I’d like to tell you about the time I first had anal sex. I was twenty-seven and four months into my first relationship[i] with a guy who was my exact type: long, lean, dark shaggy hair, introverted, and artistically stylish; grungy looking in that 1960’s explorer sort of way. And although he was tall and slim, he had rough strong hands. He built things- instruments- which I found sexy, being a cellist and all. Moreover, he was more than just some Bushwick hipster living an artist lifestyle. He was real; emotionally raw. An expat who had been imprisoned for two years. A man who had seen friends die.
Anyways, I digress. I digress at times, you might find. If that is something that annoys you (and anal sex isn’t something you are comfortable discussing) then I suggest you end your reading here. I can’t make that decision for you though, so just do what you feel.
But yeah, the four-month courting period was miraculous. I had finally found romance. And orgasms. The first date, when he sucked greedily on my left breast, I could feel his sadness seep into me, and in that sadness a tenderness grew between us. Our third sexual encounter, the first time we had vaginal intercourse, was also the first time I experienced orgasmic release with a man. He was a slow, gentle lover. It made me feel loved. And the way he would softly kiss my neck before going down on me made me relinquish my sensuality to him. His English wasn’t great, but that didn’t diminish the power of our connection. I grew to know him as he grew to know me. And I liked the manner in which my firm, consoling hugs were needed.
But there was one thing that he couldn’t, wouldn’t give me, that I wanted.
On our four-month anniversary (he was sentimental) while spooning in bed we began talking about our unfulfilled sexual desires. He had had three girlfriends in his home country, so he had done most things. I, on the other hand, had never had a consistent sex partner, so my sexual experience was lacking. But he had never masturbated to completion in front of partner or watched a partner masturbate to completion. So we did that successfully that night.
It wasn’t until the next morning that I admitted my interest in anal sex. When I expressed this desire, I felt the room grow dark, even though sunlight was pouring in drunkenly from the slit in the thick curtains. He sighed and said he couldn’t give me that. I asked him why, but he wouldn’t reply. I felt a stormy sorrow emanate from his eyes, so I got him to turn, pulled him close to me, and cuddled him.
The following month, we no longer spoke about our sexual fantasies, and my orgasms slowly abated until I reverted back to my anorgasmic self. I also couldn’t sleep while he was spooning me. It would make me wet and horny, hoping he would ram his dick into my anus, which it was perfectly positioned to do. A rift began to grow between us, and in the early hours of the morning I would often spend a few hours on the couch reading and writing due to this sexually induced insomnia. By the end of this fourth month, I could hardly function I was so sexually excited and exhausted.
Around three a.m. on one particularly brutal sleepless night, I watched his beautiful naked body emerge from our room. He sat down at my left, put his arm around me, and let me borough my head into his hairy chest. Sighing, he told me that I should find someone to have anal sex with; that that would be a better option than let this divide bring us apart. I nodded, still unclear of why anal sex was such an issue for him. It was clearly more than his obsession with cleanliness (he would clean the house every three days and no shoes were allowed past the rectangular brown throw rug at the apartments entrance) which meant that it stemmed from something traumatic, something unlikely to be fixed easily.
So we made a pact that day. I would go forth and have anal sex with a random stranger.
And two days after, I found myself dressed up and prepared to prowl. I had never actively searched for sex before, so I was both intrigued and nervous. Sex always came to me, even when it wasn’t desired. Especially when it wasn’t desired. Nevertheless, I got dressed and put on my makeup by myself that evening, as my lover was building a guitar at his studio. I finished by putting on the red lipstick I had just bought. Then I licked the inside of my lips, attempted to give a coy wink, failed at that, laughed at my mirrored face, and headed out the door to a nearby bar.
It uneased me to be at a bar alone. I ordered a whisky on the rocks and timidly sipped at it. The bartender gave me a curious eye and asked me what I was up to.
Do you really want to know?
I’m on the prowl for a special kind of sex.
You’re beautiful, so I’m sure finding sex isn’t hard for you.
Well, I don’t feel comfortable finding sex. At all. It’s hard for me.
Well, why don’t you talk to that guy. He’s handsome.
He’s too Channing Tatum like.
You don’t find Channing Tatum attractive?
What type of man do you like?
Tall skinny men with dark long hair who are open-minded, emotional, and artistic.
But also dependable, loyal, and monogamous.
Well that’s specific.
Yeah, I guess it is. It’s unfortunate for me, really.
So I’m not your type then.
I mean, you are objectively attractive. But no, I’m not attracted to blonde muscular men.
Well, if you don’t find someone tonight, then I’d be open.
But I should stop chatting you up.
A tip for you: if you are talking to a guy, other guys are less likely to approach you.
And another tip: don’t be so goddam picky, especially for a one-night-stand.
Oh. Got it. Thanks.
So the bartender left me alone to do my prowling. I sat there in uncomfortable silence and took a sip of my whisky.
It ended up being that I was only interested in one of the guys who patroned the bar that night, and (perhaps ironically or karmically) he didn’t seem interested in me sexually.
By two in the morning I got tired of chatting up random men or awkwardly sipping on my watery whisky (I don’t enjoy drinking, so that whisky lasted the full three hours). I paid the bartender, he extended his offer to help me out sexually, I declined, gave him a generous tip for his kindness, and left.
At home, my lover was already asleep in our bed. I striped and slowly laid my body down onto the mattress, spooning his naked body.
I somewhat slept that night.
The next evening my lover watched as I prepared myself. He told me that I shouldn’t dress up this time since that can intimidate many guys. I took his advice and wore a more causal outfit. But I still rubbed on my new red lipstick. He asked if he could jerk off while I got ready. I agreed. I watched as he touched himself to completion and kissed him once he finished, painting his lips red. After, he smiled up at me and told me that he loved me. I told him the same and left.
My lover was right. More men approached me in the causal outfit.
The first guy who chatted me up I wasn’t into sexually.
The second guy was appalled by my proposition and ignored me the rest of the night.
The third guy was cute, but he was a bit sweaty and dirty for causal anal sex.
The fourth guy was the one, which seemed fitting to me at the time as it’s my favorite number. Like my lover, he had a grungy artistic style, yet was impeccably clean smelling and looking. And- most importantly- open, as he was turned on by my strange one-night-anal-stand proposition. He was also curious about my lover, but I told him that I wanted to leave him out of our conversations. He obliged to this request, so I accepted the proposition to head back to his place, where we began hooking up.
Um, one thing. I have condoms, but no lubricant.
Oh, can we buy some?
The pharmacy nearby me is closed.
Any twenty-four hour bodegas around?
Well, not that I know of. I just moved here two weeks ago actually.
Hence the lack of furniture in the place.
But there don’t seem to be many bodegas in this particular area.
Well, is regular sex an option.
Okay. You’re welcome to sleep over anyways.
That’s okay. I’ll get going.
Should I call you a cab?
No, I can take the subway.
Okay. Well, maybe tomorrow.
Sure. I’ll buy some lubricant.
I ran out of the room, my pants still unbuckled, thinking: that is just like me. I am never prepared for when I want something and seemingly prepared for the things I don’t want. But that could also just be because others are more prepared than I am, so I am prepared for the things they want instead of the things I want.
Still sexually unsatisfied, I took the Q train back home. When I entered the apartment, I noticed a pile of dirty dishes and beer bottles in the sink. It made me happy to see the remnants of his friends’ visit. I favored his friends to mine, since they preferred hanging out at houses to bars, like friends do in places outside New York. I quickly cleaned the kitchen to thank him for his understanding personality before heading into our room, where I stripped down, got into bed and spooned his comfortable naked body as I did the night before. But he was awake this time, anxious.
How was the sex.
I didn’t have sex.
I feel tonight you did something.
I tried to. But he didn’t have lubricant.
Far away. In thought.
I am thinking.
Do you want to talk?
No. Not now.
In the morning I woke up alone. I walked into our living room and saw my lover sitting on the couch. He had tired bags under his eyes. I went over and gave him a tight hug.
I don’t have to do this.
You need to.
What do you mean?
So we can be like before.
But this is stressing you out?
Stressing me out?
Making you stressed. Anxious.
Ah yes. But once you have sex it can be better.
Can you tell me why you are so against anal sex?
But some other time?
I let him cry on my chest before we listened to jazz music and made breakfast together. It wasn’t until six, when my lover went to his studio, that I responded to the guy-from- last-night’s text message. I was on the Subway to his place an hour after. I was there for another hour. I went to a café afterwards to write: Starbucks, since it’s the only nearby café open until 10. When I returned back to the apartment at 10:30 my lover was already in bed. I kissed his neck lovingly and let his body stir at that. Then I took off my clothes.
This time I let him spoon me.
He gave a relieved sigh and we molded into each other the way we used to.
We both slept well that night.
[i] (To clarify further, this wasn’t my first sexual relationship, just my first girlfriend-boyfriend relationship.)