Only in October
Keywords: October, Only, in,
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"© 2003 by Thrillerauthor"
1995
"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.
1998
"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?"
"Tomorrow afternoon."
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.
"Nobody."
"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.
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Keywords: October, Only, in,