Summer to Remember

Bright pink lipstick and a pair of strappy sandals with four-inch block heels. Damn, I looked good. I smiled at the girl in the mirror, took a deep breath, grabbed my purse, and headed downstairs. They were both in jeans and casual shirts.

My first reaction was to run back upstairs as fast as I could and change.

"Claire would be proud of you." Steve just smiled at me with that same approving look he gave when I nailed a pose during the photo shoot. I knew I had done good. I just smiled and gave him a kiss on the cheek. Aunt Judy looked a little confused, and I understood why. This I couldn't pass off as an accident or autopilot. I had obviously chosen everything I was wearing.

"Les, are you sure about this?" Judy looked more apprehensive than concerned.

"I think so." I bit my lip and met her gaze with mine, took a deep breath, and let it out through pursed lips. "Let's just go before I change my mind."

It wasn't the going to dinner part that made this special. It was everything else that came with it. Sure, I enjoyed the food. The Italian place we went to was famous for its thin crust pizza and its pasta dishes.

It was simpler and far more complex; it was 'the going' that was important. Sure, there were entire ad campaigns being laid out, mailers, newspaper inserts, junk mail. It was all coming. The shoe company and its subsidiaries and alias companies were designing and laying out catalogues. They were developing websites, and all using my pictures, me, to sell women's clothes. In a few months, my face, my feet, my body would be all over the world, but those were just pictures.

So many questions... Was this me? Was this fiction or fantasy? Was it real?

I did this, but did I want this? Sure, I had seen the pictures. I had my own copies of so many of them. The girl in the pictures was beautiful, but again, she was fictional. I needed to know how the world would really see me. I needed to know if this was real - if this could be real.

Part of me was terrified. Another part had wanted this to be real from the first click of Steve's camera. The results only amplified both feelings.

The way people looked at me made me nervous. There was no disdain or malice. It was lust or envy. Our waiter openly flirted with me; tall and obviously fit, perpetually fighting to keep his shaggy blonde hair out of his face, those crystal blue eyes sparking at me. I blushed, I smiled, I did my best not to run out of the restaurant like my hair was on fire.

Did I get any answers? I don't know. If I did or didn't was irrelevant. Those strange fantasies were back, and this time, they had a face.

Steve stopped by Monday to tell me the client had delayed my shoots a week or two because he had to go out of town for personal reasons. It wasn't a problem because I'd decided I wanted to take a break from the whole dressing like a girl thing. He changed my mind when he gave me a bag with three new bikinis in it.

"Wear these when you lay out. They're Tan Through". The fewer tan lines we have for your next shoot, the better.

"Sure. Thanks." For the money I was making, I guess I could continue laying out by the pool in a bikini. Besides, these were cute and sexy. Fuck. My mind was betraying me.

I had at least two lawns every day all week, and while I could still go online and zone out in Los Santos or some other fantasy world, I quickly got bored.

Wednesday afternoon, I walked into Romano's asking for an application.

"Sure. We're looking for people. You have much experience?"

I laid out my summers and gave the names of the restaurants I worked at during school, going over the levels of service. The manager set my application aside without even looking at it. We talked about a few things, what it was like to be in the weeds, how I had handled one or two problem tables.

"I just take it one table at a time. It all averages out. Besides, I've historically made enough that a bad table here and there doesn't bother me."

"Can you start Friday? Black pants, black shoes, black long sleeve shirt. I'll have you follow Tony."

"Only thing is, I do lawns during the day and do some modeling, so I'll need you to work with me on schedule."

"No problem. We open at four-thirty every day. We're closed on Mondays. No lunches. Can you work with that? Probably three, maybe four nights a week. And always Friday and Saturday, though. You let me know if you need specific days off, and I'll do my best to accommodate."

What he was offering was pretty standard. I liked the no lunches. "I'll see you Friday at 4."

"Hi there. You leave something behind Sunday?"

"Um, no. Just applying for a job. I uh, start Friday. Going to follow someone named Tony."

"Well, that's good and bad. Good, that I'm Tony. Bad that you already forgot my name." He feigned being shot in the heart and grinned at me.

Shit, this was not good. You would think that at an Italian restaurant, a guy named Tony would have dark hair and brown eyes. Nope, this one was easily 6' 3", and obviously fit, perpetually fighting to keep his shaggy blonde hair out of his face, those crystal blue eyes sparkling at me. I blushed, I smiled, I did my best not to run out of the restaurant like my hair was on fire; again.

No makeup, no boobs. Of course, I had the hair and couldn't change my eyes, but I was wearing Dockers and a polo shirt. No bra underneath, so there were no straps. Yeah, I was wearing panties, but I discovered they were just more comfortable than my boxer briefs.

"So, which one of you is coming to work?"

"Excuse me?" My jaw literally dropped open.

"Well, Sunday, you were definitely a girl, and today, well... not so much. I could never forget those eyes." Damn, his smile was intoxicating.

"It doesn't bother you?"

"Why should it? You seem like a genuinely nice person, and to be honest, I'd absolutely date the girl I waited on Sunday. I don't care what's under the hood. I can deal with either."

My brain officially hurt. I don't know what my expression was, but I could feel my knees getting wobbly. He reached his hand out toward my face and gently closed my mouth for me.

"Listen, your secret is safe with me. I'll see you Friday."

"Um, uh, yeah. Friday. My application said male. I'm Les, by the way."

"Nice to meet you. Any chance you could put in a good word with, I guess it would be Leslie?"

I had to laugh. This was just too absurd. "Yeah, sure. I'll talk to her. See you Friday."

What the hell did I just get myself into?

I snagged a menu on the way out the door, figuring the more prepared I was when I got here on Friday, the better.

The mall was now a required stop on the way home. I picked up some black pants and shirts. I didn't think anyone would notice if the pants fit a little snug and didn't have back pockets, or that the shirts buttoned from the wrong side. Wearing the cute pumps I found would be problematic, but they were comfortable, and I liked they offered a choice of the strap behind my heel of across my arch. I had a pair of men's dress shoes I'd probably wear on Friday. I'd see about the pumps once I knew how I was going to be received by the rest of the staff and the customers.

The rest of the afternoon and Thursday afternoon, I spent wearing one of the skimpy bikinis Steve had given me, laying out by the pool and studying the menu. Working in Italian restaurants wasn't new to me, so picking this up should be easy.

I fit right in and made a good impression with the rest of the waiters, probably because I didn't have to be taught how to cut lemons or roll silverware. I just jumped in and started helping. Following Tony was fun. We worked well together and flirted almost too much. By the end of the night, I felt confident I could handle a section by myself. Saturday night, Tony got an enlarged section; the extra two tables would be mine.

It was a toss-up with my tables whether they would call me young man or miss, and I didn't worry about it. It was probably closer to 60-40 in favor of miss. I just smiled and answered to both. Why go into something like that, anyway? Let them think what they wanted. I just smiled and got them what they asked for and counted my tips at the end of the night.

I was the last to do my checkout with Angelo, and I had evidently impressed him. My wine sales were better than the other servers, and my check average was higher, too.

"You did well tonight. Better than most new servers. Tell me about your modeling schedule. I want to put you on for Wednesday through Saturday. Can you work around that?"

"It's not set. The last job I did was all week, ten-hour days. It was brutal. The photographer I work for says he already has two more jobs, but I don't know what they are. The best I can do is tell you as soon as he tells me."

And we had an agreement. Angelo liked his servers on set schedules as much as possible. There were a few that wanted variety, but most appreciated being able to plan things in advance. It was up to me to cover any shifts I couldn't make. If it was for modeling, he would help me out, but otherwise, well, I was one of the team now.

"One more question. What name do you want on your nametag, Les or Leslie?"

"Excuse me?" I'm sure the confused look on my face relayed the rest of the message.

"Look, I was watching you. Half your tables thought you were a girl. It's obvious to me you encourage that a little, maybe a lot, sometimes. Your nails, your blouse, earrings, hair. I don't care. It just needs to be consistent. You show up on time and do your job, and I'm good. So, Les or Leslie?"

So much for being subtle.

"Um, yeah. This photographer has me modeling women's clothes. It'd be too much trouble to get my hair and nails done every time he called me for a job, so I just leave them like this. I'd have to think about it."

"Girls make better tips, especially pretty ones." He smiled at me.

Why was my whole life conspiring to get me to dress like a girl? All I needed now was for one of my lawn jobs to offer me more if I showed up in a damned bikini.

Tony was obviously waiting for me when I came out of Angelo's office, since everyone else was gone.

"Everybody's across the street having a beer. You interested?" There was that smile again.

It was fun, server talk. We swapped war stories and laughed, shot a little pool, and had a great time. I was going to enjoy working at Romero's. The bartender called last call, and the lights in the bar came up. We were finishing our drinks when I caught Tony looking at me with that smile again.

"Hey guys." I figured, what the hell. I might as well get ahead of the curve. "Listen, I talked to Angelo about this already and he's OK. Um, I do some modeling. I know it's weird, but it's women's clothes. If none of you have an issue, I'm going to dress as a girl at work. Most of my tables tonight thought I was a girl anyway, and they tipped better than the others, so it's kind of financial."

"Kind of?" I didn't catch who said it.

"Yeah, and kind of not. I kind of like the way I look." I shrugged.

"Not a problem. Right guys?" Tony chimed in. Nobody else said anything. There were some interesting looks, confused or surprised. Surprised that I wasn't a girl. I guess my tables weren't the only ones.

I had just outed myself to a dozen people I had just met. What the hell? I was outing myself to everybody that came in the restaurant for the rest of the summer, and the rest of the world this fall when the catalogs dropped, so why not?

"Outing myself." I thought about those words as I stood under the shower when I got home, watching the water circle the drain and then disappear. Was that what was happening to me? Was I circling a drain? Could the 'me' I had known my entire life be slowly disappearing from existence, to be replaced by the pretty girl Steve and Claire had helped me discover?

I did like how I looked all dressed up. In fact, I love how I looked, but what did it mean? Was it just the clothes or was it more? Did I actually want to be a girl, and what would it mean if I did? Hormones, surgeries... girls date boys, well mostly, so could I do that? Tony had already told me he was interested. Maybe I could be a lesbian, but do girls even like guys like me, or girls like me?

My aunt didn't care. Steve, Claire, they both seemed to encourage it, and Angelo, well, he just wanted the higher sales that came with me being pretty. Everybody had their own agenda. I just needed to find mine.

I did the lawn on Sunday in a bikini Steve gave me. He had been emphatic about my tan, and, well; I like the way I looked. To make matters worse, that visual gratification I enjoyed was taking on a physical something. It was something visceral, something I couldn't explain. It had felt right.

When I finished the lawn, I went for a swim and laid out by the pool for a while, just like I always did. When I went back inside, I took another shower and got dressed. Nothing special, just shorts and a floral print cropped top, with my forms, bra, and panties underneath and light makeup. Even in the face of all the indecision, things were escalating.

Instead of playing video games, I started doing research on cross dressing and being transgender. I looked for anything I could find that related to what I thought I might be going through.

Judy saw what I was wearing and probably looked over my shoulder at what I was doing on the computer when she brought me a sandwich. She didn't say a word, she just pulled my hair back behind my ear and kissed me gently on the cheek. I knew she'd be there to talk to when I needed her. She always was.

There was one other person I could talk to. Betsy knew more about me than anybody. We had shared our darkest secrets for years. This was something that had never come up.

"Hey bestie." Betsy's bubbly voice made me smile. I always did.

"Hey. How was Cabo?" She and her family had gone to Cabo San Lucas for ten days right after school let out.

"Amazing!" She put extra emphasis on the 'zing.' "For once, I'll bet my tan is better than yours."

"Maybe. But I've got all summer to catch up."

"So, what's up?"

"Um, I got a different job this summer, and it's kind of gone a little sideways."

"How so? I mean, you can always move to a different restaurant, right?"

"It's not that. My aunt's next-door neighbor is a photographer. He does fashion shoots and stuff."

"So, you're helping him. That sounds cool and I'll bet his models are hot. You got any prospects?" My mind flashed to Tony. Not yet. Baby steps. This was going to be big, and I didn't want to freak her out too badly.

"It's not like that. Let me send you a couple of pictures." I scrolled through my phone, finding a few of my favorites, intentionally avoiding anything risqué. I hit send and waited.

"Les! Oh. My. God! Oh, my god, oh, my god, oh, my god. Is that really you? You look gorgeous. You look like a real girl. Tell me everything." So, I did. Starting with how we met, the portfolio shoot, and then the shoe catalogue. "He has two more shoots he wants me to do, maybe more. And it pays a lot better than waiting tables or doing lawns."

"That is so cool. My bestie is a supermodel." She laughed. "You said it was going sideways, though?"

I switched to FaceTime. "Bets, I can't stop. I'm going to work at this restaurant next week as a girl. My boss knows. All the other servers know. What am I going to do?"

She was quiet for a few seconds. I could see it in her face. She was thinking about what to say. "I like your makeup."

"That's it? That's all you have to say. I bare my soul and you like my makeup?"

"Well, I do. It brings out your eyes. Besides, I'm your best friend. It's my job to support you. You say you can't stop. So what? You make a beautiful girl, so be a beautiful girl. If you change your mind, stop, or don't. When you come back to school, we can get our nails done together, and stuff like that."

"You're really ok with this?"

"Les, I'm going to be completely honest with you. I love you. I do. But the reason I never dated you is because of how feminine you have always been. You know the type of guys I like. I'm honestly surprised this didn't happen sooner. If this is what you want, well, at least it makes picking a maid of honor easier if I ever get married." The bitch laughed. I was speechless.

I honestly didn't know what bothered me more, that I liked it, or that everyone that I cared about was ok with it. 'Surprised it hadn't happened sooner.' What?

All the horror stories I had been reading about all afternoon, all the rejection and abuse people like me had experienced, and all I had found was acceptance. My world was small compared to most people, but maybe it was some kind of sign or something.

I sent Betsy some more pictures, even me in that white bikini, and we talked some more.

"No cutting anything off until you're absolutely one-hundred percent certain. Promise me, ok?"

"I've gotten pretty good at hiding it, but I'm not getting anything cut off." We both laughed.

I felt better. Maybe it was just knowing that I wasn't losing my best friend. Maybe it was more. I was still nervous about what was to come as more and more people found out, but I knew I had Judy, and I knew I had Betsy. Then there was Tony and whatever that was.

A couple of lawns in the morning, swim, lay out by the pool. Video games for a few hours in the early afternoon, and Wednesday, I showed up at Romero's ready to work. My breast forms were obvious, but with the black shirt, my bra wasn't going to show through my shirt too much. Makeup spot on and I had gone to the salon to get my nails done bright red. My lipstick matched.

There was no Tony, but the setup was the same as Saturday. I had a small section next to one of the better servers. It was slower than Saturday, but that was to be expected. I still did well.

When I checked out, Angelo complimented me on how I looked and commented that two of the waiters had asked not to be scheduled with me. He told them it would mean losing their weekend shifts, and they changed their request to just not having a section next to mine. I guess there had been fallout after all. I now knew who they were and could do what I could to avoid them.

Thursday, I got a full section as I did on Friday and Saturday. I was making so much more than I had in my previous summers. Maybe I should have been working at better restaurants, or maybe it was because people like Leslie better than Les. It could have been anything. I certainly wasn't complaining.

The two guys that had complained made a minor scene at the bar Saturday night complaining about favoritism; my section was better than theirs and it was hurting their tips. They had been here longer and deserved the better sections.

"Pete, shut up. You're getting the same section you always get." A waitress named Jenn shot him down hard. "Your sales suck, you never sell wine. You don't upsell. She does all of that. You want a better section, make Angelo more money."

He and two other waiters got up and moved to another table. I was trying to ignore them, but couldn't help noticing they kept looking back at me every few minutes.

"I'll walk you to your car." Tony sat down next to me. "So, I guess you've decided. Have you given any thought to what we talked about? I've always fantasized about dating a model." His stupid smile was going to get me in trouble. I could just feel it.

"Tony, I don't know about that. I don't even know if I could date a guy."

"How about this? You've got a swimsuit, right?"

"Probably too many." I laughed.

"Me and some friends are going to the lake tomorrow. Come with us and just hang. We'll have some beer. There will be a ski boat. It will be fun, and we can get to know each other better."

I don't know why I said yes. Maybe it was because I honestly liked Tony. Maybe it was that damned smile, or maybe it was because he helped me change the tire on my car that someone had slashed.