Author: ThePainGuru

The time I accidentally fucked my girlfriend’s twin sister. [MF]

Clarification: everyone in this story is over the age of 18. No one was a minor/underage.

So this story takes place in my senior year of high school. My girlfriend, Ashley, and I had been going steady since we started dating in our sophomore year. Our families had known each other for years and they were very happy when we started dating. We were both 18 but we had never done anything. Close to the end of the school year she finally told me she was ready to go all the way, as she was still a virgin. She told me that her parents were leaving that weekend for Maine and would be gone early Saturday morning. She told me her sister would be there but not to worry about her and that she’d probably come and go throughout the day. She asked me to be over around 9am and that we could have the entire day together. She said she’d leave the door unlocked and just to come in. Needless to say I was excited. Ashley is on the shorter side about 5’3″ (but don’t call her short) and about 110 lbs. She has shoulder length brown hair and deep blue eyes. Read more »

[M]y Boss makes a dollar, I make a dime, and that’s why i [F]ucked her on government time. [MF]

Shitty day at work today (didn’t get the promotion I was going for but instead got more assigned duties) so I figured I’d share the time I once had sex in the office with my former boss at a previous job.

So some back story: I was a former government employee working on an Air Force base doing accounting work. The brand new office building they spent 5 years and $25 million to build just opened up for our division with enough space to have everyone get their own small but private office with a door that could close. Now being one of the only men in the office at the time I was tasked with helping to move all the furniture and supplies to the new building. My boss at the time was in her mid 40s and I was 30. Because of my position I was placed next door to her office which was good for me since she liked to wear tight fitting dresses and lower cut blouses. Read more »

[M]y first time delivering pizza to a Sorority house. [FMF]

So I used to work for one of the three big pizza chains as a delivery driver. On one Monday night we got a huge order from a local College that was over $100 a pizza, breadsticks, and desserts. Took us a better part of an hour to make everything and load it up. When I finally got down to the campus it took me a minute to find the sorority house. When I finally was able to find it I grabbed the three separate bags of food and walked up to the door and rang the doorbell.

As soon as the door opened I could smell that they have been smoking a lot of weed. The girl who opened it screamed ” The pizzas here!” like she had won the lottery. She quickly ushered me inside where she and two others were in the living room and had me set the food on the nearby table. I pulled out the receipt and told them the total and they went bug eyed. “We didn’t order that much.” they swore to me. So I proceeded to read off the order to them and watched as they nodded with each item. When I was done reading it off they looked at each other and said “holy shit” and proceeded to search for money. Read more »