Tom Learns How to be a Bitch
Gina Schwarz
Copyright M. Foster 2011
Smashwords Edition
Most typical Friday nights between friends at the bar end in the typical fashion. The typical drinks lead to typical boasting and the morning sees a typical hangover. This Friday night was no different than many others in Tom’s life. A skinny man and part-time model, he took great care in his appearance, swimming regularly, and much to his friend’s amusement, getting the occasional manicure.
“You’re full of shit, Tom,” said Gary, “there’s no way they can score twice before the half.” Gary was Tom’s college friend. Gary was an imposing figure, dark hair, stubble and a barrel chest from years of football. The two roomed together for a year, but parted ways, Gary going to live with his football teammates and Gary with his girlfriend. Their ritual for keeping in touch was to have a few drinks every Friday.
Tom shot back, “It’s happened before, it’ll happen again! Want to make a bet on it?”
Gary looked straight at Tom, a glimmer in his eye, “Yes. $300 if you win.”
“And if I lose?”
“You’ll be my bitch for a month.”
“Whatever,” Tom rarely took these bets seriously, especially with Gary, “You’re on! Anyway, it’s getting late and I’m getting drunk, so I’d better head home. See you later.”
“Don’t forget our bet!” Gary shouted as Tom left.
###
“Wake up, darling,” chimed Mary, Tom’s girlfriend, “we’ve got a big day ahead of us!” She stood at the foot of the bed, dressed for the day in a pair of jeans and a tank top. She was a real looker, even for being 24; she was thin with blonde hair down to her shoulders and an almost-perfect face that no man could say no to.
Tom replied groggily, “It’s Saturday…what are you talking about?”
“Well, first we have to get you some new clothes, a haircut, a waxing, some makeup--”
“Wait, what?”
“Oh! Your bet with Gary! He told me all about it! I remembered how you told me that you liked to be submissive in bed, so I thought this was a perfect opportunity to see exactly how submissive you like to be.”
“No way, you know, fuck, GARY knows I wasn’t serious about that. Is this some kind of joke?” Tom asked.
“Oh, no, honey, it isn’t. I know it doesn’t sound fun now, but I promise that we’ll make the best of it, besides,” a cruel smile crept across Mary’s face, “if you don’t play along then I can show your boss the pictures from last time we got you dressed up.”
Shit, the pictures! Tom had never imagined that this could happen to him. Mary had dressed him up in her clothes before, and he had just told her that he thought transsexuals and girls with strap-ons were hot. It was always a fantasy, and one that Mary had been willing to play out in privacy, until now. It was exciting, humiliating, and upsetting all at the same time.
“Gary is over in the next room, and I think he has some things he’d like you to get started with. Let’s get you dolled up so you can get started.”
###
Tom stood in front of the full length mirror in the bedroom he and Mary shared. He gazed into the glass and felt his face burn with embarrassment. Mary’s clothes fit surprisingly well. Her 4 inch heels kept him in an unfamiliar posture, and it was strange feeling to be wearing makeup and actual women’s clothes. Mary really had done a fantastic job of transforming Tom. A plaid skirt and tight white turtleneck concealed a black lacy bra, panties and a garter belt underneath. The only clue was the black leggings. Tom could barely believe it, “Is this how I really look as a girl?” his cock throbbed in the panties, pitching a tent with the skirt, “I’m pretty hot!”