Caleb's best friend's sister, Regina, was every boy's dream. She was tall, slim, and built for sex. That's what Caleb thought. She was the captain of the high school volleyball team, and Caleb had a major crush on her.

Regina knew how he felt about her and let him crush on her. She had plans for him, and she needed him to be as helpless for her as possible. She actually liked Caleb, but she needed him to be compliant.

Caleb, on his part, is a shy sixteen-year-old who would do anything if Regina simply asked him to.

Regina knew how Caleb felt, and she knew he was ready for what she wanted and invited him over to her house.

When Caleb arrived, she took his hand and led him to the basement. The rest of the volleyball team was waiting for them.
Caleb looked at the twelve girls all sitting there; a couple of the girls had their legs spread, and Caleb could see they weren't wearing panties. Like any male would, he immediately got hard.

Regina led him to the middle of the girls and forced him to his knees. She smiled at him and told him, "We're going to make you one of the girls."

Caleb didn't know what to say, but he was ready to obey. One of the girls stood up and knelt before Caleb and started to apply makeup to his face. Another girl placed a wig on his head and styled it.

A third girl removed his shirt and put a bra on him. She stuffed the cups with foam to make him look like he had breasts. She put a blouse on him.

Regina sternly told him, "Stand up, remove your pants and underwear, Sissy. NOW!"

Caleb did what she said. He heard one of the girls moan when she saw the size of his erect cock. She said to Regina, "We need to keep this one."

All the girls agreed.

With his makeup done, Regina ordered him to put on a sexy pair of panties, a skirt, and thigh-high hose.

Next, he was ordered to step into a pair of high heels.

All the girls agreed that Caleb's slim body and bubble-shaped ass made him resemble a passable and pretty girl. Even Caleb felt like a girl. One by one, the girls kissed him and stroked his cock under the skirt. The last girl dropped to her knees and started sucking his cock.

Caleb was beside himself with excitement. Regina asked him, "Do you want to continue being our sissy?"

Caleb just moaned and nodded while he came into the girl's mouth. She slapped his ass and kissed him with a mouth full of cum. She pushed Caleb's cum into his mouth and told him, "Next time, warn me, sissy."

Caleb noticed Regina had put on a strap-on. As she walked toward him, Caleb knew what was going to happen. He got on his knees and bent over. Regina got between his legs and put the head of her 'cock' against his virgin rosebud.

Caleb felt the cold of the lube on the strap-on and tried to relax the best he could. He felt the silicon cock spreading his tiny hole as Regina slowly pushed the dildo into him. He felt Regina's bare legs against his and moaned as Regina slowly withdrew.

Caleb felt his cock hardening as she continued to fuck his ass. Felt his pleasure increase with each thrust. One of the other girls, who was naked, positioned herself underneath him. She pulled his head to her pussy as she took his hard cock into her mouth. Before she did, she told Caleb, "You don't need to warn me. Now eat me, Sissy."

Caleb knew how to eat pussy and didn't disappoint the girl below him. She thrust up and came just as Caleb filled her mouth with his cum. The girl slipped out from under Caleb when she recovered and fed his cum back into his mouth. She smiled at Caleb and said, "I am going to teach you to suck cock, Sissy. It's a girl's job to be a good cocksucker."

Regina helped Caleb stand up and said, "From now on, you will be dressed like you are now around us, or you will be naked. Shave your legs and pits, Sissy. We're going to get you hormone treatments to grow your own breasts. From now on, your name will be Cassandra. Sissy, you won't miss any of our games, or you will be punished. Sissy, you will be sitting with us for everyone to see."

Caleb smiled and replied, "Yes, Mistress."