I [M]24 had sex with a MILF [F]42 and met drake bell in the same night

A couple years ago, two of my cousins and i went to see drake bell perform live. Not because we are fans of the music (we are mostly into metal) but mostly because we liked the tv show drake and josh as kids and it was a bit of nostalgia. This was also before drake bell had gotten in trouble…

Anyway, we were drinking and having a good time. Earlier in the night, i had struck up a conversation with another girl only to find out she was dating a member of the band Louder Louder. After the show, we had gone up to the merch table where louder louder was and thats when i met the milf (who i will call Melissa) and her sister. Melissa was an average height woman, curvy, with dark hair that had a hint of maroon dye in it, she was wearing all black clothes with a leather jacket, and black lipstick that matched her hair. She was a pretty friendly and social girl. Tbh, i dont really remember the initial conversation because we were all pretty intoxicated 😂.

A totally unexpected night [MFM]

A few years ago during my last year of college, I (white guy about 6ft tall with a few tattoos, moderately sexually experienced) was living in a suite on my college campus with some roommates (one guy and one girl. He is a shorter black guy on the heavier side and was a virgin. She is a short, curvy/voluptuous girl with a big booty, 2 or 3 tattoos, one in the center of her back. She wore glasses that gave her that sexy librarian look, and very sexually experienced). Lets call them Billy and Lynn for identity’s sake. Both me and Lynn had ended multi-year long relationships earlier that week, so it was the first time her and i were single in a long time and Billy had a big crush on Lynn. Anyway,

Weve all be pretty close friends during college so earlier that week we had planned to drink and hangout that night. At the liquor store, she said she would “teach” us how to do body shots with tequila, salt, and limes if the tequila werent too expensive. Me and Billy kinda glanced at each other because it was really flirty and Lynn isnt the type of girl to really flirt that much if at all.

[MF] Interracial anal in the woods

In [M]y junior year of college i was really looking to expand my sexual horizons. I was in a relationship at the time but we had a pretty toxic relationship. She was very manipulative and emotionally abusive so we argued a lot and took many “breaks” from the relationship (i am no longer with her and have been in a stable, very loving relationship for years 😊). So during a period of time that i knew would be a short period of being single before we inevitably ended our break, i look advantage of my temporary freedom.

This lead me to searching the personal ads on craigslist lol (when they were still a thing, this was like 2017). I put out an ad for a black girl interesting in anal and got someone interested. We added each other on snap chat so i got to see her face and she saw mine. It was just going to be a no strings attached hookup. So a few nights later, late at night, i went to go pick her up. She said she had a place we could go because neither of us could host.

I had a shirt that helped me hookup with a girl twice. Part 2: hard anal in the woods [MF]

It had been a year or two since i had seen Alysa. She had gained a little bit of weight but she carried it well. Her waist was slightly less defined and her boobs definitely got bigger. Her ass also got bigger but, as i said earlier, was less defined due to a general increase in weight and she had a very slight belly. She wasnt the thin, tight girl i had met before, but she was a thicker version of her. Still, cute as ever. I myself had gained a little weight at the time too lol.

The night was fun, we drank a bunch. Alysa was wearing these white, lace-y short shorts and a black t-shirt. We were having a conversation and i could tell she was a little self conscious about her weight.

“Do you think i gained weight?” She drunkenly asked me at one point. Which is kind of a dangerous question to answer lol. So i replied with,

“yes, but it went to all the right places.” Which was true, most of it did.

I had a shirt that helped me hookup with a girl twice. Part 1: Attempted anal on the beach, Part2: successful anal in the woods a few years later [MF]

Keep in mind, i was a virgin at the time of part 1! Although i had had hookups, i only had oral sex and handjobs at this point.

Part 1:
It was the summer before my second year of college and i went to my friends party near the beach. I wore this shirt that had one witty, funny line written on it. I wont specify what it said just for a bit of anonymity, but its not important anyway. I’ll skip all the boring party stuff because nothing relevant to this story happened until right at the end.

It was late, warm, there was a full moon, and we all had plenty of alcohol in our systems. My friend’s brother had some of his friends over at the party. One of these girls, who i will call Alysa, was introduced to me. She was short, barely 5ft tall, blonde, had a fit body, a very cute face, and medium perky boobs. In contrast, im 6ft tall and average build. She was wearing very short cotton shorts and a t-shirt. She thought my shirt was hilarious and shook my hand to meet me, to which i drunkenly commented about how soft her hands were (Tbh looking back, im pretty surprised this ended up working lol).

My Gf and I fucked near a mountain summit on our hike with other people nearby [MF]

I indicated where the fun part starts if youd like to skip the intro. Enjoy!

My gf and I are in our 20’s and like to go hiking in the mountains throughout the summer. It was a beautiful 8hr hike through lush green forest, with two rocky peaks to climb. Once we passed the tree line, we could see for miles in all directions. There were other tall mountains adjacent to ours, but we hiked the tallest one in the area so we could see over them.

I’m a white guy, stand about 6ft tall, medium build, with long dirty blonde hair just passed my shoulders. She is a tan girl, standing about 5ft 6in with long brown hair, athletic build, and a big round bubble butt that is to die for. She knows there is a reason I like to let her go in front on our hikes 😂.

At the summit, we had to shimmy our way along rock face with barely enough room to stand. (Think of every adventure movie ever where the characters have to press themselves against the rock face while standing over a cliff). At the summit, there were other groups, and many huge black birds (ravens perhaps?). We relaxed for a bit, had our summit meal, took some pictures, and continued on our way.

Being Pegged by my Girlfriend [MF] part 2

Now, i know the beauty of having someone you find sexy arch their back in doggy style, so i figured id return the favor!

“Daaamn that back arch though!” She exclaimed.

I hear the “click” of the lube bottle, followed by a short pause. Then i felt the tip of her cock press against my ass. Slowly i feel her enter me. Inch by inch she works her way inside. I can feel myself accepting it inside.

“Ahhh fuuuuck!” I moaned
“Does that feel good?” She asked. She always checks on me when we first start to make sure it isnt hurting. One of the many reasons why i love her ❤️.
“Yes, it feels amazing” i replied

Her long cock moves further and further inside until i feels her warm body firmly press against my ass. Her cock is the perfect length to hit the back walls of my ass. All 7in of her are inside me now.

She begins slowly moving in and out, my ass almost fully stretched. As she slowly pumps, her nails run down my back and gives me goosebumps. I begin moving my body to fuck her back, a little more intensely. I feel my thick dick and balls swinging in between my legs as she moves. She can tell im ready and i want it so she grips my hips and picks up the pace.

Being Pegged by my Girlfriend [MF] part 1

My girlfriend and i tried pegging for the first time about a year ago. Since then weve done it about 3 or 4 times. We like to keep certain kinks to just an occasional thing just to keep them exciting and interesting. Anyway, here is the story of our most recent pegging and i think its the hottest so far…

It was late at night in her room. We had the lights out and had only a candle lit on the dresser next to her bed. My eyes were closed as she changed into her new lingerie.

“Ok, ready!” She said

I opened my eyes to see her curvy body in red lace-y lingerie. It was read floral fabric which made a V in between her legs and into a very thing thong. The back was strappy and it had an elegant floral, lace-y skirt that opened in the front. The candle light flickering on her curvy, athletic body accentuated by her lingerie.

I should take some time to describe our appearances. We are both white, in our 20’s, she is very tan (often times gets mistaken to be Brazilian), stands about 5ft 6in, brown hair, toned athletic body, thick muscular thighs, big and round toned booty, and D cups. She also has a thong tankine because she wears thong bikinis 😍

I [M]24 had sex with a MILF [F]42 and met drake bell in the same night

A couple years ago, two of my cousins and i went to see drake bell perform live. Not because we are fans of the music (we are mostly into metal) but mostly because we liked the tv show drake and josh as kids and it was a bit of nostalgia. This was also before drake bell had gotten in trouble…

Anyway, we were drinking and having a good time. Earlier in the night, i had struck up a conversation with another girl only to find out she was dating a member of the band Louder Louder. After the show, we had gone up to the merch table where louder louder was and thats when i met the milf (who i will call Melissa) and her sister. Melissa was an average height woman, curvy, with dark hair that had a hint of maroon dye in it, she was wearing all black clothes with a leather jacket, and black lipstick that matched her hair. She was a pretty friendly and social girl. Tbh, i dont really remember the initial conversation because we were all pretty intoxicated 😂.

A totally unexpected night [MFM]

A few years ago during my last year of college, I (white guy about 6ft tall with a few tattoos, moderately sexually experienced) was living in a suite on my college campus with some roommates (one guy and one girl. He is a shorter black guy on the heavier side and was a virgin. She is a short, curvy/voluptuous girl with a big booty, 2 or 3 tattoos, one in the center of her back. She wore glasses that gave her that sexy librarian look, and very sexually experienced). Lets call them Billy and Lynn for identity’s sake. Both me and Lynn had ended multi-year long relationships earlier that week, so it was the first time her and i were single in a long time and Billy had a big crush on Lynn. Anyway,

Weve all be pretty close friends during college so earlier that week we had planned to drink and hangout that night. At the liquor store, she said she would “teach” us how to do body shots with tequila, salt, and limes if the tequila werent too expensive. Me and Billy kinda glanced at each other because it was really flirty and Lynn isnt the type of girl to really flirt that much if at all.