Changed names for high school memories, best as I can remember, late 80's
I lost my virginity just before my Junior year of high school ended, after the Prom. I had met a nice girl called Kay, who I helped with Prom decorations, and began dating her when I broke up with my Prom date a week after the Prom, and dated her all summer. I lost my virginity the first week we were together. When Kay and I broke up at the beginning of Senior year, I had an agenda to pursue all the flirtations I might have been too timid to go after back when I was still a virgin.
I was best friends with Jill for most of my Junior year, and we had made out a couple times. I had a few what you might call 'kissing friends' in high school, but that's as far as I wanted to go in most cases as to not upset the friendship(s). I always had an odd place in school life, since I was kind of a jock, and big in science. Jill was someone I could talk to not to mention a strong mutual respect for our strengths in different intellectual interests. There was some definite heat between Jill and myself, and when we made out, she had this crazy darting tongue technique that drove me wild and frustrated me at the same time.
One day that fall when I was feeling flirty, I drove to her house to visit, and see what else might happen. In the days before ubiquitous cell phones, I was pretty good at guessing which female friend would like to spend some time, the mostly platonic. She happened to be home alone, and we started talking about school and music. We were sitting in the 'Train Room,' a small sitting room with a train track running all the way around the wall about four and a half feet up, with a TV on one side and a love seat facing it, with a big rug in the center. Jill was wearing a long dress, like nothing she would wear to school, and was looking a bit unkept, in sort of a sexy way. She was kind of short and broad, with big boobs and a little on the hairy side, but very cute and smart.
The platform the train track was on made sitting in the room, or on the minimal furniture, feel a lot more intimate, and we began talking about our sex lives. She had been doing her homework on the floor, and I pictured her in her dress, her ass in the dress, while doing math stuff. I asked her to join me on the loveseat, and then we started to make out a little.
We were getting really hot, so I started to slide my hand across her stomach (a taboo area in a way, since she fluctuated in weight in different seasons). The dress made it feel even more naughty, since it was kind of an older style that was out of fashion, that she may have worn in junior high. It looked a bit like the old fashioned dresses that were big in the 70's, that whole Victorian thing (sluts in Victorian sun dresses) that made sexual things seem even more taboo.
Her darting tongue was working against my thrusting one, and I moved my hand up to her wonderful 36C chest, big soft boobs that I usually never even thought of, but was now gently squeezing with my palm and fingers. Her nipples were making the dress even more interesting, and I was rubbing them through the linen-textured material. She was wearing a bra, and the dress was a pull-over-your-head type, so I still couldn't see the boobs that I hadn't seen yet.
Still kissing her, I moved my hand south, and started softly rubbing around her thighs and between her legs. My other hand was behind her neck, controlling the depth and passion of our kissing. She sank a little lower in her seat, and I focused between her thighs, her heated area ready for me to explore. I began somewhat lightly rubbing her crotch up and down, through her dress and underwear, as she arched her back a little, and I watched her covered breasts move against the fabric. I started to travel down her thigh again, and came back under her dress to find her damp, hot panties. Her underwear was obviously the comfortable type, not a thong like girls wear now, but not granny panties, and soft enough to not chafe as I rubbed the material up and down against her hot wet crotch.
I began methodically rubbing my fingers up and down her slit through her panties, and alternating that with taking my whole hand and rubbing her whole crotch area up and down. Her wetness increased and I told her to take her panties off. She was nervous because her Mom was coming home soon, and she didn't want to get caught having sex, since she had gotten in some sort of trouble for that in the past. The curtained window of the room was right next to the front door, so we had a little warning. I said ok, and helped her out of her panties.
We dropped her underwear on the floor, and I saw her naked below the waist down for the first time. I should have guessed that she would be hairy, since she had medium arm hair. I could see that she was very hairy, and then I sat down next to her again and started to explore her wet hot pussy. I rubbed her pubic hair, and then went up and down on her beautiful pussy lips with my fingers, rubbing her wetness up and down. I ventured a finger in, cautiously, watching her expression in case I was going too far. I began slowly thrusting my finger into her, deeper as I went, and kissing her beautiful face. She began arching her back and moaning, as my finger went in and out of her hairy pussy.
I started thinking about possibly going down on her, but I had about one and a half weeks of stubble, and along with probably not being good for the thighs, I also had to face my co-workers later, and possibly her mom. I couldn't free her boobs either, so I just focused on her now extremely wet pussy. I took my finger out, and used two fingers to rub her juices up and down her lips, and barely touch her clit in circular motions. Getting my two fingers wet, I plunged them back into her, thrusting along her inner wet walls, and trying to rub along the top where her G-spot area should be.
I kept the motion going, gently thrusting in and out, and tried to undo my pants with my other hand. I remembered one 'date' we had gone on together, that ended with us 'parking' in a known lover's lane area, and frustratingly rubbing her through her jeans as we had a super-hot make-out session. I got my other hand and used two hands to undo my jeans (damn button-fly!) and asked if she would touch me. I went back to fingering her, this time with one finger, sliding in and out, making a little noise because of her wetness. She gingerly started touching me through my underwear. I indicated that I wanted more, but she was really into what I was doing to her, and could barely concentrate on my now stiffening penis.
I kept thrusting my thick finger into her, and she started gasping, and her pussy was tightening around my wet finger. The ecstatic expression on her face was beautiful, and I think I was taking her through her orgasm, keeping up my rhythmic thrusting, and rubbing her pussy lips a little more, watching her. I kept thrusting while she was moaning, and she finally put her hand under the waistband of my underpants, and touched and squeezed my stirring member.
Just then I saw something in the window, and heard a strange noise. It was her mom jangling the keys on her key ring! Her mom was looking for the house key, and gave us just enough time for Jill to shove her panties in a pocket on her dress and straighten herself up, and me to run to the bathroom to wash the pussy juice off my hands (decorative soaps only, son of a bitch!).
We of course looked guilty as hell, but I made a quick exit. I heard later from Jill that her mom had given her a pretty strong warning about having a guest in an unchaperoned house, but her mom really liked me, so after awhile we were all ok.
Later that school year, I was kind of getting more serious about dating, and asked her out again. Even though I had my parents house all to ourselves all night, and some erotic movies to set the mood, we ended up snuggling and holding each other, with minimal kissing, just being kissing friends by the end of the night. Best Friends.