pm_me_cutelil_boobs, Author at NSFW story

[MF] FWB hated anal unless..

I used to go out A LOT and my fwb at the time hated anal, until she was smashed. We would go out to the dive bars and up well passed tipsy at her place. Mostly we would do the standard thing, but every now and then she would have me lay down on the floor in front of the mirror. She would lube me up and put me in her ass, and spread in front of the mirror and finger her pussy like crazy until she came buckets. We would up with a puddle in front of her on the floor; she didn’t squirt but would cum plenty.

I hated it, the floor was uncomfortable, she wouldn’t bounce or ride, just wanted my warm cock in her ass while she flicked the bean in the mirror until her rocks were off. After that I couldn’t give her anal because fucking her ass was too much, no going ass to mouth and no going ass to pussy. Everytime I agreed to it because I was 22, drunk and thought giving anal was cool. Even if I just ended up jerking off in her little shower :(

[MF] My externship

Best externship ever

The second woman I ever slept with was absolutely a handful and I loved it. I was 20 and she was 21 in a tourist town where she went to university and I was on extern for hospitality.

We worked together and the first few days after I arrived I was checking out her cute ass and one of the guys in the kitchen noticed said “she thinks your cute, too”. I laughed and was a bit shy so I tried to downplay it, but I was blushing too hard to pass that off.

“Hey T, Sunshine thinks your cute, too” I had long blonde hair at the time so they called me Sunshine like the character from Remember the Titans (I’m ageing myself, I know). She turned and blushed as she turned the corner. I didn’t have the courage after that to go ask her out so we just made awkward looks at each other for the rest of the shift. Read more »

[MF] adorable Latina broke the dry spell

I was in the middle of a dry spell, maybe six months. I had started a new job and my old fwbs had moved on or no longer became convenient. My new job was at a very posh restaurant downtown serving tables. I worked the lunch shift and a few colleagues of mine told me they were heading to Hooters to get food between our lunch and dinner service.

We got sat at the table and an adorable Latina was our server. One of the guys I was with made a hard play for her and she was impressed by the restaurant we worked at. I was more concerned with eating my sandwich and beer. He wrote his number down on the receipt and we all gave nice tips because she did test us really well.

I knew my friend didn’t have a chance when ‘Jasmine’ asked who our favorite Star Trek captain was. I had to say Picard, but my friend didn’t even have an answer. He still laid it on thick telling her that we’d take care of her if she came into our fancy restaurant. Read more »

First time [MF]

When I was in a small school in the NE of the US I lived in a dorm on campus and worked in a restaurant on campus as well. I worked the pizza oven next to a window for people to see us making the food. This window also looked over the area where new students usually had classes, so I had a good view of the newest students. A new girl came up to the window one day and put a note against the window with a number on it and pointed to an embarrassed looking girl next to her. It took me a minute to figure out what was going on, but once I realized it was too late and I was too shy to act.

The next day I saw the girl again and wrote my dorm room extension on paper and showed it to her. They laughed and walked off after looking at it. The next night someone knocked on my door and it was the girl. She was cute, petite, dark curly hair and light brown eyes; she introduced herself and I invited her in. We talked about music, her friend embarrassing her with the number and how she found my dorm room number (looking back out was kinda creepy). Read more »

A long time ago in a city far away. [MF]

Almost 20 years ago when I had just graduated from school I moved to a big city. I was lucky enough to find a nice apartment with someone I knew and the rent wasn’t crazy high. I started working at a great place in my field and loved flirting with the secretaries.

One secretary was a cute early twenties girl with a flapper haircut and a dancer’s body (a story for another day). The other was black woman almost 15 years older than me. She was about 5’8″ and had long legs and impeccable taste. She always had couture clothes and her hair done. I didn’t put it together then, but there was no way she could’ve paid for her life on what she made where we worked.

I flirted with her as much as I could get away with. I was young, brash and filled with the energy of youth. My fun doubled when talking to her: she was gorgeous, knew food, was from an exotic place in the Caribbean and had been a model. My bosses would shoo me away and I would find a reason to be back at her desk. Of course the only thing was, she had a boyfriend (sometimes she said fiancee) Read more »