Only in Octoberbythrillerauthor©
© 2003 by Thrillerauthor
"Come on, Jimmy, it's time to get ready!"
I bounded up from the family room floor and raced as fast as my twelve-year-old legs would take me. Halloween! Trick or treat! Next to Christmas Eve, it was every kid's best day of the whole year.
Even if this year, I would be stuck going around the neighborhood with my stupid sisters. We had just moved to California from New York, and my parents didn't know my new friends well enough to trust me to go outside with them at night. Looking back on everything that followed, I am sure they later wished they had taken that risk.
Emily and Janet were 16 and 14, and they had promised that they would come up with a cool costume for me. My dad was out of town on a business trip, another fateful decision, because if he had been home, I doubt if he would have stood for what was about to happen to me. As I bounced into my bedroom, I found my mother and sisters waiting for me with odd grins on their faces. Emily was already dressed up as a cheerleader, and Janet looked like Princess Leah having a bad hair day.
"What's my costume?" I asked excitedly.
"Jimmy, you're going to be a girl tonight," my mother said matter-of-factly.
I stared at her in shock as my sisters started to giggle. "We have your outfit all picked out," Emily said. "You and Janet are exactly the same size."
"No way!" I protested. "I won't do it! Please, Mom, don't make me do it!" I started to cry as I backed away from them.
"Oh Jimmy, don't be such a baby!" my mother scoffed. "I've always wondered what you would have looked like as a girl, and this is my one chance to find out. Be a good sport, okay?"
"No!" Tears streamed down my face.
"What a baby," Janet said. "Crying just like a girl. You should have to wear dresses all the time."
"That's enough!" my mother said sharply. "Girls, you promised me that you wouldn't make fun of Jimmy."
I looked at her through watery eyes. "How long have you been planning this?" I managed to ask.
"It was my idea," Emily said. "When Mom said you had to go out with us, I thought gee, wouldn't it be cute if Jimmy came along as a girl. That way he'd fit right in with our other friends."
"Other friends?" I wailed.
"Yes, and we don't have time to waste. We're meeting the girls in half an hour."
"Mom, I won't go!" I cried.
"Then you'll just have to stay home and help me hand out candy to the children, if that's the way you feel. I do think you're making a mistake, dear. Go ahead, let the girls dress you up and have some fun."
I hung my head in misery. What could be worse than being stuck home all night with my mother doling out treats to the neighborhood brats?
"Do I really have to?" I asked meekly.
"Hooray!" Janet cried. "Come on, Jimmy, let's get you ready!"
Before I could protest, she took my hand and let me into her bedroom. I stopped short when I saw the clothes arrayed before me on Janet's bed: panties, slip, stockings, training bra, and the dress that Janet had worn to our cousin Ginger's wedding earlier that year.
"No way! You can't make me wear that?" I said in panic.
"What did you expect, Jimmy?" my mother asked. "Come on, get with the program."
I was so stunned, I let her gently remove my shirt, and then she told me to take off my shoes and pants. Standing there half naked, I looked up at my sisters, who had their eyes glued on my shorts.
"All right, girls, leave us alone for a few minutes, okay? You can help with the final touches." Without a word, Emily and Janet left us alone, closing the door behind them. "Now, Jimmy, take off your underwear."
"Mom, I'll put on the dress, but why do I have to put on all this other junk?"
"Please, Jimmy, just this once, do it for me, okay?"
Resigned to my fate, I turned around and took off my shorts. My mother reached over my shoulder and dropped the panties into my trembling hands. I stood there for a moment, and then I stepped into them and pulled them on. When I turned around to face her, I was shaking like a leaf.
"Don't be scared, Jimmy. Your sisters and I have to dress like this every day. Think of it as an adventure," she said as she deftly guided my arms through the straps of Janet's bra. After she fastened it behind my back and stuffed a few tissues into the cups, she stroked my longish hair for a moment. "When we get you dressed and put your hair in a ponytail, nobody will recognize you!"
With that, she took the slip off the bed and asked me to raise my arms. When the cool, silky fabric fluttered down over my smooth skin, I felt a strange stirring in my panties. I must have turned a bright red, but my mother mistook my blushing for simple embarrassment as the slip concealed the beginnings of my first ever erection.
"Now, sit down on the bed, and we'll put on your pantyhose."
Without a word, I hiked up my slip and sat on the edge of the bed, and she kneeled down in front of me and began to slide the stockings up my hairless legs. As the nylon moved up my calves, the unfamiliar sensation in my panties intensified, and I found myself holding my slip down to cover up a growing bulge. She seemed not to notice as she asked me to stand up and finish pulling my stockings up to my waist. When I did so, I felt lightheaded as I looked down at my stockinged feet, framed by the lacy hem of my slip. The feeling of the sheer nylon against my skin was like nothing I had ever experienced.
"Okay, honey, time to put on your dress," she said.
By now, I was so stunned by what was happening to me that I simply held up my arms again, and she laughed as she spun me around and dropped Janet's green taffeta dress over my head and arms and pulled it snug. I heard a zipper sliding up my back, and then felt a tug as she fastened the clasp.
"Turn around, Jimmy," she said, and I meekly obeyed. "Oh Jimmy, you look beautiful! Come in girls, and meet your new sister!"
The door bust open and Emily and Janet practically fell into the room. "Oh, my God! Look at him! He's so cute!" Emily cried.
"You mean look at her," Janet laughed. "How do you like my dress, Sis?"
"Come on girls, that's enough of that. Emily, will you please do something with Jimmy's hair before I put on his makeup?"
Makeup? That snapped me out of my trance. "Aw, Mom, not makeup!" I said half-heartedly.
"Just a little, appropriate for a girl your age. And Janet, will you find a pair of shoes for Jimmy? Try those black skimmer flats on him."
As Emily brushed my hair back into a ponytail and fastened it with a velvet bow, Janet went into her closet and returned with the shoes. They were tight, but with the stockings, my feet were able to slide into them. I took my first tentative steps in them as my mother guided me into Emily's room and sat me down at her vanity.
For the first time, I was able to see myself in a mirror, even though it was just my head and shoulders, and I watched in fascination as my mother took a little eyeliner and lipstick and applied it carefully to my now girlish face. When she was finished, she produced two clasp earrings and a gold necklace, and after she fastened them, she surprised me with a spritz of cologne behind each ear. I could only sit there in shock as my mother and sisters stared at me.
"Stand up, let's get a good look at you," Emily finally said, and she led me by the hand to the full-length mirror on her closet door.
When I saw myself for the first time, my jaw dropped and I heard myself gasp. Looking back at me with wide eyes was the cutest girl I had ever seen, with budding breasts and pretty legs shimmering beneath her knee-length dress. As she twirled this way and that to study her ponytail and tug the hem of her dress down over her slip, the strange sensation in my panties came back with a vengeance. Suddenly I felt the most delightful throbbing, and my young body shivered as I experienced my first orgasm.
My mother and sisters never knew. The rest of the night was a blur as I came down to earth and coped with the practicalities of walking and sitting in a dress, trying to talk like a girl, and pretend that I wasn't having too good a time. When we returned from trick or treating, I lingered in the kitchen with my mother and sisters, curling my legs up under my dress and rubbing my aching toes through my nylons as we divvied up our haul of candy. I was praised for being such a good sport, pictures were taken that I treasure to this day, and then it was time for bed. After I finally drifted off to sleep, I dreamed that when I woke up the next morning, a kilt, blazer and knee sox would be waiting for me at the foot of the bed.
"Mom! Dad! I made the team!" I shouted as I ran through the front door.
My father looked up from his newspaper and said, "I thought you weren't even going to try out."
"Not the wrestling team, Dad. The swim team! I'm the only sophomore to make the varsity!"
My mother joined us and gave me a hug. "That's wonderful, Jimmy! When do you start practice?"
Janet came down the stairs and asked my father for the keys to his car. "Did you hear Jimmy's news?" my mother asked her.
"Yeah, that's great, Jimmy. When are you going to shave your legs?"
"Shave his legs?" my mother and father asked in unison.
"I dated a guy on the team last year, and he had to shave his whole body for the season. Didn't you know, Jimmy?"
"Sure, it's no big deal. All the guys have to do it."
"Sounds fruity to me," my father grumbled as he buried his nose back in his paper.
He had never gotten over my unwillingness to try out for the football team earlier that year, even though he must have known that at 5'8" and 130 pounds, I would have spent the practices as a glorified tackling dummy with no chance of making the traveling squad.
"Who are you taking to the dance?" Janet asked as she opened the door.
"Hillary Fowler thinks you're cute. Why don't you ask her?"
The joys of having an older sister in the same high school. Hillary Fowler! Tall, beautiful, and unapproachable. She was a junior, and I had two classes with her, but I had never been able to screw up the courage to talk ask her out.
"Yeah, right," I said hopefully.
"I mean it. Give her a call tonight," Janet said as she walked out the door.
She said yes! Hillary Fowler said yes! I was going to the Halloween dance with my dream girl! She even laughed when I told her I had no idea what I was going to come up with in the way of a costume.
"Why don't you come over early, and I'll figure out something for you," she told me.
Which was just as well, because the next morning I was preoccupied with getting ready for swim team practice. The coach had instructed us to shave down before the first workout, and I spent over an hour in the shower, tediously removing the forest of hair that had grown over my chest, arms, and legs when I hit puberty. Before I came downstairs for breakfast, I self-consciously dressed myself in jeans and a long-sleeve sweatshirt, even though it was going to be a warm day with Santa Ana winds.
Practice was grueling, with endless repetitions, back and forth down the crowded lanes. With my long hair tucked into a cap, I was amazed at how my hairless body seemed to slide through the water, and I now understood now why competition swimmers put up with the hassle of shaving down. When the coach finally turned us loose, I dragged myself back home and collapsed onto the sofa in the family room. Janet was at a football game, and my parents were out playing golf. In retrospect, there is no doubt that my utter exhaustion set the stage for the events that were about to unfold.
The telephone rang and I could barely lift the receiver. "Hello."
"Jim? This is Hillary."
I snapped to attention. "Hi."
"When are you coming over?"
"I just got back from practice. Any time is good."
"How about now? We'll need some time to find a costume for you. I can fix us something to eat before we go to the dance."
"On my way!" I said, my fatigue momentarily overcome by the excitement of seeing her.
Hillary lived about a half a mile away, and after leaving a note for my parents that I would be back after the dance, I dragged my weary body to her house.
When Hillary opened the door, I was surprised to see her dressed in army fatigues and combat boots, with camouflage paint smeared on her pretty face. Her hair was tucked up under an army field cap, and she had glued a fake mustache above her desirable mouth.
"Wow," I said, "I didn't know I was going out with a guy."
She laughed and led me to the stairs. "My parents are up in LA, so we have the house to ourselves," she said. "Come on up, and we'll find you something to wear."
My heart skipped a beat at the thought of being alone with Hillary, even if she was dressed as a combat soldier. Her bedroom was not what I expected: whereas my sisters' rooms were filled with cuddly animals and pictures of rock stars, the only decoration in Hillary's room was a poster of Judy Garland wearing a top hat and tails.
I waited awkwardly at the threshold of her room as she went to her closet and sifted through her hangers. "I thought I had an old prison suit in here that I wore one year, but I guess my mom gave it to the church thrift store," she said. She emerged from the closet and sized me up. "Hmm," she said. "Take off your shirt."
Needless to say, I complied. She walked around me and asked me to take off my jeans. Not believing my good fortune, I unbuckled my belt and let my jeans drop to the floor.
"Oh my, look at those legs. I think I have the perfect costume for you."
Suddenly I remembered my hairless state, and I started to stammer an explanation. "I know you're a swimmer, Jim, that's how you got that beautiful body. Have you ever dressed up as a girl?"
"Once," I blurted out, "my sisters made me do it, on Halloween."
"Would you let me try to dress you up for the dance?"
What could I say? Here I was, practically naked, alone with my dream girl in her bedroom, and she wanted me to wear her clothes. The fact that she was dressed as a man only made it more surreal.
"Can't you think of anything else?" I said lamely.
"Come on, Jim, it will be fun. Whaddaya say?"
"I guess, if you really want me to," I said.
Before I could change my mind, Hillary returned to her closet and started searching through the hangers. She found what she was looking for and pulled out a short wool jumper. She tossed it on her bed and looked through the closet some more until she found a white blouse with a high ruffled collar.
"These have always been too big for me, but they should fit you perfect," she said as she started pulling lingerie and stockings out of her dresser drawers.
It is hard to describe my feelings at that moment. On the one hand, I was mortified that my dream date had turned into a freak show. But as I watched her selecting a bra and panties for me, long-suppressed memories of a magical Halloween night, years ago, flooded back.
She broke my reverie when she sniffed my hair and said, "Yuck. Do you shampoo with Clorox?"
"I've been in a pool all afternoon."
"Well, I'm not going to smell that all night. Report to the bathroom down the hall and await further instructions."
"Yes, sir!" I saluted my man in uniform. She followed me into the bathroom and handed me her father's razor. "Get that peach fuzz off your face, and then get into the shower. My shampoo and conditioner are in there, use them both. And you can dry yourself off with my towel. Any questions?"
"No, sir!" I saluted again as she closed the bathroom door.
I did as I was told, and as I was drying off with her towel, the door opened a few inches and her hand appeared with a pink robe and a pair of panties.
"Put these on and report back to the bedroom."
The door closed before I could respond. As I put on Hillary Fowler's panties, I felt a stirring in my loins, and I hurriedly wrapped her robe around myself and returned to her bedroom. She was waiting for me with a hair dryer in her hand.
Hillary had me sit down at her vanity, and as she methodically dried and brushed my long hair, I closed my eyes in anticipation of what was to come. For the second time in my life, my hair was fashioned into a ponytail, this time with a scrunchie, and then she started in on my makeup. After she sponged on some foundation, she went to work with powders and brushes, and I watched in fascination as my face became more and more feminine. When she started to apply some lipstick, my penis suddenly jerked in my panties, and I pulled Hillary's robe over my growing erection.
"This is so much fun!" she said as I stared at myself in a daze.
"Okay, time for phase two," she instructed me, and I followed her back into her bedroom. She handed me a pair of suntan pantyhose. "Do you know how to put these on?"
"I wore them once on Halloween," I said.
"Then you know there's nothing to it. Be careful not to get them all twisted when you pull them on."
I sat down on her bed and began to slide her stockings up my legs. Once again I experienced the exquisite feeling of sheer nylon against my smooth skin. I stood up and did a knee-bend to pull them tight. Hillary did a double-take when see saw my raging hard-on.
"Whoa, Mister, where did that come from," she said as she picked up a padded bra. I tried to think of something to say while she fastened the bra behind my back and adjusted the straps. "Here, put this on, maybe it will help," she said, handing me a short white half-slip.
I stepped into it, relishing the sensation as the silky fabric brushed against my nylons. The outline of my engorged cock was clearly visible as it pressed against my slip.
"I think this is turning you on," Hillary said.
"You're what's turning me on," I managed to say. "I've been dreaming of going out with you since the first day I saw you."
She took my face in her hands and kissed me on the lips. She was taller than I was, and I had to stand on my toes as I kissed her back. Suddenly she pushed me down, and I fell back onto her bed, my legs in the air. Hillary unfastened her belt and let her trousers and boxer shorts drop to her ankles. Then she fell on top of me and started to kiss me again. I felt her pulling my pantyhose and panties down to my knees, and I couldn't believe it when she straddled me and lowered her pussy onto my erect penis. She started to hump me, faster and faster, and I cried out in ecstasy as I exploded into her.
Hillary lay on top of me, panting from the exertion. "Was that your first time?" she asked at length.
"Yes." It occurred to me that I had just lost my virginity, wearing women's clothing, to a girl who was dressed as a guy. What was happening to me?
"That was awesome," she said. She rolled off me and disappeared into the bathroom, leaving me to my confused thoughts. When she returned, she was holding her lipstick. "I've never had to wipe a guy's lipstick off before. Here, your face is a mess. Let's see what you can do with it."
I stuffed my now limp penis between my legs, straightened my panties and hose, and walked over to the full-length mirror on her closet door. I was entranced by the reflection of a girl wearing a slip and stockings, applying lipstick to her pretty face.
"Not bad, Missy," Hillary said.
She watched me put on her blouse, fumbling with buttons that were backwards for me, and then she helped me into her jumper, tying the bow in the back for me. It came to mid-thigh, and my legs looked terrific in the mirror. Hillary rummaged through her closet for a pair of weejuns and asked me to try them on. With an effort, I was able to wedge my feet into them.
She stood back and admired her creation. "If I didn't know you were a guy, I would never believe it. This is so cool. Let's go downstairs and I'll fix us something to eat."