Playing the Maid

Improvements

Emma started playing dress-up at least a little each day. Afterward, she'd do her makeup and come down and hangout in whatever fancy costume she'd tried on. There was a lot of variation in the clothes; although, the most common theme was a sort of faux 1800s style that was a little less, how shall I put this, modest.

We worked in the city on Wednesdays and Thursdays and spent the rest of the week telecommuting. Emma was most excited about playing dress-up on Thursday evenings, as soon as we got home. One week, she grabbed me by the arm and pulled me up to the attic.

"This will just take a second. I want to try something... again," she spoke quickly trying to hide her excitement.

"Me in a dress?"

"Well yes, but just for a second. I've just been thinking about how you looked and wanted to try something."

"What did you have in mind?" I asked, rolling my eyes.

"It's just that you didn't fill out that dress quite right. I wanted to give it another try, with some improvements."

"Improvements?"

Emma held up a bra that was black and lacy. She fitted it around my chest, filling the cups with bags of birdseed to give them the weight of real breasts and fidgeted with the bra straps until they hung right.

She slipped the dress over my torso and had me step into a pair of plain black mary-jane shoes.

"See how it just hangs better?" She said, gazing at me through the mirror.

"Yeah, but it's weird to see myself with boobs. I guess it does make the dress look better."

"And the heels give your legs a nice shape."

"It kind of looks like someone photo-shopped my head onto a different body."

"Here, let's try a different dress." She helped me put on the red western dress she'd initially tried on herself. It was lower cut so that some of the bra was showing, though it wasn't obvious. It was a shorter dress, and we could see my legs.

"Looks funny with hairy legs," I said.

"Yeah, why not go shave them?" Emma asked with a slyly lifted brow.

"This is starting to get weird."

"Well, that's what makes it fun... I'll help."

The house had an old-style cast iron bath tub. It was large and stood on four legs. Emma slid into it with me and helped me shave my legs. I was about to get out, but she nudged me back in and shaved off the rest of my body hair explaining, "Why not? Let's just get it all done at once."

We went back to the bedroom, and I tried on the dress again.

"Now you look sexy." She remarked playfully, ogling her eyes at me, "God! look at those legs."

"They feel a little itchy."

"Oh yeah, I have lotion for that." Emma knelt beside me and proceeded to rub moisturizer onto my legs. She had to reach up under my skirt to do so, and when she got to my inner thighs we were both breathing heavily. She coaxed me onto the bed, and we made love with Emma on top, and me still in the dress. I dozed off afterwards only to be woken up by Emma's gentle nudging.

"What did you think of that?" she asked.

"Why do you like me in a skirt so much?"

"I don't know, it's something new. It's fun to play with you as my dress up doll."

"You're turning me into your own personal transvestite aren't you?"

"Well, you seem to like it. It's not like it's a lifestyle thing. Just something to try. Not like anyone will see you out here is it? I'm sure we'll get tired of it eventually and move on, but you know what they say about regret?" Emma started playing with the edge of my skirt.

"It comes with lace?"

She ran her hands along my legs and softly tickled my toes. "You regret what you don't do, not what you do. What's the worst that could happen?"

"You could like it."

"Don't you mean... you could?" she asked.

We made love again, and I fell asleep in the dress until morning.