Coulda, Shoulda

At various times, when we were much younger, my wife and I sometimes talked and fantasized about other men fucking her. It always was and has been a bigger fantasy for me than for her but, at the time, talking about it definitely got her hot. We were leaning heavily in favor of her fooling around with my best friend, Oscar, although a co-worker of mine at the time, Scottie, was pretty much neck and neck with him. In fact, Lisa admitted to me, years later, that had Scottie made a move on her, she would've been very tempted to cheat on me with him. But, for whatever reasons, Oscar was the lucky guy.

Our first attempt was a bust when my wife chickened out but the atmosphere felt different to Oscar. So, while I was out walking the dog, waiting for her to seduce him, she did confess our intentions to him. Later that night while we were fooling around she called Oscar and they had some hot phone sex. I really couldn't hear any of what Oscar said but it was clear, at one point, that he had confessed to Lisa that no girl had ever managed to made him cum with her mouth. Lisa's response was that she wanted to be the first to make him do so. I had no doubt that she could do it and the thought of her swallowing my best friend's cum made my cock throb.

When an opportunity next came along we went for it. It was super hot and I, to this day, still remember specific moments about that night. But I also have regrets that it wasn't nearly as hot as it coulda/ shoulda have been due to my getting jealous at some point and, in the process, rushing Lisa along so that Oscar would leave and I could fuck her. In fact, Lisa later informed me that, should the opportunity ever arise again, she would want to fuck him by herself so she wouldn't feel "inhibited". The various scenarios of just how that might go have played out in my head many times but, as for that actual night, this is is the story of how it coulda/ shoulda have gone.

Coulda, Shoulda

We stopped at a pay phone and I called my wife, Lisa, to give her a heads up that my best friend, Oscar, and I would be home soon. We had been out to shoot some pool and get something to eat, after which, we smoked a joint on our way back to the apartment. I asked what she was doing.She told me that she was playing with herself. I told her I had a better idea and wondered, aloud, if this might be the night that she'd like to actually to go through with it and fuck Oscar.

"Definitely" she replied.

Now, I could say that Oscar had no idea at all as to what was waiting for him when we got back to the apartment but, in fact, we had come very close to doing it on another occasion but Lisa had been unwilling to pull the trigger that night. However, in the process of chickening out, she had confided to Oscar what the intended plan had been and later that night, while we were fucking, she called up Oscar and they had some hot phone sex while I listened in and ate her very wet pussy. For all I knew Oscar might have hoped, since that missed opportunity, that every time he came over to visit or we went to his place, that night might be the night he would get to do all the things Lisa had talked about.

When we walked into the apartment Lisa was nowhere to be seen. With a heart that was, quite honestly, pounding in anticipation of what might be about to go down I walked down the hallway that led to our bedroom and walked in to find her adjusting the lingerie she had donned in anticipation. She was very clearly high as were both Oscar and I, having smoked that fat joint on our way home. After a brief discussion, during which she hungrily kissed me and informed me that she had taken a lude immediately after hanging up the phone, the decision was made. What I most remember about those few moments was the sight of my beautiful wife, on her knees in front of me, sucking my absolutely rigid cock and asking me if I thought Oscar would think she was hot. Silly girl.

The question was how to make it happen. We really had not pre-planned this. Knowing that Lisa was probably feeling nervous and, possibly, self conscious, I suggested that I go into the bathroom and shut the door. She would utilize that time alone to seduce Oscar and get things rolling before I joined them. I stood there with my ear to the door. A short time later I could clearly hear them come down the the hall and into the bedroom just across the way but couldn't make out anything they might have been saying. I decided to take my time until I recognized what were clearly moans, at which point I turned out the bathroom lights, quietly opened the door and stepped the few feet across the hallway to the bedroom doorway. Peeking in un-noticed, I found them standing next to the bed, still clothed, kissing. I heard Lisa ask him whether he was nervous. He ignored her question and, as if in answer, he slipped a hand into her skimpy panties and was clearly fingering her cunt.

I stepped back just out of the doorway, still listening,and heard Lisa say to him "Take off your clothes and lie down on the bed. I wanna suck your cock!" At that point I got naked and quietly walked into the bedroom. Oscar was lying on the side of the bed closest to the door, his hard cock standing at attention. Lisa was on the bed kneeling between his spread legs.

She immediately engulfed his rock hard cock in her mouth. The lights were low so I couldn't see anything with real clarity or detail but the exposed portions of his cock, as Lisa's head bobbed up and down, were clearly wet and I watched her release him from her mouth and stroke the hard flesh, his cock sliding between her fingers as she did.

By now I was kneeling next to the bed, not a foot away, tranfixed by the visual image of what I had long fantasized about; my beautiful wife with another man's cock in her mouth and hands. I could hear the wetness of her mouth as she sucked him. She seemed, I thought, mesmerized by the reality of my very best friend's cock right there in front of her when she suddenly looked up and met my gaze. She smiled a wicked smile and, cradling his cock in the palm of her hand, rubbed the entirety of it across her face and lips, looking me in the eyes as she did. She then reached out to place her hand on the back of my neck and pulled me in for one of her hottest kisses ever. Ever.

I fancied that I could taste the musk of my best buddy's dick on her tongue and in the copious amounts of saliva that my tongue was slipping around in within the confines of the furnace that was her mouth. Had she, at that moment, proffered me his cock I might have been tempted to take it into my mouth, being so high and so caught up in the moment. But in the back of my mind I was picturing Lisa, her mouth full of his cock as he came in my wife's hot, willing mouth and I knew that I would probably take some sort of perverse pride in the fact that my young, beautiful, hot wife was the first woman to ever swallow Oscar's seed, knowing that would be a moment he would never forget.

At that moment he gently interrupted her, pulled her up close to him and kissed her. As he did she kept a grip on his cock, stroking it a bit before reaching down a little further to touch his balls. His, and her, intentions were clear at that point and I watched as she straddled him, reached back between her legs and guided him into the hot, wet confines of her hungry pussy. I imagined in my head what each of them might be feeling at that moment and I moved onto the bed, kneeling next to them. I stroked my wife's back and ass, a faint sheen of sweat making her body glow already in the dim light. She leaned down to kiss him while he wrapped his arms around her waist. Then he slowly let his hands trail downwards across the small of her back and onto the cheeks of her ass. He slowly, almost imperceptibly, began to spread them until her rear end was splayed and I could see the wrinkled little starfish of her anus.

At this point Lisa was more or less grinding on him and telling him, in a voice loud enough for me to hear, just how long she'd been waiting for this to happen. She then whispered something in his ear and I could imagine how the dampness and heat of her mouth must've felt against his ear. Quite suddenly he raised his right hand only to bring it solidly down upon the pale, alabaster flesh of her buttocks. She cried out but remained still while he rained a flurry of blows to her backside and I could very clearly see the outlines of his hand prints tattooed on her flesh. She suddenly sat up astride him and maneuvered herself so that she was squatting rather than sitting on his cock. She reached down to support herself, her hands braced against his chest, and began to tremble and buck and use the weight of her body to drive.

"Stand up Baby!" she ordered and I did, my hard dick bobbing and weaving in her face. She maneuvered me around so that I was standing in front of her, my feet on either side of Oscar's body, and I steadied myself by holding onto the ceiling fan directly over my head. Placing her hands on the cheeks of my ass, she pulled me in close and took my cock into her mouth. She looked up into my eyes as she did before releasing my rampant tool from the wet confines of her mouth.

"Does my mouth feel good on your cock Baby?" she asked as she rubbed it back and forth across her face and dug into my piss hole with her tongue.

I enthusiastically answered in the affirmative and leaned over to kiss her.

"Are you my slut?" I asked.

"Mmmm Hmmmm!" she answered, her voice cadenced in a way that never failed to heighten my arousal.

"Is Oscar fucking you good?"

"Oh yes!"

She started to rock on her heels then, back and forth, faster and faster until she slipped over the edge and came, a veritable torrent of cunt juice squirting over Oscar's dick and belly, matting the hair on his body and I found myself briefly wondering whether his hairy body, so different from my own smooth skin fueled her excitement in any way.

Oscar was now sitting almost upright, one arm wrapped around her to support him, one hand palming and rubbing a hard nipple while he almost frantically nursed from the other. Her hand wrapped around his head pulling him even tighter against her as she continue grinding on him. She came once more, the unseen force of it racking her body. After a minute or so she gave a little shudder, let out a satisfactory sigh and steeled herself for the next round.

She lifted herself off of his cock and laid back towards that side of the bed, positioning herself so that her head hung back over the edge. She grabbed Oscar's hand and pulled him between her legs, simultaneously splaying them and hauling them back and put her wet, abused cunt on display in the process. She reached down and used two or three fingers to aggressively massage her clit while she looked up at Oscar.

"You fuck me so good Baby." she cooed, looking up at him as she continued to work her clit. Clearly she wanted some more of that "good fucking" and he obliged her. Leaning over her on one arm, he reached down with the other, grasped his cock and fitted it into her before driving his hips forward and burying it in my wife's cunt.

Lisa then lowered her legs and wrapped them around Oscar's waist. She hooked her ankles together, in effect "trapping" him in a place I'm sure he wasn't in any hurry to leave. I had already moved to the side of the bed. Her head hanging upside down, she briefly lifted it, looked up at me and stuck out her tongue as if to say "Feed me!" My hot, sexy young bride was very high, very horny and fully invested in the moment. Needless to say, I fed her my cock while my best friend fucked her. Hard.

After yet another climax she gently placed her hand on his chest and pushed him off of her, telling him to lie down. She crawled between his legs and took his glistening cock deep into her mouth, a satisfactory groan emanating from each of their throats as she did. I'd have bet serious money that that her groans of pleasure and lust had as much to do the taste of her own pussy as it did with the cock I watched her head bob up and down on. She proceeded to nurse on his rigid flesh and stoke his balls in a manner that would have had me spilling my load.

She released her mouth from his cock and started to crawl up his body so that she could straddle him, just as she had straddled him at the beginning of this little adventure. As she reached back between her legs and grasped his cock she turned her head to look at me and uttered one word.

"Vaseline.

She lowered herself onto him as I walked out the bedroom door and across the hall to the bathroom where I retrieved the requested jar from underneath the sink. I also reached into the linen closet and grabbed a couple of towels. When I returned I was treated to the sight of her lying on Oscar's chest, making out with him. When she realized I was standing there she reached her arms back, grasped a cheek in each hand and pulled them apart as far as she could, showing me the dark pucker of her anus.

I climbed onto the bed and knelt behind her, Oscar's legs splayed to either side of me. When she sensed that I was where I needed to be she removed her hands from her ass and used them to support her upper body and leaned slightly forward so that she could feed her titties into his mouth. Oscar definitely appreciated them I thought to myself. No doubt they were very different from his girlfriend, Jodie's, smaller, much less impressive breasts.

Lisa, her cunt red and swollen, was grinding slowly on my friend's cock. I leaned forward, spread her cheeks as she had done earlier and dragged the very flat of my tongue, slowly, from the bottom of her taint to the top of her wrinkled little shit hole. In the process I bumped Oscar's cock with my chin and, surprisingly, felt my cock twitch from the unexpected contact. I spent the next few minutes digging my tongue as deep as possible into her rectum before eventually transitioning to my fingers, the tips of which were slick with copius amounts of vaseline. By the end of my "chore" I was working the first two fingers of each hand deep into that hot, humid tunnel, and actually prying her anus open.

While all of this was happening she related to Oscar exactly what I was doing to her and told him how much she loved getting fucked in her shit hole. Eventually, as my fingers slipped from inside her, she sat up and turned to kiss me deep and hard and told me what a good job I had done getting her ready. She leaned forward and lifted up a bit so that Oscar's hard cocked slipped from her cunt and slapped wetly across his lower abdomen. I scooped more vaseline onto my fingers and grasped his cock but not before I spontaneously leaned over and took it into my mouth. I heard Oscar groan in shock. In surprise. In lust. Lisa noticed his reaction and turned back, as best she could, so that she could see what I was doing.

"Oh Baby, that's so hot!" she exclaimed as she placed one of her hands on top of my head and gently, but insistently, forced my head further and further down until my nose was buried in the thatch of his dark hair and his cock was, for just a second or two, buried in my throat. I diligently cleaned the rest of Lisa's cunt juice from his rod and sucked his nut sack into my mouth as well before resuming the task at hand.

Not having touched a cock since my adolecence, I took advantage of the opportunity to grip and stroke a grown man's cock. Within a few seconds Oscar was, as best he could, lifting his hips and fucking his cock through my greasy fingers. Once he was sufficiently lubricated I sprawled across the empty side of the bed and wiped my hands clean with one of the towels I had grabbed earlier.

Lisa lifted herself off of Oscar only to scoot over and straddle me. It occurred to me that this was the first time my cock had been in her cunt all night. A fact that heightened my sense of anticipation as she slung her leg over me and slipped my cock into her cunt. Though Oscar's cock was similar in size to mine it felt to me like she had been fucking one much thicker and I immediately understood that it was because of the epic fucking he had been giving her. She leaned over and kissed me hungrily, then looked in my eyes and, with a subtle smile on her face, whispered "You're welcome."

Oscar, by that time, had figured out the score and had moved so that he was kneeling right behind Lisa. His arousal was written all over his face and his hands wandered, almost unbelievingly over her body. She leaned back into him and gave him a hot, sexy kiss.

"Am I a hot fuck?" she asked, almost in a whisper.

"Oh my God. Yes."

"Have you always wanted to fuck me?" she pressed. "I bet you have. I've always wanted to fuck you." she said.

"You're right. Always!"

"Does my ass turn you on? I mean have you ever thought about fucking it?"

"Definitely!" he answered.

"Are you gonna fuck it good? 'Cause I definitely want you to abuse it." Her query sounded, suspiciously, like a challenge.

"What do you think?" he asked as he ground his cock into the slippery crevice of her bottom.

"Then fuck it." she said as she leaned forward, braced her arms on either side of my head and, so far as I knew, for the first time, offered up her most intimate orifice to another man. Lisa closed her eyes. She clearly enjoyed the anticipation as he spread her cheeks wide. As he did, I saw him very slightly, almost imperceptibly, shake his head, in apparent disbelief at the good fortune being visited upon him. With one hand he stroked and caressed the globes of her ass cheeks and the small of her back. He reached down with other, took his glass hard erection in hand and rubbed and lightly pressed it against Lisa's greasy pucker. I tried to commit it all to memory; the sensation of all our legs, both hairy and smooth, brushing against each other in various places. The weight of his cum filled ball sack coming to rest against the base of my cock as he positioned his self closer to my wife's luscious ass.

I think I almost lost it when I felt the head of his cock breach her opening. Through the thin membrane between the depths of her cunt and her soon to be ravaged bowels I could feel the head of his cock tap and lightly nudge the base of my own as he paused for a moment before resuming his invasion. I half expected to hear Lisa tell him to go slow or say "Easy", the way she would do with me on the rare occasion that she caved and granted me entrance into her "forbidden" hole. In stead she pushed back and impaled on the last few inches of his dick. Years later, I would learn that the cocks of most of the other men she had fucked were quite familiar with the insides of her bowels and that revelation, though it shouldn't have, turned me on immensely. Knowing how sexy and hot she looked when she was writhing on a hard dick, I couldn't help but picture her in my head being the cock worshiping, anal slut that she evidently had been.

As Lisa pushed back against him he I could feel the entire length of his cock slide along mine as he fully entered her slut ass. As aroused as I was and as wet as she was, even in the depths of her cunt, it felt almost as if there was nothing separating our cocks. Intellectually, I understood that there was a barrier, thin though it might be, between our cocks now feverishly rubbing and grinding against each. This wasn't, in the least, intellectual and I found the reality and intimacy of it to be mind blowing.

Neophytes that we were, it took some time to find a mutually satisfactory rhythm and position to fuck in. In the beginning, as if in some unspoken arrangement between the three of us, we simply remained still and, I imagine, concentrated on the sensation of where we had come. I could feel the pulsing of Oscar's cock against the involuntary contractions of mine. As if on cue,as if she were reading my mind, Lisa's eyes closed and, with a rapturous look on her face, she quietly said "Fuck! I can feel your cocks throbbing inside me!