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.
Swiftly I felt Ali's foot leave my leg and saw her shuffle a little before nylon covered feet were placed either side of my stiff member, and they slowly got to work. I watched Ali all the time, her feet were easing up and down my cock, then one at the front whilst the toes of one felt like they wrapped around the back and gripped the flesh hard. The sensation was amazing, so unusual and heightened by the time and place it was happening. I stroked Ali's calves under the table, loving the feeling of her slim, toned muscles moving lightly under my touch. However I could not deny what was happening, my cock was sensitive to everything she did and she was deliberately working me, bringing me to a state of arousal so quickly I wasn't sure I would hold on.
"You sure??? This could be messy.... you are working me sooo close, can I stop you?"
"No... you are losing the bet, and if you recall, when, where and how many times you cum tonight was in my control... this is the first.... and as you suspected, now I win the choice of toys too...!
Ali's feet were working the tip of my cock gently, massaging it, then stroking its full length and I knew it was close. The she slicked a finger between her lips, smiled and held my gaze as she dipped her hand out of sight. Her movement left me in no doubt where that finger had now found itself and its a good job she had chosen this restaurant and table... God, I was going to cum...
"God, Ali... cumming... oh, ner, aargh. Oh fuck... ", I whispered trying to keep my exclamations quiet as my orgasm took hold. Her feet worked my cock as she felt it tense even harder and the first pulse of hot, white cum spurted upwards and out of my raging hard member. I watched her face, not caring where my cum landed, trying hard not to jerk as spurt after spurt shot out of the now sensitive end of my cock. I was trying to act normally as my cock erupted and I made as little sound as I could. Ali seemed mesmerised and was playing hard with her pussy as I came, her eyes a little glazed as she felt my orgasm through the contact with her feet. Finally, I was spent, and I rested back in my chair and looked down. Ali's gloriously sexy, nylon covered feet, and my slightly softening cock, were now coated in creamy white cum...
"Feed me some...", Ali whispered, as she shuddered, her fingers bringing her to a small orgasm in front of me. I raised my eyebrow, but Ali just nodded, and I could see small movements of her hand were still keeping her busy.