with other DVDs about sexual adventuring so the topic of anal stimulation isn’t conspicuous. Let her know you’d like to explore sex further; watching these videos will help you both learn what turns you on. Discuss what happens in each of the videos after watching them. Sometimes it’s easier to talk about other people’s sex than your own. Then it’s an easy leap to discussing your own behaviour, especially with the catalyst of planning hot sexual encounters.
Also read Jack Morin’s Anal Pleasure and Health and Tristan Taormino’s new book, The Ultimate Guide to Anal Sex for Women, which you can share with your girlfriend. Inform yourself about anal sex so that when you introduce the topic/behaviour, you are confident.
Many women experience powerful orgasms from anal penetration, as do men. A smart fella might introduce anal sex to his partner as a new behaviour that they both try, so you don’t feel awkward about asking for something new that she may question.
You may also want to examine your homophobia and your definitions of perversion. If you did not fear being judged as “gay or perverted,” would you not have negotiated a bit of backdoor nookie before now? If you can leave behind (pun intended) your negative attitudes toward sexuality, you’ll be free to enjoy all your body has to offer.
Regarding the prevalent attitude that anal sex is gross or dirty, you’ll find that most people appreciate not having to deal with poop. Address this by doing a thorough enema pre-date. And if you leave a smudge during all the excitement? Well, sex is a messy business. Wipe up and laugh it off.
You’ll also want to remember that the anus does not self-lubricate. Use lots of lube! No pokey objects. Slow and easy wins the race.
I encourage you to explore your fantasy of anal play, and to offer the same potential fun to your girlfriend. You can only benefit from open communication and unself-conscious sexual exploration with one another. Go for it!