This is another story about my high school girlfriend Jenny and me. I just remembered this particular night because I happened to be driving in that area recently.
I lived maybe a 30 or 40 minute drive from Jenny. I would always get excited to leave my parents’ house and enjoy the freedom of driving myself up to Jenny’s house. I was always impatient to get to go see her, so I would quickly eat whatever my mom made for dinner and then go get her. My car was an absolute piece of shit, so the stereo did not work. I strapped a boom box in the back seat and put in a mix tape I made. That gives you an idea of the time period.
It was late Fall and the leaves on the trees were almost gone. The time had changed and it was dark out when I left my house. I drove on dark, empty country roads along a river and then a straight road lined with cornfields for half the drive. I loved the feeling of driving myself at night up to Jenny’s. I pulled up in front of her dad’s house and she came down the front steps. Jenny was petite, thin, had short reddish brown hair, brown eyes, small tits, and a nice ass. She was very cute. She was wearing jeans and a sweater. Jenny hopped in my passenger seat and gave me a kiss.
We were going to hang out at my friend’s house that night, but it was still a little early to head over there. Jenny and I dated for most of high school, we were each other’s first kiss, and everything else. It was senior year, at this point we had already had sex before. I said, “Jenny, do you want to go park and listen to music?” Jenny said, “Okay.” I am sure she knew that we were going to do more than listen to music, but I am not sure I was ever bold enough to just say do you want to go have sex.
We pulled into a small, dark parking lot for a little playground by a river. We actually were listening to some new music and talking. Then we started kissing. Jenny had really nice lips, she had this sort of pouty lower lip. Jenny broke the kiss and said with a naughty smile, “I got new underwear. I think you will like them.” That was something very fun about Jenny – she liked to show me her panties. She was somewhat timid in some other ways, but enjoyed showing off her panties for me and I loved seeing them. I guess it also shows that she knew we were going to be fooling around because she picked out her underwear for me.
I said, “Can I see them?” Jenny smiled and started unbuttoning her jeans. She spread open the fly of her jeans to expose the front of her panties. I said, “I can’t see them, you need to pull down your jeans.” She pulled her jeans down, so I could see her underwear.
They were bikini cut with a floral print. I think they were silk. I rubbed her pussy a bit over the top of her panties and then put my hand down the front to touch her. I said, “I like them, but I like what is underneath even better.” I reached over and started pulling down her panties. She lifted her butt to assist me and I pulled them down below her knees. I think she said her butt was going to freeze because it was cold out. She had nice, thin legs terminating in neatly trimmed dark bush. My hand made its way up her inner thigh to her pussy and I rubbed it a bit.
I leaned back away from her to unzip my jeans. I pulled down my pants and boxers down below my knees, to expose my very hard dick. I think just being around Jenny usually gave me a boner, but seeing her panties and then her pussy I probably could have used my dick to hammer nails into wood. She started stroking my boner. A lot of guys don’t like handjobs, but I loved how she stroked my dick. Feeling her thin fingers wrapped around my dick, she just knew how to work my dick.
I reached back over and parted her labia and put my middle finger in her pussy as far as it would go. She was very wet. Her pussy felt warm, wet and silky on my finger. I moved my finger in and out and rubbed her clit as we kissed and she stroked me.
I said, “Will you suck it?” Jenny leaned over and put it in her mouth. It felt amazing in her warm, wet mouth. I watched her head bob slowly up and down and I reached over with one hand to caress her bare ass.
As she sucked on my dick, she made an audible slurping noise as she pulled her mouth off the head at one point. I said, “What was that sound?” Not sure why I made that stupid comment, but I did. Jenny said, “Me”, but she had my dick in her mouth when she said “me” so it sounded like she was talking with her mouth full. Kind of random but I found that sort of hot.
After a bit she stopped. Jenny did not want cum in her mouth, so she would always just suck it for a bit. We went back to fingering and handjob. She had her face buried in my chest and I whispered/half moaned I in her ear, “Will you suck it some more? It feels so good” She leaned over and started sucking me again. I loved the feel of her lips moving up and down my dick. She did not go very deep because she had a gag reflex, but it still felt really good and she would use her hand at the same time.
She sat up again and we continued touching each other. She jerked me until I came all over her hand. There were conveniently paper towels in my car for checking the oil in that rust bucket. So we cleaned up her hand and my dick. Then we pulled up our pants and headed to my friend’s house. I remember being at my friend’s house and she and I kept giving each other sort of naughty looks. I think his parents were home or else we probably would have fucked somewhere.
Source: reddit.com/r/Erotica/comments/qpjlob/date_night_with_my_high_school_gf_jenny_mf_18