1. An Unexpected Opportunity

    Date: 3/16/2023, Categories: Trans Author: byjim_janes, Source: Literotica

    Money was tight. Working as a waiter paid the bills but didn't leave much left over. Andy, my roommate, was always paying on nights out. Working at the same restaurant as I did, I knew he wasn't making significantly more than I did. And Andy's gay lifestyle constituted a lot more clubbing than mine.
    Andy came home after a night out and I could see makeup on his face which was smeared up making him look like he had a very hard night. Being drunk as well I just helped him to bed. He got up late the next day came into the kitchen, grabbed a coffee, and slumped into a chair.
    "Where do you earn that extra money, you always have?" I asked Andy.
    He took a long draw on his coffee and then looked up at me over the rim of his cup with a curious, whimsical smile on his face..
    "I have a gig with a catering company that does unusual party events. The pay is very good, but the uniform is pretty outrageous" he replied quietly as he stared at his slippers.
    I pondered what would make him suddenly embarrassed. Andy was a flamboyant gay and when he said the uniform was outrageous it boggled my imagination what kind of outfit would cause such a reaction.
    "Like what?" I said looking away, trying not sound like I was interrogating him.
    "You sure you want to know?"
    "Sure. Why not?" I muttered into my coffee cup.
    "Well, it's a girl's wig, makeup, panties, garter belt, stockings and high heels." He giggled as he said this.
    "Seriously?" What kind of parties are we talking about?" I asked.
    "The events are for very wealthy, kinky couples, celebrities and others who are well connected -- Hollywood types. They are very discrete, and the parties are invitation only. Invitations are hand delivered and if the guest accepts a limo picks them up at the door. They do not know the location of the event. They just arrive and enjoy the exotic distractions and are delivered home safe and sound. "
    Andy paused and while looking into his cup as he quietly said; "They are always looking for serving help."
    "What exactly do you do at these parties" I asked, thinking it sounded like an orgy to me. Not that I am opposed to an orgy mind you.
    "I serve cocktails -- mostly" he said.
    "Well, there are occasions when extra services are requested." Andy had that mischievous grin he had when he was talking about sex.
    "They need help. There is a party this Saturday and they mentioned they needed extra wait staff." Andy said in a muffled but excited voice.
    "Not my thing. I like my clothes on when I work" I replied.
    Andy just shrugged and I let it pass.
    The week was passing and business was slow. Customers weren't eating out as much and the tips were smaller when they did. My tips were dwindling down so much that my take home pay was subsistence level. It was Thursday and the weekend was fast approaching.
    After work Andy met me in a bar that caters to restaurant and bar workers.
    "Were you serious about that alternative party gig ...