Strapon Tutorial

Strapon Tutorial
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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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The idea that a cisgender woman can strap on a dildo and a harness that makes her feel like a cowboy and a penetrate another person, no big deal, basically seems like the epitome of cool to me. But obviously strap-on sex can be just as awkward as penis-in-vagina penetrative sex. You could be having a great old time until the dildo pops out or goes in the wrong hole or you have to switch positions because it's hitting a spot in her vagina that feels like someone's stabbing her with a dildo, which isn't ideal.
Jen Laws, a 30-year-old transgender man and Customer Service Rep for PerfectFitBrand, has some mixed feelings about strap-on sex. "It can be a reminder that my body has failed to live up to my personal ideal around sex," he says, but it's still one of his top three favorite sexual activities. Strap-ons can be used by straight women to penetrate their boyfriends (which is called "pegging") or by gay women or trans men to have penetrative sex their female partners, or by anyone to penetrate anyone! The penetrative options are endless.
I spoke with a bunch of women and transgender men who love strap-on sex to walk me through all the ins and outs of using a dildo. First things first: Purchase a dildo and a harness.
1. You don't have to choose a dildo that looks like an actual penis. Stephanie Berman, 34, CEO of POPDildo & The Semenette, says she knows some lesbians who love dildos that look like penises, but says plenty of other women like more sculptural dildos. And then there's a third group that thinks they all look the same in the dark, which is a legit point. The main thing you need to do is bring your partner dildo shopping so you can choose one together. Carly S., 28, general manager of Romantic Depot in NYC, says a good rule of thumb is "the wearer picks the color, the receiver picks the size." Carly also recommends finding a sex toy shop that can advise you on toys that are body safe (see also: won't give you a UTI or yeast infection because some will do that, and it is the worst. Usually silicone is a safe bet). Plus, a lot of stores will show you how to put the dildo and the harness together, kind of like someone at a regular toy store helping you put together a Barbie dream house, if that Barbie dream house was about to go into someone's vagina.
2. Yes, it matters if your strap-on equipment is well-made or if it's a piece of garbage you got a good deal on. Berman says she once wore a strap-on that was really uncomfortable and cheaply made, and it broke during sex, and I'm guessing no one was psyched to pick up the sad dildo up the ground that had random hair all over it and start again by trying to make a new harness out of a sheet. Now she recommends SpareParts harnesses. "It's worth spending the extra money," she says, "Never skimp when it comes to sex and what you put on and in your body!" Laws avoids the strapless ones (such as the Feeldoe toy line), which are basically double-ended dildos with one end angled to be inserted into the active partner. "It basically just uses their vaginal muscles and nothing else to keep the toy in place," he says.
3. You can totally have different strap-ons for different moods and purposes. Carly has three different harnesses for different activities. "I have an underwear-style one that I can wear under my clothes, a leather one if that's the mood I'm in, and a Joque from SpareParts HardWear harness that's great in the water."
4. It's really important to manage your expectations about how easy and hot strap-on sex will be. Victoria, host of sex podcast Livin' and Lovin' in NYC , 33, told me that the fantasy that you'll spontaneously screw and it will go seamlessly needs to be dismissed ASAP for everyone's sake. The reality is you'll have to take a break from fooling around to put the harness on, make sure it's fastened, and get out the lube, which is basically the opposite of spontaneous sex. In general, all the people I spoke with said having a sense of humor about all the potential pitfalls and awkward moments is definitely your best friend (alongside lube...).
5. Lube is your BFF. Every person I spoke with mentioned lube at least three times, so definitely do not skimp on the lube situation. Your dildo's material can sometimes dry out your vagina, so it needs a lot more to help it slip in and out with ease.
6. It will absolutely be awkward when you first put on the strap-on. Berman said when she first strapped on a strap-on, it just felt foreign to wear a penis, especially if you feel weird about your body, or your gender or sexual identity. In her first lesbian relationship, she was a bottom because she'd previously been with men and that's what she was used to, but once she felt more confident with her sexual identity, she was happy to be both a top and a bottom. That said...
7. You don't have to just stick with one role of the bottom or the top. My friend Jessi, 23, said she loves being both the giver and the receiver of strap-on sex and Victoria echoed similar sentiments. "Many straight folks might assume that only one person in each sexual partnership is going to do the drilling, and if one partner is masculine, the assumption is that it's them," Victoria says. "In my case, I'm quite androgynous and tend to date feminine-of-center women, and I love to get drilled. I can't even claim to be that good at doing the drilling myself." Victoria says when she's had partners who were inexperienced with strap-ons and she still wanted them to take the reins in bed, but she told them she didn't expect them to be pros right off the bat. Bringing that kind of openness and levity to, "Hey, will you put on a harness and nail me with it even though you've never done that before and might be terrified of how weird it will be because it will definitely be a little weird for a bit?" can really make the person you're asking feel better about it.
8. It's way more intimate than having someone use a vibrator on you. Strap-on sex involves really getting to know someone, because you have to ask what the other person likes in terms of size, shape, and color (which brings us back to the "some women don't want the dildo to look anything like a penis at all" point).
9. Strap-on sex is not a "strap on this dildo and get to it" activity. It requires a lot of set-up before and clean-up after. Laws says he hates seeing strap-on sex in porn or on TV (I can personally only think of one scene in The L Word and of course the Broad City scene with pegging because it's really not seen very often on TV) because it takes a lot more planning and set-up and clean-up than they ever show. "Even after a mind-blowing orgasm, the base of a dong is digging into my pelvis, and that's uncomfortable, and body fluids or lube are just kind of messy to leave hanging around, so you have to clean it up," Laws says, "Plus, harnesses always take work to get the right fit, and things slip and move during sex."
10. It's not a penis, but use a condom anyway. Victoria says she recommends using a condom on the dildo for easier clean-up because that way you won't have to immediately wash all the dried bodily fluids off the dildo and leave it to dry. Plus, a lot of condoms are lubricated, which can help with any dryness caused by the dildo material.
11. You should explore your strap-on in your day-to-day activities because why not. Laws seriously recommends walking around with the strap-on and stroking it like you're jerking off, so you can get comfortable with it and "have fun with it" like it's part of your own body.
12. Giving a strap-on blow job can be totally hot. Laws told me the best advice he can give is to not overthink it, whether you're blowing someone or being blown. If you're the one receiving, once you feel connected to your equipment, you'll see the dildo as an extension of yourself and there'll be more of a mental feeling of stimulation that can translate into the physical. If you're giving, just be enthusiastic no matter what you're doing. Gripping the base of the dildo and grinding that into your partner's pelvis can help with clitoral and vulva stimulation. Just pay attention to the way they're responding, so you know how much or little to keep grinding.
13. Here are all the things that might go wrong with your dildo and O-ring and harness. Laws says that once you have everything fitting right with your harness, you still might have issues. Most often, if you're using multiple dildos in one session or if you're new to strap-ons, you might find that not all your dildos or O-rings are the same size, and they need to have a snug fit or the dildo will wiggle out of the O-ring. Also, your harness snaps might not be up to the challenge of your vigorous sex-having and could come undone, or your straps could eventually get worn out if they're elastic. Seams and connection points can also get weakened over time. Because harnesses aren't cheap, you probably don't have several in your house just chilling, but even if you did, there's still the awkward "now I have to take this off and put another one on and go back to sex like I didn't just leave for 20 minutes" conversation. Laws says he usually doesn't feel like going right back into strap-on sex if any of those mishaps do happen and just moves on to something else. So make sure everything fits and is tightly in place before your boo comes over!
14. Don't thrust as much as you might be tempted to thrust. Carly says a lot of women use their hips too much when they thrust, and recommends trying to keep your hips straight and thrusting lightly, instead of moving side-to-side.
15. No, you obviously won't have sensation like it's attached to your body, but that doesn't really matter. Laws says that not having the sensation he'd have if the dildo was an actual body part is his least favorite thing about strap-on sex, but he still loves the power-play aspects, whether he's giving or receiving. Justyn A. Hintze, 27, a sexologist and sexuality educator at the Woodhull Freedom Foundation, says they've always been frustrated that they couldn't feel their partner's body reacting physiologically to the pleasure like they could when they used their hands, but just watching their partner enjoying it is hot enough for a lot of people.
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Here's why pegging has a special name, how to do it safely, and all the best toy recommendations to try it out.
Sophie Saint Thomas is a New York-based writer originally from the Caribbean. She is Allure ’s resident astrologer and the author of Finding Your Higher Self: Your Guide to Cannabis for Self-Care (Adams Media), a guide to self-care and marijuana, and [*Sex Witch: Magickal Spells for Love, Lust, and... Read more
It's Kink Month at Allure, and we're talking all about fetishes and kinks. Read more on our landing page here .
Can pegging make your partner a better lover? Some people, including experts in the sex and relationships field, certainly think so.
"When I have sex with cisgender men, the ones who receive anal penetration are much better lovers than those who haven’t," says kink-friendly sex therapist Liz Powell . Well, if that's not enough motivation to explore this misunderstood and even controversial activity, I don't know what is.
Of course, the decision to try pegging with a strap on is completely up to the individuals involved, and many folks are wonderful sexual partners regardless of whether they're interested in this form of sexual exploration. But what is pegging, why is it so hot for some of us, and what supplies and knowledge are needed to try it safely? Allure spoke with Powell and a professional dominatrix to learn all you need to know.
Traditionally, pegging refers to a cisgender, heterosexual male receiving anal penetration from his cishet female partner with a strap-on dildo — and, actually, it's a word surrounded by a bit of controversy.
As our understanding of gender and orientation expands, some folks ask, why not just call this anal sex, strap-on sex, or just sex? Why do cishet guys need their own word for anal penetration when the rest of us have been enjoying it as is? Powell understands this line of thinking, but they also say that giving an activity its own word, be it fisting, squirting, or pegging , can help us talk and think about what we’re doing.
"Having a term for pegging can, in some ways, be helpful," Powell explains. "A lot of cis straight men are interested in pegging because when they find out that there’s a term and that it’s common they feel a lot more OK about wanting that." Talking about pegging specifically can help normalize it and debunk outdated thinking about cishet men and prostate pleasure.
"Could we just call it sex? Sure, but there are lots of things we could just call sex," says Powell. "Having more terms doesn’t necessarily make it worse; I think that pegging is more stigmatized because it is about a cis straight dude. A lot of people are still really uncomfortable with men receiving penetration."
Everyone's butthole is lined with erogenous nerve endings, which is why people of all orientations, genders, and bodies can enjoy anal sex. And having a prostate is a fun bonus.
“A lot of prostate owners don’t get to stimulate their prostate, and that’s a whole other orgasm available to you. You’re opening yourself up to other avenues of pleasure," says New York City dominatrix Domina Katarina. The prostate, or P-spot, is roughly three to four inches inside the rectum, about an inch in diameter. The person with a prostate can usually let you know when you've found it as they'll start to feel sensations reminiscent of an orgasm .
Outside of the physical pleasure of prostate and anal stimulation, both partners, commonly referred to as the bottom (receptive partner) and the top (penetrating partner), may enjoy the "taboo" of a role reversal, if receiving penetration is new for the partner with a prostate or penetrating someone is new for the top. "The power dynamics are amazing," Domina Katarina says. "Especially as a woman who is typically seen as submissive, it really does put you in a different position. You get a rush, like, yeah, I have this control."
While some simply want to be penetrated for the prostate stimulation, for other straight couples, they may get off on the role reversal. Submissive cishet men may enjoy the erotic power exchange that occurs when their partners become the ones with the dicks. "I get why dick owners walk around like they’re the shit," Domina Katarina says of the place of power she entered through her experience pegging.
Pegging can also (but doesn't have to) be a part of BDSM dynamics . All BDSM involves consensual power exchange, and for some cishet men — who, in our patriarchal society, still tend to harbor the most power — submitting to a woman or other person of a marginalized gender gets them off.
Pegging also requires immense trust; being penetrated anally with a strap-on dildo by a pro-domme or dominant partner allows cishet men to not only receive anal pleasure but become vulnerable and submissive, which is a common sexual desire.
Safe pegging requires taking the same time and care you'd use during any anal penetration. Before you work your way up to a dildo and harness, begin by inserting a finger, and then two, with plenty of lube . Because pegging usually means using a strap-on dildo (which is commonly made with silicone), you want a water-based lube. Silicone lubes can cause silicone toys to deteriorate. Sliquid H20 is an excellent choice , because it's safe to use with silicone toys and is flavorless and scentless.
After you've warmed up with fingers, feel free to add a butt plug to help prepare the area. The Snug Plug from B-Vibe , a weighted, smooth butt plug available in a variety of sizes and shapes, is excellent for anal sex warm up. It has a nice flared base that keeps it in place. For pegging, you can have the partner with a prostate wear a butt plug for a bit while you fool around or tease them.
When you're ready to peg, you will need a strap-on dildo and harness. If you can, buy your first harness in real life rather than online so you can try it on. Some harnesses are strappy leather and sexy as hell, such as the Minx Harness from Aslan Leather . Others are more practical, such as the TomBoii Boxer Briefs , which are ultra comfy and can hold a dildo in place like no one's business. Go with whatever works for you and your partner's desires.
So, what about the actual dildo? "For pegging, the really good dildos are the ones that are narrow in diameter that are fairly long," Powell tells Allure . It can be helpful to go shopping with your partner so you know what you both want. Some people prefer realistic dildos and others want something bright and colorful. No matter what, start small.
If you're interested in a vibrating anal dildo, try the Riley Vibrating Dildo . If you're curious about a curved dildo made like anal beads, try the Your Highness Vibrating Dildo . And if you were wondering, yes, there is a Broad City Strap-On Set .
Other than making sure all partners are aware of how to physically prepare, remember that there is a major emotional component to the sex act, especially if it's someone's first time. Make sure to communicate beforehand about both of your desires, expectations, and fears. "When it comes to pegging, even though that dildo is not part of your anatomy, you are still inserting a part of yourself in someone else, and that’s extremely intimate. There’s a great responsibility, because you are entering them," Domina Katarina says.
Start slow and use plenty of lube, checking in with your partner throughout the experience. "Don’t think you’re going to be like thrusting and whipping a lasso around your head," she says. "It has to go nice and slow and easy or else you could do physical damage, and you could do emotional damage. It’s a really awesome way to connect differently with your partner."
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