You know several things that are a fact. The first is that the restaurant that your parents want to go out is considered high class. The second being that you don’t really like the place, but since your parents hardly ever go...really only about once a month…you figure you can tolerate it for one evening. The final thing that you realise is that you’ll need to change your clothes before leaving to go out for the evening.
Torn between dreading the evening ahead and how things will look, you start up toward your room. Inside you find that your mother has laid out a set of clothes and picking them up you notice that something is different about them.
The slacks look the same; black with creases down the front. But the shirt looks off and picking it you see why.
Pearl buttons on the front greet your vision and unfolding it you see that it is powder blue in colour and the sleeves are more puffy and airy. “Am I to wear this for the entire evening,” You ask yourself.
Setting down the blouse, as you’ve come to think of it, you notice that your black loafers have been also set out and next to them are two more articles of clothing. Picking one of the two up, you feel the silkiness on your fingers and the thought, “Pantyhose,” flashes through your mind and you drop the stockings to the bed.
Picking up the final garment, you unroll it and notice that it is a pair of boxers. It takes you a bit to put together what looks off, but finally you realise that they could be boxers either worn by a boy or a girl.
Setting them down, thinking about how strange things have just gotten, you hear a voice behind you saying, “Make sure you take a shower and fix your hair before we leave.”
Recognizing it as your mom’s voice, thinking that she is talking to Sally, you say nothing, still looking at the clothes on the bed. After a couple seconds, your mom asks, “Did you hear what I said?”
Turning, you see your mom standing in your door and coming to the conclusion she was speaking to you and not your sister, you nod and tell her, “Yes ma’am.”
She nods and turns to leave, but you stop her by asking, “Do I have to wear this?”
She turns back and tells you, “Yes.” And turns to leave once again, probably to deal with Sally and the ruckus she was making.
Stepping forward, and without thinking about it, you ask, “Mom? Do you think I can wear a dress? Just for this evening,” and then you wait with baited breath as she slowly turns to look at you once again.
Seconds drag out and you feel like you’re waiting for hours for her answer and as you wait, the question, “Why did I even ask that,” flashes through your mind. After what seemed like forever…really it was only like thirty seconds…you mom smiles and asks, “Is that what you want to wear tonight.”
A feeling of trepidation creeps over you and nodding, you tell her, “Yes ma’am.”
She smiles and starts to raise a hand…almost as if she was going to ruffle your hair like she did before…but instead she smiles, mumbles something that sounds like, “My little girl is growing up,” and the tell you, “You haven’t worn a dress since you were younger. Before you tomboy faze. I’m sure we can find you a dress for this evening. Maybe one of Sally’s. And then, if you still want to continue wearing dresses, I’ll take you shopping tomorrow. Okay?”
You nod at this and your mother leaves. Asking yourself, “What have I gotten myself into and is this all part of the wish,” you sit down on your bed.
After a moment, you stand and head to your closet to find a towel. Finding one, you head for the bathroom, passing Sally in the hall, and inside you shut the door and begin to run the water for a shower.
Afterward, you return to your room, the towel wrapped around you like a girl normally has a towel wrapped around her. On the bed you see a dress and picking it up you see that it is all one piece. Medium blue in colour, you can right away tell that it would probably fall just past your calves. Fingering the spaghetti shoulder straps, you see that it zips up in the back.
Wondering if you can go through with wearing a dress, you close your bedroom door and letting the towel drop to the floor, you stand in front of a full body mirror and hold the dress in front of yourself.
After standing like that for a bit, thinking over and over, “I’ll look so cute in this,” and “It’s so me,” you drop the dress on the bed and instead pick up the boxers. Looking at them, you set them down and instead pick up the dress and returning to the mirror, you slowly begin to pull it on.
Afterward, you open the door and automatically head for Sally’s room and finding your sister there, you ask, “Can I borrow a pair of underwear and can you zip me up in back?”
You sister looks at you from where she is sitting, huffs in mild agitation and makes a motion to the top drawer of her dresser. Thanking her, you sift through the pile of undergarments, wondering if they’ll fit and which one will fit. As you do this, Sally comes up behind you and zipping up the back of the dress, she asks, “You giving up the tomboy look.”
Suddenly feeling shy, you shrug and tell her, “Maybe. Maybe I want to try something new,” and select from the drawer a pair of pink underwear you know to be bikini briefs. As you turn to leave, Sally stops you and tells you, “For what it’s worth, you look really pretty like that.”
You blush and another feeling of shyness washes over you and mumbling, “Thank you,” you exit the room and return to your room.
Tucking your penis and testicles back, you pull on the underwear and then after that the pantyhose. Next to your loafers you find a pair of low-heel spaghetti strap shoes and pulling them on, you turn back toward the mirror.
Looking into the mirror, you are torn between liking the way you looked and wondering if people would see a boy in a dress or very pretty girl. Deciding to ask your mom, you exit your room and make your way toward her room. Standing in the door, you watch as you mom finishes her outfit with a pair of earrings and seeing you, she beckons you in.
Walking over to her vanity, she tells you, “You look very pretty tonight,” and then gently begins to pull a brush through your hair.
Unsure of what to do, liking the feeling of the brush going through your hair, memories of your mom doing this when you were younger flooding through your mind, you just nod and sit quietly. Afterward, your mom fashions your hair into a short braid.
After that, she gives you a spritz from one of the many perfume bottles on her vanity and the gently applies a light blushing of make-up to your lips and cheeks. Looking in the mirror, you see a very young a pretty girl reflected back. Something tells you that that you are still male, but you don’t care. Your musing is interrupted as your mother tells you, “You would look pretty if you had your ears pierced,” to which you once again felt a sense of shyness washing over you.
Nodding, you look to your mom and ask, “Am I really that pretty?”
Your mom nods and then tells you, “Yes. Yes you are. Know. Why don’t you go downstairs to wait and I’ll be down in a minute. Oh. And tell Sally she should also be downstairs and ready as soon as I come down.”
Nodding, you glide toward the door and then after a minute you ask, “Can I get my ears pierced tomorrow?”
Your mother tells you, “We’ll see, but probably yes,” and nodding, you exit the room.
Walking back to Sally’s room, you stand in the doorway until you have her attention and just as you are about to tell her mother’s message, she toss something to you and says, “It goes with the dress.”
Unfolding it, you see that it is some type of wrap and immediately the word ‘Stole’ flashes through your mind. Thanking Sally, you tell her mother’s message and then turn and start downstairs. As you sit on the couch, waiting for your mother and Sally, wrapping the Stole around your shoulders, wondering if your father is going to say anything about the way you’re dressed, you notice, rather oddly, that your thoughts have been slowly shifting to a more feminine frame of mind.
Unsure of what this means, you instead sit on the couch, crossing you legs unconsciously, trying to sort out what all is happening and how it is tied to your wish. After a bit, your mother joins you and then Sally. Lastly your father, who says nothing about your appearance, comes home and all thoughts of the wish are driven away as you, your mother and father and your sister head out for dinner.