Under the influence of 3 drinks, Judy was getting flirty, while Deborah seemed to withdraw. Judy had just broached the subject of sex: she'd asked me to talk about the strangest thing my wife and I had done. I answered truthfully, "Well, you might find it pretty weird, but hopefully not creepy weird." I went on to explain how a medical condition had made sex prohibitively painful for my ex, dating back 15 years or so.
Deborah was listening intently, while Judy was asking the questions. "Wow, no actual sex for 15 years?"
"Well, this is the sort of weird part. What we did instead was," I began to try to describe my sex life at home before my divorce, but it was kind of delicate, as I'd had a professional work relationship with these ladies a few years back, and felt uncomfortable using crude language. In fact I had supervised both, although not at the same time. I continued, "she used to...um...tease me for a while, then I would go dow...uh, eat...um, lick...ah, give her oral."
Our meeting at the restaurant was purely coincidental, having arrived at the same time. I was there to order take-out; they ate there together every Tuesday as a matter of habit. Judy suggested we hit the bar first to catch up. I was telling them about my recent divorce. I knew they were both divorced.
"What about your needs?" Judy asked.
"Oh, I...took care of myself."
Judy made circle with her hand and did a jerk off pantomime; she had always been just a little bit crude. "Yeah that's pretty weird all right. Bet you're glad that's over."
Deborah remained silent, a serious look on her face, but it seemed to me that her breathing was getting a little faster, barely noticeable.
I said, "Well, you know, you get accustomed to something and, it starts to feel normal..."
We were in a booth, Judy and I on one side, Deborah across from us. Judy moved closer and began to touch the top of my leg lightly every time she spoke, about half-way between knee and groin.
"I bet you miss the kinky stuff, don't you?" Judy said with a giggle.
I think I blushed a little bit. I didn't say anything, but I did kind of look off into space for a moment, remembering, and started to smile. When I realized what I was doing, I shook my head, as if to clear the cobwebs.
"Oh yeah, look at that face - you wish you could it again, don't you," Judy said teasingly, a half-smile on her face, eyes narrowing slightly.
The light touches on my thigh were starting to have an effect; I found myself starting to become aroused. There was nothing really objectionable about Judy; she was in her 50's (like me), in reasonably good condition; she had what you might call average sized breasts, and black hair (obviously dyed). She just wasn't a pretty girl. But pretty is not the same as sexy. I'd never considered Judy sexy before, but I was married back then, to a pretty woman.
I hesitated for a moment, studying her face for a clue as to where she was steering this discussion. "I guess I haven't given it much thought," I finally said. Judy smirked at that. Even Deborah smiled just a little. I knew I was busted. I continued, "I suppose...but I would have to...I mean, where would I...I mean, it's not the sort of thing you can just bring up in any conversation."
"You brought it up in this one. Sounds like an invitation," Judy said with a laugh. This time she let her hand rest on my thigh. I decided to act as though I didn't notice. I figured at that point that she was game for just about anything, but still, I was reluctant to discuss it. Fear of rejection has cost me many opportunities over my lifetime, what's one more?
"No," I said, "I mean, uh, that's not really what I meant - I've never discussed it with anybody, so...and I didn't start this conversation anyway."
A few minutes of silence, the three of us sipping our cocktails and eyeing each other. Deborah, also in her 50's, had wide shoulders, extra wide hips, and small breasts. Her long blonde hair was pulled back into a pony tail, hanging limply. Neither of these ladies would be the subject of anyone's fantasy, but we had worked together for several years, and I considered them friends.
Lucky for me, Judy wasn't giving up so easily. "I don't know, what do you think, Deb? I think he wants to play," she said.
Deborah's expression never changed. Her face was impossible to read, but I knew her pretty well; I knew if something offended her, she'd let us know about it. If she had any objections at all to the topic of conversation, Deborah would have put a stop to it.
Trying not to sound nervous, I said, "Are you saying...," I paused.
"Go on," Judy pushed me to finish, leaning towards me, sliding her hand over, her fingers coming to rest on the inseam of my trousers.
"Ok," I plowed along, "That doesn't sound like fun to you?" I laughed nervously. I wanted it to sound like light-hearted flirting, but I think I was coming across as rather pathetic.
Judy didn't miss a beat, "Are you kidding? Where do I sign up?" she said with a smile. As she spoke, she straightened up a little, drawing her hand higher on my thigh.
Finally Deborah spoke up, "Wait a second, are you saying you'd do that with just anybody." She hadn't smiled since the topic turned to sex, and I half expected her to get up and walk away in a huff.
"No, no that's not what I'm saying at all."
With this, I slumped back on the seat, thrusting my hips forward and opened my legs a little, toying with Judy. But she didn't give an inch. She held her hand steady, and the tip of my half-hard dick made contact with Judy's wrist - just barely, but I noticed her eyes widen for a second.
"Oh, so you were just teasing us then," said Judy with a twinkle in her eye. She started tapping the inside of my thigh with her fingertips. My cock grew a little longer, pressing a little harder into her wrist.
"No, not teasing. Is that a yes?"