Becoming A Sissy

chapter 2

A week had passed since Tom first met Sarah. He had wore her panties and bra every night. The feeling of wearing women clothes gave him a unique pleasure.

Tom laid in his bed scrolling through social media, when he got a text. It was from Jeff. Tom was horrified it was multiple pictures of him dressed in women's underwear. Jeff texted again.

I have a proposition. In exchange for not posting these pictures and humiliating you, you will pose as my girlfriend for a dinner with my parents. Do we have a deal?

Tom's hands were tied. He couldn't let anyone see those pictures, so posing as someone's girlfriend was the only option. He texted back that he agreed, and after a while Jeff sent another text.

Glad to see you agree. Chuck and Kyle leave home tonight, so we will begin training tomorrow.

Tom was anxious the rest of the day thinking about what Jeff had in store for him. Eventually morning came and Tom had calmed his nerves. He got dressed and exited his room. Jeff was on the couch chatting with a woman Tom had never seen before.

"Finally. Let's begin your training." Jeff said. "This is my sister, Helen. Today we'll just be focusing on your appearance. Any questions?"

"Yes. Why don't you just get an actual date?" Tom asked.

"We both know neither of us have ever gotten a girlfriend."

"Can you at least be gay? So I don't have to dress as a girl."

"I already told my parents I had a girlfriend not a boyfriend. Anything else?" Jeff asked. Tom shook his head. "Great. Helen will be in charge of your transformation. Disobey her and the whole world will know you wear women's underwear." Jeff left to his room.

Helen got up from the couch. She wasn't tall, but like most people she was still taller than Tom. "Strip. I want to see what I'm working with." She commanded. Tom wasted no time in obeying her.

"Your physique is already feminine and you only have hair on your legs. This should be easy." She paused and grabbed a pink bag from behind the couch. She reached in and pulled out a razor. "I'll help you your first time, but pay attention, so you can do it next time."

She walked over and got on her knees.  She slowly glided the blade across his legs. Tom noticed she was going with the hair's direction. After awhile she finished shaving his legs and started admiring her work. Tom ran his hand down his leg. He quite liked the smooth feeling of his legs.

She opened the bag again and this time pulled out a long black haired wig. "Come here." She beckoned. Tom walked over and she placed the wig on his head. "Looking sexy Tom. Ugh Tom is such an ugly name for a cute girl like you. Let's call you Tammy instead."

"Fine." Tammy acted uninterested but she kinda liked it more than Tom.

"Let's get you some clothes. We'll start with some lingerie." She helped Tammy into a black thong and bra.

The thong wasn't as comfortable as Tammy's panties, but they made her feel sexy. The bra also made her feel sexy.

"Now the fun part, dress up time."

They spent the next hour trying on various outfits. The one they landed on consisted of a short sleeved crop top, a skirt that ended halfway down her thighs, and thigh highs.

"Care to take a look in the mirror." Helen said.

Tammy spied a gorgeous woman standing in the mirror. Her dick started to grow. Her bulge made it quite obvious she was a man.

"I'll deal with your dicklet after it settles down. In the mean time  let's practice walking in heels."

Tammy put on a pair of heels and took a step forward. She quickly lost balance and fell to the floor. After some practice she got the hang of it.

"Now that you can walk normally the next step is to learn to walk like a woman. Pretend your walking on a type rope and sway your ass."

Tammy gave it a shot, and did as she was instructed. It wasn't terrible but a couple tries later and she was doing it perfectly.

They then practiced acting like a woman for sitting, standing, sleeping, laughing, talking, and even peeing. Tammy finally looked, sounded, and acted like a woman.

Tammy's dick had gone down, so Helen enacted her plan. She put Tammy's cock into a tiny pink chasity cage and locked it. She wore the key to the cage around her neck for safe keeping. Tammy was mad at first, but she quickly forgot the cage was even there.

Helen put on her final touches some padding in the bra and a little makeup. Then she left to Jeff's room.

Tammy could hear them whispering. She almost ease dropped on them, but thought a woman wouldn't do such a thing. Finally they both emerged. Jeff was stunned at how beautiful Tammy looked. Tammy started to blush. She could feel Jeff's gaze checking her out from head to toe.

"It's getting late. That's enough training for today." Jeff said.

"I'll send you a text with tasks you must do daily, and I'm leaving my pink bag full of make up clothes and accessories here for you to use."

"Yes ma'am." Tammy replied.

"Alright I'm off." Helen stated. She pulled Tammy in close and gave her a tight hug.

"Um Helen. Thanks for helping me." Tammy said.

"Don't mention it. I had a lot of fun and I'll be back tomorrow to help." Helen replied. She gave Tammy a kiss on the cheek and left.

Jeff had already left to his room, so Tammy retired to her's.