Careful What You Ask

I knew from the way she looked at me...I was in store for something. What that something was I couldn't be sure. Half lidded eyes with tons of eye contact. Her skirt could not have been any shorter and the fact that she was also crossing her legs caused my cock to fill my jeans uncomfortably. Her languid manner unnerved me a little. I sipped my beer.

I'd asked her out on a whim. I saw her sitting in the library off in a corner by herself. Glorious rich brown curls fell to her shoulders, framing her pretty face and full red lips. Reading Dostoyevsky, for God's sake! How could I not ask her out? Brains in a woman always turn me on. That she was hot as hell certainly cemented the deal. So I turned on my charm and sat down not too far away. We discussed our favorite classic literature for a bit and then impulsively I asked her out. She looked at me as though I had no idea what I was getting myself into and hesitated just long enough for me to change my mind, which I resisted. Then she said sure - she'd love to.

Thursday morning we'd had coffee and I'd discovered a remarkable intellect underscored by a playful sensuality; her insides were as hot as her outsides. Friday was dinner and a long sexy kiss at her front door that made me pull over on the way home to rub one out. This was Saturday and we were at a dive country bar drinking beer and taking turns asking each other questions. Our mutual interrogation took the inevitable turn to more lascivious subject matter.

"What is your favorite thing to do to a guy in bed?" I leaned into her as I asked the question, wanting to keep it private in the busy bar. That's when that look appeared on her face; appraising, reeking of self assurance and hidden parts I so wanted to uncover. I briefly fantasized her answer would be - give him a blow job. Wouldn't that be cool?! When she paused even longer, my attention, and curiosity, were piqued.

She blinked once, slowly and looked right into my eyes.

"Fuck him up the ass with a strap-on dildo." Her smile was sly and sexy, enjoying my instant discomfiture.

Only one word would cooperate and come out of my mouth, barely audible.




Visions of strap-ons and dildos and my ass and her naked and me submitting and her fucking me all went through my head in the next 5 seconds. Our eyes were locked.

She stood up precipitously and grabbed my hand, pulling me up and through the noisy crowd to the door. As soon as we got outside she pushed me up against the wall and kissed me hard, drawing surprised looks from the circle of smokers.

"My house?" Her question arrived in a sultry voice that left no illusions as to what she was really asking me. Nervous as fucking hell, I could only nod. Instantly she pulled me over to her car. She drove the few miles to her house.

What the fuck had I just agreed to? It wasn't too late to change my mind. I could just tell her no...if I could open my mouth and get just one god damn word to come out. Jesus! I was sweating lightly and felt more flustered than I could ever remember being.

But I knew I wouldn't change my mind. I'd been hard as a fucking piece of granite ever since she'd answered my question.


My cock pursued her through the front door...and I followed helplessly.


©Ruby Ryder


(By popular request, this story has been continued in a full length story in my paid memberships - "He Said She Said".)


Ruby Ryder
Ruby Ryder


19 Responses

  1. This submissive male also loves the story from the inferior male’s perspective. Since you already have the superior female perspective, it makes this reading even better. This story and the previous are fine pieces of work!!

  2. Thanks so much for your kind words. Although I don’t have the same viewpoint that women are superior than men…I welcome everyone here on Pegging Paradise and really appreciate your comments!

  3. Ahhhh so good to see this site. I’ve just discovered there is a name ‘pegging” from what I’ve done for years. I love love doing this, and not because I need to feel superior. I just like ‘dat azz’! My husband wanted to be the bitch in bed, and after a few years he pretty much got his wish. NOTHING like tonguing a sweet clean hole attached to a sexy bubble butt…feeling him move like he’s never ever imagined such a thing to feel so good. LIKE A CAT IN HEAT I tell you….Husband passed, and now what do I do? How do I explain on [vanilla dating site] that I like dank & drilling assholes? Here’s my note to the universe: I need one again!

  4. Closet freak – welcome to Pegging Paradise! So nice to have you join us. I agree, bubble butts rock. 🙂
    So sorry to hear your husband passed.

    You might want to try to find another happy strap-on fan to peg. WAY different than the vanilla dating sites, but a great place for kinky folk.

  5. Closet freak,

    We are all over the place. My wife has done it many times, originally at my request. It is just a matter of finding someone. A lot of closet cross dressers like it. The problem is that no one knows. Look for clues to cross dressing. Usually men that you wouldn’t even think would go for that. btw if a man finds it uncomfortable, he may want to try it a few times before he decides it is not for him because once you learn to take it, it gets way better. Go to chat rooms at yahoo and get to know someone for awhile.

    1. Well, you can go to the “tag cloud” on the right side and click on “does it hurt?” And do some very very interesting reading. But the short answer is that, no, done correctly it not only does not hurt, it can provide a man with an orgasm about 10 times more powerful that anything he’s ever experienced. Common misconception, though!

      1. Definitely can vouch for the 10x orgasm and done well, there’s little to no pain. And, by little I mean no more, probably less, than the accidental pain we cause each other in any other sexual circumstance.

        1. Thank for the confirmation of my assertions – since I don’t have a prostate!
          I maintain that done slowly enough, there is no pain, but most people don’t slow it down that much, despite my admonitions!

  6. So true – you have to be careful what you ask or wish for! it’s a slippery slope from a stud muffin to a cutie pie (but only if you like your guys girly).

  7. once, i was at a bar with a fuck buddy of mine.. he asked something similar and i told him that i love pegging.. he stood up and left so scared… 🙁

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