All characters in this story are older than 18.
When did I lose my virginity?
When I was eighteen. Summer, after high school graduation.
I learned about sex in stages. I knew that playing with my dick in the shower felt really good. Masturbation was something everybody did. We passed our stories around just to impress and entertain each other. Later I learned you should to be discreet about such things such as masturbation, heavy petting and so on. Sex was kind of a taboo thing everyone knew about.
After high school I became acutely sexually aware of women. I had already learned how to masturbate while thinking about a woman's body. I had lots of practice making myself cum. I liked the women. It would be nice to have girlfriend. But I didn't know what to say to them. I was shy and awkward. I lacked the confidence that allowed me to establish a relationship with a woman let alone try to run the bases with one.
I liked the young women I knew in the neighborhood. Intimacy with their bodies was a mystery to me. Their swimming suits at the pool aroused me to no end. They had nice, shapely bodies. And the tits. Those things drove me crazy. Women wore those skimpy tank and tube tops that put their tits on display. I devoted a fair share of my time to daydreaming and fantasizing about what I could do with a woman. I had to find myself a woman friend. That seemed like an unlikely event that would occur any time soon.
During the summer after high school, the neighborhood was a fairly social place. There were monthly block parties and someone was always having a barbecue. The young adults could walk less than a block to get to the closest park. Someone would bring a boom box and we could have a loud gathering. My problem was, I could never hook up with any of the young ladies at these social events.
I was friends with the neighbors across the street. Sherry and Steve were my best friends. Sherry and Steve were twins and we were all born the same year in June. During childhood, the three of us played all the regular games like hide and seek, kickball, badminton, tag, etc. We would go swimming to the local pool and play on slip and slides when it got nice and warm outside. There was bicycle riding and hikes to the nearby fields.
After high school our activities had matured to cruising in cars, sitting in the basement listening to rock and roll and going outside the city limits for the weekend woodsie. There were group gatherings at the drive-in movies and movie theaters and the fast-food drive-ins. Mostly harmless fun. I was never able to meet a woman and hook up.
It was during my eighteenth summer when I finally had my first sexual experience with a woman. It was with my neighbor, Sherry. Steve was there as well. It was a welcome, but very intense learning experience. That experience was all new in the physical sense. Up until then I didn't have any experience of a sexual nature with women (or men). I was completely in the dark about the physicality of sex, other than masturbation. I way a virgin.
Back when I was eighteen years old, the internet did not exist. Porno's were black and white 8mm movies that someone got from a brother in the military. Playboy and Hustler was it for sexy magazines. Most of what I knew about sex came from educational pamphlets and loose talk in the hallway.
Most of my understanding of sex and sexuality came from literature my mother left out in the basement. Mom did not want to have the sit-down "Birds and Bees" talk. It was easier for her to leave the educational materials out where I would find them. With pamphlets at hand, I was free to learn as much about sex as I could figure out. I could learn the content of the pamphlets at my own pace and concentrate on particular areas of interest. If I had a question, I was usually too embarrassed to ask. If I did ask, a new pamphlet would show up a few days later. This was important stuff but I had to learn it out of a pamphlet by myself.
I was always curious about my post puberty dick. The pamphlet explained that it was normal for my dick to get erect and feel sensitive to touch. If the dick was stimulated for a while, it would finally pulsate and fill me with pleasurable sensations. I would be able to have an orgasm. Masturbation, duh. The orgasm would be accompanied by the ejaculation of sperm and semen. So, at eighteen I knew I had a mature dick. I had plenty of masturbation experience fantasizing about sex with women but I had no physical experience with a real woman.
One summer day found us in Sherry's backyard horsing around on a slip and slide. Dress of the day was lightweight shorts and T-shirts. We were soaked to the skin from the sprayers and slide. The breeze on the wet fabric cooled us and gave us goosebumps. We could see each other's nipples poking into the fabric of our T-shirts. It was obvious that Sherry had breasts with much bigger nipples than Steve and I. Sherry didn't wear a bra because her B-cup breasts were very firm and perky. I saw her areolas. They were the size of quarters and very dark. I couldn't stop looking at those nipples. They excited me and I looked at her chest every chance I got.
We sat in the sun and listened to music, drank sodas and talked about plans for an upcoming woodsie down at sand creek. We had already collected enough money for a couple of kegs. Our secret shopper would come by on Friday to pick up the cash and bring the beer on Saturday. All wee needed to get were the tubs and ice. Other party goers would bring the rest of the supplies.
The sun went behind the clouds and the breeze made it chilly. Sherry got up from the ground cloth and announced she was going down into the basement where it was warm. The clouds and breeze were making it too cold. Her skin was covered with goosebumps and her nipples pushed out against her soaked T-shirt. Steve and I also felt the chill. We got up and followed her into the house. Steve and Sherry's parents were gone for the day so we had the house to ourselves. Time to put on some music.
The basement was finished and set up for parties. There was a large screen television and a nice stereo with big Bose speakers. You could really pump out the sound. There was a fridge stocked with sodas and chip dip behind the bar. There were a couple of sofas, a bean bag chair and several nice, padded chairs.
Steve and I were looking for some music and Sherry was flopped in the bean bag chair. It was getting damp from her wet clothes. Sherry said she missed the old days when we played in the basement. I remember marathon Monopoly games where we would actually run out of Monopoly money. I was always the dog.
"We should play Doctor. That was always fun."
I remembered we played that game a long time ago. The doctor game hadn't crossed my mind since that one time I played. I couldn't even remember anything special about playing doctor. Sherry got up and looked at me.
"You're the doctor. Steve, you're the nurse and I am the first patient" she said.
She came to Steve and I and slapped us on the backs. She was taking charge, as she usually did. We were being recruited for the activity we would spend the next few hours on. Where was the doctor's stuff. Did we even have anything around?
"Let's go! Doctors are always late and unreliable." Sherry was urging us on.
Steve and I looked at each other and shrugged our shoulders.
"Okay."
She turned her back to me and said I needed to listen to her breathing and heartbeat. She told Steve to pull up her T-shirt and expose her back.
"We don't have any doctor stuff. Where's my stethoscope?"
