Pegging Straight

Pegging Straight
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Lane Moore
Lane Moore is an award-winning comedian, actor, writer, and musician based in New York City.

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Sex & Relationships

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"Physically, it feels incredible to be filled like that. It's a feeling most guys don't understand."
Despite pegging's recent surge in pop culture, in part thanks to Broad City, the act is still relatively taboo. Is it because people mistakenly assume that straight guys wouldn't be into being penetrated by their partner wearing a strap-on? Or perhaps because it's still relatively new to many people's menu of sex acts? Who knows. In this week's Sex Talk Realness , Cosmopolitan.com spoke with three men about what it's like to love being pegged by women and our culture's assumption of what that means about them.
Man A: Committed to my girlfriend of three years.
Man C: I currently have sex every two to three weeks.
Man A: Porn. I was around 18 years old and had come across a pegging video, and after a few months, I decided to try and penetrate myself.
Man B: Masturbation play led to me being curious about anal play around age 18. Once I discovered how good I could feel through anal play, it was inevitable. I started with butt plugs and slowly graduated to bigger ones, then vibrators, then dildos. Suction cup dildos are probably the best sex invention ever, but they left me wanting a real person behind it, which led to pegging.
Man C: I first heard about pegging when I was 19 via a BDSM-themed Reddit post. I was curious and I wanted to at least try it.
Man A: Physically, it feels incredible to be filled like that. It's a feeling most guys don't understand, because it's not the typical form of sex. Emotionally, it is a whole new type of power dynamic that we both love. The shift in trust and submissiveness, and to be able to open that aspect of yourself to your partner is an extremely liberating feeling.
Man B: It's very intimate. It's nothing like you see in porn. When I get pegged, it's the exact same feelings you'd have during PIV sex, except I'm the one receiving. It makes me feel wanted. There is another dynamic in my relationship as well where I am a submissive and am locked in chastity. Because of this, my favorite part of pegging is submitting to my Princess (which is what I call my dominant). When she is pegging me, it not only makes me feel very submissive, it brings me great pleasure to see what joy and pleasure she is getting out of it.
Man C: What I love about pegging (besides the physical sensation, which is great) is the role reversal and the power switch. It takes a lot of trust in a woman to let her peg you. You have to trust that they won't hurt you or judge you, and there's powerful emotional intimacy in that. Plus, to have someone be into you like that and to get off on causing you pleasure makes you feel incredibly sexy and wanted, which is somewhat unusual for men.
Man A: I brought it up about six months into our relationship. The conversation was pretty casual, as we keep very open communication policy. We can talk about anything. I told her that I was into girls using strap-ons, and she came back with an open attitude but hesitance. She wanted to be able to do that for me, but it took a bit of warming up to it. She was 19 at the time and I was 23.
Man B: I brought it up. It was so long ago, I don't really remember how I brought it up, but I think it was something along the lines of, "Hey, I like things up my butt, you know this, and you know I do it on my own, but do you wanna do it to me?" Which led to, "Sure why not, let's give it a try." Next thing you know, it's a regular occurrence.
Man C: We used a site called MojoUpgrade to quickly get an idea of each other's sexual desires and kinks. It's basically a quiz you take and at the end of it, you get a results page that tells you which activities both of you are interested in (but doesn't tell you which ones only one or neither were into, to avoid embarrassment). We were both interested in pegging, and it turned out it was something she had wanted to try for quite a while. The conversation was very straightforward and positive; we talked about what was attractive about it to each of us and what specifically we wanted to try, as well as different fantasies we had involving pegging.
Man A: She had never done anything like that before. She is my one and only.
Man B: When I brought it up to my Princess, she was ecstatic. She had always wondered what it would be like to "don a cock" and was beyond excited to shop for new toys, harnesses, do research, and of course send me tons of links to "sensual pegging" porn clips and GIFs as well as ideas.
Man C: My first partner to peg me reacted positively and had a definite desire to peg so much so that she initiated most times. My subsequent partner was extremely submissive, and though she agreed that if I wanted to be pegged she would do it, she had no driving desire to do it. She was more interested in the gender play aspect of it, such as cross-dressing and role-play, which I was not very interested in at the time.
Man A: Fortunately, we live in an age that is becoming much more pegging-friendly in media. For example, Broad City did a very tasteful and hilarious episode on it that I would recommend any couple watch if they are interested in it.
Man B: The most important thing in any relationship is communication. If you don't feel comfortable talking about something like that with your partner, you have bigger issues than them maybe not wanting to peg you. The easiest way I found to bring it up was simply talking about how I'd masturbated, toys I used, etc. That led to anal play, which led to me liking to be pegged.
Man C: It's like admitting to a foot fetish or asking someone to choke or spank you in that there's always room for embarrassment or judgment, but if your partner judges you, then it wasn't meant to be.
Man A: The best was my current love who has been fantastic about the whole thing. She brings it up from time to time that we should use the strap-on, but other times I ask. My ex was the worst though. There was no real animosity about it with her, just give a curt "No, thank you" and that was pretty much it.
Man B: The best was, "That's awesome. I've always wanted to try it! Let's do it now!" I've never had a bad response, been ridiculed for wanting it, judged, or anything negative. The worst reaction was probably, "I don't know how I feel about it, but I'm definitely willing to try it because it's obvious you want to try it and I love you."
Man C: The best response to pegging was definitely my first time, but I've been extremely lucky and haven't had any negative responses to it. I had one partner before the one that pegged me that I mentioned it in passing to but their response was lukewarm and nothing ever came of it, but I was never judged or shamed or broken up with over it either.
Man A: We do it about once a month or so if the mood is right. She's the only partner I've done it with.
Man B: With past partners, it was more rare, say once every couple months, but with my Princess ... it's incorporated 90 percent of the time in our sex play. We both enjoy the chastity and pegging play, so we both get what we want. In her words, "Why would I need your cock when you were blessed with such a perfect ass to fuck?"
Man C: As I am currently single, I don't get pegged that often. It's not really something that happens to me for casual encounters. In the past, I'd say it happened in about half of our encounters, maybe two-thirds, which would work out to two or three times a month. However when we got together, it would happen multiple times.
Man A: The fact that I could orgasm without ejaculation or even having the stimulation of my penis. The feeling is nearly indescribable. It's a rush and pulsing wave throughout the entire body. Nowadays it hasn't lost its magic. Usually when people build up a fantasy, the actuality rarely lives up to the hype, but with pegging, it has been everything i imagined.
Man B: Not really, apart from how good it felt at first. I mean I had used dildos by myself, and was hitting my prostate and all that, but when someone else does the thrusting and you get to focus more on enjoying it than moving, it takes it to a whole new level. Beyond that, my orgasms are what still surprise me and always have. And those orgasms, whether I'm locked up or not, if I'm getting pegged, are without a doubt the most powerful orgasms I've ever had. I swear each one is more powerful than the next. Before I got into pegging and found my submissive side, I used to pride myself on giving women orgasms so good their legs would stop working or they'd pass out almost immediately. Now I'm the one getting those orgasms, and holy shit, I did not get enough thank yous back then.
Man C: The first time I was pegged, I was surprised by how much pre-cum I produced. Prostate stimulation causes a lot of it to ooze out. I continue to be surprised by how much my partners get off on the act, sometimes climaxing from it, which is very flattering given that I'm the one receiving most of the stimulation.
Man A: I love being on my back with my legs on her shoulders so that I can look into her eyes and know where I belong in that moment and moreover, who I belong to. I actually don't like doggy-style that much, despite it being the most popularly depicted position. It feels really impersonal and doesn't really hit the spot right. The absolute best position is on my side, looking up with my legs together as she holds my thigh and pounds into me. It's the perfect blend of vulnerability and sensation.
Man B: My favorite position is on my back with my legs on her shoulders. This allows her to go deep while also stretching me and giving her access to all the fun parts. It also lets her go as slow or as fast as she wants, and without a doubt, as fast as possible is my favorite. The pleasure is so intense when I'm getting pounded that my brain literally shuts off and the only noises I can make are grunts and moans. It's amazing.
Man C: Doggy-style is the position I enjoy the most because you can relax the easiest in it and because it puts the other person in a position of power and domination. Cowgirl is nice because you can control the pace and position. Spooning is nice too because you can do it for a while and because it's easy to give a reach around, but it's a little awkward. Missionary is definitely the least enjoyable because I am rather tall and inflexible so the whole thing is painful and awkward, which is too bad because I'd like to see my partner's face without having to crane my head over my shoulder. Also, generally grabbing of my hair or throat or clawing my back is nice.
Man A: That they're secretly gay. It's absurd to try and classify it that way.
Man B: I'd say there are two. The first being that it makes you gay. I don't know where this came from, but it just doesn't make sense. To anyone that says this, I say, "Enjoy your mediocre, boring orgasms for the rest of your life." The second would be that it's dirty. Anal play is anal play. We all know what goes on back there and accidents happen. But so long as precautions are taken (watching what you eat prior to playing, staying regular, eating healthy in general, and doing a quick clean beforehand), they can be avoided. And even if were to have one, we're adults and shit happens. Get over it.
Man C: The biggest misconception is definitely that liking pegging makes a man gay or unmanly.
Man A: This goes for both sexes: Be honest and be open. You can't say you don't like something you haven't tried. Also use lots of lube. if you think it's too much, you're probably wrong, because if you're new, you need lube.
Man B: Do it. If you want to try it, try it. Talk to your partner and if they're not open, that's OK. Don't force them. If it's a healthy relationship, things will work out. If you're single, join a fetish or BDSM community. I can guarantee there's someone in your area who's willing to try it, or already likes it. The point is, why would you deny yourself pleasure just because society says it's weird or taboo? That's just silly.
Man C: My advice to both genders would be to take it very slow at first and communicate openly during it to prevent too much discomfort.
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Olivia Cassano Wednesday 22 Nov 2017 10:00 am
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If 2017 was the year of eating ass , 2018 will be the year of pegging .
Chances are you’ve already heard of it – but if you haven’t, pegging is, in most cases, a sexual act where a straight man is penetrated by a woman wearing a strap-on dildo. And no, it doesn’t involve a peg leg.
The word ‘pegging’ elicits responses of shock and judgement in many, and it might not be for everyone, but as with all sex, it is simply about pleasure.
Pegging has been around since the dawn of time (anything we do, rest assured, the Romans did it first) but it wasn’t until the 1998 release of sexologist Carol Queen’s sex education video series Bend Over Boyfriend that the act was given more attention.
But despite its recent surge in pop culture, in part thanks to shows like Broad City and movies like Deadpool, the act still remains largely taboo.
Many people still mistakenly think that if a straight man enjoys being penetrated, it makes him gay (it doesn’t) or unmanly (utter bollocks).
Anal pleasure for straight men has always been a taboo, partly due to this misguided, patriarchal idea of emasculation, and partly due to an ‘ew’ factor.
But letting internalised homophobia and gender roles get in the way of mind-blowing orgasms seems a little bit silly, doesn’t it?
After all, the prostate – the walnut-size gland found under a man’s bladder and easily accessible via the anus – is essentially the male g-spot. A magic pleasure button, if you will.
Aside from the intense physical pleasure, one of the best aspects of pegging in a cis, hetero relationship is that it inverts the traditional framework of gender and sexual roles.
According to a 2012 study published in the journal Sex Roles, clinging to traditional gender roles could make us feel less comfortable between the sheets, and research by sexuality educator Dr. Charlie Glickman also shows that straight men who had tried pegging were more in tune with what their female partner needed from them during penetration.
So pegging could not only give men a more intense orgasm, but it could possibly teach them a thing or two on how to pleasure women; basically, a win win.
When you think about it, pegging is still standard heterosexual PIV sex because the bottom line (pun intended) is putting something inside a hole. It simply works the other way around.
Indulging in something that is taboo helps chip away the stigma, which helps people get over their insecurities about what turns them on.
Talking about all kinds of sex, urges and curiosities is the first step towards a fulfilling sex life, and no one should feel ashamed to discuss their sexual preferences.
And because sex should always be a judgement free zone, here, seven straight men share their experience with pegging (anonymously, because society is still a little prudish). To quote Ilana from Broad City: ‘Anal’s on the menu’.
My interest for anal play and pegging didn’t develop until my 30s.
During my 20s, I was more interested in having different sexual partners and more ‘traditional’ sex.
However, as my relationships started to become more stable, I found that pegging added an extra dimension to my sex life.
I was also very curious about prostate stimulation that is mentioned constantly in many sex articles, so this became something I wanted to try.
It’s no different to admitting you having a fetish.
Some people are into feet and others like to be spanked or choked and pegging isn’t any different.
It might be a bit awkward to talk about at first but if you can’t openly talk to your partner then they’re not meant for you.
It was my ex girlfriend’s idea, she read about it and brought it up with me.
I was skeptical at first, but even now that we’re not together anymore, it’s something I do with my new partner.
We don’t do it very often but even when we just have regular sex, she’s a lot more assertive, which I think is really hot.
I suffer from erectile dysfunction so the allure of pegging was that it took the focus off the penis.
The prostate is basically the male g-spot so it means men who struggle with staying hard can reach orgasm without any penis stimulation at all.
Once I realised how good it fel
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