Her fingertips danced over the twin bulges in my jeans, and I knew she was not going to stop there. She wanted to touch me as much as I wanted her to. Just how she was going to do it, the anticipation was nearly painful.
I groaned loudly, and she smiled wickedly. She let her fingers dance back and forth, running them over the sensitive surface of my balls, just a bit of cloth separating her skin and mine.
She continued to brush her breasts against my legs, knowing that the visual was continuing to arouse me. She hadn’t really thought much of her breasts, her husband had never given her a second look, and as many middle-aged women, as they started to lose their firmness, she became unhappy with them. But suddenly she realized that her own point of view was not only limited, but not necessarily shared. As she teased me, seeing how she was turning me on, I could see her nipples harden, showing her excitement as well.
Her fingers moved up from my balls, and there it was, her fingers started running along the ridge under my zipper. Oh My God. She was touching my cock, she was actually pushing against it, stroking me. I desperately wondered what was on her mind. How shy was she? How comfortable was she? Would she just want to play a bit this first meeting? Would she even make me come, or would she just tease and make out, and leave with blue balls, so that I’d come back again?
Or would she stroke me until I climaxed while still dressed? So that I got off, but still never really touching me? Or would she go further, would she undress me, touch me? I decided to let her choose the path we would take.
I could tell after just a minute that she wasn’t going to let me keep my pants on. In our emails, she had told me she loved oral sex, and now it was obvious she didn’t want to wait to experience it again.
Her fingers made it up to the waistband of my jeans, until she found the wet spot forming at the top. Twirling her fingertip around several times, the spot grew.
My head spun. I’d been with the same woman since college; that’s where we’d met and had gotten married shortly thereafter. She was the only woman who’d seen me completely naked, and except for a brief encounter over a decade ago, who’d touched me, who’d brought me to climax.
And now, a new woman was touching me, was about to unzip me and touch me even more intimately… the experience was quickly becoming surreal. Online flirting and some naughty talk was one thing, actually meeting someone and becoming physical was a whole different thing. Yet it was actually happening.
Then her fingers slid back down, gently, and then back up. Finally she found the zipper pull, and looked me in the eye as she started to pull it down, just a bit, then more, and more, very slowly pulled my zipper down, letting the sides of my jeans stay in place, keeping what was underneath hidden from view for the moment. But the pressure against the inside of my jeans was released, my erection was no longer restrained.
Finally my zipper was all the way down. She had made sure to touch just the sliver of metal, no pressure on the throbbing ridge underneath.
The sides of my fly were bursting open. She let her fingertips wander down both sides of my fly, letting me burst open, now just constrained by my underwear.
She looked at the ridge, now more clearly outlined, bulging in front of her.
As they reached the tops of my thighs, her fingertips started to move toward each other, down the insides of my thighs, which, already open for her to kneel between, opened even further. Then they started to dance back up my legs, and as they approached each other, she moved slower and slower, so as to lengthen the anticipation of them touching me intimately.
Inside my underwear, I was completely and fully erect, rock hard and throbbing, aching to be released from the tight confines. Normally that would be all I had been thinking about, but my eyes had other plans for my brain, as I watched her tease me, her breasts moving up and down my thighs and her fingertips playing in the vicinity of my crotch.
When would she actually touch me? How would she do it? What would she touch?
She ran her fingertips over the bulges of my balls, then gave my zipper one last tug. Finally, she couldn’t pull the zipper down any further. Looking up at me, she placed her hands on both sides, and slowly pulled both sides of my pants aside, exposing the purple briefs that she had seen a hint of in a picture I had sent her.
“Ooooooo, yes! I was hoping you’d wear them!”
“Oh really? You were planning on seeing them live? You had plans?”
She looked at me and smiled. “A girl can dream, right?”
Then she looked down and took a closer look. I was bulging through the thin cotton, the ridges clearly visible. He was right there, throbbing, waiting for her fingers to touch.
She traced her fingertips up and down the shaft, each time getting closer to the top with each stroke. Finally her fingertips reached the upside down heart formed by the ridge that separated the knob and the shaft.
She looked up at me and wickedly smiled again, and pressed her fingers against the middle of the shaft. She pushed up and down several times, each time, urging the material to slide down further, only the waistband preventing the knob from popping out the top.
We each waited, to see if it would pop out ‘accidentally’…
Source: reddit.com/r/gonewildstories/comments/boovid/surviving_my_first_craigslist_encounter_f_pt_4