Tag Archives: sissy

The Poker Game

Early in March, before we were all sheltering in place and working from home, I ran into my friend Ed.  I wasn’t planning on being out long, so I had just done some minimal makeup, put my hair into a ponytail, and put on some jeans, and a white tee shirt.  Christie had texted earlier and said to “wear white,” meaning we would both be wearing matching white bras and panties.  The white bra was clearly visible through the shirt, and it was drizzling, so I added a thin white sweatshirt top.  My nails were a subtle pink shade.

Ed and I have known each other since school, but hadn’t really kept in touch.  A few years ago, I was cocktailing for Christie at a charity event and he recognized me. We’d gone out once after that.  He was a nice guy.  I’m not sure how I would describe our relationship.  He knew about my becoming Christie’s “girlfriend,” and seemed supportive.  We were friends.  He definitely wasn’t gay, but we’d had sex twice, once after the charity event, and once after we’d been out for drinks.

Ed asked me what I’d been up to, and if I’d gone out or done anything fun lately.  I replied that it had been pretty much just work, but I did tell him about New Year’s Eve.

“That sounds like a fun time,” he said.  He was disappointed that I didn’t have pictures.  I’m terrible about pictures.

He went on to tell me about a group he’s been playing poker with.  It was a monthly game, rotating between the players’ homes.  One guy hosts, and another supplies food and drinks, he explained.  The next month, the food and drink player hosts, and another player brings refreshments, and the rotation goes on.  He asked me if Christie and Lexi would like to supply the food and drink.  “You could be the waitress,” he added.

I started out with an “I don’t know, Ed,” but he persisted.  It was his turn to supply food and drink, and he was tied of the same old chips and salsa.  I agreed to ask Christie, although I knew what she would say.  “But me waitressing…how would you explain it?  In a big group, like those big events, it’s easy not to get noticed.  Most people are too into their own fun.  This seems pretty obvious.”

“I’ll just say I won a bet with you, or something.  Please? Ask Christy, ok?”  he begged.

Christie, of course, was enthusiastic.  She checked with Lexi, who really did most of the organizing work, and over the next week, Lexi and Ed worked out the details.  It wasn’t a large group, just the seven players and maybe one or two stand-by players.  Lexi, Christie and I would set up the food and bar, but then they would leave.  I was to do the serving.

On the day of the game, Christie came over to my place to help me get ready.  I had showered, shaved my body, and washed my hair.  Christie helped me do my hair in loose beachy waves.  She also shaved my back and shoulders, just to be sure they were smooth.  Then she did my makeup and nails.  I do my own makeup most of the time, and it was quite a treat to have Christie do it.    She laid out the clothes I would wear – a short black skirt, a black halter-style tuxedo top with a bow tie, black pantyhose and a pair of low, black heels.   She loaned me one of her bras – a black halter-style lace one – so the straps wouldn’t show under my top.  I chose a black lace thong that almost matched the bra.

She drove me over to the host’s house.  The host, Hal, met us at the door.  He stared at Christie and me for a minute, and then greeted us.  “You must be Christie,” he said, reaching out to shake Christie’s hand.  “And you must be Gee.  Damn.  Must have been a hell of a bet!  Come on in.”

We came in and found Lexi in the kitchen, setting up the food.  There were a few steam trays of hot food that I would have to pass around, some other things set up buffet-style, and a bar area.  The house had a very nice wet bar.  Ed had let Lexi know what drinks the players liked, so she had arranged all of the fixings for me.  Earlier in the week, Christie had made sure I knew how to make the drinks and practiced each one.

Ed was the next to show up.  After we all greeted each other, Hal congratulated Ed, speaking to all of us.  “I don’t know how you set this up, but this is amazing.  The food and drink looks great – way better than the usual snacks.  The bar set-up is fantastic.  And, I don’t know how to say this, but your waitress looks fine!   I don’t even want to know what the bet was!”

Everyone laughed, at that, and Hal went to greet the players as they arrived.  Lexi and Christie hugged me, asked if I had any questions, and got ready to leave.

Christie pulled Ed aside.  “Take good care of her, ok?”  she asked, looking at me.

“Of course,” replied Ed.  Lexi and Christie left.

Ed looked around the room.  We were alone.  “You do look great,” he said, holding my hands.  “Just relax.  These are alright guys.  Hal told everyone it was just a bet between us, like I told him.  You’ll do fine.”

The players were starting to show up, so I grabbed a tray of various snacks and went out to the front room.  Most of the remarks were directed toward Ed, about how he really outdid everybody else as far as food and drink.  Ed shrugged it off, saying “I know some people.”

I eventually got everyone situated with food and drink.  The host moved everyone to the table, and things got a little easier.  The players concentrated on the game – they were very serious – and the two stand-by players just watched.  I refilled drinks, occasionally bringing more snacks, too.

I hung back by the stand-by players, waiting for someone to need a refill.  One of them, Tony, leaned over to me.  After making it obvious he was looking me over, he asked me “so, Hal says you’re a dude.”  The other stand-by player snickered and shook his head.

As quietly as I could, I replied “Yes, I’m…a dude.  But tonight, I’m serving drinks.”  I walked back to the bar.  Some of the players’ drinks were running low.

Eventually, one of the players cashed out, and Tony took his place at the table.  As I was making a round of the table, I felt a hand up my skirt.  Tony had slid his hand well up my leg and onto my butt.  “Excuse me,” I said, stepping back.  The other players looked at Tony.

“What are you doing, man?” asked one of the players.  Tony quickly produced a few dollars and said he was trying to put a tip into my stockings.

I set Tony’s drink down.  Hal looked at him for a long few seconds, and said “let her alone.”  The players all stared at Tony, and he eventually put the few dollars onto my tray.  I thanked him.

I finished my round of the table, and went back to where the other stand-by stood, then back to the bar.  The other stand-by followed me.  He introduced himself as Barry.

“Don’t be mad at Tony.  He’s not a bad poker player, but he’s kind of a jerk.  You do look really, um, amazing.”

“Thank you,” I replied.  “I wasn’t sure about doing this, but Ed and I made a bet, and I thought ‘If I’m going to do this, I have to do it right.  So I got my friend Christy to help me.”

“Yeah, I’m not really sure how to say it.  I mean, I know you’re a guy, Ed’s friend.  But you do look…hot.  If I didn’t know, I wouldn’t have guessed, I guess.”  He was nervous.

“Thank you, Barry.” I said.  “I appreciate the compliment.  We spent a lot of time on all this, and I’m glad it seems worth it.”
“And it was just a bet?” he asked.

“This part of it was a bet,” I replied.  “I should get back to work.”  I made my way back to the table.

The game broke up after a few more hours.  It was well after midnight.  A few of the players left me a tip as they left.

I was in the kitchen, finishing the dishes, when Hal and Ed came in.  Hal was pleased.

“That was absolutely the best.  You were great, by the way,” he told me. “You really know how to do this.  We were a little worried it would be too much of a distraction, you being our waitress, but you were perfect.”

I thanked him.  Ed looked at me.  “Ready?” he asked.

“I’m ready.  Thank you, Hal.  I’ll pass your compliment along to Lexi and Christie.  We really appreciate the opportunity.”

We headed toward the front door.  Ed reached it first, and opened the door for me.  I smiled and thanked him.  As we walked to Ed’s car, he offered me his arm, which I kind of instinctively took.  We reached his car; he opened the passenger door for me, and helped me in.  I noticed Hal was watching from the porch.

We made small talk on the way home.  Ed complimented how I looked and how I managed the food and drink.  He handed me an envelope.  “It’s from the guys.”  He explained that everyone decided to put in a percentage of their winnings, if they had any.  There was a lot more there than I expected.

We arrived at my place, and Ed jumped out of the car to open my door.  He walked me to my door, where I invited him in for coffee.

We sat on the couch for a few minutes and talked.

Ed leaned over and kissed me, stroking my thigh with his hand.  I didn’t quite know what to do with my hands, so I just put them in my lap.  To my surprise, he reached under my skirt and began to rub me.

A few minutes later, he stood up and led me to my bedroom.  I sat on the edge of my bed, undid his belt and fly, and reached into his pants, pulling out an enormous cock.  I leaned down and put it in my mouth.

“God, that feels amazing.  How did get so good at this?”  he said. I told him how Christy had taught me.  Ed stood me up and undressed me slowly.  The he gently slid me back on the bed, pushing my legs apart.  I felt self-conscious, but managed to reach to my nightstand and get a condom and lube.

He positioned himself between my legs.  I was worried about how big he was, and hoped he would go slowly.  He held my ass and hips and worked his way into me.  It was intense.  I thought of how my first time with Christie felt weird and a little frightening.  It’s something feel it through my entire body.  I describe it a tight sensation in my throat, like what you feel after a bad scare.  But it’s an exciting feeling, not scary at all.  It kind of spreads out all the way to my fingertips and toes.

I felt Ed’s body tense just before he came.  When he withdrew, he took off the condom.

“What should I do with this?” he asked, grinning.  Remembering what Christie likes me to do, I opened my mouth.  That surprised him, but he emptied the contents onto my tongue.

We lay down on the bed and cuddled, and I fell sound asleep.

I had no idea how late it was when we fell asleep, but it was nearly 9 am when I awoke.  Ed was gone, and my phone was alerting me to a message.  It was Christie.

“Let’s wear blue today,” she texted.

My Christmas Present from Christy

Christy gave me the most amazing Christmas present this year.  Over the past two months, it has frightened me, given me confidence, and proved to me that I could do something I’d never thought possible.

She gave me a boudoir photo shoot.

It’s been four years since Christy decided I was going to be her girlfriend.  Over those years, I’ve gotten more comfortable going out as a woman, usually with her, but sometimes on my own.  I am always still a little apprehensive at first.  I still dress as a guy at work, even though I wear panties and a bra every day.  Only one of my work colleagues knows that, though.  So the thought of going to a professional photographer and having pictures taken in lingerie was not something I ever considered.  Christy guided me through it and nudged me along, and I have to say that the results were amazing.

Christy had done some research, identifying a couple of studios she wanted me to contact, and paid for the whole thing as her gift to me.  She insisted, however, that I do all of the work setting things up.  It was a lot more involved than I expected.

After contacting the studios, we settled on a local photographer who had her own studio nearby.  I emailed her first, expressing an interest in a boudoir shoot and inquiring about prices.  Not wanting any surprises, Christy suggested telling her that I was trans. We had a very long discussion about this, and in my email I did, asking if that mattered.  She replied with “Let’s do it!”

The next step was to go to the studio and meet the photographer.  We set up the appointment by email.  It was pretty warm, so I put on a pair of shorts and a white t-shirt.  I kept my makeup pretty simple.  She was really nice, and despite being pretty nervous, I found myself quickly at ease with her.  She explained how the shoot would go, what kind of outfits I should bring, and showed me how we would choose the pictures for the final album.  Finally, we chose a day for the shoot.  She recommended a couple of hair and makeup artists that she works with, and recommended that I contact them to set up an appointment.

The next step was more complicated.  Neither of the makeup artists that the photographer recommended were available on the day we had chosen for the photo shoot.  That was unfortunate, because the photographer had said both of them usually come to her studio for the appointment.  I needed to find a hair and makeup artist who could fit me in before my shoot.

With some help from Christie, I found someone close to the studio that looked promising.  One day, at work, I stepped out into our break area and called.  I was really nervous.  When she answered, I asked if she was available to do hair and makeup for a photo shoot.  The makeup artist, Michelle, asked what kind of shoot it was.  I replied that it was a boudoir shoot, in a studio.  Then she said,” do you have a model?”  I panicked.  Obviously, my voice had given me away as a guy.  “Um, no, I’m the model.”  After a brief pause, she said, “OK, what date and time were you looking for?”  I gave her the date.  She said she had a colleague who does hair, and she would ask if she was available.  She also asked if I had a picture of what look I was going for.  We traded email addresses, and I promised to send her a picture.  Later that day, I found a photo to send her.  It was actually from a website of hairstyles that Christy and I had been looking at.  The next day, Michelle confirmed that the hairstylist was available, and we booked the appointment.

Over the next two weeks, as the date of the shoot approached, I started getting things ready.  I made an appointment with my waxer, Brandy, and had my brows, back and shoulders done.  During the appointment, I mentioned the shoot.  She told me that she’s also done a boudoir photo session, but in her own apartment.  She recommended I get a spray tan, to cover up any flaws.  She also recommended I bring a corset as part of one of my outfits.  I didn’t get the spray tan, but I did manage to find a corset that I liked.

I gradually put together my outfits for the shoot.  I decided to keep things simple, and stay with black.  I selected a black thong, a pair of black lace boyshort panties, a garter belt, the corset, a pair of black bras, two pairs of black pumps, stockings and a black lace long-sleeved blouse.  As the photographer recommended, I put all of them into a small carry-on suitcase.

I’ll finish the story and share some more of the photos in my next post!

Keeping Up Appearances

Last week, Christie gently reminded me that it was time to schedule another brow waxing appointment.  I had been a little preoccupied with the holidays, and hadn’t gone since before Thanksgiving.  I try to keep up with trimming and shaping them, but they do sometimes get ahead of my efforts.

I had made my own online account with European Wax Centers, so it was just a matter of going online and setting up my appointment.  I checked out my regular shop, and found that my regular waxer, Shelby, was available on the upcoming Saturday, so I booked the appointment.

Christie also suggested we try something new.  She wanted to take me to a local hair salon and have my hair colored and trimmed.  I admit that since I started growing my hair out, I hadn’t gotten it trimmed very often – usually Christie just cleans up the uneven ends.  Coloring it was a new thing, though.  So I took off early on Thursday afternoon, changed into a pair of jeans and a t-shirt and sweatshirt, and met Christie at a coffee shop near the salon.

We walked next door to the hair salon, and Christie introduced me to one of the owners, Laura.  I felt a little intimidated.  Laura was attractive, about 30, very talkative and had short gray hair tinted with blue.  She sat me down in a chair, and with Christie standing next to me, asked “so, we’re doing a color and cut, today?”  Before I could answer, Christie chimed in.  “Like I mentioned on the phone, I think we want to go a little redder.  Not too much, but just enough to get more of a copper color.  What do you think?”  The two women conferred, while Laura pulled off the band holding my hair in a pony tail, and fluffed up my hair.

“I think that would look great with Gee’s complexion and eyes.  This will be fun.” She turned me around in the chair to face her, and adding “I’m going to go mix up your color, okay, babe?”  One of the salon assistants came over and asked if we wanted wine or champagne.  Christie asked her to bring two glasses of champagne, which turned out to be a pretty nice sparkling wine.

Christie sat in the empty salon chair next to me, and the three of us chatted while Laura applied the color to my hair.  She explained that she would color the roots, leave it for 30 minutes, then pull the color through to the ends, leave it a few more minutes, and then rinse out.  Other clients came and went, too, but the salon wasn’t too busy, so I felt pretty comfortable.  Christie and I waited and talked while the color was setting.

After Laura rinsed out the color, she led me back to the chair.  She explained that she was just going to trim the very ends of my hair, so the ends wouldn’t break off unevenly.  She put a little bit of product in my hair, which enhanced the curls of my already pretty wavy hair.

I looked in the mirror.  It took a bit of getting used to, but I liked the color.  It definitely gave my hair a reddish color, and the curls seemed very light and bouncy.

Christie and I thanked Laura, and left.  We went across the street to a wine bar.  Not surprisingly, the server greeted us with a cheerful “Hi, ladies.”  I felt a little self-conscious of me new hair color and style, but as we sat and enjoyed a few glasses of wine, I settled down.

When Saturday morning arrived, I dressed in my mesh-panel leggings, a tank top, and a white hoodie.  It was chilly, but promised to get warm soon.  I put on a bit of makeup.  More and more, I just don’t feel right without at least some makeup on, and touched up my nail polish.

I arrived at the salon and Heidi, the receptionist, greeted me.  She almost always worked on Saturdays, so I had gotten to know her pretty well.  She checked me in, and we chatted about plans we had for the weekend.  After a few minutes, Shelby came and got me, and escorted me back to her treatment room.  I mentioned to her that they had grown in a bit, since it had been so long since my last wax.  She waxed and trimmed my brows, occasionally letting me check in a mirror to see if I liked how they looked.  After she finished, she offered to fill them in.  I said yes, and she gave me some fabulously arched brows.  When she finished, she took me back out front, where Heidi, the receptionist, checked me out and made my next appointment.

Christie had some plans for us that evening, so I went back to my place to meet her, and get ready.

A Very Special Gift, Part 2

(Here’s what happened after Christie presented me with my vagina gaff.  I apologize for the delay, but this took longer to write than I thought.  Christie and I have an amazing sex life, but she seldom lets me write about it in detail, so I had to be careful about how much I revealed.)

Christie and I headed out at a local restaurant that we like, and sat at the bar.  It was fairly busy, but the bartender was attentive.  We stayed for about two hours, had some wine, and talked.  Christie seemed chattier than usual (which is something – she’s always really outgoing, but tonight she just seemed excited and talkative).  We left and went back to Christie’s condo.

We parked her car, and walked arm in arm toward her door.  A neighbor of hers was outside, waved hello to Christie, adding “you girls look so nice!”

Christie opened her door and we went in.  She immediately spun me around, pinned me against the door, and kissed me.

“Oh my god, it was so hard trying to keep my hands off you!” she whispered.  She took me face in both hands and kissed me again.  “Come on,” she said, as she took my hands and led me toward her room.  We undressed each other quickly, leaving her wearing nothing and me in just my gaff.  She caressed it.  She told me she could hardly think of anything else all night.

She sat me on the bed, facing her, and we kissed and caressed each other.  She was becoming obviously much more excited, when she wriggled closed to me, scissoring our legs together.  She pushed her crotch forward to touch mine, and began to rub against me.  We continued to kiss as she coached me how she wanted me to move.  I’d seldom seen her this turned on.  I was excited, too, despite being snugly “tucked” into my gaff.  I felt dizzy.

Christie’s rubbing became more urgent until she climaxed in the most amazing way.  We held each other very close for a long time with Christie occasionally giggling.

After a while, she reached into her nightstand and got her (“our”) strap-on.  I helped her put it on.  She pulled off my gaff, and sat down facing me again, wriggling close enough to push the head of the strap-on in.  She leaned me back and adjusted my legs so she could push deeper.  Her tummy rubbed against me.  Within a few minutes, her thrusting became more urgent again, and she shuddered as she climaxed once again.  In the process, I had, too.  She collected it on her index finger, smiled, and put her finger into my mouth.

We were both exhausted, and pretty much passed out in each others’ arms.  We slept through the night, waking on Saturday morning.  I hadn’t brought a change of clothes with me, so when we got up, I put on one of Christie’s oversized t-shirts.  She loaned me  a pair of panties.  We made coffee, cuddled on the balcony of her condo, and talked about last night.

We made some plans for the weekend ahead.  I put on my bra and did my makeup, and Christie gave me a pair of her shorts to wear home.

I am still stunned at how amazingly turned on she got by me wearing that gaff.


Co-ed Bachelor Party

Christie’s friend Allison invited her to a “co-ed bachelor party” last weekend, and Christie brought me as her date.  Allison’s brother was getting married, and most of their family lives on the east coast, so Allison took on the role of “best man.”  It was a small group, just six couples – Allison and her brother, another couple I didn’t know, and Christie and I.  Allison booked a limousine to take us to a casino a few hours south, near San Diego.  Everyone would wear tuxedos.

Christie was excited.  “Just think,” she giggled, “you’ll get to take me shopping, for a change,” as we headed out to rent a tuxedo for her.

Getting DressedThat Saturday afternoon, Christie came over and we got dressed.  There would be no change to any of Christie’s rules, so I showered and shaved my legs, arms and chest.  Christie shaved my back.  I touched up the polish on my toes, and applied a clear nail polish to my fingers.  Christie and I, as is our custom, wore matching black panties and bras, garter belts, and sheer black stockings.  The black bras showed through our white shirts, but weren’t visible once our jackets were on.  I was concerned about the stockings, but they did look like traditional men’s tuxedo socks, once our trousers were on.  We both wore small, diamond earrings.

Overall, the evening was fun.  Allison and her brother were nice, and the third couple, friends of Allison’s named Suzy and Dan, was fun.  Christie and I did quite well at the craps table, too.  Of course, as long as we kept gambling, the drinks were free.  Sometime after midnight, we returned to our limousine for the ride home.

The champagne continued to flow as we made our way north.  Traffic was heavy – even for Southern California – and it was taking forever to make progress.

Suddenly, I realized that Allison and her brother were talking about sex, strippers and bachelor parties.  Apparently, they had started this conversation earlier in the evening.

“All I’m saying,” said the groom, “is that stupid or not, it’s seems to be a tradition.  Every one I’ve ever been invited to had a stripper show up and embarrass the groom on his last night of ‘freedom.’  So to be a perfect bachelor party, we need a stripper to sneak the groom off and discreetly go down on him!”

Allison groaned, the third woman added a sharp “what??” and the groom shrugged.  “Just saying.”

The discussion stayed on the topic of sex.  The groom joked that all the talk of “going down” was making him horny.  “Don’t look at me,” laughed Allison.  “I’m the best man, and your sister!”

“Why does it have to be a woman?” asked Suzy.  “Guys are always saying that girl-on-girl sex is so hot, what’s wrong with guy-on-guy?”

I sat as quietly as I could as the discussion went on.  The groom objected, saying that he could never get off if I guy gave him a blow job.  Suzy told him “Look, don’t be such a baby.  If you really can’t get off, I’ll do you.”

“Whoa,” said Dan.  “Are you signing one of US up to do it?”

“Hell, yeah!”  You’d watch if us girls got it on, right?” replied Suzy.

“I don’t care who does it,” said the groom, “I’m getting horny with all this talk!”

Suzy proposed a game, to decide whether Dan or I would go down on the groom.  I started to say something, but Christie put her hand firmly on my knee.  Suzy’s idea was “boxers or briefs.”  Whichever of us was not wearing the same type of underwear as the groom would go down on him.  I thought I would have a heart attack.

The groom opened the waistband of his trousers and pulled up the top of his boxers.  Dan gave a victory shout, and revealed his own boxers.  Everyone looked at me, and I just quietly said “Not boxers.”

Christie squeezed my knee and whispered “relax, remember how I taught you to do it” in my ear, as Allison grabbed my wrist and pulled me toward the groom.  He still had his waistband undone.  Suzy was laughing and pouring champagne.  I was so scared, worrying about what people would think.  Then I realized that the groom had his eyes closed and his head tilted back, not watching me at all.  I crawled closer, and reached for his crotch.  He felt pretty large, and he was definitely turned on.  I looked back at Christie, who was watching me and smiling.  I reached into his pants and pulled out his rather large, stiff cock, and slowly lowered my mouth onto him.

I had only gone up and down on his shaft a few times, when I heard Allison saying “good job” and felt her rubbing my back.  I felt myself tense up, arching my back away from her hand in the hopes that she would detect my bra, but it was no use.  “What are you wearing??” she said.

I tried to stop going down on the groom, but he held my head firmly down.  Christie spoke up.

“That was my idea.  I told him that if I had to wear a men’s tuxedo, he’d have to wear underwear that matched mine.”

Allison giggled, set down her champagne, and started to pull of my jacket.  Suzy helped by tugging my sleeves over my hands one at a time.  Soon, they had my jacket off, clearly revealing my lacy black bra.  I heard Christie say “see?” as she opened her shirt, revealing a matching bra.  Allison kept going, reaching around my neck and removing my tie.  Soon, she and Suzy had my shirt off, and started to pull off my shoes and trousers, revealing my black lace panties, garter belt and stockings.

“I told you,” Christie told them.  “We’re both wearing the same things under our tuxedos.”  She laughed, and poured more champagne.  She went on, adding “doesn’t he look cute?  He’s got such a nice ass and nice legs.”  Allison and Suzy giggled, and Suzy ran her hands across my hips and thighs.

“His legs are shaved!  And he certainly knows what he’s doing,” said Suzy.  Then she asked me “are you sure you haven’t done this before?”  I couldn’t answer – the groom held my head firmly in place – so Christie answered for me.

“I taught him everything he knows,” she said.

Suddenly, I felt the groom tense up and seconds later, he exploded in my mouth.  He let out a groan of pleasure, and I heard Allison, Suzy, Dan and Christie cheers and clap.  I sat back on my feet, and Christie handed me a glass of champagne.  “That’s my girl!” she giggled.

Suzy said “you know, whenever I give Dan a blowjob, I have to fix my lipstick.”  She laughed as she pulled some bright red lip gloss out of her purse, leaned over and applied it to my lips.  “There you go, sweetie.”

I moved back and sat down next to Christie, reaching for my clothes.  “No, you don’t,” she said, “you can stay like that for a while.”  She poured me some more champagne.  Allison and her brother started chatting, and I started to relax.  I crossed my legs and reached for the champagne.  That’s when Suzy noticed that I had no hair under my arms or on my chest.

“Did you make him shave everything?” she asked Christie.

“I did,” Christie explained.  “I like it when he knows what we put up with, and he looks so cute.”

“So, stripper-girl,” Suzy said to me.  “I feel like a lap dance.”

Christie and Suzy laughed.  Christie took my champagne glass and Suzy pulled me onto her lap.  It felt pretty sexy to be sitting on a very attractive woman’s lap, and I tried my best not to let my excitement show.  I gyrated and danced to the music playing in the car, with Suzy and Christie laughing all along.

After a few minutes, Suzy said “Ok, that’s enough.  Now it’s Dan’s turn.  She pushed me onto Dan’s lap.  I was surprised at how excited he was – as soon as I sat on his lap, I could feel his erection.  He slid down in his seat, and I danced on his lap, putting my hands on the roof of the limo.  I could feel him pushing back, and was again surprised when, within a few minutes, he grabbed my hips and came in his pants.

Suzy erupted in laughter, Dan seemed a bit embarrassed, and Christie pulled me back next to her.  She handed me my glass, and I took it.  I crossed my legs at the ankles and tried to disappear into my seat.

“He looks so feminine, sitting like that!” giggled Suzy.

“Isn’t she?” said Christie, deliberately calling me ‘she’ and patting my leg.  We were finally making progress toward home, and we approached my apartment, where Christie and I were to get dropped off.  I reached for my clothes.  Christie just handed me my tuxedo jacket, saying “Put this on.  We’ll just carry the rest.”  Christie took hold of my shirt, and pants, and handed me my shoes.  The limo stopped.  I was so afraid that someone would see us, but it was quite late – around 3 am – and I saw no signs of life.  Christie and I said our good-byes.  The groom was asleep.  Allison and Suzy blew kisses, and Dan gave a wave with his glass.

Christie and I walked in silence to my door, me in just a tuxedo jacket and lingerie, carrying my shoes.  I let us in and collapsed on my couch.  “Oh, my god, Christie,” I started to say, but Christie put her finger to my lips.

“Shhh,” she said.  “I’ll go make some coffee, you relax, and we’ll talk some.”

Helen’s Interview with Christie and Gina

(After my first “work day” at her office, Christie’s friend, Helen, invited me out for drinks.  We had a wonderful time, although I was nervous at first.  I had never been out with anyone but Christie.  Helen asked a million questions, and I did my best to answer them.  I spent a few more Saturdays at Helen’s office, working as her “office girl.”  This past weekend, Helen came over to Christie’s apartment, and “interviewed” both of us.)

Helen:  Christie, I’ll ask you, first.  How did this start?

Christie:  I’ve known G (it’s pronounced Gee, like ‘golly gee’) for about fifteen years.  Recently, I noticed that when we were out, especially if we were in a group of mostly women, G would almost always be mistaken for a woman.  It seemed to me that he kind of enjoyed it.  So one night, I decided to have some fun with him and make him my ‘girlfriend.’  We were in a bar, and I went to the restroom, took off my panties, brought them back and gave them to him to put on.  It was such a turn-on.

H:  And he did it?

C:  Yeah, I’ve always been kind of bossy.  He didn’t want to, but he did.

H: G, your thoughts?

Gina:  I was really afraid to do it.  Christie is really good at getting me to do things that I just don’t see coming.  It keeps me on my toes.  She had me go to the restroom, take off my underwear and wear her panties for the rest of the night.  I was so afraid someone would notice, but really, how could they?  We had a really long discussion about why I felt that way.

H:  Did you secretly “want” things to turn out this way?

G:  Gosh.  That first night felt like more of a dare.  Once we got home, though, Christie and I sat up and talked a lot – about people thinking I’m ‘one of the ladies’ if we’re in a group, about why I was so nervous about wearing my best friend’s panties, why I thought someone might notice.  It’s really exciting, Christie has me do things that I never thought I could or would, shows me that I can, and then we talk about how it made me feel.  Most of all, I like making her happy.

C: You’re so sweet.

H: Christie, you decided to keep going further.  Why was that?

C:  G really is a good girlfriend.  We hang out together, shop, and talk about everything.  I thought it was so cute how nervous he got wearing my panties that I just couldn’t stop myself!

H:  OK, but it seems a stretch to go from wearing your best friend’s panties on a dare to wearing makeup and women’s clothes and going out in public.

C: It seemed like a perfect fit to me.  I really enjoy making him look the part.  He’s not a big guy, he has long, pretty hair and his features are kind of feminine.  So with a little work, he’s my girl!  I enjoy being in control, too.  A lot.  (laughs)

H:  Gina, you don’t do this all the time, do you?

G:  I don’t dress in women’s clothes and wear makeup all the time.  But I did…I do…get mistaken for a woman a lot.  The other day I was checking in at a conference for work, and I was standing next to a woman co-worker.  The woman at check-in said “Good Morning, ladies.”  My co-worker thought it was funny.   I was wearing a men’s sport coat!

C:  We do make sure he wears panties and a bra all the time, though.  We have matching lingerie!  And we make sure Gina shaves his body and keeps well-groomed.

H:  I can see that you keep your eyebrows shaped, and your hair dyed and styled.  You do have nice legs, too.  Does anyone ever say anything?

G:  Other than just thinking I’m a woman sometimes, no.  I get a little nervous when I wear shorts, though.

H:  Gina, you shave, um, everything?

C: (laughs) Of course!  That was one of the first thing we did.  I had G shave his legs, chest, underarms, crotch – everything.  I shaved mine, too, as part of the deal.

G:  Yes, that took some getting used to, but now I can’t imagine anything else.  Wearing a bra and panties every day is a challenge, especially at work.  I’ve almost been caught, maybe even I have, but it’s part of the thrill of doing what Christie tells me to.

H:  Whose idea was the blog?

C:  That was my idea.  It was another way to get Gina to verbalize what he was feeling when I challenge him to do certain things.  There are a few things we don’t publish, though, like sex.  At least between us.

H: So you do have a sexual relationship.

C:  Of course!  It’s a great motivator, too.  Gina knows there are rewards to doing what I say.

H:  Gina, have you had sex with guys?

G:  Yes, I have had sex with guys – well, one guy.  We wrote a blog about it.  I definitely didn’t plan on it.  I think I really did it to have one more thing in common with Christie.  It’s not like I’m interested in dating guys.

Helen:  Thank you both for being so open.  I was really curious after meeting “Gina” that first time.  Christie, you’ve done a really good job with Gina’s appearance and demeanor.  And Gina, you seem to be getting a little more confident every time I see you.  I think it’s good time to take a break.  Should we go out for drinks?

Waxing and Relaxing

Christie pointed out that I’ve been neglecting my waxing.  It’s no excuse, but I’ve been so busy lately that I really hadn’t had much time for myself.  Last Saturday, I decided to take care of it, and made my appointment at the local European Wax Center.  They are really wonderful, with a very classy, relaxing environment.

I always book my appointment online, but I’ve been there often enough for the receptionists and estheticians to recognize me.   I got up and showered, and put my hair up in a ponytail with a white scrunchie.  It was a little chilly, so I decided to wear jeans.  They used to be Christie’s, but they are practically new and look really cute on me (at least that’s what Christie tells me).  They have straight legs and are low-rise, and they are a little bit stretchy, so they fit nice and snug.  I picked out a floral print Hawaiian-style blouse.  I decided not to wear a bra, since I was going to have my back waxed, but I did wear light blue, floral pattern thong panties.  I didn’t wear makeup, since I was getting my brows waxed as well, so I just applied a little BB cream to even out my tone.  My nails still had some pink polish on them from Friday night, so I just left it on.

I got to the salon a few minutes early, and the receptionists greeted me, and told me that Caitlin would be ready for me in just a few minutes.  There were no other customers when I arrived, but within a few minutes, two other women arrived for their appointments.  Caitlin came out and got me, and took me back to her room.  “We’re doing your brows and back, right?”  I said yes, and she asked me if there were any other areas I was thinking about having done.  I told her not really, just the brows and back.

She had me lie on my back, so she could do my brows first.  “Just a little bit of a clean-up?” she asked.  I told her it had been a while since I last had them done, and asked her if she could shape them a little for me.  “No problem,” she replied.

While she worked, I tried to think of something to say.  I mentioned that my left brow seemed to grow a little “wilder.”

“I see that,” she said. “I can fix that right up.  Have you tried ‘ShapeIt?’  It’s a really good product for taming your brows.”  I told her I did use ShapeIt, and really liked how it worked to keep my brows neat.  “The right brow is a lot thinner.  Do you fill them in?”  I said that I did, and she told me about a brow powder and brush combo they sell.  “I can try it on one brow, and if you like it, I’ll show you how I do it.”

Caitlin expertly applied the powder to one brow, first filling in the tail, then drawing in below and squaring off the top, and finishing by brushing it out a little.  It looked perfect, and had a nice arch.  While I held the mirror, she filled in my other brow, explaining her technique as she went.  I couldn’t help but notice how obvious my pink nails looked in the mirror.

Caitlin finished my brows.  “OK, we’ll do your back next.  Just take your shirt off and lie down on your stomach.”  I did as she said.  “Should we do ‘breathe in – breathe out,’ or are you ok?”  I told her I was just fine.  I really didn’t mind getting waxed.  When she applied the wax to my lower back, I could her feel her hands brush the top of my thong.  As she worked, she asked if I wanted her to do my shoulders.  She explained that it was an additional service, so there would be a charge.  I told her it was ok.  “I’ll get most of them done with you lying down, then I’ll have you sit up and face the wall.  That will tighten you skin and make it a little easier.”

“OK, go ahead and sit up for me,” Caitlin instructed.  I swung my legs out over the side of the table and sat up.  I could tell my jeans were revealing the top of my panties.  As she worked, she asked if I shaved my arms or waxed them.  “I shave them,” I replied.  Caitlin said she’d be happy to do them next time, if I wanted.

“Ok, all done,” she said cheerfully.  As she walked me out, she asked if I wanted the brush and powder combo she used to fill in my brows.  I told her I did, and she started to look for a set in the proper color.  She asked the receptionist if they had the color she was looking for.  After locating it, she walked me over to the counter to pay.  “There you go.  See you soon!” she said, and went back to tidy up her room for her next appointment.

I didn’t really want this to be the end of my day, and before I had time to think about what I wanted to do, Christie texted me.  She wanted to come over to my apartment and drop off some things.

I got home and within a few minutes Christie arrived.  She complimented me on my newly groomed brows, and showed be a bag of clothes.

“I was cleaning out my closet, and found a few things that I still like, but they either didn’t quite fit right or don’t quite fit anymore, so I thought you might like them.”  She spilled the contents of the bag on my bed.  There was a pair of jeans, a pair of black pants, a couple of linen shirts with ¾ sleeves, and a pair of black shorts.  She handed me the shorts.  “Here, try these on.”

The shorts were made of a really light material, and had a side zip and a tie at the waist.  I took off my jeans and pulled on the shorts.  The felt really sexy because of the light weight and the way the material draped.  “I like these,” I told Christie.  “Thank you very much.”

“They are cute on you.  They’re just a little too snug in the hips for me.  Try the other things on, sweetie.”

We worked our way through the clothes, and I started to put them away.  Christie stopped me.  “Let’s go do something.  I don’t want to go home.”  We agreed that we could both use a nice relaxing afternoon drink, so Christie helped me get dressed.  I did my makeup, and Christie selected a white bra and white sleeveless top for me.  “Did you shave your legs today?”  she asked.

“I did shave my legs today, before I went to the wax center,” I replied.

My new shorts.
My new shorts.

“Good girl,” she said.  She handed me a pair of nude pantyhose to put on, and then the black shorts she had just given me.  “These will look so cute.”  While I finished dressing, Christie picked out a pair of low black pumps for me, and a silver anklet.  It seemed a bit much for early afternoon, and I felt a little self-conscious.  She pulled my hair out of the ponytail I had it in, fluffed it up a bit with some mousse and hair spray, and decided we were ready.

The bar we went to wasn’t crowded, but it was cool and comfortable dark inside, despite the growing heat outside.  The waitress came over and took our orders.  She returned a few minutes later and set them down.

“Here you go, ladies,” she said.  She placed her hand lightly on my shoulder.  “My name is Sierra, if you need anything else, sweetie.”

Working girl?

Christie texted me about joining her for happy hour last week.  I’ve been pretty busy lately, and having a few drinks sounded just the thing.

I knew Christie would be coming from work, so I decided to wear something along the same lines.  Following her rules, I was already wearing red panties and bra that matched hers.  We were going to our “usual” spot – an Italian restaurant with a nice bar area.  I’d been there a number of times with Christie, and I was comfortable going there dressed up.  A few months ago, I never would have believed that I could ever be ok with going out dressed in women’s clothes and wearing makeup.  I settled on a pair of black slacks, heels and a red sleeveless top.  It’s been unusually warm here in Southern California, and I wanted to look kind of dressy but still be comfortable.   I did my makeup and hair the way Christie likes me to, and chose a pair of silver hoop earrings, a silver necklace, and a silver ankle chain.  I added some dark red nail polish, and was ready.

I arrived at the bar, which was still pretty empty.  I took a seat at a tall table at one end of the room and waited for Christie.  A server came by and took my order, and right after she dropped it off, Christie walked in.  I waved to her and she came over to join me.

“Hi, sweetie,” she said, kissing me on the cheek.  That’s when I noticed she wasn’t alone.  She introduced the woman with her as her friend Helen.  “I just ran into her parking the car.  Helen, this is my friend G.”  (Almost everyone I know calls me “G.”)  I reached out to shake her hand.

“I thought you said you were meeting a guy friend?” Helen asked Christie.

“I did,” said Christie, a huge smile on her face.  “We decided that G would make a better girlfriend than guy friend, didn’t we, sweetie?”

I barely managed a reply.  “I, uh…”

“Oh, my god!” said Helen. She looked surprised, but shook my hand and sat down.  The server came back and took their orders.   Christie explained how I frequently got mistaken for a woman.  “It always seemed like he liked it, so one day a few months ago I decided I would dress him up and have some fun.”  Helen giggled.  “She looks pretty good, doesn’t she?”

“Actually, yeah,” said Helen, who still looked a little shocked, but was smiling, too.

Christie and Helen were exchanging details of how work has been going for each of them, when Christie’s phone rang.  It was her work, so she excused herself and went out to take the call.  Helen smiled at me.  “So, what’s the deal?”

I nervously explained how it started with Christie giving me her panties to wear, and how that grew to buying clothes together and teaching me to do my hair and makeup, and eventually, to going out for drinks or movies or to a show.

“Do you dress like this all the time?” she asked.  I said no, but that one of Christie’s “rules” is that we always wear matching panties and bras.  I admitted that the bras were a challenge sometimes.  She asked me some more questions, and I went on to tell her how I keep my legs shaved, and the rest of my body hair-free.  She noticed my underarms were shaved, and that I’d had my ears pierced and eyebrows waxed and thinned to look fairly feminine.  She seemed amazed that nobody at work gave me a hard time.  I admitted that I was nervous about getting caught sometimes, but so far nobody seems to have really noticed.

“Nobody has ever said anything, anyway,” I added.

After about thirty minutes, Christie came back.  “Client issues,” she said, adding “at least I didn’t have to go back in.  All good, now, though.”

The conversation turned to Helen’s job.  She is a CPA, and she went on to explain that, being tax season, she was very busy.  “I really need an extra person in the office.  I can’t get anything done, for all the phone calls and client meetings, so I end up working late a lot,” she lamented.  “I’ll probably work tomorrow, even though it’s Saturday, just to catch up.”

We three chatted on for a couple of hours, enjoying a few more rounds of drinks.  I didn’t say much, mainly just chiming in when Christie talked about a movie or show we’d seen together.

At about 9, Helen said she had to leave.  “Working tomorrow, remember?”  Christie looked at me and then said to Helen “I have an idea.  Why don’t you take G to work with you?”  Helen thought about it for a moment.

“Would you?”  She asked me.  “It really would be a huge help.” She explained that she was falling behind on doing her clients’ taxes because of the interruptions of making copies, filing, and answering phone calls. “That’s really all you have to do, but it would let me get some real work done.  Please?”

Christie added that she thought it was a great idea, and that she would pick me up and drop me off at Helen’s office.   I didn’t have any other plans, so I reluctantly agreed.

The next morning, Christie came by to pick me up.  She was carrying a smart-looking short black dress and a black sweater with ¾ sleeves.  It was hers, but we wear almost the same size, and she explained that she wanted me to look professional while I was at work with Helen.  She told me she had already discussed it with her, and she was looking forward to putting me to work as her office assistant.

I dressed, and Christie helped with my hair and makeup.  She handed me a pair of sheer pantyhose, and pulled my black pumps out of my closet.  We put my wallet, phone and some lipstick and a compact into a black purse.  Off we went to Helen’s office.

The office was on a corner in a kind of large, one-story office park.  Helen was already there.  She complimented me on my appearance, and showed me the receptionist’s desk.  It was in the front of the office, which had floor-to-ceiling glass windows on two walls.  Behind the desk and through a door were Helen’s office, a conference room, and a room with filing cabinets, a copy machine, and a large work table.  She set me to work making copies of tax returns she had completed – one copy for the client, and the other for her files.  I put each copy into a folder, and set them aside for the clients to sign at their appointments.   She also explained how to answer the phone.  “Just use your regular voice,” she said, “since nobody will see you.  I’m not expecting any drop-in’s today, so don’t worry.”  She smiled, and added, “I really appreciate this.”

After about an hour of copying, Helen came out of her office with two cups of coffee.  “Time for a break, hon.”   We sat at the conference table and chatted over the coffee.  When we finished, she patted my knee and stood.   “Back to work.”

Later that morning, the phone rang.  I answered it as instructed, put the call on hold, and walked to Helen’s door.  “Excuse me, Helen.  The Clark’s are on the phone, and wanted to know if they could come in today to pick up their tax paperwork.”

“See what I mean?” Helen said.  “I’ll never finish get through all this work.  Sure, what time do they want to come in?”  I told her they asked to come in at one.  Helen nodded, and I went back to the phone.

Helen came out of her office and told me how to set up the conference room for the new one o’clock appointment.  “When they come in, just show them in and I’ll come out and meet them.”  I went back to copying and filing.

The Clark’s arrived on time, and I showed them to the conference room.  Helen joined them and shut the door, leaving me at the front desk to continue copying and filing.  At one point, the intercom rang.  Helen asked “Gina, could you come in for a moment?”   I stood, smoothed my dress, and went to the conference room.  The Clark’s looked up when I came in.  “Gina, could you make two copies of this page for me?”  I smiled and nodded, and took the paper from her, returning a few minutes later.

The Clark’s finished their appointment and left.  Helen came out of the conference room, handed me a file, and said “This can be filed away.  That was kind of fun, like we had a little secret.”  She smiled.

We worked until about four, when Helen came from her office and said “That’s about enough for me.  Thank you again for the help, Gina.  I am so much farther ahead, with your help.  Would you like to grab a drink somewhere on the way home?”

I told her I would love to, and we collected our purses and went out to her car.  This would be exciting-the first time I’d gone out dressed without Christie.

Later that Night…My Adventure as a Cocktail Waitress (Continued)

When we finished this last amazing kiss, I found myself both excited and petrified.

“Ed, we should stop this.  I’m not, you know, gay or trans or anything.  I just did this because Christie asked me to and we thought it would be fun,” I explained.

“You’re probably right,” Ed agreed.  “This is just really interesting for me.  I’ve known you for a long time, and I’ve never done anything like this.  I guess I was just kind of turned on by how good you look, and kind of, um, curious.  I’ve never been with a guy dressed like a girl.  You’re a really cute girl, by the way.”  He chuckled.

“Well, thanks,” I said. “I should get changed.  I’m really tired.”  I stood up, and so did Ed.  Ed took my hand, hesitated for a minute, and added “I do have a favor to ask you, though.  It’s going to seem weird.”

“Hey, how much stranger could this night get, right?” I smiled at him.

“Could I help you get undressed?”

“”You want to undress me?” I asked.

“I just think that you look really good, and I’m curious about how you did it,” was Ed’s reply.

Maybe I was just too tired to argue, or maybe I was just a little bit excited about the idea, but I agreed.  We walked down the hall to my room, where Ed sat on the edge of the bed.

“I can’t believe I’m really doing this,” I said, shaking my head.  I stepped out of my heels, and reached around to my back to unzip my skirt.  I fumbled a little bit, looking for the zipper tab – just nervous.

“Here, I’ll get that,” said Ed, as he turned my by the hips and slowly pulled down my zipper.  He turned me around to face him, and I stepped out of thee skirt and hung it over a chair.  My hands were shaking as I started to undo the buttons of my blouse.  Ed quickly reached up and took over.  He pushed the blouse off of my shoulders, and tossed it onto the chair. “Wow, you shaved your chest, and your underarms, too.”   I pulled the breast enhancers out of the bra, and showed him, and explained what they did.  I reached back and undid the bra, letting it fall.  Ed commented on the lines it left on my chest, almost making it look like I actually had breasts.

I dreaded the next part.  It must have shown on my face, because Ed said “it’s okay” and started to push the pantyhose down my hips and legs.  He helped me take them off, commenting on my legs.  “And you painted your toes!”  I didn’t want to admit that they were always painted, so I explained them by saying it helped me get in the mood.  All I had left was a pair of white bikini-style panties.   I thought we were done, but Ed persisted.  “I’m really curious as to what you did with your, uh, you know.”

I pulled down the panties, and explained how I had “tucked” anything that might cause a bulge.

“Wow, you shaved there, too. “

I sat down on the bed next to Ed, placing one arm across my crotch to keep it somewhat hidden.  Ed thanked me and told me how convincing I looked.  I didn’t say anything, and in the silence, Ed leaned over and kissed me again, stroking my thigh with his hand.  I fidgeted a little, and he took my hand and placed it over his lap.  I could tell right away he was aroused, and also that he was big.  Very big.

“Is this okay, G?”  he asked quietly.  I think I said “I guess,” and rubbed his crotch a bit.  “Go ahead,” he said, “it’ll be okay.”

I undid his belt and fly, and reached into his pants, pulling out an enormous cock.  “Wow, you’re, like, porn-star big.”  Suddenly, I realized I didn’t think it strange that I held his dick in my hand.  I gave it a stroke, and leaned down and put it in my mouth, remembering all the lessons that Christie had given me with our dong.  The only difference was his size, and the hair.  I could tell he was enjoying himself.  In truth, I was, too.

“God, that feels good.  Are you sure you’ve never done this?”  he said.

I didn’t want to tell him about the lessons, so I just said no.  After a few minutes I could tell that his breathing was getting more urgent.   I hadn’t really thought about this – it isn’t a problem with a rubber dong.  I was trying to figure out how I would handle the inevitable, when suddenly it was too late.  Ed exploded into my mouth.   I gagged a little bit, but managed to not make too much of a mess.

Ed lay back on the pillow and put his arm around me.  We talked for quite a while, when I noticed he was getting aroused again.  I stroked him as he caressed my rear.  He asked me if I had a condom and some lube.  I reached into my nightstand and got both.  “Back door, huh?” he said, reading the brand name of the lube.

I had never put a condom on another person, so I fumbled around a little.  By the time I got it on him, he was thoroughly hard.  He positioned me on my side, telling me it would be easier the first time this way.  I didn’t mention all the times Christie had done this with her strap-on.  I was worried about how big he was, and I should have been.  It hurt!  Once he got in me, it was better, but it still hurt a lot.

Ed came, and rolled onto his back, removing the condom and handing it to me.  I went to the bathroom to dispose of it, took off what remained of my makeup, and returned.   He was sound asleep, of course.  I laid down on the bed and was out like a light.

I woke up early the next morning, and quietly grabbed a pair of panties and Ed’s shirt, and went out to the kitchen to make coffee.  About a half-hour later, Ed came from the bedroom.  “Is that coffee I smell?” he asked.  “Nice outfit.”

I handed him a cup of coffee and we sat down at the kitchen table.  We talked about the previous night until we finished the coffee.  Ed got up to leave and I walked him to the door.

“You know, if you ever want to go out or something, I’d be happy to go with you,” he said.

“You mean, go out like last night, dressed up like a woman?”

“Yeah, I do.  I mean, only if you want to.”

I walked him to the door, where he took a last opportunity to give me a kiss while his hands roamed over my bottom.  I gave him his shirt back, and he left.  About ten minutes later, as I was pondering the last night’s events, my doorbell rang.  I threw on a robe and checked the door.  It was Christie, and I let her in.

“Hey, Gina, I just stopped by to see how the rest of the night went.  Was that your friend Ed I saw leaving?”

“Yes, that was Ed,” I replied.

“Tell me,” she said, taking my hand and leading me to my couch.

Adventures as a Cocktail Waitress

It took a lot to convince me to do it, but I’m glad I did.  Last month, Christie wanted me to help her out at a charity event.  “Helping” involved dressing as a cocktail waitress and serving drinks.

The event was a Great Gatsby style casino night, at which guests were encouraged to wear 1920’s style attire.  Christie had offered to provide the bar tending services, so she enlisted some friends.  The plan was for Christie and one friend, a professional bartender, would work the bar – mixing drinks and pouring wine and beer.  Four others of us, three women and me, would be cocktailers.  Two women would work the event floor in general, while the other woman and I would focus on the gaming tables.  (The games were played with “fake” money, but the drinks and tips were real.)

A few days before the event, Christie took me shopping for our uniforms.  She would wear black pants, a white tuxedo shirt and a black vest.  The cocktail waitresses, including me, would wear black miniskirts and tuxedo shirts with black pantyhose and black heels.  I was really panicked about the whole idea, but Christie explained to me that in the past, guests had not only dressed in 1920’s attire – men in tuxedos and top hats and lots of “flappers;” apparently many started dressing as characters from an old-style circus – it had become much more of a costume party than a mere casino night.  Eventually, Christie convinced me that I would fit right in, even if some people did figure out that I wasn’t the girl I pretended to be.

Christie and I have gone shopping together many times, and it’s always fun.  We picked up some women’s tuxedo shirts and a black vest for her at a formalwear shop, then went to H&M for a black skirt for me.  The skirt has some stretch to it, so it fits nice and snug and looks great.  Next we picked up some matching black shoes with a not-too-high heel (I couldn’t imagine trying to carry a tray of drinks in my other heels) and some sheer black pantyhose for me.

On the afternoon of the event, Christie picked me up to help her set up the bar.  This gave me an opportunity to see the venue and get a little more used to the idea.  We both wore jeans and t-shirts to do the setting up, since it involved carrying a lot of boxes and ice bags, and moving tables.  Nobody seemed to notice that I was wearing women’s jeans.  I was very conscious of the bra that was slightly noticeable beneath my black t-shirt, and I tried to be extra careful when I had to bend down, to make sure my lace panties didn’t show above my jeans.

I also met Lex, the bartender Christie had gotten to help her.  Lex commented to me that she thought it was really sporty of me to help out the way I was.  Christie had obviously let her in on our secret.  I felt a lot more comfortable with the coming night.

Once Lex and Christie were happy with the bar, we went home to change.  It wasn’t far from Christie’s apartment to the place where the casino night was being held, so we changed there.  Christie helped me with my hair and makeup, and I realized I felt pretty confident in my appearance.  I chose a dark maroon shade for my nails, added a watch and some silver earrings, and I was ready.  We headed back to the event hall.

Shortly after we arrived, I met the two three women who would be cocktail waitressing with me.  They were dressed the same as I was, and as we chatted and got to know each other, they all giggled and said how cool they thought it was that I was doing this.  I relaxed.

The guests showed up quickly – one minute it was just the twenty or so of us working the event, and the next it was fairly crowded, with people lining up for drinks, finding open seats at the tables, or just mingling, while we took drink orders and other waiters and waitresses carried trays of appetizers.  I ended up with three poker tables, which kept me pretty busy.  I would walk around the tables, checking for empty or nearly empty glasses, ask if anyone wanted a refill, take orders, and then go back to the bar, where Christie or Lex would make up the drinks for me.  Then I’d take the drinks back to the tables, collect money (and tips!) and take more orders.  Everything was going quite well, until later in the evening, I realized that I knew one of the guys at one of my tables.  It was Ed, someone I had gone to college with and known really well.  The next opportunity I had, I went to tell Christie.

“I know one of the guys at the poker table!” I told her.

“You do? How?” asked Christie.  I told her.  “Lex, ‘Gina’ says she knows one of the guys at her table.”  Lex told me not to worry, told me that I looked great and was doing a perfect job.  I wasn’t convinced, but went back to work.

On my next trip back to Ed’s table, I realized he was staring at me.  He had taken a break and was standing next to the table.

“G, is that you?”

“Um, yeah,” I replied.  “Ed, I didn’t expect to see you here.”

“I bet.  Yeah, I moved back a few months ago.  I’m staying with my sister Kim until I find a place.”  He introduced me to the “flapper” standing beside him.  “Man, you really get into the spirit of this thing,” said Ed, looking me up and down.  “You do look pretty convincing.  I recognized your voice, though.”

“I think he looks cute,” added Kim.

We chatted for a few more minutes, and I excused myself to get back to work.  I couldn’t shake the nervousness I developed when I recognized Ed.  I mean, we had gone to school together for four years, and knew each other pretty well.

It was apparent the next time I made my rounds that Ed had told some others at the table that he knew me.  All of the guys at the table were grinning, and began ordering drinks saying things like “how ‘bout another round here, babe.”  They were all good-natured about it, so I started to relax.

Late in the evening, when things started to wrap up, Ed came over to the bar, where Christie, Lex and I were planning on how to break everything down at the end of the night.  There wasn’t much to pack up, but there was still a fair amount of cleaning up to do, mostly just picking up glassware and putting it where the rental company would pick it up the next day.  Christie asked if I would mind staying with Lex one of the other cocktail waitresses, while she and the others took the unopened bottles of liquor, wine and beer out to her car, so she could take it back to one of the charity’s officer’s homes.

“How will I get home?” I asked.

Ed, who had overheard part of the conversation, volunteered.

“I’ll get you home.  Kim and I drove separately, and it’ll give us a chance to catch up.”  I was pretty nervous about having Ed drive me home, but I agreed.

“Thanks, sweetie,” said Christie.  “I’ll catch up with you tomorrow.”

After the last guests cleared out, and the remainder of the bar had been put away, Lex, and the other waitress left.  Ed walked me out toward his car, holding the door for me as we left the building.  He surprised me by holding his arm out for me to take as he walked me to the car.  He held open the door for me and helped me into the seat and shut the door after me.

We did a little catching up on the ride to my apartment, filling each other in on what we’d been doing since school.  At my apartment, Ed opened my car door for me and walked me to my door, where I invited him in.

“I am exhausted,” I sighed.  “That was fun, but a lot of work.  At least I made some great tips.”

Ed volunteered to brew some coffee, and when he returned from my kitchen, he sat next to me on the couch.

“If anyone ever told me that I’d be sitting on your couch with you dressed like that, I’d have told them they were crazy.  You do look the part, though.  You have great legs.”

“Stop it,” I said, laughing.  Ed retrieved two cups of coffee and came back to the couch.  After he set them down, he stepped behind me, and massaged my shoulders a bit.  It felt great, and I realized that I had moved one of my hands and placed it on top of his on my shoulder.  “God, that feels good.”

Ed came around and sat next to me.  It seemed like slow motion, as he leaned in and kissed me.  He was a fantastic kisser.  My heart was pounding.  “Have you ever kissed a guy?” he asked.

“Never before now,” I replied.  “Have you?”

“I still haven’t,” he said quietly, and kissed me again.