This story takes place during the last days of my junior year of college. It was the Wednesday of finals week and I was studying in the library for an exam the next morning. I went to a large state school, so our library was large and impressive. It was my favorite place to study on campus and I spent countless Adderall-laced nights there. Don’t worry I had a prescription! Anyway, on the night in question around 11pm or so I was deeply engrossed in a study guide when my phone vibrates on the table. I glanced at the screen and saw that it was a text from Katie. Katie and I were “Friends with Benefits.” I’m sure everyone is familiar with the concept and how we started is another story entirely so let’s just skip ahead. Katie was studying to be a high school teacher and was a rather…buxom girl with beautiful green eyes, tan skin and large breasts. She also had a great ass and hair that started off brunette but gradually turned blonde about halfway down. I believe it’s called ombre? Doesn’t really matter I guess, but just suffice it to say she was very attractive in a conventional sense. I felt bad for her future students. They would never be able to stay focused. At least not on schoolwork
Author: IamPilotJones
Unexpectedly fucking [m]y [f]riend at a Halloween party
Apologies ahead of time for a ton of background and a complete inability to write dialogue!
In college I had a friend named Caroline. Caroline was a very intelligent, loquacious and outgoing girl. She could always bring me out of a lowly mood and was always a welcome addition when a group got together to go out drinking at the bars. On top of her great personality, Caroline had an amazing body. She had green eyes, jet-black hair and skin that was extremely smooth and pale in a very appealing way. She also had smaller breasts that I can only imagine were maybe B cups (not that that’s a bad thing) but her ass was amazingly sizeable and round and she liked to joke that it was her one redeeming feature. I highly disagreed with that. She had several features that made her extremely physically appealing. Nonetheless, for some reason it really turned me on that she knew she had a nice butt and was proud of it. She always wore skirts, dresses and tights that accentuated and showcased her lower half. One time she came to a study session for a test in a class we shared wearing those tight Nike Pro shorts. I maintain to this day that her wearing those shorts is the reason I got a D on that test (insert joke about her getting the D).
Sneaky vacation sex with [m]y girl[f]riend
A little backstory: I was on a vacation in Palm Springs with my girlfriend, Sara, and her family. I was sharing a hotel room with her brother and she was staying in a room with her parents.
Vacation had been going great. We were on day 4 of a 7-day trip. It was at this point that Sara started to get super horny. We had spent the first half of that day doing group activities at our resort. If I remember correctly, we attended a yoga session and played tennis for a while. The whole morning Sara had been giving me ‘the look’. She wanted it. Bad. She began to grab my dick through my shorts when no one was looking and whispered dirty shit in my ear. ‘I want you to fuck my brains out’ is one that has stuck with me.
The Night I Ca[m]e Inside of my Ex Girl[f]riend
I have a love-hate relationship with copious backstory/lead-up so I’ll try and thread the needle here.
The events of this story transpired on a night during the summer after I graduated high school, but I should back up a little first. From sophomore to senior year, I had dated a girl named Jenn. I loved Jenn. We had a fun and vibrant relationship that seemed like it would never end. Not too long after we began dating, we took each other’s virginities and proceeded to fuck constantly for the next 2 years. I had more sex in that time than any other 2-year span since. Trojan stock soared…but then it ended. I’ll spare you the gory details of why the relationship ended, but let’s just chalk it up to her suddenly wanting something else shortly after the start of senior year. High school shit. It wasn’t until we were done that I realized just how lucky I had been with respect to Jenn’s body. Imagine a volleyball player. Tall. Long, thick thighs. Flat stomach. Respectable breasts. Long blonde hair. But most of all, HUGE ass. I was absolutely obsessed with her ass. Still kind of enamored with it to be completely honest. Suffice it to say that we fucked doggy style a lot. I’d say Jenn’s celebrity doppelganger would be a tall, and even curvier Amber Heard. To this day, any time I see a woman with Jenn’s body type I can’t help but stare. Pavlov’s dog.