In case the title wasn’t explicit enough, here’s your last chance to click away if you really don’t want to read a frank post about sex.
I’m not single now; haven’t been for nearly 20 years (except for a brief spell between marriages). But I was for the first 24 years of my life, so the title is partly relevant (I just liked the sound of it). I must confess to some feelings of trepidation about this subject since I acquired many inhibitions while growing up regarding discourse on sexual matters. Indeed, that’s as good a place as any to begin…
I grew up in a fairly typical middle-class family. My mother gave up work to care for me and my younger brother while my father held a professional/management job. A privileged upbringing: private education; safe, loving home; freedom to think freely. But there was one subject that was never mentioned at home: sex.
I don’t think I was even aware of sex until I accidentally discovered the pleasure of rubbing myself in a particular way: I’m sure many young people have independently discovered masturbation. I guess I was aware enough of the taboo nature of those body parts to keep my discovery to myself.
I believe if I had raised the subject with my parents they would have been far too embarrassed to respond positively: they had been raised Christian-fashion to think of this as something sinful rather than it being a harmless, pleasurable way to explore one’s own body and sexuality.
I remember having a single sex ed. class at school. It must have been when I was about 12 or 13 and it simply covered (using textbook-style illustrations) comparative anatomy and conception. It was too far removed from reality for me. I learned basic details: the male has a penis and testicles, the female has a vagina, uterus and ovaries. The penis is inserted into the vagina, the testicles produce sperm, the ovaries produce an egg, and one sperm somehow coincides with the egg in the uterus, fertilizing it and causing it to develop into a fetus (and thence into a baby). This was all the preparation we received for adult, sexual lives.
This was the 1980s: there was no internet as we know it and TV didn’t show anything more than kissing (at least before the time I had to go to bed). Playground “gossip” mostly passed me by but what I did glean about sex only taught me that it was a forbidden subject. Honestly, I wonder that we have continued as a species with these attitudes!
What I did learn about sex came from books such as the later Dune novels which described manual stimulation of the clitoris and labia. I formed the idea that that was a key means to provide pleasure, an idea that time and experience have done little to dispel.
My experiments with masturbation techniques also led me to discover anal stimulation. First it was simply stimulation of the anus itself, but I soon learned that I enjoyed the feeling of penetration as well. But the main focus was my imagination: I would picture myself having sex with a partner while I stimulated myself, usually by straddling and rubbing my genitals against something.
I would also lie on my back and imagine how it would feel to have a man atop me, entering my vagina, thrusting rhythmically, raising me to a pitch of ecstasy. Which was curious in a way because my sexual attraction has always been primarily towards women. Not to mention the fact that my anatomy was incongruously male. To explain: I am attracted to the female body but at the same time I picture myself as female when I imagine having sex. In fact I always picture myself as female-bodied: that’s the cause of my gender dysphoria and why I’m pursuing medical treatment for gender confirmation.
This didn’t confuse me: I just accepted it as the way I was (although I did enjoy seeing myself in the mirror dressed in clothes borrowed — without her knowledge — from my mother, and wished with all my heart that there was some way to step through and be the girl I saw in reflection). But that wasn’t possible and I didn’t feel able to talk about this to anybody so I kept all these feelings inside.
It did make me wonder for a time whether I had fetishized my cross-dressing, but I came to realize that there were two separate forces at work here: my identification as female, and the consequence that had on my sexual desires. I never found wearing female clothes to be sexually stimulating; rather it was that I was consistently female even within my sexual fantasies. When I would masturbate while dressed as female the clothing was an external confirmation of my internal identity rather than a source of sexual stimulation: it masked the discordant note introduced by my physical body.
As I grew into my late teenage years I became aware that several of my peers had boy- or girlfriends but my own understanding of relationships was very late in developing and I didn’t ever consider that sex could form part of the picture. I never had any relationship beyond friendship until the age of 23.
It all changed when I met the woman who would later become my first wife. We met socially and it was her who initiated every stage. I still don’t know what attracted her to me but we did, at least for a while, get along very well. I don’t remember exactly how it happened, but one night shortly after we met she came back to my flat. We shared kisses and cuddled.
I really had little idea of what to do: she led the whole way. I basically had to be instructed what to do at every stage. It was several dates later (with things slowly progressing each time) that I was induced to have full, penetrative intercourse: penis in vagina. It was… intriguing. I reached orgasm (which was familiar from my experience with masturbation) but on the whole the experience was rather less than the earth-stopping event that I’d been led to expect.
With hindsight it’s clear that we were both young and inexperienced, and didn’t communicate effectively. I’d had years to discover what forms of stimulation worked best for me (and I assume the same was true for her) but we didn’t share this knowledge and simply applied what we had been taught was the “normal” way of doing things.
After the initial novelty wore off I began to lose interest in sex (although we do have a daughter from this brief period). I’ve since realized (many years later) that apart from the direct genital stimulation I do not find sex where I perform the male role either arousing or fulfilling. Using the penis in that way does not feel natural.
My gender transition has been positive because it’s allowed me to overcome some of the inhibitions I had regarding talking about sexual matters. I didn’t even realize just how deep those inhibitions ran, how much baggage I had picked up from my childhood, until that moment of release.
The secrets to successful sex are self-knowledge and communication. You have to be familiar enough with your body to know what forms of stimulation work for you, and — equally as important — you have to be able to communicate that to your partner. And vice versa: they have to be able to tell you what works for them.
Openness is vital: you need to explore each other’s bodies and provide the feedback that guides and informs that exploration. Be open to experimentation but always in a consensual manner: state your boundaries and respect the other person’s. But above all have fun: ultimately it’s all about the pleasure.