James was a security guard at the mall. At 24 years old, it wasn't the best job, but it was good enough to pay the bills while he went to the local community college. 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 rooms. But being scared of getting 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 teen getting dropped off by her mom in front of the mall. He thought she was awfully cute. She was about 18, but she looked even older physically. When she smiled she showed a mouth full of braces, which made her look somewhat younger in the face. She wore tight blue jeans, and a very tight t-shirt. Her chest was small, but her t-shirt allowed him an excellent view of every bulge her breasts 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 didn't make her 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 kind of jumped when he said hello.
"Finding everything okay?" he asked.
The girl nodded yes.
"I'm James."
"Ashley."
"Enjoy your shopping Ashley. 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 told him all about herself.
"These girls love to talk," he thought to himself.
The whole time Ashley 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 yacking about, he finally pieced together enough to be happy with how well he knew her.
She was eighteen, and a cheerleader. She had no boyfriend, and from the way she talked, was a virgin. She liked movies, pizza, and TV.
"You're very nice and too cute. I would love to see you cheer sometime."
"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.
He was tired of jacking off, and wanted to see how she would react.
"Well Ashley, 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."
"That is okay. I feel the same way about men in uniforms." She whispered.
He grinned, "I'll think about it."
"Come see me, I'll do some special cheers for you. Before and after the game."
"Ok, I'll be there."
He had a silly smile on his face as he watched her walk over to her mother.
That night, James went to the football game, and managed to sit on the bottom row. Ashley was in her red and black uniform, and looked very cute. She looked sexier than she had at the mall in the day.
At one point, Ashley walked to the bleachers, and slipped 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. James began to breathe heavily; he could feel his penis getting hard.
"Wow!" he thought.
After the game was over, James waited in the bleachers till almost everyone was gone. After what seemed like forever Ashley came up to him.
"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.
"Meet me by the locker rooms in 15 minutes."
He went over there, and sure enough, she showed up as promised.
"Let's go inside."
James wondered what she was up to, 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.
Ashley 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.
"I feel uncomfortable being here, like this."
"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 didn't know how to answer, fearing he might ruin it by saying the wrong thing.
"Come on, tell me. Did you?"
"Yes, of course. You're cute and your lips are very kissable."
"Would you like to kiss me now?"
James couldn't resist.
"I'm ready to become a woman tonight. I want you to be my first."
"Your first?"
"Yes, I've never gone all the way before."
"Why me?"
"Well, I like men in uniform and you turned me on today. Plus, after what happened with my friend Amy, I prefer my first time to be with somebody who has some experience."
"I see... "
"Also, you're not in our school and I'm less likely to get a reputation this way. Young boys blab a little too much and brag about their conquests."
"I see you have thought this through."
"I guess I did."
Without anymore words, James 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 little knee, and began to massage her inner thigh. She didn't stop him, and just continued to kiss him. He moved his hand higher up her thigh, and under her skirt.
Her legs closed a little stopping his hand's progress. He stopped pushing and soon enough her muscular thighs relaxed again allowing further advance.
She began to kiss him again, and soon his hand reached her moist crotch. 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 clit.
"Ohh... "
He slipped his hand further down and his finger found her wet lips. He wet two fingers and moved them back to her clit. He spread her juices around the little hard nub and started to stroke it very lightly.
Her thighs spread out all the way and her head moved away breaking this kissing. Ashley's mouth opened quite a bit and started taking quick shallow breaths.
Before he could stick a finger into her, she pulled his hand away and stood up in front of him.
"Let me take these off!"
She pulled her panties down to her knees and let them drop the rest of the way. His eyes followed their progress all the way to her ankles. The panties were white, and had a large wet spot in their crotch.
She stepped out of them, and she raised her skirt up. Her pubic hair was light and brown, and very sexy. She was directly in front of him, so he reached behind to cup an ass cheek in each hand pulling her closer and leaning forward to kiss her pussy.
Before his face could reach her, Ashley arched her back sticking out her pussy to give him easier access. Her clit was prominent at the top of her slit crowning two engorged lips. This girl was fully aroused and ready.
When his tongue made contact with her nub, her skin became covered in goose bumps. He didn't lick her clit aggressively, instead he did it quite gently as he figured that she must be quite sensitive. However, after only swipe or two of his tongue, her hands dropped her skirt and grabbed onto the back of his head mashing his nose into her pubic hair and giving her stronger contact with his heavenly tongue.
He didn't disappoint her. He gave her the tongue lashing that she was asking for and soon enough, she shook in a mind numbing orgasm.
Her knees buckled under her and she couldn't stay standing, so he guided her back to the bench and sat her down.
Her eyes were closed and a look of bliss decorated her beautiful face. He reached under her shirt, and unlatched her bra. As he ran his hands to the front, the bra pulled away from her breast.
Her tits stood proudly in place as he cupped his hands around them. As though they had a mind of their own, James's fingers squeezed Ashley's hard nipples few times, eliciting pleasure moans from her lips.
Soon she opened her eyes and looked deep into his.
"Want to see me naked?" she asked softly.
"Oh god yes!" was all he could answer.
She unzipped the skirt and pulled it down while raising her hips off the bench. Her hands reached across her waist and took off her shirt also.
His dick was pounding as this vision stood bare before him. "You are so 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 straight up as she held on to it.
"Wow!" she said, then hesitantly licked his glans.
"I've never gone this far before. I've given hand jobs, but... "
"Don't worry, there is nothing to it. Just be careful with your braces. Cover your teeth and the braces with your lips and use your tongue a lot and I'm sure you'll do just fine. Use your instinct."
She lowered her mouth onto his penis, and the warmth was overwhelming. She was new to this, but oh was she enthusiastic. She sucked his head for a little, then put more of his shaft into her mouth. She took it in deep as she could without gagging. Soon she started bobbing her head up and down. But her inexperience showed as she was sucking while doing it.
"Keep sucking while going up and down, it feels much better that way."
She was quite a good learner. She started going up and down while keeping a strong suction on him. She was doing it so well that he was at risk of blowing his load too quickly.
Finally, he told her she would have to stop otherwise he would cum.
Ashley stood back up, and he pulled her over his lap, straddling and facing him.
"Are you ready?"
"I think so." Her voice trembling a little.
"Alright, take it slow and easy. There is no rush here."
He held his cock steady as she slowly lowered herself down onto it. It was tough at first. She jumped at the first touch of his head as it hit her clit. She moved forward and her lips smeared her juices onto the head lubricating it.
She relaxed her legs a little putting some hesitating pressure on her lips. They spread slowly, but it was a little too scary for her. She pushed herself back up breaking their contact.
"It's ok. Just relax a little and try again." He reassured her.
Again, she lowered herself slowly and again her pussy made delicious contact with his cock. She put more pressure this time but again started pulling up.
"It hurts. It hurts." she complained.
However, he knew that she needed some firm help, so before she could break contact again, he let go of his cock and grabbed her hips and pulled her down quickly.
Ashley let out a small quite scream, but he held her on tight and stopped pushing after about two inches of his cock disappeared in her impossibly tight love glove.
After a minute or two of being completely motionless, catching her breath and getting used to this new feeling, her legs began to relax and she slid down taking more of his meat inside her. Soon, she was taking most of his dick in her and he could feel her cervix rubbing against his cock.
She could feel her pussy burning as it stretched more than it ever did before. It wasn't such a bad feeling though. Actually, few minutes later the pain had reduced to a dull ache and a good sensation was starting to replace it.
At his prompting, by pushing her away a little and pulling her back, Ashely began to ride his cock back and forth. She fucked him like no other had before. Her previously virgin pussy was clinching his dick with its tightness. Her motion didn't have the smoothness of experience, but had the definite enthusiasm of youth. He watched her ride him, and kissed her again.
After a few minutes of fucking this way, he decided he wanted to get on top of her.
So he stopped her and moved her off his cock and onto the bench, laid her back and spread her legs.
"I know you will like this." He buried his face in her pussy, and began to eat her out. Her juices had a light tinge of red as she bled just a little bit when her hymen broke. But, it wasn't too much. Definitely not enough to put him off.
She moaned and held on to his hair as he licked her up and down. She was so wet; his face was covered with pussy juice.
After a while, he raised up, and told her, "Time to fuck again."
He climbed on top of her, and worked his dick back into her. She moaned and scratched his back as he thrust into her over and over.
He talked to her as he fucked her, "Oh baby, I'm glad I met you today. Your pussy is so tight. I love tight pussy around me! I am going to cum into you!"
She just continued to pant as he worked up to his orgasm.
Finally, he could hold it no more.
"I'm gonna cum... "
"Oh yes, do it. Give me my first cum... "
His cock shot the first load deep inside her. He had it buried in deep as it sprayed his cum into her tight body.
"I can feel it! I can feel your cum spraying into me! Don't Stop! I'm cumming again."
After he was empty, he pulled out his cock, and sat on the bench next to her. He talked to her for a little bit, and both of them decided that what just happened would be their little secret. As he pulled his pants back on, Ashley handed him her underwear.
"Keep these as a reminder of tonight."
He just smiled and took them from her.
When he dropped her off at home, she jumped out of the car.
"Better go quick!" she said.
As he drove off, he looked back at her in the rear view mirror one more time shaking his head in amazement at the day's events. He never expected to end up with her that way. He surely didn't expect to take a hot girl's virginity just like that.