I have to admit when I heard Ruby Ryder’s latest podcast that featured some questions about strap-on play from a UCLA gal, I was quite impressed. I have been saying that the younger men are much more open to and interested in ass play than men my age, even though it is changing. It sounded like, from the podcast, that Pegging is quite popular on college campuses. (All I hear in my head is Echosmith’s Cool Kids).
Pegging for those of you who are wondering, is female on male heterosexual strap-on sex. Ruby Ryder has been doing some of her Pegging 101 classes at my house lately and when I have shared our Facebook event, many have said they had to Google “Pegging”. The classes, by the way, are fun and garner a lot of interest, from men and women.
I have been meaning to try Pegging for quite awhile. I have worn a strap on before, but we didn’t really get to it. I have a willing and interested lover, but we have yet to try it. So, when I received this text the other day, “I can’t stop thinking of looking at your big tits bounce while you are thrusting in and out of my ass,” I was very excited! Especially since it was from a macho, macho man- a VERY hot firefighter- that I met a few years ago on Craigslist. (yes, there are some amazing people on Casual Encounters, just like me). I like to try new things, it is exciting to me, and variety keeps things interesting. This is a guy I see a few times a year. It is always good, hot sex and just that. I know very little about him, besides what I have found out from my initial Google vetting, so this would be interesting for me, as I had imagined that I would experience Pegging with someone whom I knew better emotionally and intellectually.
I expected this time to be hot, and all about him, as he is quite dominant and this would be a chance for role reversal. I didn’t expect it to be as hot as it was. First, wearing the strap on was pretty sexy and empowering. The sexual chemistry between us is electric. I don’t even know how many orgasms I had before I fucked him or before he fucked me. He knows exactly what I like and mmmmm his body really turns me on, as does the touching and kissing. In the past, our encounters were short and sweet, a lot of fucking and not much else, so I was surprised by the openness between us and how comfortable the communication was. Neither of us had done this before.
This was a very intimate experience for me to share with someone. It had some surprises too. He didn’t cum while I was fucking him, but he could have, if he would have allowed me to play with his cock more. He asked me not to touch his cock while I was fucking him he could hold out and fuck me later. I guess I kind of expected him to have an anal orgasm, but he didn’t. I did, however, orgasm, while fucking him, which was very unexpected. I also was impressed and I guess surprised at how gentle and guiding he was with me. There was a sweetness that I had not seen with him before. He guided me on how to hold his hips and what would make things easier for me the next time. Fucking from that side of the cock is hard! It was really sweet when he said, “It’s hard, isn’t it” when he noticed I was getting tired.
We tried a variety of positions that Ruby Ryder has taught about. I would have to say, I liked them all. Doggy Style was the hardest on my legs and core. I think I liked him bent over the edge of the bed the best because I could see his perfect ass and his amazing shoulders (I am a sucker for broad shoulders). I have large mirrors at the end of my bed, so as I was fucking him this way, I could still see his cute face. We actually started with him face up with his ass on the Liberator pillow (which is MY favorite way to be fucked anally). This allowed me to see his face as I penetrated him, and also for us to have communication as I entered him for the first time. This is an important part, as is the foreplay, that took place prior to me fucking him.
Pegging or any ass play isn’t something to try for the 1st time without prior communication and preparation. He had experienced ass play before and I lubed his ass up very well and fingered him before we used the dildo, again, with more lube. It is important to use lube, as the ass is not a self-lubricating orifice. We both found the experience to be very pleasurable.
Ladies, I know some of you are self-conscious about your bodies, but men would not be naked with you, if they didn’t like it! I know we like to feel sexy. The strap-on I have is cute but sat below my belly which is I don’t think is attractive on me. I usually wear boyshort panties because they come up higher on my waist and cover the tummy area. There are ways around this. There are a variety of panty-style harnesses and different even boyshort styles, it was just not what I had. Instead of feeling uncomfortable and exposed, I wore a fishnet body stocking with the strap-on on top of it. It made me feel sexy and comfortable. It helps that he also lets me know that he likes my body and reinforces it by grabbing our phones and shooting pics and video throughout. That is super sexy too, if you haven’t ever tried it.
I try to be in the moment and not think about what my body looks like or if I am doing it right or what might be going through my partner’s mind. This allows me to usually orgasm over and over, which is always a bonus! This is an instant that it could have been very easy to get into my head. Hot guy- perfect body… me- big girl, not in the best shape. Instead, I focused on this hot experience we were sharing and the pleasure that it created for both of us. Stay out of your head in the bedroom, it will make all of your experiences better!
