Volume 1: The Cross-Dressing CEO

A few years back I had a client that would book semi-regularly – I’d see him once every 2 or 3 weeks but for longer bookings (always 3-4hrs+ and he’d always tipped very well). He would have to be in his early 50s and was always dressed immaculately, always in a business suit and always smelled amazing.

Over time we developed a rapport with one another and it gave him the ability to explore more things that he couldn’t in his personal life – some things he’d try and then discover he didn’t really care for it and others he LOVED!

Through seeing him regularly over a long period of time I also got to learn about the real him – past his high profile job, his money, his divorces and his children. He was a high strung sort of person, always working, always having deadlines, always go, go, go – in the room though, he was just Robert* – he’d crack jokes, be really easy going and fun. Our time together appeared to be like an escape for him, away from the pressures and stresses of the world where he could just play and be himself.

The last time I saw Robert*, he stumbled in much later into the evening than usual and quite drunk (he’d usually have a couple of whisky’s at a bar after work before heading in but this time he was slurring his words a little), this time also he’d booked a lot longer (well into the morning). Sensing something is up, I asked him if everything was alright (I’d thought maybe someone had died by the state he was in). He told me about an impending business deal that will be happening the following day and that it was kind of a make-or-break deal that could either be his magnum opus or cripple him career-wise (he’d previously been talking about a potential move into a more lucrative position in the US).

I cautioned against arriving hungover to the meeting but he kind of brushed my concerns saying he just needs the night to relax and get his head together and he will be fine, that he doesn’t want to talk about work or what he has to do or anything.

So we proceeded with our booking… Other than that little initial hiccup, and his drunken state, he was still Robert* – in fact he was even more funny being slightly pissed. He’d snuck in a bottle of whisky so we took turns sipping out of the bottle, like teenagers trying to pinch some of their parent’s alcohol. We joked, laughed and carried on like we usually did.

Things became more hot and heavy and he asked me to take control – we had quite a bit of experience together in the past with dominance and submission (in fact a lot of my more ‘high-profile’ clients enjoy this service as it allows them to relinquish control for once – where they don’t have to call all the shots like in their workplace or private life).

I started off by ordering him to lie on the bed naked while I fastened his wrists and ankles to the bedposts then using his tie, I blindfolded him. I looked down on my handiwork proudly as he squirmed. Finally I put him out of his misery, raking my long nails up his torso, his senses seemed to be acutely aware of touch due to the lack of vision and movement and he let a long breath in anticipation of what was to follow. He was completely at my mercy and both he and I loved it!

I positioned myself on the bed where I was straddling his chest, deciding what my next action would be. The sexual tension in the air was electric, both of us not sure what would happen next. Finally, I made my move.. Shuffling up, I got myself into position to straddle his head.

Soon as I started moving upwards, Robert* already knew what was about to happen. Riding his face, I got myself to completion twice before falling back and noticing how stiff he’d become in the meantime. I got him ready and whipped his blindfold off as I started my ministrations on him.

We went several amazing rounds before finally I untied him from the bedposts and we curled up in bed to recover and catch our breath. A few more swigs of whisky and it was time to move our party into the spa.

It was absolutely glorious luxuriating in a spa after such a workout, Robert* massaged my shoulders and kneaded the tender flesh as I massaged a more intimate area of his, as we drank and talked.

Soon the spa became ‘overheated’ and I ordered him onto the bed for another hot and heavy session of sex.

Following the several rounds, the spa and additional rounds of drunken, sweaty sex, I went to touch up my makeup (I’ll be damned if I look a mess, no matter the situation) and he made a comment about me looking better without makeup. “That’s very sweet of you, but I’m not one of the 20 year olds here, this goes on like Spakfilla” was my response. He laughed at my remark, and I don’t know if it was the alcohol or partying or just a general loss of inhibition, but he was fixated on me putting on makeup. “Did you want to wear some too?” I asked. Robert* replied with “Are you going to make me?” in more of a suggestive tone rather than and actual question. Knowing where this was leading, I told him that I’m going to make him my beautiful little bitch and he’s going to put on a fashion show for me.

I must say, for how tipsy I was, my makeup skills were on point. Robert* was the prettiest 50-something year old man that night! The makeup was heavy but very glamourous. I even found a lingerie set of mine that I’d bought that was far too big for me and got him to wear it and parade it around the room for me. Even he admired himself in the mirror, playfully telling me how I was jealous of how pretty he was. I laughed and ordered him around – that was our role that evening until the morning ‘dominant’ & ‘bratty submissive’ and we had an absolute ball!

Suddenly, between another round of drinks, party and play, the intercom buzzed announcing 5 minutes left of our booking. Robert* asked what time it was as he frantically looked for his watch. He realised he was running over time and had to be at work shortly as he started scrambling for his things.

I grabbed a towel to cover myself and raced out to go grab my makeup wipes from my locker to remove the makeup from Robert* and allow him to attend his meeting looking somewhat presentable.

Of course, when things go wrong, everything seems to go wrong.. Tearing through my locker, I couldn’t find my makeup wipes anywhere, checking each bag I had and rechecking. Suddenly I remembered letting one of the other girls use them. “Does anyone know where Sara* is?” I announced to the ladies in the locker room. To my dismay, she was in a booking and no one knew where she had left them. Finally one of the girls offered hers which I grabbed and raced back to the room.

Running back to the room, I almost skidded on the linoleum.. Only to find that Robert* had already left.

“Fuck, fuck, fuck..” I said to myself as I ran to reception. Barely catching my breath, I asked if they’d seen my client or if he was around. “Oh, the guy in drag?” the receptionist asked, “yeah, he just left..” My jaw dropped. I asked if he said anything or if it appeared like he didn’t know that he still had makeup on. “He said to say sorry he couldn’t wait for you to come back from the bathroom but he had a great time as usual”. My face went white – I WAS GETTING MAKEUP WIPES FOR HIM, I told the receptionist. “Oh” she said, followed by a long drawn out “OHHHHH!” realising what had transpired.

To this day, I still don’t know if Robert* knew he was wearing makeup prior to his big meeting or if he did in fact secure the deal. All I know is that I never saw him again after that night, but I do hope wherever he is, he’s doing well and he knows that he’s still the prettiest 50-something year old man out there.