Dating a CEO, manager or work colleague

I was in a discreet relationship with a high-profile CEO and his manager — both from the same office — for nearly 6 to 7 months. They kept it under wraps, asking me never to post or speak about it… but now, the CEO has moved abroad, and the manager’s switched companies — so it all came to a quiet end. ??

Ever been someone’s confidential comfort at work? Or had your own secret bond with a boss or colleague? Let’s share stories

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Displaying 1 to 11 of 11 comments.
No Picture vinisissy	Posted On Apr 10, 2025 It started with just a swipe. A dusky, confident, well-built manager — 35, married, working at a successful Chennai startup. His profile gave pure Daddy vibes. We chatted, flirted, and the kink slowly came out. He was dominant, sexually frustrated, and stuck in a sexless marriage with a traditional wife. He needed more — and I was more. I told him I’m a submissive sissy. Soft, smooth, obedient. A dirty little doll who loves to serve. He told me his boss — a 50-year-old gym-built, rich CEO — was looking for a discreet PA to “handle stress.” No women. Too risky. He needed someone like me. A week later, I met them both. I came clean-shaved, freshly showered, with my tiny caged clit tucked and plug deep inside. The manager gave me a red fem dress to wear. I slipped it on — tight, slutty, perfect. Then we met the CEO. Broad chest. Strong voice. Expensive cologne. Pure alpha. He invited me for coffee in a hotel room. When the coffee came, I was still in that dress. The delivery guy didn’t blink — and I felt my hole twitch from the thrill. They talked. I listened, soaked, leaking. And then, they tested me. They pulled up my dress, left me bare from the waist down. I was pushed to the balcony glass, city lights glowing. I dropped to my knees and *** both of them. Slow. Deep. Wet. I took their thick loads on my face, warm and messy, then cleaned up like a good ***. That was my first interview. And I passed with flying spit. After that night, I started working part-time. Every evening, after my regular 9 to 6 job, I transformed. From 7 to 10 PM, I became their sissy office stress relief. Normal clothes outside — but inside? Always in soft fem panties, tiny bikini sets, sometimes even with bra cups stuffed under my shirt. They made me their post-work dessert. And I loved it more than my real job. Some nights, I served them both dinner. Just me in apron and heels, soft plug inside, cheeks full of their ***. After eating, I’d go under the table and finish them off again. Other times, I’d be under the CEO’s desk while he handled meetings — quietly *** him, lips stretched, throat full. They trained me to be silent, obedient, perfect. One night, I even drank his *** in front of his employees — mixed in a coffee cup. They had no idea. My sissy *** swallowed every drop like it was milk. The taste, the risk, the heat? Unmatched. Some evenings, I waited in the corner bay — alone, lights dimmed — just watching sissy hypno on mute, staying plugged and ready until he called. As soon as his message popped up, my body reacted. I started craving his 7-inch, ***-exploding *** like an addiction. I started dreaming about his messages. Checking my phone. Hoping. “Come now.” That one line was enough to make me wet instantly. Some nights, we’d sneak into his room or back of the office after hours. He’d unzip and use my *** without saying a word. Quickies in the car. In parking lots. In dark restaurant corners. My jaw was sore. My soul was happy. And it didn’t stop there. There were nights I mixed their *** into my food. I chewed slow, feeling every drop inside. Swallowed everything with pride. Some nights, after everyone left the office, I walked around barefoot with both their *** dripping inside me — messy, sticky, soaked. That’s when I knew. I wasn’t just their ***. I was their possession. And I wasn’t working part-time. I was living full-time in submission. My 9 to 6 paid bills. But my 7 to 10 made me feel alive. The experience I shared was from a past arrangement. I’m no longer in contact with the manager or the CEO mentioned, so please don’t ask for their personal details or try to reach them through me.
No Picture Prem69vishal	Posted On Apr 10, 2025 Good vini sissy, seems to be fiction but still giving some hardness while reading
No Picture vinisissy	Posted On Apr 10, 2025 Its not fiction, I dated with full of discreet now opening up just to tell my experience
No Picture vinisissy	Posted On Apr 10, 2025 There is lot of high profile mens who looking for trans and bottom but they are full of discreet and opening up rarely. We need to just be trust the process and be open minded and also discreet enough
No Picture Ranga21	Posted On Apr 12, 2025 If any matured well settled 50+ guy wants to try me do reachout.
No Picture Kingofhearts87	Posted On Apr 14, 2025 I was working as Sr Manager in shipping company. There had with many interns and my jr but trying with colleagues is bit dangerous. U should move when u get atleast 30 % signal from them
No Picture BiGudGuy	Posted On Apr 14, 2025 I dont want any benefit workwise, but it will be nice to have such higher ups in life to whom i can serve discrete
No Picture Botumas	Posted On Apr 15, 2025 My previous company GM and manager HR and a boy all.*** me regularly on weekly basis I shifted job so weekly oneday I should work for their tool.is the agreement Either or weekends if.poasible.or during weekdays I should take off or work from home and serve them. It was good in all means During when we all in same office they use me rarely only but since I shifted other office made them violent and so it gave them feeling that a bitch is lost Anytime freeuse bitch is lost I then planned to shift out of station too for my work Then they made a deal and agreement that in a month atleast 4 days that means a day in a week I should be their *** And that been going on for 2 years and working well... One day in a week I will report to my GM house office time 8.30 and till 6.30 I am their property the use as they wish and that gives me immense pleaure and offcourse supports financially too... Money is secondary being *** is primary requirement So they knew me very well and this high profile they refer me to their equal profile contacts and i haveto serve them too Sometimes they take me.out of station and this 4 becomes 5 or 6 since some of their friends joins and *** me a lott lott lott
No Picture Khakha	Posted On Apr 15, 2025 Great experience @botumas and @vini
No Picture Gowtham999999	Posted On Apr 17, 2025 Yes i had in my previous company where i got a manager from GR. We used to stare at ofce and we never even smiled. But after 6pm, he tooks me to his home in his ofce cab, enjoys my succulent tender body and all possible ways. At last he got transferred and i left the company....🥲🥲
CrazyKrish93	Posted On Apr 18, 2025 It's my dream be such a discrete slave or sissy to a boss alpha male. I'm open for such openings