We met as Ali requested, in the secluded and quiet restaurant close to her apartment. She looked stunning and I knew as soon as I saw her that my decision to agree to her rules for the night was a good one. I shivered, the anticipation building and making the hairs on the back of my neck stand on end already. In our planning we had agreed the boundaries, the rules if you like. I was dressed as I was asked, Ali had made a few requests that in reality were not choices for me, but expectations. Not too difficult -- the silk boxers already teasing my hardening flesh, the dark blue chinos brushing softly against my legs and the sleeves of my white shirt just rolled back behind my wrists. Casual shoes, completed the outfit, nothing to what Ali was wearing and I wondered what was underneath her fantastic outfit. I knew I would find out in due course, but for now I feasted on her shimmering black low cut top showing off her full firm breasts, and her clinging, silky red skirt, ending well above her knees. The fine black nylon covering her legs would surely be stockings, and her slim legs were set off by the steepling heels, peep toe and patent black leather ....
We ordered, I recall her saying that the food she most liked to get her in the mood was strawberries and chocolate. I could see this was on the menu but the light salad gave us time to start our flirting seriously. We sat opposite each other, and I felt Ali's foot slowly stroke my leg, feeling it work under the hem to briefly rub the flesh of my ankle before working up until her toes rested on my crotch. All the time we locked eyes and spoke of other things, but her foot was working my thigh tops and starting to press against my balls and hardening cock.
"Mmm, someone likes this treatment, how long before I can get you to cum.... take a bet?"
Ali's voice was low, seductive and she licked her lips after she spoke. Her deep red lips were shiny with lip gloss, drawing my attention to them immediately as she spoke again.
"I bet you will cum before we leave here.... what's your gamble? Shall we say.... winner gets to choose a toy for use on the other one???"
I reached down and lightly stroked the nylon covered foot still working on my crotch, fondling Ali's foot, her toes, stroking her ankles and heel, around and starting to work up her calf before the waiter returned. All the time Ali tried to keep rubbing away, pressing onto my ever growing bulge. I could lose this if I was not careful!
"Mm, OK, but I am at a disadvantage aren't I? This is your night remember, your choice of where and when I cum anyway, surely that's unfair!"
Even as I said it Ali was rubbing her stocking covered foot in circles now around my cock and balls, but through the fabric of my chinos the pressure was just about bearable. She leaned forward, giving me a fantastic view down the front of her silk black top, her full, firm tits a little more visible as she smiled.
"Yep, that's such a shame... still, if you can resist until after our strawberries, then you win. But its going to get harder, literally.... I want you to visit the rest rooms and remove those silky boxers, we will have a use for them later... but now I want access."
I raised my eyebrow, but the opportunity to get away from her insistent foot was a relief, so I sped off to the wash rooms, very aware of the obvious bulge in the front of my trousers. No-one seemed to notice, and I was quickly back in my seat, silk boxers in my pocket and facing the gorgeous Ali again. Ali made no reference to the gamble as we ate the salads, and the wine flowed a little as we sparked off each other. I love our conversation, it roams everywhere and Ali has a sexy smile and a knowing look in her eye, especially when the chat turns horny as it did now. We got back to the subject of our game, the results of which was our night where I had agreed to turn over all responsibility for leading the sex to her. She teased me about how often she would use my body for her own pleasures, and her body was a lovely one to please. We touched hands, caressed arms, and I felt her foot slide around my leg, the nylon sending shivers through me again. After a brief kiss across the table, and whilst we waited for the strawberries in chocolate, Ali asked me to sit back and quietly, discreetly undo my trousers and slip the zip down!
I raised my eyebrow, and asked what the consequences would be if I refused. Ali looked at me and said, smiling sweetly all the time, "You don't do this now, you lose the bet, you buy a strap-on for me and I fuck your ass off next week!", and all the while her foot stroked my leg and she looked the picture of innocence. I had never heard Ali talk like that, and I was aroused already. I toyed briefly with the idea of deliberately refusing to see if she would do it, but I am not sure as I am quite ready for such an act... so I reluctantly carried on. Discreetly I exposed my hard cock to the cool air of the restaurant underneath the table and hopefully out of sight.