beg2bepegged2

I’ve been fucking guys in the ass for some time now.

With my notoriety as Ruby Ryder, I think many people believe I get to fuck guys all the time and that I must have a ton of experience. Measurements of that kind are so subjective, though. What might be a ton to some would barely register with others. My own measure of it is that I have fucked far, far fewer than I could have, because I am particular.

I have met astonishingly handsome men who were never invited into my bed, for a variety of reasons. I have met sweet, thoughtful, intelligent men who never made it to my bed, either, lest you think it’s all about how beautiful their asses were. For me, the combination has to be just right. And of course, the chemistry has to be there, or it’s pointless.

I tell you this to point out that in actuality, I have not had that much experience pegging the sweet asses of multiple men, or even just one man. Probably less than many of you assume. Besides being particular, I have been single most of the last three and a half years.

So leaving the assumptions about fucking asses aside for a moment, let me tell you what’s been happening in my life recently. I have been working out regularly. I found the magic formula that gets me to the gym! A handsome young man (a friend) texts me every day and asks did you work out yesterday? (Doesn’t hurt that he’s in the military, too.) I don’t mind telling him ‘no’ one day, but if I have to tell him ‘no’ two days in a row, it rankles. So I have made it to the gym far more often in the last month than I have for quite some time. I have been cranking those weights up higher and enjoying the burn. I have conquered the land of the elliptical and now enjoy the heretofore-elusive second winds. I feel good.

So, after all that preface…I had an extraordinary experience the other night.

I hit my stride fucking an ass.

That’s the only way I can describe it. I had all the strength I needed. I felt agile; keeping my balance was easy. My core strength had such power and endurance that I was sort of throwing him around the bed like guys have thrown me around before. I had him in missionary position at one point holding his legs up and I impulsively put both ankles in one hand on one side of me and continued fucking him sideways. I actually did it because I was remembering positions guys have put me in, and with my newfound strength and agility, I felt like a kid in a candy store. I wanted to try it all.

Let me at this point gratefully acknowledge the lovely ass I had the pleasure of fucking. Because, as usual, I walk the line between preserving anonymity and fleshing out my story, but I do not want to talk about him like a thing. He’s so very much more than that. I’m going to call him Gorgeous Guy, because he is. He and I started talking a couple of years ago on FetLife and kept missing each other. Finally, we had a couple of dates early this year. Excellent chemistry.

So I invited him to join me last March at the BIL conference. In a lovely hotel room. With a king size bed. And he stood me up. He had his reasons, of course, but I don’t take kindly to being stood up without a word. So I answered his messages politely after that but blew off his advances.

Six months later, he finally convinced me to have dinner with him again. After all, Gorgeous Man is…gorgeous. More importantly, he’s charming, intelligent, and sweet. We had dinner. Then he convinced me that what happened was an anomaly; he’s usually very dependable and he’d like another chance, please. He had a lot of things going on in his life at that time.

We kissed. What little defenses I had left, forgotten with the sheer compatibility of that kiss. Wow. Added to all his other lovely qualities, well, yeah. I was done.

So we played. And it was Gorgeous Guy’s ass that I hit my stride whilst fucking. Couldn’t have wished for a nicer one.

I felt like that silicone cock was a part of me, I swear. I could tell the exact moment when his ass opened up and finally allowed the toy he’d selected from my collection to talk its sizable way inside him. I held steady, waiting for him to adjust to it. The muscles in my thighs and my arms worked hard to hold the position. I watched his open-mouthed closed-eyes expression; the softening…the letting go. Always a beautiful sight.

Later, I lay on top of him, deep inside, with my breasts against his back and only sweat between us. My hips moved with such ease. I put subtle moves on that cock, man. I made him moan and swoon. I was right there.

I owned that strap-on…and that ass.

We played for a long time, and slept soundly that night. Before we slept, I talked with him about how hitting my stride had felt. The best analogy I could come up with was the difference between the first time a guy fucks a girl, and then years down the line after he really starts to get good at it.

So…I feel like I finally have the amazing pegging skills that many of you have attributed to me long before now. Don’t get me wrong…I haven’t had any complaints. The night with Gorgeous Guy was different, though. I have to say that from this side of the strap-on, it was fucking amazing.

No, actually, it was amazing fucking.

 

Yes, there are indeed many women who love pegging. All women are different and their specific reasons for enjoying strap-on sex are as many and varied as the individual women are. Some women enjoy pegging as another tender, sensual addition to sweet lovemaking. Some like to combine it with other kinks (and those are many and varied as well). Certain themes rise to the top when women talk about why they like pegging. The vulnerability of the man. The taboo aspect. The pleasure of running the show. The fascination of sexually switching places. The deepening of intimacy.

I most definitely love pegging. I know, no surprise there!

But what is it exactly that turns my crank when I don a strap-on and peg my guy? My, my, my…so many things.

The Pleasure Principle

More than any other reason, I love to peg a man because it brings him so much pleasure. Some time ago I had the privilege of introducing a new  lover to pegging. After he came exquisitely hard in his hand while I sunk deep inside him…he gasped, “I had no idea!” I love the cause and effect of watching a man’s body react when I thrust inside him. I love the moans and gasps I can elicit. Pegging allows me to actually be inside him giving him pleasure, which is a thrill in itself; the only time in sexual play that I get to do that. But mostly…I just love to put a man in ecstasy with my strap-on.

Open up, Baby

There is a vulnerability that is necessary for a man to be penetrated. I don’t really see that with vanilla sex. A softness in his face. His eyes become a little unfocused or they close. I love that vulnerability. I love to see a man purely receptive and open…it is a rare and beautiful sight. That vulnerability makes me want to gather him in my arms and fuck him sweetly and continuously until he comes with cries of passion.

Happy at the Helm

I love…running the fuck. I am in control. I can tease him…or pound him…until he begs for release or respite. I can change the angle of my toy just a bit and know it’s driving him crazy with pleasure. Or I can stay still, buried inside him and drive him crazy with wanting more. I am wearing the dildo, so I get to decide.

Forbidden Fruit

I love the taboo aspect of it. I mean, as taboo thrills go – fucking a man in the ass with a strap-on dildo is like the Dubai Tower of illicit sex thrills for me. But also there is the whole ass thing. Sadly, asses suffer from widespread discrimination. People who are happy to dress up their derrière  in sexy articles of clothing designed to attract widespread attention…would never think of  undressing that ass and actually taking it for a drive to see what it can do! Asses are often thought of as a dirty, nasty place that serves only one function, period. Well, let’s see…dirty? Absolutely. Which is why you wash it really, really well before you start playing with it!  Nasty? Yes! Nasty with a capital N and an exclamation mark. The juicy, titillating, throbbing, aching, fun kind of nasty. …Serves only one function? Well there are many many gay men who would beg to differ…and thankfully a growing number of straight men who have also discovered the joys of anal pleasure. *steps off soapbox*

Deliciously Dissident

Flouting  intolerant opinions is a hobby of mine. Above and beyond the ass itself, a lot people have judgments about pegging, from both sides of the dildo. If you are a man who likes pegging, clearly you must be gay…and if you are a woman who likes pegging, you wish you were a man. I love flying in the face of all those judgments and doing what I want just because I enjoy it. Sometimes I think that I gravitate towards kinkier stuff because there is a part of me that resists anyone telling me what I  should or shouldn’t do, most especially in the realm of sexual exploration. So if people view something as taboo – damn, that might be a hot thing to try! I am a bit of a rebel at heart. Does it give me a charge to know that if I told some of my friends about my proclivity for pegging, they would be shocked? Indeed it does. *smile*

The Visuals

The delectable vision of spreading those cheeks and sinking slowly into his ass…that is one of the hottest,  most amazingly arousing visuals I have ever seen….like, ever. Now I know why some of the kinkier dating sites that have amateur videos are overrun with clips of men holding a video camera pointing straight down as their cock is sinking into their woman who is on her hands and knees…I get it, guys! And from a different position, the look on his face when I am stroking my strap-on in and out…that surprised naked passion sort of OMG-what-the-fuck-are-you-doing-to-me-I-love-this look. It’s incomparable. His hands reaching back to pull his ass cheeks apart. Riding me and stroking his cock. So many visuals! Who says women aren’t as visual as men! If more women tried pegging perhaps the numbers would change.

My Pleasure

Do I get pleasure? Oh yes. Oh God, yes. Dripping throbbing, aching, clenching pleasure…without a doubt. I’m playing with how to orgasm while I am actually pegging my guy. Some women do…and I want to join them in that singular pleasure. There are dildos that offer a vibe in the base that are slated for experimentation…I’ll let you know how it goes. Might take a lot of practice…I don’t think he will mind.

Yes indeed, some women love pegging!.

Ruby Ryder