Amy's Coming Out Party

"What are you going to be for my Halloween party?"

A simple question, really, but one I had been avoiding.

My friend and co-worker, Jackie stared at me as she waited for the answer.

"You know, when I was a kid, I loved dressing up for Halloween. Free candy and all that. Now. I am a 35-year-old man. Who wants to see me dressed up as Superman or Batman. No one that's who."

"Come on, Robert. I don't host parties very often. And you know I love Halloween. This will give you a chance to meet some of my friends. And I certainly agree that you won't fool anyone dressed as Superman."

She was right about that. I had never been what you call a he-man. 5-5 and 130 pounds were not a super hero's ideal measurements.

"You could go as Napoleon or a Munchkin from Oz! Or Mini-me, or a Minion. Oh, I know; the guy who said 'the plane, the plane' on the old TV show."

I have always been sensitive about my height. My entire body, really. Jackie always knew when she could push my buttons and when I was not in the mood.

"All right, all right, enough of the short jokes," I said with a bit of a laugh in my voice .

"The thing that's wrong with Halloween is that all the best costumes are sexy outfits for the women. There's only munchkin costumes for guys like me."

Jackie appeared to have an "Eureka" moment.

"Meet me at my apartment at about seven tonight. We can get a pizza and I'll have some costume ideas for you."

Yikes. There went my excuse for missing the party. There was no telling what this girl would come up with. At her last Halloween party she talked another male coworker into going as a penis. To make sure everyone knew they were together she dressed as a very pink, very hairy vagina. I could hardly wait until I saw what she had in mind for me at this party.

I hoped that she had gotten rid of that costume. At least I was too short to wear the penis suit.

********************

I grew up in a home with just my mother and two older half sisters. It was the four of us plus a steady stream of 'visitors' to my mothers bedroom. Later my sisters did their share of after school entertaining. There was a constant stream of different men in our house.

I attended a small country school that was rich in athletic accomplishments. I was no athlete. My sole contribution to the school's athletic tradition was helping the cheerleaders come up with snappy slogans for the signs they hung up at the football field on game day.

"Pluck the Eagles" and "Shave the Beavers" were both mine. I spent a lot of time in the principal's office during my high school years

I was considered a 'brain.' If this little school had had a chess club, I would have been its president. I didn't belong there and the jocks knew it. I was constantly bullied.

I was not only short, I was not manly in any aspect. I had a soft voice that came in handy when I sang in the choir, However, it did not project masculinity. I had soft features and very little body hair. This was even more reason not to do sports; I would never survive the post game showers.

I know that people thought I was gay, but I did like girls, and later, women. Trouble was getting them. I had no chance at the best looking ones. The jocks had them all locked up. But even the not-quite-so-good-looking ones felt they could do better than me. That left me with the girls described as having a 'good personality.' Even so, they always seemed to want to be 'just friends. I was okay with that.

Did I have a curiosity about being with a man sexually? Not abnormally so. I mean, I do not know how other men feel about that. Or if I were more or less inclined that way than the average male. Like everyone else I do watch porn. And if I see a fine male specimen, I do appreciate his masculinity. Doesn't everyone?

********************

I live in the same apartment complex as Jackie, so getting there early was not a problem.

Jackie answered the door quickly, as if she was anxious to see me. This was not her usual 2-3 minutes to answer. She must have thought I was the pizza guy. When the pizza did get there, we ate in silence. When we finished, she went to her bedroom.

She returned carrying two very small costumes. As I looked closer one was a short, lacy, black French maid uniform. I assumed the other to be some sort of cat woman suit. She held them up.

"Which one do you like?"

"I think you would look hot in either. Much better than the famous pink number you wore."

"Shut up! That pussy suit was the talk or the party,"

"It was talked about all right."

"Regardless of that, these are your halloween costumes!"

"What? Oh no, I am not wearing either of those. Get serious." I gave her my best scowl.

"I am serious. You were complaining that there were no fun costumes for men."

She had a point there. I had never thought to dress as a woman.

"I am not wearing those."

Jackie was not slowed by my denial. "I guessed you would say that. Come on back to my bedroom and let's see what we can find!"

"I thought I would never get invited back there." We had always joked about taking our friendship to another level, but it would never happen

"Easy there, stud. You aren't getting me that easily," she said,

"I can dream"

"Well, here we are." Jackie said.

It was a pretty standard bedroom. It had the same layout as my bedroom only nicely decorated and neat. Very inviting.

"What am I supposed to see?"

"My closet," Jackie all but squealed. "If you don't want to be Cat Woman, then we will make it just a woman!"

"I said no."

"What you said was you were not going to wear either of those two costumes. Let me make you up for this party and you can go back to your 'masculine' life. We are about the same size so my clothes should fit you. Come on, be a sport! I'm betting you have at least thought about dressing in women's clothing."

I was a bit taken aback by her suggestion but was also intrigued.

While I have never actually dressed as a woman I always thought that their clothing was sexy. Growing up with two sisters and my mother gave me ample opportunity but I never tried on any of their stuff. All right, I will admit to trying on their panties. Ok, and their high heels. I almost got caught. End of story. Now I would have a chance to do it without the guilt.

'"Okay," I mumbled. "Let's get it over with. What do you want me to do?"

"Saying yes is all I needed." She pulled a tape measure out of a night stand drawer.

"I just need some measurements and I'll do all the rest. You just show up next Friday at seven. I'll have everything prepared then."

"OK I'll be here. I won't even ask why you have a measuring tape by your bed."

"Never mind that! Now I want you to take off your clothes so I can get accurate measurements."

"But...."

"But nothing. Just it down to your underwear. Tightie Whiteys I'm guessing."

I complied with her request. She was thorough with her measuring tape. Jackie was really getting into this "dressing Robert up" scenario. I would not find out until the following Friday just how into it she was.

********************

I will have to admit over the next few days that I found myself thinking more and more about what Jackie had in store for me. I had tried to get details from her a couple of times at work, but she was tight lipped. I still got the feeling she was more excited about it than I was .

Every time I thought about it I did get a little more excited. Not so much sexually as it was as a novelty. I looked at it as finally having a cool Halloween costume. At least I tried not to read any more into it than that.

This time as I approached Jackie's apartment at the appointed hour she was waiting outside.

"You're a bit eager aren't you?" Jackie looked a bit embarrassed. I could not figure out why this is so important to her. After all, I was the one getting dressed like I was a Barbie doll.

"I've already spent $200 on your little costume and accessories. So you're darn right I'm eager."

"$200! Why are you going so overboard just to dress me up?"

"Call it my gift to you."

"$200 could've gotten me a much better gift." I could think of many ways that I could make better use of $200.

Jackie ignored me. "Lets go inside, I'm ready to meet Amy!"

`"Amy?"

"You, silly. Once I get you dolled up, I can't introduce you as "Robert" that way now can I? I had to come up with a girl name for you. I hope you like it."

"Whatever."

Inside she once again took me to the bedroom. There on the bed were several dresses as well as bras and panties. There were a couple pairs of shoes. One pair had relatively short heels, but the other had very tall, slender heels — classic stilettos. I hoped she hadn't planned on me wearing them. I remember back to almost breaking an ankle in my mother's heels.

"First things first. Take your clothes off, all of them this time. I need you to get in the shower and shave your legs, armpits and anything else that might show. Shave around your weenie while you're at it. From what I saw last time, this should not take long. I will help you if you can't reach a spot. Just let me know."

She certainly had prepared for this. She had three types of razors as well as different creams and lotions. I wasn't sure about my back since I wasn't sure if it would show so I called Jackie. She answered by opening the shower door and stepping in — totally nude! She was close to my height and build, but all similarities ended there. All the years that I spent studying her body through her clothes did not prepare me for the real thing. Her ass was perfect, her breasts were perky B cups and her pussy was shaved. She was magnificent. I could not take my eyes off her.

"All right, pop your eyes back in their sockets. I'm only naked to help you out."

True to her word, she finished shaving me. I would need to shave again before the party, but for now I was very smooth. Jackie wanted me prepared for our dress up game.

We stayed naked as we returned to the bedroom. We started out with the bras. Obviously I didn't have breasts but Jackie had that covered. She had bought padded inserts that helped the bras fit better. We picked through her bra collection. She suggested a black lacy one that was very sexy. She had me try on 6-7 pairs of panties before picking the ones that matched the bra. I think she was enjoying watching me pulling the panties on and off over my persistent hard-on. To tell the truth I was enjoying it too.

I only tried on three dresses before settling on a black dress with a high neckline that would help cover my lack of cleavage and my Adam's Apple. It was a little short for my comfort, coming up a little over halfway up my thighs. Still it clung very nicely to my body. It was tight in just the right places. I have to admit I looked damned good in it.

A pair of black stockings and the stiletto heels I had seen earlier completed my basic outfit. Looking at myself in a full length mirror pleased me. Even without make-up and a wig the costume was taking shape.

After that I got dressed in my own clothes. Jackie, still naked, walked me to the door. She handed me a piece of paper with several businesses written on it. Each business had a person's name beside it.

"I will be busy next week getting ready for the party. The day of the party I want you to go by these businesses and ask for these people. They will help with your preparation for the party. Don't worry about the cost it's all been taken care of."

"OK," was all I had a chances to say before she hurried me out the door with my outfit in a large shopping bag.

**********************

The next few days until the party were interesting to say the least. I tried on the outfit every day after work just for 'practice'. At least that was my excuse. One day I even wore the panties and stockings under my work clothes. I was on the brink of orgasm the whole day. I was beginning to like this 'costume.'

I loved the heels. Not only did they give me a little more height but they made my legs look great. I practiced wearing them around the apartment so much I was afraid of ruining them before the party.

I got up early on the morning of the party, showered and shaved my exposed areas. That didn't take long as my hair had not grown much since the shave that naked Jackie had given me.

The places I was to visit were a day spa for a massage, a nail place for a manicure and a pedicure followed by a hair salon to get a wig attached and styled. I probably looked silly but it was halloween.

Finally only one place remained. It was an apartment in my complex! The note said to bring my entire costume with me.

I rang the bell not knowing quite what to expect. I soon found out. A heavyset lady (?) with a thickly made up face answered the door.

"You must be Amy!"

"No, I'm Ro.....yes you are right, I'm Amy. Jackie sent me."

"She never told me you were such a natural. Your face is so is so smooth. It is like a fresh canvas for me. Lets get started."

The lady, who went by "Frida" took me to her bathroom. She had a make-up parlor ready for me. She went to work crafting my 'look.' She would not let me look in a mirror until she was done. She instructed to me put on the outfit. She chose some black and red bracelets and a small clutch to accessorize my dress and my bright red fingernails. It was time to check that mirror.

I looked fantastic! I was a thirty-ish, well dressed, sexy woman! My wig was a light brunette that reminded me of Jennifer Aniston during her "Friends" days. My make-up, courtesy of Frida, was very complimentary . Mascara, eye shadow, foundation, blush were tastefully done. I especially liked how the red lipstick complimented my nails. My legs looked sexy in the stockings and high heels. Frida had done away with the bra inserts and provided natural silicon breasts that glued directly to my chest. They had a more natural look.

I was the type of woman that I would have no chance with. For the first time since Jackie had suggested it, I felt comfortable dressed this way. After some last minute coaching from Frida on how to walk and talk, I was ready for the party.

"Go get them, Amy"

Who exactly was I supposed to get?

As I turned toward Frlda, she reached up and pulled her wig off.

"You may as well call me by my real name, . Everyone close to me does. I'm Fritz."

"OK Fritz, you know my name is Robert.

"Oh yes, but it is Amy — at least for tonight. If you ever need help with your make up again let me know. Jackie always knows how to get in touch with me."

"Why...what," I started to mumble as I made my way out the door. If I needed help with make-up again?

**********************

I dropped off my male clothes at my apartment and walked over to Jackie's. She had opted for the cat suit. I could see by the look on her face that that she was impressed with her creation.

"Amy, come here." Jackie gave me a hug. As she did, she whispered in my ear, "Play along. You are an old old college roommate."

"Jackie Jackie, Its been a long time, Sweetie,"I said in my best womanly voice. I had practiced the voice almost as much as I had walking in high heels. I hoped I was doing a passable job on both. If not. I was just a guy dressed for Halloween, right?

Jackie quickly left me on my own after announcing me as her old roomy. There were not too many people there since this was a smallish apartment. There were the usual cheesy adult halloween get-ups. A cowboy and saloon girl, Batman, and a nicely done zombie. For once I was hot and not some troll standing in the corner.

I was glad Jackie did not invite anyone else from work. Actually that wasn't entirely true. Part of me wanted to test "Amy's" identity.

I mingled for awhile, drinking a couple of glasses of wine as I went along. I was about to get glass number three when I was handed one by a guy. I was taken by surprise since I had never been given a drink by a guy before. I managed to accept it graciously . I had noticed him earlier but hadn't talked to him yet. His costume was a set of surgical scrubs and stethoscope.

"Amy is it? Or is it Aaron, or maybe Michael or....?"

"Robert. Am I that obvious?"

"Absolutely not! I consider myself a bit of an expert at spotting cross dressers, transexuals and every differently gendered group there is."

"I must have been easy for an expert such as yourself, Mr...or Dr...?"

"Dr. Jones is good enough for now. And no it was not easy in your case. You are very close to being passable in appearance. By the way, I could tell that Fritz, Frida that is, did your make-up — a true artist. However, you had a couple of minor high heel missteps that gave you away. A woman of your beauty is usually vain enough wear heels so often that she rarely has even the smallest stumble. That plus fact that you have absolutely no idea how to hold a wine glass by the stem with those fake fingernails. I also know that Jackie had no roommates in college so there would be no reason to announce you as such.

"I see, Dr. Jones. Or is it Sherlock Holmes. And what is your expertise based on? Are you a Sociology professor."

"No, no, Miss Amy. Lets just say I have a life-long interest in the subject and leave it at that.

"I suppose I should be flattered"

"You should be. But I have to ask how long have you been cross dressing? As good as you are at it, you must have been doing it for awhile now."

"Less than a week."

"That's unbelievable. I would have guessed closer to a year. You are very close to being undetectable. You are quite the natural."

"I practiced a lot for tonight."

"A few more sessions with Fritz will do you some good in that regard."

"I'm sure. How are you acquainted with Fritz, er, Frida?

"Another life long interest I'm afraid. And before you ask, no I have never cross-dressed. I am just attracted to them. Another life long..."

"Interest, yeah I get it."

Although the good doctor was certainly enigmatic, he was also starting to appeal to me. That may have partly been attributable to the fact that I was standing there dressed as a woman. But l did not think so. That scared me.

After another glass of wine, I was definitely attracted. I made an excuse and said my goodbyes to Dr Jones before the wine made me do something I would regret. I was always a light weight when it came to alcohol.

"Very well, then Amy. Don't deny your nature."

I walked off with his words ringing in my ears.

I mingled a bit more, eventually talking to to a male friend of Jackie. He apparently did not even question if I were truly a female. He went as far to try to steal a kiss. I might have let him if not for the unwavering stare of the mysterious Dr. Jones. I went over to confront him.

"Was that what you were waiting to see? A man making a pass at me?"

"No, this is what I wanted." Dr. Jones pulled me to him and kissed me long and deeply. After a second or two of surprise, I found myself kissing him in return. His mouth had a slight taste of mint. I was kissing a man! And enjoying it. Once I started, I couldn't seem to bring myself to stop. It was as if an emotional dam had broken, spilling repressed aspects of my life. I was vaguely aware of the scene we were creating. We stopped kissing for a bit.

"We should get a room," said Dr. Jones.

"I already have one. Next building over. I should let Jackie know."

"I don't think she will mind. She pulled a young man into her bedroom earlier. What appeared to be a cat suit turned out to be a cougar suit."

With that, we made our way to my apartment. What was normally a two minute walk took us almost thirty as we stopped to kiss several times. I could not get enough of this arrogant man's tongue in my mouth. I even allowed his hands on my ass as he moved the hem of my dress up nearly to my waist. I should have felt awkward standing there that exposed for any of my neighbors to see but I didn't feel odd. I felt incredibly turned on. And I had a feeling my neighbors would be getting used to seeing me with men.