Happy Halloween — “Halloween is not only about putting on a costume, but it’s about finding the imagination and costume within ourselves.”
“Oh just sit down Tommy and hush. You said we could dress you up as a woman and you agreed to work this way all day today. It’s Halloweensilly,” Shelly said holding the cape and waiting for him to sit in the styling chair.
The other girls in the shop stood and watched as they giggled in anticipation of Tommy’s transformation.
It was early in the morning and all the stylists and the nail tech were all here to watch Tommy transform to be a female stylist for the day. Tommy had been hounded for weeks by the girls to allow them to dress him up as a woman for Halloween. They were all a very tight group and why not? All of them were going to be wearing costumes to Tonya the nail tech had done his nails the day before after closing. She had done them long and painted the bright red. The girls had a great laugh at his awkward reaction to having nails. Tommy had to be very discreet that evening going straight home after work.
Marie was wearing the typical witch costume with a pointed hat, a long black wig, and a black flowing dress. Linda was wearing a sexy tiger face painted on her face with a tiger-striped leotard top and a tail hanging seductively in the back. Morgan was the conservative one wearing just a pair of bunny ears.
Tommy was a slight man anyway and most people assumed since he worked doing women’s hair all day he must be gay. A typical stereotype that he didn’t fight, but he really was reluctant to be dressed as a woman even if it was Halloween.
“C’mon, Tommy, it will be fun,” they had said and he consented as long as it was kept inside the shop. It wouldn’t be just the girls in the salon who worked with but all the clients that would be in and out of
the salon all day long that would see him in his girly costume which caused him to feel embarrassed.
The cape was put around Tommy’s neck, and the towel was removed from his wet hair. Shelly combed it out and immediately began setting his hair in large brush curlers. The girls laughed at Tommy as he blushed from embarrassment while his hair was slowly filled with curlers.
“First time in curlers Tommy?” one of the girls asked amused at the sight of him having his hair set.
“Yeah,” he said with a slight grin.
That wasn’t actually true. Tommy had practiced doing roller sets on himself at home while at beauty school. He learned to wrap the different types of rollers into his own hair, and it paid off in the long run as he quickly was able to master the art of using curlers and perm rods. It was all for educational purposes but he would never tell these girls he had rolled his own hair over and over again.
When she had finished Shelly held Tommy’s head with two hands and faced
him to the others.
“What do you think girls? Should we have Tommy work today in curlers?”
“Oh yes,” was the enthusiastic response.
Tommy gave a shy smile and tried to go along with the idea that it was all for the fun of Halloween.
“Tommy, let’s get you dressed.”
Tommy was put in a girdle and c-cup bra and padded. The dress was white with red polka dots. The skirt was pleated and hung loosely to his knees. It had short sleeves and a large Peter Pan collar. Large red buttons ran in a straight row down his back and were fastened by the girls making it almost impossible for him to do anything about it. A 3" red patent leather belt was placed around his waist. He wore sheer seamed stockings with the seams adjusted perfectly in the back.
The girls all laughed and enjoyed dressing the young man as a woman for Halloween. He was obviously very nervous but allowed them to continue and cooperated with them.
“What do think Tommy? Do you feel like one of the girls yet?” Marie asked in the fun.
“I feel uncomfortable as a man, that’s for sure,” he said trying to play along still. the girls all laughed.
“Well sit back down here and let me do your make up and maybe you will feel different.”
“I’m sure I will,” he said nervously as he sat back down in the chair.
“You need to think of yourself as one of the girls today Tommy. It will be easier for you, rather than some man dressed as a woman.”
The makeup took a little while and blue eye shadow and eyeliner were used but the most giggles and laughter came from when the false eyelashes were applied and then the red lipstick.
“What a great costume,” the girls all gushed. “All you need are these,” she said holding out a pair of patent red 5" spike heels. “We all chipped in and bought them for you just for today.” Tommy sat down and put them on so the girls could have fun.
He stood up at their insistence.
“A little high for working in a beauty salon all day aren’t they?” he asked standing there now looking down at the red high-heeled shoes on his feet.
“But perfect for the everyday 60’s housewife look you are going for.”
Tommy was the spitting image of a 1960’s housewife. Round red button clip-on earrings were put on his lobes and a red string of beads was around his neck as the girls laughed at the sight of this now totally quiet,
feminized man.
The girls took pictures of him and then took turns having their own
pictures made with him.
He was such a good sport to let them do this to him on Halloween.
“Alright everybody, it’s almost time to open. Let’s see here what Tommy has today. You have Mrs. Hayes first for a shampoo and set. You also have Ingrid Thompson for a perm this morning.”
“That should be an interesting experience wrapping those perm rods with your long fingernails,” one of the girls quipped.
“He’ll manage just fine. Let’s see Laura is coming to have her highlights done. You also have Mark for a haircut just before lunch.” The girls were all laughing at the mental images of him doing these women dressed as he was.
“Then you have three shampoo and sets in the afternoon from that lady’s church group that like to stop by on Friday.”
Tommy looked at himself in the mirror. He felt a strong sense of apprehension and wished now he had not agreed to do all this. Then he was asked to turn around and Marie put a pink apron over his curlers and let it rest around his neck. She then tied it in the back. The apron was trimmed in white lace ruffles and had the slogan, “Real Men Wear Pink” embroidered across the padded bust line. The girls had it made a couple of weeks earlier knowing he was going to do this today.
“Alright everybody gets your stations ready, I’m unlocking the door.”
Between clients being serviced and those waiting for their appointment, the room would soon be filled with as many as twelve people at a time. Tommy knew he would be the topic of discussion today and he wasn’t sure he was ready to be the object of entertainment for this Halloween, but it didn’t matter now, he was dressed as a woman and it was time to let everybody else see him.
The first person in was one of Marie’s regulars. She knew everyone in the salon and when Tommy walked out with towels she looked at him and asked Marie, “Is that Tommy?”
“That’s Tommy alright,” Marie said walking with her to the shampoo basins. “He’s dressed as a 60’s housewife for Halloween,” she said checking the temperature of the water.
“I can see that,” the woman said staring hard at the image she was seeing. “Rather an ambitious-looking costume if you ask me. I can’t imagine a man letting himself look like that even for Halloween. I mean
I know it’s for fun but still, he’s wearing a dress and high heels.”
“Yes, he is,” Marie said with a smile as she reclined the woman back for her shampoo now.
Tommy’s first customer Mrs. Hayes entered the salon. She looked about and asked one of the other girls where Tommy was today.
“That’s him right there Mrs. Hayes,” she said pointing at the ladylike image approaching her now with blushed cheeks of embarrassment.
“OMG Tommy. Aren’t you gorgeous,” she said in a loud excited manner.
“What a beautiful costume and you look very authentic wearing it,” she said as others joined in her enthusiasm.
“Well thank you, I think,” he said as he took her over to the shampoo basins to shampoo her hair.
“Trick or treating today are we? Did you do this all yourself?” she asked with an inquisitive tone. Like there was more here than met the eye.
“No. The girls did this. They have been after me to let them dress me up as a woman for Halloween,” he said reclining her into the sink.
“And you let them. They did a very nice job too,” she said as he rinsed her hair and began her shampoo. “You really look like a woman dressed that way, I mean I would not know the difference if I didn’t know you were really a man,” she said closing her eyes and enjoying the shampoo.
The first thing Tommy noticed was that in these high heels he had to bend over much further to work and it was a bit of a strain. He also had the padded bra to contend with. He had never had to look over a padded chest before, which added to the strain in his stance. Luckily he was wearing a girdle which helped support his back in these newfound situations.
“Are you comfortable being out in public dressed like this?” she asked as they walked to the styling chair.
“It’s for Halloween. I’m just doing it for fun,” he said putting a cape around her and getting ready to set her hair.
“Have you ever dressed like a woman before,” her curiosity finally
pushed her to ask the question.
Tommy laughed. “No, I always dress like a man.”
Tommy set Mrs. Haye’s hair in curlers and finally got her under the dryer.
Tommy went to sit down for a moment before Mrs. Thompsom arrived for her perm. He had just sat down back in the break area about to take the heels off for a moment when Linda and Morgan both came in.
“Oh no, no, no. Get up Tommy,” they both said pulling out of the chair.
“What do you think you are doing?” they both said giggling.
“I was going to take the shoes off for a few minutes before my perm gets here. Why, what’s wrong?” he asked looking at them.
“You are a 60’s housewife silly. You can’t take your heels off. You have to wear them all the time. That’s what women did back them. You can come in here and slip them off during your lunch break and rub your achy feet like the women had to do.”
“What? You expect me to wear these all day? How high are these heels anyway?” he asked looking at them.
“Five inches,” Morgan said, “They didn’t have six-inch heels in your size in stock, or you’d be wearing six-inch heels.”
“Are you serious? Five-inch heels are not designed to be worn all day doing hair girls.”
“Oh stop your whining Tommy. You can spend one day perched on high heels doing your customer’s hair. It won’t kill you. It’s Halloween, think of it as some gruesome torture we are putting you through,” the girls laughed.
“I’m starting to believe there is more truth to that statement than not,” Tommy said walking back out to the floor to get ready for the perm.
The same type of inquisitive question kept arising as the day went on.
Not just with Tommy’s customers but with everybody that came in. Most of them had a good time with Tommy’s appearance giving him credit for having the courage to wear what he was wearing in public.
One of the older clients just couldn’t understand how a man could dress up like this and prance around all day in a woman’s hair salon.
That is unless he was really gay. Real men would never consider such a thing. Old public perceptions and backward thinking always creep in somehow. Tommy never heard any of her remarks as her disgust was only shared with Morgan as she did her hair. The look on her face though was enough for Tommy to see her true feelings about his costume.
Mark came in for his haircut. He was a young man in his early twenties. He was a little uneasy at first seeing Tommy dressed as he was.
“Why are you dressed like that?” he asked as Tommy cut his hair.
“You know Mark, I have started asking myself the same question,” he said his feet aching in the heels.
“I mean I know it’s Halloween and all, but you look a little too good for your costume. A guy puts on a dress for a costume, you know that’s cool I guess, but dude, you look like a woman. Does that make any
sense?”
“More than you know Mark. I let the girls dress me up like this. It wasn’t my idea. They’re having a little fun.”
“Oh, that’s good to know. I thought you did all this at home and came to work dressed like this,” Mark said sounding a bit more relieved.
“No, just being a girl for a day.”
After Tommy had finished Mark’s haircut and the perm he was finally able to go into the break room and remove his heels. It felt so good as each show came off. Tommy rubbed his feet and toes through the stockings he
was wearing.
Marie walked in with Tonya as he was massaging his feet.
“It’s tough working in high heels,” Marie grinned as she got something to drink.”
“Yeah. It’s murder. You can’t tell me women wore these shoes to do hair,” he said looking to them for answers.
“No, just thought it would add to the experience,” Tonya laughed.
“Tonya,” Marie said abruptly, “You didn’t paint Tommy’s toenails,” she said in a mocked alarm manner.
“Well, I knew he was wearing classic pumps and his toenails wouldn’t be
seen, so I didn’t do them.”
“Didn’t do them? He is dressed as a classic 1960s housewife, he should have red toenails. What’s your schedule like for the day? Do you have an opening?”
“Now wait a minute, “ Tommy said nervously.
“I guess I could squeeze him in after lunch sometime,” Tonya said thinking about her schedule.
“Hey. Wait, I don’t need my toenails done. I have enough costume on right now.” Tommy said looking at them still rubbing his feet.
“I guess you are right. I should have painted his toenails red yesterday when I did his fingernails. I can do them today if he has time between clients,” they continued their conversation ignoring Tommy’s objections.
“If you can’t work it in today how about tomorrow,” Marie asked her.
“Yeah, I can definitely do his toes tomorrow. That would be better actually because it would give me time to paint them and for the nail polish to dry,” Tonya agreed.
“Tomorrow? Halloween is over tonight. We’re not painting my toenails red tomorrow,” Tommy said in a panic now.
“Don’t you want to start dressing like a woman at work Tommy?”
The girls looked at each other and then burst out laughing. They were just messing with him. Marie unrolled one of his curlers that was a little loose and then rolled it back more firmly.
“Your hair set appointments will be coming in shortly, best finish your lunch. And if you are done rubbing your feet, put the high heels back on. A 60’s housewife needs to be properly perched up on her toes in high heels.” She grinned and winked at him as she went back on the floor.
“Yeah, yeah,” he said slipping the red pumps back on his feet.”
It was more of the same the rest of the day as clients came in to see him for the first time. It was easier for Tommy as the day progressed. He had heard it all now. The surprise and the shocked looks. In the end, Tommy was a very professional hairdresser and took his seriously clients taking care to give them service the he expected from him, no matter how he looked.
After the day was over the girls had one last request.
“I want to do a comb out on your set Tommy,” Marie said turning the chair for him. “Let us get some pictures of you with your hairstyle.”
“It’s been a long day girls, I mean I’ve been through a lot and I’m
tired.”
“Tommy please,” Morgan said, “You will never be doing this again, let us finish you out and get some pictures.
Tommy said nothing and sat down in the chair after taking off the frilly apron he had been wearing all day.
The rollers were removed and his hair was teased wildly and sprayed heavily before being tucked and patted into place. The hair was teased high on top and wide on the sides. The hair swept up high on one side of his forehead ending in a gentle curl on the other side of his forehead. Curls uniformly lay flat on both sides of his head.
Marie picked up a red bow and ribbon. Tommy started to say something as the girls started to laugh knowing Tommy was about to have bows put in his hair, but he said nothing and sat quietly while his head was tilted to one side and he felt the Bobbi pins being pushed into place holding the bow.
She turned Tommy to face the others. They all clapped their hands.
“You look great Tommy, you really do,” Morgan said taking the cape from around his neck. Come over here and let us get some pictures, and then we will get one large group photo.”
“Give us a big smile Tommy and say cheese,” Marie said.
Tommy smiled for many pictures. Pictures that would be on the bulletin board for clients to look at for months to come.
Tommy reflected on that Halloween from time to time. The girls occasionally teased him about how pretty he looked in his costume, but it was a fun day for the girls. Maybe not as much for Tommy, as his
nervousness and embarrassment were his own, but he was a team player, and that showed through. The girls were loyal to him and they became even tighter after his day in the salon dressed as a woman.
