I had my first serious girlfriend in the 8th grade, which is pretty normal for most guys. Before that age you're too young and undeveloped to really understand what dating is about. When I hit the 8th grade something clicked for me and all the girls in my class suddenly starting looking really good to me. I ended up dating Missy Selzner, the hottest girl in the class. Of course, we were both ridiculously young so it ended after only a few months, and we barely even kissed, but still, pretty impressive.

I lost my virginity my freshman year of high school, and to a sophomore no less. Her name was Britney and she was another smoking hot babe. It was a pretty awkward experience, and I didn't last very long, but as they always say, it got much better after that. Britney and I ended up dating for six months and we had tons of sex, enough that I felt completely confident going into my next relationship.

All told, high school was like a pussy parade for me. I ended up sleeping with fifteen girls through my four years, a pretty good number considering I dated a number of them for a while. By the time I reached college I had blossomed into a well built, athletic guy and I still had no difficulties roping in chicks. In my freshman year alone I racked up more girls than I had slept with in all of high school, although college girls are much more eager to drop their panties, especially at a school with a party reputation. It was my fateful sophomore that saw my conquest count fall through the floor.

One of the classes I took during my sophomore year was creative writing. I needed an English credit and I had always appreciated people who had the ability to write. It seemed like a good fit, but as soon as I walked in the class I knew I would have a hard time getting anything done. Creative Writing 101 was taught by Ms. Winters, a 39 year old blonde bombshell who had my affections from the first time I laid eyes on her. That first day she was wearing a turtle neck sweater, a knee length skirt, and nude stockings to go with her heels. I felt a powerful attraction to her, something I had never experienced for an older women. She had an air of authority about her, like she would be very comfortable taking over any situation, including a sexual one.

The first thing I did when I returned to my room was log onto the internet and search the web for milf sex. I found a number of sites and eventually settled on using yours, MilfShake.com, for all of my needs. I felt lucky that I had signed up for a single room because I spent most of the day beating off, stroking my cock to orgasm five or six times. I browsed what seemed like endless images and videos of older women posing in lingerie. They were just so beautiful and I couldn't help but fantasize what it would be like to let them control a hot sexual situation. I wanted to lay under them while they rode my cock. I wanted to grope their beautiful breasts through the thin material of their sexy bras and tell them how sexy they were.

I had an awfully hard time sleeping that night and when I finally ventured to the land of dreams my mind was filled with images of Ms. Winters dancing in lingerie. She bobbed throughout my head, teasing me with her beautiful body and those sultry lips. I woke up with a raging boner and managed to quickly squeeze one off before I had to head off to class. I didn't have class with Ms. Winters that day, but I did manage to see her. In fact, I think what I did that day would qualify as stalking.

When I was finished with my classes for the day I hung around the English building waiting for Ms. Winters to emerge. An hour after had taken my seat she came out the doors with a coat over her arms and a briefcase in her hands. I let her get a little bit of a head start and then I hopped up and followed her. The school was in Washington, D.C. so she didn't have a car; instead she took the metro. I hopped on the same train as her, one car behind, and kept my eye on her so I didn't miss the stop. After about 30 minutes of walking and metroing around the city she walked into a ground level apartment, locking the door behind her.

I took note of the address and then went into a local coffee shop to do homework and wait for the evening to come. After a few hours the sun set and I made my way across the street again and stood in front of Ms. Winters' apartment. I could see her in the kitchen preparing a drink of some sort. She had on a bathrobe and her hair was wet. When she left my view I scurried around to the back of the apartment, hoping that I'd be able to see into another window. Lady luck was with me that night because there was a large window that peered right into her bedroom. Moments after I arrived she came through the door, flicking on an overhead light and putting her drink down on a nightstand. After that she stood up again and pulled off her bathrobe to reveal the body I had been dreaming about. She was wearing a shockingly sexy red bra and panty combo that appeared to be adorned with all manner of intricate lace. For a moment she stretched her body, letting a hand rest on her milf ass. Her two cheeks, separated only by a thong, looked beautiful in the shadowy light. I was overcome and I began to rub my cock through my pants. When Ms. Winters turned around briefly to look out the window I was so entranced by her beauty that I, quite insanely, pulled my cock out of my fly and stroked myself to orgasm. I didn't even consider whether or not she could see me, although as it turned out I was well hidden.

I went home that night feeling a mix of exhilaration and shame. I didn't know I was capable of such sexual deviance, but apparently a horny man is capable of almost anything. Creative Writing 101 ended up being my favorite class all year long, despite the almost persistent boners I had whenever I was in the presence of Ms. Winters. After the semester was over and she was no longer my teacher I considered taking a pass at her, but I thought it was better to preserve the fantasy image I had of her.

The summer after my freshman year I had an amazing experience back in my hometown. Armed with my new obsession for older women I was determined to at least fuck one during my three month hiatus, though a relationship would have been great as well. Everything came together one night when my mom had a dinner party for her lady friends. One of these ladies happened to be Nancy Becks, perhaps my mom's best friend and a very sexy milf. She was newly single and I spent the whole night eyeing her as best I could. She was the last to leave the party and when she came out of the house I was waiting by her car. I just went for it, asking her right there if I could come home with her. She had a moment of hesitation, but ultimately her desire for sexual satisfaction won out over everything. Within thirty minutes we were naked on her bed and she was on top of me, riding my hard cock. It was better than I had imagined, so good in fact that she was all for having a relationship. It was pretty awkward telling my mom, but there wasn't much she could do so she didn't make a fuss.

Nancy and I spent the entire summer together. We went to the movies, on picnics, even to a few clubs. We fucked almost every night; clearly being with a younger man had awoken the sexual beast within her. I relished every moment with her and when I headed back to school for my junior year she promised to visit me as often as she could. For my part I promised to be faithful and to try and come home as often as possible. So far, she's visited me twice, and each time it's been a weekend of endless fucking, which is my favorite kind. We'll see how it goes from here, but I have high hopes.

Eric
Washington, DC