I’ve been seeing someone for a while now and we’ve grown very comfortable with each other. We are pretty much dating, but without the commitment and expectations.

Last year one of my aunts was diagnosed with stage 4 cancer. The entire ordeal was stressful and I noticed myself spending more time with my partner. For story-telling purposes, we’ll call him Dave.

Some time around February, the doctors decided to stop all of my aunt’s treatment and send her to hospice. I spent the next three weeks at work, with her, and with Dave. No one in my family was handling the news in a healthy manner. Because of this, a few days after her passing, my second-cousin (her grandson) ended up in a rehabilitation center. He was sent to the hospital the night before her viewing and called me to let me know. He wanted me to handle everything for him while he was gone because I was the person he trusted the most. I spent the day of my aunt’s viewing shuffling between consoling family members, on the phone with my second-cousin’s mother, and on the phone with his father. Read more »

I met up with some friends at a local bar that I work at for a gender reveal party last weekend. We had a private room and didn’t go over to the bar much, servers would come to us and take orders, so we weren’t around the crowd at the bar that night much.
I work at this bar on weekends, just bar backing so it isn’t that exciting but I know everyone who works there and was able to get any additional drinks or food so I didn’t have to bother and of the servers if they were busy.
The party only lasted a few hours before people started to leave but working behind a bar means that I don’t get to go out much so I decided to stay, have a couple more drinks and then talk to my coworkers as I sobered up.
I went outside to smoke a cigarette later in the night and that’s when I met, let’s just call her, the cougar. A very attractive woman in her late 50s, I am only 25. She and I began shooting the shit as smokers usually do when outside, she invited me back to the bar where she started rubbing my back and laying her head on my shoulder.
I wasn’t sure what was going on because 1, it was so random. And 2, I recently started seeing someone but with the signs that the cougar was giving me, I knew I couldn’t pass up the opportunity.
She was only in town for one night and at the bar alone, she was at a concert earlier that day. After a couple drinks and my confidence building, I decided to straight up offer to take her home. Expecting to be shut down and embarrassed that I even asked someone old older than my mother. I had a “fuck it” attitude and went for it.
The cougar had me follow her back to her hotel and her daughter (who is a year older than I am) was sleeping in the next room. We started making out and I was touching her body. For her age, her body was incredible. We started undressing each other and I began to eat out, but then, out of nowhere, she squirted on me (multiple times) I have never had anyone do that before and it just fueled the entire situation.
We started to fuck in many different positions, she was the kinkiest woman I have ever been with. After I finally came, I busted all over her. She demanded it when I said I was getting close.
She wasn’t just done with me yet. I laid down next to her completely amazed that the night was even happening but she kept slowly jerking my dick, then sucked me off saying that I’ll never get better head. She may honestly be right. She kept trying to shove her finger in my ass, I know some people are into that but I avoided it at all costs.
Anyway, she wanted me to stay and cuddle her but I knew to end the night the way I wanted it, as a story, I needed to leave. She stole my underwear trying to get me to stay and then put them on. I left commando.
Before I left, the cougar and I exchanged numbers because she has family in my area and comes here from time to time. She said anytime I want to fuck her mouth, she will have it open for me.
She has texted me since but I have yet to respond. Who knows if I’ll ever hook up with her again. It was a one night drunken experience as far as I am concerned.