His Favorite Halloween                by: Marnie Smith

 

One October day, I was at the zoo with two friends. One was Joe, a lifelong friend who lived on my street. We always have been good friends. The other was Mark, a kid who had moved into the neighborhood that year. I was sixteen. In my mind, grown up, but still without a driver's license. Stuck in that in-between world. We spent that day wandering about the zoo, talking and looking. Joe said something about Halloween would soon be here.

Mark said, "I still trick and treat."

"Really," Joe responded? I haven't trick or treated for over three years.

"Yes really," Mark said, "it's a blast. I do it every year. I just go as a girl."

My eyes widened for a moment. That sounded embarrassing and I was taken aback at his claim. I couldn't imagine a boy my age dressing up as a girl, but maybe Mark had meant that he had done that when he was younger. Hopefully, a lot younger, but I really didn't want to hear any more. "We just don't do that anymore," I said, "I haven't dressed up in years." I didn't want to say any more about it.

"Let's go out this year," he said.

"I said nothing, but Joe agreed that we would go out. He answered so quickly that I just assumed that it was understood that we would not wander about in costumes and certainly not dressed as girls. Halloween was two weeks later. I walked over to Mark's house to meet up with the guys. I rang the bell and it was answered by Mark's mother, Mrs. Kemp.

"Hello Jim, come in," she said. "You need a costume too. I think we can help."

"I'm not going to wear a costume Mrs. Kemp," I said as I entered the house. Mark's sister walked into the living room. Her name was Ann. She was seventeen, a year ahead of us in school and she was beautiful. In fact, I had been smitten with Ann from the first moment I met her. I longed to have her notice me, but I had assumed that to her, I was only her little brother's friend. An "untouchable" without a drivers license and certainly not a boy worthy of her wonderful charm and warmth. Ann was dressed up as a witch, but as was her way, an extremely pretty and sexy one. I was always tounge tied around Ann.

"Hi Jim," and she smiled at Mrs. Kemp. "Here's another boy who needs a costume."

I shook my head, but was unable to think of anything to say to Ann, but then another girl entered the room. I didn't know her, but she was also pretty. However, she wasn't in a costume. She had on a brown wool jacket and a black silk skirt. An outfit that a woman would wear to her office, not something a pretty teenage girl would wear which was what this person obviously was. A familiar voice said, "hi Jim." It was Mark, but it wasn't Mark, it was the new girl who greeted me. The new girl was Mark! He was dressed as a girl from head to toe. He was wearing one of Mrs. Kemp's outfits, plus a wig, nylons, high heels, and make up. At the zoo, I thought that he was talking about dressing up as a girl back when he was younger and I had dismissed it. Here he was. He was all dolled up, he was beautiful, and if I hadn't known he was Mark, I never would have suspected that he was a boy.

I gulped, "Mark, I thought we weren't dressing up?"

"I told you that I always dress up as a girl on Halloween."

"Well, you can if you want, but Joe and I aren't doing it ever," I said.

Ann started to giggle and said, "Jim, maybe Joe should speak up for himself. Come out Joe."

Suddenly, another girl appeared. I knew her anxious and nervous face only it was not a her, it was Joe! He had on white stockings, a navy blue wool jumper, a white blouse, and a wig. His face was made up too. Joe was also made a very pretty girl. I couldn't believe it. Joe's face was red, even visible from under his perfectly made up face. "Ann talked me into it." A broad smile came to his face, "now it's your turn Jim."

"Oh no," I cried out.

"Yes," Ann said, "I have just the dress for you to wear."

I turned toward Ann and I'm sure my face expressed disbelief, "uh, uh, uh," I finally spit out, "I am not dressing up as a girl."

Mrs. Kemp spoke up and said, "Jim, it's just for fun."

Ann came over and she took my hand. "Jim, I'd really like it if you came out with us tonight. I'd love to do your costume too."

Out with us??? Ann was coming with us? "No, I just couldn't," I said, and my eyes actually began to glisten. Did Ann really mean that she'd come out with us? My friends jumped all over me. They asked why I was such a chicken and what was I afraid of? Joe started clucking and Mark called me a baby. I hesitated with my protests for a moment and Ann realised that she had an opportunity. She took both of my hands.

"Tell you what Jim, just let me fix up your costume. Just you and me in my room. If you don't like the way you look then you simply change back into your own clothes and you won't have to do it. No one will see you."

I was losing the fight. "Well, I don't know...."

"Please Jim."

"I won't leave your house, OK?"

Ann beamed at me and said, "of course." She told me to follow her to her room and she went to her closet and pullet out a dress. "This was my dress from the prom last year." She held it up against herself. "Do you like it?"

I pictured Ann in that dress. "Mmmm yes," I murmured. It was rayon and silk over burgundy velvet. It was gathered at the waist with a black taffeta skirt and short sleeves. Oh, she must have been lovely in that dress. It really was a beautiful dress. Then I realised that Ann pulled it out because she wanted me to wear it. I was taken aback as she offered it to me.

Ann laughed at my hesitation and said, "to get started, you'll have to take off your pants." My face turned red, but I unbottoned my jeans and pulled them down. I also took off my shirt and I reached for her dress. "What are you doing," Ann cried.

I was confused. "Don't I have to put it on?"

"Yes, but it's not that simple. You'll need other things such as stockings and a bra." My face turned red, but Ann was unruffled. She walked to her bureau, opened a drawer, and fumbled about. "Catch," she said, and she threw some black lacy silk panties toward me. "Slip those on." I hesitated. "Jim, put them on."

"But they're panties," I replied with a trembling voice.

"Of course they're panties silly. You can't wear my dress over your dumb boys underwear." She looked at my legs, "good, they not hairy so you won't need to shave them as Mark and Joe did. Now put on those panties. I'll turn around. Tell me when they're on." Good God, I thought, what am I doing. I slowly pulled off my underwear and nervously stepped into Ann's pretty panties. Ann now held sheer black pantyhose which she handed to me. I stood there wondering what to do with them. "You put them on, Jim. I'll help." She took them back and began to slowly and carefully roll up the right leg as I had seen my mom do many times. "Sit down Jim. You have to sit when you put stockings on." She began to work my right foot into the hose and then she rooled the left leg and slowly her stockings engulfed my legs. Then she asked me to stand and she gently pulled them up around my waist. "Now, watch what I do, " she said. Ann lifted her skirt and gently used her hands to pull her own stockings up so that they were nice and snug. She gently used her palms to pull up each leg. I did the same. "How do they feel Jim?"

"What? What do you mean?"

"Do they fit?"

I didn't know. I had never worn stockings. I took a few steps and immediately noticed how the air felt cool around my legs as I moved. It was a nice feeling as one leg brushed the other. "They're OK."

Ann laughed and held out a bra. I was told to extend my arms and she slid it on and clasped the clasps. Ann inserted shoulder pads into it to give me a bustline. There was a knock on the door. Mark and Joe. "Don't let them in," I pleased as my face blushed. "Not yet."

Ann smiled and called out, "you girls stay out! You'll have to wait." Next she pulled out a black silk slip and handed it to me. I put it on without help, but the feeling of the silk sliding over my legs was sensuous and wonderful. Ann gently guided me to her vanity. I was told to sit down, but as I did, she told me to sit as a girl would sit. That I had to keep my legs together and she told me to smooth out my slip as I sat. I did as I was told and relished the feeling that danced about my legs as I crossed them. Ann smiled and she began to apply makeup onto my face. I squirmed and nervously wondered how I would look as the unfamiliar smells of her foundation and lipsticks entered my nose. She finally told me to turn and look in the mirror and I couldn't believe what I saw. I definately looked feminine. I might have passed for a girl, even a pretty girl, if I had long hair. "Now," Ann whispered, "it's time to try on my dress."

I was ready to try it on. After all the preparations, I was curious to see what I'd look like in a dress and how it would feel. I stood up nervously wondering what to do. Ann unzipped her lovely gown and held it up for me so that I could step into it. As I did, I eased my arms into the sleeves. Ann zipped me up and I started to move toward the mirror, but she stopped me. "Wait Jim, your wig and shoes." She gently pushed me into a sitting position onto her bed, but made sure I used my hand to smooth my skirt. She went to her closet and came out with a blond wig and burgundy pumps. she put the long blond wig onto my head and combed and fussed with it untill she was satisfied and said, "can you put on these shoes?" I nodded and I crossed my right leg to comply. Oh that feeling as my legs brushed across each other. I slipped on her pump and quickly recrossed my legs the other way to put on the other. Ann giggled at my movements and laughed out loud as I tried to stand, but in her pumps, I lost my balance and I fell back on the bed. "Joe was just like you." She helped me to my feet.

"And Mark," I asked.

"Oh he's used to them." Used to them, What did she mean by that? However, I didn't dwell on the comment because I wanted to finally see what kind of girl I was. What a thrill I got as I walked to the mirror in Ann's beautiful clothes. The slip glided against my legs which her dress glided against the slip. I had no idea that wearing girl's clothing felt so nice. My next surprise was my appearance. I looked like a girl. I really thought I did, but not just a girl, a lovely girl. "Jim, you look great," Ann beamed.

"Do I? Do I really?," I looked again in the mirror. "I do look.....OK, don't I?"

"Jim, you look fabulous," she said as she gently put pearls around my neck. "I'll loan you my favorite earrings and my bracelet." I let her put these things on me. Now I wanted to show myself off to my boyfriends. I reached for the door as Ann laughed and called out, "girl's, get ready for the wonderful Ji...., I mean Jan!" I smiled and took a step and Ann said, "walk like a girl. More curvey."

Yes, I thought, walk like a girl. I entered the living room where Mark and Joe were sitting on the sofa with their legs crossed watching TV with Mrs. Kemp as if they always sat around in dresses. They both looked at me. There was silence. "Well," I said.

Finally, Mrs. Kemp spoke. "Jim, you look great. I wouldn't, no I couldn't guess that you weren't a girl. My two friends looked amazed.

"Not bad Jim," said Joe.

"Well", I smiled, "let's do something."

Ann laughed, "I thought you said you wouldn't leave the house?"

"Oh, yes." I had said that. Would they think I liked being dressed that way. I mean, I did like it, but I didn't really want anyone to know I liked it. "Well, maybe we could take a short walk." I acted nonchalant and cool about it.

"Sure," Ann said, "let's go out. Come one girls." My friends stood up and at the door Ann gave each of us purses that matched our outfits. I dropped my wallet into mine. As I stepped into the cool night air, another delightful sensation rippled up my body as the night's coolness rose up my dress. As my legs moved, I felt an unaccustomed coldness on each of them. We walked in silence. I wondered where I could go dressed as a girl. Maybe this was just too embarrassing. In fact, I don't think any of us knew what to do and we walked in awkward silence which was only broken by our heels clicking on the pavement. Finally Ann said, "girls, we'll go to the school Halloween dance, but first we'll stop at your houses so that your parents can see how nice thier daughters look."

I gulped, but I also thought of my mom opening our door and seeing me all dolled up. I thought that I looked so good that a new confidence was building inside me. It would be so funny. "OK, let's go to my house first." We walked to my street. I felt somewhat awkward in my high heels as I moved, but the different sensations that I felt being in women's clothing was tantalizing. The breeze caused my skirt to flutter slightly and the fabric slipped over my chilled legs. I felt nervous as we walked up my front steps and with a pounding heart, I rang my bell. As two figures came I knew that they were mom and my sister Grace. I knew that Grace was dressed as a fairy princess. As they opened the door, I became scared and I did my best to hide behind Ann.

"Trick or treat," we cried out.

My mother and sister looked at us. Mom handed candy to Ann and said, "here's candy for the pretty witch, but why aren't you other girls in costumes?"

Grace giggled, "Mom it's Jim...and Mark and Joe!"

Mom blinked and said, "Jim?"

"Yes, mom," I answered meekly. Ann burst out laughing as a deep smile crept onto my mother's face.

"Jim, you are gorgious. Who would have thought that you could be such a pretty girl." She put her arm on Grace's should. "I have two lovely girls." She looked at Mark and Joe and said, "you boys look terrific too" Then she turned to Ann and said, "young man, I don't think I know you."

Ann laughed, "I'm Mark's sister, Ann. I'm a real girl."

Mom laughed too and said, "well you're adorable too Ann." Then she called to my father to come look at us. He was not as enthusiastic about our costumes, but at mom's request, he took photographs of us. I don't think dad liked the idea of his son walking around town dressed up as a girl.

However, we continued our outing. Joe was too chicken to ring his doorbell. We relentlessly teased him, but he stayed out of sight while the rest of us surprised his brothers and parents. We assured them that Joe looked radiantin his feminine costume. His older brothers followed us to the street where they teased the hell out of him. They lifted his jumper above his waist and yanked his pantyhose down around his legs, and they pulled his wig off of his head. Joe was very embarrassed, but Ann was sweet and reassuring as she helped him get himself back together. She gave each of us more lipstick and said that it was time to go to the school dance. Joe was rattled and he wanted to go back to Mark's to change back into his own clothes. I had a certain dread at the thought of going into the school dance as a girl, but I was just enjoying it too much to chicken out. I was just having too much fun and as each person reacted to me as if I were really a girl, I became more and more mesmerized with my girlish appearance. Part of me thought it was very strange to be walking about the town dressed that way, but I became more and more confident of my new found beauty. To my surprise, I found myself talking Joe into staying in his jumper and coming with us to the dance. He finally agreed.

The dance, of course, was a costume party. We had to show our school IDs to the teachers at the front door who giggled when they realised that three of us were boys. We walked about awkwardly. At first, few recognized us. It seemed that the girls were the first to discover who, or what, we were. They seemed to relish our costumes, congratulating each of us on our courage and originality. I kept blushing as girls I knew complimented me on my dress. The boys were less kind, but none of them harassed any of us as badly as Joesn't brothers had harassed him. Suddenly, Ann asked me to dance with her. I nervously allowed her to take my hand and she led me to the dance floor. I had trouble dancing in my heels and Ann was amused. When the song ended I started to lead us off of the floor but Ann stopped me as a slow song started. "Let's dance this one too." I nodded as I put my arms around her. "Jim, you seem pretty comfortable in my pumps," she teased.

Unruffled, I said, "no more than your brother."

"Mark has always enjoyed dressing up as a girl." I must have looked stunned, but she continued, "it started when we were young, he and I would play dress up. I liked haveing a girlfriend in the house, but he never grew out of it. Have you ever done this before?"

"No," I replied. "How often does Mark do this.?"

"Every now and then. Not too often. Once, just for fun, we got all dolled up and we wenet shopping for dresses. Mom got very upset and said that he could only do it on Halloween. That's why she was so happy when you boys agreed to dress up with him."

I felt a wave of confusion flush over me. Mark was a transvestite. I had seen transvestites on television talk shows. I wondered if I was a transvestite. I had had such a good time that evening and I hadn't dwelled on any ramifications of those actions. I was suddenly very uncomfortable. "Ann, I never planned to do this before I came over. I'm not that way," A look of confusion crept onto Ann's beautiful face. I was afraid that I had said something to make her angry. "Ann, maybe we should leave." I began to pull away from her.

She wouldn't let go of me. "Jim, don't leave. I've had a crush on you since the moment I met you last summer. I don't know "what way" you are referring to, but I don't mind that you're dressed up like a girl. I don't care how you dress." She lifted her face toward mine in preparation to kess me.

"Don't," I gasped, "not with me this way.

She tightened her grip and said, "then stop me." She gently kissed me on my lips. I didn't stop her, but then I was overcome with the uncotrollable desire to kiss her back and I didn't care what I was wearing. Our lips met again and we kissed deeply. Some of the kids started to stare at us. Not everyone knew that it wasn't two girls kissing. A gym teacher ran up and yanked us apart.

"Girls, hey you two....," he cried, "stop it. You can't do that here." Ann and I looked at each other and laughed. I laughed so hard that tears began to stream down my face. I didn't know that my mascara was running.

"It's OK coach, I'm a boy."

"And I'm a girl," Ann chimmed in. The poor coach looked angry and said, "really." then he shook his head and walked away.

I grabbed Ann's hand and said, Let's get out of here." She nodded and I called to Mark and Joe, "you girl's are on your own." We walked out of the gym holding hands. We stopped for a few minutes to kiss on a bench in the schoolyard. Our lips got lipstick onto each other, but we didn't care. Eventually, I found myself back at Ann's house where I almost reluctantly I took off her dress to turn myself back into a boy. The only fear I had was that Ann wouldn't feel the same way about me in my boy things. Luckily, she did. She became my girlfriend for the rest of high school. I followed her to the University of Illinois and we dated throughout college. We were married two years after that.

Every Halloween, I dress up in some kind of female costume. Sometime Ann dresses as a man or sometimes as a girl to match my feminine outfit. Either way, we always have a great time. Once, we went out of town for the weekend. I met Ann at the airport and we went to New York City. When I returned to the hotel the next morning after my morning run, all of my male clothes were gone. Ann had checked them with the concierge, but had said that she had thrown them out. She made me wear women's clothing for the rest of the weekend. We had a great time and even when she returned my male stuff to me for our return home, I insisted on traveling as a girl. My brother in law, Mark, sometimes joins us on our Halloween escapades. He still likes to dress up as a girl. In fact, he joined a crossdressing club and does it much more than I do. As far as I know, our friend Joe sticks to men's clothing. Ever since that Halloween, I've had a few doubts about how "normal" this stuff is. I don't really dwell on what a transvestite is or isn't, but I have a wonderful wife and we love each other and with her love, doubts about myself do not well up within me. No matter what I am, I find that I always enjoy the transformation that takes place when I spend a few hours dressed as a girl.

© 1999
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