Ted and I had been working on a project on and off for the better part of a week. We had known each other professionally for years and had worked on several projects together. We both live in different cities and collaborate online and eventually meet up in either Dallas or Houston to finalize and present our proposals. This had been a particularly stressful but successful week in Dallas and it was Friday night and time to unwind. Tomorrow, I would be flying back home to Chicago, to my husband.
Ted and I had always had a friendship, but he was more like brother sister. He was a couple years older than my 50 years, and seemed to look out for me. This week however, there seemed to be a little sexual tension building. It may have had something to do with me feeling a little more self confident and dressing to impress a little more than usual. The sexual tension turned up another notch during dinner, but didn't really start to get interesting until we left the restaurant and went to the dive bar a couple doors down.
There just happened to be a pool table in a semi secluded back area which was deserted this particular night. Ted ordered a couple drinks for us at the bar and we settled down for a couple games of 8 ball. I don't deny that I was in a flirty mood, and when he suggested that we put a little wager on the game, for fun, I was all for it. Now I can't shoot pool worth a damn, but figured we might as well make it interesting. Ted suggested that if I lose I would have to undo a button on my top. Ohhh this was going to be fun. I was dressed in black, wearing a flirty pleated skirt just above my knees, and a beautiful tailored silky top with a 3/4 length button placket with about 15 tiny buttons, a couple already undone.
It didn't take too long for my lack of skill with a pool cue to cost me the next two buttons. About this time we lost the privacy of our back room retreat as a younger fellow, about 45, glass in hand, walked back to the pool table. He was a friendly guy and struck up a conversation with us right away. As it would have been impolite to just make him sit there while we played, we invited him to join us. Now we couldn't very well play 8 ball with 3 people, so we decided we'd play cutthroat. We each had 5 numbered balls assigned to us and the object was to shoot the other two peoples balls and the person with any of their balls on the table at the end was the winner.
Ted was all too quick to whisper in my ear that the wagers were still on, which got me just all the more aroused. Well, going up against two opponents proved no easier than playing against one and in short order I was down another 2 buttons, still nothing too daring but enough that each time I leaned over the table to take a shot I was flashing a nice glimpse of my new black lacy bra. The interesting thing though, was how quickly our new friend, Ken, caught on to the wagering, (and the inevitable undoing of another button).
I pointed out to Teddy how Ken seemed to be enjoying the game, considering the growing bulge in his pants and the fact that he seemed to migrate to the opposite side of the table each time I was lining up a shot. I could see from the glint in Teddy's eye that he kinda liked the idea that our little wager was attracting the interest of Ken. I told him that I was going to use the ladies room so he could have a little chat with Ken to see if my intuition was right. Sure enough, when I came back, Ken was shooting and Teddy took the opportunity to tell me that he and Ken did talk, that Ken had noticed and was curious about the undoing of the buttons, and dear Teddy told him all about our little wagers. Now, this was getting interesting! I turned back to the table to watch Ken shoot, and backed myself into Teddy, sashaying my ample bottom right into his growing bulge. I could easily tell that dear Teddy was enjoying this as well!
It didn't take long for me to realise that these two were now ganging up on me, both determined to make sure I kept losing, games and buttons. I pouted, playfully, knowing full well that I was thoroughly enjoying the wagering. By now the buttons were undone well below my bust line already and that black lace was exposed just standing there, let alone while bent over lining up my shots. I finally had to tell the boys that I couldn't very well undo any more buttons in this semi public room. It was their turn top out, and they stood there, their jeans bulging, while they tried to come up with some other wagers I would accept. After a little discussion I finally agreed that whoever knocked me out of the next game would get a nice passionate kiss. It was my idea for a nice kiss, their idea that it be passionate... and I'm always one to compromise soooo... lol
Funny thing is, dear Teddy didn't seem to try very hard. I realised later that this was probably because he knew he had a sure thing for later, so was more intent on making sure Ken won and seeing if I would really fulfill the wager. Teddy didn't have to worry about denying Ken that privileged as Ken ran the table of all five of my balls on his first turn. He turns triumphantly towards me as the last of my balls hit the pocket with a seriously wide grin on his face. As another couple had come into this back area during this game I had to break his heart and tell him I couldn't comply, well, not yet anyway. It was also getting close to last call as well, but we decided to have another game, same wager... same result, and I still had to decline. Not that I wanted to, I would have liked nothing better than to be taken in his arms and given a deep passionate kiss, but not with the extra people in the room. Then, time for one last game. Ken, thinking that there was nothing to lose by suggesting a different bet, thinking as well that it likely wasn't going to be paid out anyway, suggested that seeing as I already owed him some passionate kissing, that we might as well play for a little groping to go along with it. Oh, my, that got me tingling! I feigned horror, of course, but readily agreed... and Teddy just about burst his zipper.
Ken, with Teddy's help, easily won that last game, but the other couple seemed to have no plans for leaving us some privacy, so we decided to extend our little playtime and drive to a little all night diner that Ken knew of about 20 blocks or so away. Ken and I were in no shape to drive, but dear Teddy had the gentlemanly foresight to remain designated driver worthy so off we went. As this seemed the opportune time to pay off the wagers, in the privacy of the car, in the dark, Ken and I giddily got in the back seat as Ted got in the driver's seat. First thing dear Teddy did was adjust the mirror to get a good view. Second thing he did, I found out a little later, was unzip himself. Naughty Teddy. Here he was, so aroused at the thought of me making out with a relative stranger in the back of the jeep, when he hadn't even had that chance with me yet. But then again, he knew that he and I had all night, and that I was pretty much a sure thing for him once we were alone.
The twenty blocks seemed to take forever, not that I minded, and we hit almost every red light between the bar and the diner. Ken and I were deeply involved in very wet, passionate kisses, and he was taking every liberty with his groping. Teddy, while giving due care to the driving, was also very preoccupied with watching. At one point I broke away from Ken and leaned forward through the front seats to plant a wet kiss on the chauffeur. That's when two things happened. First, thats when I noticed that dear Teddy was unzipped and had a firm grip on his 'situation', stroking and tugging at himself through his stretch boxers, which gave me all the more encouragement to give him a passionate deep French kiss. The second thing was that with me lifted out of the seat and leaning so far forward, it gave Ken in the back the perfect opportunity to lift my skirt and start caressing my bottom through my silky panties.
Nibbling away on Teddy's ear I gave him a running commentary of what Ken was doing from behind and with every little exploration Ken did got dear Teddy a little harder. I reached further forward to give Ted to relieve Ted of the burden of driving while stroking and of course that just lifted me further out of my seat and gave Ken even better access. By the time we pulled into the parking lot of the diner, Ken had his hand fully inside my panties and Teddy was very close to creaming his boxers. Ted parked us in a dimly lit back corner of the parking lot, turned the engine off and reclined his seat a bit, allowing me a better angle. As Ken's fingers finally, thank god, found my clit, by this point very hard and wet, I let out a little gasp, whispered the news into Teddy's ear and gave him a few more quick strokes to bring him off. He then, relieved as he was, pulled me into him for some very passionate kissing as Ken was quickly and firmly fingering my clit. The combination of Teddy's passion, and Ken's fingering brought me to a very hard, wet, loud... orgasm... one that I will remember for a very long time.
This gave us all a chance to catch our breath a bit. I knew Ken hadn't had his opportunity yet, but honestly, for Teddy and I, this experience was more for us. Ken already got way more that he could have hoped for and he seemed quite satisfied with that. We decided that none of us were really hungry after all, (and Ted and I really wanted to get back to my hotel room), so we drove back to the bar, and sent Ken on his way, (with a full on body hug and deep French kiss)