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.
There was a dance at my high school on a Saturday night. It was a casual one, so we were all wearing jeans or something along those lines. It was pretty boring like most school dances, so a bunch of us decided to leave. We were just going to go hang out in the dark, behind this warehouse.
I was driving my friend Adam in my car the short drive from the school lot to this warehouse. We were meeting some girls there including Jenny. Adam was planning to get a blowjob from this girl that was meeting us there. They had fooled around some before, but were not really dating.
Adam was talking about how this girl had sucked his dick before and said, “Does Jenny give you blowjobs?” I said, “None of your fucking business, that’s my girl.” He was lucky I didn’t punch him in the face. I guess it just made me angry that people might talk about Jenny behind her back and whether she did or did not give me blowjobs. He said, “Sorry man, I didn’t mean anything.”
When we got there, this girl was indeed waiting for Adam, and I vaguely remember some discussion in front of everyone that she had a thong on for him. Then they went off into the woods and we all knew they were marching off into the woods, so she could give him a blowjob, which is sort of weird in retrospect.
Some other people were walking to a convenience store. That left Jenny, her friend Rachel, and me. Rachel sat down on some wooden pallets and said to Jenny and me, “I’ve seen it all, so you guys feel free to do whatever you want.” Kind of hilarious for her to say that. Not sure what she thought we were going to do or what she had seen. I sat on a different stack of pallets a little further down from Rachel. Jenny came and sat between my legs leaning her back into my chest as I leaned against the wall of the warehouse.
It was chilly out, so I had Jenny wrapped inside my oversized coat with me. I remember feeling my lips touch her left ear as she leaned into me. I liked the feeling of the soft skin on her ear and sort of purposely positioned my lips to be grazing her ear. I used my hand to turn her face to me so I could kiss her. She was wearing hoop earrings and my thumb tangled up in one as I moved her face and kissed her. We just snuggled and kissed until everyone came back. Don’t know if Rachel was disappointed or relieved that we didn’t do anything beyond kissing, but it did not seem like the time or place to start fooling around and I was perfectly satisfied with what we were doing.
It was kind of funny that Rachel just sat there alone on some pallets while Jenny and I kissed, Adam came back with a shit eating grin after getting blown, the girl who blew him seemed pleased with herself, and the others came back from the convenience store. Some of my other friends came to find me to go to a friends house. Right now, some of you guys wish you were Adam getting a blowjob, but you should be envious of me that night, because the girl I was kissing was special to me. If you don’t get that, you’ve never been in love. I have had blowjobs from random girls (which is fun) and I would take kissing a real crush every single time over that.
Jenny’s dad was going to pick her up soon and we had a passionate embrace and kiss goodbye in front of everyone and then I went off with my friends. When We kissed, I felt like everyone was just kind of watching us and wished they had the same thing. I can still picture walking across this dark field with my friends after kissing Jenny goodbye and I think she was watching me walk away and one of my friends actually said to me, “I wish I had a girlfriend like yours.”
It was a little after this that we actually had our first sexual foray. And I am not going to claim it was any classier than wandering off into the woods behind a warehouse. We were on a bus trip, so it was not exactly a private location. Before we got on the bus, Jenny and I were talking outside. I was leaned against my car and she was leaning on me, facing me and hugging me. Jenny said, “Do you want to see my underwear?”, with a mischievous grin. This actually became Jenny’s standard move, but this was the first time. She would initiate things by showing me her underwear. I loved it every time.) I eagerly said, “Yes.” She moved away from me slightly, looked around and then pulled her stretchy pants away from her waist so I could look down and see her panties. She put her pants back in place. I grabbed the waistband and pulled her pants away from her body for a quick second look. She giggled.
Once we were seated on the bus, we started making out as usual. I felt like showing me her underwear was her signal to me that she was ready for more than kissing. I moved a hand up to her chest to cup one of her tits on the outside of her shirt. She said, “Don’t touch my boobs, they’re small and it’s embarrassing.” I said, “I like them.” Jenny said, “You can touch me anywhere else, just not my boobs.” Anywhere else sounded interesting.
I started feeling Jenny’s ass on the outside of her shorts. Then I just decided to go for it and slide my hand down the back of her shorts and inside her underwear, so that I was touching her bare ass cheek. I had felt her ass before then outside of her clothes, but having my hand in her underwear was exciting. She did not seem to mind that I had my hand on her bare ass, so I decided to move my hand around to the front of her shorts.
I slowly slid my hand under the waistband of her shorts and then moved my hand further down until I slid under the waistband of the front of her panties. As I moved lower, I felt bush. I was pretty fucking excited to just be touching bush honestly. I kind of awkwardly touched her labia and could not really figure out how to get a finger in her.
She put her hand up the leg of my shorts and just kind of held my boner, which was both awkward and very exciting. It was like an electric shock to my dick to finally feel the soft skin of a girl’s hand on the sensitive skin of my boner. Even though she was not stroking it, It was pretty thrilling. This was a fairly short bus ride, so we pulled into the school parking lot and the lights came on and we had to stop touching each other.
We had another bus ride the next weekend. This was a bit of a longer ride. My mom and her dad were both chaperones on this trip which makes this all funnier to me. They were sitting up front. And it was daylight as we rode to a football game.
Jenny said, “you would like my underwear” and she pulled down the side of her pants and used her thumb to pull the side waistband of her string bikini underwear out to show me. Seeing the bare skin of her hip and that thin string of her underwear – it was probably a good thing I was sitting down or I might have passed out from the blood rushing to my dick.
We started kissing and eventually I went for it again and put my hand down the front of her pants and into her panties. We were using my coat like a blanket even though it was not cold out. This time I had more time and I figured out how to get my finger inside her. I think a lot of guys have had this first experience, but it was lower than I expected. It felt even nicer than I expected. Very silky soft, warm, and wet. She was burying her face in my chest so people would not see her expressions.
She was kind of groping my dick on the outside of my pants. I unzipped my pants and pulled my very hard dick out. She wrapped her thin fingers around it and started slowly stroking it. It was actually hard to believe it was her first time giving a handjob because it felt amazing.
We spent that entire bus trip with me fingering her and her stroking my dick. Eventually, my dick started twitching and she pumped out a load of cum right there. That was the first time a girl (or anyone other than myself) made me cum. I had to just kind of put it back in my pants and zip up with a load of cum in pants.
Pretty soon after, we arrived at our destination. As we were getting off the bus, she gave me a bit of a funny smile, pleased with herself that she had successfully made me cum. She told me years later that she felt really powerful making me cum that day. I did not give a shit that I had a load of cum in my pants. I think I was walking with a little more swagger that evening.
We sat in the football stands right next to each other, behind her dad and my mom and the other chaperones. Jenny was very sweet and innocent talking with my mom – she did not seem at all like the kind of girl that would jerk off your precious son to completion behind your back on the bus. I am sure I acted appropriately terrified of her dad. Actually it was not an act, dude had arms as big as my waist.
Source: reddit.com/r/Erotica/comments/rfi7li/the_first_time_my_high_school_gf_jenny_made_me
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