My first experience with a Cougar was during summer holiday from college. My brother and I still refer to it as "The Summer of MILF". My brother and I were spending the holiday at our parents home. It was a great place to grow up and we always enjoyed returning home for the holidays. Our parents had left for a business trip and we were left to take care of the homestead. We spent our time swimming, sunning, relaxing, and trying to get laid.
One afternoon my brother and I were out in the pool house enjoying the sauna. I had stepped out to cool off under the shower. I was just enjoying standing under the water, eyes closed, I started to stroke myself; I was off in my own world. Then I was brought back to the present when my brother came out of the sauna and said my name. I opened my eyes to see our mom's best friend standing in front of us with her mouth hanging open. It seemed like an eternity passed as she stood there looking at us; I just stood there and continued to stroke my huge erection. Then she stepped into the shower, dropped to her knees and started to stroke and suck us until we came; which did not take long. We soon had her out in the lounge stripped naked. I always thought that she was a great looking women, but nude she was drop dead gorgeous. A true red head that was red top to bottom, and she had a bush that was very thin and light. Back then women were not shaving everything like today. Our girl friends to this point all had big hairy bushes, so eating this pussy was delightful. We spent the rest of the afternoon sucking, screwing, and eating pussy.
That afternoon during a break in the action she had said that she had come over to see if we needed anything; check up on us, ask us over for dinner. She told us that our mother had said in the past that our father had a large cock. At the time she thought she knew what that meant, she imagined that dad was a bit larger than her husband. Then when she walked in on me and was just dumb struck. She had never imagined, let alone seen, cocks as big as ours. Without even considering her actions she decided she needed our big dicks; and she got them.
This was a big change for my brother and I. Up to this point, since we became sexually active, girls we knew were not very excited about our large cocks. Activity with our girl friends would progress from groping to stroking, to oral sex, and then to the main event. But most girl that both of us had been with would choose not to have intercourse, they said they were just to scared of our huge dicks. Growing up our father had told us that no means no; so we repected their decisions. This experience of having a women want to get fucked by our big cocks was new to us.
That evening after dinner time she came back over for another round. Everyday that week that our parents were gone she came over for us to screw her. A couple of times she brought over another friend for us to fuck. It was not long before it seemed like every middle age mom in the neighborhood knew we had big cocks and would screw them at the drop of a hat. These ladies kept us busy that summer doing odd jobs around their places. After cutting the grass, cleaning out gutters, or whatever task that was need was complete we finish up with the main reason we were over and that was to screw the lady of the house. My brother and I made alot of money that summer on those jobs. He still jokes that we weren't handymen, but well paid gigolos. I counter that we were just cheap man whores, I would have screwed them without the odd jobs or the cash.
We would both agree that it was a great experience. But it was not without some problems. There were 6 MILF's that we were screwing. They were all friends of our parents, four of them were the mother's of our buddies. Trying to be discreet often difficult, especially for the women. They all knew we were screwing the other ladies, I was scared that their husbands, our buddies, or my mom would find out. To this day I have no idea how my parents never learn of our actions. Several of the women I continued to screw through my college years screwing on my holidays.
As for my mom's best friend I still see her about twice a year, when I am in town. She is as hot today as she was then. She is a tri-athlete and is in incredible shape, and can screw like there is no tomorrow. The only thing that has changed is that today she is no longer has that lightly red haired pussy, she has had her pussy lasered and it is beautiful and smooth. I might just need to make a trip to my home town and drop by for a screw.
