Real stories from a happily married Wisconsin couple. Some are from Him, and some are from Her. This one is from Him.
___
As you can see from my last story about betraying my best friend by playing with his sister and ex-girlfriend, I wasn’t exactly the greatest person when I was young. When I was a freshman in college, I cheated on my girlfriend with one of her best friends, Jenny.
It wasn’t exactly planned. It was early in the fall semester and I was living in the dorms. Jenny lived in a neighboring dorm building, and somehow (I don’t remember exactly) I found myself in her dorm partying. There were a number of people there. I dated my girlfriend for several years at that point, and we all knew each other from high school. My girlfriend went to a different college at the time, so she wasn’t around.
As the night went on, both Jenny and I got increasingly drunk. Soon, the crowd in the dorm became scarce, and I can remember Jenny whispering into my ear that we should go to my dorm room. I lived in a single dorm, so I naturally thought that could only mean one thing.
When we got to my dorm, she didn’t really waste any time in getting down to business. She candidly told me in a drunk voice that she wanted to fuck. She also referenced the importance of not telling my girlfriend. She wanted to fuck, but also didn’t want to lose a friend over it.
Naturally, and especially given my age, I didn’t have any objections, and soon she was removing her clothes with my assistance. She got down to just her underwear. I’d known her for years, but this was the first I saw her naked and her breasts were the largest I had seen at that point. They were probably a large C or normal D.
After staring at her for a while, she asked if I was going to take my clothes off, and I responded by doing precisely that. I remember taking my shirt of and looking up at her as she watched my take my pants off. My cock is around 8 inches hard, and she immediately laughed and joked about it (in a “you have a big cock” sort of way).
At this point, she told me she was on the pill and had no interest in using a condom. She made me “pinky swear” however that I didn’t have any diseases and made me promise again I wouldn’t tell anybody. With that, we went right into it.
We didn’t even kiss, but she came close and stroked my cock which was rock hard. I slid my hands into her panties and her pussy was completely shaved, as though she knew she would have some fun, and was already dripping wet. After rubbing her pussy for maybe a minute, she slid her panties down turned around.
In my room I had a futon, and she bent over the arm rest, using her arms to prop herself up slightly. Her ass was perked up and oriented right at me, and I remember timidly walking up to her and slowly pressing my cock to her.
After standing there for a second, I can remember seeing her hand reaching underneath her and grabbing my cock and attempting to slide it into her. She was really tight, so there was a fair amount of resistance, but after a little effort, I stretched her open and slid in. She uttered a soft moan as I slid deeper and soon I was going quicker and quick with full thrusts.
I honestly don’t know if she came, but I remember after doing this for several minutes and grabbing onto her hips, it wasn’t long before I was thrusting cum straight into her.
Afterwards, she put her clothes back on, gave me a peck on the lips, and made me promise again not to tell anyone.
Source: reddit.com/r/gonewildstories/comments/iqijrp/cheated_on_my_gf_with_her_friend_mf