Coffee Shop Roleplay

Jenice and me have been friends with benefits for a while now. Our interludes are few and far between but often enough make for a great release of tension for the both of us. Jen is drop dead gorgeous with a great ass, a rack that gets my heart racing every single time I see her and long legs that give me a hard-on to last all damn day! I've known her for a decade but even now, she feels just as decadent as when we'd first started out.

Jen has a great sense of humour, is tremendously successful, and is a dormant exhibitionist that I love instigating to action from time to time. Jen lives close to where I work and will occasionally drop by to meet. I never know which of our meet-ups will end up being hook-ups but in not knowing lies all the thrill. Jen does give me obvious hints when she's in the mood - she knows I love her tits so will show me ample cleavage to tease. She doesnt know I love her long legs in a skirt or her cute ass in a tight pair of jeans just as much but that's ok. Its good to be able to have something that I can read!

Jen was returning from a long client meeting and was looking to bounce some her ideas off me on the way back so we decided to meet at a coffee shop nearby. She was dressed in a formal pastel shirt that fit her snugly with a pleated skirt that sat just above her knees and her hair in a ponytail to put together a look that said she was a boss not be messed with. We sat down with our cups and she went on to tell me about her day. Sounded like a typically exhausting, busy day filled with the energy that focuses on getting things done, her way. While I do love hearing about her work and her plans with a passion of someone that loves doing what they do, its also a quality that turns me on immensely.

I couldnt help but flirt, complimenting her long hair, her smile, the look she had going that day until she finally melted out of her business frame of mind and a hint of a mischievous smile with a playful reprimand finally found a way on her lips. Jen loves talking about her recent crushes and I know it also gets her worked up so I deliberately brought the subject up. Turns out, she had a new hire that was quite the eye candy and when I learnt he had accompanied her on the client meeting, I teased she was dressed inappropriately and stood no chance of enticing him in any way. She countered that she needed to dress formally and be professional with her employees. I reminded her that she was the queen of subtle hints and too big a cock tease to be using that excuse!

I offered a quick role play - I'd play the new hire and she could play the enchantress as we danced around each other at the cafe on a normal work day. If her methods couldnt get me at full mast (she knows what my full erection feels like in her hands), she would have to do what I said and the roles would be reversed with me being the hunter. If I lost, the second trip to the washroom would be mine and I'd have to rub one out myself with pics to Jen to prove I was done. We'd each get 20 minutes at our turns at enticing each other. If she lost, she'd make the second trip to the washroom on my terms.

Jen is really competitive and she hates to lose. To be honest, I was at half mast already and knew that just some dirty talk from her would be enough to take me over the edge. I was determined not to lose though, it wasnt every day that Jen agreed to do my bidding, even if the stakes were stacked against me. While she agreed, she added her own stipulations - We'd be out here in public in both the 20 minute windows (not that we'd need the second 20 minutes!), and that we wouldnt get physical even if she lost this stupid game.

I agreed.

Jen returned from the washroom with her her let open, a couple of buttons undone to show the kinda cleavage that can drive a man mad and her skirt just half way up her thighs. If she'd put her hand on my shaft, I'd have lost the game right then. She knew as well and had that smug look she has when she knows she's getting her way. But the setting faltered her approach. Her long legs were hidden under the table and while she did her utmost to lean and open up her shirt to show both cleavage and her lacy white bra, it wasnt going to be enough!

When the timer rang at the 20 minute mark and she reached over from under the table, she felt my half mast and looked over with a mix of anger and disdain. Said she felt insulted that I didnt seem to be as attracted to her as before. I smiled as wickedly as I could and told her to wait in the stall for my text. She buttoned one up and huffed away to the washroom. She messaged a fresh set of conditions - I'd have to get her dripping wet without touching her or asking her to show more cleavage or leg. I agreed. My plan didnt involve exposing her, not how she thought of it anyway!

I wrote back -

"Agreed. Here's my list:

1. Remove your bra and panties. Put them in my lap when you come so I know you've followed through.

2. You can use your long hair to cover your erect nipples that I know will betray your attempts at self control.

3. You can button up all the way and pull your skirt back down if you like though I know you're in too slutty a mood to do that.

4. Come back and sit erect in your chair, no slouching."

I got the response I expected - "ARSEHOLE".

She spent her 20 minutes preparing. Pretty sure she masturbated to get herself back in control, brought her long hair forward to hide her semi erect nipples, buttoning her shirt all the way up and pulling her skirt back all the way down. She walked back slowly with a careful gait and discretely and with as much disdain as she could, dumped her underwear in my lap which I neatly pocketed.

We spoke for the next 20 minutes where I passed over a quickly scribbled poem for her, (those always work), kept eye contact firmly with her erect nipples as I reminded her that everyone in the cafe saw her tits jiggle on the way here, that we could all see her erect nipples threatening to rip out of her shirt and that she was going to provide ample proof of her sluttiness in the damp patch she was going to leave in her seat. Her nervous smiles and 15 glances at her watch told me I'd had the desired effect. When my watch rang the 20 minute alarm, I slipped my hand along her wet thigh. I didnt need to touch her wet pussy to confirm but I did anyway. I gave her labia a nice squeeze as she tightened her thighs around my hand, gave a soft sigh and closed her lust filled eyes. I pulled my hand back, licked my fingers clean of her juices and called for the bill.

She pulled her hair back, her nipples standing up at full mast, my hands around her waist, as we walked out to the valet. She stood in front of me, my fully erect dick grinding slowly against her cute butt as we waited for the valet to bring her car around. 20 mins later, she was fully naked in the back seat, parked in a secluded corner, riding my dick as I sucked a nipple, squeezed her butt and we both grunted in ecstasy as we orgasmed together.