Two confessions about the first time I had anal sex:
- It was in the raw. Unprotected anal sex.
- It was the only time I’ve received anal sex.
I think the thing that made me want to fuck JR was his black and white thinking, which was also what made him get under my skin. I hated how he split the world. And how he would use it to control me by pushing me into friend or foe depending on what side of a specific line I was on.
I wanted to dominate it out of him, hoped that just fucking him would teach him better, that being inside me would show him something new, that pussy would prove my point. Pretty sure it never worked.
I use his real name, because if you use initials that are super fucking common and even used by such a popular 80’s TV show that you get asked all the time if that’s why you have that name, well, that’s what you get. No one will know who you really are, JR.
Even if I tell everyone that you were from Santa Rosa, California, which is also where The Plant Whisperer is from, but they don’t know each other, I haven’t met The Plant Whisperer yet, and when I do meet him I bring it up, but The Plant Whisperer hasn’t heard of any of the bands that JR played in, even if one of them opened for Green Day once.
I met JR on Craigslist, back when that was a seedy thing to do. I didn’t think our sordid origin mattered much for our fuckbuddy connection, but hey, he’s also the only guy that ever fucked me up the ass.
JR was your classic USAmerican punk rock musician, bartender, motorcycle riding, leather jacket wearing, vinyl collecting cool kid. Not that handsome, not that great of a body, his sexiness rode in the boiling repression just simmering underneath his cool, collected, slightly stylized persona.
Ulster Scot background, rough childhood, smart and intellectual, but no formal education because he’s been supporting himself for too long. Independent as can be.
JR was good at sex. He knew his way around a human body, and wasn’t shy about it. Where to grab and hold, and how to move his own body around a bed. He learned well, he communicated well, and he gave good oral, even if I did have to remind him to be gentler almost every time. He wasn’t explicitly into anal sex. Anal sex wasn’t a conversation we ever really had. Certainly never talked about unprotected anal sex.
JR liked to fuck, and I liked to tap a brutality to him that showed up outside of his careful communication. Showed up when I would edge him, surprise him, push him. I liked pushing him off kilter.
Especially when it bent his rigid lines of consent.
I learned more than once that I’d put myself at risk to make him break his own rules.
I come over to wake him up in the morning. He works until 2am and sleeps until noon, and I work on my own hours, so early afternoon trysts work well for us. He wakes up early and unlocks the door and then goes back to sleep, and I wake him up however I see fit that day.
This day it’s not with a blowjob, one of our favorites, but it only works if he’s sleeping naked and today he has a pair of boxers on. Instead I quietly enter his place, furnished and decorated with thrift store wares and a minimalist retro feel. I strip and slip into the bed with my back to him and he snuggles up to me, still sleeping.
I nudge my ass into his cock to test if he is hard. He isn’t. Rolling onto my back I pull his top leg over me, relishing the warmth and weight of it on my hips and belly, and slide my hands under it to pull apart my lips. I dip a finger to get it wet and then play with my clit, wasting no time.
At my second, he’s taking off his own boxers and I’m scissoring my leg over his and he’s thrusting into me with no condom, which is a huge no-no for him. We haven’t said anything to each other yet.
My breath comes in sighs and gasps. Unprotected sex feels really good. He’s never felt this good. Notice so much compassion for him blooming in my heart. I hate condoms. I don’t say anything, I don’t want it to end, I don’t think about it. He’s just a cock.
He fucks me on raw instinct and luckily pulls out on raw instinct too and comes on his top sheet.
And then, sweetly, he explains that he wasn’t awake and that we really should always use a condom.
I agree. Of course I agree, rationally. But emotionally, I’m smug af because fuck him for creating boundaries after the fact as a method of control and the sweet conversation of blame.
And, it felt good.
Now it’s another day, in my place, not his, with its vintage rockabilly feel. It’s my place, back when I had a place.
My place with its California King size bed and its adjacent bathroom. My place that’s fun to fuck in.
We’ve just had sex. JR went down on me until I was dripping and juicy and could not easily come anymore and then jumped inside and came before he wanted to. I’m a melty puddle of satisfaction from the copious orgasms still and he’s tossed the condom off and washes up a moment.
When he comes back in the room I am lying face down on the bed with legs slightly spread and he takes that as an invitation to lie on top of me, which is somewhat how I meant it.
But if I meant it, surely I meant for him to get hard again, hard as the edge he tries to project, and to put a condom on and slip inside my pussy from behind, unable to control the urge to be inside me again.
Which is both not what I get and exactly what I get.
In afterglow, with him on top of me, my hips curl up towards him ever so slightly. Almost only in energy, not in physical movement of the body. I feel his respond with just the slightest jog.
I feel his cock lengthen. Subtle movement, but it’s resting between my ass cheeks and I can feel a micron of movement there. Sensitive skin.
And slick. I arch into him just a little more and with the faint hint that I’m doing it on purpose his cock pushes on its own just past the fringe of hair and lips and into a pool of my wet juices mingled with lube from the condom and his spit from a marathon of lapping me.
My hips search for a little more contact, coaxing the head of his cock further between the place where my lips become cheeks.
He now moves his hips, and his cock against my taint slips up instead of down, until the tip of it rests on my anus. I feel him freeze in “oops”.
I’m curious. What will he do?
I flick my hips backwards in a way he’d never feel if it didn’t press the head of his semi-hard cock against me. Sensitive skin.
He feels the tease. He pushes. I push back.
He’s so slippery and I’m so lubed up he slides inside my ass just a tad and with that he’s hard as a rock and moaning audibly as I groan. I ring him tightly, after all, I’m a virgin. Gently, slowly, he rocks into me deeper and deeper, opening me up to a point. I’ll take his head, that’s it. I squeeze and polish it for a moment. His cock is warm and glossy and feels good in a distant and scary way. Sensitive skin.
But he loses patience and he drives deep into me in two strokes and I move to stop him because it feels too much, too soon, and there’s been absolutely no conversation, but he’s howling and coming so hard into me and it’s over in just the right amount of time and I realize that those strokes were his involuntary thrusts as he came. They just felt so big.
He’s not an easy man to overwhelm and he’s been overwhelmed.
“Wow.” he keeps saying.
After cleaning up I come back in from the bathroom and cheerily announce
“You popped my cherry!”
“You’d never had anal sex before?” he asks, with terror in his eyes.
I smile and shake my head no, like it’s innocent, but it isn’t. On the inside I love seeing the range I just put him through. Made him break so many of his rules, and I relish the look on his face as he realizes he just fucked a virgin in the raw. Ass or not, it’s a powerful narrative.
And when he tries to do so, a month or so later, wrapped in latex and pushing at the entrance to my backside after I’ve offered him my ass in the air for other purposes, I pull away.
“I can barely take that fucking condom in my pussy.” I growl by way of explanation. He nods. He knows.
The only reason it worked and was hot is because we did it unwrapped and unsafe.
P.S. Other than thinking about JR every time someone mentions anal sex, I never thought I’d think about him again until I met this guy David at Burning Man and when we got to talking we realized that we’d lived two places in common and had three friends in common. One of them was JR.
Another was Marvin the Merry Macrobiotic, who you can read about in my first book, Down and Out in California