During high school and college I had my share of girls. But, as with most guys, I always fantasized about what I couldn't have. I had been dating my girlfriend Lisa since my junior year of high school, even though we'd been going to different colleges for 3 years. We visited each other about once a month, so I obviously had to dip into the local supply of sorority pussy. I'm sure she new I was getting some on the side, but she never mentioned it. She probably never mentioned it because she was probably doing the same thing.
Even though I was surrounded by beautiful girls at school, I never fantasized about them like I did about Lisa. When I looked back at why I was like this, I realized it wasn't Lisa; it was her mother Diane that I was fantasizing about. Lisa was a beautiful girl but her mom was an extremely hot woman. Lisa was a slightly shorter, less voluptuous, plain version of her mother. They had many similar features, but Dian always dressed in sexy outfits for work and her actions and smell just screamed fuck me.
Let me paint a picture of Diane so you can get an idea of what I'm talking about. At the time of this story Dian was 41 and working for an advertising agency down town. I don't know what it is about advertising chicks, but even today, when I have an appointment with one, they're always sexy as hell and dressed to the hilt. It must help them close deals, well at least with a horn-ball like myself. Oh yeah, back to Diane. Diane is about 5-9, 135 lbs., long blonde hair, and a great tan. She always wore tight, short skirts and tight or partially see-through tops, showing the world her huge D-cup tits.
I remember one time vividly. I was picking up Lisa for school, and Diane was rushing off to work. Diane answered the door in a black mini-skirt and a white see-through blouse. My eyes immediately fell to her tits. I could easily make out the lace pattern bra that cupped her heaving breasts. She quickly looked down at her chest and noticed that she had missed the top 3 buttons of her blouse. She quickly closed her shirt with one hand and apologized for showing me her "old lady" breasts. I replied, "They don't look that old to me." She smiled and told me," don't let my daughter hear you say that." She then walked over to her heels bent over and began strapping them on while I watched. I could easily make out the outline of her thong through the shear material of her skirt.
When she finished, she stood up and turned around towards the door and me. She did her sexy swagger, which is her normal walk, toward the door, so I turned to give her some room to pass. She then did something totally unexpected. She walked up to me, placed one hand on my lower stomach, locked her sexy eyes with mine, and then gave me a quick peck on the cheek. "You have a good day," she said, with a smile and a wink. I stood there with my heart racing, and a huge boner. I know she loved the fact that she could do that to me. She walked to the door, turned and gave me another wink, and then left. Lisa then came down the stairs, "what's wrong?" she asked. "Nothing," I replied. And that's how my fantasies of fucking Diane became an obsession.
Every summer during college, Lisa and myself returned home and spent it with our parents. During my junior year, my parents sold their house and moved to Florida. I was pretty pissed until Lisa suggested I could stay with them. Lisa's mom, Diane, had just gotten divorced from Lisa's playboy dad and was lonesome. When Lisa called me with the news of her mother thinking it was a great, I was ecstatic. Lisa said there was one problem, her finals are going to be the week after mine, so I was going to have to hang out with her "boring" mother. I pretended to be disappointed, but I was actually very excited.
The day finally came; I packed up the Jeep and headed for Diane's, where I would have seven days to be alone with my girlfriend's super-sexy mom. I arrived Thursday afternoon, got the key from under the mat, and made myself at home. Diane left me a note that she had to work late but that she would make it up to me. I stayed up until 1 A.M., but I was tired and retired to bed. I awoke at 9 the next morning and hurried down stairs. Diane was already dressed and leaving the house. She apologized and promised to come home and cook me a good dinner. I was beginning to think my fantasy was just that, only a fantasy.
At around 4 that afternoon Diane returned home with three bags of groceries. I met her at the garage entrance in the kitchen and asked her what I could do to help. She told me that the pool had just been finished for the summer season, and she wanted us to have a summer opening barbecue. The biggest help I could be was to get the grill out, and get ready to barbecue. I went out and got all the equipment from the utility closet. I managed to clean it all in about a half hour. When I went back inside to tell Diane I was done, I saw the most amazing sight. Diane was standing at the counter preparing a salad in a very skimpy bikini. It was lime green with spaghetti straps and triangular pieces of material barely covering her nipples. The bottoms were a thong bikini, covered by a sheer, see-through skirt, which was the same green color as her bikini. She turned and told me to go throw some trunks on, so I quickly obeyed so I could return to admire her great body.
We went outside and started up the grill while she drank wine and I drank beer. We talked about school and her job for a while just to keep up small talk. When the alcohol began to settle in, the conversation moved towards girls, sexuality, and other things you usually don't discuss with your girlfriends mom. She was telling how she hadn't had sex with a man, for over a year, and that she hoped that she was still attractive. "Attractive!" I said, "You have an unbelievable body. Not only are you hot for your age but you are better looking then most girls 20 years younger than you."
