Monica and I eased in to a simple routine. She would show up on Wednesdays. We’d talk over coffee for ten minutes, catching up on news. She’d get the cleaning kit and start and I would head off to my office to continue working on my latest book. She’d come tell me when she was done, we’d chat for maybe five more minutes. I’d read her parts of the book I’d been working on. She’d had thoughts and suggestions which I’d sometime incorporate. We’d laugh. I’d pay her. She’d leave. And I would wank furiously while thinking of her.
I really liked her.
I got to know more about her. She’d split with her boyfriend. Like me she had no family nearby. She’d like to have a comfortable life, earn more money, help her family, drive a better car. All the usual stuff.
One Wednesday, I was working in my office, putting the finishing touches on to my third novel when she knocked on the door to the office.
“Peter, I am so sorry to interrupt you. Do you have a second?”
I welcomed her in “What can I do for you?”
“You remember the conversation we had a couple of weeks ago about what I wear when cleaning?”
“Ahhhh…sure. You said you got very hot and I joked that maybe you needed a uniform.”
“And I said only if you were going to pay for it.”
I laughed.
Her face lost its smile. “Is this what you meant?” And from behind her back she produced a short, satin maid’s dress. “Because if this is what you meant, I think we’re done her. This is so demeaning? I thought we were friends; you see me as some sort of object. A cartoon?”
“No, no, not at all — that’s not what it is, at all.”
“I find that hard to believe to be honest.”
“How did you find it?”
“I was tidying up in the closet and it was lying on the floor. I’m not wearing this. You can forget that.”
“It’s not for you, honest Monica.”
Well, I know from what you tell me that since you split from your fiancé, I’m the only woman who has been here — so it’s not for anyone……..” Her words trailed away, the word else was swallowed. The sudden realization hit her. Her hand went to her mouth. I dropped my head.
“This is yours. You wear this. This is your maid’s outfit.”
I nodded. My head still drooped in shame and embarrassment and my cock hardening through shame and embarrassment.
“What’s going on Peter? I’m not sure I understand.”
“It’s a long story.” And I decided to tell her everything. From the wedding dress and my dressing at home to the moment I got caught by Ellie.”
“I decided I was done with cross dressing but the conversation about uniforms sparked something inside me and I started looking at some stuff on line. That led to a few purchases and you found one of them on the floor”.
“I want to see.”
“What? That isn’t a good idea for either of us.”
“I want to see. I want you to go and put this on and show me. Did you buy anything else? Heels? Stockings? A wig?”
“I did. But I actually haven’t dressed in any of them. I was scared I’d re-open too many feelings which have kinda screwed me over.”
“You need to show me or I’m leaving and we’re done here.”
I could get other cleaners. Shit I get three business cards through the door a week for cleaners that a less expensive than Monica. But I liked her. A lot. And not just because she was beautiful and sexy and funny and smart.
“Monica. It’s…….”
She threw the maid’s outfit at me.
“Pick that up — head off to the bedroom and come back dressed. Or we’re done and I’ll never speak to you again.”
I was aware of the irony here. One woman kicked me out of her life because I dressed. Now one was threatening to kick me out of her life if I didn’t.
I picked up the uniform. It was so soft and lovely and I headed to my bedroom to do as she asked.
My stomach was churning. I had no idea how she would react. My heart was racing and I have to admit I was excited. I pulled out a corset, a black bra and some breast forms. I found some satin panties and my black hold up, lace top stockings and the Ellie’s three-inch heels that came with me. I pulled out a wig I brought with me from Mom’s and a make up kit. I started putting things together.
Monica banged on the door. “Hey I’m waiting.”
“I’m sorry. It takes a moment.”
“I don’t need a fashion show, just get out here.”
“Two minutes, please.”
“It better be worth it princess.”
My heart flipped when she called me that.
I decided to forgo a squirt of perfume. I plumped up my boobs — rubbed lip gloss across my pink lips and looked in the mirror. I did look good. Even in a rush I was passable.
“Ok, I’m coming out. Please promise you won’t laugh.”
“No promises, princess. Just get out here.”
I opened the door and stepped out. Monica had her back to me and turned. I heard her gasp. Her hand once again shot to her mouth. She stood silently. Her hands on her hips, her face framed beautifully by a few strands of loose hair. God, she was really gorgeous.
She walked towards me and then slowly walked around me. I stood shivering with nerves and anticipation. Once back at the front, she closely examined my makeup. She stepped back.
She opened her mouth but seemed to forget what she was going to say.
The silence was oppressive.
“So?” I asked
“This” she said wagging her index finger up and down “is impressive. You look like a girl. You have legs like a girl. Shit, you even have boobs like a girl.”
I couldn’t think of a reply. I just stood there, frightened, embarrassed and willing my cock not to get hard.
“Let me see what’s underneath?”
“What do you mean?”
“It’s pretty simple princess, pull up your dress, I want to see what you have under your uniform”.
I had now been caught three times — and each time the woman wanted to know what undies I was wearing. The uniform came to mid-thigh. I lifted the lacy hem of the soft silky dress up and up over my waist. I stood there — at attention and presented myself to Monica.
“Silky panties, expensive stockings, a corset and those high heels are not thrift shop are they? Everything you’re wearing costs. And you have better makeup than me. Matching bra I presume?”
I nodded. Not quite knowing what to say next.
“And what’s the deal? You dress up, pose in front of the mirror and run around the house until you get tired, or bored or the heels become sore and then whack off to the idea until you get the urge again?”
“I’ve actually only tried this on once. When it arrived. And I wasn’t fully dressed.”
“Fully dressed? That’s what you call it when you get all your gear on?”
“This is the first time I’ve fully dressed since I got here. I honestly haven’t done it since the day Ellie caught me.”
“Are those her shoes?”
“Yes.”
“Does that do something for you. An extra thrill, a little buzz.”
“Actually, no. It was convenient to have them but they are a little tight.”
“I told you just to put the dress on. You did the rest. The undies and the wig and the make up and what I’m guessing are some fake boobs. Nice tits by the way.”
“I guess it comes from when my mom caught me. If you’re going to do it, do it properly.”
“Well, you certainly did that princess.”
“It’s Jennifer.”
“What.”
“When I’m dressed, it’s Jennifer. My mom picked out the name thinking I was going to be girl. I like the name and when I started dressing, it’s what I decided to call myself.”
“Oh, that’s precious. Well Miss Jennifer, I have to get to my next client.”
I don’t know why but I suddenly burst into tears. There was just so much emotion, so much history, so much of everything and the floodgates opened. I folded in half, the sobs wracking my body.
Monica, walked over, and took my hand pulling me up. In our heels we were about the same size.
“Look, this is a little odd. Certainly not something I’m used to — but it’s nothing awful either. No one’s been hurt, no-one’s died. I just need a little time to process this. You don’t need to be so upset. I do have to go.”
She hugged me. Our boobs pushing together. I was willing my cock to stay tucked. That could ruin everything.
“Look, let me think this through. I like coming here and I’m not going to stop because you decided you’d like to dress as a French Maid. I’ve come across all sorts in this job — so have the other girls who work for me. Let’s give this a little time.” She pecked me on the cheek.
“I’ll be in touch. Jennifer.” And don’t worry.
She smiled, grabbed her coat and walked out of my apartment, heading for her next job.
I eventually got undressed and got back to work. After I had a big wank over what had happened and as my imagination ran riot about what could happen next.