From Nerd to Cheerleader

[SasssySlavePuppy]

Taylor was a gorgeous specimen of a human being, if only he had been born a girl. Five foot, seven inches tall and weighing in at about 145 pounds of tanned skin, his blonde locks falling in natural waves just below his shoulders. Instead, Taylor was too small for athletics and too focused in being intelligent to notice anyone anyway. He had made it to college without dating anyone, playing sexually explicit games online and exploring kinks on various sites. One day, he had stumbled into a chat room and met Chelsea.

Chelsea, it turned out, was a cheerleader at the same college that Taylor attended, and in fact, was only a year his elder. After weeks and weeks of putting off a meeting, he finally agreed to have dinner with Chelsea to discuss a few problems she was having with Chemistry. So after finally getting over his fear, he was finally going to meet a girl for real.

Chelsea, however, had no intention of studying chemistry with him, or at least, not in the traditional sense. She had just broken up with the star basketball player at her school, finally getting sick of feeling like a nobody, and always feeling like a piece of meat and not an actual human. She was a very kinky individual anyways, and had been satisfying those urges with various cheerleaders who were like minded. And then, she stumbled upon her revenge in the form of a novice kink who had never had a girlfriend. He had even sent a picture, and Chelsea was astounded by his resemblance to hot blonde cheerleaders and not to males.

That evening at dinner, Chelsea was dressed in bright pink leggings and a black crop tank top, her flat stomach peeking out. She sat at a table, picking at the salad she had made from the salad bar as Taylor nervously walked over.

“He-hello”

“Hi Taylor, take a seat. It’s nice to meet you in person. Your hair is beautiful”

“Oh thanks. So what is your Chemistry problem?”

“Oh you know, repulsion and attractions and quantifying them. The usual struggle.”

They talked more about chemistry and what not, and then Chelsea asked if they could go to her apartment. He agreed and five minutes later, Taylor found himself in a room full of patterned fabrics.

“ not what I was expecting. Where is all the pink?”

“Oh Taylor, why must girls have pink? Do you like pink?”

“Idk, I think so.”

Chelsea smirked. Soon, Taylor, you will love pink, she thought to herself.

“So, Taylor, you don’t seem all that shy.” She said, ripping her shirt over her head and throwing it into the hamper, followed by her leggings, sports bra, and thong. “How have you never had a girlfriend? You seem like a catch. Brains and beauty. Perhaps, you secretly knew you wanted to be a girl?”

She stood naked in front of him, hands on her hips. She stared intently at him, then down at his crotch. No difference, she thought to herself. Good.

“Taylor, I need your help doing something and I have a feeling you are going to love it. You see, my ex is an asshole, though what masculine macho athlete isn’t. I need to get him back for humiliating me on Valentines Day, taking me out to dinner only to break up with me as if we were Elle and Warner.”

“Well, where do I come in”

“You are going to be my humiliation for him. Follow me.”

They walked into the bathroom and Chelsea forced Taylor into kneeling position in front of the body length mirror, pulling his shirt off. Then, she tied his hair back in a tight ponytail. “Look at that, you would be such a beautiful girl. Are you willing to explore the sissy kink with me, I know you had talked about wanting to know what it is like to be a girl. Let’s see where we can go with it.”

“Ummmmm, I didn’t think it would happen so fast.”

“But tell me you want to try. You know you do, deep down. And as a reward, you will get to try all of things you ever dreamt of.”

“Ok.”

“Good girl. And the good news is, you already have a girl name, so that is easy. But let me just show you how sexy of a girl you can be.”

Two hours later, Taylor was standing in front of the mirror, Chelsea turning him to face the mirror and take it all in for the first time. What he saw was astounding and made his cock hard in its new cage that Chelsea had locked on him. He stared into the mirror at his tight ponytail, the make up that took his smooth male face and turned it into the face of a sexy woman with red lipstick. He saw for the first time what he looked like in a skin tight dress, the bra and fake boobs on his chest making him look like a woman. In short, if he didn’t know he was a he, Taylor would be convinced he was a girl.

“On your knees, slut.” Taylor did as he was told but noticed a Chan he in Chelsea’s demeanor. She seemed much more aggressive now. That was when he noticed the strap on hanging in front of his face.

“Suck my cock like a good little slut.”