My crossdressing story with “Moaning Lisa Smile”

High School Years

When I got my driver’s license, the world of dating opened up to me. My first “love” was a girl that I met in the all-county band. Mary Ann lived in a neighboring town. We really fell for each other. When I would visit her, we would make-out and explore each other’s bodies on the sofa in the living room of her parent’s house. They thought it safe as they sat in a neighboring room, unaware of me having my hand down their daughter’s pants! She would rub my erection through my pants, and sometimes put her hand around my erection, and would bring me to orgasm. Many nights I drove home with a sticky mess in my briefs! Mary Ann was really into sex and exploring our bodies. We graduated to walking to the nearby school playground when the night was warm, and came very close to having intercourse, something neither of us really understood.

Finally, we discovered “parking”. We’d tell her parents we were going to the local Dairy Queen, and then drive to a secluded spot to pull off the road and park. We would kiss, and pet and please each other. Mary Ann insisted that she wanted to give me a blow job. I had no idea what she was talking about. She worked on my cock with her mouth until I came. When I wouldn’t go down on her, she asked me if “it was the smell?” If I only knew then what I know now! Anyway, we lasted for about six months, and then just drifted apart. I later found out that she had come out of the closet as a Lesbian! I lost track of her, but Mary Ann was one sexy girl!

I continued to date as a High School Junior. Most of my interests, being a football “jock”, were the Freshman cheer leaders: cute, petite, skinny, perky girls who wore short skirts and big smiles!

My favorite little freshman blond cheerleader was Judy. She enjoyed kissing and petting. During the summer between my junior and senior years, I would go visit her at her house and her mother, an attractive divorcee, would always leave us alone to watch TV. We couldn’t keep our hands off each other. I mainly put my hand down her pants and played with her wetness. By the time I left for the evening, my cock was rock hard and my balls would be turning blue!

She lived in the country, and the back roads were all dark with few cars. I would pull off on a side road, get out and stand by the back bumper, pull out my cock and, well, jerk off in the summer moon light, right there on the road. Then I would drive home.

I wanted, but never got, a pair of her bikini panties. I particularly remember a frilly pair that I discovered “under a highway bridge” walking home one afternoon from school with her.I slide my hand down her jeans and discovered the lacy panties, and then her fuzzy bush, and then her wet pussy. We kissed and I fondled her.

I would also go visit Judy when she was baby sitting at her aunt’s house during the summer. I wasn’t able to convince her to let me take her picture naked, with her legs open, but I did fantasize about it! We went parking frequently, and many a night after a football game the fall of my Senior year, I would rub her sloppy wet pussy until she came. I loved the smell left on my fingers and the little pubic hairs that were left on the front seat of my car. We even got into a routine after school when on certain days when my mother was away, we would lay on my bed and ravish each other’s bodies. We never had intercourse, but we sure did enjoy each other! We double dated, and even went double parking. I remember one such incident where I was down between her legs, hungrily lapping her pussy, when I glanced up to see the other couple looking over the front seat at us, smiling! Too cool!

Then, it was time to go off to college.

College Discoveries 1974-1978

When I got to college as a small town freshman, I found myself surrounded by lots of sexy young women. We would drink, and even smoke pot. I was having a wild time. I tried to keep things going at home with Judy, but she cheated on me with a local guy, so I ended our relationship. Now I was free to play the field!

I didn’t have a roommate my first semester. I purchased some girly magazines, and enjoyed hours of drinking at dorm parties, followed by jerking off in the privacy of my dorm room. I started with Playboy, and had a favorite edition with Patti McGuire. She later became the wife of tennis player, Jimmy Connors, but I loved her panty-clad photos (white, lace, side bows, sheer), and masturbated over her many times. Wish I still had that edition.

Then I discovered Penthouse, which was even more graphic. I really enjoyed reading the fantasy stories in the Forum section and looking at hairy pussies of the smiling, open legged models. Nice!

I had a couple of casual dates, all with non-intercourse sex involved. One particularly unattractive girl, Bev, got me stoned one night and then tried to give me a blow job. I couldn’t get it up and that really hurt her feelings. She was known as the blow job queen of the dorm complex. Oh, well…

I still enjoyed looking at pictures of women in panties, and fantasizing about what lay beneath the sheer nylon. And, like I did as a young teen, I still liked just looking at panties, even by themselves.

Wolf Alice femulates in their music video for “Moaning Lisa Smiles.”

My crossdressing story with “Moaning Lisa Smile”