Miss Monica's maid Pt. 03

My humiliation at the hands of Monica had reignited some old feelings. For the next couple of days, I spent a lot of time in heels and a skirt as I worked on the final draft of my latest novel. I didn't go all the way. I didn't add boobs or make up or even a wig but it felt very comfortable and natural as I moved around the apartment.

Suddenly my phone rang. It was Monica. This was Wednesday. She was due back to clean on Friday. I feared she was calling to cut me loose. The idea of cleaning for a cross dresser just wasn't something she was happy with.

"Peter, it's me."

"Yep, your number came up on the phone. I can guess what this is about. I understand, but please, please don't tell anyone about this."

"This isn't what you think", she replied. "I need your help. Or to be more accurate, I need Jennifer's help."

My cock stirred. "What do you mean?" I asked, the hesitation obvious in my voice.

"I have a big event on Friday. It could lead to an important contract. Essentially, we're working a private party and if we do well, the guy will give me a contract for two of his office blocks. It's potentially worth a lot of money."

"And?........"

Two of my regular girls can't do it. They have child care issues. I have recruited a friend. And I need one more. Would Jennifer help me out?"

I swallowed. Hard.

"C'mon Monica. If this is a big deal, can you really risk having me there?"

"Ok. Couple of things. Even when you rushed your little performance for me, you passed easily as a girl. Your mannerisms were feminine, your make up impressive and your boobs were lovely. Second. I am desperate and I will be very grateful."

"Wait. You need me to wear my maid's outfit? I'm not sure this is an event I want to attend."

"Look, it's like a cocktail thing. There'll be bar staff. I'm just proving a few serving girls who will also help clean up at the end. Nothing dirty. Nothing kinky. And no, I'll provide the uniform. It'll be classy."

"I don't know. It's a big ask."

"Please Peter. I need your help. I honestly tried like five other numbers. I wouldn't bother you if I wasn't desperate. And I'll be really grateful. Look I'm due at your place on Friday to clean. Why don't I come a little later than usual, clean the house and then help you wiggle into your uniform?"

"Wiggle? How tight is this thing going to be?"

"I'm guessing you're a size eight, no more than a 10, right?"

"Good eye. Eight bottom and 10 top. 10 if it's a dress".

"And you have the black heels you need already."

There was a long silence. I guessed whoever spoke first would lose. But part of me tingled with the idea of dressing fully again. And having Monica, lovely Monica, owe me a favour. That tilted the table.

"OK" I whispered.

"Ok"? said Monica much louder.

I swallowed hard. "Yeah. Ok. I'll do it. But if it looks at any point, I've been read then we make our excuses and I go. You don't need to blow this because of me."

"Read? You mean discovered? People thinking you are man?"

"Not thinking. I mean working out I am actually a man."

"I wouldn't ask if I didn't think you could pull it off. So welcome to Monica's Maids Miss Jennifer."

I spent two days before Monica's return in a heightened state of excitement. I shaved everywhere from the neck down. I tried a few outfits on, and worked on some makeup ideas. Even if I say it myself, I looked good. Monica texted me first thing Friday morning. "Pete - will be around at 2. I can clean the flat then if it's ok with you, I'll get ready for the event and help Jennifer get ready too (if she needs any help) and both of us can head from there. I have the uniform. Anda template for the look I want all the girls to have. You just need shoes (and probably boobs). Xx"

I liked the kisses at the end of the message and my cock stirred again. Not getting hard around her was going to be the biggest challenge of the evening.

I watched the clock slowly tick round till two. It was painful. And then it ticked passed the top of the hour. By ten past I was sure she had gone off the idea and breathed a sigh of both relief and disappointment when the doorbell rang making me jump.

I opened the door and Monica stood there in a loose T shirt, cut low enough so I could see her cleavage, her tight jeans and her tennis shoes. She carried a garment bag and a small make up kit. She looked wonderful as ever and I felt myself growing in my shorts.

"You're smooth" she noticed looking down. She couldn't help but see I was aroused.

"I'll do the cleaning first, then we'll sort Jennifer out."

The knot of excitement in my stomach grew. I tingled all over with anticipation. This was a huge step. We chatted as she cleaned - but not about what lay ahead. Mainly about sports, my novel and world events. We agreed the Jets sucked, the plot of my book sounded good and the world was essentially screwed. It helped take my mind off the task ahead.

"Right. All done. I'll go shower - then while I'm sorting my face, you can get scrubbed up too and invite Jennifer to join us." She took maybe five minutes and emerged with the towel tucked under her armpits, and her hair piled high on her head. She looked fantastic. She stretched to do something to her ponytail and the towel dropped. For a second, she stood there in all her naked glory. Her tanned skin, her soft curves and firm breasts. I felt a surge of electricity race through my body and a surge of blood to my cock. No woman - not one - had ever had an effect on me like this.

She quickly pulled her towel up, but rather than be embarrassed, she gave me the cutest smile. "Ooops" she said. "I normally charge for a show", she smiled. "Right get in the shower. Use the gel I brought; it will make you smell more girly. And shave anything that needs shaved. And go over your face a couple of times. By the time you're done, I will be ready for Jen. And while you're in there, please do something about that" she added pointing at the obvious hard on in my shorts. "This dress isn't forgiving enough for that."

Slightly red faced, but massively turned on, I headed off and put myself under the running water. I had shaved that morning, but ran the razor over everything one more time. I used the gel Monica gave me and it smelt lovely. Oh, and I tugged myself to completion thinking of Monica's brief but quite wonderful show.

I got out and wrapped the towel around myself the way Monica had done and walked out into my room. Monica was at the mirror in her underwear, putting the finishing touches to her make up. She looked at me in the mirror and smiled again. She had on a lacy black bra which pushed up her boobs, black lace panties and a garter belt and some stockings. Her heels lay next to her, black, shiny and ever so sexy.

"Aw Jennifer, that is so cute. You wanted to look like me. It's like having a little sister."

"Monica, you're not helping" I said looking down to another growing erection.

"Jesus. You are one horny fucking girl. We're going to have to tape that thing down."

"I have underwear that will help. It's called a gaffe and I can tuck my penis away."

"Good. I would think the other two girls who are helping me tonight are way hotter than me. If we can avoid the hard-ons making a little tent in your dress, then that would be good. Or should I say, a big tent. You're not a little girl are you, Jennifer?" She giggled which only made me harder.

"Get your undies on please. Black like me. The dress is a boat neck so.... "

"I know what a boat neck is."

"Of course you do. Sorry. I'll stop treating you like Pete and start treating you like my little sister, Jennifer. In fact, If I have to introduce you tonight, that's exactly what I'll say. Same dad, different Mom".

I stiffened again. "Monica, my undies are in here so would you mind giving me the room so I can at least get partially dressed?"

"No"

"No?"

"No. I've still got to get my make up finished and we're running a little bit behind. You don't have anything I haven't seen before, so go ahead and get dressed."

"But....."

"Jennifer. You are now officially on the clock as one of Monica's Maids. Do as the boss tells you. Get dressed while I finish my make up."

I swallowed hard and tried to sarcastically curtsey. "Yes Miss" I said. But apparently it didn't look sarcastic. It looked cute.

"Ooooh, I like that. Miss. Mmm. Get dressed."

I'd laid my undies out on the bed. I had a body shaper which pulled in my waist and let me tuck away my penis. It had pockets for the breast forms, which were a C Cup. And padding on the hips and butt. It had been expensive but worth it. But first I put on my garter belt and rolled my stockings slowly up my smooth, slightly tanned legs. It had the usual effect. I looked over to Monica who saw my growing erection in the mirror and smiled. "Remember to tuck it away Jen." I liked that she called me Jen. It was familiar and nice. And so, I grabbed my all in one and slipped it on, tucking my dick away and pulling the straps over my shoulders. It gave me a good shape. And much more importantly, it gave me a smooth front. I slipped my breast forms in place, making sure they were snug against my chest.

"There. Done" said Monica putting down her lipstick. "Let me see" she said, easing off the chair in front of the mirror and standing all in one fluid, liquid movement. "Mmm terrific" she said and she straightened a bra strap which had twisted. It was such a simple thing to do, the sort of thing one girl would automatically do for another but in its simplicity, it was erotic and sexy and so accepting. Ridiculously, I felt tears in my eyes.

"Aww Jennifer. I'm sorry. I thought this would work but if it makes you cry, then let's just stop now. We'll manage with three. It'll be a struggle but we'll manage. I don't want to stress you out."

I swallowed and shook my head. "No. No. I'm fine. It's just.... apart from my Mom, no-one has been so accepting and understanding and I just got a bit emotional. I'll be honest. I am terrified. But I am also excited and turned on and I don't want to let you down. I couldn't handle disappointing you. Jennifer is going to do this."

"Good girl. Now let's get your make up done and get you dressed."

I put on the beard cover I used. She watched as I smoothed and blended. "Impressive" she said then started putting her make up on me, working quickly and rhythmically, turning my head and asking to close eyes, or pout or turn a certain way. The make-up felt cool on my face and for the first time in about two days, I started to feel a little bit calmer and content.

"Ok Jennifer. You can take a look."

I opened my eyes. I looked amazing. I mean, I'm pretty good at my make up, but this was another level. I loved it. She had gone with a couple of purple shades on my eyes, given me almost matching lipstick and fake eyelashes which made my brown eyes pop. I couldn't help myself. "Fuck. I look amazing."

She dropped her face next to mine. "See - we look the same. Actually Jen, you could pass as my sister. The other girls have been asked to do the same look. It's an image thing. You know - like the Addicted to Love video from the eighties."

"The dresses aren't that short are they."

"Such a girl. Wanting to see the dress. Right. What normally comes first. The dress or the hair?"

"Normally the dress, but let's do the hair and shoes first".

I grabbed a long blonde curly wig. I brushed it out and then gently placed it on my head. I worked it around and styled it at the front, then following Monica's instructions, I pulled it together and brushed it in to the ponytail she wanted all her girls to wear this evening. I struggled a bit but with Monica's help, it fell into place. It looked wonderful and felt very young and sexy. I grabbed my heels. My ex-finance's three-inch black heels and slipped them on. They made my legs looked long and lovely.

"Right - want to see what we're all wearing?"

Of course I did. I was excited and intrigued but luckily the gaffe in my body shaper continued to do its job in the most trying of circumstances.

Monica opened the garment bag and pulled out matching faux leather dresses. They were excellent quality, buttery soft and ever so shiny. They were - very simply - elegant but super sexy. "Zip me in then I'll do you Jen."

Monica slipped into her dressed and wiggled it over her hips. She put her arms through the sleeves and pulled the dress up. She lifted her ponytail and turned her back to me. God, I wanted to grab her right there and throw her on the bed, lifting her dress up over her glorious thighs. It took everything I had to simply grab the zipper and ease it up until it closed. She turned and looked stunning.

"Right. You." I copied her. The dress felt delightful and I eased it over the pads on my hips and thoughts concealed by the body shaper and pulled it over my boobs. I lifted the ponytail, the way Monica had and turned to face her. There is something deeply erotic about a woman zipping you in to a beautiful outfit.

I turned to face Monica. A huge smile broke across her face. "My god, you look amazing Jennifer. Honestly. Just wonderful. This has turned out much better than I ever expected and you're certainly prettier than one of the other girls. It's amazing."

We turned to face the mirror and if I'm honest I was staggered at how cute and sexy I looked. The dress was beautiful. And we did look like sisters. Monica handed me a silver bracelet that looked like hers, and a little women's watch which was dainty and elegant. She also gave me a ring which she placed on my engagement finger. "You look so good; this gives you a little protection."

She saw what she said worried me. "I didn't mean to scare you. It's nothing to panic about. This is a classy event, but you look so hot someone will try and hit on you. It's what happens to hot girls. Get used to it." I blushed furiously. I didn't want to ask what she meant by "get used to it". "Yeah, that makes you look less cute," Monica laughed.

"Ok baby, grab a coat and let's get going. We have a busy night ahead". She smacked my butt, smiled and wiggled in front of me. I swallowed hard. This was a test. A huge test. I was nervous, excited and turned on. And so, I stepped one high heeled foot in front of the other and headed out.