In Too Deep!

by

Jean M. Chambers

 

"What?" I asked, stunned, "Why? What have I done? I thought our relationship was good."

Felt like a deer in headlights and had to sit down. Maria and I had been lover’s for the most part of a year. We got along great, although lately she had been acting distant.

"I want to see other men."

"But I thought we were a happy couple?"

"It’s not that I’m unhappy, Jim. I’m just not happy being with one man." She said sympathetically, sitting down next to me.

"But I love you, Maria! I don’t want you to leave. I just want to be with you. Close to you. I don’t care if you date other men. I just don’t want you to leave." I pleaded.

I had never cared for anyone like I did Maria. It was love at first site, a love that turned into an obsession.

"I need my space." She said, "I want to date other men. Having a male roommate kind of puts a damper on that. As soon as a guy finds out you’re living with another guy, they assume the worst. If you were a girl, there would be no problem."

She kissed me on the cheek, picked up her bag of things and started for the door.

"But…" she hesitated, turning back slowly in deep thought, "if you were a… No. That would be out of the question." She dismissed the thought and started for the door again.

"What?" I sprang up from the couch, "What is out of the question?"

She had her hand on the doorknob. She stopped.

"Well…" Maria sighed heavily, "If you were a girl, or at least was willing to look and act like a girl, I would consider staying. We could live together as girlfriends."

 

"Yes!" the word flew from my lips.

I didn’t even consider what she was saying. If she walked out that door, I knew she would not be coming back. I was desperate.

"I do mean… a girl, Jim. You do understand what I am saying. Right? You’ll have to live as a girl from here on out. There will be no backing out next week. It won’t be easy. You’re a guy. You’ll have to learn to be a girl. Completely."

She stared at me. I didn’t care what she meant. I would agree to anything to stop her from leaving. Nothing could be worse than that.

"Yes, I understand. I’ll do it. If that is what it will take for me to stop you from leaving."

"Okay." She said hesitantly, "But, you start tonight. Not tomorrow. Not next week. Tonight. Be certain you want to do this," she said intensely, "because I’m not joking. You won’t be able to back out, once we start changing your looks. In for a pinch, in for a pound. You’ll live completely as a girl."

‘So what?’ I thought. I’d get my hair cut in a feminine style, pluck a few brows, shave my legs, and wear women’s slacks and blouses. I’d make myself look androgynous, like lots of women look.

"Yes. Sure. Tonight. I’ll start tonight" I heard myself agree.

 

She smiled. Her eyes got brighter. It made her look devious.

"Good!" she said, satisfied with our deal, "Let’s see. Where should we start? Hair? Yes. Definitely, the hair. We must change your hair. Go shower and shave. Your, body I mean. Legs, arms, chest. All of it, except your head. You need to be smooth as a baby. Girls don’t have hairy bodies. I’m going to run down to the pharmacy to get some things. We’re going to give you a new hairstyle."

She giggled and left. I quickly went to work, showering and shaving. It took way longer than I thought. After nicking my ankle, knee and elbow with the shaver, I was wondering if I had made a mistake. I would have to do this at least every other day. Maria came into the bathroom carrying a bag just as I finished drying myself.

"Sit!" she said, pointing to the potty seat.

I did. She pulled a package of hair color out of the bag, opened it, mixed two bottles of liquid and started applying it to my hair. Then she put a plastic cap over my hair and said I would have to wait twenty five minutes. The hair color stunk and burned a little. She stooped down in front of me with a pair of tweezers and started plucking my eyebrows. It hurt and I pulled back.

"Get used to it. This is a daily thing for most girls. We’ll have them lasered sometime this week, but this will do for now. Twenty minutes later she was finished. My brows felt sore from all of the tweezing.

"Just like Madonna" she said, obviously happy with her handy-work, "now lets look at those nails. Oh, my. You need a full pedicure, girlfriend. It’s going to be fun being roomies. Just the two of us girls. Like in my Sorority back in college. I think a shorter fashion nails will be good for starters, until you get used to them. Then we’ll make them longer."

She went to the hall closet and came back with a shoebox full of items, including nail tips. Twenty minutes later I had a nice set of one inch nails, painted frosted pink to match my outfit. The polish stunk. I never could see how girls could stand the smell, and I never dreamed I’d let anybody paint my nails with it. I cringed to my core. My hairless arms and hands looked like girl’s now.

 

I stepped back into the shower and rinsed the hair coloring out of my hair, then sat back down on the potty seat. My hair had been long, slightly past my shoulders, before she started. She left it long in the back and cut curved bangs across the front. The sides were cut in a sweeping curve, down along my shoulders. Typical female style, I thought. It looked more feminine than I had counted on. I choked when I saw myself in the mirror with the new hair dew, color, and femininely shaped eye brows.

"I can’t go to work looking like this! I look like a girl. They’ll fire me."

"It’s not like you have a career or anything. You’re a waiter for God’s sake. We’ll worry about your job later."

Maria was giddy about the basic changes she had made. Changing me into a girl excited her. She dragged me to the bedroom. She was on a mission.

"Put this on" she commanded, with a smile.

She held out a pink lace bra, letting it dangle from her finger, as if she was daring me to take it. I didn’t want to. I was having second thoughts again.

"Is this really necessary?" I asked.

"Well, duh, yes." She said sarcastically, "It’s part of your new life. If you are having trouble with wearing a nightie in the privacy of your own home, how are you going to handle wearing dresses and skirts in public? Maybe we should just forget the whole thing. It was just a…"

"No! No, I’ll be alright, Maria. I can do this. It is just that… What do you expect? I’ve never worn any girl’s clothes before. I’m a guy and this is a big change. A real big change."

I had never put a bra on before and had trouble hooking it behind my back. Maria gently turned me around and did it for me. It was snug around my chest. Very snug. The bra would take some getting used to. It felt strange.

"If only I had something to put in it" I kidded nervously.

"You will, soon enough. Consider this training to get you used to the feel of wearing one, every day, all day. You’ll understand why women complain about bras very soon. Of course, walking around with bouncing breasts isn’t much of an alternative. The bra is a better choice. Trust me."

She pulled the back of my bra strap and let it snap against my back. It stung and I shrank away from the stinging in my back. She laughed.

"I’ve always wanted to do that to a guy. For some reason, they think it is funny to do that to girls, but it isn’t, is it?"

Maria was having fun at my expense. No, it wasn’t funny. It hurt.

 

I slipped into a pair of matching panties, then a pink baby doll nightie set. It looked similar to one of the Femmebot outfits from an Austin Powers movie. Even without any makeup, the hair and nightie made me look similar. She dug into the closet and tossed a pair of pink mules at me to slip on. They were a little small, but fit okay because of the open back. Maria was bubbling.

"Oh! I almost forgot. Here!" she tossed a bottle of pills at me, "A present from my girlfriend at the pharmacy. Take two, twice a day."

"Hormones?" I asked, reading the label.

"Sure. They’ll help you look more feminine. Maybe even give you breasts." She giggled.

"Breasts?" I asked, surprised, "I don’t think I need breasts."

Breasts weren’t in my plan. Sure I wanted Maria to stay, but bouncing breasts weren’t something I had bargained for. Having breasts went against my moral fiber. Only women had breasts. Even though I was going to dress, look, and act like a female, I didn’t want breasts.

"Oh yes you do, little lady." She chastised me, "All girls have breasts and if you are going to live as one, you’ll have them too. Besides. You’ll need them to fill your clothes out properly. They won’t hang right, otherwise."

It was bedtime before we finished. Maria stopped me when I started to lay down on my side of the bed.

"What are you doing?" she demanded with her hands on her hips.

"Going to bed." I replied.

"Not in my bed, you’re not. Girls don’t sleep together! Not unless you’re a lesbian, and I’m not. From now on the spare room is yours. I’ll help you decorate it when we get time."

She waited expectantly for me to leave. I accepted my fate and headed for the spare bedroom. She smiled as I passed, looking me up and down. Maria slapped my lace panty covered rear as I passed. It stung. She laughed.

"And before I forget, I’m going to run some early morning errands tomorrow so you may as well sleep late."

I grunted an acknowledgement over my shoulder.

 

I awoke the next morning to Maria’s cheery voice.

"Come on sleepy head. Time to get up. It is almost noon and I’ve got some new clothes for you to try on."

She sat on the side of my bed shaking me. My nightie was wrapped around me like a boa constrictor. It confused me a at first, until I remembered why I was wearing it. I stumbled to the bathroom to washed up and fix my hair. It was chilly in the tissue thin, pink nightie. My platinum blonde hair was striking, against the pink. Maria had laid out some clothes she had bought for me on the bed. They were second hand. She had bought them at a thrift store, but they looked fairly nice. I pulled on a pair of new pantyhose and slipped into a white blouse and plaid skirt suit. The skirt fell above the knee and the jacket only came to my waist. Both were contoured for a woman’s shape. I felt naked from the thighs down, having never worn a skirt before. Maria scooted a pair of black patent, three inch pumps in my direction and I slipped them on. They were a little snug, but they fit.

"Now," she smiled, taking me in, "you are starting to look like a real lady."

I felt ridiculous standing there in the outfit. So, I thought, this is what it’s like to be a woman in a skirt and heels. I walked around the bed, trying to get the feel of walking in the high shoes. The skirt was binding around my thighs and made me take smaller steps. The nylon lining slipped against my nylon clad thighs, sending a chill up my legs. I liked the sensation. While the outfit was very conforming, it was amazingly comfortable.

 

"A little makeup and we’ll be ready to go." approved Maria.

"Go? Go where? I’m not going anywhere in this skirt."

opened my closet to get a pair of slacks out but it was empty. All I could do was stare, dumbfounded."
My clothes were gone. All of them. Every stitch. Gone! Maria smiled triumphantly at me from across the room and raised her brows.

"Is something wrong?"

"My clothes. Maria! What did you do with all of my clothes?"

"You’re clothes?" she snickered, "My dear, you’re wearing them. I got rid of all those ugly men’s things this morning while you slept. You looked quite cute in your nightie, by they way. Like a little angel."

She giggled. I didn’t know what to do. All of my clothes were gone. I raced to the dresser, twisting my ankle a little in the heels I was wearing. The drawers were empty too.

"Not to worry, I’ve bought you new under things. Silky, lacey, under things. Something more fitting a lady."

She patted a large bag laying on the bed. I stared as she dumped the items on the bed. It had been full of women’s lingerie.

"Now," she stood up, "let’s get started on your makeup, shall we?"

She led me into her room and sat me down at her makeup stand. I sat in a daze as she smoothed foundation over my face, applied eye shadow, liner, blush, and lipstick.

 

The gravity of the situation weighed on me as I stared at my new self in the mirror. I was pretty. Not beautiful, just pretty. I was a woman. Not physically, of course, but anyone who saw me would never know. All they would see was a pretty, business woman.

"Wow," said Maria, "what a difference. You make a fairly good looking woman. Better watch out. The guys will be hitting on you."

She jabbed me in the shoulder. My stomach sank as her words rang through my mind. Guys will be hitting on me. Oh, my God! She was right. Making passes at women was just an everyday thing to most guys. Now that I looked like a woman, I would be subject to men’s remarks too. The thought was not a pleasant one. I imagined a guy grabbing me around the waist and pulling me close to kiss me. The thought turned my stomach. In my haste to stop Maria from leaving, I hadn’t fully considered what living as a woman meant.

 

"Come on, honey, or we’ll be late. You’ve got an appointment for some laser hair removal and we don’t want to be late."

"Laser, hair removal?"

"Hello?" she asked, knocking me on the head, "Girls don’t have beards, or hadn’t you noticed? I’ve covered it pretty good with the makeup, but permanent removal will be required to really pass as a woman."

I let her tow me to the living room, where I almost panicked. Maria’s friend Jane was sitting quietly on the sofa. I had known her for a long time. An amused grin spread across her face when she saw me. I felt like dying.

"Oh my gosh! She said, cupping her mouth with her hand, "Jim? Jim? You look so… so… so pretty!"

she looked me up and down lingering on my smooth legs for a moment. My face felt like it was on fire. How could Maria pull a stunt like this on me?

"I told you he was a doll, Jane. He is, isn’t he?" Maria clucked in delight.

"With legs like those, he’ll have to beat the men off with a stick. I’m jealous! Jim, I never knew you could be so pretty."

"Enough already." I complained, "It is bad enough to be standing her dressed like a girl. Fawning over me just makes me feel worse."

"Oh, you’ll get used to dressing as a girl after a while. When some guy looks at your legs, or hits on you, you won’t even notice. It’s common place."

 

It was obvious Jan was coming with us. Maria tossed a purse at me from the hall closet.

"Never leave home without it. It’s a girl’s best friend, right Jane."

"Undoubtedly." She agreed, "Once you get used to having a purse, you’ll be lost without it. Trust, me."

They giggled like school girls with a secret. We passed some people on the way to the car in the parking lot. I waited to hear them scoff at the guy in the skirt, but nobody seemed to notice us. They only glanced at us for a second. We were just three women going out together. Three hours later we were leaving the Electrolysist’s. The procedure had been painless. The technician said any new hair that grew in would just fall out in a few days. I made two more appointments before leaving, as suggested. Holding a conversation was not so bad either. I just raised my voice a little and talked like I normally would. It wasn’t totally feminine, but it was acceptable.

Maria and Jane made idle chatter as we drove. Twenty minutes later we turned into the parking lot of a Irish pub, where Maria and Jane worked as waitresses, called the Blarney Stone. Maria and Jane said they had a surprise for me. I followed them inside. It was dimly lit. We wound our way to the back of the restaurant and through the kitchen to the office where a heavy set, older woman worked. She smiled at Maria and Jane as we entered.

 

"Well, hello girls." She greeted, then looked at me, "This must be the new girl you promised to bring in."

"Yes." Maria stepped aside and did introductions, "Betty, this is Janine, my new roomy. Janine, meet Betty. Betty is the manager here."

"Pleased to meet you, young lady. The girls here tell me you need a job, and we sure as heck could use some help. I just lost two of my girls and could sure use some help in the lounge."

"Lounge?" I asked as feminine as I could.

"Yes. Maria said you had waited tables before and that you knew the difference between a Tom Collins and a Whisky Sour, so I told her to bring you in. You can fill out an application later, right now, let me get you a uniform and introduce you to the other girls. You look like a sixteen to me, so, here you go"

She pulled a white peasant style blouse, a very short skirted, green, jumper, and a pair of matching green ruffled panties off a shelf and handed them to me. Maria and Jane giggled silently behind her at my expression when I saw the outfit. We followed her back out through the kitchen.

"I’m not wearing this!" I growled quietly to Maria.

"Yes, you are.."

"No, I’m not! Look at it. My rear will be showing. The skirt is so short."

"That’s the idea, dear." Interjected Jane, " Relax. You’ll look great. No one will care. You’re a girl now. It’s a typical cocktail outfit. Besides, it helps with the tips."

"Why can’t I wait on tables in the dining room, like you guys? You don’t have to wear one of these things. Why should I? I want to wear black pants and a green shirt like you two." I hissed at them through clenched teeth.

"Sorry, Janine" Maria smiled back at me, "Cocktail waitresses wear those outfits and you are a cocktail waitress."

 

"You can change in here." Said Betty, pointing to a ladies room door as we passed, "We’ll be in the lounge when your ready."

I watched them walk across the dining room and through a doorway where loud music was emanated. The restroom was pink and empty. Pink! I never liked pink. Why did they paint everything for women pink? I stepped into a stall and stared at the outfit. Things were going too far. I agreed to live as a girl, not run around half naked in a bar, serving drinks. Maria and Jane were dying to see me, Mr. macho guy, dressed up in the skimpy little leprechaun girl outfit. The epitome of a working class girl. I pulled the puffy shouldered, white, blouse over my head and buttoned it at the back of my neck. It had a ruffle fringed, low cut, bodice, designed to show off a girls breasts. My heart pounded. I was nervous enough wearing the skirt suit. This outfit went to the extreme. If I really was a girl it wouldn’t matter, but I wasn’t. I stepped into the green, ruffled panties. They looked like a large version of ruffled baby panties, except they were green. One last piece to put on and I would be completely suited up. There would be no turning back. I would be committed. I would be in too deep. The thought crossed my mind to just leave and let Maria walk out of my life. Then, like in a dream, I saw myself stepping into the short jumper. I zipped and buttoned the skirt at my side and fastened the bib over my shoulders. The puffy shoulders of the blouse looked cute sticking out of the jumper. Heck, the whole outfit looked cute. I looked cute! Just like the other cocktail waitresses I saw standing in the lounge door way. A cocktail waitress, for God’s sake. A cocktail waitress! Me! A man! Reduced to a freaking cocktail waitress. I felt naked in my high heels. Sure, I liked to oogle girls wearing outfits like the one I now had on. I just never dreamed I would actually have to wear one myself. I gathered up my clothes and headed out to the lounge.

 

I almost collided with a blonde girl wearing the same outfit on the way out of the restroom.

"Hi!" she greeted me, all bubbly, like I would expect a blonde to.

"Hi." I said back, extremely conscious of myself in the outfit.

"You must be Janine." She looked down at my legs and I felt naked again, "I’m Tracy. Betty told me to give you this for your hair. She forgot."

"Oh," I said, taking a green hair scrunchy from her, "Thanks. Part of the outfit I assume."

"Oh, yeah." She curtsied, "Tinkerbell at your service."

She giggled like a little girl and I imitated her the best I could. I felt and looked ridiculous in the outfit.

"Here," she said taking the scrunchy back and stepping behind me, "let me show you how the other girls wear these."

Tracy pulled my hair taunt, then braided it into a pony tail, coiled it on the back of my head, and wrapped the scrunchy around it to hold it in place.

"There!" she smiled, "Welcome to the club. See you in the lounge."

She giggled her little girl giggle as she left. Her short, flared skirt swished as she walked and her ruffled panties could be seen peeking out from beneath. I checked my look in the mirror again for a minute, noticing that my panties could be seen also. Yep. The look was complete. We all looked like little munchkins. A lady came in, dressed to the nines, checked me out with a glance, dismissed me as an employee, and stepped into a stall. I took a deep breath and made my way to the lounge.

 

 

 

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© 2002 by Jean M. Chambers. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.