I still remember the heady mix of excitement and terror that went through my system the first time a partner asked me to peg them. Even the act of asking me seemed like an exercise in intimacy as he confessed that it was something he never thought he'd ever get to try in his lifetime. He was asking me (yes, me!) over every other partner he'd ever had. He trusted me enough not to leave him, humiliate him, or embarrass him over it. Even the act of asking seemed like a new level of trust, and that was before I said I'd give it a try!
Pegging: the sexy story of how one women went from "hate" to "heart."
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Before we even made the time to replenish the groceries in the kitchen, we found the time to hit up a local sex toy store. Sure, we'd been in there before, but now we had a purpose! I was in there with the intent to find everything I needed to make everything about this man's wish come true. If that wasn't enough pressure for my shopping, I don't know what is. While I knew the basics of sex toys, pegging activities still eluded me. I really could have used a knowledgeable salesperson to help me out. Unfortunately, the guy glaring at me from behind the dingy counter was not that person.
Instead, I relied on the barely-there information provided on the packaging. As it turns out, that was just about as useful as the guy behind the counter. Ten years ago, sex toy packaging hadn't come nearly as far as it is today. "Factual information" on the packaging took a backseat to the large, computer-generated images of lesbians adorning every strap-on kit in the store.
As a plus-sized woman, this was where the experience started to go downhill. From my experiences in clothing stores, I knew "one size fits most" rarely included me. So as I shopped for strap-on harnesses with no discernible information about whether they'd fit my body besides the fact that it would fit "most," I was stuck making a wild guess.
Read: Pegging Tips for Plus Sized People
Finally, I settled on a harness and two-dildo kit that promised "Curvy Pleasure." It was plastered with photos of two lingerie-clad women wearing the set while making out. And, of course, a bottle of lubricant came home with me, too. Even back then, I knew we needed lube.
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I spent the entire week filled with that same mixture of excitement and terror. I was excited to try a new sex act and boldly go where I hadn't gone before! At the same time, I had no idea what I was doing. How was supposed to make this pleasurable for him when I'd never done this before? How would I get the dildo into him? How much lube was I supposed to use? There were a plethora of unanswered questions that added to my anxiety. While I looked forward to the experience, I was just as terrified by it. Our first roadblock came in the strap on harness. Having never put one on before, I had no idea what to do. Coupled with the fact that I had no idea if it would fit, this was something I really wanted to do in private. In my mind, I'd emerge from the bedroom as a sexy vixen, ready to show him all sorts of new sensations - and perfectly showing off my newfound appendage.
Our sex was even hotter leading up to our newfound kink. We both knew it was coming. It was sorta like we'd found a new layer of sexuality and enjoyment to explore with each other. Knowing he felt comfortable to trust me with his secrets added an entire dimension of vulnerability to our sex. I'm sure he was thankful that he felt he could come to me with any fantasy he had and I wouldn't judge him for it. I remember the nights leading up to that weekend fondly ...just not the pegging that followed.
The night of the big event, we did no preparation. We didn't have any further discussions. We didn't try out anything ahead of time. Instead, after an average dinner and a few drinks, he came onto me - telling me how hot it would be if I'd put on our new toys and give this pegging thing a go. He was ready and wanted to play, and to be honest, I was ready to give it a try too.
In his mind, his fantasy girl verbally teased him while she put the harness and dildo on, so when he started begging, I gave in. Making this experience as hot for him as possible was my priority. He'd probably watched more porn of it than me. Who was I to argue about what method was best? He watched as I slowly adjusted the buckles on the harness, swearing as they got stuck, until they were all at the largest settings. He continued to watch as I put it on, barely squeezing myself into it, before swearing again as I stepped into the wrong strap and had to remove the entire thing.
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He still watched, now getting more visibly annoyed, as I spent the next five minutes trying to fit the dildo into the harness while wearing it ... before stripping it off, putting the dildo back in, and then stepping into it again. Needless to say, all of his desired “dirty talk” was going towards this frustrating piece of fabric. Quickly stripping off his clothes in excitement, he was soon naked and face down on the bed. If he noticed my lack of enthusiasm, he chose to ignore it. I decided to ignore it, too. I climbed onto the bed behind him with the bottle of lube and quickly lubed up the length of my slim dildo. At least I managed that part OK. Within minutes, I was kneeling behind him and attempting to slide it in only to be met with the newest challenge: my dildo was still at least 6" away from where it needed to be to actually penetrate him. With our height difference and the two of us kneeling on the bed, I'd only be able to slide my dildo between the middle of his thighs at best.
All-in-all, it was a good 20 minutes of fumbling and attempting. I was at the point of tears as I finally revealed the finished product. I didn't feel hot. I didn't feel sexy. I felt incompetent. I had no idea what I was doing. I definitely didn't feel aroused or turned on. I felt lumpy in the harness. Despite just putting it on, it already felt itchy and kinda painful. Nothing felt good, but dammit, I was going to make sure his fantasy came true!
The fact that I remember the feelings vividly as I cringe over it, more than 10 years later, shows exactly how intense that moment was for me.
I blinked the tears away as I presented myself to him, dildo dangling between my legs. He'd taken to playing on his phone during the latter half of my dressing. The phone was quickly returned to the nightstand when he figured out that I was done. With the sexiest voice I could manage with my mental state, I asked how he wanted it - and tried to fit in as much dirty talk as I could about how hot and sexy it was going to be to fuck him.
I had zero idea how to fix this sex position problem. I also had zero idea, in my youth, about how to boss him around in a sexy manner that would still make penetration possible.
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So I attempted to fix it myself.
I kneeled as tall as possible. Nope.
I tried to get up onto one leg and one knee. I couldn't figure out how to get it in with such an intense angle and such a small dildo. Nope. How about squatting? Nope, that didn't work either ... and I almost fell off the bed with that attempt.
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He was going to have to move to even make this possible.
It quickly turned into a small argument. He was annoyed I asked him to move. I snapped back because even the adjustment I'd asked him to make didn't seem to really make penetration possible. I asked him to make another adjustment or movement. He complained that it was impossible for his body or too uncomfortable. We tried something else.
If we were smart, we probably would have called it all off. But we weren't. We were two dedicated, young people attempting a new thing. So hey - we were going to do the thing!
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About thirty minutes later, we had a semi-workable pegging position with him crouching on the floor next to the bed while I uncomfortably held my body in this very precarious position. The angle was finally right! We were finally going to get to all of the rewarding stuff!
With the tip of the dildo ready to go, I started to push in. I'd read the articles that said to go slow. So that's exactly what I did. As slowly as I could possibly go without losing my balance in my precarious, kneeling position, I moved my hands out of the way and slowly slid things in. With zero feedback to go on, I just slid in until I thought I was there, and then I started to thrust.
A few seconds later, my partner finally chirped up. I wasn't even in the hole.
OK, attempt number two. Attempt number two ended up being about as successful as attempt number one. When you're unable to feel or see the thing you're trying to insert, the ability to make it into the "right" spot becomes a whole new challenge. This time, my failure was met with a snide comment and a sigh.
Attempts three and four went about as successfully. I was so frustrated and annoyed about the entire experience at this point. We sucked at this, had no idea how to suck less, and I just felt terrible.
Finally, attempt number five finally worked. Unfortunately, the lesson of "slow penetration" had left me somewhere between attempts three and four, and five slid in entirely to the hilt without much patience. When he finally gave me the go-ahead to start thrusting, I did just that. I was surprised by how monotonous it seemed. The toy and harness gave me no feedback or stimulation. I just rocked back and forth while he quietly laid beneath me.
It was awkward, to say the least, and I spent most of the experience blinking back tears and willing my shaking muscles to continue to hold me in this awkward position. I was just silently waiting, breathing heavily, for him to give me the go-ahead to stop or to orgasm or something.
Finally, he did just that, and said, "That's enough." I awkwardly pulled out with no fanfare to a mess of a toy. From my reading, I knew to expect a bit of it, and I tried to take it with grace as I attempted to take off the harness without spreading any of the concerning material. He continued to just lay on the floor as I cleaned up the toy.
Coming together afterward, we had a bit of an awkward talk. He expressed how wholly disappointing the entire experience was for him. I tried not to take it too personally. I stayed quiet, just letting him express himself, as he expressed how unpleasurable and disappointing I made the entire experience.
At a certain point, it became impossible not to "take it personally." I just tried to hide how upset the entire experience made me. I felt like I destroyed his fantasy - with no way to really "re-do" it. And I wanted as far away as possible from ever trying to peg someone again.
After all of that, I swore it off. It was definitely a kink I was never, ever going to try again. Not only was it a turn-off, but it was an activity fraught with misunderstandings, lots of anger, and a whole bunch of frustration. And absolutely no pleasure for me. Fuck that.
It's hard to articulate exactly how damaging this experience was to me. Pegging went from the “Hell yeah, let's try it!” straight onto the hard limit list of my kinky repertoire. I tossed the harness and toy out shortly thereafter. As you might have guessed from this article's title, things have changed. So what changed? How did I go from hating pegging so much to swear it off entirely to teaching rooms full of women how to peg for the first time? Or giving a nervous woman tips and tricks to make it better for her? Or even to all of the how-to articles I've written here on Kinkly? He said he'd go online and help me research harnesses that would work for me...and he'd be happy to pay for them and other body safe sex toys. He said he'd love to help me try it on during a free night before we do the actual activity and get used to the weirdness of it. He said we could try lining up our hips, fully-clothed, before the night happened to find some good positions that worked for us. He'd even help me insert the dildo during the pegging itself. Read: 5 Things to Know About Strap on Dildos and Harnesses He said we'd take it slow if I ever wanted to try it again. And he'd be there to make sure the experience went better. True to his word, we spent a couple of weeks just "prepping" for the act of pegging. He went out of his way to make me comfortable with this newfound sex act. As my comfort grew, so did my confidence for providing the "experience" that he wanted out of it. When I brought up the fact that I wasn't receiving much physical pleasure from it, he instantly had ideas. He prioritized making sure we tried them during our pegging sessions, too. (Some of those solutions have included the BumpHer, the Wildflower Enby, Strap-On-Me Vibrating Bendable Strapless Strap-On, and clitoral-focused dildo bases like the Wet For Her Fusion). Some sex furniture helped with my sex positioning issues too. Now that I felt confident sliding on my dildo harness (seriously, the Spareparts Joque was a game-changer for me!), it wasn't some far, unreachably terrifying thing - it was just a different way to have sex with him. And it was amazing. We've since taken that basic pegging experience even further by happily involving it with the rest of our kinky sex life. Pegging with kinky restraints is amazing - and getting better positions with Liberator sex furniture and other BDSM sex furniture has helped me explore different ways to get the perfect fit between our bodies. I never, ever want someone to have a similar first pegging experience like I did. Call this my "origin story," if you will.
I have to be straight with you: it was a new partner and a new attitude. That's what changed.
When I started dating this new partner, during one of our open discussions about kink, I made it clear that pegging did nothing for me, and I wasn't at all interested in doing it. My declaration was met with his acceptance, but huge disappointment. Pegging was one of his favorite kinks.
I didn't budge. Despite our budding relationship, he wasn't going to change that. Or so I thought.
Despite my hard stance, though, the months passed, and he did change it. Slowly. Instead of being pushy and demanding the main event, he effectively (and as a "Dominant", I hate to admit it) trained me to the idea. He started with the gentle suggestion that he'd wear a butt plug out for me during dinner. Well, that sounded pretty fun. From there, his gentle suggestion included offering to ride a dildo while I watched. More "Hell yeah" on my end.
Finally, he asked if I'd be comfortable having that dildo strapped onto my body as he rode it as his birthday present. He explained he had no expectations for me. If I hated it, he'd be happy stopping at any point. With such a respectful presentation of the idea, it was time to "come clean" about my past. And that's exactly what I did. I explained how terribly it went, how stupid I felt, and how wholly unsatisfying it felt. Reliving the experience all over again brought back the same tears and the same feelings of incompetence, but I made it through my explanation.
Instead of continuing to push for pegging, he instead said he'd never ask for it again. He understood my experience. If I did want to give it a try again, though, he lined out all of the ways that he'd help make it better by being an active participant in the pegging experience.
Put like that, my barrier around pegging slowly started to fall. It took a couple of months, but I finally came around to the idea of giving it another try.
Our first pegging, while a bit awkward, was actually fun. It wasn't as nerve-wracking as my first time around. While it wasn't physically arousing for me, it was mentally arousing to see him enjoying himself so much. We tried it a couple more times. Each time, I got more and more comfortable with it. Soon, he wasn't having to help me as much, and I was taking charge in our encounters ... and enjoying it.
With this new, actively-involved pegging partner, I found my confidence in a strap-on harness. I started being able to orgasm from the sensations of pegging as well. He was enjoying himself, I was enjoying myself, and it was something that I looked forward to doing - usually about once a week or so.
Now we're polyamorous, and I've "loaned" him out to kinky friends to help them learn how to peg. Each time, the women come away from the experience absolutely awed - and full of so much more confidence than when they started. Along with that, I started teaching classes on pegging. Not just the basic beginner's class on pegging, but also classes on how to receive pleasure as the harness-wearer and ways that plus-sized pegging participants can make pegging work with their bodies as well.
If there's any takeaway from my experience, it's that pegging needs to be an active experience for the bottom. I know part of the fun and taboo as the pegging-receiver is being the "receptive" partner who just receives all of the top's activities. However, "receptive" doesn't have to mean you don't put forth any effort. Most vagina-bodied individuals aren't used to penetrating things - and most certainly aren't used to wearing strap-on harnesses and dildos. If you want your pegging top to come away satisfied, you need to help provide part of that experience. In return, they'll gain the confidence to peg even better in the future.
Luckily for you, we have tons of articles here on Kinkly to make your strap-on sex a sexy experience from the get-go. Don't make the same mistakes I did.
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Mistress Kay
Mistress Kay has a fondness for all things sexual. With a house that's quickly running out of room for all of her reading and vibrating pleasures, she spends her free time reading, writing, and learning about the sexual universe with her partners. She can be reached at Kinky World.
