An Unexpected Opportunity

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.

"Mostly?"

"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 needing people?" I quietly asked.

"Yes. The hostess called me today asking if I knew anybody who might be willing to work. They are offering a $1000 bonus if we refer somebody who works 4 weekend parties." He said as he looked at me intently.

"Who gets the bonus?"

"I do, but I will split it with you if you decide to try it out." He said in a very hopeful tone.

"Do I have to have sex with people?" I couldn't believe I was asking this. How much was my dignity worth?

"No -- not if you don't want to. They will tell you to politely refuse and there are no repercussions. Two of the girls won't have sex. They get felt up a fairly often but they have never given in -- and they have been offered a lot of money."

"There are girls too?" I must have sounded amazed. I have assumed this was a gay orgy party for the ultra-connected.

"A few. Most of waitresses are gay twinks and cross dressers who look good in lingerie. Everybody wears the uniform though." Andy said with a grin while posing like a 50s dinner waitress. Andy was an extrovert and extravagantly gay.

He was lean, not too tall. Maybe five foot seven inches or so. I bet he didn't weight a pound over one fifty.

"Think they would take me? I am taller than you." Which was true. I am few inches taller but almost as skinny. When Andy drags me to a gay bar, I get hit up by the macho types all the time. I confess having drinks bought for me, getting my ass grabbed and the occasional drunken kiss was fun. I even went down on one really hot stud one drunken evening.

"You are smooth which is a huge thing. You have legs that go on forever and you have a lovely ass, if you don't mind me telling you. Hope that doesn't make you uncomfortable or anything." Andy said with a bit of a blush.

"Do I have to buy my own things?" wondering how I would even know what to buy.

"You need to buy your own shoes, but they supply everything else. They have a makeup girl who does your makeup and your wig. " Andy almost clapped he was so excited by the idea or for the money, maybe both

I needed the money bad. My bills were piling up. I had a car payment due soon and I had no idea how I was going to pay it.

"I will try it. Can you call them and see what they say?" I said, reluctantly.

"They will want to meet you first. Discretion is the most important thing. I had to sign some paperwork that said I would be sued if I said anything to anybody about the party or who attended. I don't know where the parties are held. A big blacked out SUV picks us up and takes us home. It's up in the hills someplace."

"Can you set that up for me?"

"Give me five minutes and I will let you know." Andy replied as he got up from his stool at the bar and headed outside to make a call.

I nursed my beer and wondered what I was getting into. Did I even want to do this? I am not gay but from what Andy said it doesn't sound like a gay only party. But I would be dressed like a drag queen. Who wants to see drag queens but old lady's and gay men? But the money sounded pretty good right now.

Andy came back in in less than three minutes.

"She wants to meet you. Now. She is coming down here. She will be here in about thirty minutes and will meet us at the corner" he said with just a hint of glee.

"Shit. That's fast. But what's the worst that can happen." I muttered loud enough for Andy to hear.

"You're going to like her. She is fair, takes care of her people and pays well. I made over $700 last weekend between pay and tips."

"What the hell. One more drink and we go meet her." I said sounding more positive than I felt.

A tequila shot and a beer later we left the bar and strolled over to the corner.

I felt a bit like a hooker. Standing on a corner waiting for some rich women to come look me over like a slab of beef. Though as I thought about it a bit of me wanted to be good enough. I didn't want to be rejected. I wanted her to find me attractive enough for her parties. That is my vanity talking.

A big black Mercedes pulled over to the curb. The back window rolled down and a deep, sensual voice said, "Climb in and let's chat. Andy darling, get in the front."

She was fashionable without being gaudy. Tall, pretty, slim and dressed in a business suit. The driver never turned around.

"Let's take a ride Mark. Don't go too far though." She said to the driver.

She turned and looked me up and down before she said: "I am Elaine. Who might you be?"

"Dan" I replied.

"Did Andy explain what the job is about?"

"Somewhat. I am serving cocktails to your exclusive clientele dressed in a uniform of a fairly immodest nature"

She laughed and said, "Pretty close. We strive to satisfy some of the most upscale and demanding people in Los Angeles. Knowing what you know about Hollywood I am sure you understand what that implies."

"Are you gay" she asked.

Here it was, crunch time.

"Not gay, but I have been with a few guys. I might be bi. I have no problems with gay sex, but I haven't really been attracted enough to try." I said trying to control my nerves.

"Good enough for me. Let me give you some more details." She replied.

"Dressed as our wait staff are you can expect to be touched, fondled and propositioned during the evening. You can expect this attention to come from both men and women. You can decline any advances as long as you do so politely and respectfully. If you are harassed let me know and the harassment will end. Keep in mind that there are often very generous tips that come with the more personal services you may choose to provide. It is strictly up to you. If you choose to indulge a guest's request there are rooms set aside for more private activities. Your name is never revealed. We provide discretion for our clients and our staff. Wait on our clients with a sense of fun, do your job well you will be well compensated. Our base pay per party is two hundred dollars. Guests are encouraged to tip generously so it's feasible you can make over $1000 by simply doing your job with a smile and letting them enjoy the unusual attire our wait staff is known for."

"That's comforting to know. I need the money and I do like attention. Do I fit your staff?" I asked.

"Take your shirt and pants off. Keep the underwear on" she said in a very businesslike tone.

I unbuttoned my shirt and pulled my pants off, kicking my shoes off as I did. I felt odd. I was being inspected like a horse. Is how aspiring actresses feel when they audition for parts.

"Not bad at all. You have very little hair, though you will have to shave your armpits. OK -- off with the shorts too."

I wasn't expecting that. I hesitated.

"This is business Dan. I am not interested in you sexually and I am not making porn movies. But it is good to know what you have to understand what will fit you properly." Said in an almost clinical tone.

I lift my butt up a bit and pulled my Joe Boxers down. I heard Andy turn around in the front seat. She flicked a button, and a dark window went up between the front and back seat.

"This isn't a show" she said as the window closed.

I was impressed. She didn't have to do that. But it illustrated how professional she was.

"You will need to fully shave down there. Our uniforms don't look right with a lot of hair poking out. But we should have no problem fitting you. What size waist do you wear?" She asked.

"Twenty-eight or thirty."

"How tall?"

"Five nine, or there abouts" I replied, sitting up a bit in my seat.

"You can get dressed. Have you ever worn high heels Dan?" I wondered if she kept a clip board with these questions.

"No" I replied honestly.

The dividing window went down.

"Andy, can you help Dan get accustomed to wearing four-inch heels before Saturday?"

"I don't have any heels at home." Andy replied

"What is your shoe size?" she said looking down at my feet.

"Eight slim" I replied. I was always a bit embarrassed about my small feet.

"Perfect. Shop for a size nine and a half or 10. Black closed toe pumps will be fine. Don't buy cheap shoes, they will hurt a whole lot worse than good ones. Shave where we talked about and do your legs while you're at it. Get a pair of thigh high sheer to the toe stay up stockings and practice getting around. I don't want you falling over with a tray full of expensive glassware."

"I guess that means I have the job?" I asked.

"You have the job if you want it." She popped open a briefcase at her feet and handed me some paperwork.

"This is our non-disclosure agreement and a description of the job along with our rules and requirements. You will have to sign each. We offer workers comp if you should get hurt on the job, though we have never had anybody get hurt. Sign the forms and bring them with you Saturday. Forget them and you won't work, and we won't ask you back. Andy knows where to meet our driver. Be ready by 3 PM. I am looking forward to working with you Dan."

The car stopped in front of our apartment. The interview was over. I got out and her car pulled away.

"Is she always like that?" I asked of Andy.

"Pretty much. Its business to her. But she protects her workers. I have seen two men and a women escorted out and never saw them again after they got aggressive with the staff. Elaine and two very well-built guys in suits appeared inside a minute and got them out quickly and quietly. A car was waiting` and they were taken home. You can expect to be touched, your ass massaged, touching on the arms or chest or thighs, but they should never grab you. Guys like that make everybody uncomfortable. A quick response informs everybody the rules will be enforced and that the party will be social, relaxed and without issues."

The next day Andy took me shoe shopping. We went to consignment shops and Goodwill.

"Ohhh -- I love these" Andy cooed as he pulled a pair of black heels with an ankle strap.

"They look awful tall" I said.

"Four and a half inches honey. Every bit helps your legs look sexier and your butt look tighter. Remember it's all for the tips. Besides, you will look divine in them" Andy looked my legs over slowly as he spoke.

"What about these?" I held up a pair of black shoes with a little strap over the instep and really low heels.

"Honey -- this isn't a grade school dance. Mary Janes are not what we are looking for." Andy said as he looked at the shoes in my hand as if they would infect him.

"Got just what you need Dan." Andy proudly displayed a pair of black heels, very tall, fairly plain but with a long toe.

"You must try them on Dan."

"Here? There are people around" I protested.

"Baby, this place is a drag queen shopping center. Nobody cares" he said as he held a tiny pair of what looked like stockings just to cover my toes and heels.

"Now put these on and try on both pairs" which Andy emphasized with a gently shove into the chair behind me.

I kicked off my kicks, put the little socks on and put on the pair Andy showed me second. My feet went right in and weren't tight. Then I tried to stand.

"On your toes honey. Stand on your toes" as Andy demonstrated by getting up on his toes.

I tried that. It worked, helped me to stand.

"Perfect. Try on the other pair. They are only five and six dollars. We can get both."

We bought both pairs and went home.

I spent almost all my time in the apartment in the shoes to get used to them. In time I would walk reasonably well. I even learned to put one foot in front of the other like I was walking a line. Even a bit of a cross over. I saw models do this on the runways.

Friday came around.

"All smooth Danny boy?" Andy was clearly excited for tonight, mostly to watch me become a crossdressing sex object.

"Yes. My legs and pits feel weird shaved. I don't notice my chest, but there wasn't much hair there to begin with."

"You are going to be such a hit Dan. They are going to adore you. You will have to bring a backpack to carry your tips home" He grinned.

"We are getting picked up at 3. Since you have never been there before they need time to get you ready and some instructions." Andy said packing up a bag.

At three the car pulled up, a very expensive SUV with black out windows.

We drove for over and hour and with the windows totally black out there was no way I would know where we went, how we got up in the hills or where we stopped.

The door opened and to guys who looked like weightlifting special ops guys in perfectly fitted suits held the door. I looked as we walked. Somewhere in the hills, and the place looked like a resort it was so big. A side door opened and in we went.

A woman, friendly and bubbly, met us.

"Good to see you, Andy. And you must be Dan. I am Megan. I will be getting you ready for the evening since tonight is your first time with us." She said as she held out her hand.

She led us into a room that was a well fitted beauty parlor. Chairs, mirrors, nail stations, pedicures -- she had it all.

"Take off everything. We will start by making sure you are as hairless as our guests expect you to be" Megan said as she busied herself at the counter.

I did as Megan instructed. Pants, shoes, shirt all came off. I waited for my next instruction.

Megan turned, looked at me, "The boxers too Dan. I mean naked as the day you were born. You're not the first naked man I have seen and won't be the last. I hope." She sighed.

I dropped the shorts.

Megan made the finger motion and I slowly turned for her. She inspected me thoroughly. Ran her hands over my pits, my chin and examined my balls. I confess I got aroused as she fondled me. But Megan paid no attention and moved on with an almost clinical demeanor.

"Not bad Dan. You did pretty well but we will finish you up." She said as if she were appraising a dog about to be groomed.

For the next two hours I was waxed, shaved, powdered, polished and colored. A wig, same color as my own hair, straight with a bob and front bangs was identified as right for me. As we finished up my nails were done in a modest pink, toes to match.

"Go get your uniforms on, let me see your shoes." Megan instructed. I held out both pairs. She picked the taller pair. "Perfect" she remarked.

Still buck naked I followed Andy to a very nice dressing room. Each locker had a name on it. I saw Andy's looker and mine was right next to it.

I opened the locker. Folded neatly on a shelf was a tiny thong, a small bra and a small wooden box. Opening the box I found a pair of dangly ear rings, a few rings of various sizes and a black ribbon with a little medallion on it.

I held the ribbon with the medallion and looked at Andy.

"It's a choker. Turn around" Andy said as he took it from my hand.

He ran it around my neck, adjusted up a bit and tied a bow in the back. The medallion was dead center of my throat.

"Helps cover the Adam's apple" he stated in a rather matter of fact tone.

I picked up the thong, which was silk, or satin that rode high on my hips with a bit of a silky black pouch in the front. I pulled it up my legs and positioned it the best I could. I could feel the thong pressing against my hole. It felt a bit stimulating. That was a different sensation for me. I have been with men but never had any interest in having my ass played with, but the thong felt really sexy.

I picked up the bra -- it was all strings and tiny cups. I tried clipping it in the back but I was just hopeless at it.

"Hold on Dan" Andy said as he got behind me and did the little hooks into the little loops.

He helped me adjust it so the straps were flat and the cups were positioned over my nipples, though they barely covered them.

There was a garter with straps hanging down. It seemed I should put that on before the stockings.

"Sit and put your stockings on. Watch me" Andy said, noticing my uncertainty.

He took the stockings out, sheer black with a kind of rubber around the tops. He took one stocking and using two hands rolled it up till the toe was all that was left. He pulled it on his foot, pointing his toes and slowly worked them up his leg making sure the heel was in the right place. I watched him do the other before I tried it.

It took two attempts on my right leg before I got it right. The left was easier now that I had practice.

Slipping into my heels I stood and looked down.

Isaw a full length mirror and strutted over.

Fucking hell -- I was hot!! Black heels, stockings the garter, panties and bra. My hair was just so sexy and my earrings and rings made me look like a flat chested model!!

"Oh honey -- you're going to be so busy tonight" said Andy as he stood behind me looking in the mirror.

"Wait till your makeup is done. You are going to be the hottest gurl here." Andy said in a very sultry voice.

Other wait staff were coming in to get ready and I got all kinds of complements. They were all very slim, and I noticed their eyebrows were done and nails were already done. As they got dressed I realized how androgynous they would be. All were obviously guys but dressed as sultry, hot hookers. The locker room was filled with sexual tension.