This story is somewhat related to this story from before: https://www.reddit.com/r/prematurestories/s/weBBL9kobX

Jessica, is the girl I lost my virginity too. Her friend Katie was my dream girl who slept with me twice for a total of 10 seconds, laughed at my cock, and then never talked to me again. Fast forward a little bit, and the holidays are here. Everyone is back in our hometown. I get a Snapchat from Jessica. She and I hadn’t spoke in years. Last I’d heard she was married, and I didn’t even realize she was still on my friends list.

We chat a little bit about old times. She and I lost our virginities to each other around 15-16 years old. We’d dated the year before, but she’d dumped me and was seeing this guy named Zach on and off. I’d always wondered why she picked me to lose her virginity too, but I never complained. We’d had sex 3 times, and ironically even though I bust from a slight breeze now, I never came from the sex we had in high school.

Anyway, she’s just visiting but says it would be fun to get together again and catch up. She said it would be fine to just meet at my place. We text a little bit through the week, but the morning of our date she is HORNY. She’s talking about how bad she needs to be railed and how she’s always been sad she didn’t make me cum and how she wants to make it right.

Needless to say, she walked through my door when the date finally happened and we instantly started making out. She and I are pulling each others clothes off all the way to the couch. She’s so excited she can’t even make it to the bedroom. I’m sitting on the couch with her straddling me. Precum is pouring out of me and leaking through my underwear. We are both down to our undies.

She stands up and strips for me. She grabs a condom from the drawer next to the couch as I pull my underwear off. If she’s bummed about my tiny cock she hides it well. She slowly slide the condom down on my cock. Which I think I’ve only had a girl do a few times, but I almost blew my load right then and there.

“Look how fucking horny you make me baby” she moaned as she straddled me again. She took my hand and rubbed it against her pussy. She was leaking like a faucet.

She leaned down and kissed me. With one hand she held my face. With the other she guided my cock into her wet pussy. I moaned into her kiss as I felt her wrap around me. Once I got all 3.5” into her, she reached back and started massaging my balls. I’d never had this before and I had no idea how sensitive they were when rubbed like that.

Jessica sat there with my cock inside of her for about 20 seconds. She didn’t even start moving. Just rolled my balls in the palm of her hand. “Jess. Jessica. Stop. I can’t handle that” I moaned grasping at her ass and the couch. “Jess I’m gonna cum if you don’t…” but as usual it was too late.

My cock began to pulsate inside of her. “Mmm you love it don’t you” she moaned as she rubbed my balls. I came insanely hard and then leaned back. “I’m sor…” I stared my usual excuse before she stopped me.

“Don’t even tell me this never happens. Katie warned me” she giggled. I looked at her confused. “I talked to katie like right after y’all hooked up. I just didn’t believe her and had to see for myself” she said standing up.

She quickly started getting dressed while I sat there the condom still on my cock. “So?” I asked.

“So, she was right. You haven’t changed a bit since high school” she chuckled a bit and gave the little signal with her fingers. “But it always bummed me out I couldn’t make you finish. Mission accomplished”

“So you just did this as like a challenge to yourself?” I sat there in disbelief. “I mean to be fair it’s not like the first time we slept together it was much more” she said.

“Yeah, why did we hookup in high school? I’ve always wondered…” I said as I stood up and pulled the condom off my flaccid cock that had shriveled up already.

“Because of that” she said pointing to my cock. “I tried to fuck Zach, but he wouldn’t fit. I knew you had a small cock so I figured you could loosen me up for him. And boy did it work” she said grinning as she finished getting dressed.

“Anywho, I’m off to meet the softball girlies. Don’t worry, I’ll be sure not to tell them every detail about this” she said giggling as she let herself out.