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TIFUpate: allowing my coworker to set me up

TIFU by letting my boss see me getting my dick sucked

This was not tonight, but a few years ago when I had just started working for a start up. It was my first job which involved a lot of traveling (which I loved doing) as I was doing business development. My boss (co-founder of the company) and I travelled together quite a few times when I was a bit inexperienced which helped us bond and grow the company together.

From a personal perspective, I just had came out of a depression phase and was just playing the field in terms of experiences and women (as I literally felt Iike I had nothing to lose and I genuinely felt gratitude that I was still breathing) I spent my salary on dates, hotels, being with multiple women and just spending almost all of my money on experiences rather than saving up (I was always honest on what I wanted with the women from the start btw)

So the start up went on for a couple of years. We had grown, not exponentially but healthily and looked strong for a few quarters but I personally felt like I was going anywhere. So I applied for masters and shortlisted a few colleges I wanted to go. So when my dream college came knocking that I was accepted, I accepted the offer and quit my job. This also meant that I had to move continents. Naturally that meant me submitting my work phone, laptop and so on. I had to shift the data (photos, videos, contact ) and everything I had taken to my personal phone. So on the last day of work, I was given a grand goodbye. Me and my boss got drunk spoke about all the good times and how this changed me as a person and how I’m grateful for all that has happened stuff like that.

The next morning I woke up to see my boss sending me a video of MY DICK GETTING SUCKED BY A GIRL ON MY PERSONAL NUMBER with a “?” On text. I was like, “is that me ?” Holy shit that’s “A” and that’s my dick and my boss doesn’t know that’s me coz my face ain’t seen I lose my shit !! I was like how the fuck did that happen. Turns out, I deleted the photos and videos but the phone was backed up and the videos and photos I sent from my work phone to my private phone still existed in the chat. I rushed as fast as I could to the office with a mad urgency and asked him for the phone and deleted everything. But the damage unfortunately had been done. He wasn’t sure if it was me, but the way I rushed and reacted, confirmed it for him that it was me. Also, I knew him long enough that I knew that he knew. I could’ve probed further but that would only mean me making it more certain it was me. Fortunately, my boss knew how to keep a secret (as far as I know) and that was the end of that.

Some years down the line, we are still good friends and talk often, but I’ll never forget the fact that he has seen my dick and there’s no way I can pursuade him and just made me peace with it

TL;DR - my boss found my video of me getting a blowjob on my work phone.

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