Little Men, Big Women

Sometimes it takes a deep look within ourselves to allow us to learn the most important of lessons.

Little Men, Big Women
edited by Sephrena Miller

“God I hate this program,” I stated.

“It’s just Jerry Springer,” my wife responded.

“But they’re all freaks. Everyday it’s the same thing, girl beats up girl, or girl beats up boy. Of course they do change the script every now and then, so boy beats up boy, or beats up girl, how can you watch this shit?”

“Come on Bill, it’s fun.”

“It’s not fun, it’s sick. I wish we had another TV so at least I could watch something educational, like Ultimate Fighting,” I laughed.

“I don’t know how you can watch the stuff, it’s so violent.”

“And?” I asked, pointing at the TV and the violence taking place between two girls.

“This is different. We all know it’s all in fun, and it’s probably fake anyway.”

“It looks real,” I said, as the wig came flying off one of the girls.

“See,” she giggled. “This is a fight between a woman and a man who thinks he’s a woman, and guess who’s winning?”

“The freak?”

“No, the woman, and where did the accepting man I married go?”

“What do you mean by that? I don’t have a problem with different people, but that crap is over the top.”

“Bill, it’s just a TV program, lighten up a little.”

“I know it is, but why can’t they have regular people instead of the fat women and men with half their teeth missing?”

“It wouldn’t be any fun if it weren’t for those goofballs,” Tina giggled.

I shook my head and started to leave the room.

“Oh wait, I almost forgot, it’s Halloween next week and we have to start getting ready for our annual party,” Tina announced.

“Is it that time already? What treat do we have for a theme this year?” I asked.

Tina didn’t miss the sarcasm in my voice.

“This year’s a little different Bill, we get to wear regular clothes, no more itching fits like last year,” Tina giggled.

“Last year wasn’t funny, I had hives for a week,” I responded.

Last year? Oh that was a treat! Wait, I guess I’m getting ahead of myself, so let me explain.


I’m Bill Windom, and my wife is Tina. I work for a computer company in Woodland Hills as a programmer, and Tina works for an advertising agency in Sherman Oaks and is a vice president of something. It changes from week to week. Any way every year they have a costume party with a theme revolving around something of interest to one of their newest clients. Tina has worked for them for six years and every year we went to the party.

Her firm goes all out and the costumes are expected to be above average. They cannot under any circumstances, mock the clients.

The first year we went as sport figures, me as a football player, and Tina was an Olympic swimmer. We pulled it off pretty well, especially Tina. Tina has an athletic figure and was asked if she swam in college. I however didn’t fare as well. I did swim in college so my thin frame didn’t lend too well to the costume I was wearing, but it did get a few laughs.

The next year was food supplier time and we went as kitchen workers, chefs to be exact. We both had on the high white hats, white shirts, aprons, and the works. You have no idea of how many invites we had to parties; only they expected us to cook.

Year three was movie heartthrobs. Tina went as Angelina Jolie and I went as Clark Gable. I think that was the most fun of all the parties. I became Rhett Butler and Tina was Laura Croft. Tina was in one of her crazy moods and personally customized our nametags. Hers read Angelina, and she added, ‘sorry about the lips’. Tina doesn’t have Angelina lips, nor does she have her figure, or eyes, but she is a lot more fun than Angelina could ever be. To my tag she added, ‘ sorry about everything, but personally my dear I don’t give a damn’.

The fourth year was kind of a mish-mosh of nothing. I went as a car mechanic and Tina was a sexy secretary. It was pretty boring.

Last year was pure Hell. Their latest client was one of those save the earth groups. Tina has always been one to love people like that. She always has some crusade going on at any given moment. Save Tibet, Save Darfur, there’s always something to save. This group wanted to save every living thing on earth, except us. Well Tina thought her every wish had come true with this party. She decided we should save the sea otters.

We spent the month before having sea otter costumes made. They even used real imitation sea otter fur, complete with fake ocean smells. I felt like I was a furry kelp bed when I wore that costume. One thing we hadn’t counted on was that I was allergic to the smell. The evening started well but as it progressed I started to itch. Just a little at first, but after an hour, I started to swell with hives. I felt as though my skin was on fire and I had to remove the head to breath. Tina saw my face and she let out a gasp.

“Oh my God, Bill, what happened to your face?” she asked, obviously concerned.

“I don’t know. I itch like hell.”

“Your face is swollen. Did you eat something?”

“No, not yet. I haven’t even had anything to drink.”

“We’d better get you to the hospital, I’ll call a cab.”

Needless to say the hospital staff had a great laugh as two giant sea otters entered the emergency room. I was given some injections and was asked to remove my otter suit. The swelling went down and I was released to go home. I had to don my otter suit once more for the taxi ride home, but it came off the minute I walked through the door. Never again I told Tina, no more fur, ever, which brings us back to this year.


“This year will be fun, but a little different,” she said.

“Please don’t tell me you signed NASA to a contract,” I moaned. The thought of wearing a spacesuit all evening wasn’t my idea of fun.

“No silly, we haven’t signed anyone for a while, so we put our client list in a hat and Sally picked a piece of paper with one of our clients on it. She chose Transformation Boutique.”

“And what is Transformation Boutique?”

“It’s a company that specializes in making men into women.”

I could see where this was going, and I was sure as heck not going to get my thing cut off.

“Hold on Tina, last year was bad enough, but I don’t want to become a woman. I like standing to take a pee.”

“You silly goose. They don’t really make you into a woman, they just make you look like one.”

“What about you, what are you going to wear?”

“Men’s cloths. You see the theme is to reverse our sex roles. I’ll be the man, and you’ll be my wife,” she giggled.

“That’s ridiculous. You’ll look like one of those men on Springer, except with teeth, and I can’t even imagine how bad I’ll look.” I said.

“Honey, the whole office is going to do it, even Justin Weeks.”

“Justin’s going to do it?”

“He said it was going to be fun.”

Let me explain that Justin weighs 325 pounds and it’s on his five foot five frame.

“He’s sick. I can’t see where that will be fun.”

“Of course it will be. Can’t you just imagine a hunky guy like me trying to seduce a foxy girl like you?” Tina giggled.

“Good grief woman, you can seduce me now, and I won’t have to be wearing makeup,” I hinted.

Tina stood, all five-three of her and puffed her chest.

“Come here wench, we have business to take care of,” she giggled.

Needless to say the parties discussion was dropped and we were soon asleep in each other’s arms.

Morning came and Tina wasn’t going to let the previous nights fun keep her from her mission.

“Bill, seriously, we have to start on the costumes for the party.”

“I know, but how hard do we have to try?”

“Hard enough that you don’t look like a clown.”

“I might not look like a clown, but I’ll sure as heck look like a guy in a dress.”

“Don’t be so sure, Mr. Macho. You haven’t gained a pound since college, stick man. Actually you might turn out pretty good. You haven’t worked out for years, and muscle does turn to fat. You may be thin, but you’re not fit.”

“Which means?”

“It means that you have a shape that can be molded into that gorgeous woman you’ve always wanted to be,” Tina giggled.

“God, I’m joining a gym so no one will mistake me for a woman.”

“Not until after the party. This will be fun, Bill, but only if you make it that way.”

I knew I wouldn’t be wining this discussion so I relented.

“Okay Tina, I’ll try. Let me know what I have to do.”

“I will sweetheart, and this way you’ll have a better understanding of what I have to go through everyday to keep you interested in me.”

“I don’t have to understand baby. As long as you keep looking hot. I thank my lucky stars everyday,” I said as I twitched my eyebrows.

“You goofball. Give me a kiss or I’ll be late for work.”

I kissed Tina goodbye and went to get ready for work myself. I had this nagging feeling in my gut that this years party was going to be the worse ever.


I met with Carl Bloom in the coffee room at break time.

“So you have to go as a chick to the party?” he asked.

“Yeah, can you believe what a lame idea that is?”

“Oh I don’t know, you’ll probably be hot in an ugly sort of way,” he laughed.

“Fuck you Carl. Hey maybe something good can come from this?”

“Like what? Getting to feel yourself up?”

“Dude, you’re a perve. No, I’ll be able to get into one of those Lesbian nightclubs and score,” I laughed.

“And Tina will make sure that you’ll be a real lesbian too when she cuts off your balls.”

“Ouch, you do have a point, and beside I would never cheat on her.”

“You’d better not, or I’ll be knocking at your door.”

Did I mention Carl has always had a crush on Tina?

“Your wife would kill you if you did.”

“It would be worth it.”

“Death for sex, I doubt it. I am a little worried though about what might happen if I look femmy around here.”

“Do you seriously think anyone’s going to give a shit?”

“Uh, I guess not. It’s not like I’m going to be hitting on anyone, well maybe Trisha, but none of the guys,” I laughed.

“Shit, if I could get into Trisha’s pants, I’d buy half the mascara in LA.”

“Carl, Trisha could care less about makeup, unless it’s on her. The only reason you don’t hit on her is that Mel has exclusive rights to her. Touch her and you’ll be out the door. Being a boss has its privilege.

“Point well taken. Let me know how all this girly stuff goes, I have to get back to that project I’m working on.”

“I will, and don’t laugh.”

“Would I laugh at my best friend making a fool of himself? Not a chance! Yuk!Yuk!”


I arrived home and found Tina was already waiting for me, which is unusual. She always left first in the morning and arrived last at night. Brainstorming at the agency lasted for hours, which made me glad to be at the mundane job I had.

“Hi, honey,” I said as I entered the door.

“Hi sweetheart. Guess what? I went shopping for you,” she said proudly.

“I just bought some new jeans last weekend,” I responded.

“No silly, for the party.”

I had buried that thought as deeply as I could in the deepest recesses of my brain, but the love of my life wasn’t going to let it rest there for long.

“Why did you buy anything? Can’t I just borrow your stuff?”

“You’re kidding me, right? Bill, you and I are different sizes. You’re five-eight and a woman your height wears larger clothes, and I might add, you have no figure, until now,” she stated as she held up a waist cincher and something with pads that I knew was going to make my butt look larger.

“Where did you get that stuff?”

“I called Rita. Her sister works for Universal in makeup, so we have a leg up on this. She told me what to buy for starters so we could get measurements on your hot little body. After that all I have to do is call her with your sizes and she’ll do the rest. To quote you, ‘it’s a slam-dunk,” Tina giggled.

“Do I really have to wear all this stuff?”

“Honey, this is nothing. Just wait until the party. You’ll wear more and it will look like less, I can’t explain it, you’ll see. Now take off everything you have on so we can get started. Oh I almost forgot, here are your panties.”

Tina handed me a lacy bit of cloth, which I jumped back from. Panties like this felt good on Tina, but I had never held anything like that in my hand without them being on living flesh.

“Come on Bill, they don’t bite.”

“But, but.”

“No buts, just put them on, or the girdle will chafe your pajama python,” she giggled.

“I’ll wear my shorts.”

“No you won’t. You know the rules, either we do it right, or not at all.”

“Okay,” I grumbled, as I took the way too sexy cloth in my hand.

I removed all my clothes and slid the panties up my legs and tried to nestle my now excited penis in the fabric. Tine watched and couldn’t contain herself. She started giggling. I on the hand felt my cheeks turning red.

“Something you like little girl?” Tina asked, with a smirk.

“This is ridiculous Tina. How am I supposed to hide this, and its not right for me to get excited,” I complained.

“All of us girls enjoy sexy lingerie like this, sweetie. Don’t be embarrassed. Just be glad you have a wife that can take care of situations like this.”

Tina took me in her arms and felt my butt, well the panties that were around my butt.

“Mmm, now I know why you guys do this to us, you feel, umm, wonderful,” she said as she led me to the bedroom.


Fifteen minutes later it was back to the item at hand, namely me becoming a woman.

I slid my panties back up my legs and tucked the now flaccid thing between my legs. Next came the girdle. Tina hooked the waist cincher behind my back and pulled a tape measure from her sewing kit. She measured around my butt, then my waist and finally around my chest.

“My, my, aren’t we the hot little thing?” she laughed.

What do you mean by that?” I asked.

“Well your hips measure thirty-seven inches, with padding. Your waist is only twenty-eight inches and your chest is thirty-eight inches. You’re almost a ten and ten.”

“A what?”

“A ten and ten. You know ten inches bigger than your waist, the perfect figure. I’m jealous. The best I can do is eight inches, and that’s at my hips, you bitch,” Tina giggled.

I shook my head. This whole thing was getting stupid as far as I was concerned.

“Can I take this stuff off now?”

“Are you sure you want to? Remember what your panties did.”

“I’m sure. I certainly don’t need panties to make love to my wife.”

“Mmm, but it was so much fun.”

“What happened to that sweet innocent girl I married just six years ago?”

“She went to the same place that accepting man I married. I guess we’ve become two sex starved alienated bigots. It’s getting late and we should be getting to bed, ready?”

“Tina, it’s just nine o’clock.”

“Yep, and it’s time for us to talk about sexual relations between a woman and her other kind of woman.”

“You’ve been watching too much Springer, but I can’t refuse an invitation like that.”


Several days passed and it was only three days before the big party. Tina was home early again. I feared that was a bad omen, and I was right.

“You’re home early,” I said.

“I know. I talked to Rita’s sister and she asked us if we were serious about doing this right. I told her we were, so she asked me to have you get rid of all your hair below your eyebrows.”

“What do you mean by that?”

“I mean it’s time for your sparse growth to go. I stopped at the store and bought you enough hair remover for an army.”

“I can’t do that. What do you think the guys at work are going to say?”

“Why would they say anything? Do you plan on doing a striptease for them?” Tina giggled.

“Of course not, its just that, you know, guys don’t do that.”

“When’s the last time you saw a weight lifter? They all get rid of their hair. It makes them look better.”

“But I’m not a lifter.”


“So? The reason I would be removing it is to look like a girl. Can’t I just be a hairy girl?”

“No you can’t be a hairy girl, you promised you would try, please?” Tina begged.

I’m a push over when she does that, so needless to say I was standing butt naked with out so much as baby fuzz a half of an hour later.

“Come here, sweetie. I have to put lotion on your body so your skin will stay moist. That remover raises heck with our skin.”

“Our skin?”

“You know what I mean, us girls, now lay down.”

I lay on the bed and Tina squeezed a dab of lotion on her hands and proceeded to rub it on my body. My skin had a completely different feel as she did. She could have breathed on it and I would have responded. It had gained a sensitivity that was, well, unnerving. I couldn’t believe how good it felt as Tina moisturized my skin. I had never felt anything as erotic as what she was doing to me. I wondered if women felt this way all the time? Tina finished my back and had me turn over. The results were even more startling as she continued to make my skin soft as a babies butt.

Tina finished and we had something else to take care of, my obviously excited member.

“My, my, does all this rubbing excite my little girl?”

“Well, duh.”

Tina removed her clothes ad crawled in bed beside me. She gasped as she rubbed against me.

“God Bill, you feel so, um, sexy. I think I could get used to you feeling like a woman.”

“Tina, this is a one time thing. After your party, Mr. Hair is coming back.”

“Pity,” she said, as she pulled me close and moaned.

Tina wore me out that night, and I have to admit that I did like the sensuous feelings I was having as Tina seduced me more times than I could remember.


The next day Tina was home early again, only this time she had brought Shelly, Rita’s sister with her.

“Hi Bill, this is Shelly. She’s the woman that’s going to make you into a starlet,” Tina said.

“Hi Shelly.”

“Hi Bill. I came home with Tina so we can have a dress rehearsal and to be sure everything fits.”

“Do we have too?”

“We don’t have to, but if you want this to succeed, we really need to alter the clothes and make sure everything is perfect.”

“Okay, I guess I can do that, for the sake of the party.”

“Good, let’s get started. Go remove all your clothes and put on these panties and the girdle and cincher you tried on the other day,” she said, as she handed me the garments that led to Tina’s and my love making session.

I did as Shelly asked and the results were the same.

“Tina, I need help,” I yelled out to my wife.

Tina came into our bedroom and giggled.

“We don’t have time for that right now, so push that thing between your legs and pull up your girdle. Don’t worry, that will take care of everything.”

I did as instructed, and it painfully did take care of my dilemma.

I joined Shelly for the rest of my big evening.

“I’m going to make you up first, and then we can work on your body. Sit here.”

Shelly had changed our kitchen table into a workstation for her to do her magic. She started by applying liquid over my whole face.

“We have to start with a blank canvas, Bill. Just relax, we’re going to have fun.”


Shelly worked on my face for an hour before she pronounced that she was done. She next helped me put on a bra and filled the cups with silicone breasts. This also made my girdle feel tight again. She helped me pull on a pair of sheer panty hose with just a hint of color, tan I think she said. She removed a dress from a garment bag and slipped it over my head and let it settle over my body. It had a collar that buttoned around my neck and then went down my chest and under my arms, leaving my back and shoulders uncovered. Even more unnerving was the fact that the dress stopped above mid thigh. The fabric was an electric blue satin. She opened a box and removed a pair of heels that matched the dress, all four and a half inches of them.

“These are sling back pumps. Don’t worry, you’ll get used to walking on stiletto heels, all us girls do. That dress is club wear and it looks good on you. I brought a real human hair wig and it will cover your back. You have pretty shoulders for a man and it would be a shame to cover them.”

I was pretty much in a state of shock by now and barely noticed as Shelly lowered the wig down on my head. She brushed if until it was exactly the way she wanted it. All the while I couldn’t help noticing my pretty legs staring back at me from beneath the dress. I was definitely going to have to work out to make them more manly.

“All done Bill, ready to see?” she asked.

If my legs were any indication of what was to come, I didn’t want anything to do with seeing anymore.

“I guess,” I answered timidly.

Shelly helped me to my feet and held on for dear life. She knew what was going to happen when those heels hit the floor.

“Oh shit,” I exclaimed as I teetered as if I would fall from a building.

“Easy girl, it takes a moment, there, now you’re getting your balance.”

How would she know if I was getting my balance? If she was to let go, her work of art would be lying on the floor. She was right though, I did finally balance enough to stand on my own, but walking would be another matter.

“Okay, Bill, now take a step. Place one foot in front of the other, and take short steps.”

That was a given, short steps. There was no way I could take big steps in these heels, even if I tried. I slowly navigated my way to the full-length mirror on Tina’s door. When I saw what Shelly had done, I knew I was in trouble. I would have jumped my bones if I weren’t already married. Shelly knew her business. Tina would have no worries about me mocking her client in this outfit. I just hoped I wouldn’t have trouble from any of the rest of the guys if I dressed like this.

“Uh, Shelly, isn’t this too much?” I asked, timidly.

“Goodness no, I just wanted to see if everything fit properly. I’ll have to take in the waist a little, but other than that, girl; you’re going to make a splash. Let’s see what Tina thinks. Tina, your woman is ready,” Shelly laughed.

Tina entered the room and she stopped.

“Holy smoke girlfriend, I’ll have the prettiest date at the party. My God Bill, you’re beautiful.”

“Um, thanks I guess.”


I had returned to admiring myself in the mirror. Looking like this was becoming intoxicating. As much as I hated to admit it, I liked the way I looked. I felt special, and I felt sexy. Now I knew why my wife went to the effort to make herself pretty, it felt nice.

“Okay good looking, time to change. I saw what I needed to see. I’ll be back Saturday in time to get you ready. Take this makeup remover, you’ll need it,” Shelly laughed.

Shelly removed my wig and dress. Tina helped with the shoes, and the makeup was left to me. I went into the bathroom and looked in the mirror. I looked like a complete dork. Staring back was a beautiful feminine face, stuck on my skinny body and sporting my usual short haircut. I couldn’t remove that makeup fast enough. The only good part of the night was that Tina used and abused me again.


Saturday came and Shelly was at our house early, like hours before we had to go to the party.

“Bill, today you’re going to become a woman. This is going to be a special day for you. I’m giving you the works.”

“Shelly, all I’m doing is going to a party in a costume.”

“Not today you’re not. I want you to remember this day always, and not because you wore a costume. You’re going to enjoy this day like a woman would. I already told Tina what I wanted to do with you so she’s running the bath. Run along now, we don’t have all day.”

I went to the bathroom and saw what Shelly meant by having a woman’s day. The tub was filled with scented bubbles and Tina had lit candles and placed them around the tub. It was romantic and it was feminine, very feminine.

“Tina, why do I have to do this? I’ll just take a shower.”

“No you won’t. I want you to feel like a girl when we go out tonight. Being a woman is more than just putting on some clothes and I want you to experience it. Now get in the tub mister, and enjoy what all of us girls do.”


I did as ordered. I slid carefully into the bubbles and felt them caress my hairless body. They felt good. They were soft and much to my concern felt feminine. Tina brought me a glass of white wine, turned on some soft music and left the room. I was left in thought. I sipped the wine and washed my body with the soft lacy ball Tina had left with me. I lifted my leg from the tub and ran the soft ball up my calf and thigh. It looked like one of those commercials on TV, except I was the woman. An hour had past before Tina came to get me out of the tub. I was relaxed and it seemed as though I had only been in the water for minutes. Tina showed me how to dry myself. Pat, don’t rub. When I was dry I noticed that I now also smelled feminine.

“Wrap the towel around your body Bill. Shelly is going to give you a facial.”

I wrapped the towel the way I usually do, around my waist, but Tina stopped me.

“Not like that, around your chest too. You’re a lady today and a woman would never walk around with her boobs hanging out.”

“Tina, I have no boobs.”

“Today you do, now wrap yourself right, girlfriend.”

I wrapped my towel like Tina asked and went to see Shelly. She had me lay on my back and then she went to work on my face. I have no idea as to what she did, but when she finished my face felt different. It was soft.

“Now it’s nail time Bill.”

“Nail time?”

“Yes, It’s time to do your nails. A pretty girl never goes out without her nails being done.”

Shelly laid my hand on the table and explained to me that I needed acrylic extensions. No, I had no idea of what she as talking about. When she finished I did. Next came the color, a very sexy red. She didn’t want my feet to feel left out so they were done too.

“Now comes the hard part, Bill. Remember the other day when I had you try on the dress? Well I found out that your bra shows on your back, so I have to glue your breasts on. I also gave you a size larger because the dress didn’t hang quite right.”

“I thought they looked big already.”

“Good grief girl, they were just normal B breasts. These aren’t that much bigger. Wait, you’ll see when you put your dress on.”

Shelly had me lay on my back and she placed the silicone blobs on my chest. She made a few marks with an eyebrow pencil after she had adjusted them to where she thought they should be. She squirted some liquid on them and placed them carefully next to the marks she had made. Several minutes later she was done.

“Okay Bill you can sit up now.”

I rose to a sitting position and felt the weight on my chest.

“These are heavy,” I whined.

“We girls put up with this every day of our lives girlfriend, now it’s your turn,” she laughed.

I placed my hands under the breasts and lifted them. If I didn’t know better, my hands would have thought they were real. I turned toward the mirror and gasped. The breasts had nipples.

“Shelly, these have nipples. Couldn’t we just use some foam or something else?”

“I told you we were going to do this right. Bill, you’re going to have fun with this, just wait and see. Let’s get you dressed in something decent so I can start on your makeup.”

Shelly put a bra on me so at least my new friends were supported. I continued to wear a robe Tina had found for me.

Shelly went to work on my face. She did just about the same as the previous session except for the fake lashes she put on and trimmed.

“You need fuller lashes, and all those girls in the mascara ads wear them too. You’re going to be a knockout Bill.”

Shelly brushed and painted. Surprisingly, though, it didn’t take as long as the first time.

“That was quick,” I stated.

“That’s because I knew what I had to do. Now let’s get your wig on, so you can dress. I still have to make Tina into that man you’ve always wanted to bed,” Shelly laughed.

Shelly put some glue under the wig and placed it on my head. I noticed she had styled it slightly and it really looked nice.

“I glued this on for you. I don’t want it to accidentally fall off and ruin all the hard work I’ve done with you.”

Tina was waiting when I entered the bedroom to dress. She handed me the sexiest pair of panties I had ever seen.

“A present from me to you,” she said.

“Thank you,” I whispered.

They were satin and covered with lace. I touched them to my cheek to feel the softness.

“Do you like them?”

I blushed furiously. How was I going to admit to my wife that I loved them? This whole costume experience was getting out of hand.

“Yes. Why did you buy them for me?”

“I want this day to be special for you. I love you so much Bill, and what you’re doing for me is the nicest thing you’ve ever done. Lingerie like this is a very intimate experience for a woman to wear. It’s worn next to the most intimate part of your body. It’s not seen by anyone but you, but it feels so special. It’s your own personal experience, not to be shared with anyone but your lover, and then only for him to remove. I want this for you, my love.”

When Tina finished saying that, she had a glisten of a tear in her eye.

“I love you Tina,” I said, as I slid the panties up my legs and nestled them against my bottom. I was surprised that I didn’t become aroused. I felt something different. I felt like a woman who had just been given a very special gift, a gift from her love.


Now it was time to get to the hard work, slipping on the girdle. I huffed and puffed as the slid it up my legs. The stretchy garment and pads finally reached their destination. I needed help with the pantyhose, so Shelly rolled them on for me and helped me with my heels. Lastly she removed my bra and attached the waist cincher before she slid the dress over my head. She brushed my hair a bit and stood back. The smile on her face said everything.

“You’re beautiful.”

I turned toward the mirror, feeling my long hair caress the bare skin on my back and looked at Shelly’s masterpiece. She was right, I was beautiful. I was afraid my exposed shoulders would look manly, but they didn’t, they looked down right feminine. I was right about my legs too, I definitely have to work out, a man shouldn’t have legs like this. I raised my arm to touch my hair and even my underarms looked sexy.

“I, I, don’t know what to say Shelly,” I stammered.

“Don’t say anything. Just go enjoy being a pretty woman and enjoy your date with your boyfriend, which reminds me, I have to get her ready too.”

Shelly left to help Tina with her costume. My feelings were mixed about what Shelly had done with me. In one sense I was excited to be so attractive, and yet I felt perverted. I shouldn’t be enjoying this, but I was. I liked the way everything felt on my body; the way the dress hugged my fake shape and the weight of my breasts. I had truly been transformed into a woman.

I decided to practice walking in the impossibly high heels, so I walked from one room to the other. Tina saw me and smiled.

“Stand a little straighter and place on foot in front of the other, perfect, you’re a natural, Bill.”

“Thanks,” I replied.

Now my voice sounded funny to me, a woman shouldn’t sound the way I did.

“Shelly, is there something I can do with my voice?”

“There isn’t much you can do in a short amount of time. The best you can hope for is to speak a little higher and softer. Pretend you are singing as you talk.”

I did as she instructed and I did sound better, kind of like a girl with a bad cold.


Shelly finished with Tina, and much to my surprise she looked like a young man with soft features. I was going to be proud to have Tina as an escort.

“Oh Bill, just a few more things,” Shelly said.

She reached into a bag and took out some thin silver rings.

“You need jewelry.”

She placed ten rings around my right wrist and a watch on my left. A pair of clip on earrings finished my look.

Shelly smiled as Tina approached me.

“May I present Mr. Anthony Windom, and his lovely wife Ashley,” she said.


“Of course dear, we can’t have a beautiful woman like you being called Bill all night.”

“But Ashley? That’s such a feminine name.”

“And you’re a feminine woman. Enjoy it girlfriend. You’re an Ashley, no doubt about it. You two had better call a cab. The party starts in half of an hour and I want you to show off all my hard work.”

“Thank you Shelly, you’re a wonder,” Tina said.

“Oh Ashley, be careful with your dress. If anything was to happen to it, my head will roll.”

“I will be, thank you Shelly,” I said in my new feminine voice.

“You’re a very sweet girl Ashley,” Shelly said as she embraced me. “Be careful and don’t break your ankle wearing those shoes.”

Shelly did one more thing for me. She handed me a small clutch bag for my lipstick and cigarettes. Did I mention that I smoke every now and then?

“There, all done.”


Tina called for a taxi and one came fifteen minutes later. The driver couldn’t help but snicker as the short man and tall woman entered his cab. Tina held the door for me and helped me sit. She watched as I swung my legs inside. She went around the car and slid in next to me. Her arm went around my shoulder. It was a very masculine thing to do. The driver’s eyes hadn’t left the rear view mirror and the reflection of me in it. It was creeping me out having another man stare at me like that.

“Where are you two going?”

Tina gave him an address on Hollywood Blvd and he drove off. It took almost a half of an hour to reach our destination.

“Pull into the garage, the entrance is inside,” Tina ordered.

The driver smiled. There was no way he was going to mistake Tina for being a man with her voice. I assumed he must have thought we were two lesbians out for the evening, but it still didn’t deter him from constantly watching me in the mirror.

The driver stopped in front of the door to the club. Tina paid him and we exited the cab.

“You girls have a nice night,” he laughed.

Tina just glared. Me? I smiled, I guess I had just passed the test; I was now officially a woman.


We entered the club and I looked around. I wanted to laugh, but remembered that I too was one of the people in costume. Some of the guys were pathetic as were some of the wives. Others looked as though they had spent as much time as Tina and I on their costumes. It was a mixed bag, some men were pretty, and some not so. I think Tina and I did look better than anyone else so far.

Ralph Sanchez came walking over to us. Ralph is one of the vice presidents whose title doesn’t change every other week. Ralph looked as though he had spent a considerable amount of time dressing, but because of his build, he was, well you get the picture. He looked as much like a woman as Tina sounded like a man.

“Tina, is that you? This can’t be Bill?”

“It’s us Ralph,” Tina giggled.

“It’s a good thing Bill didn’t come alone, or I might have had to change my costume,” he laughed. “How did you do it?”

“Rita’s sister helped us. She did an amazing job on Bill, didn’t she?”

“If I didn’t know any better I would have thought your brought one of your girlfriends with you. Come on in Tina, and show off your beautiful wife,” he laughed.

There was an open bar so Tina escorted me to get a drink. Tina ordered a Cosmo for me and a beer for herself.

“Got to keep up appearances, Ashley,” she laughed.


I looked around the room and for once everyone was laughing and having a good time. Most other years the noise level was about half of what it was now, and most of what was being said was all in good fun. The comments were all pretty much the same, and closed with what a butt ugly woman a person was, or it was no wonder a man like that never married. The laughs were long and hard, except when it came to me. I thought it was creepy when the cab driver stared at me, but you have no idea of what it’s like when a man in drag is lusting for you. The good part was that it didn’t last long and everyone pretty much grew tired of the initial shock of seeing everyone dress as the opposite sex.

Dancing started and then I had my laughs. It looked as though I had returned to the eighth grade. All the women were tall and their partners were short. I still remembered those times and the first school dance I attended. I think there were maybe two or three guys that weren’t a full head shorter than their dance partner.

“What’s so funny?” Tina asked, as she felt me sides moving with my laughs.

“I was just remembering the eighth grade. Nothing’s changed, the girls are still taller than the boys.”

Tina started laughing too as she looked around.

“You’re right, I remember my first dance. I was as tall as I am now and poor Jimmy Carl was my partner. I had started developing the year before and his eyes were the same height as my breasts. He couldn’t stop staring at them. Now that I think back it was really funny.”

We danced several more dances and Tina refilled my cocktail. It was my third, and even though I had spread them out I was feeling loose and relaxed. I wasn’t self-conscious about being a woman anymore and was enjoying the moment. There is one thing bad about alcohol, it makes a smoker want to smoke. Unfortunately in California we have laws about smoking inside of a building, you can’t.

“Tina, I need a cigarette, I’ll be right back.”

“Don’t get lost and don’t fall in love with any of these mini-men if they hit on you,” she laughed as she took another mouthful of beer. Tina was obviously feeling her drinks more than me.

“Is there a place where I can smoke?” I asked the hostess.

“You can smoke in front of the building, or outside the emergency exit in the rear of the club,” she said.

“Thank you.”


There was no way I was going to walk out in front of the building on Hollywood Blvd to have a smoke, not dressed like this. I walked to the rear and found the door to the emergency exit. I pushed the bar and the door opened into an alley, which led to the street at the rear of the building. I opened the door all the way, but the closer wanted to pull it shut. I noticed a stone next to the wall where the door would hit and surmised that it was used to hold the door open when smokers were out here. I blocked the door with the stone and lit up my cigarette. It looked sexy between my painted nails. Everything I was doing this evening was feminine, even this.

There was a light across the alley mounted high on the exposed brick wall. It cast shadows that were, to be frank, rather scary. I walked across the alley and stood under the light, thinking that I would feel safer standing under the bright light.

I don’t know how much you know about Southern California this time of year, but this is when the famous Santa Anna winds kick up. They drive wild fires to burn thousands of acres in a single day. I hadn’t noticed any breeze when I opened the door until a gust took the door and pushed the stone out of the way, the result being that the door slammed shut before I could react. To make things worse there was no handle to unlock the door from the outside. I could hear the dance music coming from inside and wondered if anyone would hear my knock. I swore and threw the cigarette on the ground rubbing it out with the bottom of my heels.

I knocked on the door for several minutes and my greatest fears had been realized. I was locked out and no one could hear me. How in the world was I going to get back into the club? I knew I could walk around the block to the front and enter that way, but then everyone I didn’t want to see me, would. The alley was quiet and I thought I could wait until someone else came out to smoke. I looked around and noticed a pile of boxes pile against the wall at the end of the alley. A rat ran along the wall and into the boxes. I wanted to scream, wouldn’t any other girl, I asked myself?

‘Shit,” a voice yelled, as the pile of boxes erupted.

A homeless man jumped up after being startled by the rat. I wasn’t alone any longer and being near a man like this was something I didn’t want to happen. He had the usual facial hair stained by the cigarette butts he had picked from the street. His hair was matted against his head and half of his teeth were missing. He was wearing layers of clothing, and most were shredded.

“You okay honey? The rat didn’t scare you did it?” he asked, with his gravely voice.

“No, I’m fine,” I answered, in my hopefully feminine voice.

“What’s a pretty thing like you doing in here? You get lost?”

The man started to walk toward me. I could smell his beer laden breath and the stench of months without a bath.

“I have to go,” I said, as I started to back away from him and turned to walk from the alley.

“Don’t run off on account of me, sweetie,” he grumbled, as he walked at a quicker pace.

“Leave me alone,” I screeched, moving as quickly as my heels would allow.

I reached safety of the street behind the building. My plan not to be seen had failed and now I had no choice, I would have to walk around the block just to get back into the party.

I was shaking as I slowly walked from the alley entrance. The homeless man had stopped chasing me, but that didn’t quell the new feelings I had. I felt like a woman, and I felt vulnerable. I knew how provocatively dressed I was and to be honest, I would have pursued me in a heartbeat. What would the reactions be from other men on the street? Would I be safe to walk without incident? Now I had two things I had to take care of, build my muscles and quit smoking. Both had brought me to where I was at this moment. Why did Shelly have to do such a good job, and why did I have to look so feminine in the first place.

I gathered myself and quickened my pace. My heels were announcing my every step. There were a few people on this street, mainly someone that had found parking and was walking around the corner toward Hollywood Blvd. I felt every eye watching as I continued. Did they think I was a pretty girl, or did they see the man under all the makeup and clothes? Please, I begged myself, let it be the first. Let them see the girl I was portraying.


I rounded the corner and walked the short distance to Hollywood Blvd. Every step reminded me to thank my lucky stars that men didn’t wear heels like this. I turned onto the main street and was taken back by the amount of people. There were crowds everywhere. I gathered my courage and continued walking. I wasn’t getting any obscene remarks, but I was getting stares from men, those, and smiles. What should I do? My feelings of vulnerability were still there, but now I felt something else. I felt pretty and I felt proud. I stood straight and continued walking.

“I just fell I love,” the first guy said.

I couldn’t help myself; I smiled, not at him, but at the remark. It was so corny but it made me feel good to be having this effect on someone, although I wish it wasn’t a man.

“Hey,” I heard a girl shout, “You, come here.”

A very pretty girl was waving for me to come over to her. What was this all about, I wondered? Hopefully she wasn’t going to go off on me for being dressed this way.

“I need your help. One of our girlfriends was in an accident and she can’t make it here. I told the doorman that four of us girls wanted to get into the club and he said when she got here we could go in. Would you please go in with us, pretty please?” she begged.

“But, I’m trying to get back to another party,” I said, in my most feminine voice.

“You can leave as soon as we get in, and besides you’re so pretty the door guy won’t want to keep us out. How long have you been a girl?”

I felt my face go white under the makeup. How did she know?

“How did you know?”

“Your voice. You really are pretty. If you hadn’t spoken I would have never known. Will you help us?”

“I will, but please don’t say anything about me, okay?”

“Girlfriend, you’re one of us now, and we stick together. What’s your name?”

“Bi, oops, I mean Ashley.”

“Welcome to the other side Ashley. Girls this is Ashley. I’m Shauna, this is Mary, and Kayla.”

“Hi,” I whispered.

“Are you okay? Do you have a cold?” Kayla asked.

“Yeah, she has a cold,” Shauna said, as she poked me in the ribs. “Let’s go girls.”

Shauna led us to the door and we were waved inside after our hand was stamped. The music was so loud you could hardly hear. Shauna guided us to an empty table and we all sat.

“I have to go,” I said into her ear.

“Wait for just a minute, you’ll see why,” she responded.

Four drinks arrived at the table, all of them Cosmos. I guess everyone thinks all girls’ drink are chick drinks. Four guys soon followed them; eager to meet the women they had spent their hard earned money on.

“Let’s dance,” one shouted.


We were all pulled from our seats by the guys and led to the dance floor. My guy was taller than me even in my heels. The music was fast so there was no touching, but he kept looking at me, and smiling.

“What’s wrong?” I whispered, just loud enough for him to hear, and feminine enough for him to think I was what I appeared to be.

“Nothing,” he shouted. “I’m just thanking God that I found the prettiest girl in this place.”

I blushed when he said that. It felt good to have a compliment like that. I also knew I had to go, and if I stayed nothing good would come from it. Being a girl had become fun, but the deception wasn’t me.

“I have to go to the bathroom,” I mouthed to my partner, and held my hands over my dress pretending that I had to go really bad. He escorted me to the table and sat to wait for my return. I grabbed my purse and walked through the crowd in the general direction of the little girls room. When I reached it I kept walking past the door and out the entrance of the club.

“Do you have your stamp?” the doorman asked.

I nodded yes as I turned down the street in the direction of Tina’s party. It took only a few minutes and I finally returned to find a frantic Tina.

“Where have you been?” she asked. “We’ve been looking all over for you.”

“I got locked out.”

“I know, but when we opened the door, you were gone.”

“There was a man out there and he scared me, so I ran from the alley.”

“Why did it take so long to get back?”

“I went to another club with some girls, I’ll tell you about it later.”

“Come dance with me and then we’ll go,” Tina said, as she took my hand and led me to the floor.

It was a slow dance and as silly as it seemed, quite romantic. I tried to put my head on Tina’s shoulder, but there was no way I could get that far down, so we held each other tight. The dance ended and so did our evening. We could hardly wait to get home and Tina wanted to hear of my wild adventures away from the club.

“Tell me what happened after you got locked out of the club?” she asked, as soon as we walked through the door.

“You know I was locked out and then this homeless guy came after me. God I was so afraid. I ran from the alley and walked around the block to get here. As I was passing the club by the corner, a girl asked me to help her and her friends to get in the club. She knew right away I wasn’t a girl, but she didn’t care and so I helped her and her friends get in. A guy even bought me a drink,” I said proudly.

“A guy bought you a drink?” Tina asked, with obvious concern.

“He said I was the prettiest girl in the club.”

Tina didn’t say anything for a moment. She just looked at me.

“How did you feel when he said that?”


“Did you like it?”

“I don’t know. I liked the attention, but not the guy thing. It felt good to be admired and when he told me I was pretty, I felt something inside, like all the work to look this way wasn’t wasted.”

“Did you like being Ashley?”

“Not at first, but when I got used to it, I did, except for a few things.”

“Like what?”

“The feeling of vulnerability. It scared me. The way I look right now is like hanging a piece of chicken over a pit of alligators. The men were the alligators and I was the chicken.”

Tina smiled wistfully.

“Welcome to the club Ashley. What about the rest of it?”

“It’s hard for me to explain. There were moments I wouldn’t trade for the world. Looking at myself for the first time and seeing how pretty I was and watching the reaction from men, knowing that if I wanted they would have done anything I asked. I loved the femininity of all I felt after I realized everyone saw me as a woman. It was intoxicating. I felt different, soft and sexy, I loved this night Tina.”

“Would you want to do it again?” she asked, somewhat fearfully.

“No, I don’t think I would. My vulnerability never left me, not once. I like being a man. This was a one-time thing, and I learned more about myself and you that I could have in ten years. No Siree! I think we’ll stick to who we are and not who we could be. Now, are you going to make love to me, or do I have to find myself another man?”

“You’d better not Missy! You’re mine and don’t you forget it! Now get your butt in bed.”

The End

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