© 1995

Bob was a security guard at the local mall. He enjoyed his work, and liked to meet different people. his bosses had no idea that inside he was really a pervert, wanting to peek at teenage girls in the dressing room. But being scared he would get caught, he never fulfilled his fantasies while at work. But if he did see a cute one, he would follow her around while she shopped, undressing her with his eyes, and then think about her as he masturbated after returning home at the end of the day.

One day, he saw a young teen getting dropped off by her mom in front of the mall. He saw instantly how cute she was. She was about 16. She looked a little older physically, but when she smiled she had a mouth full of braces, which made her look somewhat younger in the face. She had on tight blue jeans, and a VERY tight t-shirt. Her chest was small, but he could see every bulge her breast created. He could even see the outline of her bra when he stood behind her. She had the cutest braces that he’d ever seen on a teen. They made her not look like a silly kid, but rather “distinguished” he thought. Her mother joined her a few minutes later, and he followed them around for a little while. The mom finally had to sit down and get a drink, and the girl went over to look at some underwear in a store. He walked up behind her, and she sorta jumped when he said hello.

“Finding everything okay?” he asked.

The girl nodded yes.

“I’m Bob.”

“Amy.”

“Enjoy your shopping Amy. I’ll keep an eye on you today.”

She smiled, and he could feel his erection growing as he stared into her eyes.

He “accidentally” ran into her again later that afternoon, while she was alone again. The two of them talked, and she was a chatterbox as she told him all about herself.

“These girls love to talk” he thought.

The whole time Amy told him about herself, he was undressing her with his eyes. He wondered what those tits would look like. How much hair would she have. Is she a virgin? So many questions he would ponder tonight, as he did his thing. Between all the bullshit she was yakking about, he finally pieced together enough to be happy with how well he knew her.

She was indeed sixteen, and a cheerleader. She had no boyfriend, and from the way she talked, was a virgin. She liked movies, pizza, and TV.

“Well, you seem very nice.”

“Thank you. You’re nice too. Not many guys listen as well as you did.”

“I would love to see you cheer.”

“We have a game tonight!” she blurted out. “I’d love for you to come see me.”

He turned red in the face, but she sat and smiled at him, waiting to hear what he would say. He figured that he might as well give it a shot.

Bob was tired of jacking off all the time, and wanted to see how she would react.

“Well, Amy, I just have one small problem. I should not tell you this, but I am not really a very nice man. I think nasty thoughts sometimes when I see girls your age in those outfits.”

Amy blushed and whispered, “That is okay. I feel the same way about men in uniforms.”

Bob grinned, and told her he would think about it.

“Come see me, I’ll do some special cheers for you. Before and after the game.”

He confirmed that he would be there, and smiled as she walked over to her mother.

That night, he went to the football game, and sat on the bottom row. Amy was in her red and black uniform, and looked very cute. She looked more sexy than she had at the mall that day. She walked to the bleachers, and secretly handed him a note.

It said:

This next one is for you!

The next cheer, at the very end, she did the splits. She went all the way to the ground, and when her crotch hit the grass, she rotated her hips, and winked at Him. It was subtle enough that no one else would notice, but he began to breathe heavy. He could feel his penis getting hard. “Wow!” he thought.

After the game was over, he sat in the bleachers till almost everyone was gone. After what seemed like forever Amy came up to him, and asked, “Can you give me a ride home? My parents had to leave early, and I told them I had a date after the game. It is now 9:30, and I don’t have to be home till midnight. Do you want to go talk?”

Talking was the last thing on his mind, but he told her sure. She said to meet her by the locker rooms in 15 minutes. He went over there, and sure enough, just like she said, she showed up.

“Let’s go inside” she said.

He wondered what was up, but she opened the door.

“I stole a key from the coach tonight,” she said as he entered the locker room.

He looked around, and smelled all the perfume. It was the girls’ locker room. It wasn’t much different from the guys’ he had been in as a teen. Same lockers, showers, and benches.

Amy locked the door behind them, and sat down on a bench. He sat down next to her, and the two of them talked for a few minutes. Then he told her how uncomfortable he were being there with her.

“I know this must be weird, but I didn’t know where else to go.” Then she asked him, “Did you want to kiss me at the mall today?”

He stuttered and tried to avoid the question.

“Come on, tell me, did you want to kiss me?”

“Yes.”

“Would you kiss me now?”

“Of course.”

“I’m ready to become a woman tonight. I love you and want you to be my first.”

He leaned forward, and pressed his lips to hers. Her braces poked his lip a little, but he didn’t care.

He was getting hard as she slipped her tongue into his mouth. His reaction was quick, and he did the same to her. He placed His hand on her knee, and began to caress her inner thigh. She didn’t stop him, and just continued to kiss him. He raised his hand higher up her thigh, and under her skirt.

She took her mouth away from his and said, “It’s okay, I have on panties.”

She began to kiss him again and he put his hand over her crotch. It was moist, and he wondered how far she would let him go.

He worked his way up to the top of her panties. He pulled them away from her stomach, and lowered his hand inside. She kissed him harder as he felt the thin hair on her pussy. He slipped his hand farther inside, and began to rub her wet slit.

Before he could stick a finger into her, she stood up in front of him. “Let me take these off!” she said. She pulled down her panties, and he looked at them around her ankles. They were white, and had a wet spot in the crotch. She stepped out of them, and he raised her skirt up. She was directly in front of him, so he leaned forward to kiss her pussy. It had light brown hair on top, very thin, but very sexy. As he kissed her cunt, she held her skirt up for him. He reached under her shirt, and unlatched her bra. As he ran his hands to the front, the bra pulled away from her breast.

They stood in place as he cupped his hands around them. She lowered her skirt, and pulled his head away. Then she removed her top, and posed for him.

“Want to see me naked?” she asked softly.

“Oh god yes!” was all he could answer.

She unzipped the skirt, and took it off also.

His dick was pounding as this hot cheerleader stood bare before him.

“You are beautiful!” he told her, as she got on her knees between his legs.

She began to unzip his pants as he massaged her breasts. Her nipples were small and hard as rocks. She got his pants undone, and reached inside. Her small hand wrapped around his dick, and she pulled it out. It stood strait up as she held on to it.

“God damn it’s big!” she said. “I thought it would be smaller.”

“Is that good?” he asked.

“Yes, definitely. I’ve never given a blowjob before, so this would be my first time. Let me know how I’m doing.”

“As long as you want to give me pleasure, I’m sure you’ll do a good job.”

She lowered her mouth onto his penis, and the warmth was overwhelming. She was new to this, but oh was she good. She sucked his head for a little, then put the shaft into her mouth. She took it in deep, raising her head up and down, she must watch a lot of cable TV. Finally he told her she would have to stop. He was about to cum.

The teen stood back up, and sat on Bob’s lap as he began to kiss her again. He rubbed her pussy and inserted a finger into it. She moaned, and leaned her head back as he sucked her tit and fingered her virgin pussy.

He said he was ready, and he was going to take her virginity now. He pulled her over his lap, straddling and facing him. He held his cock as she slowly lowered herself down onto it.

She began to pant as his tip pushed its way between her engorged lips.

“This will hurt a little at first. But once it’s in, the pain will quickly subside. Try to relax, if you clench it will make it more painful.”

He put his hands on her shoulders, and as she took a deep breath, pulled her down quickly on his hard cock. His cock had penetrated about three inches into her unbelievably tight cunt.

Amy let out a scream, but he held her on tight. After a moment of sitting there, catching her breath, she began a tentative up and down movement. Her young, tight pussy was squeezing his dick with it’s tightness. He watched her ride him, and kissed her again.