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 naΓ―ve.]
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."
I started to resist, but Jo changed her cackle to a full blown chortle, and said:
"Go ahead, Scott, you need to give him your hand."
I stopped resisting; Dave brought my middle finger up to his nose and sniffed, turned to Bill and said "Damn she's good". With that they each took a $20 bill out of their wallets and handed it to Jo.
"Nice doing business with you boys" was all she said as she stuffed the bills into her purse. Then the three of them acted like nothing happened and they cheered the Phillies to victory. I mostly sat in stunned silence.
On the way back, Bill and Dave were lost in talk of the game while again I was in the back seat with Jo. Only this time it was dark. And it was clear Jo wanted more finger fucking, and also exposed her tits. I realized resistance was futile -- and in view of Dave's and Bill's reactions earlier there was no reason for resistance -- so I finger fucked her most of the way back, with one and then two fingers; she was too tight to fit a third in. At the same time I was stroking or sucking on a tit, but I had to be careful because she had such sensitive nipples she starting squirming and moaning so much when I touched one I thought for sure Bill and Dave would have to look back. It got me so hot that when she put her hand on my crotch I came right in my pants, like I was a horny teenager.
When we got back my finger-fucking hand was soaking wet. Jo seductively wiped it off on her dress, and popped her tits back in her top. After we exited the car Dave asked if I wanted to join them at a club the next night -- Saturday. Jo was looking at me wide-eyed biting her lip waiting for my response. I didn't know what the hell was going on, but the ride back in the car was my most fun -- by far -- since getting to Philly, so I said "Yes".
"We'll meet here, 8:30 tomorrow night" Dave said as I nodded.
Things had been bizarre so far. I was hoping they might get even more bizarre because I sure wanted to fuck that little minx.
When I arrived at Dave and Jo's Saturday night again she was the only woman. Dave, Bill, one of their neighbors, Jim, me, and Jo, were the fun-seekers.
Jo looked great. She wore a slinky black dress with sequins, 4 inch red high heels, and nothing else. We had a drink at the house before we left. This time Jim and Bill crawled into the back seat with Jo between them, and Dave and I sat in front. From the sounds coming from the back seat -- Dave ignored them as he chatted me up -- it was clear Jo was being finger fucked by both guys.