This will be less of a ‘how to anal sex’ guide and more of an ode to sex with the part of the body that concerns us all: our bums. Everyone has one, and since everyone has one, regardless of their gender, butts are totally inclusive and don’t even let bigots take them for their crude views of the world. Furthermore, they belong to our more fleshy body parts. You can grab it, slap it, photograph it, worship it, paint it, lick it, bite it, pierce it, massage it, caress it, put it into plaster, spit on it, sit on it, trample on it, hold on to it, write on it, use it as bongo drums or as a base for your tablet or eat directly from it etc. All in all the ass, ass cheeks and the asshole provide a wonderful base for further exploration and perverted creativity.
The (queer) history
Another reason to try anal sex is the ‘Gotta Catch “Em All” of sex practices that used to be considered sodomitic. The fact that only homosexual men were, and presumably still are, labelled ‘sodomites’ is a fairly recent development. Christianity in particular was a master at framing all sex practices that did not fall under reproductive sex as sodomy and therefore as sin. By the earlier standards, almost anyone who has sexual intercourse today would be a sodomite: mutual or solo masturbation, oral sex, the use of sex toys, grinding, frottage, lesbian sex, etc. While I imagine the non-queer population of this country has definitely masturbated, performed oral sex or possibly even used sex toys, anal sex is not on the list for many. So buck up and contribute to the already loaded history of anal sex to make it even more loaded.
Pegging
I’m a big fan of equality, which means that everyone is allowed to top or be the bottom (if they want to). At the same time, I’m a big fan of the British sex historian Kate Lister, who wrote an excellent article called ‘Why all straight men should try pegging once’ – and to be honest, I completely agree with her.
The main points are: Although pegging is always portrayed as a heterosexual practice, anyone can be pegged or pegging. All you need is a strap-on, a dildo and plenty of lube (there’s never such a thing as too much lube!).
Secondly, the more people (especially heterosexual cis men) embrace pegging and enjoy the truly powerful orgasm, the less homohysteria and bottom-shaming will be accepted and hopefully they will begin to disintegrate like other forms of discrimination.
Thirdly, destigmatise male health care! Prostate cancer is the most common type of cancer in men in both the UK and Germany. According to the Robert-Koch-Institut, around 65,820% of men are diagnosed with it every year. Why? Because men don’t go to the urologist and have their prostate examined. Despite sexual education, the critical masculinity movement, feminism and greater acceptance of homosexuality in society, cis-hetero men are still afraid of someone sticking their hand up their bum. Sure, the first time isn’t pleasant, but that’s why it’s worth thinking about pegging. On the one hand, it trains the sphincter muscle to relax; on the other hand, you are less embarrassed during check-ups. Granted, getting fucked in the bum is still more pleasant than a medical examination, but dear men, you get the idea, don’t you?
Queering the prostate tissue
So far, so good. So far I have found that anal sex is usually accompanied by some form of prostate stimulation. Sometimes just stimulating the anus with tongues or fingers is enough, but even here: You get the principle. Now there are exceptions, and that exception is me. So not me, but trans men or any person who undergoes gender reassignment surgery that involves testosterone. In 2020, The American Journal of Surgical Pathology published a study that found areas of partially advanced prostate tissue in the vaginal canal of a total of 7 out of 8 trans men who received testosterone and four intersex people who had an excess of endogenously produced androgens. The scientists concluded that our bodies are much more flexible in the expression and development of our sexual characteristics than previously assumed. This makes sense when you consider that the respective primary and secondary sex organs only begin to form in the sixth week – there is no difference before then. So I may have several mini prostates in my vagina. Sadly, I can’t feel a difference between my sex life before being on testosterone and now.
The actual meat of
Ever since I made the conscious decision to join the dark side and allow myself to be corrupted (there wasn’t much left to be corrupted), this has been an important part of my interests. But the practical realisation was not so obvious. I lived with my parents for a relatively long time and had a lot of questions about the subject anyway, which is why I was happy to put it to one side. I had a lot to consider: hygiene, training and the appropriate aids, which I didn’t have the money for. I also had health problems that came up at random. The questions about suitable products and methods remained unanswered. My former partner was able to answer some of them for me, but the complaints remained. The idea that intimacy should not be work also left its mark on me. All the effort involved in healthy eating, hygiene and training was five steps too many in the heat of my newly discovered feelings.
Then I moved out, had my own four walls, my symptoms disappeared, I started hormone therapy and discovered cheap but good products. However, nothing changed at first. I didn’t have anyone who wanted to get intimate with me for the first time, and even the people on Grindr weren’t keen to be my first experience. Lube was essential by now anyway, but suitable aids for beginners were still not in the budget. I tried a few times with a relatively small toy and it hurt so much that I didn’t try it.
Then my accident happened. I was not allowed to have penetrative contact for six weeks and my involuntary celibacy and suffering took its course. After four weeks, I developed detailed techniques to climax through external stimulation alone, and it wasn’t long before I was really considering the legendary ‘special climaxes’. I told my girlfriend all this while she showed me her adjustable toy, which unfortunately was far too big for me. She turned to me, gave me a long look and said, ‘Too big isn’t the problem, I have some smaller ones too,’ and with that she presented me with three tools just the size of my finger. Before I could even protest, I was lying on my back like a defenceless bug, my legs were folded upwards and with a lot of lube and an uncomfortable tug, something was suddenly stuck inside me. ‘Well, that was fast and… unexpected’ was the only comment my brain could come up with. There I was, lying in a double bed in a basement flat somewhere in southern Germany, having a light-hearted conversation about intimacy that escalated within seconds. The feeling was… strange. The first few minutes were not pleasant, it felt more like I had to go to the toilet very urgently and couldn’t. A bit of walking around worked and relieved the tension, but in the end I was interested but not yet convinced. When I got back home, my curiosity got the better of me and I tried it out. In the meantime, I had two smaller aids, a small toy and a normal-sized toy, which at the time was practically the final boss for me.
I quickly realised that there is no such thing as too much lubricant. Erotic media helpes, as does external stimulation, as does relaxing beforehand and – even more difficult – staying relaxed while being penetrated. (If anal sex is particularly painful to you, you might wanna look into your pelvic health.) With that, a practice routine was found, and soon I had worked my way up from finger-wide to small to long-thin to my final boss. Which not only (shamelessly) boosted my ego, but also satisfied my cravings, stimulated my digestion (yes, too much information. I don’t care), gave me intense climaxes, I slept better and gave my purple toy a second raison d’être, as I could no longer use it for my go-to-routine. To all people, who are new to testosterone vaginal atrophy is a bitch and every vaguely realistic dildo with a slightly bigger corona glandis will be a pain to insert, therefore just don’t do it. It is not worth it in contrast to good anal sex.