If you read the post over on my blog earlier this week you’ll have read about my threesome during my marathon day at work. It’s time to share the tale of what happened a few days earlier. This is the tale of how I ended up in bed with my CEO.

If you had asked me a month ago what I would be doing on this day, actually if you had asked me a day before then the answer still wouldn’t have been “Having a threesome with my boss”.

Time For Work

It was any other day. No, really it was. I woke up, had my coffee, typed up my latest blog post over at Jess and her Gentlemen, and called my taxi. When I arrived at the hotel the newest trainee Pleasure was already up in one of the rooms.

I made sure that the bar was nice and clean, ready for our guests to arrive. The hotel group chat was pretty active, so I had a feeling we would soon have some guests to attend to. Not long after I arrived, so did Caroline and about 30 seconds later our first guest walked through the door. 

Making sure that our arrival was attended to, I offered him a drink as Caroline began chatting with him about the hotel. He complimented our outfits and we flirted for a while. Most guests arrive and they know what waitress they want and that’s the one that they focus their attention on. Our guest on this day seemed very content to focus on both myself and Caroline. 

CEO means Chief Escort Officer

In a brief passing moment, Christina arrived with another guest and they headed up to the penthouse. The hotel was starting to get busy and by my estimations, it would soon be noisy too. I smirked as I took a sip of my drink from its glass. 

Our guest proceeded to ask us if we had a little time for room service. Caroline giggled and asked him if he meant both of us. I could sense that this was going to be a busy fun-filled morning.

I should also preface this by saying that in my career as a whore there are very few things that I haven’t done. One of those things was having a threesome. I know… crazy right?

So here I was, about to have my first threesome with the CEO of Takeda Media. 

JESS IT IS THE CEO OF TAKEDA MEDIA

Ok Jess, breathe this is fine. You’ll be fine. Just forget that she’s the owner of the very building you’re about to suck cock in. The very building you’re about to press against her naked body in as you both get fucked. It might be Candy’s hotel but Caroline is the most powerful woman at Takeda Media. I guess it was time to impress.

The Performance of a Lifetime

I gulped down the rest of my drink and stood up from my stool. A little bit of alcohol always settles the nerves. I tentatively made my way toward the elevator. As I arrived in the suite upstairs I slipped into my lingerie as Caroline and our guest began to remove their clothes and make their way onto the bed. 

Caroline began to rub his shoulders as I lay along his legs resting my head on his stomach. 

“Jess, want to show the gentleman your blowjob skills?”

Oh with pleasure. I rose up as he climbed to his knees and Caroline slid down beneath me and I took his throbbing cock between my lips. After a few minutes of being the good little cocksucker that I am, he exploded in my mouth. He then pulled me on top of him and fucked me as Caroline sat inches from his face. A few minutes later we switched and I wrapped my hands around his balls and guided him deep into Caroline. 

It didn’t take long before Caroline was screaming as she came, followed by another eruption from our guest as he filled Caroline and let it drip onto my face. Things were hot, they were sweaty, they were messy, they were exciting. 

The Grand Finale

“Everyone cums, that’s the rule” 

Those words from our guest echoed around the room as he pulled me up, fucking me deep and hard until I couldn’t contain myself anymore. Cumming hard for him and a few seconds later him cumming again. 

Eventually, we all fell into a heap on the bed. Breathless and dripping with both sex sweat and cum. The three of us lay there in a bundled cum soaked heap for a few more minutes before he had to take his leave. Caroline and I headed for a shower to clean ourselves up before joining Anna, Pleasure, and Christina who were now occupying the bar. 

Working at Candy’s All Inclusive Sex Hotel is never dull. It’s not every day you can say that you went to work and had a threesome with your CEO. Now I just need a willing guest to test out that blow job rug with me and my list of “haven’t dones” is almost empty.

Oh, you want to help me test it out? Take this taxi and I’ll meet you there.

What about you? Who was your first threesome with or even better who do you want your first threesome to be with?