The New Girl

He had a substantial void in his recollections of the evening they met, which, given their professional relationship, was a serious concern of his. He was afraid he may have wandered over the line while sitting next to her at the bar, and she would have something to potentially hold over him. And in fact, she did offer that he became somewhat 'touchy/feely' during their initial meeting that night. It was a playful remark, and he took it that way. But there was also the implied admonition that 'touchy/feely' had no place in their relationship. But he wasn't sure she was serious, or perhaps he just didn't care. Pursuing her was worth the risk.

Other than the initial revelation of her desire to fuck a guy with a strap-on, and his volunteering for the duty, the subject did not come up again. Just as well, for the time being anyway.

He never considered himself to be dom or sub. Nor did being in the immediate proximity of a cock while fucking another man's wife cause him to think about anything other than pounding the pussy in front of him. But, he had enjoyed having a toy in his ass during conventional sex with previous partners. No, that wasn't entirely true. The vibrations of the toy against his sphincter carried right through to his dick, and right into his partners' pussy, causing the most extraordinary, unconventional orgasms either one of them had ever felt!

So he couldn't help but wonder what a nice pair of tits bouncing against his back while being drilled by a strap-on would feel like. To be able to reach back, grab her ass cheeks, pull her in, deep and close.

He had no idea of what the impact of her watching the strap-on pound into his ass would be.

Could she feel the other end of the dildo pounding against her own pussy?

Maybe she needed a jumbo butt plug/vibrator in her own ass so she could share the experience?

He would eventually bring himself to climax, while fingering her clit and bringing her own climax to an explosive end!

But, he would have to wait, as that could never be their first encounter. He would need to prove he could satisfy her pussy, and possibly her ass, before asking her for similar treatment.

However, her intrigue with the size of his dick did persist.

He had only physically touched her once in a sexual manner. A quick, or perhaps not so quick, handful of her right ass cheek during a congratulatory hug after her divorce was final. While she didn't encourage him, neither did she pull away, something she vowed would happen earlier in their relationship during the 'touchy/feely' discussion.

She often remarked about the size of his hands, trying to correlate the size of his dick with the size of his hands. At least now she had a real reference, seeing that old picture, and perhaps fantasizing on riding that beast?

"Did you have anal sex with all of your previous partners?" she asked.

"No, not all. Some just were not into it. No biggie, not a fundamental need for me" he answered, again wondering whether she would consider trying that big dick of his on for size in that cute little ass at some point. Despite her admonitions that it would never get near her ass, he couldn't help but wonder.

Changing the subject, and believing he already knew the answer, he asked nonetheless: "Have you ever tried a threesome?"

"No. I had a chance with my ex's friend one night after a trip to the strip joint. His wife and I got a little too much into the show, and after we got back to their place, he said I could fuck him if I wanted to, but I couldn't bring myself to do it. Guess I'm a one man woman?"

"I'm not sure that's what it means at all, especially from someone that wants to feel a cock in both her ass and pussy at the same time." I needed to convince her that she was in a different place now that she was single, that her previous experiences were not an indicator of things to come, and that I needed to be part of that new experience.

"You want to fuck two guys, or better said, want two guys to fuck you at the same time, don't you?" Before she could answer, he added "And having a third guy for you to suck off at the same time would be the cherry on top of the Sunday, wouldn't it?"

She didn't answer, absorbed in the visualization of having every hole filled to the brim with big, juicy cock. His big juicy cock, he hoped.

He could almost see her upper thighs quivering, and he desperately wanted to reach out and help her with the orgasm she needed so badly to experience. What he really wanted was to get between those quivering thighs, and taste her sweet nectar, while she fantasized about him pounding her pussy, or her ass, or even sucking his juice out of that monster cock while others filled those holes. But the time wasn't quite right, and there was no overt acknowledgement that she wanted him the way he wanted her.

He had plenty of time, his seduction of her had only begun. And he never left a doubt in her mind that he would taste and fuck that sweet pussy of hers.

Though she continued to deny a potential coupling, citing the usual reasons: work complications, wife, age difference, they seemed to have less conviction than before.

She didn't want 'work complications'. "Work complications? Are you kidding? We've transcended the bounds of both propriety and 'work complications' long ago" he reminded her. They had already gone so far beyond 'work complications': their banter, highly sexually charged conversations, exchanging nude pics and flirting, which could easily leave him outside looking in if it went wrong, were nevertheless becoming the norm.

Yes, he could almost taste that sweet pussy of hers, and began to consider when and where it would happen. It would have to be carefully orchestrated. She had to be willing and complicit. The road to getting in to her pussy had to be the result of her wanting his cock. But the seed had been planted, and while it grew, he had plans to make!