Back in my senior year of high school I had my first date with a beautiful girl named Lisa. Since we both had been held back a grade we were both 18 years old. That last year of high school turned into a sexual odyssey that cannot be easily forgotten.
Our first encounter was on a blind date with her as we doubled with one of her girlfriends. As was usual back in the day, the four of us ended up at a drive in movie. Lisa and I sat in the front seat and my friend and his date in the back seat. It did not take long before some making out was starting in both sections of the car. As I started to lie across both bucket seats, Lisa climbed on top of me and we continued to kiss. It didn't take long for my cock to go rock hard and I knew that she surely could feel it through her clothes and up against her crotch. The next step was a mutual dry humping while kissing and oblivious to anything that was going on in the back seat.
Without any warning Lisa then grabbed my cock through my pants and started to jerk me off. I couldn't believe it. Having just met this beautiful girl and then to have her stroke me on our first date was absolute heaven. In no time at all my cock started to spurt cum all over the inside of my underwear and pants. She must have known enough about the male anatomy to realize I had popped my load and she released her hold on my cock. This was the beginning of the journey and needless to say I wanted to date her again.
Our next encounter was a "date" at her house. Upon arrival I find her in a dress with stockings. She takes the time to explain that her parents are gone for the afternoon. We quickly move to the couch to start kissing. As hormones start to rage we find ourselves on the living room floor with me lying on top of her, again dry humping. Not knowing how far she will let me go I try to work her dress up her body. Once again she reaches for my cock and massages it to a rock hard erection. I continue to move her dress up to her waist but cannot determine how much progress I have made without being totally obvious as to what I was doing. We took a break in the action and I got up from lying on top of her. There she lay with her dress up around her waist. In full view were he cotton white panties covered by her panty hose. Some of her public hair was peeking past the edges of her panties but still not exposing all of her sex. As she got up and looked down she realized she was somewhat exposed. I apologized for the position of her dress but she commented it was no big deal.
After having a drink we returned to the floor and she started to jerk me off through my pants again. So grateful for the attention my cock was getting I wanted to return the favor. I started to massage her pussy through her dress. As things grew more and more heated I just pushed her dress up again and massaged her through her panties and hose. Not knowing exactly how to give her an orgasm I continued to rub and so did she until I once again came in my pants. That was when we heard the car door of her parents car close and we quickly straightened ourselves before they came in the house. My biggest fear was that there would be a huge wet spot leaking from my jeans.
Thankfully there was no wet spot.
As the months passed I was dropping my load on a regular basis although through my pants. Then one night on a date at the drive-in she unzipped my pants, moved my underwear to the side, pulled my dick out and just started jerking me off. The excitement of being exposed, not only to her but the rest of the world, caused almost an immediate explosion. Lisa wiped my cock up with my underwear as best she could and stuffed it back in my pants. I calculated that this was her signal that I could also reach beneath her clothes and touch her bare skin. Unbuttoning her jeans and unzipping them was the first layer. Inching my hand down from her naval I snuck under her panty hose and panties, all the time waiting for her to say stop. But the stop did not come. Reaching the top of her pubic hair it appeared to be all clear to go further. I finally reached the top of her pussy lips and poised my middle finger to slide down her slit to her hole. The journey of my finger got wetter and wetter until I reached my goal. The panty hose and panties constrained the movement of my hand and arm. While she moaned and her hips responded to my touch I just sensed that she was not going to reach the ecstasy I had with my orgasm. After twenty minutes or so of finger fucking her and grinding on her pubic mound she claimed she was satisfied and that was enough.
A few more of these dates became the norm and while somewhat satisfying our clothes were definitely getting in the way.
One afternoon I arrived at her parent's house to find that they were not home. Her mom, dad and little sister had gone out for the day. We had planned to go somewhere but quickly ended up on the floor. She was wearing a dress. Once of the floor she immediately unzipped my pants and pulled them down to my knees along with my underwear. With my cock fully exposed in daylight for the first time, I reached under her dress and grabbed at her panties and hose. She stopped me in my tracks and said, "No. One at a time incase my parents come home early."