Close to The Real Thing

I'd been trying to get with Stacey for many years. For various reasons, there always seemed to be one or more roadblocks. Either she was in a relationship, or I was, or one of us had travelled to far away places. Regardless of the reasons it had only served to heighten my desires. At present, neither of us were in committed relationships. Distance was not currently an impediment and to my way of thinking, the timing should be perfect.

Our friendship went back to the beginning of college when we first met. At the time, I was casually dating a woman who lived in the same residence as Stacey. The three of us played on an intramural volleyball team together which meant that Tuesday nights ended at the campus pub. Unfortunately, Stacey and my then-date had become quite close. Though my relationship with her friend had fizzled over the semester and I was technically available, some 'girl code' meant that I was effectively off-limits to Stacey despite us both being otherwise free to tangle. All of this despite a mutual attraction and enough flirting to make me feel as though the two of us could make some great fireworks together.

As the years passed, Stacey and I kept in touch. When in the same city we would make a point to go out for lunch or drinks at a pub. All the while, we also maintained a sporadic online connection which had progressed to sexting which quite often led to incredible mutual masturbation sessions on video calls. Even still, and despite a now unquenchable desire to have her in the flesh, I just couldn't seem to find the timing or the situation to 'close the deal'. What made this particularly frustrating is that my most recent move up the corporate ladder found me residing in Stacey's hometown where she had long ago returned to start her career.

It had come to the point where I was determined to confront Stacey with my true desires. It started while texting one lonely late Thursday night. Stacey wasn't currently in a committed relationship and had repeatedly described the frustrations of being constantly wet and horny without an on demand cock that was ever-present to satisfy her needs. This was typical of our level of sharing. Over the years, our trust in one another had led to sharing and disclosing our every fantasy and desire as well as the most intimate of details about our respective sexual conquests. It had become quite routine to find each of us texting the other after the latest sexual conquest and sharing a play-by-play of the action for the other's vicarious pleasure.

When Stacey's 'video request' popped up on the screen that night I was immediately piqued at the possibilities. I had texted her earlier and knew that she was meeting a friend for a pint of beer. I wondered if she was about to describe her latest sexual escapade to fuel my masturbatory thoughts or perhaps it would just be another 'silent session' as we often enjoyed. No sound, no talking or requests -- just a shared visual as we pleasured ourselves while watching the other. The easy move would have been to go with the flow and guarantee a fantastic wank to close out the night. It was tempting to add yet another session to the memory banks but I had reached a point that I felt it was time to make my pitch for a real hook-up even if it scuttled the night's sure to be, mutual orgasm fest.

It wasn't a hard 'no' in the traditional sense but it certainly wasn't a yes either. Stacey confirmed the sexual tension between us and the mutual attraction that should normally lead to a real life, in the flesh hookup. The two of us had literally spent years flirting and talking about being together sometime. But from Stacey's perspective, it was the many close years between us that made her less willing to try it for real.

"Listen, you know I'm incredibly attracted to you and I have no doubt that we could be fantastic together. I've thought about it just as much as you have. We have a great deal in common and have come to know each others' kinks and desires in a way that most couples will never realize. Whenever we have played online, I've had some of the best orgasms of my life. And, as you probably can imagine, you have been my 'goto' inspiration whenever I need a good solo moment with a guaranteed body-shaking orgasm."

I listened to all this and just couldn't figure out how it was not leading to an invitation to head over to her place and fuck each other to exhaustion. We had seen every inch of each other's bodies. We knew the most intimate details about each others' fantasies and sexual experiences. Stacey had confirmed the mutuality of our sexual interest and desire and yet she still seemed to be heading toward 'no'.

"It's not that I don't want to and certainly not that I haven't fantasized about it with my fingers or toys at least once a week since that first time we met. But that's just the point. Over the years we have each had dates and lovers who have come and gone. We have been the constant for each other and no matter the strength of my desire to try it for real, I couldn't stand to lose the very strong connection we do have. I've thought about it in such detail that I sometimes wake up in the morning and wonder if it really happened. My worry is that I've built it up to be so big that actually following through would have to be a let-down regardless of whether it turned out to be the best sex I have ever had. More precious to me, is the fantasy connection we have and no matter what else changes in life I couldn't bear the thought of not having my relationship to you as it has always been."

That I agreed with or at least understood Stacey's logic did little to quench my thirst for consummating our relationship. A younger version of myself might not have given up so easily but I too, very much valued the odd relationship we did have. If preserving it meant being denied the real thing, then I would just have to make do and enjoy the benefits that were far too precious to throw away even for a great fuck. Stacey could obviously sense my emotions and was quick to add in that it was worth future discussions.

As I looked back to the screen I noticed that Stacey was now completely naked. No matter how many times I have viewed her sexual body it never got tired. I had memorized the curve of her small breasts and the perky nipples that always stood proud and erect. She was laying back with her smoothly shaved lips now full and open. Her clitoris was noticeably rigid and the small triangle of tawny curls looked neatly trimmed as usual.

"Lets see if a bit of play will put some cheer into our conversation!"

Her 'no' was obviously a disappointment but not one that could soften my erection. As Stacey's camera panned out for a wider view I was able to see the context of her new woodworking project. She had refinished a traditional cedar chest that lived at the foot of her bed. Inside, were the many toys and objects I had given to her and others she had collected or been gifted over the years. Just seeing her immense collection of private play things caused my balls to contract. Precum had already begun to leak down my shaft and I had yet to even touch myself.

"Why don't you pick how I pleasure myself tonight and I will share whatever story will get you off?"

I suggested the ribbed glass dildo which I knew to be one of Stacey's favorites and for my own titillation asked that she insert the medium sized tapered plug into her asshole. In terms of stories, I suggested this evening's, hoping that she got laid and perhaps I would glimpse the creampied remnants of her latest romp. She knew this to be one of my darker fantasies but had yet to let me witness her in that condition.

Stacey placed the phonecam on her bed and turned to kneel and bend at the waist. In the most teasing fashion, I watched as the narrow end of the plug just barely toyed at her entrance. She moved the toy down between the lips of her cunt for some natural lube. Slowly, I watched as the pointed end pierced her rear opening and ever so gently started to sink deep inside her. Stacey's ass opened to this familiar invasion and stretched around the increasing width of the toy until popping firmly in place around the bulbous base of the toy.

"I didn't get laid tonight so we may need to finish with one of my older familiar experiences but let me begin with what did happen and I'll finish you off with my plans for this weekend which will certainly get you there! But don't you dare cum until you hear the special ending."

I stripped off my boxer shorts and began to slowly stroke my cock knowing that Stacey's stories always made me cum. Usually, the challenge was not to cum too quickly before the story had concluded.

"I've been chatting with a guy named Derek that I met on one of those online dating sites. Still not sure what I think about the whole idea but a girl has to find it somewhere and my dryspell has lingered a bit longer than I could stand so I decided to meet up in person and see where it would go. We had exchanged pictures so it wasn't hard to spot him at the local Irish pub we had chosen."

"Our conversation went well at first and after a few rounds of drinks we were into some furious flirting. I had not necessarily intended that this first meet up would lead to a quick fuck but I honestly had not definitively ruled it out either."

I asked the usual questions like whether the guy's profile had been honest or whether he seemed different in person.

"I'll get to that soon but let me tell you where it was all heading before going off of the rails!"

I continued to stroke while watching Stacey probe the curved glass dildo in and out of her cunt.

"We were sitting in a booth and had moved directly beside each other so we could watch the band while we chatted. The lighting was dark and before long Derek had become much more bold. His hand rested on my knee but quikly moved up my thigh. My recent lack of physical contact had made me far more willing than I normally would be on a first date but I found my thighs spreading slightly to let him know that I didn't object. As his hand cupped my mound I actually moaned which would have been embarrassing if not for the music of the band. As his fingers curled and applied more pressure it was like he knew precisely where my sensitive clit was located. At this point I found it awkward to continue with any meaningful conversation. To any outside observer, I am sure it just looked like the two of us were sitting silently enjoying the band and our drinks."

I was more than keen to find where this was leading but curious about the part of everything going off the rails.

"In another act of boldness that surprised myself, I reciprocated by reaching over and placing my hand directly on his groin. Not surprisingly, I could feel the stiffness of his erection trapped in the left leg of his jeans. Derek didn't say anything when he felt my hand squeeze his denim covered cock but his fingers began to push harder between my folds. This went on for the next two songs and I'd become so wet that I truly worried it would start to show through my pants or worse, cum right there in the bar."

I let Stacey know how hot the story sounded so far and she could see that my stroking had begun to pick up the pace.

"Don't you dare cum yet! You won't believe how wet I actually got - forget what I just said. Run out to your mailbox and come straight back to the phone!"

With both surprise and great anticipation, I did as Stacey directed and found a plain paper bag taped shut at the top with duct tape of all things. Without waiting to open it I returned to the camera to show that I had followed her direction. When she told me to rip it open I was thrilled to find a pair of light pink panties with a crotch that was darkened and still wet to the touch.

"Put my panties up to your face and taste just how wet that bastard got me before telling me that he was married but free tonight! That was a line I wasn't willing to cross so I left him and his sizeable married boner at the bar and went straight to your house. I was actually thinking of knocking to come in when the fun of this idea hit me."

I smelled Stacey's erotic scent (not for the first time), and licked up the wetness that some other guy had helped create and no doubt would have enjoyed had he not turned out to be deceitfully married. As her sexual taste and aroma overwhelmed my senses I stared between her splayed lips and could see that she was still glistening wet.

"I see you like my panties! Hold off and try not to cum while I add just a little more to tonight's story."

It was all I could do to stop the cum from splashing across my tummy but my curiosity won out over my impatience.

"I was obviously disappointed, frustrated, and still horny as fuck. So after dropping off your little surprise, I came home and texted my friend Kevin whom I've told you about before. He lives over an hour away but he's not married and as you are aware, a pretty satisfying fuck for me on the odd times we can meet up."

Stacey had described each of her dalliances with Kevin and I knew all to well that she considered him an accomplished bedmate who never failed to make her cum multiple times whenever they were together.

"Anyway, I called Kevin and told him how much I needed it. Actually, I told him I needed him to come to see me this weekend and fuck the shit out of me. For tonight, you and I will come together and don't worry, I'll let you finish soon enough. I thought about saving the next Kevin experience to share after it was done but tonight I want to try something different. This way, you and I will share in the anticipation of my next great fuckfest."

My hand was now moving with a mind of its own. The excitement of Stacey's words were made so much more powerful by the mystery of what they might mean. We had shared a great deal of fantasies but I wasn't always sure which ones Stacey might like outside of just talking about them. Was she thinking of inviting me to partake? Or perhaps she was finally game to let me simply watch through the crack of the closet door? Both had been fantasy discussions that had made each of us cum countless times before.

"So before you jump to the wrong conclusion my stroking buddy, this is not about a threesome and I still don't think we could pull off hiding you somewhere in a room and not getting caught. But, I do have an idea I think you will like. I'm not willing to secretly record myself getting railed without Kevin's knowledge but I think I can keep you involved if you promise not to cum all weekend until we Facetime Sunday after he leaves."

I nodded without knowing what I would get in return but knowing it would be more than worth having to deprive myself for two solid days -- which I almost never do. Meanwhile, I stared hypnotically at the rhythm of Stacey's index right fingers massaging her clit in a manner I have long since committed to memory. Her left hand worked independently and at varying speed allowing me to imagine it was my cock that was probing her insides.

"At some point early in the weekend I will send a few pics of me stroking and sucking Kevin's cock. Perhaps that will aid in your imagination of my oral skills. Then, as our fuckfest continues, I will find a few moments where I can get a secret pic or two. Maybe when I head for a bathroom break I will let you see his cum splattered on my neck and tits. Perhaps even a throwback hickey on my tit. Maybe a closeup of my pussy after I've been thoroughly fucked. And then, if I'm feeling particularly bold I'll....."

Whatever else Stacey continued to say was completely lost on me as the cum literally erupted from my cock and covering my chest and stomach.

"Well, I'd say that did the trick. Keep your hand off that thing and I'll see you online Sunday night after I've been well and truly fucked hard. Maybe check your mailbox... "