For anyone who has not read one of my Jenny stories, Jenny was my gf for most of high school. We were each others first everything, although we did not really get sexual until our last year of school. These stories happened a long time ago, so I have kind of just posted them out of order as I remember them.
This is the story of how Jenny and I lost our virginity together.
Jenny and I went to a Catholic high school together, so Jenny wore the stereotypical plaid skirt and white button down shirt. I had to wear a jacket and tie. Jenny was petite, thin, with short reddish brown hair, brown eyes, a few freckles, small tits, and a nice ass. She was very cute.
One day at school, there was an announcement that there would be a half day on Friday. Also, the announcement said that if we donated $1 to some charity, we did not have to wear our uniforms that day. We could dress like normal people.
I think that Jenny and I both saw the potential for some alone time with this half day. When I saw Jenny after the announcement, I said, “We could hang out at my house after school on Friday. My parents will be at work until 5:30.” Jenny said, “My dad will be headed to work in the afternoon, so you can just drive me home afterward.” “I just need to get you home by 4:30ish, so I have plenty of time to get home before my mom”, I said.
Jenny said, “We could watch a movie at your house. My dad has Lethal Weapon 2 on VHS” (this happened a long time ago). I said, “Cool, bring that tape to school on Friday.”
Friday came around and I remember it being one of those absolutely pointless days of school. Between the half day, the excitement of not wearing uniforms, and i think there were some activities – no learning happened at school that day. I had borrowed a tshirt from my older brother and was wearing jeans. Jenny was wearing jeans and a casual button down blouse.
Finally, we got let out of school and Jenny and I walked out to my car in the parking lot. It was about 20minutes to my house from school. I remember it being a nice, bright, sunny Fall day, as we
drove along pretty country roads to my house out in the sticks.
When we got to my house, we sat on a bean bag chair snuggled up to each other in front of the TV and put in Lethal Weapon 2. Both of us had already seen it. We never discussed the possibility of fooling around or having sex that day, but we pretty much fooled around any time we had some privacy. Jenny and I had been escalating our sexual activities from long make out sessions, to groping over the clothes, to fingering, handjobs, and blowjobs. She would not let me eat her out, she was too shy for that. She liked to show me her underwear, but would not take them off. We had never discussed going all the way and I do not remember thinking we were going to do it that day.
I am not sure how far we made it into the movie before we started kissing. Probably not very far, because I pretty much always wanted to kiss Jenny. Kissing led to hands wandering and groping. I unzipped Jenny’s jeans and put my hand down the front of her panties. I unzipped my jeans and pulled my boner out and she started stroking it.
Jenny broke the kiss and said, “I have to go the bathroom.” She went to a bathroom off the TV room. While she was in there, I took off my pants and underwear completely , so when she came out, I was laying on the bean bag naked from the waist down, playing with my boner. She came out of the bathroom with her jeans pulled up, but the fly still wide open, which I thought was kind of hot.
She laid down next to me and we went back to me fingering her and her giving me a handjob. I started pulling down her jeans and she pushed them down below her knees. I unbuttoned her blouse all the way down. She was wearing a red and black bra, that was sort of sexy. I think she put that on for me, although she was shy about her small tits.
She rolled on top of me and we continued kissing. I was running my hands up the back of her unbuttoned shirt to feel the soft skin on her back and sides and down to her panties. My boner was sandwiched between us, she was grinding her crotch into my naked boner. I shoved my hands down into the back of her underwear onto her bare ass, pushing her underwear down as far as a I could.
Jenny briefly got off me and slid her jeans the rest of the way off. Then pulled her panties the rest of the way down her legs. I still have this mental image of her panties briefly stuck around her ankles and then her completely removing them. We had fooled around a lot before this day, but she had never taken off her underwear before.
She got back on top of me and we kissed some more. Now her mostly naked body was on me with her legs wrapped around me. I could feel my boner pressed into her bush as we sort of dry humped
each other. I was running my hands over her bare ass, sides, hips and up her back to her bra straps. I was enjoying the feeling of her soft, bare skin.
We ended up rolling around the floor touching each other. At one point, I remember laying on the floor and she was sort of sitting near me with her knees up facing me, so I had this really clear view of her pussy for the first time. I had no access to porn then, so I had seen some playboy magazines and that was about it. I sort of gently touched it and put a finger in her. She had neatly trimmed bush and nice labia, I thought it looked perfect.
I said, “Can I lick you?” Probably a couple of weeks before this, while fooling around in my car, I whispered in her ear, “I want to eat your pussy.” She said no to that. I really just wanted to dive in there with my tongue. In my teenager brain, I thought maybe “eat your pussy” sounded unappealing, so maybe “can I lick you?” would sound better. But she said, “No, that’s too embarrassing.”
At another point, she laid on the floor and I was sitting next to her. Her shirt was wide open, so she was pretty much naked except for her bra. She did not want me to see her small tits. I was running my hand down her flat stomach and between her thin legs, up and down her inner thighs. Her legs were slightly spread, so I could finger her. I was really taking in her naked body so I have a perfect image in my brain of her thin legs with a bit of neatly trimmed dark bush in the crotch, flat stomach leading up to her little bra covered tits. She was stroking my dick as I was looking down at her and touching her.
Even at that point, it had not occurred to me that we were going to try fucking. She ended up back on top of me some more, with my dick popping up between her legs, so the shaft was sort of rubbing her labia and the head was pointed up toward her ass. I liked how that felt with my boner sort of straining against her crotch, but she moved my dick back between us, so she was grinding on it, which also felt good.
This was kind of a long time of just enjoying each other’s naked bodies. Then I was on top of her. She was leaned back onto the bean bag chair. She had her legs spread and wrapped around me, so I really just needed to move my dick slightly lower and we would be fucking.
Only then, I thought, “I wonder how it would feel to just put it in there.” I was not thinking we would fuck, but just put it in for a minute. So, I positioned my very hard dick at her entrance and sort of started pushing it in. She made a little noise like it hurt. I looked at her and said, “Are you okay?” She said, “Yes”. So, I kept trying for a bit.
It never seemed like my dick got more than halfway in, but it was still pretty exciting to know my dick was in there partway. I pulled out because it seemed like it was painful for her and I did not want to hurt her. I was not sure if it counted as losing our virginity, but Jenny told me years later that it counted because she bled that day. I did not even know she bled at the time, so I guess it was not that much blood. When we talked about it years later, she joked that I had a “Lethal Weapon” that day.
After I pulled out, we continued kissing and fooling around. By now, I think we had spent pretty much all of the movie rolling around naked together and kissing. I laid on my back on the floor. Jenny had her head on my chest, stroking my dick. She moved her head down further and started sucking my dick with her head turned sideways. I actually think it may have been the second or third time she had ever sucked it. My dick was so hard and sensitive from all of the fooling around, I just remember her warm, wet mouth felt really good. She would pull her mouth off and alternate with her hand.
I could see the back of her head moving up and down as she sucked my dick and look over to see her bare ass off to the side of me. She stopped sucking me and moved her head back up to my chest. She seemed to be staring down at my dick as she stroked me briskly. I had a really intense orgasm after that long build up. I shot a big load of cum up onto my stomach and the tshirt I borrowed from my brother. My legs squirmed around uncontrollably as I came. She continued staring down at my dick as she slowly pumped out the last bit of cum. Then we kissed some more.
I got up to change shirts and clean the cum off my stomach. When I came back into the room, Jenny was standing there buttoning her shirt, still naked from the waist down. I could see her cute little butt at the bottom of her shirt. She turned her head and looked over at me with a funny smile – probably because I was naked from the waist down with my still swollen dick swinging around as I walked toward her. My jeans and underwear were still on the floor near her jeans and underwear. I came around the front of her to hug and kiss her some more. I was still naked from the waist down, so I remember feeling my semi hard dick rubbing on her as we stood there hugging and kissing. I really did not want it to end, but I needed to get her home.
We finished getting dressed and it was time for me to take her home. Looking at her clothed next to me, as we drove to her house, I could not believe we had just been naked together. Her hair was slightly messed up, her shirt was untucked and slightly disheveled, and her lips looked like she had been kissing me for 2 hours. It was probably a good thing her dad was not home when I dropped her off, because I think she looked exactly like a girl who had just spent a couple of hours rolling around half naked with her boyfriend. We got to her dad’s house and she kissed me goodbye and went inside.
When we talked about it years later, we were both glad we lost our virginity together that day. I think some people would think of it as awkward or remember it as not good sex, since we did not know what we were doing, but I don’t remember it seeming awkward at the time. It was really sweet. We were just enjoying exploring sex together.
Source: reddit.com/r/Erotica/comments/sh792l/my_high_school_gf_jenny_and_i_lose_our_virginity