Maid In The Shade

Author's Note: This is a sequel to "Clothes (Re)make The Man". It isn't necessary to read that story first but you might enjoy this one more if you do.

"Wendy, I'm ho-ome!" I put on my best Jack Torrance evil grin.

"Oh, hello, Lee," said Danielle, not looking away from the TV. "How was your day?"

"Damn, you're no fun, Dani."

"Lee, you use that gag about every other Friday after your payday beer swilling with Greg and Dwayne." I had to admit, it was my favorite entrance joke. Maybe I use it a little too often and should should give it a rest. After all, it was a quote from a movie about a guy trying to kill his wife.

"No need to make dinner, Honey, I had buffalo wings at the bar," I called as I hung up my coat.

"Wasn't going to, Lee. It's eight thirty anyway."

I hopped over the back of the couch and sat down next to Dani. "Whatcha watching?"

"RuPaul's Drag Race," said Danielle.

"Oh."

"You should watch it with me. Maybe you'd get some pointers about style." Dani liked to needle me lightheartedly about my enjoyment of wearing panties and a dress around the house. It was just a way for me to get comfortable while lounging around. She was fine with it; She even thought it showed I'm not just a total steak-eating, football-watching macho auto mechanic.

"In answer to your question, my day was okay. Mrs. Sanderford brought her car in for the third time in six months because of a tiny rattling noise. I swear, that woman thinks of that Acura as her child."

"Money in the bank, Lee."

"Yup. And how was your day, Dani?" Danielle was an accountant for Trenton Realty. She actually made more money than I did, though not as much as I thought she should, given how much money the realtors themselves pulled down.

"It had its moments. Louise, Dave Trenton's wife, was in. We chatted and she invited me to join her book group." Dani had been reading more lately, since I had magnanimously been volunteering to do laundry and other chores. That had freed up her time.

"They're currently reading "The Paris Novel" by Ruth Reichl. I hear it's about food, one of your favorite subjects."

"Sounds like 'chick lit' to me. I'll pass."

I took myself off to the shower. Not only did I smell like grease and oil from the garage, but I knew I had beer breath from the bar. After I got reasonably clean I slipped on my loose cotton dress and women's panties. (Don't get the wrong idea. I'm still 100 percent dude; women's clothes are just so comfortable. Lucky women!)

I rejoined Dani on the couch. The Drag Race was still going. I don't have anything against men dressing in women's clothes, obviously, but the whole drag queen thing didn't interest me.

I watched the show for a while and then said to Dani, "I should go on that show. I bet they make a lot of money." Dani grunted. "Lee, they may get big prize money if they win but they spend so much on their makeup and costumes that they probably don't come away with much."

Then she smirked and told me, "But, hey, if you want to become a drag queen, go for it." The idea of me dressing like RuPaul seemed to amuse her.

"Well, I could never compete at that level, but I could easily pass for female. I already have a dress, and my hair is shoulder-length, so just add lipstick and eye shadow. Ta-da, instant girl!"

"Right. Your voice alone would give you away. And have you considered that you'd have to shave your legs and armpits? Not to mention, the way you clomp around the house wouldn't work. You'd have to walk less like a rhinoceros."

"I still say I could definitely do it if I really wanted to. Anyway, that'll never happen. Not interested."

A couple of weeks went by. One evening I was sitting at the kitchen table with my laptop, wearing my favorite of the two dresses I owned, reading about the upcoming NFL season and wondering if I should join a fantasy football team, when Danielle came home from her book club.

"Hi, Honey. Guess what?"

"Uh, you got a raise? You got fired? We won the lottery? You're pregnant? You totaled the car? You bought a cat? You bought a rat? We're moving to Japan?"

"Ha. Ha. Ha." Dani walked up behind me and put her arms around me. "No, Mister Comedian, none of the above. Louise asked me to host the book group next month." She leaned down and kissed my cheek.

Twisting around in my chair, I pulled her in for a proper kiss. "Congratulations, Darling. Tell me what night that'll be so I can make plans to go bowling with the boys."

"Oh, no you don't, Lee. I'm gonna need help buying food, cleaning the house and serving the guests."

I groaned. "The house looks fine as it is, Dani. Just get some pizzas and beer. I'll even pay the pizza guy and set out the paper plates."

Dani walked around in front of me and closed my laptop. I started to protest but thought better of it.

"Lee, Louise Trenton is my boss's wife, and the other women in the group are on that same social level. Which is at least one level above us. I hope to join them one day on that level in the real estate field, so I want to make a good impression."

"Okay, Sweetheart. I guess a couple hours of housework won't kill me, if it's that important to you."

Dani kissed my forehead. "Thanks for understanding, Lee," she said, smiling.

Just then I got a bright idea. "Hey, Dani! Let's hire a maid or a catering service. Then you can impress the ladies and I can go bowling with Dwayne."

"I should have known you'd try to weasel out."

"I'm not weaseling. I'm just trying to be practical."

"Spending hundreds of dollars we don't have isn't 'being practical', Lee. That's what a catering service would cost."

Then she got this sly smile on her face and I got worried. "Say, Lee. You've given me an idea. I know where we can get a maid for free."

"Where's that, Darling?"

"I'm looking at her. Or him. You remember how you bragged you could pass as female? Well, here's your chance."

"Whoa, back up a minute," I exclaimed. "Sure, I said something like that, but I didn't say I want to actually do it!"

"Buck buck buck bu-gaw!" Dani imitated a chicken flapping its wings. "I suspected that was just talk."

"Dammit, I could pass as female." I rolled my eyes. "Anyway, you'd get free maid service but what would I get out of it?"

"Say 'yes' and I can think of an immediate reward you're sure to enjoy," she whispered, sliding her hand up my thigh.

I knew I was being lulled into committing to her plan, but being lulled seemed like a good idea, so I didn't resist. Dani leaned over and began kissing me while her hand slipped under my dress and caressed my cock through my panties. I was immediately hard as a rock. She patted my thigh to indicate I should swivel my chair away from the table.

Dani knelt between my legs, pushed my dress up around my waist and slid my panties down my thighs.Then she leaned and took my cock in her mouth. She twirled her tongue around the head before taking more in, then began very slowly easing my cock deeper. As she bobbed her head more rapidly, my dress slid down to partially cover her. Even though I greatly enjoy seeing my cock in her mouth, I must say that the sight of my dress covering Dani's head was really erotic. I didn't have long to enjoy that sight because soon I erupted into Dani's throat. I came so hard I almost overturned the chair.

After my dick wilted, Danielle let it fall from her mouth. Smiling up at me she said, "I wonder what size maid's uniform you wear?"

Later, after I had my brain back, I began to think. Much as I appreciated getting head, that alone didn't seem enough for all the work I would have to put in to be Dani's maid.

"Say, Dani, why do I need to be in drag as a maid? Why can't I just help out as me?"

"Because I'm trying to make an impression on Louise and her crowd. Having my hubby help serve drinks would seem like I'm not trying very hard." She took a deep breath and said, "Look, I know it's asking a lot and, yes, I'm aware it's pretentious, but it would really help if you could bring yourself to do it.

"And, besides, I really want to see you all dressed up as a maid. I was not sure about the whole crossdressing thing at first but now it seems like it could be fun."

"Well, fun for you, Dani," I exclaimed. "I'm just going to need a little extra inducement to go through with this."

Danielle was quiet for a few minutes. Then she walked over to me and said, "How about we make a contest out of it? If you go through all this, pass as a woman and pull off the maid duties, you get to buy season tickets to the NFL games. If you renege on your promise, are found out by the women, or knock over the food table, I get to go to Paris!"

"Wow! That's really upping the ante there, Dani. I'm absolutely interested in the football tickets but where did you get the idea of going to Paris?"

"From this book I'm reading for the book group. The protagonist goes to Paris, and it has me thinking I'd like to see it."

"Both those things are really expensive, Honey," I said. "Maybe we should put a limit on how much we spend. How does a thousand dollars sound?"

Dani looked up at the ceiling for a minute and then said, "You're on!"

It was easy to find suitable maid's uniforms online but getting the size right was tricky. I finally settled on a blue short-sleeve dress with buttons all the way down the front. I ordered the largest, XXL, and hoped it would fit. In case I haven't mentioned it before, I'm not a huge hulking guy. Although I used to be really overweight, I'd been exercising and cutting down on the beer, so I wasn't horribly paunchy anymore.

At first I thought I could get away with wearing the sports bra I already had with balled-up socks stuffed in it, but experiments with walking around that way showed me that the socks were apt to fall out when I bent over. Since I was convinced I was going to win the thousand bucks, I figured shelling out for a pocket bra and silicone breast forms was going to pay off in the long run. The bra and breasts were B cups; I thought I ought to be conservative, since I wasn't going on RuPaul's show.

The clothing arrived. To my relief, the dress fit okay. The material was some synthetic blend meant to be useful rather than fashionable, but I could live with it. I tried on the bra with the silicone forms inserted. I kind of liked the feel of the mounds bouncing around under the dress. It reminded me of back when I had moobs, only these I could take off.

I didn't try wearing the maid uniform and also imitating a woman at the same time. First I walked around like my normal self wearing the dress, bra and panties. I thought maids probably wore sensible shoes so I just used a pair of black running shoes.

I was walking around en femme, as I learned it was called from reading crossdressing blogs. I came into the kitchen where Dani was making lunch. (I had asked her for advice about how to behave like a woman but she declined to help. "I'm on the other team, you know," she said. "You made the bet so it's up to you to figure out how to pass.")

I had to take a leak so I headed to the bathroom. Popping the toilet seat up, I lifted my dress and pulled down my panties. Unlike the comfortable dress I wore for watching football, this one was stiff and tight. I had trouble holding the dress up and the panties down while also pointing my wang toward the toilet bowl. I managed, although I almost fell into the tub, and I accidentally pissed on the rim of the toilet a little bit. I quickly wiped that off with toilet paper. No harm done, and Danielle doesn't have to know I did that, I thought.

After I was done, I came back into the kitchen to join Danielle for lunch. "Boy, it ain't easy pissing when you are wearing a dress," I remarked to Dani.

"You have to sit down to pee," she said.

"What?"

"Lee, you dress like a woman, you pee like a woman."

That had not occurred to me before. Somehow wearing women's clothes didn't seem to challenge my manhood but, sitting down to piss? What if someone saw me? My old paranoia was back. There was no way somebody would walk into the bathroom while I was doing my business, but it still made me nervous. Standing to piss is one of the defining guy behaviors. It was going to be hard to get used to the idea. At least this would only happen a few times while I was pretending to be a maid. Then I'd be done with it forever.

Next on my list was learning to walk and talk like a woman. Since Danielle wasn't going to help me and I didn't know any crossdressers (although possibly I did but they hadn't revealed their inner selves to me) I turned to the good ol' Internet.

I had read some blogs about crossdressing when I got my first pair of panties, just to be reassured that what I was doing wasn't that far out, but I hadn't really studied the techniques. Unfortunately, there wasn't an equivalent to the sites telling you how to repair disc brakes, with step-by-step instructions and diagrams. One site would say 'take shorter steps' but another would say 'taking shorter steps is a rookie mistake'; 'swing your arms', 'don't swing your arms'. There seemed to be a consensus on 'lead with your hips' but that made me feel like a character from a 1930s cartoon. I tried walking with my feet in a straight line but I lost my balance and knocked one of Dani's favorite vases off the shelf and broke it. Dani wasn't amused by my explanation.

One day at work I was finishing an oil change for Mrs. Sanderford's Acura when Greg came into the garage and told me that he and Dwayne were going to the junkyard to look for a driver's side door for a 1991 Ford Bronco.

"A '91 Bronco? How many days will you be gone, and did you pack your camping gear?" I joked. Greg and Dwayne chuckled, but their hearts weren't in it.

They roared off and left me on my own. It was a slack time and I'd finished the last job. All that was left was cleaning up and waiting to check any customers out when they came to pick up their cars. I got out my phone and used Bluetooth to connect to the shop sound system. Soon, Lux AEterna by Metallica was blasting from the speakers. I did some headbanging as I swept the garage floor.

As I listened to my playlist my thoughts turned to the upcoming maid impersonation. I wasn't making much headway on solving how I would present myself so that I'd pass with a group of women. I started trying out various walks around the garage. I saw a 15" hubcap in the corner and picked it up to use as a pretend serving tray. Balancing it on one hand, I used the other hand to pick up various objects like coffee cups that were on the counter, placing them on the upturned hubcap and walking in what I thought was a womanly fashion, nodding as if there were ladies sitting on couches. I leaned over, offering pretend glasses of wine and then walking around putting one foot in line with the other, trying to lead with my hips.

I had my back to the door and the music was pretty loud, so when I heard "Hello?" behind me, I lurched and dropped the hubcap as I spun around to see who had spoken.

There stood Mrs. Sanderford. "Training to be a mime?" she asked.

I hit mute on my phone. "No, Ma'am. Just clowning around."

"You had a very serious look on your face for a clown, Lee. I suspect there's more to it."

Fuck. Mrs. Sanderford was our best customer. If she thought I was losing my mind and took her trade to another garage, it would be an economic blow to the shop. I threw myself on her mercy.

"Mrs. Sanderford, I'm really sorry about this. I am all business when I work on your car, I swear. Sometimes I just get carried away."

She smiled. "Lee, I know you're a good mechanic. If I didn't think you and Dwayne were top notch, I wouldn't bring Bertha here for service." That was the first time I knew that she had a pet name for her car. It figured.

"You know something, Lee? I was a theater major in college. I've directed plays for community theaters, too, so what you were doing is no big deal to me. In fact, it makes me nostalgic for acting class. Out of curiosity, what role were you acting out?"

"Well, I..uh..I was pretending to be a maid serving drinks at a cocktail party."

"Any particular reason for that specific fantasy?"

I was thinking furiously. Maybe if I explained a little bit of it to her, she would be sympathetic enough not to mention my behavior to Greg. If she did say something, he might think it amusing, but I'd probably be stuck with a nickname like "Hazel" forever.

"Okay, this will sound weird, but I made a bet with my wife that I could pass as a maid for her book club gathering. There's a thousand bucks at stake. I was trying to imagine myself handing out snacks and wine."

Mrs. Sanderford threw back her head and laughed heartily. "That's so great! And here I thought you were the kind of guy who wouldn't be caught dead behaving as anything other than a clone of Vin Diesel, or rather Dominic Toretto."

"Well, I would sure like to own Dom's Charger, but that's about as far as my imitating him goes."

"If you don't mind my saying so, you didn't look very womanly there," she said. "How is getting into your role going?"

I grimaced. "Not great. I'm trying to figure it out by watching YouTube."

"That's no good," she said. "You need to watch some actual women and see how they move. Your wife, for one. Of course, if you stare at a woman on the street, you're liable to get punched out. Watch some movies that feature women in prominent roles and study their actions."

"That sounds like good advice. Any particular movie come to mind?"

She thought for a minute. "Ever hear of 'Some Like It Hot'"?

"Is that on Porntube?"

Her eyes narrowed and she scowled at me. Then her face cleared and she laughed. "Oh, what a joker. You had me going; I thought for a minute you were serious." Actually, I was. I had no idea what she was talking about.

"I tell you what, Lee. Give me your email address and I'll send you a movie list and some advice about crossdressing. Crossdressing has a long history in the theater, you know."

I gave her my address and sent her off in Bertha, with a five percent discount on the oil change, in gratitude.

When Greg and Dwayne finally got back to the shop (without the door they were looking for), I told them I'd taken payment from Mrs. Sanderford. Greg looked at the receipt. "You gave her five percent off? You're pretty generous with my money."

"Hey, we make more from her than our three next best customers," I said in defense. Greg shrugged and let it go. I felt I'd dodged two bullets that day.

That evening I got email from Mrs. S. She had a list of movies for me to watch. Besides 'Some Like It Hot', which turned out to not be a porn film, there was 'Carol' about some lesbians, and a few more. Since Mrs. Sanderford was at least 70 years old, they tended to be really old stuff. There was 'Waitress' from 2007, which wasn't very old but altogether too sweet for my taste, and it wasn't the pies I'm talking about. 'Thelma And Louise' I had watched with Dani, at her insistence. That had enough action in it to hold my attention, but I got the feeling Dani was trying to tell me something.

I looked up how to stream these films and invited Dani to watch with me. She was delighted to join me, since I had almost always declined to watch her chick flicks, and she didn't like my taste in ultra-violence.

Some of the films, like 'Carol', were surprisingly good. At the end of that movie, I felt a tear come to my eye and I had to pretend to choke on a peanut to cover up. But the real hit was 'Some Like It Hot', about two guys who have to pass as girls to escape some mobsters. It was hilarious, and it had Marilyn Monroe in it. The ending of that film cracked me up, and I chuckled for days whenever I thought of the final lines: "But, I'm a guy!" "Nobody's perfect."