I came across Jack from Kansas on the internet, and found this piece in his writings. I have long put forth the viewpoint that pegging usually involves intimacy. In fact I have written about exactly that. This piece is about how getting pegged by a stranger can be different than what you envision. He graciously gave me permission to post this here.
Pegged by a Stranger? Sure, what could possibly go wrong?
There are more than a few guys who want to be pegged badly, so badly that they will seek out the profiles of the women with similar interests and message them, offering up their asses blindly. Hell, there are even pages and sections where you can post ads in the hopes of accomplishing this.
I used to be one of those guys, and this is what happened to me as a result.
Long ago, I knew that pegging was the fetish for me. I had experimented with vibrators, butt plugs, and dildoes while masturbating and had come to enjoy the sensations, taboos, and pleasure that accompanied ass play.
Toying my own ass is great, but you know what would make this even more awesome? If a woman was doing it to me! Nothing wrong with that logic.
One day, I was introduced to a kinky website and after establishing my profile and looking around a bit, I found what I was looking for, or so I thought... Interest groups involving pegging!
I started seeking out women with offers to let them "practice on my ass" and other attempts at cleverness, sometimes asking outright. "Hey, you like strapon fucking, and I have an ass, would you like to fuck it?"
I always received the answer that I would now expect, if any at all. This was back when I wrongly assumed that it was a hookup site, and I would be confused and frustrated by the lack of shared enthusiasm. "But you have a strapon in your pic! You're supposed to want to fuck me!"
So I did what I thought was the next best thing... I posted an ad on a different websites notorious for catering to cheap sex.
I was contacted by a woman (after a lot of searching), and we did the awkward dance of email chitchat and pic exchanges, until she agreed to meet me at her place for a pegging. She had some experience in this area but wasn't a pro. I showed up and we spent a bit of time on the sort of mindless pre-sex small talk that strangers tend to do, then we undressed and it was showtime.
We did a bit of perfunctory foreplay and then she asked me if I was ready, and I was sure that I was. She strapped the dildo on, and She had me lay face down on the bed with a pillow under my hips. I spread my legs and felt a cold dollop of vaseline hit my butthole, and it hit me that this was really about to happen and I was nearly at the point of no return.
She began working a couple of lubed up fingers into my ass, and all I could think was "this is kinda uncomfortable...", as it was a bit more forceful than I had anticipated. Still, this was my fantasy and I was probably just nervous, no big deal.
She then withdrew her fingers and knelt on the bed behind me and slowly began working the dildo into my ass. Not so bad, I thought as I felt it gradually pushing deeper and deeper. When it reached the point where it began to hurt, I told her and she used that as her gauge. She then began fucking me.. slowly at first, and then gradually increasing speed.
I had 2 simultaneous thoughts; the first was "Hey, this feels pretty good", and the second was "I don't know this person". I was unable to fully relax and let myself go because I didn't know her, and I soon found myself staring at the headboard and trying to think of something to say as she pumped away.
I can be very vocal when I am having good sex, and I was letting out little honest gasps and moans of pleasure (because it did feel good)... but I was quickly starting to feel self conscious doing so, and it occurred to me that this must be what faking it feels like.
It didn't take long after this point for me to lose my focus and become pulled out of the moment. The pleasure began to seep away to be replaced by pain. While I was losing my inner battle to just relax and enjoy this, she was busily pounding away at my ass, harder and harder. "You like this, baby? Does that feel good? Take it!"... these were met my my grunts of what were now becoming pain. My ass was being fucked HARD and painfully, and I had put myself in this predicament.
Eventually I could not take it anymore, and I was actually gasping and crying out with every thrust. "Too much! Slow down!" A big drawback to a scenario like this with a stranger with whom you haven't set any boundaries is, she didn't know how to read me and thus didn't know I was serious. If anything, it excited her more. Finally, I had to yell for her to stop as I quickly crawled forward to get free of the dildo.
We were both panting and sweating, and she dropped on the bed beside me, smiling. "How was it?" she asked, seemingly oblivious to the fact that neither of us had attained an orgasm and that I had no trace of erection by that point. I told her that it was a lot rougher than I expected and I didn't really like it as much as I thought I would. And that in retrospect, this probably was a bad idea.
Her reply was "Hey, you came here wanting to be pegged. Don't blame me...", and she had a point.
We didn't know each other. There was no mutual respect, and almost zero communication. What was supposed to be a pleasurable fantasy experience ended up being little more than a stranger ramming a dildo into my ass with no regard to my feelings... because I asked her to.
The lesson here I suppose can be paraphrased from The Big Lebowski: "This is what happens when you fuck a stranger in the ass!"
I should note after some reflection, I was still a pegging enthusiast. I was also a little smarter. Since then, I've gone on to have subsequent pleasurable experiences with different partners, largely due to the fact that the pegging was included as an enhancement to sexual activity rather than the sole focal point. And I now do what I should have done in the first place... get to know my partner first.
UPDATE In response to some of the reactions I've received to this writing, I should point out the fact that I probably depicted her as a cold, callous, and unfeeling domme. But she was actually very nice otherwise. Just not very... experienced or empathetic. She was not a domme, just a lady with a strapon and a willingness to use it.
We still keep in touch now and then, but not in a sexual sense.
I'm thankful that Jack provided an eloquent bridge here, between my lecturing guys that pegging involves intimacy and their desperation to experience it, by way of a first person story about how it actually felt for him to have his first pegging experience with a complete stranger.
Communication and negotiation are so important before any clothes come off, and knowing the person a bit is a good idea as well. Pegging can be so new and potentially awkward because of the role reversal that for many people it's easier to navigate with a partner you are already intimate with.