All posts by Gee

About Gee

A while back, my friend Christie decided that I would make a much better girlfriend than boyfriend. It took some years, but I now work and live "mostly" as a woman, with the loving support of my closest friends. These are some of our adventures.

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.

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.



My Weekend

Something kind of unnerving happened at work last Friday.

I was doing some warehouse work, so I was wearing heavy boots, Dickies work pants and shirt, and a hard hat.  I was, of course, wearing a red bra and panties, as Christy had instructed that morning.  The shirt was a pretty heavy material, so I wasn’t too worried about anyone noticing the bra.  I had my hair in a ponytail, held with a black band.  In short, I looked about as much like a “guy” as I could.

At the same time, there was a class in the conference room of the warehouse.  It looked to be all younger men.  I didn’t have anything to do with it.  Until, that is, that the person coordinating the class asked me to set up a computer monitor, so the class could view a video.  I went to set up the equipment, and as I was working, one of the young men bumped me as he was shifting tables around.  I said,” Excuse me.  I’ll be out of the way in a second.”

The young man replied “No worries, miss,” and continued setting up the tables.  The instructor, one of our salesmen, chuckled a bit, but didn’t say anything.  The four or five other students in the room didn’t say anything.  Maybe they hadn’t noticed.  I finished setting up the monitor and went back to work.

I felt a bit uneasy that he thought I was “miss.”  I’ve been mistaken for a woman so many times (that’s how my relationship with Christy started, after all).   This time felt more intimidating, perhaps because I really was wearing panties and a bra, and it happened in front of a male work colleague.  It also made me kind of happy.  I spent most of the day thinking about the incident.

Christy was away Saturday, so I wasn’t expecting much of an exciting day.  I had a few things to do, but I really had no plans.  It turned out to be an interesting day.

I had an appointment with Claire, my waxer, in the morning.  The weather had been chilly early in the morning lately, but when I woke up, it was already nice and warm.  That changed my planned outfit for the morning.  I had planned to wear my black leggings with the sheer panels, and a zippered hoodie.  I wanted to wear something that didn’t pull off over my head, like a t-shirt, since I was having my back and shoulders waxed that day.

Christy had texted me that morning, as she does every day, to let me know what bra and panties to wear.  Today we would wear beige, which meant a beige thong and padded “t-shirt” bra.  I settled on a pair of very short denim shorts and green Hawaiian-patterned shirt.  I dressed and did my makeup, keeping things pretty simple, since waxing by brows meant wiping off whatever I applied anyway.  I chose my “nude” palette, brown eye liner, and a shimmery nude lipstick.  I finished by doing my nails in teal.

I arrived at the salon a few minutes early. I took my bra off in the car; I didn’t want to have to take it off and put it back on in the salon.  Claire would see I’d been wearing a bra from the marks it left on my shoulders and back.   As I walked in, one of the receptionists greeted me with a cheerful “Hi, Gee!”  I smiled and said god morning.  The receptionists told me that Claire would be ready in a few minutes.  As I waited, the two receptionists started discussing the various skin care products on the shelves of the salon, and which they liked best.  They included me in the conversation, and pretty soon we were all testing the sample products and talking about which smelled the best.  Claire came out to get me as the three of us were laughing and trying different lotions.  Claire smiled and took me back to her treatment room.

I like Claire.  She’s always chatty and friendly, and she takes her time with me.  She had me lie down on my back to wax my brows.  She carefully trimmed and waxed them, then offered to finish them with a brow pencil.  She then had me take off my shirt and lie down on my stomach so she could wax my back.  It’s always a little exciting when she waxes near the top of my shorts.  I was pretty sure that my thong was peeking out as well.  She finished my back and had me sit up, so she could finish up my shoulders.  She offered to touch up some parts of my neck and upper arms, too.

Claire walked me back to the receptionists, where I made my next reservation.  I headed out to my car.  Instead of running any more errands, I decided to go home, touch up my makeup, and change into something else.

I was feeling pretty good, and excited about going back out.  I touched up my makeup, and put on a yellow floral romper.  It’s loose and flowy, and feels very sexy.  I decided to go to a local BevMo and get some champagne, for when Christy got back.

I drove to the store and parked, checked my lipstick and went in.  The store was crowded, but the lines were moving quickly.  I grabbed a cart, and went to make my selections.  When I returned to the checkout line, it was much shorter.  There were three male cashiers, and one woman.  The line moved up, and when it was my turn, the woman said “I can help you here.”

I put four bottles of champagne on the counter.  All four were “Domaine Carneros 2013,” from Napa Valley.  The checker picked up a bottle.

“Oh my god.  Have you had this?  It is absolutely my favorite,” she said.  She asked if I had ever been there, and told me that it looked just like the picture on the label.  She seemed so pleased that I had chosen it.  She rang up the purchase, and I gave her a discount coupon that I had.  As the sale was processing, she added “you look very pretty today.”  I thanked her.  As she handed me the receipt, she said “if you ever go to Napa, come see me.  I can tell you all the best places to go.”  I thanked he again and went back to my car.

I hadn’t planned on going out, but later that night, I changed my mind.  I thought I might go to Roy’s, the Asian fusion restaurant that I’d been to a few times.  I thought it might be fun to sit at the bar and enjoy a drink, and maybe see Tina, the bartender I had talked to the last time I was there.

I did my hair, reapplied my makeup, and changed my nail color to a dark red.  I was still wearing the beige thong and bra, and added a pair of nude stockings.  I chose Christy’s short, red dress (which seems to be in my closet more than in hers).  Some black heels finished my outfit.

I drove to the mall and parked.  The parking garage was full, but not a lot of people.  I walked to the restaurant and walked in.  It was absolutely packed.  Seeing no seats at the bar, and not seeing Tina, I left.  I went around the corner to a steakhouse, and found a seat at the end of the bar.  I asked the woman next to me if the seat was free, and she told me it was.  There was apparently a large convention in town, and that’s who was filling up all of the places around.  I ordered a glass of wine.

“I think you’ll like that,” said the woman next to me.  “It’s what I’m having, too.”  My wine arrived, and I took a sip.  I smiled at the woman next to me, and told her I, too, thought the wine was quite good.  She introduced herself, and I did the same.  Maggie was her name.  She asked me if I was with the convention.  I told her no, that I lived here in Anaheim.  “Me too!”  she exclaimed.  “This is pretty much my local hangout.”  She complimented me on my dress.

We talked for quite a while, until one of the convention-goers, an older man, struck up a conversation with Maggie.  I had another glass of wine and just watched the people in the restaurant.  Maggie would occasionally turn to me and we would talk some more.

Last call finally came.  I had no idea it had gotten that late.  I paid my bill, Maggie paid hers, and we both got up at the same time.  We walked to the garage, arriving at my car first.  “This is me,” I told her.  She gave me a hug.  “It was nice meeting you.  I hope we run into each other again, soon.”  She left toward her car.

I drove home really happy that I’d decided to go out, and that I wasn’t deterred by the crowd at my first choice.

Some Monday Night Fun

Christy reminded me again that it was time for some waxing.  I did need to get my eyebrows waxed, and with the heat this summer, we decided to get my back and shoulders done, too.  I’d recently changed locations where I get my waxing done and liked the woman who did it last time, Claire.  I had some time off coming, and decided that I would take Monday afternoon away from work to get it done

After getting home from work about 1, I showered, shaved carefully, and decided on an outfit to wear.  Christy had decided we would wear red lingerie, so that much was decided.  I put on a red thong and red lace bra.  I wanted to wear something that buttoned up, so I wouldn’t have to struggle when it came time to take my top off.  I chose a short-sleeved plaid flannel top.  I pulled on a pair of white shorts, and a pair of white tennis shoes.  I did my makeup and put my hair into a loose ponytail.

When I arrived at the salon, I took my bra off while I was still in my car.  I didn’t want to have to put it on in front of my waxer when we were done.  The marks on my back, shoulders and chest would be enough evidence that I’d been wearing one.

I didn’t have to wait long before Claire came out to get me.  We walked back to her treatment room, and chatted as she worked.  After she finished, she walked me out to the reception desk, where I made my next appointment.  I went back to my car, drove to a shady corner of the parking lot, put my bra back on, and put the silicone breast enhancers back in place.  I touched up my makeup as well.

After leaving the salon, I decided to do some errands that Christy had asked me to do.  The first was to pick up some wine for the weekend, so I drove to the local wine shop.  It wasn’t at all busy, so I was fairly relaxed as I did my shopping.  At the checkout, the woman working rang up my purchases, and complimented one of the choices I had made.  She asked me if I had ever tried it.  I replied that I hadn’t, and she assured me that I would love it, once I had.  She was actually quite chatty, as she boxed up the bottles and I paid.

I got back to my apartment and took the wine inside.  I felt pretty confident, and really wanted to go back out.  I would have texted Christy, but she was out of town for work until Friday.  I decided that I would change and go out for a drink at a happy hour somewhere.  I thought about where I would go as I picked out an outfit for the evening.  I settled on Roy’s, a Hawaiian-fusion restaurant near Disneyland.  They have a nice bar, which isn’t too busy, once happy hour is over.  I thought I’d get there around 6:30.  I was a little apprehensive, since I rarely go out all alone.  

I showered, did my hair and put on my makeup.  I chose a black lace thong and a black padded bra.  I decided to be daring, and put on a black garter belt with some sheer thigh-high stockings.  The skirt I chose, a black Hawaiian print, was just long enough to get away with that.  I picked out a lightweight, sleeveless knit top.  I found some black rectangular earrings as well.

I felt pretty good as I drove to the restaurant and parked.  I found a spot close to the restaurant, but it was still a short walk, past the valet parking and up a short, but busy, walkway.  I got to the restaurant and headed to the bar.  There were several occupied tables in the bar area, but nobody actually at the bar.  I recognized the bartender, Tina.  She was an attractive young woman, with springy red hair.  She’d been working there quite a while, and I’d seen her a number of times.  Christy and I had been there before, but I’d also been there in “guy mode” with business associates.

I sat down, and Tina greeted me.  I don’t think she recognized me.  She cheerfully offered me a menu, but I knew what I wanted (they have an amazing “Hawaiian Martini” with a wedge of pineapple).

The bar and restaurant were busy enough that we didn’t get to talk much, beyond just ordering drinks, saying thank you, and opening a tab.  I sipped my drink and people-watched.  I stayed for about an hour and a half before closing my tab, finishing my last drink and thanking Tina.  I walked up to the hostess to get my parking stub validated, then walked back to the parking garage.  They area was still quite busy with people, but I felt pretty confident and took my time getting to my car.

I got home, changed, and texted Christy to tell her about my short evening out.  We made plans to do something this weekend, when she got back.







A New Look

I suppose it was inevitable.  I needed glasses.

I had been getting by with those cheap “cheater” glasses that you find in drugstores, but they just weren’t cutting it anymore.  I asked a friend of mine, an optometrist, to do a quick checkup, and next thing you know, I’m on my way to wearing bi-focals.  Ugh.

I mentioned the news to Christie, and within minutes, she was on her tablet, looking up different frame styles.  She found a website that helped figure out what face shape I had (“square/round,” it turns out), and what style of frame would look best with that shape.  The website recommended either round frames or a style that followed the contour of the eyebrows, to soften the “squareness” of the face.  She even found a website on which we could upload a selfie, and “try on” various styles.

The next Saturday, we went to an “America’s Best” outlet nearby.  Christie and I were both wearing jeans and t-shirts.  I had a little makeup on, but not too much.

They had a deal for two pairs of frames and lenses for a really good price.  We walked in, presented my new prescription, and looked at frames while the optometrist on duty reviewed my prescription.

I needed a pair of glasses for work, so we got a pair from the men’s section that had stylish round frames that traced the contour of my brows.  I liked them.  I decided to get separate reading glasses instead of bi-focals.  We looked at some choices on the men’s displays, and then Christie steered me to the women’s glasses.

I was a little worried that someone would notice me trying on women’s frames, but everyone was too busy with whatever they were doing to pay us any attention.  Since the men’s and women’s readers were quite similar, I found a pair that we liked pretty quickly.

Christie really wanted me to get a pair of women’s frames, too, so we looked over the selections.  We had done the virtual try-on with a couple of styles.  I settled on a pair that were close in shape to the men’s pair, but a little more cat-eye shape.  They were tortoise, with blue accents, and the inside of the temples and frames were blue as well.

We took the frames to one of the fitting specialists.  As we walked up, she greeted us with “Did you find everything you were looking for, ladies?”  I told her we did, and sat down for her to take some measurements.  I filled out the order form.  I handed her my credit card to pay, and she looked at the name, looked up at me and smiled, and went back to running my credit card.  She said the frames would be ready in a week.

I’m excited to see how they look.

My Boudoir Photos

I had some difficulty writing this post, because so much happened on the day of the photo shoot.  I had an early appointment with a hair stylist, then a session with the makeup artist.  Both of them were amazing.  After an hour and a half of work, I can say that I was really pleased with the result.  I headed off to the photo studio.

There is so much to write about, but I’ll keep it short and get to the pictures.  The photo session lasted several hours.  The photographer was amazing.  She made me feel so totally at ease.  I changed into my first outfit, sipped on a glass of champagne that she gave me, and did as she said while she posed me.  When it was time to change, she had me switch outfits while she got the next set ready.  By the end of the session, I was exhausted, but felt amazing and confident.

A few weeks later, the photographer and I reviewed the photos, and chose which ones to further edit (she kept the retouching to minimum).  After another few weeks, re looked over the final result, most of which I’ve posted here.  I hope you like them.

One of the first photos – just starting to get comfortable.
Second Set
I think I like the black and white.  The mirror was fun, too.
The Corset Photo
The Giant Chair
The Wind Machine

I am so grateful to Christy for giving me this opportunity.

“I Know You…”

Last weekend, Christy and I went out for drinks after work.  Christy was going to come straight from her office, and told me to meet her at the bar.  It was a local restaurant, but had a large bar area that was typically not too crowded.  Christy was at the end of the bar when I arrived.  She handed me a glass of white wine, saying “Nice outfit.”

Knowing she’d be coming from work, I thought I’d wear something nice.  I had on a sort of sheer white blouse, a beige t-shirt bra, dressy black shorts and black pumps.  It was chilly, so I added a pair of sheer pantyhose.

I sat down, and Christy and I began to catch up.  Suddenly, a woman approached from my left.

“I know you, don’t I?” she stated.  I was pretty sure I’d never met her before.  She was attractive, with shoulder length black hair and beautiful dark eyes.  She was wearing a short black dress.  She went on, saying “I always remember faces.  You’re Michael…Michelle, I mean.  We met at a party in Marina Del Rey, god, ten years ago?” she said, naming a couple I’m sure I didn’t know.  I glanced at Christy, who showed the tiniest smile and stayed quiet, leaving me on my own.

“I…I don’t think so,” I said.

“But that’s your name, right?”  (It is, kind of.  My name is Michael, but ever since I was about 12, everyone has always called me “Gee,” the initial of my last name.)  “I’m JJ.”

The woman rubbed her hand up and down my upper arm.  “I’m sure of it.  Give it a few minutes and you’ll remember.”  She went on to describe the couple, calling them Laura and Conrad, sure I’d remember them or the party.  “You look great, by the way.  I like the way you’ve grown out your hair.  You had a wig last time, didn’t you?  And your makeup looks great.  Anyway, think about it.  I’m sure you’ll remember. I’ll be back later.” She walked away toward the restaurant.

“You really don’t know her?” asked Christy.  I replied that I was sure I didn’t.  “Well, that’s interesting.  She’s certainly convinced she knows you, or at least someone trans who looks like you.”  I thought about this for a minute.  Christy was right, of course.  A person I’d never met before (at least not at a party in Marina Del Rey – I’ve never been there) was convinced that she recognized me as a transwoman, crossdresser, drag queen or whoever was really at that party.  It was a strange coincidence about the name, though I’ve only rarely gone by “Michelle.”  And ten years ago I wouldn’t have dreamed I’d be doing any of this.  It kind of blew my mind.

Quite suddenly, “JJ” appeared at my side.  She put her arm across my shoulder and held out her phone.  “I found some pictures of Laura and Conrad.”  She showed me a half dozen or so photos.  “None are from that party, but I thought these might help you remember.”  I looked on as she scrolled through the pictures.  Christy, once again, stayed silent and just watched, smiling slightly.

The bartender stopped by, to see if we needed refills on our drinks.  JJ ordered another round for the two of us, telling the bartender “Check this out, Heather, we met ten years ago!”

We drank our drinks, JJ doing most of the talking, while I maintained that I didn’t quite remember her or the party.  In the end, she insisted that we exchange phone numbers.  After we did, she hugged me and excused herself to get back to the group she was with.

Christy just smiled at me.

I’ll admit that I was kind of excited to talk to her, and I hoped I’d see her again.

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.