It's Complicated

I saw her walk in, I'm sure everyone in the restaurant did, it's hard to miss a tall, beautiful, stylishly dressed woman with flaming red hair. She was talking to the hostess and scanning the room. I was doing my best not to stare at her and failing miserably. When she saw me, I could feel myself blush, she smiled, said something to the hostess and headed in my direction. I looked around to see who was behind me only to realize I was sitting in the back corner of the restaurant; she was here to see me. I just watched as the goddess floated up to my table and asked if she could join me. She sat down before I could answer.

"Um, I'm sorry, do we know each other," I was trying to remember how to breathe.

"Hi, I'm Carla," she put her hand out to shake mine.

"Yeah, uh, I'm Michael, um, Mike," I shook her hand, her grip was firm, her long, perfectly manicured fingers wrapped around my hand, the pink on her nails the perfect contrast to her hair, the softness of her skin sent tingles up my arm and I was pretty sure she rubbed the back of my hand with her thumb. I held on to her hand too long for a handshake and just long enough to get even more uncomfortable if that was possible. "So, what can I do for you, Carla, you were obviously looking for me," I fought to regain some sense of composure?

"Yeah, about that," she paused and stole one of my fries," look, I now this is weird and maybe out of line, but I've seen you every day, twice a day for the past week; you stop outside Tanners, the dress store where I work, and look at that pink dress in the window like it was a puppy, well, I think you're kind of cute and I was hoping one day you'd actually come in the store and maybe I could meet you, but you never did, " she was rambling, she was as nervous as I was which made me smile," shit," she paused," Listen, it's going on the discount rack tomorrow. I guessed you're an eight, maybe a ten, so I put one of each in the back in case you wanted to come try one on, that's it; and I wanted to meet you," a subtle blush caressed her cheeks and she smiled a sheepish smile," so, is that too weird?"

I couldn't tell you what it was about that dress, it was a simple vintage button up dress, pink with darker pink flowers, mid length, probably a cotton blend, it had pearl buttons up the front and a scoop neck with cap sleeves and I was jonesing for it hard.

I had been cross dressing since I was five or six, starting with my mom's slips, which I wore as dresses or nightgowns, gravitating to stealing my sister's panties and then a few of her dresses. When I got to college nothing for a while except a random dalliance when someone's panties got mixed in with my laundry or the one time my girlfriend convinced me to dress in drag for her sorority costume party, it hadn't taken much convincing and I had enjoyed it more than I ever let her know. It had never been a sex thing for me, just something I enjoyed and that had helped me relax. I had kept the 'costume' and wig, when I graduated and moved across the country for my new job, found dressing again to cope with the stress of starting a new life.

The internet was my fix, I had bought panties, simple cotton bikinis, and some bras, none of which fit quite right, a handful of dresses, some skirts and tops and a few nightgowns, the dress Carla was talking about was becoming an obsession that I didn't know how to handle; I was sure they would have me arrested if I went in and asked about it, much less asked to try it on.

"You would let me do that," I asked incredulously?

"Sure, why not? We have guys come in all the time, some pretend to be buying stuff for their girlfriends, others aren't shy about it at all and I work on commission, so," she smiled at me and winked, stealing a sip of my water.

"I never thought, I mean I'd be too embarrassed," it occurred to me I had just admitted my greatest secret to a total stranger and she hadn't looked at me like I had two heads, in fact, she had acted like it was completely normal.

"Let's do this then, I'm closing tonight. You come in after work and we'll use one of the private fitting rooms. I'll measure you to make sure of your sizes and I'll even pick out a few things for you to try on. It will be fun. If you buy something great, if not, at least we get to visit a little, it can be like a first date" she smiled at me.

"First date, huh," I smiled back," Are you always this aggressive with your sales," I snatched the fry she was trying to steal from her fingers," and if you're hungry, I'd be happy to buy you lunch."

"Actually, no, I can't believe I followed you down here. Normally, I'd never do something like this, I just wanted to meet you and thought when the dress was taken out of the window, you'd never stop by," she blushed again, this time her face was beet red," and I'm not really hungry," she stole another fry, "I just nibble when I'm nervous."

"You wanted to meet me, why, I'm nothing special."

"You kinda are, I mean you're really cute, tall, thin, blonde hair, blue eyes and a nice smile, and you like dresses which makes you interesting, or at least someone I can talk about my work with," she let out a little laugh and I was pretty sure I fell in love with her on the spot.

"And why would a gorgeous woman like you be nervous, you must have guys fighting over you all the time?"

"It's harder than you think, a lot of guys are afraid, or just after the superficial stuff, when things get real, they run as fast as they can. It's just so, so complicated. I know I'm pretty but sometimes that can be the loneliest thing in the world," I could see the tears welling up behind her crystal green eyes.

"You really think I'm cute, not handsome or striking or gallant or debonair, but cute," I emphasized the word cute which got the laugh I was looking for.

"Could be worse, I could have said pretty, she giggled and the tears that had been coming disappeared, it was my turn to blush a little, I would have taken pretty in a heartbeat.

We talked for a bit longer and I walked her back to her store agreeing to stop by after work for a session of dress up, the rest of my afternoon was spent trying to focus on my work while I held a heated debate with myself about whether it was the dress up of seeing Carla that had me more excited.

It was almost as if he knew I had something planned; at 4:30, Steve, the senior analyst on my team, dropped the Mc Phearson file on my desk, four inches of pure chaos," Bill wants this ASAP, you don't mind do you," he turned to leave, not really waiting for my answer," Just put it on my desk when you're done." Steve had a habit of dumping stuff on me and the other junior analysts, we were pretty sure he was taking the credit for what we did, but couldn't prove it and none of us had managed the courage to call him on it, and that snarky smile, I swore, one day I was going to see it wiped off his smug face. It was 7:30 before I finally quit for the night, stuffing my computer and Mc Phearson into my briefcase, I headed out the door almost forgetting about Carla and our 'date.'

The dress was not in the window when I got to Tanners, replaced by an equally cute sundress, white with lavender butterflies flowing up from the hem, I could see Carla busying herself with straightening some of the internal displays and refolding a few items that probably didn't need it, I took a deep breath and opened the door, taking my first venture into uncharted territory," Hey, I got tied up at work, it looks like you're closing, should we do this another time," it was a tossup as to whether or not I wanted her answer to be yes or no?

"I thought for a while you weren't coming," she sighed heavily as a look of sadness lifted from her face, "and It's Tanner policy that we have to stay as late as necessary if a customer is in the store, I do get to lock the door at eight, so this is actually better, nobody else will be here," she gave me a wry smile.

"You know, I've never actually done this, I mean gone into a store and tried stuff on. I've bought some things online and stuff, um, so how does this work," I could feel my face turning red and a warm flush rose from my neck?

Carla took my hands in hers," first, you need to relax, this is no big deal," her green eyes and easy smile were helping," Like I said at lunch, we have guys in here all the time, it's more common than you think; men wearing dresses, I mean. Second, you trust me, you're in good hands, I picked a few things out I think you might look good in and you can look around and see if there's anything else you like and then we take it all in the back and you play dress up for a while, I'll give you my honest opinion and you decide what you want to do from there. Sound like a deal," she smiled and squeezed my hands?

"Like that sundress in the window, with the butterflies," I started to relax?

"Oh, you like that one, do you, "I nodded," great, it is really cute. Now I do need to take your measurements, so I know for sure what your sizes are. This can be a little, um, intimate, I guess is a good word, you'll need to strip to your underwear so I can do it right," she dropped my right hand and squeezed my left, leading me to the back of the store to the private dressing areas.

"I think you just want to see me almost naked," I laughed.

"Maybe a little of that, too," she came right back," but really, it does help get the sizing right, and there's complimentary wine, if you'd like."

"That would be nice," I kicked my shoes off and started to unbutton my shirt," what the hell am I doing," the thought screamed from the back of my head. I ignored it and laid my shirt over the back of a chair.

Carla measured my neck, my shoulders, my arms, my chest, in three places, my waist and hips, my inseam, doing her best to pretend to ignore the very obvious bulge my panties were failing to hide, she even got my shoe size, writing it all down in a small notebook, I finished my first glass of wine while she was taking the measurements, hoping I didn't squirt all over her while she worked. "There, that wasn't so difficult now was it," she draped the tape around her shoulders and looked at my lean runners body," Interesting, we're almost the same size, you may even fit into a six, are you ready to try some things on?"

The first thing she brought me was a heavily padded push up bra," this will help the clothes hang properly and give you a better idea of how they really look," her demeanor was so matter of fact, I didn't even pause.

I took the bra and gave it a quick once over,"36 a," I thought to myself, "no wonder none of the ones I had bought online fit, they were all way too big," I slipped it on and Carla showed me how to adjust what little chest I did have into the bra and helped me fasten it behind my back, it was actually comfortable and while I didn't fill it up, the ample padding gave me a very nice feminine figure.

Carla brought me a second glass of wine and the pink dress I had been fantasizing about, I could barely contain my excitement, I slipped it on, Carla helped me button it up, it fit very snug against my body and I found I liked that very much," Um Carla," I could feel my face turning bright red," I kind of have a problem, this usually doesn't happen to me when I dress, but I, well I don't want to ruin the dress, I am so embarrassed," I started unbuttoning the dress and turning away so she couldn't see my now raging erection.

"Oh my," she laughed, "I wasn't expecting that."

"Me either, I swear, this never happens, maybe I should just leave," I felt so humiliated. I handed her the dress and reached for my clothes.

Carla put her hand on my arm," or, there's a bathroom over there, you could, I guess, take care of things and we could continue, I mean if you want to, it's up to you," there was an almost hunger in her eyes and a sadness behind it, I got the feeling that her dressing me up was important to her, maybe as much as it was to me. I went to the bathroom and it didn't take long before I covered the tissue in my left hand with warm sticky goo.

"Well, that was definitely a first," I joked about what I had just done, Carla just smiled and handed me the dress, acting like nothing out of the ordinary had happened. I was quickly comfortable again and put the pink dress back on, relishing the feeling of the delicate fabric over my body and enjoying the feel of the dress as it flowed around my legs, doing a little spin as I admired myself in the mirror. It was a wonderful feeling.

The sundress from the front window was next and I liked it even more than the pink one, my keep pile had begun. The next three hours were magic, Carla brought me outfit after outfit, dresses, skirts, pants, shorts and tops, pantsuits, even shoes, some I loved, some we both laughed about and others Carla tried to talk me into, sometimes she won, sometimes not. When she rang me up, even with her employee discount, I had spent well over a thousand dollars and had loved every minute of it.

I walked Carla to her car, "I saw you, taking mental notes while I was trying on my new clothes, Carla, what is really going on, why are you doing this for me?"

"It's complicated," she looked away from me," mostly because I find you very attractive and I like you, maybe more than I should considering we just met.

"It's more than that, the way you watched me tonight, please explain it to me, maybe over dinner tomorrow night."

"I'd like that," she gave me a soft smile

"You know, I really had fun tonight, maybe the best first date ever," I laughed.

"It was really fun, I'm glad you enjoyed it and you got some really cute outfits, too. I hope you enjoy them; plus, there was that bonus," It was her turn to laugh.

I could feel my face turning crimson, realizing that little incident would be brought up for as long as I knew Carla, and possibly longer. Her green eyes, that sweet smile, "Carla, can I kiss you goodnight," I asked before I knew what I was saying?

"I'd like that, too, but remember, I warned you, it's complicated."

"You are smart, funny, and the most beautiful woman I have ever seen, I'll take my chances," I leaned in and met her lips with mine. It was soft and gentle at first, quickly becoming raw and passionate as I dropped my bags an pulled her close, her lips parted and our tongues began to dance, chasing each other around her mouth and then mine as my hands began to explore her back. I could feel her muscular body beneath her blouse, sliding my hand down, past her belt and onto the delicate linen of her pants; she stopped me when I got to her ass, gently pulling the invader back above her waist," Not yet," she whispered in my ear as she pulled away.

"Wow, that was something," I tried to catch my breath.

"I told you I liked you," she smiled at me.

"So, seven? And I'll need your address," she wrote it down for me.

"See you at seven and don't be late," she gave me another quick kiss and climbed into her car. I stood there mesmerized as I watched her drive away, the magnetism we shared, the raw primal attraction was almost too much, I picked up my bags and smiled all the way home.

Saturday morning found me in an exceptionally good mood, I took a quick shower and made myself a cup of coffee, returning to my room to get dressed, I started to put away the new clothes I had gotten the night before, quickly deciding that the stuff I had bought online just wasn't going to make the cut anymore. I cleared out a section of my closet, hanging the new outfits with care and placing my new shoes on the shelf above. When I found the bras at the bottom of the bag, I chose the pink one and slipped it on, adjusting myself as Carla had showed me, deciding on the pink dress that had started the whole adventure and adding a pair of sandals to complete the look. I slipped on my wig, brushed it out and spent a few minutes admiring myself in the mirror before I moved to my office and started to tackle Mc Phearson.

I completed my analysis and was putting the finishing touches on my proposal when I realized that it was already five o'clock and I still hadn't even looked up Carla's address in Google Maps to figure out how much time I needed to get there. A quick search told me it was only about thirty minutes away, I relaxed a bit, reread my proposal, it was possibly the best work I had done for Carter-Bergman since I had been hired and it pissed me off a little that Steve was going to take the credit, again. I decided to take another shower to get Steve out of my head and, well, just in case.

I shaved twice and combed my hair into a fairly androgynous look, slipped into a clean pair of panties, I had chosen a pink pair with the lace trim and a satin bow in front, the bra I had been wearing earlier actually matched them. I chose my new linen slacks with the high waist and thin belt, a matching blouse, and a pair of low heels to complete the ensemble. Dropping my wallet and keys into the small purse Carla had suggested and full of trepidation, I locked the door behind me and hoped Carla approved. It would be the first time, except for the party in college, I had ever left the house in women's clothes.

To say Carla approved would be an understatement, she absolutely glowed when she saw me," I like what you chose," she kissed me sweetly," but, um, can I make a suggestion,' she kind of winced.

"Sure, you are my fashion expert," I smiled at her.

"Well, it's not the clothes, it's um, your friend, he kind of messes up the look. If you'll push your bits up inside and tuck him back between your legs, it will make him not so obvious. Pull your panties up tight and it will help keep him in place," her wince became a grimace, "that's not too personal, is it?"

"Considering what happened last night, I think we are way past worrying about the delicacies of you giving me suggestions," I laughed, pulled her close and kissed her again, stopping only when the urges in my groin suggested following her suggestion might be becoming an issue.

"So, you would be open to more?"

I had turned away and slid my hand down my slacks, finding that what she described was actually easy and that, as she suggested, my panties held everything in place pretty well, "Depends on what you have in mind, except one time in college, I've never even considered leaving my house dressed and here I am going out with a beautiful woman while wearing girls clothes."

"Well, this beautiful woman likes it," the way she smiled at me was intoxicating, I didn't think there was anything she could ask me to do that I would say no to," have you ever worn a wig or makeup?"

"That one time in college, my girlfriend made me up like in drag for a costume party, it was actually a lot of fun."

"I was thinking more subtle than what most people consider drag, but if you're ok with it, "she left the question unasked and I agreed anyway. When she was done, the transformation was amazing, I was actually pretty, I would have tried to get in my pants, I laughed out loud at the thought.

"Can you teach me how to do that," I asked excitedly?

"I'd love to, maybe tomorrow we can go shopping and get you your own wig and makeup, maybe even some breast forms, if you'd like?"

I thought about telling her I already had a wig, but mine was a dead cat compared to the one she was letting me use, my new hair flowed down around my shoulders, framing my face perfectly, the blonde color matched mine but with subtle strawberry highlights, my eyeshadow made my blue eyes pop, the base and rouge she applied gave my face a decidedly feminine appearance, the pink lip stick was the absolutely perfect finishing touch. Carla gave me the tube and I dropped it in my purse.

"So, where is my new girlfriend taking me to dinner, "she put her hands on my shoulders and smiled at me in the mirror.