Dress Up Day
By
Julie D Cole

I guess I finally had to give in to mom since every year she’d badgered me to let her choose my outfit for school dress up day. She was certainly excited when I nodded and then uttered ‘OK’ as I left for school and told me that she’d ensure that it was the best day ever for both of us. Furthermore if I entered into the proper spirit she’d spoil me rotten for the whole weekend that followed that would involve a trip to my favorite Fun Park.

At school everybody was hyped up about it since we were pretty much left alone without any intense lessons and lots of chance to play around and make lots of noise. Nobody gave away the details of their costumes and I couldn’t anyway since mom hadn’t decided on my outfit yet and I hadn’t a clue what she’d choose. I just hoped that it wasn’t anything too outlandish or stupid since I was pretty shy and didn’t like to be centre of attention.

By the time I got home I’d had to guess just about everybodies outfit but not one person guessed mine, including me. What a shock it was so I flatly refused.

‘Come on Joseph you promised.’

‘Well I might have promised but that’s not an outfit and no way am I going outside dressed like that.’

‘Come on Joe just try it on for me. I couldn’t resist it and I’ve had my eye on it for weeks. You know that it will suit you. Don’t be frightened it’s for one time only.’

‘Oh yeah. I believe you but thousands wouldn’t. You’ve been wanting me to do this for as long as I can remember and I left all that behind me ever since the guys in my class saw the photos in the newspaper. I’ve never lived it down.’

‘Joseph Alexander that was years ago and most mums I know with sons and no daughter have persuaded their sons to have girly days sometimes. Especially Angela Hornshaw, Jakes mom. She told me that Jake often spends weekends as Jennifer.’

‘Yes and look what he has to put up with at school. Even the girls bully him now and I don’t intend that happening to me.’

‘Come on you spoilsport don’t be so miserable. It’s only a bit of fun and it’s all in a good cause. This year there is even a dance organized by the parents that means everybody can join in after school. I’m looking forward to a dance and to dress up. I haven’t been out for ages and I am getting past it. Come on just try it on for size in case I have to take it back or shorten it. I spend a lot of money on the dress and even more on the boots.’

‘Look mom I don’t mind the boots but couldn’t I just wear jeans.’

‘Well you could but they’re OK for boys but not for young ladies going to their first dance.’

‘That’s it then. I ain’t going to no friggin’ dance dressed like a Shirley and I don’t want to be frozen out like Jake.’

‘I’ll make it worth your while.’

‘Nothing you could offer would entice me to wear those things or that wig so forget it.’

‘Joseph you promised and I’ve spent a fortune today. How about I book driving lessons for you as a special treat since I’m really looking forward to see everybodys faces when we turn up. I can see us now. I used to be the school pinup and I reckon this is my chance to show a few moms why. How about it? Driving lessons?’ starter pack of six lessons with Greg Hant in his coupe.’

‘You’d have to make it ten lessons or no deal.’

‘OK then ten it is.’

‘Plus a car if I manage to pass my test first time.’

‘Come on Joseph that’s going too far. Be realistic.’

‘I am and those are my terms. If I’m going to be the butt of the jokes at school at least everybody will understand why I caved in.’

‘OK it’s a deal.’

‘Done.’

‘Yes I think I was so come on get a shower and let’s see how you look.’

‘Well what do you think.’

‘I look a right muffin in this dress and the boots I like. The heels are a bit narrow but they’re OK. I’ll be frozen stiff in this short skirt. Can’t I wear jeans it’s going to be freezing all week.’

‘Wimp. We manage so why not you? I can borrow a coat from Liz next door. She’s about your size.’

‘You must be dreaming again mom. What if Amy sees me. I’ll lose all my street cred.’

‘Oh you’ve got street cred have you. Growing up are we? Are you chasing after her then?’

‘Not exactly but I think I’d have no chance at all if she saw me parading about in her moms coat.’

‘Do you know Joseph Alexander you’re hard work. Here I am doing things for charity, for a good cause and you keep spoiling the feeling.’

‘OK I give in. No need for the saddo eyes. I’m in.’

‘Well just sign this contract then. Just a minute I’ve got a pen somewhere.’

‘Mom.’

‘I’m joking but it’s about time I got one back at you.’

………………………………………….

‘Well doesn’t that look nice? I couldn’t be more pleased. It’s like having a daughter at long last. Come on Josephine let’s see how you walk in those boots. Not like that you fool. Do it properly or I’ll make you dress like that for a week.’

‘I’m not carrying on if this is what it’s all about. This is just a dress up day at school and nothing to do with me being Josephine.’

‘Well a mom can dream sometimes can’t she? We could have had some great days out shopping. You like it anyway and just imagine what it would be like if you’d have been spoiled rotten. I do envy all the other moms.’

‘Well I’m sorry if I disappoint you. I’m quite pleased to be a boy and I always thought moms liked sons and dads liked daughters.’

‘They do but you must admit you make a wonderful daughter and you’d certainly have the boys chasing after you if you were a girl.’

‘If any come near me at school when I’m dressed like this then they’ll regret it. These are not real so if they try to fondle me I’ll kick them in the nuts.’

‘Josephine Alexander. Don’t you dare. You’d better act like a lady and no bad language if you don’t mind.’

‘Just let them try.’

Mom enjoyed herself prettying me up and commented on my smooth skin and hairless legs. I guess I was lucky in that department. The underwear was a bit uncomfortable but I soon found a way of reducing the discomfort but I’m not sure where it went to. Lucky I suppose considering the shortness of the skirt. That was another thing to consider. How to sit and how to cross my legs. Too many things to remember so I was glad to escape to bed. I had some weird dreams that night. I was made to sit with the girls at school and had to do ballet and tap dancing. I woke up in a sweat and was glad to find I still had the full set when I checked myself out in front of the mirror. Thank goodness the breasts had gone as well. Still in my dream they’d looked pretty good but a bit too big for ballet.

So Dress Up Day arrived. Practice that mum insisted upon had made perfect and she was delighted with her handiwork and the small details like the removal of the hair on my arms, the eyeliner, the effect of the face scrub and beauty mask treatment, the studs in my ears and the manicure. The shoulder bag matched the boots I was wearing.

I was still insisting to be called Joseph all the time she was referring to me as Josephine and then I stopped in front of the hall mirror whilst she went out to start the car. I was pretty hot for sure and was amazed at the resemblance to mom. As soon as she slipped on the wig she’d told me that this was meant to be and now she was certain we’d have lots of fun-time together. “what do you mean mom?’

‘Just wait you’ll see. Us girls are going to have fun.’

I checked the bag for a brush to put in place the stray hairs. Maybe this wasn’t such a bad idea after all and I spoke out softly to myself ‘I can do this.’ I looked like a lot of teenage girls rather than a boy in a dress. Maybe I had a lot of moms’ genes in me rather than dads. Maybe a touch more lipstick would have been better but then it’s not allowed at school. Perhaps I might ask mom to bring some for the dance when school rules don’t apply.

Mom honked on the horn and I hurried to the car slamming the front door behind me. As I sat in the seat and put my legs together to avoid showing all I’d got Amy appeared with her mom and waved. ‘Wow is that you Joseph. Wow you look fantastic. What a change. You’re sure to win first prize at the dance. Mom can I go with Joseph and her mom.’

Her mom? What’s this?

She got the approval so mom insisted we sit together in the back. We laughed and joked all the way to school and I could tell by moms glances in the mirror that she was so happy. Her eyes were leaking a bit and she reached for a tissue.

Amy showed me her outfit under her jacket. She was dressed as a Hooters girl and she certainly had gotten the hooters from somewhere. ‘Wow is that you?’

‘No silly mom loaned me one of her bras and her bust enhancers. They are pretty real don’t you think?’

She took my hand and let me touch her bust. Was I dreaming. ‘I can’t sorry it’s not right.’

‘Don’t be silly Jo it’s OK between girls. Can I touch yours.’

‘She was giggling as she said ‘Are they real? They feel natural.’

‘Amy no they are just some stick on things that mom glued on this morning. We didn’t want them to keep falling out. I’ll take them off later won’t we mom.’

She turned and smiled as she pulled up at the school gate. Then she giggled and reached over to kiss me whispering ‘Not tonight Josephine. Not tonight. - Go have some fun and you can tell me all about it later.’