When I was in highschool, I used to visit my brother in college a lot. He was a few hours drive away and I’d come up and party with him and his friends on the weekend.
The first time I did this, I don’t remember why, but I was going to be staying in his girlfriend’s dorm. I think he stayed there all the time anyway in her room. I remember his gf saying to me “one of the girls across the hall is gone for the weekend so you can sleep in her bed, her roomate Jen is really cool”.
I didn’t care, I was there to drink and (hopefully) hookup.
A little about me in highschool – i was tall and skinny and NOT all that successful with girls. I was on the basketball team and all my friends were hooking up every weekend, some had girlfriends, I would get lucky to have a sloppy drunken hookup every now and again. I was a virgin and hadn’t had a steady girlfriend.
I liked to drink because it gave me confidence to talk to girls, sober, i was petrified of rejection so would just look at but not talk to girls.
So back to the weekend. We’re in my brother’s gf’s room drinking and playing whatever drinking game i can’t remember and Jen walked in. There’s few moments in your life that you just remember with clarity – seeing jen is one of those – like a music stop/record scratch/angels sing moment.
She was wearing an off the shoulder long sweatshirt and jeans. long black hair and these angular sparkling eyes. Her sweatshirt was loose but it was clear she had a really big chest. She sits next to me and we hang out most of the night, not saying much (i’m more confident with drink, but still shy) looking back clearly there was a connection, but at the time she was a “cool college girl” who was just being nice.
It gets pretty late and everyone starts heading back – my brother and his gf walk with me across the hall to Jen’s room. Jen and another girl are already in there. My brother’s gf says “now no nonsense you two” pointing at us and smiling – i like stuttered and turned red (really smooth).
They leave but the other girl with Jen stays. Jen and I both get into our own beds (Jen had already changed to sweatpants earlier). Now this other girl – holy shit – i don’t know what her deal was, but she did not want to leave. Told me that Jen has a boyfriend and she’s there to make sure that we don’t hookup. Honestly, if my brother’s gf and this girl hadn’t talked all about it, i’d have been too shy to even think about making a move on Jen – she was older and WAY out of my league.
So i pretend to be asleep and it gets quiet, i look up, and the girl’s like “i’m still here! won’t be that easy”. My god this goes on for what feels like hours. Finally she decides to leave – hearing that door click was a wonderful sound.
I look up at Jen and she’s looking at me smiling. Now i make the boldest move i’d ever made, i get up and walk over to her bed. I lean in for a kiss and she grabs my head and we start making out. She has the softest lips, and she does something no other woman has since, she ran her fingers through the back of my hair and gripped on while we were kissing. I can still feel that feeling today – it was intense. I bravely take one hand and slide it up under her sweatshirt – YES her chest was HUGE. way more than a handful and my 18 y/o brain exploded. Who knows if it felt good for her, but i went to town on those giant breasts – massaging and rubbing and pulling – i was in heaven.
Now this is the embarrassing part – we’re both in sweatpants, and i start rubbing my throbbing cock against her leg, and rubbing faster and faster and…you know where this is going, i cum in my pants…
I roll off of her and we keep kissing, we break away and she’s smiling, i was too embarrassed to address the fact that i’d basically humped her leg to completion, but she didn’t seem to mind. She started tracing her finger around my now soft cock through my pants and kissing me cheek – i fell asleep that way. Holding her close, cum drying in my pants.
Not the hottest story to tell, but I fell in love that night – didn’t know it at the time and wouldn’t admit it for years. If you read my other story, you can see that Jen and I are still having fun, but I’ve developed a bit more control.
Source: reddit.com/r/gonewildstories/comments/7ywgae/my_first_time_meeting_jen
Honestly just a sweet hopeful story op