by Jane Futa
For fun, and to add to my collection of fantasies about Theresa, I looked through apartments in Los Angeles. As I had expected, the prices were laughably high, even for California. The next thing I did was look through job postings in the area, but there wasn’t much that I had the skills for. I sighed as I browsed and felt my mood sinking lower and lower.
Then I came across the most interesting listing. It was a live-in housekeeping position in the same part of Los Angeles where Theresa lived. The deal was that the housekeeper gets free rent and groceries in exchange for their services.
My eyes lit up with promise. I could do that! After all, I had to clean the pizza place every night at close. I didn’t have any debts so rent and groceries would be perfect. Then I read the qualifications and my hopes suck again.
Prefer a woman, it said.
That was the one thing I couldn’t even bullshit! I leaned my head in my hands and pouted. I was desperate. I would’ve done anything to get out of my parents’ home and closer to Theresa. I just had to find a way.
What if…no, no no. I couldn’t do that, could I?
Chapter 2
I paced the floor of my bedroom. Dress up as a woman? I let the thought spin around in my head. I considered the pros. I’d be out of my parent’s house. I’d be closer to Theresa. I’d live a nice life in Los Angeles. But the cons were terrifying. I get caught. Everyone finds out that I cross dressed. I lose the chance to ever work in LA again.
But the cons were only cons if I got caught. If I was convincing enough, if I could really look like a girl, then there wouldn’t be any con at all. I mean, besides wearing women’s clothing. Of course, the more I imagined myself in a cute little skirt and tight shirt, the more curious I became. I just have to embrace my feminine side, I told myself.
The other con was figuring out where to get women’s clothes. The only place I had any access to was my mom’s closet, but she never wore anything sexy. Her and my dad fought a lot, so I knew she didn’t really try to dress up for him. I wondered why she never dressed up for herself, at least.
I decided I would wait until both my parents were at work on my day off and then I’d sneak into her closet to see what she had.
When the day came, I sat near my bedroom window waiting for the last car to pull out of our driveway. Then I ran downstairs and made sure all of the doors were locked and the alarm was turned on. I would have plenty of warning if someone came back for any reason.
My nerves were jittery as I crept toward my parents’ bedroom door. I pushed it open slowly. My heart pounded in my ears as I stepped quietly toward the closet. Then I started laughing at myself. Why am I walking quietly? There’s no one home.
“Get a grip on yourself, Bryan,” I said aloud. I exhaled and continued toward the closet. It was a large walk-in closet filled with all kinds of outfits that I’d never seen my mom wear. I flipped on the light switch to get a better look and my jaw dropped. She must’ve had a secret shopping addiction I never knew about, because she had outfits for every occasion. She even had a rack devoted to sexy lingerie that looked as if it had never been worn.
“I can’t believe this,” I said to myself. I racked my brain for an explanation but I came up short. Then I noticed a u-shaped rack along the length of the closet walls which showcased hundreds of beautiful shoes.
I’d never dressed as a woman before, but seeing all of the varied fabrics, patterns, and colors made me a little giddy. I suddenly understood why women liked to shop so much. I stepped further into the closet and felt lightheaded as I completely surrounded myself with beautiful garments. Some sparkled, other were covered in lace. Some were satin and others were simple cotton. I was salivating and nearly foaming at the mouth. I wanted to try on all of them like it was some sort of addiction.
I ran my fingers across the blouses, dresses, and lingerie sets. It didn’t help that I was a virgin and had never touched a woman’s panties before. My fingers came alive and all of my senses buzzed with delight. Without thinking, I started pulling every piece from the rack and holding it up against me until I was eventually lying in a pile of women’s clothing. With a big smile spread across my face, I was finally ready to start my experiment. I was ready to start cross dressing.
I looked around me at the pile of fabric and tried to find something to try on first. The lingerie, I thought. I sat up, leaned forward and ran my hand across the delicate lace bustier and panties. Just touching them sent a warm electric wave through me and I felt my cock swell. I picked up the lingerie and held it to my chest. It smelled new and it still had the tags on.
I hoped that my mom wasn’t planning to return them. I stood up quickly and searched for a pair of scissors to remove the tags. I ended up in the master bathroom and started to strip naked. The closer I got to putting on my mom’s new lingerie, the harder I became. I started feeling grateful my cock was small so that it could be easily hidden inside a pair of panties.
I unclipped the panties from the hanger and slid them up my thin, lanky legs. Feeling the lace against my skin made me quiver. I pulled them up to my waist, moaning as it cupped my cock in place. I looked at myself in the mirror. My shaggy, shoulder length blond hair went in every direction. I knew I’d have to tame it if I was going to be convincing. I ran my fingers through it and frowned in disappointment when it fell back into its messy shape.
Then my gaze traveled to my groin. I could hardly make out my penis under the black lace fabric. I couldn’t believe how much it looked as if I had a pussy underneath the panties. I ran my hands over my thighs and felt a confusing tingle. It felt and looked almost as if I was touching a woman. Both of those were very new to me.
I picked up the bustier and fumbled with it until I had it hooked around my torso. It squeezed my chest tightly enough that it actually formed two smallish mounds. My pink-lipped jaw dropped. I had small breasts! I twisted my hips to the side and admired how well everything was coming together. I couldn’t believe how similar in size my mom and I were. There was something strangely comforting about it.
After a few more minutes of posing, I walked back toward the closet to look for a dress that I could try on. As I walked, the panties shifted against my ass and I noticed my hips swaying back and forth. Am I really enjoying this? I was dumbfounded but absolutely enamored. My head was light and I felt like I was in a daze. This was the most exciting day I’d had in a long time.
Just as I returned to the closet, I heard the alarm chime from downstairs. My heart stopped and I couldn’t remember how to breathe. Fuck. I had made such a mess. I hadn’t even considered someone coming home while I was tossing clothes on the floor. I had floated into a heavenly dream where every worry was lost.
Was I really about to be caught wearing my mother’s lingerie?
Chapter 3
I closed the closet door and started furiously kicking fabric to the sides with my feet. Then I flipped off the switch and slumped into a ball against the back corner of the closet. I prayed and hoped that no one would come upstairs much less into my mother’s walk in closet. I wrapped my arms around my folded legs and rocked back and forth, still dressed in lingerie.
I heard a familiar stair creak. Shit! I waited in the cold, darkness. I waited for them to leave or for the door to burst open. I waited to be found out or breathe a sigh of relief. I hoped so badly that I would soon be alone again.
“I swear I’d lose my head if it wasn’t attached to me,” I heard my mother say. That relieved a little bit of tension. I was at least happy to hear her voice instead of my father’s. “Where did I leave my phone?”
I breathed a sigh of relief. Her phone definitely wasn’t in the closet. There should be no reason she’d come in here. I started to relax when the closet door swung open.
I was horrified as I saw my mom standing there, peering into the darkness. There was only a sliver of light stretching across the floor, but it wasn’t enough for her. I watched with dread as she reached for the light switch and flipped it on.
Her jaw dropped and her eyes widened as if everything was in slow motion. I had entered a bad dream and there was no escape. Especially since it was real. I waited for her to cry or scream at me, but suddenly there was a smile that spread across her face.
“Bryan?” She started to laugh. Each laugh grew louder and louder than the last. I blushed and tried to will myself to disappear into the wall behind me. I closed my eyes as she laughed but when I opened them, I realized none of it was a dream. I was really huddled in my mom’s closet in her lingerie while she stood there laughing at me.
“Honey, what are you doing?”
“Uh…” I didn’t have an explanation besides the truth. I didn’t know if I had the balls to tell her.
“Playing a little dress up, are we?” She smiled, folded her arms across her chest and leaned against one side of the doorway.
“I can explain,” I said even though I wasn’t sure that I could.
“By all means,” she replied, nodding her head as if to urge me on.
“This is all for a job. A better job. In Los Angeles.”
“That’s hours away,” she said. “But Los Angeles? It all makes sense now…” She rolled her eyes as she scoffed at the culture. “They’re all freaks and weirdos out there.”
“No they’re not!” I cried defensively as I thought of Theresa. My beautiful, sexy Theresa.
“Ok, calm down,” she said. She smiled at me again. “This has completely turned my mood around.”
I blushed again and lowered my head. How humiliating, I thought.
“Well, if you’re going to dress up like a woman, you’re going to need a little help.”
I lifted my head and stared at my mom in amazement. “Really?”
“Mmhmm,” she said, reaching her hand out for mine, “let’s really dress you up.”
I couldn’t help but smile, even as awkward as the situation was. My mom, who was just laughing at me moments ago, was going to help me transition into a convincing girl. I grabbed her hand and felt warm inside.
“Thanks,” I said. “I was just about to pick out a dress.”
“Classic beginner’s mistake,” she said. “Let’s do your hair and makeup first.” I nodded and she led me back to the bathroom. She pointed to the fluffy white seat under the vanity counter. “Take a seat.”
Chapter 4
I sat at the vanity staring at my mother’s reflection in the mirror. The lines around her eyes and mouth were more prominent and her hair was starting to turn gray. But when I looked into her usually dull eyes, I noticed a bright gleam of happiness sparkling from them. She was amused at my situation, but she was also excited. My heart swelled with love for her.
“Ok. Let’s start with some primer.”
“I don’t even have the interview yet,” I told her.
“That’s ok. You’ll need to learn how to do this on your own if you get the job.” I nodded and let her continue. She pulled out a white bottle and squirted a white cream into her slightly weathered hands. She rubbed her fingers together and then applied the primer to my face. It was cool and smelled of vanilla which filled me with happiness.
“Now concealer,” she said. She picked up a beige cylinder and untwisted the cap, pulling out a long wand with a small sponge at the end. “You’re lucky. You won’t need much of this.” She dabbed a few placed on my forehead and under my eyes and then placed it back on the counter.
Next she applied foundation, covering my face lightly and evenly. As I watched her work, she seemed to have an added pep in her step. She started to hum and tapped her foot against the tile. I smiled and felt completely nourished by her love.
She told me that pink lipsticks would look good on me and to always choose an earthy eye palette. Black was okay for liner and mascara, but I needed something subtle for the lid and crease. She showed me how to apply everything, including a pair of fake eyelashes and eyebrow makeup. I wondered where she acquired all of this information. Was this just something passed down from mothers to daughters? Then I wondered why she never wore makeup like this anymore.
“Why don’t you ever dress up?” I asked her as she put the finishing touches on my face.
“Oh. Well I’ve been married for a long time, and your dad has never really been into a lot of makeup.”
“Sorry he’s so cruel,” I told her. Her bottom lip trembled but she caught herself before a single tear fell.
“You learn to live with it,” she said. “It could be worse.”
“Mom?”
“Yeah, honey?”
“Thanks for doing all of this.”
She smiled and collected herself. Then she slowly stepped back so that I could see my reflection in the mirror. “What do you think?”
I couldn’t believe it. The makeup and the eyelashes made my face look perfectly feminine. My jawline was too subtle to be masculine and my cheekbones were high like a fashion model’s. My heart beat quickly in my chest and I leaned in closer to inspect the makeup.
“I’m gorgeous,” I told her.
“Very. Now for your hair.” I almost couldn’t pull myself away. I was so hot.
Mom pulled out a straightening iron that she had heating up and a brush. Then she started to straighten my hair, one thick section at a time. Moments later, my hair was sleek and there was nothing left on my body that showed I was a man. I suddenly looked like a bombshell teenage daughter.
“You’re perfect,” she said as I flipped my hair back and forth, occasionally running my fingers through it. It felt so soft and smelled like coconut. “Now, we can find you a dress. And I have the perfect one.”
I watched as mom returned to the closet and shook her head disapprovingly at the pile of clothes on the floor. “You sure made a mess in here, hm?”
“Sorry,” I said with a slight blush. I looked back in the mirror and realized how much better my shyness fit a woman’s body than a man’s. It was almost endearing and sexy. I turned back to mom to see her digging through a pile until she found an emerald green business-casual dress. It was a conservative cut with a skinny white belt around the waist.
“Well. Don’t be shy,” she said while waving me over. I walked toward her nervously, but the excitement was building in my chest. My mom unzipped the dress and held it down by feet. I stepped through and she pulled it up my body and slid it over my shoulders. Then she zipped it up and took a step back. “It fits you perfectly,” she said. I could’ve sworn I saw a hint of pride in her eyes. “You know, it’s kind of fun having a son and a daughter.”
My heart was overjoyed. I returned to the mirror and looked at my reflection. Everything was perfect. I looked like a sophisticated woman. “Thank you,” I told her again. She nodded and wiped a small tear from her cheek.
“You’ll have to shave your legs before the interview,” she warned me. “You’ll probably have to do your makeup again alone.”
“I think I can handle it,” I replied.
“And don’t let your father find out.”
“I won’t,” I told her. She kissed my forehead and wrapped her arms around me in a long embrace.
“I have to get back to work. I’m in trouble enough as it is. But hey-“ she said while turning back to me, “good luck in the interview.”
I thanked her and watched her leave. I couldn’t believe how different things had become since the night before. Not only did I look like a perfect woman, but my mom accepted it. I flaunted myself in front of the mirror for a few more minutes before tearing myself away to try and get an interview. I knew that the last thing I would have to work on was my voice. Fortunately, it had never been that deep to begin with, so I was certain I could pass for a woman on the phone if I tried hard enough.
I made the call and the man who answered actually sounded surprised to hear from someone. “Is the job still available?” I asked in a high pitched tone.
“Why, yes. Yes, of course. How soon can you meet?”
The desperation in his voice concerned me a little, b
ut I was desperate. “As soon as a few hours from now,” I told him. He was very eager and we set up the interview for 4 p.m. That would give me enough time to shave and make the drive to Los Angeles.
I looked up his address and saw that he lived in a huge mansion in a gated community. And on the way to his house, I’d pass right by the street that Theresa lived on. I couldn’t believe how my luck was changing.
I hope I’m not getting into a stickier situation than I think. I hung up the phone and quickly ran to the bathroom to shave my legs for the first time. I was excited to feel my silky skin rub underneath the dress fabric, but I wasn’t prepared for how good it would feel when my thighs rubbed against eachother.
I ran my hands over my soft thighs and moaned. Then I grabbed a pair of heels from my mom’s closet and a purse and drove the car to Los Angeles.
Chapter 5
My prospective employer’s name was Wyatt and his house looked even bigger in person than in the photos. He had a circular driveway filled with stones and I pulled my car all the way up to the front door. When I stepped out, I tried my best to keep my heels from breaking on the rocky path.
I rang the doorbell and was greeted by a man who I assumed was a butler. He looked at me with a worried expression, but let me in anyway. He showed me to Wyatt’s office where I would be having the interview.
When I opened the door, I saw a room lined with bookshelves and a long, mahogany desk at one end. Wyatt, an older man with full, silver hair, sat in a large leather chair. He lifted his eyes from his paperwork to greet me, and a mischievous smile spread across his face.
“Melody?” I nodded. Melody was the new name I had given myself over the phone. “Well, it’s a pleasure to meet you.” He stood from his chair and walked toward me with his hand extended. I reached out to take it and he held mine in a sensual way, as if he was exploring every inch of skin. I watched his nostrils flare when he tried to smell me.