I've often heard the expression, referencing a woman, that "all the guys like her". Normally this was made in the context of a fun woman who liked to talk sports, drink beer, and tell bawdy jokes. It took on new meaning for me last year.
I'm Scott. I got a job in Philly right out of college, when I was 22, in a male dominated profession, with almost no women in the workplace. I didn't know anyone in the area, and I should have done more research before finding a place to live because there were few social people near the apartment I got; especially no good female prospects. I am not normally too picky about women -- I love them of all ages, hair color, and bust size. However I seem to like small breasted 50-60 year olds or 18-19 year olds (I've never figured that one out) better than others.
I wasn't getting any ass, and was complaining to one of my older co-workers, Dave, about it one day. He asked what type of women I liked, and when I told him, his eyes lit up -- but he said nothing. A couple of days later, he graciously invited me over to his house in Springfield, PA, for dinner on Sunday, which I gratefully accepted.
When I got to his house, there were several other people there, including a couple of single women, and Dave's wife. I thought he might be trying to fix me up with one of the single women, but Dave's wife Jo caught my attention. She was probably, like Dave, in her late 50s or early 60s, slim with small tits, and dressed to show off her skinny waist, awesome ass, and sculptured thighs. Definitely an MILF! She also had a real nice smile, and a flirtatious manner.
To my surprise Dave didn't sit me next to one of the other women at dinner, but between Jo and another guy. I spent most of the dinner bantering with Jo, who laughed more at my jokes than she should have, and me at hers. Since I was right next to her -- and looking -- I was sure she had no bra or panties, just a sun dress; and when she put her hand on my knee I thought "Holy shit, a femme fatale!" [By the way the meal Jo prepared was great.]
As I was leaving and profusely thanking the host and hostess, Jo gave me a hug and a short kiss on the lips; and I could swear she dragged her hand over my crotch on purpose when she broke away. My brainless little friend sure recognized it -- he had been half hard all dinner but embarrassingly now gave a full military salute. Fortunately I had some papers Dave had given me and was able to cover him up.
I went home and immediately spanked the monkey thinking about all the things I would like to do to Jo. I got little sleep that night, but vowed to put my co-worker's wife out of my mind the next morning.
About Wednesday of the next week, Dave asked me if I would like to go to a Phillies baseball game that Friday night. I said "sure", thinking a bunch of guys were going. When I met him to go, it was just him, another guy in the office, Bill, and -- Jo. I was both thrilled and apprehensive that she was going with us. Both emotions were amplified when Dave sat me and Jo in the back seat, with Bill and him up front, as we drove to the game.
Bill and Dave seemed lost in talk of baseball statistics as we drove to the game. My conversation with Jo started out about baseball, and then moved to light hearted banter, like at dinner. It then - uncomfortably -- progressed to sex. I had to cover my crotch with my baseball cap to at least mitigate the embarrassment somewhat, and thankfully before the conversation got too graphic we arrived at Citizen's Bank ballpark.
I was trying to think about baseball rather than fucking Jo but again Dave sat me next to her, on my left, with Bill next to me and Dave next to Bill. During the entire game, Jo was flashing me -- she had on a short sundress and, again, no bra or panties. I tried not to look, but got glimpses of her little shaved cunt on several occasions. Even though it had gotten dark, I put on wrap-around sun glasses, so I hoped I wasn't too obvious. She gave me a big smile each time she suspected I saw the kitty. I was starting to sweat.
At the time of the 7th inning stretch, Dave and Bill excused themselves, and made it known they wouldn't be back for awhile. The section we were in was mostly older people, no children, and a fair percentage of the fans were drunk and most were concentrating hard on the tight game (3-2 Phillies lead). Dave and Bill couldn't have been halfway up the stairs when Jo grabbed my right hand, caressed it awhile, and then held it on her bare right thigh as she was ostensibly watching the game and cheering. I was conflicted. Her thigh felt great but I wondered what Dave would say.
After a few minutes of my mind swirling while my hand was on Jo's thigh she whispered to me
"Scott, I've got an itch. Could you lightly scratch it for me?"
"Uh, Sure" I stammered. "Where is it?" [I am so naïve.]
With that she led my hand under her dress, along her thigh, to her crotch. If I was conflicted before, now my mind was in a full fledged game of ping-pong! Bad Scott apparently aced good Scott out and I stuck my middle finger in her moist tight little pussy. Jo got a small mind-twistingly seductive smile on her face and cooed:
"Yes, right there."
I fingered her for the next couple of minutes trying as hard as I could to be discrete, as she uttered low, quiet moans, and rested her head on my shoulder. Finally, I knew I was going over the edge, and pulled my hand out. After giving me a short peck on my lips, she pulled out her cell phone, made a call, and simply said "OK" into the phone, and put it back in her purse.
Almost immediately after the call, Bill and Dave walked down the stairs, both smiling devilishly. "What the fuck?" I thought to myself.
As soon as they got back, Dave sat next to me instead of Bill, but with Bill looking on and Jo cackling, Dave said:
"All right Scott, let me have your right hand."
