An Open and In-Depth Chronicle of a First Time Pegging

June 22, 2015
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An Open and In-Depth Chronicle of a First Time Pegging
Artwork: The Cheeky Dragon

Every year many of us set out to try uncharted things, live new experiences and conquer fears. And while many times we chicken out or indefinitely put them off, there are times that present themselves on their own, with no bullshit bucket list to answer to.

This story refers to an event from last summer. There are several reasons why I didn’t write this then, but I think the clearer one is that even after being pegged — and having a positive experience — there’s still something remarkably vulnerable about it. Sitting here and writing this feels like over-sharing, which sounds weird if you know me, because I’m usually quite frank and open about a lot of deeply personal stuff. Boundaries have a lower register around me. I’m used to going on stage and talking about extremely personal things on a regular basis, but stand up comedy is a much different context. Somehow talking about truly intimate and emotional things in my life comes naturally. Being fucked in the ass, though? A little less naturally!

One warm summer night I was hanging out with a friend and talking about different sexual fantasies of ours. We both work and write extensively about sex, so it wasn’t anything out of the ordinary. We met through work stuff, as she’s a feminist pornographer and I was doing a behind the scenes piece on her porn shoot, but we became good friends, and bonded through our own perceived normalcy regarding our jobs.

She told me that pegging a guy was high on her list, and although it wasn’t necessarily one of my dream scenarios, I was curious enough to give it a shot. In an unexpectedly brave statement, I found myself saying, “I’d let you peg me if you want.”

And just like that, ladies and gentlemen, I had made an appointment to get fucked in the ass.

I’m no stranger to anal play and have long enjoyed fingers and tongues up there. For any homophobic douchebag who refuses to accept it: Massaging your prostate feels awesome; deal with it.

In my experience, though, anal sex comes with trust. Rarely — except for some anal enthusiasts, God bless their hearts — will someone let another person fuck them in the ass without a minimum amount of trust. It’s a very intimate act that evokes a lot of vulnerability.

I’ve had anal sex with my share of women before (never receiving it, though), but I had never been anybody’s first anal experience. It had always been girls who were into it already and things came naturally. I asked a few female friends about their first times doing anal, and the overall response was expectedly unfavorable. Many guys get pushy about it. Many times there’s no lube around. Most times nervousness and anxiety sort of killed the mood. This wasn’t really helping me prepare for anything; I just needed to relax about the uneasy details.

Size was a big deal to me. The notion of a thick, giant phallic thing going inside me made my asshole contract in fear. And I didn’t know what to ask for, so I kind of went with a “nothing bigger than my own” policy, which I found fair. My friend pointed out that girls don’t get to choose what dick size they get; but hey, given that we do have a choice in this case, why not embrace that?

She agreed and the next day she purchased a “starter” dildo with a strap on. I remember feeling kind of wooed about her spending money on something that was going to be used specifically to take my anal virginity. A strange thought of matriarchy popped up in my head, which I sort of chose to ignore and not over-think.

In a way I felt very lucky, because a) I liked and trusted her, b) I had a say on the size of the dildo, and c) the person who’d be pegging me is a girl, who knows what it’s like to be fucked in the ass. I can’t emphasize this last part enough. A full understanding of what it’s like to be on the receiving end could actually prevent a lot of boneheaded moves that most guys seem to be doing, and probably the biggest cause of unsatisfactory anal experiences.

I stopped on my way to her place to get weed and some chocolate — because having well tested pain-soothing items just seemed like the right move. I showed up at hers, and even our greeting felt a little weird. We were both trying something new, for sure, but there was something about our dynamic that felt a bit off.

I went into the bathroom and washed my face. I looked at myself in the mirror with this weird feeling of both excitement and dread that made me feel like a 16-year-old girl on prom night. I laughed this off and came out. We smoked a joint and hung out on the couch like we would any normal day. It wasn’t just my asshole that needed lubrication; the social context of this meeting needed it just as much. Being relaxed was important to both.

“So, ready?” she asked with a smile. I didn’t know the answer to that. I mean, yeah, I was as ready as I was going to get, but something inside me was just dying to procrastinate the fuck out of this one. “Let’s smoke one more joint first, yeah?” I asked a bit shyly. She nodded, keeping the same smile.

I kept thinking about my first time having sex, as a teenager, and I don’t recall being as nervous that time. Perhaps because as guys we assume that putting our dicks inside a vagina will immediately feel awesome, whereas putting something up our asses will be met with pain. Sometimes human responses are more about immediate reactions to our fears than we’d like to admit.

We started making out and fooled around for a bit, but there was something odd about it; it kind of felt like we were stalling, more than getting ourselves in the mood. I realized that we didn’t really know where to start, which is quite humbling for people who write about sex for a living.

Sex is one of the very few activities in life that I’m extremely confident about, and here I was trying to think of how to position myself, and how I was supposed to act, and whether my nervousness was too obvious or awkward. It’s like this wasn’t me anymore, at least not the sexual-self that I knew. This came from a totally different place.

Using what in hindsight was clearly an obscene amount of lube, we were finally there. Me on all fours, while she adjusted the strap-on and lubed her hands and dildo up. And while I felt a little silly with my “well, I guess we’re doing this now” attitude, there really was no other outlook at the moment.

But if we felt like rookies before we started, once we did, the humbling moment would sink in — nope, not intended — even more. Considering the dildo is not actually a part of her body, I felt comfortable enough to ask a question you ladies should avoid at all costs: “Um, is it in right now?”

It sort of was. Angling was more complicated than we originally predicted, as our height difference — not to mention our complete inexperience in the other person’s role — required some extra pillows. She was being extremely gentle, which I was very grateful about, but it also made the moment a bit more tense for me, because I kept being a little worried about it.

We switched positions and got me on my back — a position I tend to enjoy quite a bit when I’m the one fucking a girl in the ass. It’s super weird to be having this very intimate moment with someone very familiar to you, yet so out of your comfort zone. My legs were pushed back, and though it turned me on to see her take charge and enjoy herself, our clumsiness, the summer heat and the slippery mess that we created when we seemingly thought it was a good idea to lube things up to the max, were getting in the way of the fun. We decided to take a break.

If you’ve never had an asshole full of lube and tried walking around with it, let me assure you, it’s a little uncomfortable! Resuming sex just meant not dealing with the awkwardness anymore, so we went back for it, this time I was kneeling against a chair, on the floor, while she took me from behind. This time the height was perfect. The pace was perfect. Fuck, the chair was perfect.

I wasn’t in pain; I couldn’t feel it very much, to be honest. This was, after all, a beginner’s dildo: Very thin at the top and not that long. I asked how deep she was, and to my surprise she said, “It’s all in.” I couldn’t believe it: I had a dildo up my ass and I barely felt it!

She suggested we could use the Macchiato, if I wanted. This was her favorite dildo, a true penis-looking one, and slightly bigger than me, which scared me a little bit. But I wasn’t going to let this ruin my newfound anal hubris. Bring on the Macchiato!

Now, this I could feel. She started very slowly again, and gradually sped up a little. New sensations sprung. I started getting harder, and having this euphoric tingle that came without anything making any contact with my penis. I could feel her bracing on my hips and panting over my shoulder as the base of the dildo kept rubbing on her clit.

It came out of me for a second, and somehow the idea of getting it back in took a second to process. This type of intensity was new. I asked her to stop for a minute. I also inquired about how deep we went this time. “All the way in!” she replied. That took another second to process.

My goodness,” I mumbled, “I turned out to be a size king!

We laughed — and sort of spiritually high-fived — in celebration, and went back for more. I could feel her get into it, but not in the same way she would when we’d had sex before; she was channeling this other person, and so was I.

I don’t remember feeling that vulnerable in a long time, and definitely never as much in any sexual context. The role reversal felt extreme, yet really hot. I could feel her fingering herself while she penetrated me and the thought of her losing herself this way was borderline inebriating for me.

I could feel her powerful orgasm while she collapsed over my back, and every insecurity I had about this was long gone. I was really turned on at this point, and we decided to switch back to our natural roles.

All of a sudden, as I’m fucking her from behind and holding her tightly, it was like we were back in the roles we knew we’re good at. The comfort zone was back. We were sexually skilled again; we could tease and move confidently, but it’s safe to say the moment we had just experienced was still firmly alive in both our minds. We both came as we soaked the moment in.

I didn’t come anally. I didn’t have to, either. I don’t think my goal was ever the orgasm. I was approaching this as a new experience. There were no clear expectations, just the idea of trying something I’d never done before. And boy, was that accomplished!

I feel like my whole approach to anal sex changed that day. In fact, a couple of weeks later, while having anal sex with her (this time with her on the receiving end), I found myself being extra careful, thoughtful and delicate, almost to a fault. Nothing will ever give you someone else’s true perspective until you see it for yourself.

You can read her own side of the story on her blog, which has a couple of extra details that are better to hear from her. It was really cool to see her embrace the role reversal as much as I did, and to this day I think it may have brought us a lot closer.

A few months later she was leaving Barcelona and was having a farewell party at her place. I was doing stand up that night and arrived later, when everyone was already there. I’d never seen this studio apartment with so many people. I sat on the floor, wherever available, and hung out with the other guests. After a while, a French guy who was sitting on that now infamous chair asked me if I wanted to sit there for a bit instead of the floor. “It’s comfortable,” he assured me, “Have you sat here yet?”

I smiled, closed my eyes and thought back to that happy, sweaty, lubed up mess we were. “Something like that, dude. Something like that.”

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