I’ll admit it. I was nervous. It was my first time ever being dressed. No wait, that wasn’t right. It was the first time I’d be out in public dressed. The few evenings I spent with my elderly neighbors didn’t count, I think.

I was dressed as a nun covered from head to toe except for my face. My neighbors didn’t recognize me as I stood waiting for my Uber, impatient and nervous because he was three minutes late. They smiled and wished me a good night, wondering what a nun was doing in the neighborhood. A couple did a double take when they saw my face. I’d gotten pretty good at applying makeup and felt this was my best effort ever, the mascara and eyeliner did a good job of highlighting my big blue eyes and the lip gloss seemed to bring out the cupid’s bow in my mouth.

The name tag that came with the costume said ‘Sister Mary Elizabeth’ but it may as well said ‘Cliche’ because that’s how I felt. I was five feet five inches tall and the most I ever weighed in my life was 135, and I was at 120 now. No muscle mass at all. I was once described as willowy, a term I hated. The icing on the cake was my eyes, huge and vibrant blue. Couple that with a mouth any woman would kill for and an ass that put most genetic women to shame and you can imagine what my life had been like in high school and college.

I sighed as I felt the stockings rub my legs. Patterned, seamed hose that had belonged to my twin sister. She had died in a car accident, the victim of a drunk driver. The driver was her boyfriend. I was her sole living relative and beneficiary of her will. I inherited her clothes, jewelry, a surprisingly large savings account for a twenty-three year old, got fifty grand from the car insurance company and another hundred grand from a personal policy.

I socked it away thinking I’d like to buy a home somewhere down the line. Someplace away from here. I just didn’t fit in. I hated sports and wasn’t good at any of the ones I tried. Guys tended to ignore me after a while, those that didn’t try to bully me.

You could forget about women, I either got ignored, stuck in the friend zone, or worst of all, treated like one of the girls. What guy wants to hear about periods or the night their boyfriends took their ass for the first time? Or worse yet, saying they were sure I knew exactly what they were talking about, right?

As far as I knew I wasn’t gay although I’d look at a hunky guy as quick as I would a hot woman. I convinced myself I just liked a well porportioned human form.

I had no friends. I did have a good job even if I didn’t like the company I was with. They seemed to attract the ex-jock/cheerleader crowd who skated through school and got an unearned degree, then being slapped in the mouth by reality when they were expected to actual produce to earn their paycheck. I was the shining star, the one my manager held up to the others. That did nothing at all to enhance my popularity. It all came to a head when one of the old jocks just barely hanging on to his job by a thread cornered me in the bathroom. Before I could react he grabbed me, almost holding me off the floor by the throat.

“Here’s the deal, Mr. Hotshot. You’re going to do the Perkins file for me and do a damn good job. Do it or I’ll kick your little fag ass.” I agreed instantly, then made sure I put so many mistakes in it it looked like a joke. The manager called Asshole into the office, holding the papers.

“This your work?”

The guy preened thinking he was going to get praise, maybe even the line manager job that was rumored to be open soon. “You bet, Boss. Worked my ass off on it too. Lots of late nights on this baby but it was worth every hour.”

“You really think so?”

“Absolutely.”

The Boss sighed. “This is the biggest pile of shit I’ve ever seen Barker. It reads like it was written by an idiot. An idiot whose first language isn’t English. Were you drunk, or stoned, or are you really just an idiot? Or maybe you’re just plain stupid. This is the last straw. I want you out of the building in an hour. Don’t look for a reference. One hour, understand?”

He ranted, he raved, he blamed the whole thing on me. The cops had to come and escort him out. I grinned as he went by. He looked at me and knew. “You bastard! You did this deliberately! I’m gonna kick your ass.”

“For what? That was your work, not mine. At least that’s what you told everybody. Only an idoit wouldn’t proof read a report before turning it in. Good luck on your next job.”

He lunged at me, which got him escorted out in handcuffs. The whole office watched the perp walk. I declined to press charges and they let him go with a warning. If any harm fell to me in the near future regardless of who did it, they would be looking for him.

The Boss called me into the office and let me sit for awhile before speaking. “I got a feeling that if I dig deep enough I could come up with some examples of bad blood between you and Barker. I also have a hunch it wouldn’t do to fuck with you. If you can fix the Perkins deal you get the line manager job. I have to tell you it won’t be easy and most everyone is going to resent you getting it but I don’t want popularity. I want results. Think you can get it for me?”

I grinned and handed him the real work I’d done on the Perkins account. He gave me a tight smile and warned me. “This is the last time you pull anything like this, you understand? I’ll be watching you like a hawk. After all if you’d do something like that to a coworker even if he was a dickhead, nobody in the company would be safe. Good Luck.”

I saw the writing on the wall. They needed me badly right now, but as soon as they felt they could get along without me I’d be gone.

I sighed, looking at my watch. Or rather my sister’s watch. The isolation and lonliness I felt overwhelmed me sometimes and I’d go into the spare bedroom where I kept my sister’s stuff and lie on the bed and talk to her. It made me feel better. I got into wearing her clothes almost by accident, a case of not doing laundry until everything I had was either at the cleaners or in the laundry hamper.

I sorted everything out and realized I was going to have to wear dirty clothes to the laundromat. I was a bit obsessive about cleanliness, one of many traits that made it impossible to have a roommate. Then I remembered Annie’s clothes. I found a pair of skinny jeans I could fit into even if they were tight. I was about to go commando until I noticed a pair of yellow boyshort panties. Deciding nobody would ever know I shimmied into them, amazed at how good they felt on my ass. I threw on a purple tee, put my long hair up into a ponytail, and walked downstairs to the basement.

I had three washers going wanting to get done fast, and as soon as one finished I threw everything into a dryer. The first load was done so I dropped them on a table and started sorting. One of my elderly neighbors came in and I noticed she was having trouble so I helped her sort and load her machines. She patted my cheek and thanked me, telling me I was going to make a good wife someday. She thought I was a woman! I didn’t contradict her and she chattered as she worked, telling me to hold out for the perfect boy and not get carried away because my boyfriend might be good in bed.

“I remember it pretty well, child. Sex is wonderful but it won’t sustain a relationship. It doesn’t matter how good he is at ringing your chimes if he can’t support you and the kids or if he drinks too much or God forbid gets into drugs or even runs around on you. Go for the nice ones dear, and stay away from the bad boys. They’re good to play with but not good as life partners. I know from experience. My first was a thug. But my Walter, that man has a heart of gold and he lives for me and our children. And believe it or not he was a better lover. Thirty-nine years and he’s still smiles when he sees me.”

My laundry was finished but I stayed, chatting and helping. I even carried her stuff up to her apartment on the floor above mine. She insisted I come for tea and I told her I traveled a lot but if I was in town I’d call. She gave me a big hug as she thanked me.

I felt even lonlier when I got home. Where was my Walter? Wait, what? I wore the clothes until bedtime and slept in the panties. After that I experimented. Dresses, skirts and sweaters, frilly blouses. Then I got into trying the different styles of panties she had, then pantyhose, thigh highs, and stockings. Even her shoes fit me and I learned how to walk in heels. I remember the first time I wore pantyhose to the office, scared to death but so excited I couldn’t work. Then I tried her bras. Poor Annie was as flatchested as I was so many were padded. They became standard attire in the evenings. I couldn’t explain it if I had to but I felt ... safe ... free maybe ... in her clothes.

Did I worry about a friend popping by unexpectedly? No. I had no friends.

I talked to Annie a lot. We were identical twins and almost inseperable our whole lives. Mom noticed that we would get nervous and agitated if we were away from each other for extended periods and be almost manically happy when we saw each other.

I was her best friend and she was mine. We talked about everything. When puberty hit us we helped each other through it, not the least bit embarrassed to talk about the changes in our bodies. It was in that time period that Annie became really popular, her beauty making her stand out. She was getting hit on, sometimes by adults, from the age of fourteen. I got my ass kicked when I was fifteen when I heard a senior talking shit about her. Still managed to get some pretty good hits in and the jock caught hell for letting a five five nothing of a guy give him two black eyes. It was nothing to what Annie did to him when she found out why we fought. She jumped him in the cafeteria in front of all his jock and cheerleader friends.

She smiled at him and he was so happy he was smiled back.

His smile disappeared when she lashed out. “So you’d like to fuck me in front of all your friends? Make me do a gangbang when you got tired of me? Seriously, have you ever talked a girl into something like that before? Where would you find someone with so little self worth that she would agree to that?”

There was dead silence and one of the girls turned red and started sobbing. Annie just sighed. “You poor girl! Get up, you’re coming with us.”

She leaned over until she was inches from the jock’s face. “You’re a pathetic piece of shit, you know that right? I hear you’re dumb as a stump and the only way you’re passing is because the team needs you. Ever think about what’s gonna happen when high school ends? You may get lucky enough to get a ride from a cut rate college, but as soon as that’s over you’ll be on the street with no skills at all. Think an employer will be impressed that you scored the winning touchdown in the state championship five years ago? Fuck no he won’t. All he’s going to be worried about is can you the job he may hire you for. I predict a long and miserable life for you. I can see you now sitting in some dive bar when you’re in your forties with your beer gut hanging over the table, telling all the other losers you hang with tales about your glory days. I kind of feel sorry for you but mostly I feel you’re going to get what you deserve.”

His mouth was hanging open and she was pretty loud so most of the cafeteria heard what she said. “Back to the present. You ever talk junk about me again or hurt my brother, well, it wouldn’t do to walk in dark hallways for awhile. A baseball bat to the knee will end your glory days before they get started. You understand? It may not be me, it may not be my brother, BUT IT WILL HAPPEN! Never speak to me or about me again loser. You won’t like what happens if you do. We clear here?”

He was past red and I was pretty sure he’d never been talked to like that ever. Better get used to it was my thought. He tried to stand up but his buddies held him down. He went into a rant but stopped when he felt a hand on his shoulder. It was the assistant principal.

“I heard most of what was said. I suggest you follow the young ladie’s advice and stop while you’re losing. If you do we’ll consider the situation resolved. If not, well, you’re already on shaky ground academically. One slip and you lose you eligibility and will have to sit out the next few games until your grades come up. Clear enough? And Mr. Williams, I would be very disappointed to hear you’ve treated any of these young ladies with any kind of disrespect in the future. Very. Continue your lunch.”

He turned to Annie trying not to grin. “You, young lady, need to watch how you verbalize while on school property.”

“Yes sir. It will never happen again.”

Annie pretty much destroyed his confidence and it showed on the football field. By the end of the season he was riding the bench and never went to college. The last I heard he was working for an oil change business.

Annie befriended the girl and they became close. When she was a Junior Beth talked her into trying cheerleading, and she was such a natural she got a cheerleading scholarship from a major school. She tried to get them to give me a ride but I had already been accepted an academic scholarship to an Ivy League school, one of the less famous ones known for their ability to turn out successful businessmen. We texted constantly and spent every vacation and holiday together.

Beth gave me a graduation gift and took my virginity. I found it unsatisfying emotionally, and I could tell she was less than impressed with my performance. She hooked up with me twice more before giving up and giving me some advice before I left for college.

“Man up, Kevin. I felt like the guy in the relationship. Be a little assertive once in a while, girls appreciate that more than you realize. Otherwise you’re going to end up a submissive little thing and your favorite words will be ‘Yes, Dear.’ Good luck with school.”

It was four years of misery. I didn’t date once, didn’t get hit on, at least by girls. A few of the gay guys did and one basically stalked me. He was big, blunt, and arrogant. He reminded me a lot of my high school bully. He even told me he was going to break me in right and I’d be his bitch for as long as he was there. I kicked him in the nuts. Hard. He never approached me again.

I wanted to hate her boyfriend but he seemed nice and really loved Annie. They went to one party too many that Christmas, ran a red light and got creamed by a big SUV. I still miss her.

My coworkers deeply resented the way I handled their friend and it galled them no end to have to report to me. It took me firing two to bring them to their senses. Upper management took a hands off approach, waiting for the situation to get out of hand so they could fire me.

Then a month ago there was a thaw. One of the cheerleaders types sat with me at lunch one day. “Look, Bobby kind of deserved what you did to him but you could have handled it differently. You treat us fairly, you even help us when we need it and we’ve all gotten a raise we know you’re responsible for. You’re a pretty decent boss and I’ve been appointed to bridge the gap. Just so you know the animosity ends today. If we have something to say we’ll say it to your face. Doesn’t mean you’re our new best friend but it does mean we’ll treat you with a little more warmth and respect.”

Of course, I suspected everything. But they did try to be nicer and I even went out to drinks with them one night after work. I was having a decent time until I glanced in the mirror, seeing the exchange of smirks between Melissa and John. When I turned their faces were bland and friendly.

The next week Melissa came up to me. “The guys and girls are going to a party the Saturday before Halloween. It’s a big deal and supposed to be a blast. We’d really like for you to come. One thing though, the theme will be guys have to dress as girls and the girls have to dress as guys. I’ve already got my costume. A zoot suit and big fedora. I’m even going to get a fake mustache. They’re giving prizes to the ones that look the most convincing. With your size and body shape you could win, especially if you play up those gorgeous eyes. Think about it.”

They played up the party for weeks. Josh bragged he was going to go as a sexy librarian, said he had a wig he was going to put up in a bun and some catseye glasses to finsih off the look. Dale grinned. “I’m going as a hooker. Ordered a set of 44Ds and the skirt will be very high. I even got fishnets and a garter belt. It’s amazing what you can get off the internet these days.”

They talked it to death and the smirks got bigger as the time went by. They nagged me and one day something in my head said “Fuck it. They want crossdressed, I’ll give them crossdressed”, so I told them I would go. They pestered me for days about my costume and I’d just smile and tell them they’d just have to wait.

I agonized for a few days over what to wear. I got a few of Annie’s club dresses out and tried them on. They made me look hot but I wasn’t really comfortable in them. Then I found the nun costume and smiled, remembering when she wore it. She looked demure until you noticed the over the top makeup. “How do I look?”