Long time lurker and finally decided to add in a few stories of my own. Feedback and DMs are welcome. Good stuff starts at the line.
It was a hot night as my pledge brothers and I hurriedly crammed all the cheap booze we managed to get our hands on into my buddies truck.
“Hey man, you think Sarah is going to have a good time this weekend?” Asked my buddy Tyler.
“Yeah I hope so, it’s not exactly her scene but she likes a good party” I replied.
“Nah, nah it’ll be fine. We’re rooming with Amy so it shouldn’t be a problem having a good time” he said.
Amy was Tyler’s formal date, and known for getting a little wild at these events.
It was almost the end of our freshman year and I had finally started to come out of my shell. I had a few encounters with girls so far, but not much beyond dance floor make outs and some heavy petting. For context I am about 6ft tall, brown hair, and skinny. also got lucky in the downstairs department at 8 inches and girthy. I have been told I have a “porn cock” by several people in my past.
Sarah was a friend from high school that I ironically met through a prom date, Kristi. At the time, Sarah had been in a 5 year long relationship and had seemed completely unavailable. In what seemed like a whirlwind, she had dumped her boyfriend a week or two prior to formal and I managed to invite her as my date after she kept telling me she was ready to get out from under the thumb of her boyfriend.
About 48 hours out from the event, Sarah sent a text letting me know she wasn’t comfortable going to the formal because she had started talking to a new guy, and he was insanely jealous. I was crushed, but felt guilty about being mad at her. I told her it was cool and that I had some single buddies that I could party with as I already paid for everything.
This was the start of an on again/off again flirtatious relationship with Sarah. Possibly some more stories with her for another time, but unfortunately this is where her part of the story ends.
My buddy Tyler and Amy could tell I was feeling down on myself when I told them later that night.
“Don’t worry, let me ask around my sorority to see if anyone wants to go!” Amy sweetly offered.
“No, no I don’t want to do a blind date. There’s no way anyone is available this late in the week” I replied.
“Well it’s too bad because I’ll have someone for you by the end of the day” Amy challenged back.
Amy was a woman of her word and within the hour let me know that her friend Julia was free and would love to go with me. Now I had never met Julia before and all I could tell from the pictures Amy showed me (it was the late days of MySpace and early facebook) was that Julia was blonde. As a desperate single guy, I told Amy to give me her phone number so I can set it up. I set my expectations low, knowing I had a slim chance of getting lucky with a last-minute date. However after a few texts with Julia back and forth I decided at the very least we seemed to get along and should both try to have a good time.
As the day arrived to road trip down to the beach hotel our fraternity rented, I rushed out of my dorm to the waiting pickup truck loaded with beers and bags in the back. I threw my stuff in on top and climbed into the back of the cab. Up front were my two pledge brothers, Amy was on the far car seat and Julia, I assumed was sitting right next to me in the middle both in bright red bikini tops and Jean shorts.
“Nice to finally meet you!” She excitedly said as she reached over for an awkward side hug.
Julia had long blonde hair, down to the middle of her back, with bright blue eyes and almost porcelain skin. She was tall at about 5’8” with a little bit of a pudge from the classic freshman 15 but still clearly in good shape from high school sports. However, the highlight was her huge tits fully on display. I could not even make a guess to how big they were, but let’s just say they were bigger than I ever thought I would be able to see in real life at this point.
“Thanks for coming with me so last second” I replied.
“Don’t worry, Julia has been chomping at the bit to go on a beach weekend formal” Amy giggled
“You’ll love my formal dress for dinner. It really show off the girls” Julia told me as she looked me directly in the eyes.
“Haha well I can’t wait to see it” I awkwardly laughed
Amy and Julia briefly looked at each other and broke out into laughter at how red they made me.
“Let’s start drinking already!” Amy shouted to the group.
And drink we did, it was so much easier back than to drink for hours on end. Between the ride down to the coast, pool, and the beach we were all sufficiently sloshed to start the weekend. Everyone was having a great time and even though Julia wasn’t my typical type, we were really getting along and I was sort of into her. I had kept trying to keep Sarah out of my mind though. At one point of the party walking out to the balcony and sitting down and finishing the rest of my beer while I looked out to the ocean.
“Hey everything okay?” I heard behind me.
Julia slowly slid the door shut behind her with two beers in her hand.
“Yeah, just needed a quick breather” I smiled back to her as I took one of the cheap light beers from her.
“I’m having a really good time with you. I was not sure what to expect but I’m glad I came” she said sitting down next to me on the bench.
We spoke for a few minutes about the day so far until I finally noticed she had been slowly sliding closer and closer to me. Getting the hint I slowly helped close the gap as our lips finally met. We slowly made out for a few minutes out on the deck. I was afraid to take it too far out in public still so i tried keeping my hands to myself, but I was so hard I was almost busting through my swim trunks.
———————————————————————
Julia either accidentally or “accidentally” brushed her hand over my bulge and gasped softly into my mouth.
“Let’s go, I need another drink. I left everything in the room” she quickly said standing up and grabbing my hand.
“Uhhh okay I managed to get out as she dragged me up out of my seat. Amy opened up the door to exaggerated cheers, whistles and laughs as we both realized everyone had been watching us the whole time.
“Yeah I’m sure you guys really need a refill!” Tyler shouted from the other side of the hotel room as we hurried out the door. As I shot him the finger before the door shut, I made eye contact with Amy who winked at me with a blush.
I looked down the hall at Julia fast walking down the hall to our room. I almost had to jog to catch up, catching the door before it shut behind her. As I rounded the corner to the bedroom I was greeted by a sight that will forever be burned into my memory.
Julia had already gotten in bed and was laying on her back, her body on full display. As a former competitive rower, her body was firm but thick. Her tits still barely contained by the resilient red bikini, blonde hair strewn about behind her on the pillow.
“So are you going to stare or make me a drink” she giggled from the bed.
I realized my mouth had been hanging agape just staring at her.
“S-sure, of course” I stuttered out.
“Was this it? Was I finally going to lose my v-card?” I thought to myself as I turned away from her to mix another shitty whiskey coke on the one desk in the room.
“You know I don’t really need another drink” I heard from behind me. Turning around, Julia had sat up in bed a little.
“I know you really want to see these, you’ve been staring at them all night” she said, gesturing to her tits.
“Haha sorry, I guess I couldn’t help myself” I said staying in place.
“Well why don’t you come get a closer look then” she quietly replied while slowly pulling her top over her head. Her tits were even better than I imagined as they slowly dropped from the little bikini. They somehow looked even bigger than before. Huge but firm with tiny pink eraser nipples.
I stumbled forward, eager to explore more as she giggled. We continued making out on the bed as I clumsily pawed at her now exposed tits. She sighed in my ear as I kissed her neck roughly, while scratching at my back and pulling me closer. Giving a little push, she shoved her hand between us as she grabbed at my cock through my trunks again. She groaned into my mouth when she finally got her fingers around it.
“Fuck that is thick” she mumbled to either or self or me. At this point I was on sensory overload. She quickly turned back to me and stuck her tongue deep into my mouth as she squeezed and stroked me.
I slowly let my hands fall from her bare tits down her stomach and teased along her Jean shorts as I popped open a button. She could tell where this was going and quickly helped unzip her pants and lifted them off her hips, revealing a matching read bikini bottom. As I continued to tease her she eventually just shoved me hand inside her bikini with a moan. She pushed my fingers flat against her pussy with her hand on top of mine. Eventually pushing my index finger inside of her and pulling it out, spreading her wetness around.
I was concentrating, trying not to bust through my pants as she quickly fingered herself and rubbed her clit through my fingers. Before I even noticed she had undone my drawstring and shoved her other hand down my trunks, wrapping her fingers around my throbbing cock. Using her thumb she rubbed the head of it, spreading my precum around.
Breathily, she moaned into my ears “Fuuuuuckkk I didn’t think you’d have such a big cock.” Not wanting the fun to end I quickly pulled my hips away from her wandering hands to prevent myself from finishing too early. Julia whined as she bucked on my hands, cumming with a moan as I felt a gush of wetness cover my fingers and her tongue sneak into my ear.
“I think I could use that drink right now” Julia said out of breath.
“Haha sure let me finish that for you” I said rolling off the other side of the bed. As I walked up to the desk, I decided fuck it and just pulled the rest of my trunks off.
“Oh shit, you really do have a big cock” Julia laughed from the bed. Her face still read and flustered from her orgasm as she openly stared at my achingly hard dick.
“Bring that drink back over so I can return the favor” she said with an eyebrow raised.
I took a huge gulp of it as I took my first step back to the bed.
End of part 1, let me know if anyone is interested in hearing more. I have a few more stories with Julia (one or two including Amy too).
Source: reddit.com/r/gonewildstories/comments/z772jr/how_getting_stood_up_lead_to_my_first_time_pt_1
Please write the next part.