I connected with [m]y [f]ormer boss on Tinder

This happened just over the weekend.

To recap for anyone who hasn’t read my earlier stories, I’ve been on a bit of a Tinder binge for the last little while after a breakup. Last week I was absent-mindedly swiping while watching TV and I checked a match I had just gotten. I hadn’t noticed, but one of the guys I had swiped right on was my boss from four years ago. He’s a pretty good-looking guy, about five years older than me. Not someone I ever had thought about in that way, but his picture looked good and that’s why I matched with him.

Here’s the thing about my Tinder account: it’s pretty obvious from looking at it that I’m not looking for a relationship at this time. Without going into too much detail, let’s just say that it’s pretty obvious from peeping my profile that I’m looking for one night stands and booty calls. So when I saw he mad matched with me, I freaked out. This just felt so awkward and weird. I was so embarrassed I almost deleted my account. Then I saw he had written me a PM. It took me a few minutes to work up the courage to read it.

The PM was friendly. He said he hoped I didn’t mind that he swiped right for me, but it would be nice to meet up and catch up some time if I was interested. He also complimented my profile photos and said I looked “cute.” The message was a tiny bit thirsty and definitely way too forward to send to a current employee, but way more polite and formal than most of the shit I get on Tinder.

I wrote back, thanking him for and returning the compliment (I didn’t say he looked cute, though) and said I would have to see what my schedule for the weekend looked like (in reality, it was wide-open). We messaged back and forth for the next hour or so, talking about what we were up to at work etc. He started getting more forward, calling me “pretty” and “gorgeous” and, as I kind of warmed up to the idea, I got more flirty with my messages too. I admit, the situation turned me on, as well as making me feel really nervous and exposed. This was someone I knew, even if he had only been my boss for six months. I still had him as a professional reference. Still, it was hot. It made me feel really naughty.

At some point he asked me for a selfie, so I sent one and he replied with one of his own. Over the next hour, this escalated a bit… not to the point of sending nudes, but I may have texted my former boss a picture of my bra. At that point, he said he would really like to meet up if I was down. I said I was and we set a time, for Friday night.

We met up for a few drinks and chatted a bit. I drank kinda fast. I need to be a bit tipsy to do this kind of thing, I’m really proper and shy when I’m totally sober. Just a few drinks really helps me let loose and have fun. Before long, we were making out on the street. We were not far from my place, so I led him by the hand all the way to my door, inside and into the bedroom. He knew what to do, laying me on the bed, climbing on top of me, kissing my neck and fingering me under my skirt. I moaned and arched my back and he moaned too and told me I was so fucking hot. I told him I wanted his cock and he took his clothes off while I stripped myself naked. I was shaking as he climbed back on top of me. I was nervous and turned on. This felt so naughty and reckless and steamy and scary and good. I guided him into myself and we both moaned while he filled me. He thrust a few times, slowly. I held my breath while he thrust in, exhaling while he pulled out. “I can’t believe I’m doing this” I blurted out. He grunted and then kissed my mouth. “Me too,” he said. I asked him if he had ever thought about doing this with me when I was working for him. By the end of the question I was barely able to whisper the words out, they just felt so naughty. I felt my face flush up. So did his. He started thrusting faster. I could tell he was having a hard time making the answer come out. Finally he said yes, he thought about me all the time.

He fucked me on my back for another few minutes, then pulled out and got me on all fours. He spanked my bum while taking me from behind, moaning and grunting all the time and asking me if I liked it like that, do I like my boss’s cock, am I a good little girl and telling me how good I felt, how hard I was making him. We both came like that.

After, we talked a bit, exchanged numbers and agreed that neither of us were looking for a serious relationship. I don’t know if we’ll see each other again, but I did suck him before he left for the night.

Source: reddit.com/r/gonewildstories/comments/d2q69v/i_connected_with_my_former_boss_on_tinder