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.
Jenny was open with her friends that she had a crush on me and some of that made its way to me despite my general cluelessness. At some point, I was aware that she was into me, but I was always a bit timid with girls. I was interested in girls and actually had a fair number of girls interested in me, but I was pretty good at losing girls by never making a move.
So, it kind of looked like I was on a path to screw it up with Jenny, much like the others. There were a couple things going for me this time. Jenny was really into me and it was pretty obvious even to me. And, I had a wingman, or perhaps Jenny and I had a wingman.
Our wingman was an older girl named Kim (not her real name). Kim was friends with Jenny and she was almost like a big sister to me. Jenny told Kim all the time how much she wanted me. In fact, we were in the same gym class and I think I remember seeing Jenny in our dorky gym uniforms, looking over at me and saying “I want him” to Kim. I don’t think I told anyone that I was also into Jenny, but maybe it was obvious.
So, one night, there was an event at our school. I don’t remember what it was, but it must have been boring because a bunch of us decided to leave and just go drive around. I think anyone from a sort of rural area of the US can picture this.
There were six of us who decided to go for a ride; Alex, Kim, Joe, Zoey, Jenny, and me (Jack, not my real name). Alex had his drivers license and a car, so he was driving. Kim was the oldest and bossiest so she took the front passenger seat. That left four of us to sit in a back seat of a small car designed for three passengers.
This is where Kim became the ultimate wingman. As we were all climbing into the car, she said, “Jenny, why don’t you sit in Jack’s lap.” There was definitely no argument from me. So, I sat by one of the back doors, Zoey was in the middle and Joe was against the other door.
Jenny climbed onto my lap. She said, “I don’t want to squash you.” Jenny was too small to squash anyone and I was thrilled to have her sitting in my lap. I responded very eagerly, “I’m fine – you’re not squashing me.” There was no way I was going to discourage her from sitting in my lap.
Jenny sat with her back against the door and sort of sideways on my lap facing Zoey. I did not know where to put my hands – I had one behind her and the other awkwardly resting on her flat stomach. I think she had one arm over my shoulders.
Alex was doing the annoying teenage boy thing of driving like a maniac on windy country roads to impress everyone. That gave me an excuse to hold Jenny a little tighter sometimes. I am sure we were listening to loud music, singing along and Joe and Zoey were pretty funny, so I imagine they were amusing everyone.
I don’t really remember those details of what we were talking about or what music we listened to. I just remember that night was really a perfect teenage night. Cruising around with my crush in my lap and my good friends with no real destination. Jenny and I had our faces pretty close together due to the seating arrangement. And I remember looking at her face a lot and sometimes we looked each other in the eyes and smiled. Sometimes we looked at each other more furtively. If we had been alone in that backseat we definitely would have kissed.
It was a warm night and Jenny was wearing a tank top and some stretchy shorts made out of some thin material like Lycra. I was wearing shorts and a tshirt. This was probably the first time I had any kind of physical contact with Jenny. With only some thin material between us and the movement of the car, I got a boner. Like a raging poke her in the ass boner. Jenny did not say anything or try to get off my lap.
I remember that it turned me on to have my hand on her stomach. And with her stretchy shorts, I think I was enjoying looking at her thin legs, up to her thighs and seeing her crotch was right there, really my hand was only a few inches above her pubic area. She also had a cute little bit of camel toe in those shorts. And her small tits were just a few inches above my hand. And my other had behind her was sort of resting behind her on her hip, which was perilously close to her ass.
All that combined with the fact that I could feel her ass on my dick, gave me that crazy boner. It is probably lucky the ride was not much longer or I might have cum in my shorts. Eventually, we stopped and got out of the car back at school and I had to sort of hide my boner until it went down or I went home.
A couple of days later, I was out in the parking lot after school, talking to Kim. She said, “Jenny told me you had a boner when she sat on your lap Saturday night” with sort of a smug look on her face. (As an aside, I have spoken with Jenny about this recently and she remembers that I had a boner. She said she remembers feeling surprised and could not understand why I was that attracted to her. She was self conscious about her looks back then even though she was definitely hot.) I was super embarrassed, when Kim mentioned the boner.
I immediately denied it, “I did not.” “Jenny said she definitely felt a boner”, said Kim. I stammered, “Well I didn’t.” I am sure I was bright red having this older girl making fun of me for getting a boner from my crush. Finally, I guess she felt bad, and said, “It’s nothing to be embarrassed about. Jenny didn’t mind that you had a boner. She was flattered.” I think the conversation about my boner was mercifully ended by someone else walking up.
Source: reddit.com/r/Erotica/comments/qy90fg/an_awkward_boner_with_my_high_school_gf_jenny