Dress up

"Okay mom I will do it your way" you say reluctantly.

"Don't sound so glum Doug, now try those panties on for size." your mom replies sternly.

You gulp and look at the pile of clothes she has laid out for you. You pick up the panties which are light pink with a cute bow detail on the front.

You slide them up your legs and are greeted by an unfamiliar but not unwelcome sense of silkiness that caress your thighs and crotch. You tuck your penis so that they fit however you still have a slight bulge but nothing as big as it would have been if one of your sisters had been wearing them.

"The pantyhose come next Doug" your mom says encouragingly.

She shows you how to roll them up your legs without laddering them. You again let the wave of silkiness wash over you and soon find yourself idly stroking you legs.

"You know your lucky Doug. Not having leg hair has saved us time shaving".

You don't feel all that lucky at the moment and start to pull on your dress. It is a black and white striped sweater dress.

"Now your dressed lets get your hair and makeup done." your mom says

You consider protesting but you think better of it and allow yourself to be led to your mother's bathroom where she starts to apply some light make up and styles your hair in a girly fashion.

"We don't want to overdo the makeup on the first date" your mom says absentmindedly, still applying your make up. "We don't want your date thinking you are a harlot."

You open your mouth to object but she simply slaps you on the head lightly.

"Stay still, you'll ruin your lips."

You let her continue and she finally steps back to admire her handiwork.

"Oh my." she gasps "You really are beautiful" her eyes start watering. "My little boy is growing up".

You turn to the mirror to see what has driven your mom to tears and you are knocked speechless by your reflection.

Your mom is right. You are beautiful. Even more beautiful than either of your sisters and possibly even Tiffany.

After you mom stops gushing over how pretty her only son is, she claps both hands over her mouth and gasps.

"Oh silly me, in all the excitement I forgot your shoes. Head over to your room and i'll bring them through".

You do as you are told, still reeling from your transformation.

As you wait in your room, you watch your reflection in your cupboard door mirror. You examine your body and its curves in the mirror.

You are in the middle of a particularly daring pose with your ass out and back arched when your mother walks in.

"Enjoying yourself honey?"

You jump and look guilty

"I was just err" you start

"Don't worry Doug. I'm not judging you, i'm proud of you. Look how pretty you are. You'll be turning more than your date's head tonight I can tell you."

She places a simple pair of black ballet flats with a little boy detail in front of you.

"I know heels would be preferable but we don't have time to teach you to walk in them. These flats are cute enough anyway." your mother says.

Without a word you try them on. You have to admit they are indeed cute and quite comfortable.

"Is that it?" you ask.

"Yep you are ready for your date." your mom looks at you expectantly. "Well? Aren't you going to thank me?"

"Erm, thank you mom." you say meekly, too embarrassed to admit you are impressed by the transformation. "I do have one question though."

"Go ahead Doug" your mom says smiling.

"Where did you get the clothes?"

Your folds her arms and chuckles slightly. "I've always had some clothes set aside for you since you were twelve. I kept them just in case you finally got a date. Of course they were boys clothes until to you were fourteen but as it appeared you had little interest in asking a nice young girl out, I thought more feminine clothes would suit you better. Let me ask you a question now. Did you ask the girl out on the date or did she ask you?."

"She asked me" you mumble.

"I thought so" she says triumphantly. "A mother is never wrong. Don't look ashamed Doug, its just who you are. Some people lead, others follow. Look at it this way. With more girls feminizing their boyfriends you can be considered to be ahead of the times. A truly modern gentleman."

To your relief the door bell rings.

"Oh sounds like she is here. Go and answer it Doug. Don't keep your date waiting."

You head down the stairs and tentatively open the front door, still conscious of what you are wearing.

On the other side you see...