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Crossing the Line by MercianKnight

Fantasy MMF tale of how cyber buddies become cyber buddies with benfits.

Here’s a little fantasy tale inspired by the ever delightful and witty “Ali2teaseU”. Thanks Ali, not least for the honour of being able to use your pseudonym as one of my main characters.




How the blazes did I end up here? I haven’t been to a Night Club in years and, even though it’s an ‘80’s Night, things have really changed. I admit I’m a fairly well presented guy in his mid-40’s but I’ve already had two, sexy as hell, 20-something babes hit on me, and after I passed up on them a bloody guy tried to chat me up. I should be home, with my wife and kid, not on some clandestine rendezvous with some woman I’ve been exchanging e-mails with and never met.


It started innocently enough, as it always does I suppose. She used the online name of “MissTerry” – cute. We chatted, exchanged anecdotes and, when the time felt right, we flirted. Soon we found out we had a lot in common. We were both married, both in our 40’s, me about 5 years her senior, both in loving, married relationships, but both looking for something extra. A spark. Excitement. Adventure.


Anyway, I couldn’t help but feel she was driving the ‘relationship’ so it came as no surprise when she finally suggested we meet, however, it did surprise me when she said she wanted me to also meet with her husband!! I stalled. I had to. I’d never gone this far before, what if he or they were psychos? But, after an e-mailed request from the husband, James, for a chat, I agreed to meet with him. Alone. That was last week, and now, here I am, sat in a booth, in a Night Club, waiting to finally meet James’ wife, Alissa, aka “MissTerry”.


Let me just say that James turned out to be an okay guy. About my height, at 6 foot, and what you would call a distinguished appearance for a guy that must have been about 15 years my senior. He warned me that his wife of more than 20 years was a strong character whom he loved very much and for whom he would do anything for. I had a lot of respect for a man who was frank in his admission that he could no longer ‘keep up’ with his wife’s sexual needs, however, she did not want to be unfaithful to him and had limited her ‘infidelities’ to online liaisons – until now. Apparently, something about me had made them decide to cross the line.


So, here I am, waiting.


When I had met with James last week he had been very candid. Tonight was going to be about satisfying Alissa. Giving her enough of an experience to fuel both of their fantasies for quite some time. This was to be a one off, maybe, and the ground rules were clearly laid out. He showed me a picture of Alissa but it honestly did not do justice to the vision that walked into the Night Club draped over James’ arm.


She is stunning. Okay, physically, her appearance meets all my expectations. About 5 foot 4 inches tall after factoring in those 3 inch stilettos, slim and curvy in the right places with what look like very pert 36B or C breasts (I’m a guy, I can never really tell). Her long, blonde straight hair hangs loose, ending just below the neck line of her form fitting ‘little black dress’, which itself ends about 3 inches above the knees of her so shapely, stocking clad legs. She has an awesome smile on her slightly oval face as she scans the room striding alongside James. Just the way she seems so self assured, so confident in her sexuality is turning me on. Not only has she managed to turn most of the guys heads in the club, I am sure I see envy crossing the faces of several other women, 15 to 20 years her junior. God, she’s hot.


We greet each other, James taking my right hand in both of his in an affectionate hand-shake and also as a ruse to slip a gift, a little blue pill, into my hand. He tells me not to be offended and to think of it merely as ‘insurance’. I can only smile – two firsts in one night? The formalities over with we settle down in our booth to get to know each other. They are a great couple and their personalities compliment each other perfectly. She sits between her “two men” and I’m already starting to relax and think of what the night may have to offer as she takes the initiative and gently runs her hand all the way up   and down the pant leg of my inner thigh. I couldn’t stop getting a hard on if I tried.


It’s not too loud in the Club for us and whilst we may look out of place compared to the majority of the patrons, we certainly don’t feel out of place. Alissa, or Ali as she prefers to be called, asks me to dance. Hell, I don’t even dance with my own wife, but tonight I’m game for anything. We even, finally, manage to persuade James to join us on the dance floor for some pretty raunchy bumping ‘n’ grinding and, despite the exertions, Ali makes it quite clear that my raging hard-on for her has not gone unnoticed. I’m grateful that, when James suggests we make it an early night and retire to their Hotel room, Ali’s face lights up in agreement.


Ali decides we’ll take their car, it’s about a 10 minute drive from the Club and James will drive. She takes me by the hand and leads me into the back of their car. She’s on fire. We latch onto each other almost as soon as we sit down, all inhibitions gone. We kiss deeply and passionately. Her mouth tastes so good. I’ve already decided that I’m going to eat her pussy to orgasm whether she wants to or not and I feel James’ eyes on us as we pull out of the Club car park.


I love the feel of her legs as my hands confirm how supple and toned she is. As I move my right hand up under the hem of her dress, to caress her shapely ass, she tenses up, oh so briefly, then resumes her own exploration of my body. I catch her stealing lustful and furtive glances at her husband who watches us as intently as he can via the rear view mirror as he drives. He has better self control than I do, that’s for sure. James is nodding appreciatively when, unexpectedly, he says “Suck his cock, Ali. Let me see what a slut you can be”.


Ali obliges by quickly pulling out my rigid member and covering it with her beautiful mouth and expertly working it in a way that I have not experienced, I regret to say, in a good many years. With perfect pressure and long, slow and deep sucking, she has me on the edge in no time. Damn, I guess I could blame the anticipation, but the truth is I cum in a matter of minutes because her mouth feels so damn good. I’m so caught up in the moment of my own orgasm that I fail to appreciate how deftly she swallows every last drop of my jism. I’m not even offended as James good-naturedly teases me for cumming so quickly – clever bugger, that’s why he gave me the gift earlier.


I’m now on a mission to prove myself to Ali.


James parks the car toward the rear of the Hotel car park, although heavily shrouded in shadows cast by the security lights, the intensity in James’ eyes is evident as he gives me a knowing nod when we step out of the car.


I take her by the arm, spin her around and bend her over the bonnet of the car, forcing her to try to support herself with her out-stretched arms. Gently, but firmly, I hold her in place as I use my right hand to lift the hem of her dress over that firm ass and then use my own legs to make her spread her stocking clad legs. Ali’s body tenses and I hear her gasp as I probe her wetness with my invading fingers. Panties pulled aside, my still erect, twitching cock gets the nod from James and I plough into her furrow. James gives an appreciative smile as he sees Ali’s reaction to the unexpected, near public fucking. I confess, there is little finesse on display here. All I can think of are the weeks of sexual innuendo, flirting and near-cyber sex as I ram my throbbing cock into Ali’s dripping wet, tight cunt. The vision of this woman spread over the car consumes me. I can feel my cock swell inside her and hear her moans of passion and lust as I deliberately fuck her so hard I lift her up on to her toes just so that I can admire the shape of her legs even as her high stiletto heels are lifted off the ground. I know she is trying to delay her orgasm, to prolong the feeling, but the whole episode of public sex with a near stranger whilst hubby goads us on is too much.

Oh Fuck, oh fuck, she looks so fucking incredible when she comes.

Still panting we look to James............

I never noticed when he took his cock out and began stroking it while watching us fuck. He steps behind Ali, who has not had time to recover herself yet, and shoves himself into her wet, cum filled pussy and begins to fuck her harder than he has ever fucked her. He calls her names, telling her what a nasty little slut she is. It obviously has an effect as his thrusts and words bring her closer to a second orgasm.


“Suck his cock clean, you whore,” he commands Ali, and she duly obeys, reaching out for my still hard cock and guiding it into her sweet mouth, tasting our mix of my cum and her own pussy juices. She manages to get my cock even harder and James, now lost in the moment, says “Fuck her whore mouth”. I gladly oblige.


Ali is visibly convulsing from the sheer ecstasy of being fucked in her pussy and mouth while bent over a car. The face shows the lustful anticipation in knowing that we are both about to fill her with even more cum....


The sight of her being spit roasted is too much for James and I. Ali’s lips work their magic on my cock as I behold the spectacle of James’ animalistic thrusts into her already swollen pussy. Ali looks fantastic. I see the change in James’ face, he's going to explode in her. I want to time it just right. His words are mere grunts now, so I take over from where he left off and tell Ali “Swallow all my cum you cock hungry whore!!!”

And then it happens. All three of us erupting into a paganistic orgasm, simultaneously.

There are grins all round as we regain our composure. Ali pulls her dress hem back down over those delicious thighs and, swinging that tight ass, with hubby in tow, over toward me, she says, "Can't wait to see our room".

In the Hotel Lobby, James gives us the key to the room and sends us upstairs. He'll join us shortly.

I cannot help but wonder if anyone else notices how Ali reeks of sex as we walk to the elevator. Once inside I cannot keep my hands off her. I fumble for her, as yet unseen, breasts, pulling fdown the top of her dress, taking them out to examine the sensitivity of her nipples. I immediately begin kissing and licking around her aureola and hear her moans of pleasure. I do not even bother to cover her up as we scurry from the elevator to the room.


My hands are all over her, caressing her stocking-clad thighs, massaging that tight ass and all the while alternating my lips and tongue between her tits and her lips. Panting, she pushes me away, reminding me we need to wait for hubby and that we have all night.

James arrives, a sly grin across his face. It is decided that we should all freshen up. A quick shower for the guys and a more luxurious bath for Ali. Room service provides us with Champagne and, in a clichéd sense, strawberries.


James and I discuss how things should progress further whilst waiting for Ali. He confides in me that he has always wanted to engage in anal sex with Ali, however, it is the one thing she had always resisted. Apparently, a former boyfriend, years ago, had really messed up her first time doing anal. I empathize and share my theory on how best to help Ali eliciting a broad smile from my new found friend.

Anticipation builds again. Both James and I share a love for women in lingerie, so it is an absolute delight to learn that Ali will be making her grand entrance from the bathroom, not only clean, but in a change of attire. Wearing a red & black lace basque holding up black stockings and wearing black patent leather come-fuck-me heels, she strides out of the bathroom. She looks at James and I, already hard and with a conspiratorial look about us.

James tells her how much he loves her and that tonight he will take care of her and be in charge to ensure she gets everything that she needs. This is obviously unusual and you can almost feel Ali’s heart skip a beat as she walks to the out-stretched arms of her lovers for the evening.....

We lay Ali on the bed and James then retires to the armchair. He wants to watch me explore his wife. I take my time, grateful to have her to myself again. From her ears all the way down to her delicate ankles I take the time to caress and kiss her body. Ali responds deliciously and her pussy soon becomes incredibly wet. It is a pleasure to feel her writhe beneath my ministrations as I finally get the chance to plunge my tongue deep into that sweet smelling pussy.

It doesn't take long, but I can feel her begin to let it all go... she is close. And then, a hand on my shoulder. Panting, she looks questioningly at both of us.
I lay on the bed, cock in hand, and motion her to suck on me. Ali climbs up on me and also offers herself, doggy-style, to James. He accepts the offering and guides his engorged member into the slick, dripping folds of her pussy. She sighs at the pleasure of being filled again and he begins to fuck her with long, slow deliberate thrusts, putting and then keeping Ali on the edge. Enjoying the vision presented James fights to control his urge to pick up the pace. He has a plan.

Ali really does suck cock so well and her whole body is enjoying the sensation of having two willing cocks at her disposal. Suddenly, she feels a well lubricated intrusion at her tight butt hole. Ali tenses up, afraid, but the sensation is not like before and, coupled with the steady thrusts of James’ cock, it's almost pleasurable. She allows the pleasures of the moment to carry her.

A second digit slips into her butt. Ali’s questioning look wonders why is James doing this? He knows how Ali feels about anal sex. But still she sucks my cock, still enjoying James’ cock and I see her relax.

Impossibly, Ali feels so full with a third finger now helping stretch her anal passage. Gently, well lubricated, this is not like before. But it's dirty, isn't it? The feeling is so, well, indescribable for Ali because she has never let this happen before. Ali looks into my knowing eyes, she cannot resist the tide of pleasure she feels.

Suddenly, the feeling of being both filled and stretched is gone. I guide Ali by her shoulders up onto me. We kiss, passionately. She quickly mounts my cock, eager to be filled again. A glance behind her shows James lubing his cock, a mixture of deep love and unbridled passion on his face.

Ali rides me, slowly, grinding her hips down to take in my entire length, enjoying the sensation, knowing, but not believing, what is about to happen. Will it hurt? On this night, of all nights, she wants to know. She has always wanted to know.

James climbs up behind Ali and she feels the head of his throbbing cock slowly force its way into her well lubricated and already stretched ass. A moment of discomfort and then he's in. Two men, both fucking her at the same time in a gentle rhythm that sends her into a world bordering on exquisite pain and pure ecstasy. Her face says it all, her eyes rolling upwards, a deep guttural sigh of pure ecstasy coming from her mouth.

Ali feels so full, so fulfilled so fucking turned on that she barely hears the words being whispered into her ear by your husband. "Oh you fucking whore, how I've always wanted to know what this felt like. I never knew what a complete slut you could be until tonight and I love you for it".

And that is all it takes. Ali cannot remember ever having had such a crashing multi-orgasmic experience EVER. Her thrashing, the contractions of her pussy and ass were much for James and I as we unloaded was little cum we had left deep into her welcoming holes.

Why did she wait so long before crossing the line?

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

Copyright © Copyright ©2009 MercianKnight as registered @ . All Rights Reserved.

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