Roleplay with Jenice

I have been friends with Jenice for the better part of a decade. I am a part time poet and Jen has been my muse for the longest time. In all the years we have known each other, we have never been a couple as both of us have never been single at the same time. But it has been a friendship that has stood the test of time and we both treasure each other's company. I do have a somewhat unhealthy obsession for her, which she knows, and to her discredit, encourages. Doesnt help that 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 day! Despite the decade spent masturbating to her thoughts, she feels just as decadent as when we'd first started out.

Jen has a great sense of humour, is tremendously successful, and while she is aware of how good looking she is, is also blissfully unaware of how dangerous a tool her whole body can be. Jen lives close to where I work and will occasionally drop by to meet. She does use a not-so-subtle hint on me when she's in the mood - she knows I love her tits so will show me her irresistible cleavage to tease. Watching me steal glances and be unable to maintain steady eye contact gives her a high! When there is cleavage on display, I read it as a sign of playtime and have my hands wandering all over her, unmindful of whether we're in public or not, although she sometimes lays down a no hands rule. What she doesnt know is that 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. If she did, I'd never be able to tell when she was in the mood and I'd end up groping her every single time!

Today, Jen was returning from a long client meeting and was looking to bounce some of her ideas off me on the way back, so we decided to meet at a coffee shop nearby. Its a typical Starbucks store with a couple of tables in a corner that arent quite as public as others. We rarely choose those though but today we didnt really have a choice since the others were either taken or still dirty from prior guests. One can only assume they were short on hands at the cafè that day. I sat facing the cafe while Jen took the seat facing the wall behind me.

Jen 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 sent a very clear "I AM THE BOSS" message. Definitely not playtime mode, to my utter disappointment! We sat down with our cups and she went on to tell me about her day. Sounded like a typically exhausting day that she filled with an energy that focuses on getting things done her way. I do love hearing about her work and her plans as she talks about it with a passion of someone that loves doing what they do, and when she does, its also a quality that turns me on immensely.

I was too turned on and horny to continue a serious conversation anymore. I started flirting with Jen, complimenting her long hair, her smile, the way she was carrying off her boss lady look...trying to melt her out of her icy-cold business frame of mind. Took a while but finally, a hint of a mischievous smile with a playful reprimand about my blood running to the wrong organ, finally found a way to her lips.

Jen loves talking about her recent crushes and I know it also gets her turned on 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 would have to do what I said and the roles would be reversed with me being the hunter. She'd make the second trip to the washroom on my terms. If I lost, the second trip to the washroom would be mine and I'd have to rub one out myself. We'd each get 20 minutes at our turns at seducing each other. We'd inspect each other to decide if we were successful.

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. It had been a very, very long time since we'd had an erotic episode with each other. I was determined not to lose though, it wasnt every day that Jen agreed to do my bidding, even if the odds 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 she thought 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 a couple of buttons left undone to show the kinda cleavage that she knows can drive me mad. It wasnt so much that you could see a lot of her boobs nor so little that you didnt see the valley. If she bent the right way or leaned with her biceps squeezing her side boob, she could easily show more. She was in complete control. Her skirt on the other hand, was now pulled to half way up her thighs. When she sat and crossed her legs, she could easily show so much more. What. A. Sight.

If she'd put her hand on my shaft, I'd have lost the game right then. She knew it 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 she did her utmost to lean and open up her shirt to show more cleavage and her lacy white bra, it was excruciating! She tried well though and stayed in character referring to me as her new hire and carrying an innuendo filled conversation about work that was sheer genius.

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 anymore. 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 me touching her, getting her to touch herself, or asking her to show more cleavage or leg. I agreed. My plan didnt involve exposing her, at least not in the ways she thought of 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 your shirt 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 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, conscious of her jiggling breasts 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 and very lewd poem for her:

I could say I love you but that would be a lie

For my heart isnt really eating you up with my eyes

Your gorgeous legs on display for me

Every little inch is all that I now can see

I could say you are beautiful but that would be untrue

For your eyes arent what mine are locked on to

Your sumptuous breasts jiggling as you walk

Your nipples poking out, even as we talk

I could say I lust you and that would be the only truth you hear

I'm watching you with the hunger of a tiger for a deer

I am gonna enjoy making you squirm, dear Jenice

Till you finally cum, screaming on my penis

True to the words, I kept eye contact firmly with her erect nipples as I told her I was surprised at how bold she was to let everyone in the cafe see 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, and all this for me! She said I was cheating, not staying in character and that she hated me but she didnt call the game off. 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 she visibly jumped in her seat, squirmed and twisted her face, and shut her eyes as she prepared herself for my touch. I reached over the table with my left hand and held her hand reassuringly, while I slipped my right hand along her wet thigh. She bit her lower lip and lowered her head, mixed in a deadly emotional cocktail of shame and arousal. I didnt need to touch her wet pussy to confirm but I did anyway. I traced my finger along her swollen lips as she tightened her thighs around my hand, gave a soft sigh and opened her lust filled eyes to give me that look of longing. I pulled my hand back, licked my fingers clean of her juices as we locked our eyes and called for the bill.

She pulled her hair back in a ponytail before she got up, a move that put her nipples standing up at full mast on display. She kept eye contact firmly with me and asked me if I enjoyed making a slut out of her. I smiled and assured her we were just getting started. We stood up and walked out to the valet with my hands wrapped around her waist. She stood in front of me, my fully erect dick grinding slowly against her cute butt, hands wrapped around her stomach, our fingers intertwined, as we waited for the valet to bring the car around.

We drove around for a while, my hands massaging her thighs to begin with. She loves a good butt massage though, so I moved my hand under her. She turned to face away from me and gave me better access. I moved her skirt away and spent the next few minutes massaging her firm butt. I'd move my finger intermittently between her cheeks tracing her crack up and down. Her pussy was leaking now and I traced my finger to the line between her ass and her pussy which got her moaning softly.

I slipped my hand away again and fished out her bra and her panties from my pocket. I asked her to move to the backseat and put them on again. I was going to enjoy this fully and I wanted to enjoy stripping her layer by layer myself. She moved back making her way over the armrest giving me a very nice view of her ass! I adjusted the mirror so she was completely in view. She opened her shirt and managed to slip on her bra without putting her gorgeous breasts on display. She then pulled her skirt up as I adjusted the mirror to focus lower and proceeded to caressing her pussy. She pulled her lips apart to show her labia and pulled her fingers away leaving a line of her juices hanging and extending showing me just how horny she was. She said she couldnt wait to have my dick inside her. I told her she'd need to wait and that she had to put on her panties now.

She reluctantly complied giving me a fake pout and then slipped back in to the front seat, locking her lips on to mine as she sat. I pulled up at a chemist to pick up a pack of condoms as we both headed out together, hands entwined for the chemist to know exactly what we were about to do. As we walked back, I slowed and followed her, taking the opportunity to watch her seductive gait as she got to the door and opened it. I sat back in the driver's seat and we drove to a secluded spot.

I moved to the backseat first using the doors, and Jen followed from between the front seats. Our lips locked as we ate each other hungrily. Our tongues teased and played with each other as my hands caressed her silken hair, then moved to her back and made their way to unzip her skirt which she removed up over her head. I kneaded her butt as she pulled out my shirt and deftly unbuttoned a couple so I could remove it. I proceeded to do the same to her and had this amazing and hot little slut, sitting on my lap, kissing me like she meant it.

I laid her down on the seat and moved back to take in the sight of this scantily clad girl with the sexiest smile I knew. I pulled her back in to a kiss, moved to nuzzling her neck as I fumbled with her damned bra. She leant a helping hand as she helped me unhook it. As her bra fell off her shoulders, her gorgeous breasts and perky nipples popped in to view for the first time. I squeezed her boobs and fiddled with her nipples for a while before diving in to take them in my mouth. I spent the next few minutes suckling and fondling them like a baby!

We disengaged again and I got out of my shoes and my pants. I had her leg on my shoulder as I kissed my way down from the back of her knees to the top of her thighs. Her smell was intoxicating and I used my teeth to pull her panties off. I went back to her pussy and licked the periphery trying to tease her and draw this out until she put her hands in my hair and pressed my face into her cunt. I ate her out briefly before she climaxed in a series of shivers and quiet moans. I slowed down and then moved upwards to her stomach and her belly button. She lay there half spent as I pinched her nipples and squeezed her boobs. I flipped her over and went on to massage her shoulders, back and butt.

She turned around again after a while and sat up asking me to lie down instead. She pulled my underwear off and played with my dick between her deft fingers. She doesnt like giving blowjobs much but took my dick in her mouth anyway, giving me a sloppy, noisy one. Once I was fully erect, she moved up to lock lips again as I put on a condom. She guided me in, slowly, with little oohs and ahs as she took me in, inch by inch. Half way in, she took a pause and lay down on me, gyrating her hips slowly. I grabbed her ass and helped the rest of my penis in her with a rather gruff thrust. She let out a scream and bit in to my shoulder. I hoped it wouldnt leave a mark!

We started thrusting in and out, slow at first before picking up pace. I let my hands wander on her arse and my fingers slip between her crack. As she got more excited, she sat up as much as she dared with one hand on my chest and the other half covering one breast while her fingers pinched the other nipple. I slipped one hand to find her clit and started rubbing it with my thumb. I sat up half way and pulled her head back by her hair to arch her backwards and thrust her breasts out. I got up the rest of the way and bit one nipple before whispering "You are such a horny little slut" in her ears which pushed us both over the edge. She let out a throaty moan as I grunted and pumped as much cum as I could in her. We lay in each others arms, exhausted and smiling as we locked our eyes and kissed each other again.

20 mins later, we were back at the cafe, sipping a coffee and having a conversation that would never belie what had just happened between us. We parted an hour later and she leaned in for a friendly hug. I dont think I will ever have enough of her and couldnt help squeeze her butt and whisper

"I love your sexy, needy pussy so much. Cant wait to stuff it again!"