Author: DontTellMeImConfused

[MF] I fucked an older woman while on a family vacation

So my grandparents invite their kids and grandkids on a really dope family trip almost every year. They usually arn’t the most wild of vacations until the most recent one, where things got pretty fucking wild at least for me.

Names are changed obviously.

Our most recent family vacation was a bus ride through a few national parks. Its not normally my thing, but my grandparents are into it and I love them so i’m into it. Anyways the first day of the bus trip I am casually chatting with family when I notice this good looking older woman around 30. She was pretty short, south-east asian, with these super cute faint freckles. I later learned her age (31) and her name (Kim). She was traveling with her mom and was continuing on sort of a world tour after graduating from med school. Read more »

Fucked (M24)y best friends older sister and her friend on a grad trip update (Xpost from r/sluttyconfessions)

Check my profile for the first part of this story. It gives context and is mostly full of teasers for this story.

Names changed obviously.

So tl;dr i’m on a grad trip with a bunch of friends and family including my friend Tom’s smoking hot older sister Jessica (5’4ish blonde cheerleader) and her friend Sarah (5’8ish brunette cheerleader). Sarah has been teasing me for years, (flashing, suggestive comments) and on this trip its ramped up to 11. We finally fucked the last night of the trip in the same hotel room as Sarah and another friend of mine, Mark.

Literally seconds after we finish we hear a knock on the door from Tom, Jessica’s brother, asking if we are ready for dinner. Jessica, smooth as hell, says the two girls were naked and still getting ready.

We all get dressed and head to dinner and let me tell you these girls pulled out all the stops. It was a fancy dinner as it was our last night so Jessica was in this low cut dress that she was practically bursting out of. The dress was shimmering black and hugged her curvy body down to her incredible ass that i had just came all over not 20 minutes before. Read more »

Fucked (M24)y best friends older sister and her friend on a graduation trip when i was 18.

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. Read more »