This happened a few years ago and one of my biggest regrets is that I never saved screenshots of the texts on my computer before wiping the phone.
This story is about my girlfriend at the time, we’ll call her Kaitlin. Kaitlin is about 5’9″, a natural redhead, slightly thick but in a very good way, has a great ass and boobs, and was only 19 at the time.
We had only been dating for about 3 months when this story happened, but we are both very sexual and had openly talked about our sexual past. Despite being only 19, she had a bit of a slutty phase just before we started dating, and she knew I enjoyed hearing about it.
Kaitlin worked at the bakery in the local grocery store and they had her work the night shift a lot because she was one of the faster workers. Given how cute she is, it wasn’t surprising that a lot of the guys that worked there had a crush on her, and she preferred to be open and let me know whenever a guy made a move on her. Neither of us were really the jealous type and we pretty openly talked about it when we found somebody attractive. However, it was a little shocking when she enthusiastically told me about a “really hot black guy” that worked at the store during her last shift, we’ll call him Jason. She told me Jason was one of the contractors that would clean the store, was probably in his late twenties, and looked pretty fit. I thought it was a little strange how excited she seemed to be when talking about him, but it wasn’t a big deal and we pretty quickly moved on to other topics.
A week or so later she excitingly told me about Jason again when we hung out. She said she doesn’t see him every night because they rotate which contractor cleans which store on a given day, but he seemed pretty cool and they had made small talk a few times. She mentioned how he wasn’t going to be working at the store much longer as he was getting a new job or something. I was both super turned on and a little jealous as she enthusiastically told me about this guy and it was pretty obvious she would fuck him if we weren’t together. Kaitlin and I ended up having sex that night and I decided to tease her and ask her “You want to fuck Jason, don’t you?” while I was deep inside of her. Unsurprisingly she moaned “yes” and continued to moan a lot louder than she normally does as I started to fuck her harder and call her a slut. After sex there was no more mention of Jason and we continued to hang out normally.
The next time Kaitlin worked the night shift, I decided to text her at the start of her shift and tell her she should “go for it” and try to hookup with Jason if she gets the chance, as she might not see him again before he leaves his job. I waited nervously for a response, worried that she might be mad for suggesting such a thing. About half and hour goes by before getting her text “I’m so glad you said that. He’s working tonight! It’s like the universe is telling me to fuck him.” I responded something to the affect of “Let’s see if you can pull it off” and asked her to text me the details if it happens. I ended up going to bed but had trouble sleeping, I was so anxious wondering what was going to happen. I woke up around 3AM to a Snapchat video from Kaitlin and a bunch of texts. In the Snapchat video I a saw Kaitlin in her work uniform, wearing a $3.99 price sticker on her shirt, and spitting out cum before wiping it off her lip. The video was captioned with a captioned “Waiting for him to knock on the door so I know the coast is clear to leave the bathroom lmao”.
After seeing that video, I rushed to check my texts and see the details on what went down. Kaitlin said she had made cupcakes earlier in the night and was packaging/pricing them. She decided to put one of the stickers on her shirt as well for fun but quickly forgot about it. Now I know this part sounds like something corny out of a porno, but she swore this is how it went down. Later on in the night, Jason ends up coming up to talk to Kaitlin and asks her “Where do I swipe?”. She asked him what he meant and Jason pointed to the sticker on her shirt. She said she was super embarrassed, laughed nervously, and her face probably turned super red as had totally forgotten about the sticker on her shirt. But she pulled herself together and came up with the “smoothest response I’ve ever had” in her words. Kaitlin told Jason that “it was actually a chip reader and would require insertion”. He knew exactly where this was going and responded with “I thought you had a boyfriend?” and she responded “I thought you had a girlfriend?”. He responded “touche” and they made the plan for her to take her break and meet up at the staff bathroom at the back of the store.
They made sure the coast was clear and snuck into the bathroom together. Almost immediately Kaitlin was on her knees sucking Jason’s cock. She told me his cock was a bit longer than mine and a lot thicker. She was struggling to take his whole cock in her mouth, but he grabbed her by the back of the head and made her go all the way down on him as he fucked her throat. She told me she was getting super wet with how assertive and aggressive he was being with her. After giving him head for a while, he asked her where she wanted him to cum. Kaitlin responded “You need to fuck me first. I did not just risk my job to give you head”. Jason helped her up and then brought her over to the bathroom sink. She said she had barley slid her panties down before he aggressively bent her over the sink and slowly slid his cock inside of her. Even with me it took a minute to get inside of Kaitlin as she was so tight, so she had to try not to scream as Jason continued to push himself deeper, not giving her much time to adjust. As he began to fuck Kaitlin, he would begin each stroke slow and gentle, but then pull her in forcefully at the end of each thrust, forcing her to take all of it.
The deep thrusts became less painful as she became even more wet. Jason took this as his cue to be more aggressive and started to the pick up the pace, slapping his legs against her ass with each thrust. Kaitlin told me she started to feel guilty as Jason got more vocal and started telling her how much tighter she is than his girlfriend and how Kaitlin gives way better blowjobs. Kaitlin told me how she was trying her best to be quiet and not moan, but he made it difficult with how hard he was fucking her. Jason pulled her hair with one hand and grabbed her waist with the other, pulling her into every stroke. She said what made it even more hot was being able to see herself in the mirror, bent over the sink of the work bathroom, and being fucked by this guy she has barely even talked to. After about 10 minutes of fucking, Jason asked her where she wanted him to cum. Kaitlin told him her mouth and he quickly pulled out and help her to her knees, cumming what she said was a “huge load” in her mouth. She had to swallow some as it filled her mouth, but saved some of it for the Snapchat that she sent to me moments lately. They made the plan for him to leave the bathroom first and knock on the door a few minutes later when the coast was clear. Jason knocked on the door and she left a few minutes later. Kaitlin said Jason was on the phone with his girlfriend as she left the bathroom and she instantly felt less bad about fucking him as his girlfriend was yelling at him and sounded like a real bitch.
That ended up being the last shift Kaitlin saw Jason, so it ended up working out that she went for it that last shift. This was the start of something new for us as it really turned both of us on and I started to let her have hookups with other guys as long as she got permission from me beforehand. This led to a few more stories about Kaitlin that I may share at some point.
Source: reddit.com/r/gonewildstories/comments/hj0dhy/fm_the_time_my_girlfriend_19f_hooked_up_with_a
Please share more. That was a great story!!
Do you get to hook up with randoms too?