Author: angle_madeup

The first time my high school gf, Jenny, made me cum. (MF 18)

This is another story about my high school
girlfriend Jenny. For anyone who has read them, I have written these in no order whatsoever, sorry. These happened a long time ago, so I have written them as I remember them. There is a story about an awkward boner that happened chronologically before this story and might make sense to read first. This is the story of how we first started getting sexual.

For anyone who has not read any of the others or to remind you, Jenny was petite, thin, short reddish brown hair, brown eyes, small tits and a nice ass. She was really cute.

Despite the fact that Jenny could feel that I had a boner the first time we had any physical contact with each other (the aforementioned awkward boner story), we actually dated for a while before we did anything sexual. We did a lot of hugging, kissing, and snuggling. There were some long make out sessions and those were memorable as well. Read more »

Jenny (my high school gf) and I break up after I leave for college and have break up sex (MF)

Jenny and I dated through most of high school, but she was one year below me in school. After my senior year, I went away for the summer and when I came back, we saw each other a few times before I went off to college in another state.

We did not really talk much about how it was going to work, but we did decide to keep dating. This was pre-internet, pre-cellphone days and long distance calls actually were not that cheap back then. So, when I went to college we talked on the phone very occasionally. I think we wrote a few letters. I visited my parents’ house a few times that Fall and for Christmas Break. We always saw each other, went on dates and had some fun sex when I would visit.

But, at some point in the Spring of my freshman year of college, we broke up. So this is the story of how we broke up and the last time we had sex back then.

I think Jenny I had not really talked much or seen each other since maybe February or so but I am not sure. I came home for a long weekend in the Spring and I decided to surprise her by picking her up from school. Read more »

An awkward boner with my high school gf Jenny. Prequel to other Jenny stories I have posted.

I have written other Jenny stories on here and this is sort of like the prequel or the origin story. This is the story of how i ended up getting together with Jenny and I would say that this night that I got an awkward boner was the actual start of our relationship. To warn you, story is only barely not safe for work.

Jenny and I were only in a couple of classes together the first year we met, but we were in band together, so we saw each other after school and at events. We were sort of in the same group of friends from band although she was one year below me.

I cannot remember exactly when, but at some point I started really noticing Jenny. And apparently I was not very subtle about looking at her (I found this out only many years later). I would look at her and she would see me looking at her and get nervous. Jenny was super cute. She was petite, thin, short reddish brown hair, brown eyes, and a few freckles. She also had a nice ass and small tits that were proportional to her body. She was not very shy in groups, but she was shy around me and her brown eyes had this sort of nervous look whenever I made eye contact. Hard to describe but I found it very innocent and cute. Read more »

Date night with my high school gf Jenny. (MF 18)

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. Read more »