I've been fucking guys in the ass for some time now. But recently I discovered there was more to turning a regular encounter into amazing fucking.
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. The land of the elliptical has been conquered and now I 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. In missionary position at one point I held his legs up, and then impulsively put both ankles in one hand on one side of me and continued fucking him sideways. 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 Guy 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.
That silicone cock felt like 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. He moaned and swooned. 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.
11 Responses
Just one more reason for me to get my happy clappy butt back to the gym!! 🙂
Gym = highly recommended, yes!
Indeed! As you’ve mentioned before, it takes some strength, some balance, some endurance to use a cock well, strapon or natural, precisely because of the thrusting, the pulling, the pushing, and all the delicious other movements that are so satisfying. (And please, let us not forget the oh-so-lovely squirm against the lucky man’s ass!)
So the extra wind, the extra core and leg strength — they can truly make a positive difference!
How many men have written to you, Ruby, to say it’s so important to them that their ladies enjoy themselves when they strap on their dildos and become the one who penetrates? You have certainly provided stellar advice about one means for adventurous ladies to ramp up that enjoyment.
Your lucky partner no doubt will agree.
And all the other benefits to top it all off — they are not to be discounted. If better strapon sex is the goal, the side benefits of feeling better, sleeping better, having more daily energy . . . well, where is there even one downside? For the guy? No way. For the lady? No way, for sure. And for everybody these two fortunate souls encounter in the other aspects of their lives? Most assuredly not — more smiles on the faces of Ms. Strapon and Mr. LovinIt make everyone’s day a little better.
You bring up some great points. My enjoyment of pegging in this situation was very much about mastery and being able to bring so much pleasure to my partner in a way that felt intensely connected. The equipment I was wearing was not the choice that would have possibly gotten me off. He chose a flared-base dildo with balls. Whereas some women can get off with just the pressure against their clit – it ain’t gonna happen with me. Now when I finished, I was dripping. So it was hardly all about him. Mutual pleasure was had.
I love this! We need T-Shirts like this!!!
Well written escriterra, as are you detailed stories I’ve enjoyed reading on literotica. Agree with you the man being lucky, believe the woman’s a lot luckier to get to enjoy something she likes like this e.g. the intimacy, embrace, the act, the view she gets, the pleasure she’ll get hopefully from knowing the pleasure he’s experiencing.
Ruby, now you’re speaking my language. Bring pleasure to each other. Also feel intensely connected not just physically, mentally as well 🙂
Wow what an amazing story thank you so much for sharing! I’m not sure if this is the right place but I’ve had a fairly recent experience with my lover that I think brings a new perspective to whole pegging=gay dichotomy.
Well first of all I’ve been with my lover for about 1.5 years. He saw my ad on Craigslist and hired me to tutor him in physics. Despite our age difference (him 23 me 48), we had a powerful connection between the two of us. As an older woman I was surprised he took interest in me, and even tho he was slightly shorter than I like my men, he had the looks and body of an Abercombie model that would make a woman of any age swoon.
After 3 weeks of tutoring sessions, he asked me out on a date and we’ve been romantic partners ever since. Also, pegging has played a very prominent role in our sex life. At first he declined my requests to peg on account of “feeling gay”. But after he gave me a night to get him well acquainted with his prostate, he put those fears to rest. However, 2 months ago he told me that he had been having fantasies about being with another man. He said that he loved the feeling of being penetrated and the feeling of being fucked and was curious what those sensations would be like if they came from another man. I encouraged him to further explore those feelings with me and two weeks ago, after finding the right guy, my boytoy had his first experience with another man. He absolutely loved the experience, and I found it to be a beautiful display of primal passion.
What I’m trying to get at is that, no, pegging will not automatically make you gay. However, partners should be open to the fact that as boundaries are broken, pegging may encourage or spark desires of being with another man.
You are absolutely right. I used to say that pegging a guy cannot turn a man bisexual, which I still believe is true. But if a man is bi-curious, it will probably make him even more bi-curious. And many times those feelings of bi-curiosity have gone unexpressed and unacknowledged. So it might indeed appear that pegging is the catalyst, and sometimes perhaps it is.
That’s great Ruby!
I’ve been looking for some time for this kind of pegging. It’s really important for the woman to have some kind of physical control and thrusting power, but still preserving her feminine movement and fluency…That’s the combination I love!
It really is a fantastic feeling when you feel your loved one behind your back keeping you tight, pulling you towards her, pushing her hips into your bum and making that clapping sound, the ass cheeks jiggling from her thrust…it really is amazing 🙂 I lived that.
For that it’s also important for the guy to lose some weight, if he’s too a hunk of a guy, so the girl can have some control over him. For me it’s not a problem, I’m a relative thin guy (but still in shape) and that’s why I know why this is a good thing to be in this situation 🙂
Sorry for the eventual grammar mistakes 😉
Physical fitness definitely plays a part in attaining the most enjoyment from pegging, no doubt about that. Good luck with your search to find that kind of pegging!
Annalise, that is my ideal fantasy. Awesome, thanks for sharing. For me, having her there with me when I am exploring myself with another man is very critical to the entire fantasy. I’m not looking for a gay experience. My fantasy involves her coaching, talking, describing how she feels and what she is seeing happen, what she wants me to do. I’m happy for both of you. Enjoy!!!
You might have seen this and/or find it interesting, titled: “What do I get from Stapon sex? A LOT!”
http://wyckedjasmine.tumblr.com/post/101166591578