Passionate Pegging

Passionate Pegging
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By Zachary Zane Published: Dec 9, 2020
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Zachary Zane is a Brooklyn-based writer, speaker, and activist whose work focuses on lifestyle, sexuality, culture, and entertainment. He was formerly the digital associate editor at OUT Magazine. His work has been featured in Rolling Stone, Washington Post, Playboy, and more.
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"What I like most about pegging is the intensity of the orgasm for my partner."
It makes a lot of sense that some men like being pegged (aka, having a woman enter them using a strap-on dildo). Guys have a prostate—commonly known as the male G-spot —which is a walnut-sized gland 2-3 inches inside the anus. The prostate is full of nerve endings, and the right kind of stimulation can lead to powerful, full-body orgasms . Enjoying prostate stimulation has nothing to do with being straight, gay, or bisexual—it's simple human anatomy.
But why do women like pegging men? What do they get out of it? They're not experiencing any internal or clitoral stimulation , so unless they're using a toy at the same time , it's unlikely that they'll orgasm through pegging a man. Besides, how does one even get into pegging? Did they just ask their boyfriends, "You know how you like sticking it in me? Well, I think it's time I stick it in you!"
Well, we spoke with 14 women who love to peg dudes to find out.
Rose: "My boyfriend expressed an interest in wanting to be pegged. I was very supportive but also intimidated because I don't have a lot of experience with ass play on men. But I went ahead and bought a 5-inch strap-on. It felt really strange to wear the dildo, like, awkward with this purple appendage protruding from my pelvis, pointed at my boyfriend’s poised ass. Once the dildo was inside, I checked in with him to make sure I wasn't hurting him, and he replied, 'Are you in all the way?' After I began thrusting, he said, 'I don't think this is working, it's not big enough!'”
Amber: "My first pegging experience was both intimidating and exhilarating. It was with a long-time sexual partner who knew he really wanted it. I was so apprehensive because I didn’t understand what pleasure I would get out of it, and I was super nervous because I’m typically more of the submissive partner. He finished after two quick pumps, but the power I felt in those few seconds rocked my world."
Kellan: "My first pegging experience was one of the most intimate sexual experiences I've ever had. It was with a close friend/lover, and we had been talking about trying it for a few weeks, and I felt completely comfortable and open with him. After a couple of glasses of wine, I put on the sexy, leather harness and black dildo along with a Victoria's Secret corset top. I don't think I've ever felt sexier."
Shira: "I was young; it was almost 20 years ago, and it was exciting. My boyfriend at the time had gifted me a strap-on set for my birthday and asked me to peg him."
Daya: "My first pegging experience felt like coming into my body for the first time as a vulva-bodied trans male."
Kelley: "My first pegging session was with a long-term partner, so we were very comfortable with each other and took it slow. He had been using it by himself already too so it wasn't completely new to him."
Ashley: "My first pegging experience was actually with one of my sex educator colleagues, which was great because he was very clear in his requests, and offered me tips—including the importance of using lots of lube."
Crystal: "Overall, incredibly positive. I was in college and my boyfriend and I had been planning it. We took our time and just had fun with it. I used a double dildo we bought specially for the occasion. I had one of the most amazing orgasms of my life from the g-spot stimulation while I was pegging him."
Lola: “It was very communicative, sweet, and slow. I was more concerned about his experience than my own. The dildo slipped out of his butt a lot without realizing it though. It was quite frustrating because we had to keep starting and stopping.”
Allison: “My first experience with pegging was also my first time [having sex] with my partner. At the time, I identified as a lesbian, and I had clocked a lot of time wearing a strap-on, but he was my first time using a strap-on with a cisgender man.”
Aja: "My first experience pegging was in a queer threesome with my oldest friend. My friend being a massive sub got dommed by both me and their girlfriend."
Rose: "Aside from my boyfriend wanting it and my wanting to please him, I really wanted to know what it was like to fuck someone. I've always been a sub and don't really have any domme energy in the bedroom, but I was curious to know what it feels like, to feel what the men who fuck me feel."
Amber: "I had been hooking up with this partner for a really long time and we had explored several different fantasies and kinks together, so I figured if I was going to try pegging, this was the way to do it. And he really begged to be pegged, which in itself, was quite the turn on."
Kellan: "I wanted to know the sensation of being on the giving end of penetration."
Shira: "We had done anal play on each other, and it gave us both all the orgasmy feels. Once I first fingered his ass, I was very excited to see what else could go in and make him cum."
Daya: "I first tried pegging because my partner and I were exploring his bisexuality at the time. Although his previous girlfriends had engaged in prostate play, he had never had a partner open to his desire to be penetrated by a penis."
Kelley: "We're both bisexual, so to me it's like of course, we tried it, but I hope different types of partners would also give it a chance."
Crystal: "I was in a super great relationship where we were young and a had strong sexual compatibility. My boyfriend had been fucking me in the ass and started expressing curiosity about what it would feel like if I fucked him. We watched some pegging porn and started off easy with rimming and fingers for a few weeks, worked our way up to butt plugs , and only then decided to try full pegging."
Jess: "I really decided I had to try pegging when my husband and I started seeing another bi/bi male/female couple earlier this year. The other man was very into my husband, and we had never explored our bi male fantasies . He had never wanted a guy to fuck him before this moment. It really turned us on. We are both big proponents of trying new things from both sides of the spectrum, so where better to start than at home... bent over the couch in the living room."
Allison: "Prior boyfriends and I had discussed pegging, but we never got around to gearing up and trying it. I’m a dominant-leaning switch , and I’m attracted to receptive, switchy male partners. So pegging was always intriguing to me, even from a young age."
Aja: "I've known my friend for six years now, and we're both very sexually open and positive people, so we had been talking about me domming them for years. So it was kind of an inevitability."
Annie: "I'm a naturally dominant person and something about penetrating a guy like that just really turned me on. Also, as a queer woman I love being with men who are comfortable expressing themselves sexually in ways that may go against gender norms."
Rose: "Honestly, the best thing about the whole experience was that my boyfriend felt comfortable enough with me to tell me he wanted it. It showed how much he trusts me. I also enjoyed the sense of control and power."
Amber: "It’s the most intimate source of power I think someone can experience. Sure, you don’t get the same sensation as someone with an actual cock, but the connection and vulnerability felt in that position is incredible. I also noticed an immediate sexual confidence boost that I think has translated into my regular day to day life."
Kellan: "The act went fabulously, so much so that I actually came while fucking him! What I loved was how in control I felt, how sexy I knew I looked, and when I wanted to, how intimate I could make the situation. I was turning myself on!"
Shira: "I like the pleasure that they receive, the power exchange, and the feminization of the bottom while I wear the strap."
Ashley: “I love that it makes me feel powerful in a whole different way. I also appreciate the vulnerability it takes for my partners to ask me to penetrate them, especially given the cultural taboos.”
Daya: "Pegging is an important part of my trans male gender expression. I prefer strap-ons with a double-ended dildo so I feel that the penis is attached to me. I love the freedom to be fluid with my partner and give him/her/them pleasure through surrogate male genitals."
Kelley: "I like pegging because I like fluid roles with a partner in and out of the bedroom. What I'm attracted to in men is an absence of fragile masculinity. Pegging can be considered a symbol of that, so yeah, it's fucking hot!"
Crystal: "Honestly, everything. If I had to break it down, I would say that I enjoy how it can be deeply intimate. The male partners I have pegged have all expressed a deeper appreciation for the art and skill set of receiving, and in that moment, I feel more seen, understood, and appreciated. It’s easy to think (especially in straight culture) that bottoming is easy , but once you have a dick in your ass, you learn real quickly that it can require lots of emotional and physical release. In this way, I feel safer and more understood by men who have bottomed."
Lola: “I definitely have penis envy, so wearing a cock is exciting. I like experiencing all the aspects of sex and being the penetrator is different and fun. I also enjoy giving men a sensation that may be new to them and walking them through that experience.”
Amanda: “I love playing with the shift of dynamics and creating a new way to connect with my partner. Selfishly, I also love the feeling when I can confidently put on and stroke my own 'dick.'"
Jess: “What I like most about pegging is the intensity of the orgasm for my partner. I mean, if anyone hasn't experienced giving a prostate orgasm firsthand you are seriously missing out."
Allison: “Pegging is one of my favorite activities, hands down. I love being in a position of control, and I love delivering an intense and connected experience. I like how pegging can help some men drop into sub space and relax into powerful sensations.”
Aja: "I get a lot of satisfaction out of making someone utterly melt with pleasure and ecstasy, both from the feeling of power it provides me, and just from making someone a quivering puddle. Pegging and prostate play with the right partners can provide all of that."
Rose: "Never be afraid, it's just another fun sex act! If she's not into it, that's cool, but never be afraid to ask about pegging or anything else. Open communication and trust are so important, huge, and if you and your partner don't feel comfortable discussing intimate sexual acts, you are probably fucking the wrong person and should find someone you can be yourself with!"
Amber: "Just ask! I’ve been pretty open with my friends about the experience and there are so many of them who would welcome the opportunity. I think getting over the idea of it not being a 'masculine' desire is the first step. Pleasure is pleasure, and we all deserve to explore as many ways of achieving it as possible!"
Daya: "Like all things anal, build your way up! Tell your partner you are interested in exploring prostate play and start off with rimming or a finger. You might be surprised! She may even suggest graduating to pegging."
Ashley: “Take a deep breath and make a request! Use this article as a jumping off point; send it to your partner and say, 'Hey, this seems interesting, would you be willing to explore it together?'"
Lola: “Don’t stress right off the bat that they have to be the one to penetrate you. State that it’s a thing you’re into, and it’s up to them if they want to partake. Let them come around on their own curiosity!”
Jess: “A lot of men worry an interest in pegging must mean that they're bi or gay and the fear of asking comes from that place, but try not to get hung up. When I want to try something new with my husband, we both read a lot about it. So it might be an idea to try sharing this article with your female partner and asking if she'd want to give it a whirl."
Allison: “The stigma against male [anal] receptivity is real, and it sucks. I think the best thing to do is start by exploring anal together using plugs or other toys. Pegging can be an intense sensation, and I’ve seen women get too carried away by the excitement of wearing a strap-on.”
Aja: "I would say start how you would with any kink/fetish or strange bedroom request, and openly communicate your desires to your partner. This can definitely be harder in new relationships, or relationships that don't have a precedent for these kind of discussions, but it becomes normalized when you do it more."
Annie: “Watch some porn together and choose specific clips that include pegging or anal play and vibe it out. But also, just ask! Your partner should respect you for making a desire known, and you never know—they may want to try it too but have been too afraid to ask."
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