New Years’ Eve – The Roaring 20’s Return

A few weeks before New Years’ Eve, a friend of Christie’s approached her with an offer.  A few years ago, Christie had tended bar at a charity event.  One of the women she met, Debbie, owned the company that did the catering.  Debbie’s company was hired to cater a large New Years’ Eve party, and she asked Christie to help with the bar like she did at the charity event.  It would mean working New Years’ Eve, but the pay was excellent, and the party sounded fun, so she accepted.

The party itself was in Laguna Beach, at a huge house on top of a hill, with amazing ocean views.  Christie toured it with Debbie and told me that it was amazing.  The entire west side of the house was floor-to-ceiling windows overlooking the ocean.  It was really sparsely furnished, as it was mostly used by the owners for entertaining.  The catering company would supply everything, so all Christie needed to do was staff the bar for the night.

Christie got Lexi, the woman who helped her at the bar for the charity, to agree to join her and mix drinks.  Lexi really was an excellent bartender.  She also got two friends of hers, Meghan and Shawna, to help with cocktail waitressing.  I knew that was what she had in mind for me, too.

Christie and Lexi wanted to make an impression, in the hopes of getting more work from Debbie.  They decided we would all show up to the house ready to set up the bar.  We would all wear black leggings, black tank tops, and hoodies.  After we were set up, we would change into our serving attire.  The house had a room designated as a break room, and it had its own large bathroom with a makeup mirror.

The bartenders, Christie and Lexi, would wear black pants, white shirts, with a skinny black tie and suspenders, along with black fedoras.  The waitresses, Meghan, Shawna and I, would wear royal blue minidresses.  Lexi had found them at a local women’s discount clothing store – the kind you see in strip malls.  Christie had provided the sizes.  They were sleeveless, quite short, and had a bit of fringe the color of the dress that added a little length, but still let the shortness of the dress show through.  We would wear nude fishnets, black pumps with a low heel,  We also had the old-fashioned “cigarette and candy girl” trays to carry our drinks.  Meghan made us three pillbox hats of the style cigarette girls wore, in the same blue color as the dresses.

Christie and I drove down to the house together on New Years’ Eve.  She had reminded me to bring my makeup bag, in case we needed a touch-up after setting up the bar.  When we arrived, the caterers were already busy.   We found the bar area, and started by dressing up the bar with black linens.  Lexi, Meghan and Shawna arrived shortly after us, within a few minutes of each other.  Lexi remembered me from the party a few years ago.  “Hi, Gee!” she said, after hugging Christie.  She gave me a hug, too.  “It’s been too long – like, five years?”

“It’s good to see you, too, Lexi.” I replied.  “I had so much fun that night.”

“I know,” Lexi added with a smile.  “I heard you went home with that friend of yours,” she whispered to me.  I blushed.

Meghan and Shawna gave Christie hugs, and introduced themselves to Lexi, then to me.

“Hi,” I said, trying to keep my voice from giving me away. “I’m Gee.”  They both shook my hand, and turned to Christie,

“Weren’t you going to bring a guy friend of yours, too?” Meghan asked Christie.

“She did!” Lexi giggled, giving me a big hug from the side and kissing me on the cheek.  I blushed again.

Christie kept working at setting up the bar as she replied.  I took my cue from her, and kept working, taking bottles out of boxes and setting them up along the back bar.

“Gee and I have known each other forever,” she told the others.  “We both kind of suddenly realized that Gee would make a great girlfriend.  I suppose it started with a dare, but here we are.”  Lexi, Meghan and Shawna also kept working, setting up the bar.  We had all shed the hoodies and were working in tank tops.  In about thirty minutes, Lexi and Christie were happy with the result.  “This looks perfect, ladies,” she said, “Time to change.”  The caterers were still busy setting up, so we wold have the break room to ourselves.  We had a half hour before the guests would start to arrive.

It was intense for me, I should say, being in a room of four other women taking their clothes off.  I concentrated on getting my own “uniform” on, and tried not to stare.  I was in my thong, fishnet tights, and bra, when I noticed Shawna helping Meghan with her outfit.  Both of them were wearing just their tights and panties, and Meghan was applying tape to Shawna’s chest, to make her breasts push up.  She noticed me watching.  “It’s called ‘Hollywood tape,’ she explained, “and it helps you pump up your cleavage.”  She finished with Shawna, and pulled her chair over to me.  “Let’s see what we can do.”

She had me take off my bra, revealing my silicone enhancers. She kind of ignored them, and asked Shawna to help her.  Shawna got behind me.  “I’m just going to hold your breasts up a bit, babe.”  As she did, Meghan ran the tape below my breasts, pulling them together and a little bit upward, creating some cleavage.

“Perfect,” she said.  Before I put my bra back on, she applied some makeup to the area between my breasts, subtly highlighting the cleavage.  She had me put my bra and enhancers back on.  The effect was amazing.

I put on my dress. Meghan and Shawna and I helped each other zip up and fasten the backs, and Meghan got out the hats she had made, and pinned them in place with bobby pins.  Christie and Lexi were dressed and ready, too.   I felt comfortable with the women, but now it was time to go to work.

The five of us went back to the bar.  We met our busboy, who would help keeping us stocked up on ice, and clear away dirty glasses.  Debbie was pleased, which made Christie and Lexi happy.

As we waited for the guests to arrive, Meghan, Shawna and I started chatting.  They asked me how long I’d been dressing up as a woman.  I described how it all started as kind of a dare, almost six years ago.  Six years – I couldn’t quite believe it myself.

“Well,” said Shawna, smiling mischievously, “I’d do you, and I’m a lesbian!”

The guests started arriving soon after, and the house was quite full very quickly.  Christie and Lexi were busily mixing and pouring, while Shawna, Meghan and I moved around the room with trays of champagne.  If anyone noticed me, they didn’t say anything.

At midnight, the crowd made the “Happy New Year toast, the balloons dropped from a net hung under the ceiling, and the party went on.  By about two in the morning, the crowd started to thin.  We were still carrying our trays of drinks around, when a woman stopped me.  She was about 40, very attractive, and wearing a very sexy black dress.  It was mid-calf length, but had a long slit on one side well up her thigh.

“You are looking good tonight, honey,” she said, as I handed her a glass of champagne.  I thanked her, and she put a $100 bill on my tray for a tip.  I thanked her again.  “I don’t mean to be rude, ” she said,” but I’m curious – do you do this full-time, or is this something else?”

“I don’t live full-time as a woman, no,” I replied.  “I do dress up quite often, though.”

“Well,” she said, “You look great.”  She took her drink and headed over to a small group of men and women.  I desperately wanted to sneak a look, to see if she was telling them about me, but I didn’t dare.”

The party ended at three, without any further excitement.  The catering company took care of all the clean-up, so Christie, Lexi, Meghan and I were free to leave.  We hugged goodbyes, gathered our bags, and walked out to our respective cars.  I think we all wanted the night not to end, but it had turned quite chilly, and we all reluctantly got into cars and headed home.

Christie and I talked on the drive home.  She decided to stay at my place that night.  We were both exhausted, so we undressed, washed off most of our makeup, and crawled into bed.

“You were amazing tonight, Gee,”  was the last thing I heard.



2 thoughts on “New Years’ Eve – The Roaring 20’s Return

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s