An Uncensored Account Of My First Anal Orgasm
How an untapped source of pleasure led to sexual self-discovery
I like reflecting on my intimate experiences, because it’s my way of celebrating my sexuality after a sex-negative upbringing.
I grew up absorbing messages such as “a woman who gets involved with a man outside of an arranged marriage is ruined”, and “anal sex in any context is prohibited by God.”
I choose to reject the guilt and shame.
In more recent years, I’ve come to view sexuality as a fascinating subject which can tell us much about ourselves and our connections with others. Discovering what we find arousing helps us to tap into previously unexplored parts of our psyche.
Writing about sex, including anal sex, is my way of rejoicing in that exploration, and rejecting the guilt and shame which dominated my thinking for so long.
My partner knows I write about sex.
Last weekend, we were joking about this together. While we lounged about on his bed, he playfully pretended to read aloud from a (non-existent) excerpt of anal erotica he made believe I’d written.
In a deep, booming voice (this was an interesting choice, since he was impersonating me as the female narrator!) he declared: “My sphincter spasmed around his penis, and my ejaculate showered the walls like paint…”
We ended up in stitches of laughter on his bed at this comically overexaggerated scene.
The surprising thing is, his joke actually turned out to partially foreshadow events which unexpectedly unfolded later that night.
Coital orgasms haven’t always come easily to me.
Before I met my current partner, I’d only really been able to orgasm through masturbation.
Reaching my first orgasm during vaginal sex with my boyfriend took a long time. I believe I was only able to get there because he didn’t pressure me, or analyze our sex life through an outcome-focused lens. Instead, he continued to make me feel safe, loved and respected, whether I climaxed or not.
We spent dozens of sex sessions discovering different ways of maximizing each other’s sensual enjoyment in the moment, as opposed to fixating on an orgasm which might or might not follow.
In time, with plenty of experimentation and clitoral stimulation, my orgasm surfaced of its own accord. As our relationship developed, so did my ability to orgasm more frequently through sex.
Last Saturday, though, I experienced my first orgasm of a different kind.
That particular weekend, we happened to be out of condoms.
We’ve both been STI-tested, and we were both down for some kinky time. However, with no contraception on hand, we didn’t fancy running the risk of an unwanted pregnancy. (I’ve since had a contraceptive implant put in.)
After discussing possible options, such as a fun evening of oral-only play, we settled on enjoying some anal sex.
I’m still quite inexperienced when it comes to anal sex.
I’ve talked in great detail here about the process that we go through to make sure that anal sex is comfortable and pleasurable for both of us.
I’ve had unpleasant, painful anal sex in the past, and I’ve only truly been able to enjoy the act with my current partner for a number of reasons, including strong mutual trust and a deep sense of security.
However, in comparison to vaginal sex, anal sex is not something we engage in very often, and you could consider it a relatively new area of my sexuality which I’m still in the process of exploring.
Amazing oral helped to get me in the mood.
After I’d been to the bathroom, made sure that my rectum was empty and that my perianal area was rinsed and ready for playtime, we settled down for foreplay.
My boyfriend has become very astute at reading my body, and I’ve also become more confident at asking for the kind of oral stimulation I want. My requests for extended oral — including ‘ice-cream’ licks from my perineum up to my clitoris, and between the folds of my labia — did not go unheeded.
I mention this because as a woman, I haven’t always felt comfortable asking to receive as much sexual pleasure as I give. Overcoming this hesitancy with a loving, considerate man has marked a wonderful milestone in my sexual development. I’ve learned to express myself as an equal in a sexual partnership.
After a series of sweet shiver-inducing ‘ice cream’ licks, my boyfriend gently pulled back my clitoral hood. Sucking my clitoris and stimulating it with his tongue resulted in a delightful clitoral orgasm which made my legs tremble.
We started with a little anal fingering to help me relax.
Following this wonderful warm-up, he lubricated and caressed my perianal area. The stroking sensation between my butt cheeks and along the sensitive nerve endings of my perineum aroused me.
Next, very gently, he started to finger me to help me adjust to the sensation of being penetrated. During this time, I focused on breathing deeply to relax my body and release any tension.
We carried on this way for a few minutes until I told him I was ready. Lying on my back, I drew my knees up towards my chest to straighten out my rectum and facilitate a smoother entry.
Slowly, he withdrew his finger and inched his thoroughly lubricated penis into my anal passage, continuously checking in with me to make sure I was okay. Finally, he was all the way in.
It was time to breathe even more deeply.
I love being called a good girl during sex.
As he felt my sphincter relaxing, he nuzzled my neck and called me a good girl. I love being called a good girl during sex, and I think it has something to do with how much it stands in contrast to the way I was raised.
When my partner calls me a good girl, I feel rewarded for indulging in pleasure. With him, I’m free to bring out the full spectrum of my sexuality, without my natural impulses being shamed or vilified as they were when I was growing up.
It’s a positive feedback loop which generates more and more arousal. During an act as taboo as anal sex, being called a good girl and appreciated with tender kisses holds even more significant meaning.
For a while, I was in charge. And I liked it.
My boyfriend progressed to some minimal thrusting, and at this point I felt a little friction even though we were both generously lubricated. It’s always best to avoid friction during anal sex, as damage to the anal passage can result in fissures and haemorrhoids!
What I love about my partner is that he’s always extremely attentive to my comfort during sex. So when I asked him to stay still and instead raised my own hips to control the movement, he instantly accommodated my needs.
There was something very exciting about being in this position of power even while lying flat on my back. Being able to elicit the sounds of his pleasure with my own rhythmic motion turned me on even more.
I love feeling the pressure of his body against my pubic bone.
After a while, I let him take over again, and guided him verbally as to the speed and depth of penetration that felt smoothest.
Because we have anal sex in the missionary position, I felt his weight pressing against my pubic mound and bone as he moved in and out of me. I’ve always been sensitive to pressure in this area, and it’s the primary region I stimulate when I’m masturbating.
Add to this the tingling of the nerve endings in my anal passage, and his moans of heightened enjoyment, and it only took a few minutes to build into such a hyper-aroused state that suddenly my sphincter did indeed start spasming around his penis.
(I’ll add I did not shower the walls with ejaculate — but this didn’t make the experience any less pleasurable.)
After he came inside me, we held each other, laughing.
“I didn’t know I could do that!” I said. “Your story half came true!”
As he slowly pulled out and leaned over to cuddle and kiss me, I felt exhilarated about the possibilities that have arisen since I started actively exploring my sexuality.
The fact that the orgasm was unexpected made it even better!
I’m glad I’m finally able to enjoy sex in a healthy relationship of my own choosing.
Since I no longer consider premarital sex forbidden or berate myself for engaging in it, I like talking about it, understanding it, and using erotic experiences to enrich my life.
If you’ve ever been curious about what it’s like to have an anal orgasm, I hope this article has been educational for you too!