I work at a small start up in an office with 15 others. It’s a great company, but the work can be a little boring. I mostly fill out / revise paperwork and don’t have many friends. I don’t mind the work but it does get a little tedious, especially since I don’t have anyone to chat with.
The only person I feel comfortable with is my boss. He’s very light hearted and loves making others laugh. It’s great when he comes into the office. I admittedly have always had a crush on him but he’s happily engaged. When I was first hired he created a group chat with me, and two other new hires in case we had any questions. We would often chat in there and share memes / check up on each-other.
I quickly became used to texting him and we started to message each other privately. We usually talk about work but occasionally he will send cute texts complimenting my outfit or saying something like “Want a coffee sleepy head?”. It makes me really special since I’m the only one he really does this with.
As I was getting ready one day I jokingly texted him “Are you coming into the office today? What should I wear? :)”. He responded with “Wear a dress and heels, we’ll go out for lunch”. Just seeing that text gave me butterflies, it was so cute. I wanted to be flirty so I sent “Okayy, but if I’m late it’s because I’m getting ready for you “. He came and picked me up and we went out to a pub down the road because they have a patio and the weather was nice.
During lunch he told me how great he thought I was doing, and that he could see me getting a promotion if I kept things up. He also said “I don’t usually get to have lunch with someone so beautiful”. After lunch driving back to work he put his hand on my thigh and told me that his fiancée can’t find out about us. I assured him that I wouldn’t tell and he said “I can see you getting that promotion in the near future hun”. It was really exciting.
The next day while working I received a text from him telling me to come see him in office. When I got there he said “Close the door behind you and take a seat”. He then went over the promotion and all the benefits that go along with it. He also explained that I’m going to be working alongside him and if I impress him he would have no problem promoting me in a couple weeks time.
He then asked if I was a good kisser. I nervously said “I think so”. He laughed saying “Everyone thinks they’re a good kisser, you’re gonna have to prove it”. I then walked over to him and he stood up. He grabbed my waist and kissing me. He felt me up as we were kissing. He then stopped for a moment and said “Wow you didn’t lie, you’re a great kisser”, and went back to kissing me. Eventually he started to kiss my neck and rub me through my pants.
Things stopped there, but a couple days later he asked me to come back to his office. We kissed again and things went a bit further. He told me he wanted me to take my clothes off and I obliged. I slowly undressed for him only keeping on my lace panties. It felt so wrong being naked in his office. It was hot knowing all my coworkers were outside of his office and didn’t know what we were doing. I could tell he was rubbing himself as I was undressing and there was a noticeable bulge in his pants.
He then told me to come over and unbutton his pants. I walked over to him and he stood up like last time so I went into kiss him but he stopped me. He didn’t want to kiss, and said “Just get on your knees and unbutton my pants like I asked”. I nervously got down on my knees and unbuttoned his pants and pulled his dick out. It was pretty big . I sucked it for about 5 minutes, looking up at him every now and then to make sure he was enjoying it. I started out sucking slowly but he grabbed my hair and made me go a bit faster. When he finally came he did it on my face, which I never really had a guy do before but it was pretty hot.
After I got cleaned up and got dressed I went back to my desk with messy hair and make up. It didn’t seem like anyone thought anything of it. This continued for a couple weeks, every second day or so he would ask me to come in and help him. I would mostly just suck him off but some days he wanted to touch me too. Sometimes he would even take calls / talk on the phone as I sucked him off. It was so fucking hot.
It didn’t take long before I was promoted and I now work right outside his office. We often have morning “briefings” where we will make out and play with each other. We haven’t had sex yet as he has expressed that he’s worried about taking things that far, but at this point we’re basically there.
There’s lots more that I could have included in this post but I didn’t want it to be too long and I didn’t know if there was a character limit. Maybe I’ll post a part two if you guys want !
If you have any questions feel free to ask :)
Source: reddit.com/r/gonewildstories/comments/p4dd59/flirting_with_my_boss_of_benefits_fm