How One Woman Went from Hating Pegging to Making It a Weekly Part of Her Sex Life

Pegging is a captivating story about a woman's journey from "hate" to "heart."

I still vividly remember the enormous feeling of both excitement and dread that went through my body the first time a partner asked me to peg them. Even asking me seemed like an intimate exercise, as he acknowledged that he never thought he would get to taste it in his lifetime. Instead of asking everyone he had ever dated, he was asking me. He trusted me enough to prevent him from leaving him, ridiculing him, or embarrassing him as a result. The asking indicated greater trust before I said I'd try it!

Sex Toy Store Pressure + Little Information = Overwhelmed

Before we even considered replenishing the kitchen, we managed to find time to visit a local sex toy store. Naturally, we had already been inside, but we had a purpose this time! Finding everything I would need to realize this man's dream was my goal when I was there. If that wasn't enough pressure, I don't know what to do with my shopping. I knew the basics of sex gadgets, but I still didn't understand pegging activities. A seasoned salesperson's help would have been highly beneficial to me. Regretfully, I was not being sneered at by the man behind the dirty counter.

Instead, I relied on the scant information found on the package. The man at the counter proved to be more helpful than that. Over the past ten years, sex toy packaging has dramatically improved. The "factual information" on the container was overwhelmed by the enormous, computer-generated images of lesbians that decorated every strap-on kit in the store.

As a plus-sized woman, this was when things started going wrong. From my experiences in clothing stores, I knew that "one size fits most" was rarely true for me. Other than the notion that strap-on harnesses would fit "most," there was no complex data on whether or not they would fit my body, so I had to make educated estimates while shopping.

In the end, I chose a harness and two-dildo combination that promised "Curvy Pleasure." It was filled with pictures of two women in suits, making out in their undergarments. I, of course, also took a bottle of lubricant home. Even then, I knew we needed lube.

Strap-On Play: Boldly Going Where I'd Never Gone Before ...Literally

I felt the same mixture of excitement and terror for the entire week. I was eager to try a new sex act and boldly go somewhere I had never been before! Furthermore, I had no idea what I was doing. How was I supposed to make it fun for him since I had never done this before? I wanted to get him to take the dildo, but how? How much lubrication was advised to be used? There were a lot of unanswered questions, which made me more nervous. I was both excited and terrified by the event.

Our sex was much more intense before we found our kink. We both expected it. We appeared to have found a new aspect of pleasure and sensuality to explore together. The fact that he was comfortable enough to share his secrets with me made our sex even more vulnerable. He must have appreciated that I wouldn't judge him for having any desires and that he could confide in me about them. Though I don't remember any subsequent pegging, I remember the pleasant evenings leading up to that weekend.

We didn't prepare at all on the night of the big event. We stopped discussing it after that. Nothing was tested in advance. Instead, after a lousy dinner and a few beers, he came to me and told me how hot it would be if I did this pegging thing while wearing our new gadgets. He was excited to play, and I admit that I was excited to try it.

A Not-So-Sexy Struggle with the Harness Kicked Off Our Adventure

Our initial challenge was the harness's strap. I had never worn one before, so I wasn't sure what to do. I wasn't sure if it would work, but I wanted to do this secretly. I would see myself exiting the bedroom as a sexy vixen, ready to show him all sorts of new pleasures and displaying my freshly acquired appendage in a faultless manner.

I gave in when he started begging because, in his mind, his ideal woman verbally abused him while she put on the strap and dildo. I wanted our encounter to be as sexy as I could make it for him. He probably hadn't seen nearly as much of it as I did. Who was I to argue over the best course of action? He watched as I meticulously adjusted the harness's buckles, yelling at them when they became stuck until they were all set to their highest possible settings. When I stepped into the wrong strap and had to remove it entirely, he cursed again as he watched me put it on, barely fitting myself in.

Over the next five minutes, he watched, getting more and more agitated, as I tried to put the dildo into the harness while wearing it, then removed it, put the dildo back in, and stepped into it again. Needless to say, all of his desired "dirty talk" was directed at this obnoxious piece of fabric.

All in all, the twenty minutes of trying and stumbling were quite good. When I finally displayed the finished product, I almost cried. I didn't experience any heat. I felt nothing sensual. I felt unworthy. I had no idea what I was doing. I didn't feel excited or turned on. I felt lumpy in the harness. The mere act of wearing it was unpleasant and aggravating. Dammit, I was determined to satisfy his hunger, even though nothing felt terrific.

That experience was so strong for me that, over a decade later, I can still clearly recall the feelings as I shudder over it.

As I introduced myself to him, dildo hanging between my legs, I blinked away the tears. He had started using his phone to play music during the second half of my dressing. When he realized I was finished, he swiftly returned the phone to the nightstand. I asked him how he wanted it in the sexiest voice I could manage, given my current state of mind, and I made an effort to include as many obscene words as possible about how sexy and amazing it would be to fuck him.

He Was Naked ... and We Had Another Problem

He was so excited that he quickly undressed and lay face down on the bed, nude. He opted to dismiss my lack of enthusiasm if he noticed it at all. I also chose to disregard it. With the bottle of lube in hand, I climbed onto the bed behind him and lubricated my small dildo swiftly. I did okay at that portion, at least.

I was crouching behind him and trying to slide it in within minutes, but the latest obstacle was that my dildo was still at least 6" from where it should have been to pierce him. I could barely, at most, slide my dildo between the middle of his thighs because of our height difference and the fact that we were kneeling on the bed.

I didn't know how to resolve this issue with sex position. Additionally, when I was younger, I had no idea how to boss him around in a sexy way that would still allow for penetration.

I, therefore, tried to fix it myself.

I knelt as high as I could. Not at all.

I attempted to stand on one knee and one leg. I was unable to figure out how to get it in with a small dildo and such a strong angle. Not at all. Consider squatting. That didn't work either, and I nearly passed out during that effort. He was going to have to move even to make this possible.

It soon descended into a minor dispute. When I urged him to move, he became irritated. Even the change I'd requested him to make didn't seem to allow penetration, so I retaliated. I asked that he move or adjust in another way. He grumbled that it was too uncomfortable or impossible for his body. We made another attempt.

We probably cancelled everything if we were clever. However, we weren't. We were two young, committed individuals trying something new. Hey, we were going to do it!

All the Attempts, None of the Fun

About half an hour later, we reached a semi-workable pegging posture, with me holding my body in this hazardous position while he squatted beside the bed. At last, the angle was correct! We were going to reach all of the rewarding stuff at last!

I began to push in, the tip of the dildo ready to go. After reading the papers, I decided to take my time. I, therefore, did just that. I moved my hands out of the way and slid everything in as slowly as possible without losing my balance in my hazardous kneeling position. Since I had no input, I slipped in until I believed I was there, at which point I began thrusting.

Eventually, it took a few seconds for my partner to start talking. I wasn't in the hole at all.

Alright, try number two. Ultimately, the second try was just as successful as the first. Making it into the "right" place becomes a whole new issue when you can't see or feel what you're trying to put. This time, my failure elicited a sigh and a mocking remark.

The results of attempts three and four were similar. At this time, I was irritated and frustrated with the whole situation. I felt awful since we sucked at this and didn't know how to stink less.

At last, the fifth try succeeded. Sadly, I was left somewhere between tries three and four by the "slow penetration" lesson, and attempt five glided in entirely to the hilt without much patience. I did precisely that when he finally gave me the all-clear to thrust. It seemed so repetitive that I was taken aback. I received no sensation or reaction from the toy or harness. I swayed back and forth as he lay beneath me in silence.

I spent most of the encounter blinking back tears, and my trembling muscles would keep me in this awkward position because, to put it mildly, it was embarrassing. I was waiting for him to give me the all-clear to stop, climax, or something while breathing deeply and in silence.

At last, he did so and declared, "That's enough." Without any ceremony, I brought out a clumsy toy. As I tried to remove the harness without splattering any troubling substance, I wanted to accept it gracefully, knowing from my research that I should expect some of it. As I cleaned up the toy, he kept lying on the floor.

After that, we got together and had a somewhat awkward conversation. He talked about how downright disappointing the whole thing was for him. I made an effort not to get too worked up over it. I remained silent and let him talk about how unpleasant and unsatisfactory the whole experience was because of me.

There came a time when it was impossible to avoid "taking it personally." I tried not to show how angry I was by the whole thing. I felt I had ruined his fantasy since there was no way to truly "re-do" anything. And I wanted to avoid attempting to peg someone again as much as possible.

I swore it off after all of that. It was undoubtedly a kink that I would never, ever attempt again. In addition to being off-putting, it was an activity that was full of miscommunications, a great deal of rage, and a great deal of frustration. And no joy at all for me. Screw that.

I can't say how hurtful this event was to me. Pegging moved straight from my "Hell yeah, let's try it!" list to my kinky repertoire's hard limit list. Soon after, I threw out the toy and harness.

What Changed My Mind About Pegging

As the title of this essay may have hinted, things have changed. What then changed? How did I go from detesting pegging so much that I swore it off entirely to instructing ladies in pegging for the first time in classrooms full of women? or offering advice on how to help an anxious woman? Or to every single one of my Kinkly how-to articles?

It was a new mindset and a new companion. That's what was different.

During one of our candid conversations about kink when I first started dating this new partner, I made it plain that pegging didn't work for me and that I had no interest in performing it. He accepted my announcement, but I was pretty disappointed. One of his favorite quirks was pegging.

I didn't move. He wouldn't alter that, even though our relationship was starting. Or so I believed.

However, the months went by, and he did alter it despite my firm position. Slowly. He successfully (and as a "Dominant," I hate to say it) conditioned me to the notion rather than being combative and demanding the primary event. He began by politely offering to wear a butt plug out for me while we were eating supper. That sounds like a lot of fun. He then offered to ride a dildo while I watched, which was a kind suggestion. I'll say "Hell yeah" more.

Finally, as a birthday present, he rode the dildo and asked if I would feel okay having it strapped onto my body. He clarified that he didn't have any expectations of me. He would be content to quit if I didn't like it. It was time to "come clean" about my background when the concept was presented in such a polite manner. And I did precisely that. I described how awful it was, how foolish I felt, and how downright disappointing it was. Though I managed to finish my answer, reliving the event brought back the same emotions and feelings of inadequacy.

Rather than insisting on pegging, he declared he would never request it again. He understood my experience. However, he outlined all the ways he would actively participate in the pegging experience to assist in improving it if I did want to attempt it again.

He promised to look for harnesses that would suit me online and to gladly cover the cost of them as well as other body-safe sex devices. Before we perform the actual exercise and get used to its strangeness, he said he would love to help me try it on on a free night. He suggested that before nightfall, we attempt aligning our hips while fully clothed to discover some comfortable positions. Even during the actual pegging, he would assist me in inserting the dildo.

He added that if I ever wanted to do it again, we'd go slowly. He would also be present to ensure a more positive encounter.

In other words, my barrier around pegging gradually began to come down. It took me several months to finally decide to give it another go.

As promised, we merely "prepared" for the pegging process for a few weeks. He made a special effort to make me feel at ease with this new sexual behavior. My confidence in giving him the "experience" he desired increased along with my comfort level.

Even though it was a little odd, our first pegging was enjoyable. Compared to my first experience, it wasn't as nerve-racking. Seeing him having so much fun was mentally stimulating, even though it wasn't physically stimulating. We gave it a few more tries. I became increasingly at ease with it each time. Before long, he was less needed to assist me, and I was taking the initiative in our interactions... and loving it.

He came up with suggestions immediately after I pointed out that I wasn't getting much physical enjoyment from it. Making sure we tried them throughout our pegging sessions was a top priority for him. The Bumper, Wildflower Enby, Strap-On-Me Vibrating Bendable Strapless Strap-On, and clitoral-focused dildo bases like the Wet For Her Fusion are a few examples of these solutions. My problems with sex positioning were also resolved by certain sex furniture.

I discovered my confidence in a strap-on harness with this fresh, engaged pegging partner. I also began to experience orgasms from the feelings of pegging. I looked forward to doing it, usually once a week or so, and he was having fun simultaneously.

It was not this distant, unreachable, terrible thing; instead, it was just a different way to have sex with him now that I felt comfortable sliding on my dildo harness (the Spareparts Joque was a game-changer for me!). And it was incredible.

Since then, we've joyfully integrated that simple pegging experience with the rest of our kinky sex life, taking it even further. It's excellent to peg with kinky restraints, and learning better positions with Liberator and other BDSM sex furniture has allowed me to experiment with numerous body positions to find the ideal fit.

I've "loaned" him to kinky friends to teach them how to peg since we're now polyamorous. The women leave the experience wholly amazed and with much more self-assurance every time. In addition, I began instructing pegging classes. Not only is there a basic beginner's pegging session, but there are also classes on how to get pleasure from wearing a harness and how plus-sized pegging participants may make it fit with their bodies.

I would never, ever want someone to experience first pegging in the same way that I did. This is my "origin story," as you might say.

If I can draw one lesson from my experience, pegging must be an active experience for the bottom. I am aware that part of the fun and taboo for the pegging receiver is being the "receptive" partner who receives all of the top's activities, but being "receptive" doesn't mean you don't work hard. Most vagina-bodied people aren't used to penetrating things, and they most definitely aren't used to wearing strap-on harnesses and dildos. If you want your pegging top satisfied, you must contribute to that experience. In exchange, they will be more confident about pegging in the future.

Fortunately for you, we have a ton of articles on Kinkily that will make your strap-on sex exciting right away. Avoid the same errors that I made.