My Job Tried To Promote Me From Bellhop Boy To Cocktail Waitress!

I remember in my experimental "makeup" pre-transition phase where I worked as a bellhop at at well known chain hotel during college and I was wearing a little bit of makeup, especially playing with foundation, faint eyeliner/shadow, blotted lip-gloss, all making me look fairly "feme cute" for a guy but not overly girly. Customers didn't seem to mind so I felt hotel personnel won't as well, and besides that look sure beat my old plain teenage boy-look (I was 19, slim, and small boned).

I usually went about my normal duties serving hotel guests (room service and moving broken TVs around a lot), occasionally helping in the restaurant when needed, but rarely had anything to do with the small cocktail lounge next to the restaurant which had a small band on the weekends, but I loved hearing their pop-style music that the bands were asked to play.  Management was always trying to promote the lounge in order to help increase revenues especially during the periods when the hotel side was slow, given occupany was based mostly traveling salesmen and the key activities of the college where parents and families came to visit their student kids, such as with football games.

I had decided to experiment and let my hair had grown out to shoulder length and apparently my more subtle feminized "look" I was soon to discover had gotten some notice by the management team who were on the slightly more conservative side -- two men and an assistant manger woman.  One day were all sitting together then suddenly one of the men asked me if I wished to work some in the cocktail lounge helping out. I said yes ..sure! ....figuring it would be to bus tables, stock, or help with tasks around the small stage band.  That would be a nice break from the bell-hopping and helping washing dishes in the restaurant when it got very busy.

And besides I could be around the cute cocktail waitresses in their very short sexy outfits, the tight gold-colored ones with the puffy short sleeves, short flaring out built-in skirts and the white rumba/lace thick panties showing through a big cut-out in the rear (no doubt to tease the male drinkers who then wouldn't be tempted to drink and leave if things were slow that evening).  Yes, this could be a nice side-area distraction for me to start working in!  So then without any further comment the assistant-manager woman  manager immediately took me to her office so I could get my lounge uniform (I figured they had some sort of short man-style jacket for male helpers) and then showed me the uniform I would be required to wear, and was I in for a big surprise!.

My jaw practically hit the floor, and I stammered "what? ...that ...that uniform can't be for me! ... I whined ...I expected some sort of man's uniform!"  She replied "no Chris, this is the one you would be wearing, and you can start working tonight!" ....holding up a brand new exact same girl's cocktail uniform like what all the real girls wear while serving all the horny guys!  Then it fully hit me! ...they were asking I work as a cocktail waitress!  Yikes! This is not what I expected!   I told her that I changed my mind and backed out of the office and got out of there fast!  Whewww! ..that was a shock.

But secretly, later on, I got a little thrill from the thought of wearing that girly uniform and if I had been in transition-to-a-girl at that point in my life I would have loved to have done so.   And I noticed in passing by when the woman assistant got back to the two manager's table in the restaurant portion they all seemed to get a big laugh from my misinterpretation of their true intent .  I got ribbed about it now and then afterwards, as well as by the front desk staff.  I laughed it off, but they had played a pretty big trick on me.  I tried to as well, but no amount of explanations about how I thought they meant a man's uniform would stop their kidding me now and then.

I suspect it was all a big joke to begin with, perhaps to poke fun on or shame me about how girly my face had started to look, so rather than come out and comment they just decided to have some fun at my expense to make their point.  I don't think they would have actually let me work in the lounge so prettily dressed (was an age 21 drinking state so all wait and bartenders have to be at least 21 as well I believe), but they might have let me get all dressed up in my cocktail uniform first before telling me it was all meant as a joke!  And I'd have died of embarrassment when they laughed at me then and informed me they were really just joking.  That was indeed a close call!

And yet I eventually DID wear a cocktail waitress uniform to work one day! ...years later and at another type of job, where as my then "woman's clothing saleswoman" job in a big department store we had "dress in a outfit of our choice" day for all employees and staff, and I chose to wear a cocktail uniform I had managed to find in a thrift store that was nearly as cute but without the skirt cut-out in the back.  But that time I looked the cutesy part very well, even my freshly grown breasts were bulging out of the low-square cut front!  See what a joke can turn into once it's followed to it's logical conclusion?!!  LOL!  And now for years I get to wear a dress or skirt to work every single day.  So I ended up going from bellhop boy, to sweet sales girl!  

And maybe some day I will return to that same cocktail lounge and apply as a cocktail waitress incognito.  That would be my sweet revenge!