One of the more difficult parts of growing into your sexuality isn’t how often you’re having sex, the type of positions you’re trying or how intense your orgasms are. As you age and eventually find a woman who you connect with not only physically but emotionally too, the more challenging sexual experiences are found in accepting yourself and what turns you on. With that comes experimenting with your fetishes, without worrying or being anxious about what they say about your as a human, a person, a partner or a man. If you’ve recently found yourself interested in pegging, you might be nervous about your own sexuality, but as experts note, a desire to be penetrated doesn’t change your sexual preference. Instead, it’s just as it sounds: a way in which you like to be touched, fondled and caressed.
Bringing up this subject to your girlfriend or wife could be tricky, so it’s important to have all the facts and truly understand this fetish before venturing into an unknown land with your leading lady. Luckily for you, we did the dirty research for you and have everything you’d ever need to know about pegging — from what it means and its history to how to incorporate the practice into your sexual routine without wrecking your relationship. Here’s the skinny on being penetrated as a heterosexual man:
2 The History Of Pegging
3 Misconceptions About Pegging
4 Why Does It Feel Good?
5 How Do You Bring Up Pegging With A Partner?
6 Pegging Positions
6.1 Doggy
6.2 Missionary
6.3 Cowboy
7 Final Things To Remember
Where to Buy?
Harnesses & Strap-On
Anal Plugs
Anal Lubricants
1. What Is Pegging?
The word itself is intimidating on its own, especially if you’re a man who is used to doing all of the thrusting and pumping to a woman, instead of vice versa. But as Hunter Riley, sexual educator explains, the idea and physical act of being penetrated is exciting and 
arousing because of all of the nerve endings in a man’s anus. “Pegging is a sex act where a woman anally penetrates a male partner with a dildo or strap-on. It’s a very popular sex activity that many heterosexual couples are exploring together. While there is still stigma around anal play, and maybe especially for heterosexual men, it’s one of the most common questions I get while talking with customers at Self Serve,” he explains. “I’ve heard some people also use the term pegging to describe strap-on sex in a non-hetero pairing. While different definitions and practices of what pegging is may vary, it’s typically thought of as anal sex between a man and woman, where the woman is using a dildo or strap-on.”Though still the same act, sexual commenter Colleen Singer notes the experience can sometimes be referred to as something a little more playful…but perhaps more descriptive. “Pegging is also sometimes referred to as ‘Bend Over Boyfriend,’ or BOB for short,” she explains. “This term originated from the production of the first educational video for straight couples about male anal penetration.”
2. History Of Pegging
While the concept of having strap-on sex might seem foreign and risque to you, the practice of using another object to have intercourse or ignite orgasms has been documented for several thousand years. Angie Gunn, L.C.S.W, sexuality expert at TalkSpace.com, says the practice itself has been called many names over time, but historians can find indicators from China to Europe. “Strap-on sex can be traced back to as far as 12,000 years ago in ancient China, then later in Greece, France and England. Depictions and accounts primarily refer to female-to-female use,” she explains. “However it’s likely heterosexual women and men with erectile challenges also used strap-on dildos throughout history.”The conversation about pegging started in the 1970s, when pornographies introduced short clips of women penetrating men anally, Gunn says. Then another upswing in this type of sexual activity happened in the early 90s, when men discovered just how powerful an orgasm stimulated via their prostate could truly be. “In the 90s the concept of prostate play was coming out of the shadows. Instructions were everywhere on how to massage the prostate with either a finger or toys. It was called the male G-spot, the A-spot, and even the P-Spot,” clinical sexuality educator Paul Nelson explains. “Men’s magazines wrote articles on it, sexperts extolled its virtues, women were asking each other about it — soon, ass play for men began to enter the fringes of vanilla sex. Pegging is the next logical step in this sequence. Once men discover anal and prostate stimulation, most of them love it.”
But even so, the name wasn’t made official until 2001. “People have been using the term since the 1990s, but it was popularized when Dan Savage ran a contest in his ‘Savage Love’ column in 2001. The contest was created to address the absence of a widely adopted term for this sexual practice that seemed to be gaining in popularity (or at least more people were talking about it),” Singer said.
These days, pegging is more common than you’d think, as Nelson shared: “I once stopped at a sex super store in the Midwest and talked to the manager to see what was trending in sales. He grabbed a pegging set off the wall and said ‘The new millennium is all about pegging. I can’t keep these in stock!’”
3. Pegging Misconceptions
Though it’s widely documented that most men report a higher sex drive than their female partners, it’s often women who feel more liberated to try out-of-the-ordinary positions, roleplaying and S&M. This can be due to how some men are taught to suppress their sexuality or be ashamed of their inclinations, with some of this false education coming from parents, friends or mentors. A heterosexual man might not even be okay with anal finger play because he’s afraid that, by enjoying it, he’s somehow a homosexual. Sex experts confirm (again and again) this is not the case, at all.
Here are some of the greatest misconceptions:
Pegging Means You’re Gay Or Bi
We’ve reiterated it, but let us say it again: the biggest hurdle to a man embracing (and thoroughly enjoying!) pegging is his own mind. When you let yourself be free and release any negative connotation you have toward anal play, the more fun you will have in your sexual routine. “Despite more mainstream acceptance of pegging, there is still some reactivity at times from the heterosexual community related to anal penetration of a man. Socialization and moralism shames the presence of any anal play by a man, assuming it is always homosexual in nature,” Gunn says. “To clarify, your sexual orientation is not indicated or determined by the types of sexual behavior you engage in, but by whom you engage in it with.”
Riley also adds that a big reason why this stigma still exists is because of our homophobic society that still isn’t clear on what it means to be gay. “Mainstream culture tells us that ‘real men’ don’t put things in their butt because that’s what gay men do, therefore if you want to be a ‘real man’ you aren’t allowed to enjoy anal stimulation,” he says.
Pegging Is Just A Power Play
Singer says that while the female is more dominant than submissive in a pegging act, the role reversal isn’t just a turn-on for the man, but for many women, too. “A lot of women find both vulnerability and open-mindedness to be attractive traits in men — and it’s hard to think of a more vulnerable position, or one that requires more of an open mind from a man, than being on the receiving end of pegging,” she notes.
4. Why Does It Feel So Good?
Here’s a bit of an anatomy lesson for you: 1) you have a g-spot, just like your girlfriend does and 2) those highly-sensitive, feel-good nerve endings are located in your prostate and (best of all!) 3) your girlfriend can help stimulate those nerves for an epic 
orgasm.“Every person, regardless of gender, has thousands of nerve endings in their anal area. Every time we get aroused and have an orgasm our sphincter muscles are contracting and releasing with pleasure. I like to say that everyone’s butt is having a party during sex and arousal, but whether or not you choose to attend the party (i.e. do butt stuff) is up to you,” Riley says. “Lots of heterosexual men do enjoy anal play because of all those nerve endings, and lots of men have prostates, which are most effectively stimulated through anal penetration. The prostate is often referred to as ‘the male g-spot’ because people with prostates report that the sensation of a prostate orgasm is distinct from that of a penis-focused orgasm.”
If your partner has ever ventured below your testicles to gently stroke your anus, you might have noticed how quickly you rush to the finish. Why is this? Any type of stimulation in that area gets that prostate going, and thus will turn you on in a way that you can’t achieve with traditional oral sex or intercourse. “The secrets of male prostate and anal stimulation have long been the domain of sex workers. Historically, when sex workers needed a guy to finish up in a hurry, she would slip a finger up his ass, touch his prostate, and most guys popped their cork right there. The kink world has long known about pegging,” Nelson notes.
5. Talking To Your Partner About Pegging
It’s normal to feel uncomfortable starting a conversation about how you want your partner to do something to you that, chances are, she’s never done before. However, when you’re in a relationship with someone who fully accepts you, unconditionally, you may be surprised how willing and open she is to make sure you’re getting the most of your joint sex life. And you never know — it might encourage her to explore some of her fantasies too. Like with any sticky discussion, experts advise you tread with caution but remember to be completely, totally honest.As psychologist Dr. Rachel Needle explains, being brave enough together to venture into unknown sexual territory will not only bring you closer, but it increases your communication and your intimacy. “Make sure you are in a safe, comfortable place without the possibility of interruptions. Test the waters and get your partner’s permission to talk about it. Some people introduce new ideas and additions into their sexual relationship without first communicating about it. Depending on your partner, this may work, if done gently. However, communication is one key to a healthy relationship,” she says. “So, whichever route you decide to take, be sure that it involves verbal communication at some point, to ensure that your partner is on board with the idea and is not feeling threatened or confused by it.”
Another idea, according to Nelson, is to start slow and first discuss anal finger play before diving head first into pegging. “I think the best way to approach the whole thing is start just with prostate stimulation during oral sex. You can say, ‘You know, I was reading about this thing the other day, where a woman massages a guy’s prostate. They said that guys go nuts for it. Have you ever heard of it?’” he explains. “Chances are she has. Chances are she will try it. Chances are she will like it if you do. From there, it is a simple step from prostate massage to using prostate toys and then to pegging!”
6. Best Positions For Pegging
Done your research? Check. Talked to your girlfriend? Check. Tried having her use her finger first and you (really) like it? Check, check. Now that you’re ready to move on to full penetration and truly venture into the world of pegging, you’ll need to know what positions and angles will bring you the most pleasure while still being comfortable. And even if you’re proud of the size of your personal member, a lighter version for your first pegging experience is recommended. “Many guys prefer to start with a small, flexible rubber wand. With experience, guys may want to increase girth to increase sensation, but it’s really an individual choice,” Nelson explains. “Every guy is different. For some, the mind game of using a life-like dildo is part of the experience. For other guys, they just want a generic peg.”Here are the positions you should start with:
If you ever talk to your girlfriend about what it feels like to have sex and what she experiences, she’ll likely report how important it is to ease into intercourse, because a sudden movement can be painful. The same goes with pegging, so that’s why it’s key for you to be in control of how deep and intense you want to go. “Many guys report that it is easiest to start with doggie position, either standing or
kneeling, with her behind him. It is important for beginners to let him back onto the peg so he can regulate penetration,” Nelson says.When you’re starting with doggie, remember that you might have to coach your partner through the process. While you know all of the tips for penetrating doggy style, she has only ever been on the receiving end, not the giving. “Have her try different angles and types of thrusts, and give her feedback about how it feels and the desired pressure and intensity. Ladies have a hard time figuring out the angles at first, and depending on your strap-on harness, the angle will have to be fine-tuned. Standing or kneeling from behind or on your back with your legs up or bent are good places to start,” Gunn says. “Also, remind her to not forget about the rest of you! Have her touch your body, put her body down against yours, stroke your penis or perineum. Sometimes the combination of the touches is the key, not necessarily just one thing. Ultimately, every man enjoys prostate stimulation in their own way. So finding that right fit, the right toy, the right technique, can take some trial and error, but if you’re communicating, staying positive, and supporting the journey, it’s nothing but fun.”
girlfriend’s face while she penetrates you and it frees up both of your hands to explore one another’s bodies.“Probably the most favorite position of all is with the man face-up. It usually works best if the woman stands by the side of the bed with the man’s butt right at the edge. She can penetrate very slowly while he can relax and breathe deeply,” Nelson explains. “She has ultimate control over the speed and depth of the thrust and she can watch his face to gauge his pleasure. This is a great position because either partner can stroke his penis while being penetrated.”
You may love the Cowgirl positions because of the view you have of your partner’s beautiful body and how it feels for her to ride as
hard as she can on top. For similar reasons, you will also enjoy Cowboy — except instead of her being in control, you’re the one in for the rodeo. “A fun variation on face-to-face is to straddle your girlfriend with your knees on the bed. In this position, you have total control over the angle, depth, and speed so she can enjoy the show,” Singer explains. “Here’s a fun trick: slide all the way down (or at least, as far as you enjoy) and instead of moving up and down, you can swivel your hips from front to back, from side to side, or in circles. The dildo will stimulate your prostate with each move and you can try different speeds and directions to find the ones you like most.”7. Things To Remember
As you start along your pegging journey, experts recommend you keep a few go-to items in your sexual closet so you can have them handy for whenever the mood strikes. Having these at hand will ensure that whenever you’re both in for something a bit more kinky, you can go at it, without losing the luster or the drive.Lubrication
“You need to invest in high quality lube. Water based lube is a must if you are using a silicone dildo — which I also recommend. You want something soft, firm, and flexible. Silicone is also easy to clean up and sterilize by boiling. Don’t go cheap,” Nelson says.
A Strap-On That Works For You
It might take some time to find the right type, fabric, size and sensation for you. But that’s okay — Gunn reminds you that trying out different ones for the amount of pleasure and comfort they bring you is all part of the pegging game. “Find a good strap-on that is washable. Leather is pretty but hard to sanitize, rubber is waterproof but not as flexible. I would recommend the fabric to start; they are less expensive and can be thong, underwear, or two-strap style. Spare Parts makes some really amazing options,” she explains. “If your strap-on has adjustable straps, make sure it’s nice and snug so the dildo stays erect and in place. Many come with their own O-ring, the ring at the front that holds the dildo in place. Finding the right dildo type and size can be tough so start small and buy a silicone product because it’s easily sanitizable. Your local sex toy shop will help with getting you all the gear you need. Butt stuff with either gender is difficult and can result in pain and frustration. But as you try different options, it gets easier and more pleasurable.”
An Open Mind
It’s not going to be easy at first, and might even take a lot of practice — but simply opening your mind and having patience with both 
yourself and your partner as you try this new act will take you a long way. “It doesn’t always turn out great right away. That’s okay. Facilitating increased pleasure and sexual adventure with a partner means taking it easy, showing grace and acceptance, and growing at their speed too,” Gunn says. “Maybe today wasn’t the day to peg, but tomorrow will be. You can be sad, but avoid guilt, shame or anger towards a partner for their body or brain’s response to something new. The fact that you’re trying is huge! Keep up the sexy work!”
