ANAL SEX
How One Woman Went from Hating Pegging to Making It a Weekly Part of Her Sex Life
Published: FEBRUARY 26, 2021
| Updated: JUNE 28, 2022 03:19:44
Pegging: the sexy story of how one women went from "hate" to "heart."
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!
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.
Strap-On Play: Boldly Going Where I'd Never Gone Before ...Literally
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 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.
A Not So Sexy Struggle with the Harness Kicked Off Our Adventure
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.
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.
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.
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.
He Was Naked ... and We Had Another Problem
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.
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.
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.
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!
Read: A Step-by-Step Guide to Giving Your First Pegging
All the Attempts, None of the Fun
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.