I have a few stories from my youth. I’ve enjoyed reading the stories posted here and can only lurk for so long before I gotta give back to the community. I’ll give you some set up and then sexy parts. I will be retelling these as accurately as I remember… there may be some gaps and there may be some unsexy parts. Just a heads up. Also fair warning, I used to think I was a writer.
Story #1 is about 15 years ago.
I worked with Claire at our part-time job; she was working while finishing her senior year of High school, and I was just working there while I wasted my 20s partying and hooking up.
WARNING this story includes cheating.
At the time, we were both in relationships with other people. This was not the first time we’d hooked up; we’d tried dating earlier in the year but it didn’t work out and we’d since set up a pretty beneficial friendship. In retrospect, she was crazy about me and I did not treat her as well as she deserved.
It had been a couple weeks since we had a chance to see each other, I texted her to tell her that I was going to be at the school to pick her up for lunch (part of our arrangement) in 10 minutes, and I wanted her panties off before she got into my car.
I parked and waited. When the double doors opened and she came out. She was a beautiful girl. 5’7”, 110 lbs. D’s. Think a taller April O’Neil (from early in her career). Pin-straight light brown hair. Her uniform shirt was still tucked in and her kilt was probably 3-4 inches too short for her long, smooth, slender legs. Then beside her I noticed her boyfriend.
I almost felt bad for what I was gonna do.
My dick was already half hard, watching her kiss him and leave him on the steps and walk to my car. I leaned over and opened the door from the inside. She slid into the passenger seat and offered a very chaste “Hello,”
“Hey, what did you tell him?
“You’re my tutor. My English mark is low.”
“Oh, ok. Wave goodbye, then.” I couldn’t wait to get my hands on her, but I took it slow driving to her home, as we knew her mother was at work.
As we left the main roads and into the quieter area near her house, I reached over and grabbed the front of her kilt and flipped it up. Tiny pink panties. I looked at her and raised an eyebrow.
“I thought I said to lose these?”
“I know, but I couldn’t. there wasn’t time and I have to do something when we get home.” She fixed her kilt.
“Oh, ok… but…” I flipped her kilt back up and spread her legs as wide as she could go in the seat, “Leave this.” I rubbed the inside of her thigh and her pussy over her panties, but she wouldn’t let me get my fingers inside the waistband.
“Ok.” She bit her lip.
We arrived without further incident. She unlocked the door and we went inside. She walked me through down the hallway to her bedroom. She kissed me and stroked my cock over my pants and told me to wait.
After a while (I wasn’t counting and this was before smartphones) I got bored and went looking for her. I stepped out of her bedroom and had an unobstructed view into the bathroom. She was naked, standing near the sink with her leg up on the edge of the tub, and she was shaving her pussy lips.
One thing I loved about hooking up with Claire is that she always had her pussy shaved clean. I vaguely remembered her telling me she needed to grow it out a bit to get waxed but apparently she couldn’t wait any longer.
“Oh, hi.” I said
“Hey, sorry, I had to shave. It was driving me crazy.”
“No, it’s super hot. I know you’re doing it for yourself but it’s kinda like you’re doing it just for me.”
“Well, I’m not. This is for me” she said with a laugh.
I walked over to her as she put the razor down on the side of the tub. I walked over to her and grabbed her leg and put her foot back up on the side of the tub.
She put her arms around my neck as we kissed and I rand my hand over her smooth lips. I broke the kiss to smile at her, because she was soaked. Being caught like that must have been a thing for her. Beats me. I undid my belt and slid my pants down to my thighs.
Claire put her foot down and started to lower herself to suck me off. I stood her back up and put her foot back.
“Don’t move.”
I crouched down and reached under her leg and grabbed her ass. It was smooth, big enough for a skinny girl and soft. I leaned back and put my mouth on her pussy. I parted her lips with my tongue and felt around for her clit. I licked her a few times and felt her hands in my hair. She was moaning quietly… neither of us were really noisy during sex; a youth full of sneaky encounters conditioned us to be nearly mute.
I slid my hand up the outside of her thigh and grabbed her hip, and slid my other hand to her pussy. I pushed my index and middle fingers in to her warmth, and felt the slickness. I pulled my fingers out and made sure she was wet and ready.
I stood, dropping my pants and boxers. I grabbed my cock by the base and bent my knees to get access to her pussy. Claire leaned back to help and I supported her weight with my other hand around on the small of her back.
As I parted her pussy with my tip, I nearly lost control. The girl, situation and tension AND time since our last time was all very, very hot.
I basically slammed my whole cock home in one hard thrust.
I don’t really know how to describe the sound she made, but it was part exclamation, part moan and part sexy grunt.
I grabbed her other hip and picked her up, fucking her as I moved her across the bathroom, putting her down on the counter. Her head was against the mirror and with every few thrusts, she was bonking her head on the glass.
I was not so far gone to not notice the obvious discomfort this was causing. I gathered her up in my arms, hugging her close.
With my dick still rock hard inside her and my pants around my ankles, I shufflefucked my way back to her bedroom.
I tossed her onto her bed, stepped out of my pants and tossed my shirt off, and went to climb onto her. She stopped me with a hand on my chest. She sat up, turned around and got up on her knees presenting her ass and pussy to me. She looked back over her shoulder at me with the same style of sexy lip bite from the car earlier (I would learn this is her signature move, so much so that it’s an indelible memory 15 years later)
I spread my knees outside of hers on the bed and lined myself up. It was always a pleasure sliding into her, she was always so smooth and tight. Tighter, even, when I grabbed her head and pushed her face into the bed. I entered her slowly this time with a long, low groan.
I rolled my hand up in her hair and pulled her back up as I fucked her. I wasn’t merciless, but damn near.
I grabbed her tits with my other hand as I held her hair like reins and slammed my hips into her ass.
I knew I wasn’t going to last long, so I went as hard as I could until I couldn’t any longer. I slammed my cock home and unloaded into her drenched teen pussy.
I barely had the chance to sit back on my heels before Claire *spun* on her knees to take my spent cock in her mouth, sucking and licking our mixed fluids off my dick. It was WAY too much. I almost jumped off the bed
“What are you… wow. That was too much. It’s too sensitive.”
“Oh, I was just cleaning you off. I like it.”
“no, it was awesome, just too much.”
“ok. Come back to bed?”
“Yeah… I just gotta,” I pointed towards the bathroom.
I didn’t really have to do anything. I just had that post-nut clarity and was feeling guilty for what I had done. As I stepped into the bathroom, I noticed something under the edge of the cabinet.
My wallet. It must’ve fallen out of my pocked while I shuffled out.
My mind started to spin. What if we’d left right afterwards, like we had in the past? I’d have left it there to be found by her mom. Then we’d be busted. What if we got pulled over on the way back, and I didn’t have my licence? Too many negative potential outcomes.
I wandered out into the living room naked and sat on the couch.
I guess I was staring out into the abyss for too long, because Claire came out looking for me.
“What are you doing out here?”
“I don’t know, Claire! What are we doing with all of this? I just feel. . . guilty.”
“We are just having fun. That’s all.” I know now that that’s not all it was to her, but that’s what she thought I wanted to hear at the time.
“I know. It is fun, you’re a lot of fun… but I’m not sure it’s worth the stress.”
“If you think so,” she said, her eyes downcast, still standing in the doorway.
Now I felt bad that we’d fucked and then I basically said I wanted to call it all off, “Come sit, and let’s talk about it.”
Claire came over and sat down *on the floor at my feet!* If I could reach back in time and kick myself, I would. How more obvious could she have been?
“Get up, sit with me on the couch.”
Wordlessly, she stood. Then, instead of sitting beside me, she threw her left leg over and straddled me. I could feel the heat of her pussy on my cock, which went from sad and flaccid to half mast in milliseconds. she slowly started rocking on it, sliding her wetness down my shaft… making it very difficult to concentrate on what I was trying to say.
“the way we’re acting, its unfair to Laura, and it’s unfair to Will.”
“Uh huh” she said, sliding faster as she became wetter
“We’re being monsters. We could really hurt them.”
“Uh huh” she replied, lifting herself up and slowly impaling herself on my now rock-hard cock.
“We could do… uhh… be… better?”
“Uh huh.” She was now bouncing with abandon, her goal obvious: make me fill her with cum again before heading back to school.
And cum I did. And once again she hopped off and grabbed my cock, burying in her throat. Nearly to the hilt. I had to pull her face off me again with another admonishment about the sensitivity.
She just smiled and walked off to the bathroom to retrieve her clothes.
We got dressed and I drove her back; Her boyfriend met her outside so our goodbye was professional. A tutor and a student.
That was one of many illicit interactions with Claire.
More to come if interest dictates.
Source: reddit.com/r/gonewildstories/comments/gomr3o/wasted_my_20s_just_fornicatin