I have been needing to get this off my chest for a while.
Going to use fake names obviously.
The year was 2015 i had just graduated high school and me and a bunch of friends+ family went on a 3 day trip to mexico.
My friend group was close and all of our parents were good friends as well. Naturally that meant i had been hanging out with and seeing my friends families all the time growing up. There is one friend of mine, i’ll call him Tom, whose older sister i had always had a crush on (i’ll call her Jessica).
She’s about 3 years older than me and was going to college at the time we graduated.
I remember her wearing these tight shorts and tank tops around the house, always making fun of us for doing dumb shit. She was only 3 years older but to me it seemed like a lot more. She is about 5’4, blonde, and was a cheerleader at our highschool.
Nevertheless as part of her messing with us sometimes things would get sexual. There were other instances of this but for example i was on a road trip with my friend in an RV and Jessica flashed me her pussy through those super tight shorts and at one point did circles on her clit while reading a book right in front of me.
I was too shy to do anything about it for years until this trip.
So we all arrive at the airport and she barely acknowledges me but i’m having a good time with my friends so i dont really mind. By chance we end up sitting together in a three person row, with Tom on the left and his hot older sister to my right. After a while her brother falls asleep and not 15 minutes later Jessica leans over to me and we began chatting, first small talk about school and whatnot. Then she asks about my love life. I had just broken up with my girlfriend and was still a little shook by it so i told her a lot.
Looking back on it she was masterfully guiding me to what she really wanted to ask.
“How was the sex with your ex?”
I freeze because i didnt usually talk about my personal life like that at that time but I manage to get out that it was good. She giggled and asked me more questions about what positions i liked, how big my exes tits were, whether she liked it rough.
As i start to answer i’m getting incredibly horny, my cock is rock hard under my loose travel clothes and Jessica’s brother Tom is sleeping right fucking next to me. She clearly noticed i was both ultra horny but completely ignored my clearly visible bulge. Eventually she said she was going to sleep, and about 5 minutes after “falling asleep” she slumps her head on my shoulder and her blanket drapes over my crotch.
Suddenly i feel her hand slide up my thigh onto my throbbing dick. She starts rubbing me through my sweatpants and i can barely contain myself. She started to lightly suck on my neck and i came right there in my pants.
That night we all went out dancing and drinking. She straight up ignored me the entire time, even rejecting me when i asked her to dance. She was with a few of her older friends who all my friends were trying to fuck including this taller brunette girl named Sarah. I watched her dance with all my friends but every once in a while i would catch her giving me the fuck me eyes.
I ended up getting way to drunk that night and got put to bed.
Now remember that our entire families were there, we had to be extra discreet. Jessica never openly flirted with me in front of people, but the second we were alone she would be on me like glue. The thrill of this secret was incredible, i was practically frothing at the mouth to fuck the shit out of her.
On the last night i got my chance. Me and a different friend were pregaming dinner with Jessica and Sarah in her room. Things got a little hot after a few tequila drinks and before you knew it we were coupled up on both hotel beds making out. The other couple began to shed their clothes and we absolutely lost it.
We tore at each others clothes like they were paper. Before i knew it we were all naked and this dream girl of mine for 8 years was gagging on my cock. I eventually flipped her around, grabbed her by the hips and fucked her like i’ve never fucked before or honestly since. She moaned, begged, and screamed my name. My old girlfriend had been no where near as sexually arousing to me. Finally i came the largest load of my life all over her ass and back.
We’re both breathing heavy and the couple on the other bed had finished just a bit before us when there is a knock at the door, its Tom asking when we’ll be ready for dinner. He didnt now i was there but Jessica answered smoothly that they were still getting ready. We went to dinner and the four of us in the room were all eyefucking each other.
We spent the entire rest of the night fucking each other in all the different ways we could think of. We had pushed the two beds together and fell asleep in a sticky, hot pile. More detailed description of this activity to come but thats fore another post.
Best fucking night of my life bar none. Thanks for reading.