The New Girl Ch. 01

It was strange relationship to be sure. His partner had found her waiting tables in a local restaurant/bar during one of their rare boy's nights out. He was looking for some help in the office, and she professed to have the skills he needed. A recently divorced single mother of two, working a second job, trying to make ends meet. As unlikely as the circumstances were, a deal was eventually struck, and she became part of the team.

He was a senior manager, thinning hair, overweight, irreverent to the extreme, but not outside the accepted norm from a propriety standpoint. In a sterile marriage, the last, he swore, in a string that he was not proud of. Celibacy, the order of the day, was not an option, but neither was any circumstance that would jeopardize the relationship he was in. The odd pickup, hookers, even a regular NSA fuck buddy were possibilities, but discretion was paramount, with never any possibility of a long term relationship developing beyond the sexual.

She was 25 years his junior, slender, attractive, strong, intelligent, independent, perhaps wound a little too tight, but friendly and with a confident air. She was the preeminent soccer mom MILF, devoted to her girls. There was little to indicate anything unusual, other than an occasional comment that telegraphed a somewhat offbeat sense of humor.

It started innocently enough with a stray comment here and there that pushed the bounds, but not necessarily by much. She was still proud of her tits, even though in earlier years they stood prouder and firmer. He commented that she had a cute ass, which she dismissed. It really started with her strange question regarding his porn viewing preferences: Did he prefer MMF or MFF? As strange and out of place as the question appeared to be, he never hesitated in answering, saying that he had previously participated in a MMF three-way. He really wasn't sure why he answered that way. Given their respective positions, he was risking a lot, but testing the waters seemed important. Without hesitating, she confessed that a MMF provided the best of all worlds! OK, life was about to get interesting!

She was a willing participant in the sexual banter, holding little or nothing back. Nor did he hold back, again, in spite of the risks involved. The connection between them was remarkable in its depravity. She described it as a common perversity. He suggested a kindred spirit connection. They were both right. He knew this feeling well, experiencing a missed connection years earlier that he would not let happen again. He knew this would never be more than a sexual relationship, which is about all either needed or could handle at this point in their lives. The friendship that ensued was a surprise, but provided an intense booster to their play.

He knew in his heart, and told her so explicitly, that before it was over he would taste the nectar of her sweet pussy. She just put her head down and laughed, dismissing the possibility for all the obvious reasons: their age difference, his marital status, potential work complications, and more. He dismissed them all summarily, never acknowledging the possibility that he would not get his "taste".

The banter continued, and escalated, with long hidden secrets shared. Secrets that are rarely shared, except amongst lovers, if even then. She loved to suck cock, swallowed, and was good at it. OK he thought, here was the explanation for the MMF preference. He affirmed his love of eating pussy, as well as his prowess in doing so. She said her lover had to have a big dick, which almost seemed to be setting a barrier to entry, so to speak, establishing a standard that most men would not want to risk failing at. He professed that he was comfortably equipped, but, she had heard that before, so the impasse continued. It wasn't until her appetite for anal sex was revealed that the MMF reference made complete sense. He acknowledged participating in the forbidden art, often, but that it was not a make or break requirement for lovemaking.

Their exchanges continued, irregularly, but without bounds as to content. No topic was taboo, or too personal. Then a strange event took place: one day she handed him her phone. On the screen was a naked upper torso, no face, but ample, perky tits he could see himself diving in to. There was a strange comment about sending it to someone that he didn't understand, but it didn't matter. Nor did it matter that it was 'posed' to use her words. The biggest question in his mind, besides 'How do I get between those?' was why? He didn't ponder long, trying to decide whether the next logical step was again, 'worth the risk'. He quickly found his courage, and an old adult swinger's website that he had a profile on. He found a pic of himself, and downloaded it to his phone. It was an older photo, his hair less gray, but what it showed hadn't diminished much over the years. He delicately asked if this were a picture sharing day, and her acknowledgement, while not robust, was a yes, so he handed her his phone. The silence was almost deafening, as if she were trying to determine if this impressive cock really belonged to the man in front of her. Somehow, she made the connection, acknowledged it's place in her history of sucking and fucking cocks, and perhaps came to the conclusion that she was possibly in fact dealing with someone that not only talked the talk, but might just be capable of walking the walk, or more specifically, bottoming out in that sweet little pussy of hers.

A slightly elevated level of banter ensued, if that were even possible. She still dismissed the idea of an eventual union, but it seemed that the reasons were diminishing, but that may have been nothing more than wishful thinking on his part. And then one day, seemingly out of the blue, she made a simple statement: "You're never getting that monster near my ass!" Whoa, so many implications! Did that mean that there was a chance I would get it in her pussy? Or any of the other places it might fit? His head was spinning! He pursued the topic, only to find that she loved to be fucked in the ass, and not just tolerating it, she enjoyed it! And then the revelation that would change the nature of their relationship, her deepest, darkest fantasy, never shared with another; she wanted to fuck a man in the ass with a strap-on! There was not a moment's hesitation as he said "I volunteer!"