by Jane Futa
“Don’t you have plans or something?” I asked her. “It’s Saturday after all.”
“Not that it’s any of your business, but yes. I have a date.”
“Well you better get going,” I said, not even trying to hide my intentions.
“It’s not for a few hours,” she said, looking at me with a curious expression. “Why? Do you have someone coming over or something.”
“Uh…yeah!” I said, excited for the sudden excuse to need the house empty. Fortunately, our parents were on vacation so all I needed was for Emma to leave.
“You’re such a liar, Chris,” she said. “What girl would want to visit you?”
“What do you mean? I’m attractive enough,” I said with my hands on my hips, puffing my chest out.
“You’d attract another man sooner than you’d attract a woman. You’re just so thin and fragile looking.”
I knew she was right, but little did she know that I was going to be using that to my advantage soon. I rushed up to my old room and played some video games while I waited for her to leave the house.
“See ya, twerp!” she called when she finally headed out.
I threw down my controller mid game and watched her leave through the upstairs window. Perfect, I thought.
When her date’s car pulled out of the driveway, I opened my bedroom door and listened to the beautiful sound of silence. Then I rushed into Emma’s room to do a bit of exploring.
I pulled open her closet door and was blown away by all of the items that were hanging. She had something in every color and pieces I’d never seen her wear. I dragged my delicate fingers along the fabric in amazement.
What would a babysitter wear to an interview? I tapped my finger against my chin as I thought. I flipped through each item looking for inspiration. Then I came across a strappy floral dress about knee length. I pulled it off the rack and walked over to Emma’s full length mirror. I held it up to me, tugging the skirt out to the side to picture how it would flare out once it was on me.
The dress was perfect except for the slightly cool weather. I looked back at Emma’s closet. My heart jumped for joy when I saw a small white cardigan. Perfect! I thought as I pictured myself dressing like a goody-two-shoes to the job interview.
I quickly pulled the dress off the hanger and tossed it to the bed. Then I slid down my jeans and tossed off my t-shirt. I looked down at myself as I remembered I only ever owned boxers.
I can’t wear boxers under a dress, I thought. I bit my lower lip as I tried to find a solution. Then my eyes caught sight of Emma’s dresser. Bingo!
I rushed over and pulled out the top drawer. There, I saw an array of colors and fabrics all cut into different pleasing shapes. I plunged my fingers into the mix of silk and cotton and closed my eyes as euphoria set in.
Everything is so soft and smooth, I thought. Everything is delicate and dainty. I suddenly longed to feel delicate. I’d always been waif-like, but having a cock still made me feel somewhat masculine. I opened my eyes and searched for the most feminine thing in the drawer.
I slowly pulled out white lace and my face lit up when I realized it was a thong. I’ve never worn anything like this before. I eagerly slid my boxers down to my ankles and stepped out of them, letting my small cock sway as I wiggled my hips.
I bent forward and slid a foot in each leg hole of the thong. I delighted in the feeling of delicate lace sliding up my long, slender legs. For a moment, I imagined myself in makeup, with long, flowing blond hair. I pretended to brush it back behind my shoulder and finished securing the panties around my waist.
They hugged my small cock and balls, and I shifted them slightly until it felt snug and comfortable. Then I walked over to the mirror to assess my new image.
I shocked myself. I had no idea that it would take a single pair of lace panties to transform me into a feminine creature. I shifted my hips and leaned on one leg, dropping my arms nonchalantly. I felt my fingertips brush against my thigh. I leaned my head back and relaxed my jaw, touching my skin as if a man were touching me.
I lowered my cheek to my shoulder and gasped at the chill crawling up my spine. My fingers crawled closer to my lace panties and traced the waistband. Then they danced up my stomach and to my chest, where I pretended I had underdeveloped breasts. I brushed my knuckles against my nipples and bit my lower lip.
My cock hardened against the lace and a warm tingle spread down my legs and into my toes. I opened my eyes again and saw a delicate expression. I stared back at myself with seductive, sultry eyes and eyelashes that fluttered in anticipation.
I exhaled a long, slow breath. Why hadn’t I ever thought to try this before? I wondered, awakening to every beautiful new sensation. As if snapping out of a dream, I rushed back to Emma’s open dresser drawer. I scoured the fabric until I found a similar white lace. I pulled it out revealing two small cups. Thank god Emma doesn’t have large breasts.
Clutching the lace in my fingers, I marched back to the mirror and held it up to my chest. I draped it across, trying to imagine it on me. Then I slid my arms in through the straps and cooed as it grazed my skin. I fastened the clasp behind me after failing a few times. Then I straightened the straps on my shoulders and looked back at my reflection.
Beautiful, I thought. I felt sexy, daring, and powerful. My face didn’t look like a young man’s anymore. It looked like a woman’s who knew her worth and beauty. It had a serious and sexy expression. I let my lips part and let a higher pitch moan escape them. The image was unmistakable…I was all woman.
I put my hands on my neck and slid them slowly down to my chest, cupping my breasts and feeling a warm pulsing between my legs. I let one hand slide down to my panties while keeping the other on my chest. I fondled my cock as if it were a woman’s pussy. I circled my fingers and massaged the skin through the fabric and thought I might come.
I knew I couldn’t come in Emma’s panties, though, so I held back and enjoyed the tease. I rushed back to the bed where I left the dress and picked it up. Time for a real show, I thought. I slid it over my head, exhaling sensually as the cool fabric glided down my back and ass. I couldn’t believe how amazing it felt to be wearing a thong underneath a dress. I felt the hint of a breeze from below, while my ass cheeks touched the dress fabric. It was the best feeling I’d ever experienced.
I couldn’t help but feel sexy in these clothes. But the object isn’t to feel sexy, I thought, reminding myself of my ultimate goal. The object is to land a goody two-shoes babysitting gig. But suddenly, this wasn’t only about money. Suddenly, I wanted a thong and dress of my own. Maybe Emma won’t miss these. She certainly wouldn’t blame me. I laughed to myself.
I shifted from side to side in the mirror, watching the skirt of the dress sway as I twirled. I couldn’t believe how convincing I was. I played with my hair in the mirror, trying to style it more like a woman with a short haircut. Then I remembered the sweater.
I slid my arms through the soft cotton sleeves and let it drape beautifully along my torso. Perfect, I thought. Everything about me was conservative except for the thong hiding under my skirt. No one would have to know about that, I thought. I was pleased to have a little secret to myself besides just having a cock. I couldn’t help but chuckle at the deception and the lengths I would go through to get a job.
Shoes! I thought. I needed conservative shoes. Unfortunately, Emma and I were not the same size there. Emma had dainty feet and while mine weren’t large, I couldn’t wear a size 6 in women’s. I decided to pack up the outfit and head to the nearest Payless.
Luckily, I found a pair of white sneakers that would look perfect with the cardigan and dress without revealing my masculine feet. I rushed back to campus and poured over the numerous babysitting ads. I made a note of who to call the next day and then tried to get an early night’s sleep. I wanted to be well rested for the performance I was going to have to give at the interviews.
Chapter 3
It was time for my first interview and I wa
s nervous as hell. At the same time, I was extremely excited. I would get to wear my sister’s panties again and pretend to be a woman. Fortunately, there wasn’t much pretending when those panties were on. I really felt like a beautiful, young woman. I had three interviews lined up for the afternoon after calling numerous moms for hours. I hoped I would get a job in the first three so I wouldn’t have to schedule interviews around school during the week.
I slid on my sister’s panties and bra, taking a moment to appreciate the fabric against my skin. I ran my hands along my body and inhaled the pleasurable feeling. Then I came to and slid the dress on. I had stolen a lipstick and mascara from my sister. I picked something faint so it wouldn’t look like I was trying too hard. I grabbed a light, almost neutral, shade of pink.
I pressed the lipstick to my mouth and slid it from side to side. “You’re so hot,” I told myself after pressing my lips together in a similar smack that I’d seen Emma do before. I applied the mascara and then looked over my image again, making sure there was nothing out of place or that I was missing.
When I was convinced everything was ready, I sneaked out of my dorm room. People knew me there and I didn’t want anyone to see that I was leaving looking like a chick.
At the end of the hall, however, was a group of guys I recognized. Their gaze instantly leapt to me and my slightly padded breasts. I could feel their eyes on my ass as I passed by them. Then they started whispering about me. I listened closely to see if they knew who it was, but they were only talking about how much they’d love to bang me.
I smiled to myself, pleased that my disguise was working. I also loved feeling desired and objectified. I had to control my cock from getting too hard because my mind was wandering to being gang banged by the group of guys in the hall.
I made it to my car and then drove to my first interview. The mom’s name was Carol Pearson. My jaw dropped when I entered her street. The houses were giant and intimidating. I felt small just looking at them. Maybe that’ll help me seem more convincing, I thought. Women were often shy and slightly intimidated, especially the younger ones. At the same time, I knew I had to see competent enough to do the job.
I parked on the street, even though they had a large wrap around driveway. I wasn’t sure what the proper etiquette was, so I played it safe. I walked up to the door and rang the doorbell.
A maid answered and let me in after I gave her my name. “Christina,” I said, assuring her I was here for an interview.
She walked me down a long hallway filled with glass windows and to a big office. I saw a middle aged businesswoman sitting at a large cherry wood desk. She had short blond hair and looked up at me through the top of her eyes. She wore reading glasses and peered at me just over their sleek silver frames.
“Christina?” she asked with a look of hesitation. She doesn’t like the short hair, I thought, brushing a hand through it nervously.
“Yeah,” I said, stepping in.
“Take a seat,” she said, pointing to one of two chairs in front of her desk. “You can close the door, Selma,” she told the maid.
“Wow,” I said, looking around her office. “What do you do?”
“I’m a lawyer,” she said. “My husband is a neurosurgeon. That’s why we desperately need a babysitter we can trust. I’d prefer a nanny but my husband doesn’t love the idea of a stranger living with us.”
“I can understand that,” I said, trying to keep my voice high.
“Do you have references?” she asked, bringing her hands just under her chin.
“Actually, I’m trying to get my first job. I have a little sister so I have experience helping out with kids, just nothing official.”
She looked at me suspiciously. Panic suddenly set in. What made me think I could get away with this? I could never pass for a woman. Then I noticed her looking at my crotch. I followed her gaze to my lap and saw the outline of my small cock through the thin dress fabric.
Oh no, oh no! My adrenaline pumped and the blood pounded in my ears.
“Do you have an erection?” she asked in a strange tone. I couldn’t decipher what she was thinking, and I couldn’t come up with a cover.
“Sorry,” I said quickly. “I’ll go.”
“No,” she said, standing up quickly. She looked as if she’d tackle me if I tried to leave. I couldn’t leave even if I wanted. My feet were frozen to the floor. “Look. My husband and I have no issues with trans women, but why do you have an erection during a job interview?”
“I’m not…I’m not trans,” I said in a shaky voice. “I just can’t seem to get a gig as a boy so I tried to be a girl.” I lowered my head in shame, wondering why I was giving her so much information. Something about her made me spill the truth.
“That’s very, very naughty,” she said almost more seductively than angrily. She walked around her desk and I saw she was wearing a tight, black, pencil skirt with nylon stockings. She pressed her ass up against the edge of the desk and leaned back. “So you don’t like wearing that dress at all?”
I looked up at her with confusion. Was she turned on by my cross dressing? “I don’t dislike it…”
“You know I could call your school right now and tell them everything.”
“Oh god! Please don’t,” I begged.
“How badly do you want me to keep your secret?”
“I’d do anything…” I admitted as the worry set in.
“Close your eyes,” she directed. I did as I was told and waited the next instruction. I heard the squeaking sound of a drawer being pulled out. Then it shut and I heard the clicking of her heels as she walked back over to me.
“Open your mouth,” she said. I relaxed my jaw so that it fell open. Then I felt two wet fingers press against my lower lip. “Wider.”
I opened wider. I could tell she was leaning toward me because her breath rolled over my face and the scent of her perfume swept through my nostrils. I felt her hand on my cheek, cupping it gently.
Then I felt the head of a cock enter my mouth. I was confused but didn’t dare open my eyes yet. Was she trans too? But soon I realized how much it tasted like silicon. A dildo? I wondered.
I wrapped my lips around the head and moaned as she slid it in. “Good girl,” she said. Then she slid her hand around to the back of my head and tugged on my short strands of hair. She pulled my head back, exposing my throat and shoved the cock in deeper. I started to gag and couldn’t help but open my eyes to protest.
She saw me struggling and eased up a bit, but still pushed it as far as I could tolerate. She pulled it out slowly and pushed it back in. She was moaning with pleasure as she fucked my face with her desk dildo. I wondered if her panties were wet yet.
I couldn’t believe ten minutes before I had been walking in for a job interview. Now the potential boss was shoving a dildo down my throat as punishment for cross dressing.
“You want to be a girl?” she asked. “Then you’re going to get fucked like one.”
I wondered what she had in mind, but my cock was ready. I was still sucking on the cock in my mouth and Carol still had a firm grip on my hair. She pulled the silicon slowly from my mouth and then ordered me to stand up. I did as I was told.
“Spin around,” she said. “Put your back to me.” I turned so my ass was inches from her. I felt her hands on my neck before they started gliding down my back. She slid my sweater from my shoulders and tossed it on one of the chairs. She leaned into my neck and kissed it tenderly as her hands roamed the front of my torso.
For just a teasing moment, Carol’s hand brushed against my cock. I moaned, feeling like a woman about to be ravaged by a rich, powerful man. She found the zipper on the back of my dress and slid it down slowly, exposing my skin to her harsh A/C.
She slid the straps down my arms until the dress fell to the floor. I looked down at my crotch, covered only by my sister’s white lace panties and watched Carol’s hand glide across at my cock again. Her hands roamed up my sides and around to my chest. She grabbe
d the padded fabric as if they were real breasts.
This is so fucking hot, I thought as I imagined my breasts being massaged by this powerful woman. She flicked my earlobe with her tongue and sent a warm tingle through my body. My cock twitched in approval as her fingers moved to the clasp of my bra.
She unhooked it effortlessly and ripped it off me quickly. She tossed it on top of the sweater and let her hands quickly resume massaging my chest as if a pair of breasts was there. I moaned and she moaned back.
“Bend over,” she whispered between gasps. I crawled into one of the oversize chairs, pressing my knees to the seat and bracing my hands on the chair back. “Good girl,” she said, spanking my ass.
“Oh!” I cried out from the painful pleasure. She ripped my thong down my thighs, exposing my ass. Then she pressed a wet finger to my hole and circled it around teasingly.
She pushed it in slowly. Holy fuck this feels good, I thought. It was the first time I’d ever had anything in my ass before. I couldn’t believe how amazing it felt to have this woman’s finger in me.
“Ready to get fucked?” she asked, wiggling her finger in my ass.
“Yes,” I replied.
“Good girl,” she said again, removing her finger slowly. She brought it around to my face and I eagerly sucked it clean.
Soon I felt the wet tip of a silicon cock pressing against my ass. At first my hole resisted like a tight little virgin’s hole, but soon it opened up around the hard cock.
“Fuck!” I cried as she pushed it in deeper, sending wave upon wave of ecstasy through me. My body heat rose and my legs quivered as she fucked my ass.
“Mmmm, just like that, baby,” said Carol. “Maybe this will teach you to dress up like a little slut. Unless…you like getting fucked.”
“I do!” I cried out as she pumped the cock in and out of me.
“That’s a good little slut,” she said, petting my head. “Scream for me.”