So, I’ve known Judy since high school. We were ‘going with’ each other, dating, seeing each other, hooking up, screwing around, FWB….whatever you want to call it in high school, college, post college and into our late twenties. Some of my earliest sexual memories are with her.
We didn’t really stop whatever it was that we were doing until she met they guy who eventually married her…which is unfortunate because we had one of those pacts that people have. The ones where they swear if they’re not married by X age, they’ll marry each other. Coulda Shoulda Woulda…
One of my favorite sexual memories of Judy was on a fall evening, I was home at my parents and so was she…I think we were seniors in college. We had been planning this meet up for a while. We went to dinner and then out to the bars. We’d planned on going back to her parents to screw around because they were supposed to be out all night at a party, but when we got there their car was in the drive and all the lights were on in the house.
We drove past her driveway slowly when she grabbed my hand and said: Stop and back up quietly. So, I did and came to a stop just before her driveway. She hopped out of my car and snuck around the side of her parents house and re-emerged with something under her arm. It was a blanket. She told me to head to her old elementary school which was just around the corner.
Once there we drove past it a few times to see if any cops were lurking in the parking lots…we lived in the suburbs and they were always looking for house parties or kids making out in parking lots…clearly they were bored. Sure that the coast was clear, I started my car into the back parking lot that was hidden behind the building and killed the engine.
I asked Judy what she had in mind…she lifted her butt up off the passenger seat, pulled her panties down from under her long wool skirt, tossed them at my face and said: let’s do it in my old school yard!
I didn’t need to be told twice. I grabbed the blanket for the back seat and off we went into the nearly pitch black night. There was no moon and no lights coming from the school building. We carefully felt our way out into the grassy playground yard behind her old elementary school and spread the blanket out. It was big enough to go under us and still wrap around us on top.
We immediately started making out. Tongues darting about each other’s mouths. Kisses and nibbles on each other’s necks. My hand quickly found her exposed pussy and thin wispy bush under her skirt and she had undone my pants and had a firm grasp on my hardening cock. I got her jacket undone and was working on her shirt buttons when she dove down on my cock.
Judy had started out not so hot in the art of the blow job. In high school, she’d once got so aggressive with her teeth that she’d scrapped the skin off strips of my cock….scans up and down my shaft, I couldn’t get an erection for over a week without horrible pain. Well, she’d definitely improved with age and practice. One of the things I loved about her was she would totally willingly blow me to orgasim and swallow every last drop without ever loosing suction on my cock.
But this night was not one of those nights. No, tonight we were going to fuck each other properly. She sucked my cock for a few minutes the slid off me and on to her back, spread her long legs and said: your turn. I pulled her skirt up onto her stomach and settled my face between her thighs and went to work on her pussy. Licking, sucking, tongue flicking, finger fucking until she grabbed my head and just nodded.
Without a word, I slid my torso up until my cock grazed against her pussy. She moaned lightly. I teased her pussy with the head of my cock. Gliding it up and down her now wet slit. She’d had enough and looked me deep in my eye and whispered in her slightly husky voice: fuck me now.
With that, I slid my cock in her pussy. It felt amazing to go from the chili of the evening air to the warm wet tight confines of Judy’s pussy. She grabbed my ass and pulled down to drive me deeper into her pussy with each thrust as we kissed deeply, both of us moaning in pleasure. We fucked in missionary for a bit, then we flipped around so she was on top facing me. I got the rest of her shirt opened and pushed her bra up on over the top of her magnificent d cups. I twisted and pinched her nipples that were now rock hard in the cool crisp autumn air. She squealed in delight.
Judy pulled the free end of the blanket over her shoulders to keep warm as she arched her head backwards and looked up at the stars in the sky as she bounced up and down on my cock. We were both in heaven. I went to flip her around again, but she said: no, I want to cum looking up at the stars like this. So we kept at it wit her on top, head and back arched backwards, fucking under the stars, me starting to work her clit.
I’m not sure how long it lasted but we both eventually grunted out: “I’m gonna cum” almost simultaneously. Her pussy gripped my cock in orgasmic convulsions as I pumped her full of my load while we both stared up at the stars. She collapsed down on my chest. We just laid there for I don’t know how long. She’d pulled the blanket over us and we almost fell asleep.
We both stared to get cold as we came down from our orgasams and got ourselves buttoned back up and headed to my car. I dropped her off at her parents house, she grabbed the blanket and bounded up the driveway with my cum dripping down her legs…she’d left her panties in my car. I’ve never asked if she’d left them on purpose or just forgot them. Whatever the reason, I kept them for years in the back of my dresser drawer as a reminder of that night.
I’ll have more stories about Judy, but this is one of my favorites.
Source: reddit.com/r/gonewildstories/comments/g1jvp1/a_blast_mf_that_spanned_a_good_part_of_my_past