This is another in a series of stories about my high school gf Jenny. For those that have not read them, Jenny and I dated for most of high school and for a little while after I left for college. To describe Jenny; she was petite, thin, with short reddish brown hair, small tits and a nice ass. She was very cute. These stories happened a long time ago, so they have been written in no order and sometimes I have had to fill in some dialogue but they are, for the most part, non fiction.
Sometimes Jenny wore lipstick and I have a few sort of funny/fond memories of her giving me lipstick kisses. This story involves a couple of SFW events and one NSFW event. The first time was very cute. We had really just sort of become a couple toward the end of the school year. I think we had been on only one date at this point and we had kissed. She was a freshman and I was a sophomore. I was sad to be leaving her right after we had finally started dating.
I was leaving for the summer to go work at a summer camp several hours away. I really wanted to see Jenny one last time before I left for the summer. This was pre-cellphone, pre digital camera days and people forget that there were just a lot fewer pictures those days. I did not have a single picture of Jenny, so I literally wanted a chance to see her face one more time before I left.
The day before I left, I needed to buy toothpaste. Jenny worked part time at a drug store about 20 or 30 minutes from my house. I took a chance that she would be working and drove to the store where she worked. I saw her and got in line at her cash register. She looked cute in her blue work apron and was surprised to see me in her line. It was pretty busy with lots of people around, so I just had time to hand her a note with the address of the camp and ask her to write me a letter. I could tell the older lady behind me in line thought that was adorable.
One day while I was working at camp, a letter arrived from Jenny. I went back to the privacy of my tent, where my friends would not be nosy about my letter from a girl back home. My tent was a big, old army style canvas tent with a wooden platform. I had a cot, a beat up old dresser, and a scrap of carpet on the floor. I lit it up with candles at night to save my batteries for listening to music. It was slightly rainy and the tent was pretty cozy. I liked the sound of the rain on the tent and the leaves and the smell of the damp forest.
I opened the letter and I don’t remember much of what it said other than, “what’s up, I miss you…Love, Jenny.” But, the best part was she put on lipstick and pressed her lips to the letter, leaving a perfect lipstick image of her lips. She told me years later that she remembered being nervous doing that. She thought I might find it weird. I did not find it weird. I would pull that letter out repeatedly all summer and I liked to see her handwriting, her name and that kiss. Then I would put out the candles, get in my cot and jerk off till I fell asleep imagining us doing things we had not yet done.
The second lipstick kiss story happened after school one day. I was driving around the back of the school and happened to see Jenny come out the back door. She was wearing her school uniform. I thought she looked hot in her uniform with the white button down shirt tucked into her plaid skirt showing off her thin waist. I think she had an extra button unbuttoned, sleeves rolled up because it was hot out and her plaid skirt, hemmed just above her knees. She was about to walk to meet some friends.
I had my window rolled down and I beckoned her over to me. She walked over to my car and leaned on the frame of the door and we chatted. She did not realize I could look down her shirt and see her white bra as she bent down to my car window. She would have been embarrassed because she was shy about her small tits, but even just that glimpse turned me on. She leaned further into the car and we kissed, then we said goodbye and she started walking and I was going to drive home.
As I left the school lot, I thought to myself, “I need to kiss her some more.” So I drove my car down to where she was meeting friends. Our friends left us alone and lwe stood there hugging and kissing. I moved my hands down to feel her ass and I could feel the outline of her panties through the polyester plaid skirt. And I moved my hand further to feel where her ass cheeks met, which felt even naughtier. Our friends came back and we stopped. Someone pointed out that I had lipstick around my mouth. Jenny and I were both embarrassed and I had to leave to get home.
When I got home, I looked in the mirror and saw the lipstick on my upper lip and some on my lower lip. I liked looking at it there because it reminded me of kissing Jenny. So, I left it there and went to look at it in the mirror occasionally until I heard the garage door opening when my mom got home from work. Then I wiped it off.
The final part of this lipstick story is NSFW. This was months later and Jenny and I had started having sex. I would drive her home from school sometimes when her dad was working 2nd shift. So, we could hang out at her house alone after school.
I think this particular day may have been one of the first times we fooled around after school at her dad’s house. It felt good to walk out to my car with this cute girl and leave school on our own. As I drove her home, I liked looking over at pretty face and down at her bare legs as her uniform skirt was just above her knees.
We went in her house and sat next to each other on the couch in her living room. We started kissing and pretty soon my hand was on her bare knee. I slowly moved it up her inner thigh under her skirt and she spread her thin legs slightly so I could rub her pussy through her underwear. Then I moved up the front of her skirt with my hand, so I could see her underwear and put my hand down the front of her panties to finger her.
Her dog was too interested in what was going on, so we put him in a crate there in the living room. Then I unzipped my pants and pulled them and my underwear down and sat down with my dick standing straight up. Jenny grabbed my boner and started stroking it. Her dog was watching and barking at us.
I said, “Will you suck my dick?” She leaned over, put it in her mouth and started sucking my dick. She had done that a few times before this day and I have to say the practice was paying off. She did not go deep, but it felt really good. I was ridiculously hard and she knew how to make me feel good with her lips and hand.
The dog really did not seem to like the blowjob. I was watching her head bob up and down on my dick and sort of pulling up her uniform skirt, feeling the skin of her hip and butt. She paused from sucking me to tell the dog to shut up, then continued. I made a bad joke/stupid comment, “He is just jealous, he wants a blowjob.” Jenny paused and said, “that’s disgusting” and blew me a bit longer.
She did not want cum in her mouth, so she stopped sucking and we went back to fingering and handjob. Eventually she made me cum with her hand. We cleaned up and then I needed to race to get home before my mom. We kissed goodbye in her doorway and she stood there waving at me as I drove away.
When I got home, I went to use the bathroom. I looked down and saw something on my penis. I panicked thinking it was some kind of injury like an abrasion. Then, as I looked at it, it dawned on me that it was Jenny’s lipstick. Just a couple of little faint smeared red marks on the shaft and tip of my dick. It’s hard to describe how much that turned me on. It was just such a visual reminder that her lips really had been wrapped around my dick about 30 mins before. I had to jerk off while looking down at the lipstick on my cock and then I reluctantly cleaned it off.
Source: reddit.com/r/Erotica/comments/rl2e5u/jenny_my_high_school_girlfriend_leaves_her_mark