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.