by John Dylena
I finished my business and showered. My body hair hadn’t started growing back yet, so I didn’t need to shave again. I dried off and went back into her closet to get dressed. This time, I’ll need a different color, I thought.
Browsing through the underwear, I found something special: a black corset. Excited, I put it on and fastened the clips in the back. It was tight, but now I had a more defined, hourglass shape befitting a woman. I slid on a pair of matching black panties, followed by a pair of sheer stockings and attached them to the garters. To complete the look, I stuffed the bra cups with socks.
Satisfied, I looked through her outfits. I found a black pencil skirt and slipped it up over my body. It ended several inches above my knee, but was not too revealing. I put on a white blouse, almost similar to the one Janet had on. It had a V-shaped neckline that showed some of my “cleavage,” and the sleeves stopped at the elbow.
I put on a pair of five-inch black patent heels and headed into the vanity with the wig. I sat down at the chair and did my makeup again. This time it was a little more modest, with nice ruby red lipstick. I combed the wig and slid it on.
I definitely look better, and hotter, than I did last night… but something’s still missing…
I searched through the drawers for accessories and put on a pair of gold clip-on earrings, a chain necklace, rings, bracelets, a feminine watch, and topped it all off with a few sprays of perfume. Lastly, I filed my nails down and attached a set of acrylic press-ons, which were a shade that was similar to my lipstick and slightly longer than my normal nails, giving them a strong, feminine appearance.
Satisfied, I stood up, straightened out my skirt, and headed downstairs for breakfast. I made myself some food and a cup of coffee, sat down as my computer, and began typing away, my fingernails clicking against the keys with every stroke.
After several hours, I rolled back from the desk. In all that time, I had only been getting up to use the bathroom, which after drinking several cups of coffee was pretty often. It didn’t take long for me to notice that sometime during the typing session, I started sitting cross-legged like a woman normally does.
I would also stand up to stretch my legs occasionally, and in the process, straighten out my skirt. I was surprised at the fact that my feet had not been bothering me from the heels, and that the outfit was surprisingly comfortable. I would get up to refill my cup, and walking in the heels almost came naturally. At first, it scared me a little that I was able to walk so gracefully in them, but I got over it pretty quickly and got back to work.
“Okay, it’s six-o'-clock. I'm calling it a day,” I said to myself. I stretched out my limbs then sat back down. I wrapped up what I was working on and shut down my computer. I got up and went back into the room and laid out across the bed, exhausted.
Crap! I’ve worn these clothes for the majority of the day. They probably have my scent all over them. Gonna need to wash them to hide it, I thought, stripping down.
After removing the skirt and blouse, my stomach began to rumble. Hmm, I think tonight, I'm gonna cook up something fancy… Of course, that means fancy dinner wear, too!
I kicked off the heels and removed the stockings, skirt, and blouse, put them away, and slid on a pair of darker stockings. I went into the closet, pulled out a black evening dress, and put it on. Then I grabbed a pair of knee-high, heeled black leather boots. I slid them on, tidied up my makeup, and then went back downstairs and cooked the fancy meal: a slab of rib-eye steak, mashed potatoes, green beans, and a glass of wine.
Damn, I thought. I feel like a friggin’ housewife cooking a meal for my business-type husband!
I sat down at the table and ate. After the meal, as well as several glasses of wine, I retired to the couch and watched a pay-per-view movie. When it was over, I changed out of the clothes and put them away. Then I removed the makeup and wig and went to bed.
Gotta remember to remove these nails before Ms. Stevenson gets back, I thought as I fell asleep.
The morning sun shone brightly into the room as I awakened the next day.
Damn, another good night’s sleep and I have to get out of this bed, I thought to myself said. Fortunately, I finished most of my work yesterday. I don’t think I’ve ever typed that fast and with so few errors before – must’ve been that secretary get-up.
I rolled back over and fell back asleep, waking up some time before noon. I got out and showered and headed downstairs for breakfast.
The day was well spent. It was beautiful outside, and I met up with friends to hang out at the beach. When I came back to Ms. Stevenson’s, I made sure to brush off all the sand before stepping into her house.
What a day, I thought. There sure were some hotties out and about. Oh well, time to try on another outfit.
I stripped, showered and returned to the closet. I clipped on a baby blue bra and a matching pair of panties, then put on a pair white stockings.
The slutty schoolgirl.
I stepped into a plaid miniskirt. This one was pretty revealing, barely covering my thighs. Then I stuffed my bra and put on a thin, white, long-sleeved sweater. Since it was summer, I cranked the A/C so I would be more comfortable.
For shoes, I put on a pair of black leather heels with an ankle strap. I put on some makeup and the wig and retired to the couch to watch some TV. It was getting late when I saw it: on the TV was a hot blonde in a very sexy cocktail dress.
Oh yes, that is nice, not to mention I am craving a nice mixed drink right about now.
I went back upstairs and put the outfit away. Then I looked through Janet’s collection of “sexy dresses” and found the one I was looking for. It was a sleeveless green cocktail dress. But this one was not something that I could wear a bra underneath.
Huh… Well, she’s gotta have breast forms somewhere.
I looked though all the drawers and searched high and low for them, eventually finding what I was looking for.
I pulled on some panties and put on the dress. It was tight-fitting, but not too tight. I inserted the breast forms in and they actually gave me nice cleavage. I put on a pair of green strappy sandals and headed downstairs to the bar.
Wow, this is the first time I've gone without stockings, I thought. And damn, I’ve got nice legs!
I walked up to the bar and made myself a mixed drink, then sat back down on the couch and watched some more TV, occasionally getting up to mix myself another drink. After a while, I was getting pretty drunk, so I decided to call it a night. I changed out of the pretty cocktail dress and went to bed.
Ugh, what a weird dream, I thought as I awoke, scratching my head. That was the first time I think I've ever had a dream from the point of view of a woman.
I had dreamed that I was, in fact, a woman. In this dream, however, I wore the cocktail
Well, today is the fourth day of my house-sitting; Ms. Stevenson returns in two days. Huh, I just realized that other than the schoolgirl outfit I put on the other night, I haven't dressed in anything that would be dubbed “slutty.” I guess I have to get creative today. I should go all out, then let that be it—maybe I won't need to dress up anymore.
With that, I got up, showered, and ate breakfast. I then went into Ms. Stevenson’s closet and picked out a “slutty” outfit. I wore a red thong underneath a jean miniskirt and a red tube top, the breast forms inside it. For shoes, I went with a pair of clear “hooker heels” with an ankle strap. I put on the makeup and clipped on a pair of big hoop earrings.
If I didn’t know better, I’d say I looked like a prostitute. I shifted uncomfortably. This thong is giving me a killer wedgie, and these heels are ridiculous.
It didn’t take long for me to change out of the outfit. I turned on my laptop and started playing online games for the rest of the day.
That's when she showed up.
A voice echoed in the empty house. “Evening, hun!” I ran out of the office and looked down from upstairs. Standing in the living room, suitcase in hand, was Janet.
“
Ms. Stevenson?! I thought you weren’t gonna get back for a few more days?!”
“Originally, I wasn’t,” she said. “But the meetings ended sooner than planned. I was given a few spa days, but then I decided to head home and surprise you.”
I faked a smile. “Yep, I'm surprised all right.”
“Did you sleep in the master bedroom?” she asked me. Although I knew she couldn’t possibly suspect what I’d done, my heart began to race anyway.
“Oh shit, yes. I haven't made the bed yet.”
She smiled and shrugged. “Don’t worry, you didn’t know that I would be getting back so soon, so you can move your stuff into the spare and I’ll see you in the morning. I've had a long flight and would like a nice extended beauty sleep. Oh, and I’ll have a surprise for you once you wake up!”
“Okay,” I said. “See you then.”
Janet retired to her bedroom, and I put on my headphones and played video games into the night.
“John!” Ms. Stevenson called out from the hallway right outside my door.
“Oh god, what, what?” I quickly sat up, still half- asleep and cursing her for waking me up so suddenly.
She opened the door to my room and stood in the doorway. “Wake up, John!”
“Ugh, what time is it?” I said, rolling around in the bed.
“Seven-a.m., just in time for your training!”
I turned towards her, suddenly awake. “Training? For what?”
“You have three minutes to get out of bed and meet me downstairs,” she said, slamming the door.
“God damn,” I mumbled as soon as she was out of earshot. “What’s crawled up into her ass this morning?”
I rolled out of bed and headed downstairs. Ms. Stevenson was waiting for me on the couch, her laptop set up on the table.
“Sit,” she said. I sat down next to her and looked at her computer screen. “Good. So, an interesting thing happened while I was on this trip…”
“Oh?” I looked at her, wondering what she was talking about.
“I was between meetings, so I decided to log into my personal security camera website and watch some of the recorded footage.”
It took a couple moments for what she said to sink in. “Wait… what!?” I looked at her like a deer caught in headlights.
“Yes, I have three hidden cameras placed here in the house: one in the garage, one here in the living room, and one in my office.”
“Oh…” I replied, trying to hide the panic in my voice. She was watching me like a hawk.
“So, I logged in and started watching some of the video feed, and that's when I got a surprise. You were walking around my house wearing my clothes!”
I said nothing, hoping I had misheard her, but she continued: “At first I was like, ‘did he bring a friend?’ But then I looked carefully and realized that was definitely not the case.”
I looked at the footage on her screen. Spliced together were several scenes of me en femme.
Shit.
She leaned back on the couch. “Well, the thing is, it livened up my day seeing you dressed up like that. Who would've known you were a closet crossdresser?” She leaned forward. “So tell me, John: are you gay?”
I recoiled violently. “No!”
Great, here come the questions.
“Then why do you wear women’s clothes? Do you dream of becoming a woman? Getting a sex change?”
“No, none of that.”
“Then what is it?”
I hesitated. Never in a million years did I think I would have to explain myself to someone. While I always feared it would happen, I never actually planned for it. It was a secret I was hoping to take to my grave.
“Curiosity,” I said finally.
She cocked her head to the side. “Curiosity?”
I stood up and paced in front of her, ready to lay down the truth. “Yes. For a few years now, I’ve been getting curious as to what your clothes were like. Were they comfortable? what did they feel like? Pretty soon, I wanted to know the answer no matter what.”
“So, you just wanted to dress as a woman because…?”
“All I wanted was to experience being a woman on a very temporary basis. Just dress up, wear makeup, perfume, and heels, and that's it; close up shop and move on with my life.”
Her tone shifted. “Huh, well that is acceptable. You know, you’re not the first man I knew who would dress up in women’s clothes.”
Now that caught me off guard. “I'm not?!”
She crossed her legs and put her hands behind her head. “Nope. I dated this guy a year or so ago. Went out with him for two months. Then one night, we came back here drunk and I passed out on the couch after sex. I woke up in the middle of the night and climbed back upstairs to sleep in my bed and I see him standing there, in my lingerie, jacking off with my panties around his dick and a dildo up his ass.
I gulped. It’s a damn good thing she didn’t have a camera in the bathroom. “What happened?”
“I immediately dumped him and told him never to contact me again. I made him replace the clothes and delete my number. A month or so ago, I got bored and looked him up. Turns out he’s making forced feminization videos with a dominatrix.”
“Wow.” In my time spent on the internet, I had come upon that aspect of cross dressing many times.
She stood up and walked around the living room. “Back to the present. Truthfully, my business meetings did finish early and I got to enjoy a kickass spa day, but I really wanted to get back here and catch you in the act.”
“Really?”
“Yup. I watched all of the footage on the plane ride back. It was very enjoyable. Oh, and you have great tastes.”
“Pardon?”
She laughed. “I loved three of your outfits. The secretary one… that one was both sexy and hilarious. I loved watching you type away at your computer dressed like that.”
“Thanks…?”
“And that one with the white sweater and plaid skirt; that one was pretty cute. I might have to try it out. And… oh yes, that evening get-up you had. You looked like a cute little housewife all dolled up and sexy. That one was my favorite.”
“Really? Honestly, I felt the same way once I started eating.” My face turned red with embarrassment.
“But onto the main point here: you wearing my clothes without asking, John. You violated my trust, and that offends me. Honestly, if you had asked, I probably would've let you. But you didn’t, and now you must make up for it or else these videos are hitting the internet!”
My chest clenched in terror. “Oh please, don’t!”
“Then if you want this to stay a secret, you must do one thing for me.”
I hung my head in shame. Not only was my secret out, but if I refused to do what she said, everyone would know. “I’ll do it.”
She smiled. “I’m glad you saw reason. Here, take this key. First, you must go into my bathroom and shower – make sure you’re clean-shaven. Then take the key and use it to unlock one of the wardrobes. I'm sure you ran into it during one of your sessions, am I right?”
“Yes, I know the one.”
“Good. Open it up and put on the outfit inside—all of it—and then put on your favorite wig and doll up your face some. Then come back down here. I’ll be waiting.” She smiled gleefully. “Now go; get on with it!”
“Yes, ma’am!”
I quickly climbed the stairs and hopped into the shower and shaved the stubs of hair that were starting to grow back. I stepped out and dried off then went into her closet, key in hand.
I was wondering what she had locked in there. Now I’ll know…
I took a deep breath and opened the unlocked wardrobe.
Oh, shit.
I stood there, open-mouthed at the sight of the contents as Janet’s voice echoed in my head: “You need to put on all of it!”
I instantly recognized what the contents were: it was a complete head-to-toe French maid’s outfit. Ducking my head in shame, I got dressed.
I put on the corset and tightened it in the back. It was tighter than the one I had on last week, and this one gave me a much more defined hourglass shape. I stuffed the breast forms, which were more like actual breasts, in the cups of the bra. I now had bigger and more realistic breasts. I pulled on the black lace panties, followed by the stockings and attached them to the garters.
I put the satin slip on next and stepped into the maid uniform. The outfit was form-fitting and could be labeled a “naughty French maid” outfit, as the skirt portion was very short. I put on the apron and slipped on the black velvet gloves, then stepped into the heels. They were black patent six-inch heels with an ankle strap. I grabbed the brunette wig and sat down at her vanity and did my makeup, then headed downstairs.
“Oh my god!” Janet said, standing up. “You look like the real deal!”
“Really?”
“Yes! Now, if you want to keep your precious little secret from leaving this house, you must make my entire home spot-free. All the materials necessary are in the small closet over there. You have to vacuum the carpet, mop the hardwood, scrub the bathrooms, do the dishes, dust the place, and sort the laundry, and you must do that without a word of protest or else you get punished. Okay, Lynessa?”
“Lynessa?”
“Yes, that is your name for today. You can’t have a boy’s name when you’re dressed like that. Now get going!”
“Yes, ma’am!”
Several hours passed as I thoroughly cleaned her house. The outfit was incredibly sexy, and several times I had to show some self-control, otherwise I would’ve soiled the outfit and gotten in trouble. For that moment, I was a maid, and it was my duty to clean. Ms. Stevenson probably knew some pretty powerful people, and the last thing I wanted was for her to distribute the footage of me cross dressing and acting like a lady.
I’d cleaned before, but only my tiny apartment. Her house was huge, and I made sure I covered all the bases before leaving one room to start on another. Beds were made, the tile was scrubbed, the windows were cleaned, and all the surfaces were dusted. Everything was made spotless.