Office Dress up
By Gail Blue
"Hi Honey, what have you been up to all day?" I was laying on the sofa reading a magazine. The rain had been misting through the morning and Lucy was unbundling herself in the foyer. Her sandy blond hair damped down just enough so that it twirled when she unwound the scarf from around her neck.
"Just went down to salon and got my legs waxed."
"Ouch did it hurt?"
"No, it only hurts the first couple times. Maybe they're a little sensitive, but I can't tell you how good it feels." She stepped in front of me and rubbed her legs to illustrate. Her eyes stared smiling into mine as I looked up. "Do you wanna see?"
"Sure." I laid down the magazine. Lucy unbuttoned her jeans at the waist and kicked them off with her hips. She avoided using her hands instead working the material down by rolling her knees together. Finally she stepped out of the jeans and straddled me on the couch.
"See nice and smooth." She took my hand and ran the back of it against each thigh.
"That is nice. Wish we had more time."
"We will tonight. We have a little time now." She touched her nose to mine. "I love the feeling of smooth legs."
"Me too."
"Hehe you ought to try it sometime."
"What wax my legs?"
"Shave them maybe. It feels nice, two sets of smooth soft legs. I haven't felt that for a while."
"You thinking about girls again?" I knew Lucy was bisexual when I met her. It was one the issues she brought up when we talked about whether or not to get married. Neither of us felt the need for marriage but the social advantages made life easier. I offered that if she ever 'needed' to be with another woman that it would be alright with me as long as there was no relationship, it made her feel easier about the whole thing and we got hitched.
"Maybe, maybe not. I'd rather feel that with you. I mean if you're okay with it."
"Probably wouldn't kill me. We can talk about it when we get back from dinner."
Dinner was pleasant, we met a few of her friends in West Hollywood for Indian food. They were a gay couple she'd gone to design school with. They asked how business was. Business was fine, Lucy and I had opened a small advertising firm last year. By small I mean there were only three of us in the firm: Will Lynes, Lucy Lynes, and Kaye Henton. Kaye had gone to school with us for a year before she dropped out from boredom, and Will was me. Lucy and Kaye had majored in design. I minored in it, majoring in business then got my MBA.
Kaye dropped out the year Lucy had graduated and they both ended up at a larger firm for a year before becoming sick of the office politics. When I finished my master's they pleaded with me to start something independent which sounded like a great idea so long as the money worked out, which it had thanks to a bit of luck and some connections they made at the other firm. We worked for smaller local companies, in LA most of those would go out of business, blown away like seeds that never take root but a few stuck and got big. We weren't getting rich but we were getting by alright.
Dinner finished up and when we got home Lucy asked, "So have you thought about it?"
"What?"
"Hehe letting me shave you?" Lucy was giving me her puppy dog eyes.
"Oh that. We can try it."
She hopped twice in celebration and lead me to the shower. It took a while longer than I would have thought, but she insisted on getting everywhere, my belly, my arms and pits as well as my legs and anywhere she found even a stray hair.
After that we made love. Lucy was amazing, she explored my body with her hands, with her legs, and with her tongue. I'd never seen her so worked up, she kept going long after I was spent. We just laid there until I woke up the next morning to find her rubbing her legs against mine.
"You seem to be enjoying yourself," I said.
"Oh yes, I love how smooth you are. How soft too."
I laughed. "So you didn't marry me for my rugged outdoorsy good looks?"
"Good looks? Yes... you're a pretty boy. Pretty boys are better. If I wanted dumb and hairy I'd just get a dog. Does it bother you if I call you pretty?"
"Naw, it's sweet. Just makes me wonder if you're thinking about girls."
"Girls are good. If you were a girl I'd still love you as much, but you're a man and I love that too."
"Well I'm glad you liked the shave, just don't ask me to wear a dress or anything."
"No but there's just one other thing." Lucy ran her fingers through my hair, picking at the ends and curling a lock around my ear.
"Yes?"
"Don't get your hair cut too short. I love running my fingers through it. I love the smell of it after you wash it." She nuzzled her nose against the back of my head.
"If you want me to I could grow it out a bit...?"
"Oh yes please," Lucy clapped. "And if there's anything I can do for you just say so. I think it's sexy that you let me play with your body change it around to my liking." She kissed my belly button giving me her seal of approval. "If there's anything you'd like me do to myself just let me know, it would really turn me on."
"Well a red head might be fun." I patted the top of her head, and she smiled.
Things took shape over the next six months. At first it was a pain shaving my whole body, I'd get razor rash and ingrown hairs. I was about to give up on the whole idea when Lucy mentioned laser hair removal, for both of us. I'd said it was a bit odd for a man to be permanently without body hair. Then she started pointing out smooth bodied men, no men in television ads have body hair and only about half the men at the beach did. I was just about convinced when Lucy offered to let me "change something else" about her in return. Her teeth had always been okay, but not so good. Honestly it didn't bother me at all, but Lucy seemed turned on at the idea of me changing her, she keep asking if she needed a larger ass, or a tattoo, or an accent. I hadn't given it as much thought as she had, and when I mentioned her teeth I thought she might be embarrassed, but instead she just smiled at me, exposing them, flicking her tongue against them. She talked about it all night, made it sound important. So Lucy got braces and I got smooth body.
The hair was another matter. Lucy had gone red as I'd asked and before she ever went to the hairdresser, she'd ask me, "What color?" I'd been growing mine out as she had asked that night. Lucy said it need to be cut and she brought me to her stylist. She told her, "Leave it long but make it pretty."
I blushed when the stylist asked quite seriously, "You want a woman's style?"
Lucy responded, "No, a man's style. Well not a manly style. Something a man can wear without looking odd, but something I'll want to play with, run my fingers through."
My hair ended up just past collar length in the front and the back. I could pull it back and tie it or let it down into a layered look.
When we got home Lucy took me into the bedroom so she could play with it.
"Should I get naked?" I asked
"Not just yet, I want to touch it a while," she stated bluntly as she removed everything but her underwear.
I removed everything but my boxers "Alright, but we are going to have sex?"
"Do you need to ask? Just let me enjoy the build up" she came round my back and sniffed at my neck. "I love that smell, that smell of clean soft hair, smells like mine."
"I like that smell too, it reminds me of you. Is that what's it like when you wear one of my shirts?"
She quietly picked up the shirt I'd just taken off and slipped it on without buttoning it, held the collar to her nose and inhaled. Bliss flowed through her and she walked to the bathroom holding each side of the collar in hand. "I like smelling like you, more than I like my own smell. But I never noticed that, did you?"
"You mean your own smell?"
She returned with a perfume bottle. Sprayed a little on each hand then worked her hands through my hair "Yes, it's so funny were rarely notice ourselves. Hehe there now you smell like me."
"It's turning me on. I don't think I could stand your scent all the time, I'd never get any work done."
"Good thing we're not at work. Are you happy... with my body?"
"Well I love that there's no stubble on your legs any more. It's fun to tell you what color to change your hair. I love your smile"
"Anything else about me you'd like to change?" She came around in front of me and laid with her ass between my legs, her weight resting back on her elbows and her eyes gazing up into mine. "It's an incredible turn on."
"Anything at all? You won't think I'm too crass?"
"Sounds like you have something fun in mind." She started licking my fingers. "Dirty boy."
"I'd love to see you with bigger breasts. Sorry you asked." Again I'd expected her to be offended, but she seemed to melt in my lap. "They wouldn't have to be much bigger just a B cup, anything bigger wouldn't suit you."
She didn't say anything, but just laid on my lap a while fondling her cute little A cup breasts.
"Would you like me to get a bigger dick?" I jested.
"No, that's just about ideal. You're just about ideal." She ran her fingers up my neck scratching up my beard.
"Just about?"
"Maybe you could just get your face smooth? Laser it?"
"I read about that online, they say it can make a man look odd."
"Some men maybe. But your face is so boyish anyway when you grow your beard it looks fake."
"You like me smooth don't you?"
"And soft, and your smell."
"Okay." We made love taking turns on top. Exploring and satisfying one another in turn.
A few months later Lucy took great pleasure in buying new tops because her old ones were all "too small". I didn't mind not shaving in the morning, but the texture of my face changed completely, it was back to the way it felt when I was a boy. The skin felt loose and rolled easily against my fingers. Lucy loved it, often she'd ask me to just rest my face against her belly, or on her shoulder, or between her breasts and she'd just play with my hair and purr.
One evening we were watching a show about plastic surgery and I asked if we were done with our game. Lucy said she was happy with the changes but didn't want to go further she thought some of the people on the show looked freakish. She'd seen too many people like that in LA. I agreed, there was satisfaction in being just what she wanted, that's what was important, not the changes.
Things picked up at the office anyway. A little unknown clothing firm we had done magazine ads for had caught on and suddenly became an 'in' clothing firm. Lucy and Kaye worked at designing new ads and I coordinated with the magazines. We were also working long and hard to help them get a catalog out, which was a major undertaking but important to show the bigger chains.
At times I felt I was at odds with the girls. We got a lot of free clothes from the clothing maker and Kaye was in the habit of trying them on throughout the day, sometimes changing clothes two or three times at work. She said she just liked playing dress up. I didn't have a problem with this, at least I didn't think I did until one night just after one of her ads had been rejected from a magazine. I told her maybe if she was a little more serious and would stop playing "dress up" we'd get more done.
She was already overworked and stressed out. That made her cry, she didn't break down, but she cried. Lucy glared at me and went and talked to her in the ladies room for about half an hour. I knocked on the door and said I was sorry, said I was just frustrated and I didn't mean to take it out on her. She came out and I apologized telling her I wasn't acting like very much of a friend and that I was sorry. It seemed to help but I could tell I'd hurt her feelings.
Lucy suggested we all take the morning off, which we did. Lucy and I got in around noon and after I got back from picking up lunch she gave me a message.
"Kaye called, said traffic was really bad that she was just going to work from home today."
"Okay, I hope she's alright. I still feel bad about last night."
"She'll be okay. I think we'll all be okay if we can just get through this rush."
"The ironic thing is we don't have time to hire anyone else. God we need the help so bad, and we need a bigger office, which means even more time."
"Things will be okay, once we get through this. I hope anyway. We're all doing the work two or three people would be doing at larger firms, but hey at least the money is good."
"I still feel bad about chastising her last night. It just doesn't seem like me."
"You're not like that, you won't turn into that either. But I was curious about something."
"Yeah?"
"Why did you get on her case for playing dress up?" Lucy rocked a ball point pen between her fingers like a metronome.
"I don't know just seems like a waste of time, but when I think about it I play web games every once in a while, or go for walks. I guess everyone is entitled to their breaks. Makes us more productive in the long run."
She clicked the end of the pen twice against the table. Retracting, then extending it. "Dress up is probably one the more useful breaks I can think of, sure she takes too long at it but at least she's learning about the product. I should probably do it to, not as much as Kaye maybe."
Our client sent us things just about every day. I suppose they wanted our feedback, or just wanted to make sure we were prepared. Either way our back room was filled with boxes of clothes. Kaye opened each delivery like it was Christmas and would try on everything she could during the day.
Lucy put the pen down and said, "Want to go try? You can help me pick things out."
Lucy stripped down to her underwear and set her regular clothes aside. We went through boxes looking for size six clothes. She tried on everything: dresses, skirts, pants, jumpsuits, you name it and every time she put on a new outfit we'd discuss it, trying to figure out who it was for, and why they might buy it. Eventually she decided to stop and we found her some business appropriate attire, a lacy black and gray skirt suit over a black bustier top.
"How about you Will, want to try anything on?"
"I haven't seen any men's clothes."
"I'm sure we could find something, some pants or a shirt that's not too feminine. You're so thin, female cuts might look fine on you. Also some of this stuff is boy cut anyway, that's a style."
"Like that dress, I'm sure that's boy cut."
Lucy swept up the dress I'd pointed to and held it up to me "Well maybe not this, you have slender shoulders though, that should make this easier."
She went through some pants and produced a pair of black stretch boot cut jeans. "Here try these."
I was surprised how tight they fit, at first I didn't think I could get them on, but once they were in place they fit well. "These feel painted on, they really make my legs look skinny."
Lucy started adjusting my shirt. "Your shirt looks really loose." She began unbuttoning it. "We'll need to find you something fitted. Show off your bod a bit, I think I saw something earlier." Her hands grabbed my shirt at the shoulders and she slid it off my body.
She went to the boxes and started looking through blouses. The first thing see pulled out was a lacy black top, I wondered if she was going to have me wear that, but she set that aside and dug deeper. She pulled out a similar lacy white top, than a pink halter top, she glanced at me, then looked over my body and smiled before setting that aside. Finally she produced a dark silver three fourths sleeved shirt with diagonal stripes. "This isn't girlie, I thought it was a man's shirt at first." It was cut cleanly without anything overtly feminine.
I slipped in on and started buttoning it. "Kind of makes my arms look skinny."
"Yeah women's sleeves can be a lot tighter. Also it bells out at the waist a little. That's supposed to make your butt look bigger."
"It's a different sort of cut. I'm surprised it doesn't feel stiff being as tight as it is."
"Doesn't look too bad though. See we found something you could wear."
"I'm not sure I'd wear this outside."
"Looks good to me. Don't worry about it."
We worked the rest of the day in those clothes. When it came time to leave Lucy didn't want to change back, I was going to, I didn't like the idea of walking around in women's clothes, but then she asked if I'd wait until we got home.
When we got to work the next day Kaye was already there. She looked a bit drab, depressed and she was just wearing a tee shirt and trousers. I told her I was sorry and it was okay if she wanted to dress up. At first this didn't seem to help. Lucy told her we had played a little dress up as well. Kaye looked at me funny. "You tried on clothes as well?"
"Just some jeans, and a shirt," I explained.
"I have a hard time picturing that."
"Why don't you go show her Honey?" Lucy interjected.
We went to the back room and I tired on the clothes I had worn yesterday. Kaye looked me up and down. "Oh that doesn't look too odd. At first I had pictured you in a skirt."
I shook my head and gave her a sideways stare. "No, just pants." There was an awkward pause. "Sorry about giving you a hard time yesterday, I swear I didn't mean it. Feel free to dress up as much as you like."
Kaye raised an eyebrow. "You gonna wear that today?"
"I wore it yesterday, it's a little stinky."
"Would you mind if I picked something out for you?" She blushed when she said this, but I could tell by her eyes was was quite serious and a little excited.
I gave her a shoulder shrug that said, "Are you serious?"
"Come on, it'll make me feel better. Let me know that you mean it."
"I guess no clients are coming in today. Okay but I get to veto anything I don't like."
"Alright."
Kaye kept it simple with a black shirt and gray pants. The shirt was short sleeved with a little tuxedo ruffle at the top. At first I was going to veto it, but I wasn't sure if she'd find anything better. The pants were gray business pants. They were conservative enough but they had a smooth front, the fly was almost hidden. The way they glossed over my man bits was disturbing.
Kaye sent me back to the office. I asked her if she was going to change, she said yes and she'd be out in a minute. At first Lucy gave me a nod as a seal of approval, then she cracked up when Kaye came out in the exact same outfit as mine. They rest of the day Lucy called me "Kaye number 2" and called Kaye "Will number 2," she never used our real names.
Kaye went back to dressing up daily, she'd get Lucy and myself to do it once or twice a week and I'd only do it if I know no one was coming into the office.
A few times when we went out to lunch around Hollywood, Kaye would point to a man and tell me, "See that's totally a woman's cut he's wearing."
I'd usually respond with like, "But I'm not gay."
To which she would say, "You'd just be fabulous," or, "No one cares if you're gay," or, "So what?"
We were about two weeks away from getting the catalog out, I had setup a lunch meeting with a new potential client. That morning to my dismay I spilled coffee all the over my shirt and pants. Lucy and Kaye seemed happy about the whole thing and told me, "see now you have to wear something from the back room." I told them okay as long as you couldn't tell it was woman's clothing. They agreed we poured through boxes quickly until I ended up wearing the silver shirt and black pants and I had worn the first time.
I was nervous, it felt like everyone was watching me. The clients were very flamboyant and they complimented me on my clothes, but they didn't have the money to pay us and were hoping we'd work for a cut of profits that didn't yet exist. I ended up telling them we might but that paying clients would come first.
When I got back the girls asked me how it went.
"Good and Bad. Good in that they liked us a lot. Bad in that they don't have any money to pay us."
Lucy started looking through her books. "That's too bad, but on the other hand, we don't have any extra time right now."
"I'll just be glad once this is all over and we get the final payment."
"Yeah but we have to give most of the clothes back." Kaye looked disappointed. "She said we could keep a few things but that she wanted most of it back for her shop."
"Oh well, guess I'll have to give up women's clothing."
"Too bad we never got to really dress you up."
"What do you mean? I let you pick outfits for me all time."
"No I mean... just Kaye and I have been kind of curious," Lucy said while fixing her lipstick.
"Curious how?"
Lucy continued with her lipstick and Kaye picked up the conversation "It's just that you're so pretty. You look good in those clothes. Better than you do in your clothes anyway. Just makes me wish you'd let go all out sometime."
"You want me to work in drag?"
Lucy finished her lipstick and took over for Kaye. "No silly not work. Just let us dress you up some evening, maybe on the weekend."
I looked put off, but I had enjoyed the clothes. It just felt weird to admit it.
"Please, please, please. Just once after we finish the catalog but before we return the clothes."
"Maybe, but I'd have to approve of all the clothes first."
"Ah come on, that's half the fun. We want to dress you up any way we want."
"This sounds embarrassing."
"While we do mean as feminine as possible, but nothing we wouldn't wear. We'll dress about the same, you'll fit right in. We'll make you one of the girls."
I looked at Lucy and saw how excited she was when she said that, like she was being coy or seductive, the way she talks about being bisexual. I could tell it was something she really wanted. It turned me on when she talked like that, there was something very sexual about it.
"If we get done on time, okay."
I had mixed feelings when Kaye and Lucy started pulling 12 hour days. It was great they were working so hard, but I'd rather they'd worked so hard because they wanted to succeed in business, not because they wanted to succeed at getting me into a dress. We finished the catalog a full three days ahead of time and got paid the day after that. When I suggested taking the rest of the week off Lucy and Kaye informed me that they'd be picking outfits in the morning and would come get me in the afternoon.
That night as we got ready for bed Lucy brought it up to me.
"I'm so excited about tomorrow."
"Glad I could provide some motivation."
"It's been a fantasy of mine you know," she draped her arm over my belly and padded the side of my ass "I've always wanted you as my girlfriend."
"You don't like me as your husband?"
"Sure I do, but I like sugar and spice too and I haven't had it in such a long time." She drummed her fingers against my belly. It tickled in a very erotic way I was getting turned on.
"If you ever need to be with a girl, I'd be okay with it. We could do a threesome?"
"No Honey I like you best, just sometimes I think I'd rather you were a girl. I love your smooth soft body, and the sweet scent of your hair. You'd make a better girl than a boy." She reached down into my underwear and held my penis.
Lucy giggled when I said, "You should have married Hank." Hank had been her boyfriend before me in college. He ran track, and was a second string running back on the football team.
"You know," she replied, slowly working me out of my boxers. "I once got Hank into my underwear."
"How'd you do that?" I kicked the boxers off with my feet and they fell to the floor. Lucy swept her hands over my thighs and rolled off the bed.
"I denied him sex. Told him if he wanted in my panties, he'd have to be in my panties... as a gesture of commitment." She opened her underwear draw and started going through it.
"What'd you make him wear?"
"The frilliest pink panties. I went out and bought them just for the occasion." Lucy held up a pair of black and pink lace panties displayed them to me, looking me in the eye and closed the drawer. She sat by my feet and caressed them, touched the lace of the panties against my toes, then hung them over both my feet and started working them up my legs. I looked down at my legs, smooth and hairless, the panties made them look just like girl's legs. I'd become erect and Lucy pushed them up as far as they could go. She took my penis into her mouth and began to suck. I didn't take long I came almost immediately and she swallowed the whole load. She lay there with her head on my thighs, licking me clean. Once I relaxed she took my penis, tucked it back between my legs and pulled the panties the rest of the way up so that they held everything firmly in place.
The next morning when I woke Lucy was already gone. By the time I ate breakfast and showered, she and Kaye were waiting for me downstairs.
"It's that day isn't it. You have everything?"
"We have a few things for you now but we're going to take you into work, be a shame not to try a few looks out. Glad you're not dressed yet. Kaye stay here while I go get her ready."
"Her?" I asked. Lucy took my hand and led me back up to the bedroom. She opened a package filled with feminine things.
First thing she had me strip, then she took out a black lace bra and looped it over each of my shoulders and hooked it in back. It pinched my chest as I breathed. I slapped my hands against the empty cups in front. On cue Lucy took two large breast forms out of the bag and placed them in the bra. They were cool and tight against my skin, but as the heat of my body warmed them and they felt more natural. If Lucy's own breasts were a B cup these must have been at least a C. They had nipples on them which I thought odd until Lucy took them each between her fingers and pinched.
Rolling two dark stockings up my legs, her fingers picked and prodded at the nylon until the seam ran straight down the back. She hooked a garter belt around my waist and pulled at the strap until it fit snuggly. Lucy grasped the front and back of each stocking in turn hooking them to the belt. The surface of the nylon pulled against my legs. When she released It they went loose for a moment and cool air flowed round my thighs.
The last piece was a padded black pantie. The thick padding felt odd at first like a diaper but it was comfortable and made my ass stick out like a girl.
Lucy handed me a pair of pants and a neutral blouse she had taken from the office and I put them on. At this point just looking at myself in the mirror I looked like a woman. My smooth face and long hair did nothing to betray my true gender. I didn't look girlie or too feminine, just like a woman who had gotten dressed for a casual day.
My sneakers hardly matched, but Lucy told me we would buy something later.
When I came down the stairs Kaye exclaimed, "Look at you, you have boobies."
"They're fake."
"Don't worry Honey I won't tell anyone." Lucy grabbed my ass. Which might have been better without the paddling.
"So can we still call her Will?" Kaye asked, she and Lucy started going back and forth about it.
"I've never heard of girl called Will, maybe Wilma, but that's kind of old lady slash Flintstones."
"What about Willie?"
"Wouldn't that be like calling a man Pussy?"
"It think a Willie is a man pussy, we could call her Pussy."
"Or Kat, as in Pussy Kat."
"What about Billie?" I said.
"That's more of a man's name."
"Can be a girl's too though."
"Well it's the only one that's still technically my name isn't it? They used to call me that when I was a boy."
"But we called you Will when you were a boy. Oh, you mean when you were a kid."
We voted on it just like we voted on office matters. Kaye and I were good with Billie, but Lucy wanted Kat. Billie won. I felt like a pervert at first, walking around with big breasts that bounced whenever I moved faster than a walk. I jogged a few times intentionally just to feel it. My face looked androgynous, slightly male, but on top of that body no one would guess. Of course we live in a part of town where you see trannies everyday, just that I hadn't expected to be one.
The office was the same as ever, and we went to back room to play dress up as we often did. The only difference this time was that I didn't get a vote. Any time I would try to say something or complain Lucy would stop me, the first time she shushed me, the second time she kissed me, the third she squeezed my checks together.
It seemed like Kaye and Lucy were in a competition to see how girlie they could make me. Thank God the bright pink party dress was a few sizes too small. It didn't look right either, too little girl, like I was overdue for a spanking. They tried some baby dolls which again just didn't fit my frame. All this was odd for guy who'd never worn anything without pants before. I'm very open minded but it was embarrassing to have them treat me like a doll, but that's exactly how how they put it, I was their dress up doll for the evening.
Thankfully, the girls started disagreeing over how they wanted me dressed. Lucy wanted more of the call-girl evening gown look, and Lucy was going more for cheerleader on spring break. Honestly I had fun with some of the more extreme looks but it occurred to me that we were going to go out, and there was only so much I could take. They eventually decided that they would each choose an outfit for me, and then I could choose between them. I liked this because they started thinking about what I might want to wear out if I were a normal girl rather than a prostitute. The other stipulations were that they couldn't show each other before I chose and then we all had to dress to match.
Kaye choose a rocker girl look with black leather pants and black crop top. Lucy chose a deep dark red evening dress with black sequin trim. I tried them both on at first thinking I would go with the pants but when I put on the evening dress, it just felt good. In a way it felt like being naked. The dress just hung around my body affording neither protection or utility, making it like my body was a work of art. It made me feel beautiful. While I modeled, Lucy couldn't help herself, she kept adjusting the dress, making it fit perfectly and running her hands along my body.
I chose the dress and the girls looked for similar clothes. Kaye found a little black dress, and Lucy a blue dress that draped over one shoulder in a way reminiscent of ancient Rome. The dresses were elegant but short, coming to just below the knee.
We found three short black coats to wear while we went out shopping. The next stop was the salon. Lucy told me she had told the stylist an advance what we were doing, but apparently Adrianna hadn't paid to much attention. It took her a few seconds to recognize me, and when she did her mouth dropped. Then she asked if I was going to be a girl now, "Full time."
I said, "Just for tonight," and Lucy remarked coyly, "We'll see."
We talked about styles and Adrianna suggested things that could be pulled back to look okay on a guy, but Lucy interrupted her and said, "Just make her look as beautiful as possible, if we need to we'll come back and get her hair cut short." They settled on an asymmetric bob in front with hair cascading down my neck from the ear back. It fell forward and swept over the hairline so that the shape and frame of my face came from the style alone. The style was sleek and followed the shape of my head and neck. It was in essence a long "pixie" cut.
My naturally dark brown hair was lightened in layers. The bottom remained dark, the bulk of it became a light auburn, with a few light blond highlights on top. Not girlie girl, but rather a sophisticated feminine look a man would never wear. My eyebrows now looked heavy and strong in contrast with the much softer look of my hair. Adrianna shaped them into clean arches, but not too thin, she used bleach to lighten them a few shades until they blended in with the rest of my hair.
Adrianna said I didn't need much makeup but seeing as they might not get the chance again, Lucy and Kaye insisted on something "fun" and "maybe a little over the top". Adrianna applied a smooth opaque liquid foundation to my face. It matched my complexion but completely covered it giving my face a porcelain uniformity so I could get properly "dolled up."
Just a very light pink blush and eyeshadow kept the smoothness of my face. She followed this by applying a dark but thinly well defined eyeliner and mascara that made my eyes look like a line drawing on bright paper.
The lipstick was dramatic. I'd never seen it from a bottle before assuming it only came in tubes. Adrianna used a little sponge brush like applicator and swept it across my lips like paint. She told me to blow on it for a few seconds until it dried. Then she applied a clear gloss over top to keep it sealed. I was surprised none of it smeared off on my finger when I touched to test it. It felt like my lips were that smooth dark plum color rather than just wearing it.
The overall effect was staggering. I could no longer see a man at all and Lucy and Kaye would have seen me blush had the makeup not covered it, but it wasn't a blush of embarrassment. I always blush whenever a really pretty girl makes eyes at me.
Lucy and Kaye got their makeup done as well, but I hardly paid any attention. I just keep looking at myself in the mirror, making pretty faces for myself and smiling. To finish we all got our nails done. Mine matched the plum color of my lips. The polish made the surface of the nails smoother but sticky it a way. Not wet or messy, just that they gripped smooth surfaces and held to plastic like a tire grabs the road.
My shoes were horribly out of place as I'd just worn old canvas sneakers. We went passed a few expensive shoe stores on the way to a larger discount one. I asked why we didn't stop at those until I saw the price tags in the window. Some of those shoes were more expensive then my television set and we could go out to eat at a really nice restaurant for the price of the cheapest.
The shoe superstore was less posh but we had fun. At first the girls brought me slender sandals and stilettos that looked great with the dress but I could hardly even stand up in them. I settled on some black shoes with shorter thicker heels that I could walk in. They bought me a small black purse and had me transfer my id, credit cards, and cell phone, then added some makeup from the salon. Lucy asked me for my empty wallet and old shoes. She dumped both in the trash explaining I needed new ones anyway.
Lucy touched my shoulder and went round behind me, she nudged my chin up with her finger and clasped a thin silver chain with a small diamond pendant round my neck. "You look so beautiful," she whispered.
We spent most of that night in West Hollywood, I'd seen crossdressers in that part of town without any issue. We ate at a place that was half club, half restaurant. No one seemed to catch on that I was a man except the bouncer and he was more impressed than surprised. If there's one thing I was worried about, it was being hit on by guys. The few times a man did come up to me, Lucy ran over to say she needed me and then we'd go and make out.
Kaye was very amused by the whole situation and keep daring me to see what I could get away with. She went with me to the ladies room which felt like an enormous faux pas, like a high school pervert invading the women's locker room. We had to wait in line and I kept my attention firmly on Kaye. She noticed this and stared back and made funny faces. I cracked up feeling a bit more comfortable.
Later that night she got me away from Lucy and asked if I'd come along while she went up to a guy she thought was cute. He was the tallest guy in the place, very lean, very muscular. He wore a dark suit and looked like a really nice guy, the type of guy I hated as a man because all the girls would pay attention to him. I went with her to talk to him. She introduced us and asked him his name, it was loud so I couldn't hear what he said, then she pointed over at me and told him, "You know, I think my friend likes you."
I started coughing as he gave me a warm smile, my face went flush red and I quickly turned around and went to find Lucy. When Kaye found us a few minutes later, she was cracking up. I passed the guy a few more times that night and each time he'd try and give me his 'James Bond' look.
We stopped by a few bars before catching a cab home. It was surprising how friendly everyone was when I was out as a girl. People held doors for me, and later on a group of guys bought us all drinks.
Lucy was all smiles when we got home, it wasn't early but it wasn't late either and we ended up on the couch. Lucy started running her fingers through my hair, then she held my hand in hers and ran her fingertips against my polished nails.
"Did you have a good time tonight Billie?"
"Yes... it was a lot of fun. I was glad nobody gave me any trouble."
"I don't think you have to worry about that. You just have to worry about cute guys hitting on you."
"God that's so weird."
"Are you saying you like girls better?" Lucy ran her fingers down my thighs.
"Yes."
"I like girls too." Her fingers traced along my calves, down to my shoes and unstrapped them. "Want to know something?" she slipped my shoes off, dropping them to the floor. "I think I like you better as a girl."
"Thanks... I think."
"I like you as a boy too, but if it were up to me I'd have you as a girl all the time," she caressed my shoulders.
"Thanks... but I don't think I'm going to be doing that."
She gazed into my eyes and my whole body felt warm. "Let me have my fantasy, just for tonight. Even if it's a little white lie, I can't help but wanting to seduce my new girlfriend."
If she wanted to play at this, what harm could it do? Even if it was just a game, I'd had fun tonight, and Lucy was really turning me on. I decided to play along, "I do like looking this way, and the dress is wonderful."
"And your hair and those lips of yours, do you love those, sexy bitch?" Lucy laid me back and straddled me, her arms arching to either side of my head.
"Yes." I smiled. "I love being your sexy bitch."
The next morning I showered and got dressed but with my hair styled and my nails colored. I still looked much more like a girl than a boy.
"Hey Lucy, I need to get back to the stylist, I think I still look a little too girly."
She giggled. "Your face looks a little odd without boobs."
"When do we go back?"
"Whenever, I can make an appointment if you like. You don't need to go out today so what's the hurry?"
"I dunno, it just feels odd to still look this way."
"You'll get no complaints from me." Lucy grabbed my ass.
"Glad you're enjoying it at least."
"Well I'm not in any hurry to see you cut that cute hair, it'll be a while before it gets that long again. Besides we're done with the catalog, you can stay home this weekend. I just gotta be there when they pickup the clothes, but it's not like you have to come into work."
"Oh alright, first thing Monday morning though."
"Okay, I'll call and make the appointment right now. Take some time off this week. You work harder than anyone, No point in going in until we have some clients."
"Sit on the couch all day?"
"Whatever you like. Play games all day, get drunk first thing in the morning. Just take some time off."
"I think I'd get bored. I'll see how I feel after Monday."
I stayed at home that weekend. Lucy went in so the client could pick up their clothes, and when she came back she had two boxes with her.
"What are those?" I asked.
She looked excited. "They let us keep a box each. That's easily worth a thousand dollars. I picked up the stuff you've worn in case you want it."
"Oh, those pants and shirts?"
"And the dress too, I thought that'd be fun to keep."
"I let Kaye fill out the rest of your box, she has better taste anyway."
I started looked through the box. Mostly it was jeans and some neutral looking patterned tees. At the bottom I found three suits. The first was a gray pants suit, followed by two skirt suits, one blue and one charcoal.
"Looks like she got me some skirts, great. She knows the dress up thing is over, right?"
"Your hair appointment isn't until early afternoon, and she said I should try to get Billie to come into the office that morning just for kicks."
"Great, you two are having a lot of fun with this."
"It's gonna be a slow week, we don't have anyone coming in until next Monday. We need to amuse ourselves anyway we can. She's bringing in Scrabble too. Besides, I think it's cute. We'll all do whatever you want to do on Tuesday."
"Can we do guy stuff like eat raw meat and go to a monster truck rally?"
"Sure why not?" Lucy seemed pretty casual about the whole thing, plus I wasn't sure how well I'd be able to not look like a woman until I got my hair cut so I agreed.
Monday morning came around and I ended up wearing the charcoal skirt suit into the office. Lucy bought me some cotton panties and another bra so I wouldn't have to wear the dirty ones. I didn't wear much makeup, no foundation and just lipstick and some eyeliner, it was still more than enough to sway my face over to looking female. I brought in a bag of my guy clothes for the afternoon.
Kaye was surprised but happy to see me as Billie. Work was slow and we ended up playing Scrabble first thing. We discussed my look as a bit of a joke between rounds.
"What do you think Kaye? I think Billie would make a sexy boss."
"Maybe, but Will always gets to be the Boss. Besides Bosses all dress casual these days. I think she looks more like the sexy secretary."
"Don't I even get to be the intern?" I asked.
"Sure if you want but they don't even get paid, plus you're way to hot to be the intern. Why go to school when you can get by on that cute little ass of yours?"
Kaye raised her hand and spoke, "Okay whoever wins this game decides all our jobs for the day. Boss, secretary, or intern."
Lucy ended up winning the game. She declared herself the boss, Kaye the intern, and me the 'sexy' secretary. We played each of the roles as a bit of a caricature. Kaye whined and made a lot of stupid design comments, Lucy kept telling me to get her coffee or pens or to take notes, and I started calling Lucy and Kaye Ms. Lynes and Ms. Henton. But mostly we just played Scrabble.
My hair appointment wasn't scheduled until 2:00. At 12:30 we had a bit of a shock when a man came into the office. He said he was from the landlord and asked if William Lynes was around. I didn't know what to say. Lucy jumped in and said she was Ms. Lynes and that Will was out today but she was in charge. He said the shop below us was moving out, he knew we wanted more space, and asked if we would be interested. Lucy said we would be and then offered him a drink. The man asked for coffee and then Lucy looked at me.
"Two coffees please Billie."
At first I didn't realize she wanted me to get them coffee.
"Two coffees please Billie," she repeated herself.
"Oh sorry Ms. Lynes," I said and then asked them how they took it.
It was odd to play secretary seriously, but I didn't feel like explaining the whole crossdressing thing. Lucy and Kaye knowing was one thing, but I didn't want my business relations to know. I'd only met this man once before in person, but that was brief and I hadn't had long hair or was wearing makeup and a skirt so he didn't recognize me.
I did my best to help, they had gone into my office to talk about the details. Lucy left the door open and I could hear everything but it was odd to have business going on without me. We had said we wanted that space if we could get it so there wasn't really any new discussions being made. Lucy did a good job, talking with authority and getting everything on the way.
The meeting ran long so I called the salon to see if I could move my appointment back. I was surprised when the woman on the phone told me, "Oh sorry, Adrianna is out sick today. We rescheduled you for Friday at two is that okay?"
"That's kind of late. I'd really like something today."
"Sorry two of our girls are out sick, I don't know when they will be back. The best I might be able to get you something early on Thursday around 7:00 in the morning." I kept a late day, usually getting at around 9:30, so I hated getting up earlier.
"Do you have anything later on Thursday?"
"No, we already rescheduled all the appointments. It's just until Friday. We can't promise anything earlier than that. Sorry about that, would you like me to call if we have a cancellation?"
"Yes please."
"Okay but otherwise Friday at two, okay?"
"Okay."
"Okay, bye."
Lucy and the man finished their meeting.
"I thought you'd be at the salon?" Lucy asked.
"Adrianna is out sick and the soonest they can see me is Friday."
Lucy smiled instantly. "Oh it'll be fun to have a secretary around the office until Friday. Actually if we want to get the bottom floor we have a lot of work to do."
"Don't I need to be here to sign the contracts?"
"I told him you were out of the office this week but that I'd fax you everything. He's coming back tomorrow or Wednesday to go over the agreement, then he's coming back on Thursday to get the signed papers."
"Just great, maybe I'll just stay at home."
"Come on Billie, I really need you around." Lucy looked worried. "Seriously, I don't know where any of the old stuff is filed."
"Fine, I suppose I can put up with this for a little while longer."
Lucy touched my shoulder "This is a fantasy for me you know, I'm really going to enjoy this week, thank you." She kissed me softly on the cheek.
Things got complicated after that. We got the office space cleared away on Thursday, but a new client came in that afternoon, they just popped in. Two of them, a man and a woman representing a large electronics retailer that was trying to appeal to women. They had seen our previous work and wanted to sell electronics the way we sold clothes.
I played secretary and ran in and out as Lucy discussed numbers that were ten times the amount of our last deal. They came in every day for a week, hashing out contracts. There was no good breaking point for me to go back to being a man. Eventually they asked where William Lynes was, Lucy told them I owned a few businesses but that she ran things here day to day. I stayed as Billie for a few weeks before Lucy called a meeting.
"Billie, we ran into a little snag today with the contract."
"Really, are they pulling out of it?"
"No they want to go ahead, it's so much money we're going to all be rich soon."
"So what's the problem?" Kaye asked.
"Thing is they need all the officers of the company to sign the contract with them and with a notary present." We all had equal stake in the company, but I was President and Lucy was Vice president, Kaye wasn't officially anything but she liked to stay out of the business.
"So I need to come clean?"
"Thing is they're worried about their IP. They need NDA's from all the officers so we can't sue them. They were absolutely insistent on it."
"Okay...?"
"They are very paranoid about it. They kept saying they trust us but they don't know about Will because they haven't met him. I'd rather not take any chances about scaring them off, especially since we've been lying about Will."
Kaye raised her hand. "I know, just make me president."
"I was thinking I'd be president and you Kaye would be vice president." Lucy looked at me sheepishly.
"What am I going to be then?"
"A large stockholder and the secretary? I was going to tell them William left running the company to us. We can't give you an officer position without exposing the whole thing."
I just sighed. "So I go from running my own company to running coffee?"
"Sorry Billie, you don't need to run coffee. It's a lot of money, we can get it delivered. Look I'm sorry this must be weird for you, but just put up with it for the duration of the contract and then we can all retire. I really need you around to help with the business stuff, that's the sort of thing secretaries do so it wouldn't look odd with you helping me."
"How long is that going to be?"
"Maybe six months... maybe a year," Lucy said looking both sorry and excited at the same time.
That night I resigned as president of my company and took a job as secretary. The president which was now Lucy had double voting rights, her stock counted twice at board meetings. She had the control I once had, so there was no way to get control of the company again without her. She kept saying it was only temporary, but she'd also confessed she loved being my boss.
We were kept very busy with the new contract. People from the electronics firm were in two or three times a week they got to know me very well, and they seemed to respect me once Lucy told them I owned part of the company. Lucy grew into her role quickly, she moved into my office and I took up the reception just outside her door. We were overworked within a month and Lucy hired two more designers and an intern. They never knew I was Will, but only knew me as Billie.
The next pay period I was shocked to see my salary had been cut in half. I went in to ask Lucy about it.
"Honey, what happened to my check?"
"Hehe, I thought it would be fun, that's what secretaries make."
"You lowered my salary for fun?"
"Don't worry Sweetie, we're married anyway. I raised my salary to compensate."
"But we have separate bank accounts."
"Don't you worry about that. I'll just pay the rent from now on, that'll even things out. Plus we have the same credit card. I'm looking forward to complaining about you blowing all our money on clothes and makeup..." She rolled her eyes innocently. "Or a boob job."
--END--