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.
I drove up to my old high school and got in the pick up line. I saw Jenny standing there. She was wearing the school uniform with stereotypical plaid skirt, white button down shirt and a sweater. Jenny was petite and thin, she had short reddish brown hair, brown eyes, small tits and a nice ass. She was very cute. I am not sure why I thought it would be a good idea to surprise her, because she would have already had a way home.
As soon as I drove up, I saw her face and I knew we were breaking up. She had an irritated look on her face when she saw me. I felt like throwing up. In all the time I had known Jenny, she had never looked at me like that. Normally, she would be running and jumping on me or looking very happy to see me. I wished I could just drive away and pretend like I had not come there.
Jenny got in my car and I think there was a curt hello. As we drove to her mom’s house, Jenny said, “you should not have come to pick me up.” I said, “Sorry, it was a bad idea.” I don’t think we talked much on the drive. I pulled up in front of her mom’s house and parked.
Then, Jenny said, “I think we should see other people.” And I knew she was right, the long distance thing was not working great and I did not have some alternative idea. So, I said, “Okay.” Then, I said, “Can I have a kiss goodbye?” I think I just knew it would be the last time we would kiss and I also thought that it might stop me from crying in front of Jenny. So we kissed and i think i still had a little bit of tears welling up but at least I did not break down sobbing.
Then Jenny said, “I don’t have the key to my house, let me see if I am locked out before you leave.” She went up to her house and checked the doors. She came back to my car and said, “I can get in the basement door, but it is creepy down there , so you have to come with me.”
I followed Jenny around the back of her house and then we went in the basement. The basement was unfinished, with concrete floors. There were boxes and old furniture everywhere. We made our way to the basement steps that led up to the first floor.
“Thanks for walking me in, this basement is scary”, Jenny said. I said, “Are you scared a bad guy will be down here waiting for you?” Jenny said, “yes, like some perv” “Well you are down here with a perv now”, I said. She laughed and said, “Yes, but you are a perv who will do whatever I ask.”
“I don’t know about that anymore, you just broke up with me”, I said. “I don’t think you can blame me for that mister moved to another state and also I know you would still do whatever I say”, Jenny said. “You’re so sure?”, I said. Jenny said, “You were just tearing up out there – you still love me.” “First of all, there was a lot of pollen in the air, second…”, I said. Jenny said, “you trailed off there.” “Okay fine, but you still love me too”, I said. “Yes, but my point stands that even though we are broken up, you will do whatever I ask”, Jenny said. “Try me”, I said.
“Take off your clothes”, Jenny said with a naughty grin. So I pulled off my t shirt, took off my boots, my jeans and finally my boxers. I was standing there naked with an erection down in her creepy basement. I started moving towards her, but Jenny said, “Stay where you are and keep your hands to yourself.” I never had a problem being naked in front of people, particularly Jenny, but i have to admit it was a little humiliating standing there totally naked with a growing boner in front of her with her just looking at me.
Jenny said, “Have you been putting that thing in any little rich bitches up at school?” “No, you were my girlfriend until about 5mins ago.”, I said. “Okay, good boy” “What about you?”, I said. “No I have not been putting my dick in any rich bitches”, said Jenny laughing. “Seriously, no I have not been with any other boys. So, do you just play with yourself and think about me?”, Jenny said. “Yes.” Then, she said, “Show me.” I said, “what?” Jenny said, “Show me how you jerk off thinking about me.” So, I started stroking my dick in front of her, which seemed weird. She looked at me lustily, but then said, “stop touching yourself.” I was dying for her to touch my dick and she knew it.
“Come upstairs with me”, she said. So I grabbed my clothes and followed her up the stairs naked. We got to her bedroom and she said, “Okay, mr smarty pants college boy, I have some hard math homework. My mom gets home in 2 hours. You help me finish my math homework and whatever time is left we can do whatever you want.”
I said, “Whatever I want?” She said, “You know my limits and also this does not mean we are getting back together.” “Well your math homework is going to be easy for me, so I am definitely in”, I said. I started to put my clothes back on to sit down and do her homework.
Jenny said, “No, you are going to be my naked math tutor.” I sat down on her bed with her math homework. It was odd sitting there with a boner and trying to look at the math problems. Jenny was digging around in her dresser.
She said, “I am wearing boring underwear because I didn’t expect to be fooling around today. Should I wear these?” As she held up a cute pair of string bikini style panties. She was not making it easy for me to finish the math. “Those are nice” I said trying to ignore her. “Or maybe I should wear these?” as she held up some with a see through mesh front. “How am I supposed to finish this math?”, I said. Jenny said, “don’t know, just do it.”
She left the room to go to the bathroom and change underwear. I made some
progress while she was gone. She came back and sat next to me on the bed. I tried to ignore her. “Watcha doin?”, Jenny said and she grabbed my boner and just kind of held it. She gave it a couple of slow strokes. I sort of groaned, “Hand me your calculator.” She let go of my dick to hand me a calculator. “This distraction is not going to work. I’m going to finish this homework and then you are in trouble.”
I was sitting crosslegged and she laid down with her head in my lap looking up at me and said, “I’m just helping.” My boner was right by her face as she looked up at me innocently with her brown eyes. I just reached over her head to continue the math homework. She started occasionally licking my penis. “Oh my god, please just put it in your mouth and suck it for a minute”, I said. “No, you’re not done” she said with an impish smile. Then she sort of started pulling my dick down and then letting it spring back up and giggling. “Must you?”, I said. She moved her head out of my lap and sat with her feet in my lap gently tapping my boner back and forth with her feet and she moved her skirt up and spread her legs a bit so I could see the crotch of her underwear.
Finally, after about 30 mins of this teasing, I finished the last math problem. “I’m done, so I hope your ready for 90minutes of getting fucked”, I said. “No offense, but I don’t think you can last anywhere near that long”, Jenny said getting up off the bed. “You said I have until your mom comes home. You did not say how many times. I’m 19 and horny, I can get boners all day”, I said. “Okay a deal is deal, what do you want to do?”, Jenny said.
“For starters, I need to see that underwear you decided to put on”, I said. She started to take off her skirt, but I said,
“No leave that on, this is probably the last time I get to fuck a Catholic high school girl in her uniform.” “Perv”, Jenny said. She lifted her plaid skirt to reveal that she had put on some cute bikini cut panties with black and red horizontal stripes. I sat on the edge of her bed and said, “Suck my dick.” She got on her knees in front of me and put my dick in her mouth and started bobbing her head up and down. “Fuck that feels good”, I said. She giggled and then continued slurping.
“Okay, stop”, I said weakly. I knew she did not want cum in her mouth and I did not want to cum yet anyway. “Go bend over that desk”, I said. “Now lift your skirt for me”, I said. She lifted the back of her skirt to show me her panty covered ass. I pulled down her panties slightly so I could smack her bare ass. What is this for?” Jenny said. “Breaking up with me and then teasing me for 30mins”, I said. “You loved it….well not the breaking up, but the teasing”, she said. I smacked her ass a few more times and rubbed between her legs a bit.
I pulled her panties back up and told her to lay on her bed. I laid down next to her hugging and kissing her. Then I unbuttoned her white school blouse all the way down revealing her little tits in a cute bra. I kissed my way down her flat stomach and then moved down to her legs, lifting her skirt. She looked a little red and nervous as I spread her legs and kissed her inner thighs.
Then I kissed her crotch on the outside of her panties, as she looked nervously down at me. She had always been shy about getting her pussy licked. I said, “is this okay?” She just nodded yes while biting her pouty lower lip. I pulled aside the crotch of her panties and gave a lick.
I pulled her underwear completely off. She had a nice pussy with a neatly trimmed dark bush. She was red faced and breathing a bit heavier. I went back down to her crotch and licked some more. I said, “Every time I saw you in this skirt, I imagined doing this – you taste so good”and I continued licking. She just kind of whimpered a bit as I licked her.
I finally had to fuck her. I slid my dick between her legs and into her now very wet pussy from my saliva and her own wetness. I really was not able to take my time or go slowly, because I just really needed to cum, so I just banged her quickly. She tightly wrapped her legs around me. I probably did not last more than a couple of minutes from all of that build up, then I pulled out and jerked off shooting cum up her flat stomach and some got on her skirt. Then I rolled off her and laid next to her with both of us breathing heavy.
My dick was still quite hard. She got up and went to the bathroom to wipe the cum off her. When she came back, I said, “Take your clothes off, we still have plenty of time.” She slid off her skirt and her shirt. I could see her perfect little triangle of trimmed bush. Then she climbed on top of me in only her bra (she was still a bit shy about her little tits) and started kissing me and grinding on my dick. “Suck it some more”, I said. Jenny slid down and started sucking and using her hands on my dick.
I said, “Now fuck me.” She moved up my body and straddled me, grabbing my dick and putting it in her very wet pussy. She started riding up and down on my dick. Now that I had already cum,
I could last awhile, so Jenny rode me and she leaned forward and put her hands on the bed and I was also thrusting upward into her. I could feel her tight pussy clamp down on my dick.
I pulled down the straps on her bra to reveal her nipples and pinched them lightly. I moved my head up to bite and suck on them a bit as she fucked me. She was orgasming now with my dick fully in her but grinding her hips back and forth. I told her I was going to cum and she just kept going until I came inside her. She collapsed on me with my dick still inside her. We kissed some more.
She rolled off me. I said, “we still have time left”. She started stroking semi hard dick and playing with my balls. I was running my hand up and down her naked body. My dick got hard again and I lifted her leg closest to me and slid my dick in her so that I could just fuck her really deep sideways. I pulled out and switched to fucking her missionary. I fucked her for a long time and we were both a little sweaty and we made a wet mess on her comforter.
We finished and laid there a bit. Jenny said, “if you were here, we would not be breaking up right now, but I know you have to go to college. I just can’t wait around for four years.” “I know”, I said. Then, we heard a car door. “Fuck, you have to get out of here”, Jenny said, “Go out the basement!” I started getting dressed. Jenny said, “No time, just go to the basement!” I grabbed my clothes and ran to down the steps. I got dressed quickly in the basement and then ran out to my car. Jenny’s mom was just walking in the door as I hopped in my car to leave. I think I cried like a little bitch on the way home.
Source: reddit.com/r/Erotica/comments/r825a2/jenny_my_high_school_gf_and_i_break_up_after_i
Got to watch out for those named Jenny.