Accept your mother's offer for help.

"Okay mom so what would you suggest I wear?" you ask.

"Well for starters, head to the bathroom and strip naked. We need to start from scratch". She says enthusiastically

Unsure of this but determined to look good for Tiffany you do as you are told. When in the bathroom you remove all your clothes and shiver slightly. Examining your self in the mirror you ponder your slight frame and girlish facial features complementing your shoulder length blonde hair perfectly. Even without tits you could pass for a girl pretty easily in the right clothes, you hadn't even started growing leg or body hair yet.

You hear your mom shout through the door.

"Doug. When you are ready, come to your room. I have laid out some clothes for you."

Slightly embarrassed at appearing in front of your mom naked you nervously open the door and make your way to your room as quickly as possible covering your penis.

Its lucky your sisters aren't home or they would have been in hysterics.

You open enter your room to see your mom standing next to your bed smiling.

"Try on your new outfit. Its not perfect but its much more appropriate for a date with a girl than what you were wearing before."

You look to your bed. Your heart sinks as you see the undeniable frills and lace associated with girls clothes.

"Mom Im not wearing girls clothes." You protest

"Nor shall you be" she says smiling sweetly "These are your clothes"

"But its a dress!"

Your mum sighs "Doug. Girls today aren't looking for their prince charming or night in shining armor. Thanks to the feminist movements, modern girls are more liberated and assertive. They want a trap boy who they can show of to their girlfriends. You can't be so ignorant, Sara leaves her Playgirls in your room all the time and they are full of feminized boys. Its just the way of the times at the moment. Just go with it, I can guarantee you will get the girl, just look at you. You are prettier than Crystal was at your age."

You blush at this and weigh up your options. If you go with it and someone you know from school sees you, you will never live it down. But on the other hand if your mom is right, you could have a sure thing here.