tagFirst TimeAn Unlikely Valentine

An Unlikely Valentine


Thanks to my editor Cheer_Smartie526 for the help with this. I hope you enjoy the story.


Carrie gently knocked on the door to Carl's room, "It's me...may I come in?"

His voice was muffled by the closed door, "Sure."

"I heard about the prank. That's so high school..." she said.

"Well, I am in high school, so I guess that's the way I should act," Carl answered.

Carrie walked across the room and sat on the floor next to Carl, "What are you going to do?" The corners of Carl's mouth turned up just a bit. Normally the job of cheering him up fell to Daniel, Carrie's brother, but Daniel was away on a school trip. It was harder to talk to Carrie, although she was a lot more pleasing to look at.

"Nothing," he sighed.

"No plans for revenge?" Carrie asked. Carl was a nerd and an easy target for others. He was also her friend.

He sighed again, "You know what they say about revenge."

"It is a dish best served cold?" Carrie guessed.

Carl chuckled at Carrie's attempt to be a geek, "Only if you are Klingon. I was foolish to think I had a secret admirer. Looking back it was pretty obvious the whole thing was a setup. Nobody is going to be my valentine. "

He looked at Carrie. Her brother had been his best and only friend at his old school. She had tolerated him. There was no way she had any idea how he felt. They were quite different. Carrie was two years older and a beautiful young woman. She had always been popular and made friends easily. With her long fiery red hair and near perfect body, she had no shortage of admirers, secret or otherwise. In contrast, Carl had no one at the school he regarded as more than an acquaintance. Even the unpopular kids treated him poorly; hoping to elevate themselves from the bottom rung of the school's social ladder. The midyear transfer during his senior year had only made things worse.

In response, he had focused on his one useful gift, his intellect. He was taking several university courses by correspondence. Carl considered his actual classes nothing more than study hall. He begged his parents to let him finish high school early, but they had insisted he complete it for the social experience. He was very mindful to remain positive. There were too many stories about the distant but brilliant loner suddenly turning violent. Carl considered those incidents to be a tragic waste, and he had no intention of ending up like that. Someday he would have the resources to buy and sell the people that taunted him today. All he needed to do was sit and wait.

"So no wrath of Carl?" she asked. "No, . I was thinking the best revenge is living well. I'm planning on getting some good Karma out of this."

"That's the spirit," Carrie said cheerfully.

The worried about Carl. It had taken her years to finally get him to talk to her. He was her dorky kid brother's nerdy friend. Carl had practically lived at their house. He appeared cold and logical. Sometimes she thought he was an alien sent to spy on humanity. Over time Carrie discovered he was well intentioned and extremely smart. Without Carl's patient tutoring Carrie figured that she and almost every one of her fellow cheerleaders would have failed at least one subject. Carrie was amazed that as a sophomore Carl had mastered every bit of her senior homework. His condescending demeanor insured that all he received from the others was a polite "Thank you", but she was always nice to him.

Carrie gazed at him. He was tall, lanky and surprisingly flexible. He was sitting on the floor with his legs folded in what looked like yoga pose. Carl wasn't so much anti-social as he was an introvert. He simply did not see any value in interacting with others unless there was a direct reward. He would ask questions to further his knowledge, but he rarely just wanted to make small talk.

There was one other thing that Carrie knew about Carl that no one else did. He had a huge cock. It was something she had discovered by accident. She walked in to the living room one morning to discover Carl and her brother passed out after playing computer games all night. Carl was sleeping in his boxer shorts. His penis was hanging through the fly of his shorts.

She did not realize it until she started having sex and noticed that the guys she was with were noticeably smaller. Carl's flaccid penis was bigger than any erection she has seen in real life. Her brother's friend was hung like a porn star. And he wasn't just a shower; he was a grower as well. She had walked in on Carl and her brother when they were watching internet porn once and the bulge in Carl's pants was quite impressive. She thought she saw the tip of his erection protruding above the waist of his jeans. For several of her girl friends at college, Carl's size alone would more than make up for his lack of looks and personality. They were all about bagging the big ones. Just thinking about it made her wet, which in turn made her feel guilty.

"Let me help you," Carrie offered.


"I will go to the dance with you. Nobody at your school knows me. If anyone asks, tell them you were getting messages from two admirers. You knew one was a prank, but the other was real," she explained.

"That's brilliant," Carl answered.

"So," Carrie said innocently, "will you be my valentine?" Carl's mind began to develop Carrie's idea. She was certainly attractive enough to make a lot of people jealous. As a bonus, she had a sharp tongue and would have no problem fending off suitors with snarky remarks. Carl had harbored a forbidden crush on his friend's sister since he had hit puberty. He had never acted on his desires, mostly because he was afraid of how everyone (especially Daniel) would react. Making a pass at his best friend's sister seemed to go against social norms or at least his limited understanding of social norms. This dance was the closest he thought he would ever be to getting physical with Carrie.

Even though she had attended a different school, the high school dance was exactly the way Carrie remembered it. Being with Carl gave her a slightly different perspective. She was not holding court at the popular table, listening to the other pretty students' gossip about anyone not in attendance. Instead she was with the 'less than desirables'. Every time she and Carl were on the dance floor, someone tried to cut in. She disposed of each guy that had the gall to approach her. One of them almost looked like he was going to cry. Carrie enjoyed using her waspish tongue to dish out some revenge for Carl. His smile grew after each encounter.

The more she talked to Carl, the more Carrie enjoyed his company. She had always figured that Carl and her brother spent all their time making snarky remarks about the popular crowd, playing video games and downloading porn. She was surprised to learn the two young men were active in charities and were actually interested in women. They just felt like there was no way out of the geek caste. Carrie realized that Carl could carry on a conversation on a topic other than science fiction or fantasy games.

She had to admit that Carl actually cleaned up quite nicely. His suit was well fitted. The one thing about him that did not fit the nerd stereotype was his complete lack of acne. His nutmeg brown hair looked presentable once she convinced him to wash and comb it. He still had a bit of the Ichabod Crane look, but she was willing to look past that. Most important of all, he really seemed to be enjoying the dance.

Carl felt a presence behind him. A voice boomed over the DJ's music, "Mind if I dance with your date"?

"He might not mind, but his date does," Carrie replied, giving the interloper her best go to hell look.

"You might not know it, but I am kind of a big deal round here," the intruder continued, ignoring Carrie's icy glare.

"You don't look too big to me," she replied, staring directly at his crotch, "I think I'll dance with the one who brought me."

Carrie grabbed Carl by the wrist and dragged him out to the dance floor. "Yeah" by Usher was just ending. Carrie remembered the same song being played at her 8th grade dance seven years ago. The next song was a slow dance. Carried pulled Carl close against her body.

"Who was that jack hole?" she asked.

"Captain of the football team," Carl replied.

"Want me to make him cry?"

"No, I can take care of him," Carl answered.

Much to her surprise Carl could actually dance. Carrie knew he had an amazing ability to learn new things, but she thought it was limited to academic pursuits. Apparently he was able to learn physical skills just as quickly. She suddenly recalled seeing a book on tantric sex in his room. An extremely naughty thought popped into her head. She tried to push it out but could not. Carrie felt her face turn red as her nipples started to get hard and pressed against her brother's best friend. The song ended and much to her relief Carl led her back to their table.

"Dare I ask what you are going to do to my new least favorite person?" Carrie asked, trying to put something other than carnal thoughts of Carl into her brain.

Carl was tapping on his Smartphone, "I put a backdoor into the school's textbook inventory program. Mr. Marston is about to lose three very expensive textbooks. They will eventually be found, but not before his parents get some very nasty letters."

"You can do that on your phone?" Carrie asked. She was not as adept with computers as Carl was.

"The school does not follow any best practices with their network security. I should tell them, but I guess I'm a bad person. I can do a lot from this phone. For example, I can tell the HVAC to let the temperature rise up a bit," he said calmly.

"Can you get into other parts of the school?' Carrie asked. She was on the verge of giving into her desires. She found Carl's cyber bad boy alluring.

"Yea, I made a copy of a teacher's access card. It will open any door in the school except the police officer's office. I think they actually audit that log, so I did not want to raise any flags. I can also just tell the computer to unlock the doors. That's actually better, it does not leave as much of an audit trail."

"Then turn up the heat in here and let's blow this Popsicle stand," Carrie said excitedly. She wondered if she would regret setting this plan in motion.

Carl was enjoying all the attention he and Carrie were getting. He had been anonymous ever since he arrived at this school at the semester break. With Carrie at his side almost everyone at the dance had noticed him. He wondered if they would notice him on Monday, or if it would just be like every other school day. But now, he needed to disappear. With a few taps on his phone, he turned the lights down around the door they would exit through and made it a bit brighter everywhere else to spoil everyone's night vision.

"Can you get us into the principal's office?" Carrie asked as they left the dance.

"Of course," Carl replied. As they approached the service door in the back of the gym, it unlocked. No one at the dance noticed as they slipped through the door and into a service corridor that led to the main school building. Two minutes later the door relocked, just like Carl had programmed it to.

The thrill of having sex in public places was a practice Carrie had picked up her sophomore year. One of her many boyfriends had a work study job as a custodian, so he had keys to a lot of the buildings. He liked having sex on teacher's desks. He said eight o'clock classes were a lot more bearable when you were looking at a desk you had been fucking on a few hours earlier.

The moment the door to the principal's office closed behind them, Carrie grabbed Carl's cock. Much to her relief, she felt his throbbing erection. He had to be thinking the same thing she was.

"You know what I want?" Carrie asked.

"I hope so," Carl replied, his voice cracking.

"Have you ever kissed a girl before?" She asked.

"No," he answered honestly.

"I'll show you how it's done then," Carrie whispered, and then she pressed her mouth to his.

First she sucked on his upper lip, then his lower lip. Finally, she slipped her tongue into his mouth. It did not feel wrong; instead it was incredibly arousing. It did not matter that Carl was her brother's friend, or that he was younger and less experienced...she was going to do what no one else had done to him. Carrie intended to make this a night that Carl would dream about for years to come.

He could not believe what was happening. Carrie was on her knees in front of him pulling down the zipper of his pants. He struggled to recall all the information he had assimilated on sex. What he should do to her, how he could make it last longer, what could go wrong. His thoughts were jumbled and his heart was pounding. Excitement was a new experience for him. He found it both disturbing and enjoyable.

Extracting Carl's erection though the fly of his dress pants proved to be a challenge. Finally the engorged head of his penis emerged. She wrapped both her hands around the thick hard shaft and guided the purplish head to her mouth. Even if she deep-throated him she would not be able to fit his entire penis in her mouth. Carrie wondered if the girls at this school knew what they were missing out on by snubbing Carl.

The moment his cock slipped into Carrie's mouth, Carl felt his orgasm begin to build. Her soft lips and wet mouth felt quite different from masturbating. The novelty of the experience raised the level of his arousal dramatically. Part of his mind was fascinated by the experience, recording every nuance for later study. However, a more primitive part of his mind was simply enjoying the experience for what it was. Bit by bit, the primitive brain won out. Soon all Carl could think of was the heavy load in his aching balls. All his reading on tantric sex proved to be ineffective against Carrie's skilled mouth and hands...

While she inhaled his cock Carrie struggled with Carl's belt and pants. Eventually she unfastened his dress pants and let them fall to the floor. Carrie took her mouth off his throbbing erection just long enough to remove his boxer shorts, and then plunged it back down her throat. She pumped one hand up and down the entire length of his enormous cock and stroked his balls with the other. Carrie could feel him struggling to hold back his orgasm.

"Uh, uh, uh," Carl stuttered, "I think I'm going to come." Carl had said those words to hundreds of imaginary lovers, but he had never meant it more than he did now. His words only seemed to encourage her. Her tongue pressed firmly against the most sensitive spot on his penis. Her hands caressed him in all the right places. He looked down at Carrie, fully aware of the consequences. Carl knew that the sight of her lips wrapped around the shaft of his cock would push him over the edge.

Carrie wasn't the kind of girl that swallowed. Most of the time she finished a blowjob by pumping the guy's cock with her hands and moaning for him to come on her tits. Guys seemed to like that. She was not sure if it was the dirty talk or the chance to act like a porn star. But for some reason she wanted Carl to come in her mouth. There was a practical reason, if his cum ran down her throat now it would not be running down her leg after they fucked. She got her wish. A thick stream of warm, salty liquid sprayed into her mouth and down her throat. There seemed to be a lot of it, but finally the flow stopped and his cock began to soften. She let it slip from her mouth.

"Don't worry, it will get hard again soon," she said reassuringly. Carrie certainly hoped so; she wanted to ride his monster cock to her own orgasm.

"Seventeen minutes," Carl replied, "that is my average refractory period."

Carried guessed he would beat his average once they were both naked. She stood and turned her back to Carl, offering the zipper of her dress to him. Her heart was pounding. She felt his fingertips as he gently grasped the zipper and began to pull it down. Carrie's chin rested against her chest so her hair did not get caught in the zipper. It afforded a view of her erect nipples straining to pierce the thin material covering them. She was horny, nervous, and excited.

The zipper reached the end of its track and Carl carefully peeled the dress off of Carrie's gorgeous body. He folded the dress neatly over the back of a chair, and then unfastened her bra. Carl had spent a fair amount of time learning how the fasteners on bras worked so he would be prepared for just such an occasion. All that remained was her thong. He simply slipped it over her shapely ass and down her legs. He set both of her undergarments on the chair with her dress.

Carrie turned to face Carl. Being naked in front of him made her feel free. Ever since she had seen his cock years ago she had developed a bit of an infatuation with the idea of having him inside her. She began to unbutton his shirt and soon they were both naked.

Carl looked down at his cock. It had never gone completely soft and seemed to be on the rebound. It was not quite ready for action, but would be soon.

"Seventeen minutes eh," Carrie said. She had no doubt that Carl had arrived at that number after extensive scientific study, but she doubted his research included a live naked woman.

"Average, I think tonight will be on the faster side," Carl responded.

"Well, while we are waiting..." Carrie put her hands on Carl's head and pulled him down until his lips met hers. She snaked her tongue into his mouth. He offered no resistance. She felt his hands on her shoulders. They slid down her body and cupped her ass. She pushed his head down and he began to kiss her on the cheeks, ears, jaw and chin. When his lips touched her breast she drew a sharp breath. She felt warm all over as her body begin to exhibit the first sign of her pending climax.

When she kissed him, Carl tasted the unfamiliar salty flavor of his cum. He was glad she had swallowed every bit he had deposited in her mouth. By comparison, her skin tasted almost sweet. There was a bit of a chemical flavor from her makeup and perfume, but mostly it tasted the way he had imagined. By the time his lips reached her breast his erection had returned to full strength. Even though he was anxious to feel her cunt wrapped around his dick, Carl continued to lick and kiss Carrie's breast. He wanted the full experience, not just wham, bam, thank you ma'am. Her breasts were perky, somewhere between a B cup and C cup. She had areolas that protruded slightly. Compared to the porn he watched, her nipples were on the small side, but their diminutive size did not take away from the pleasure he felt from licking them.

His languid pace was driving her insane. Carrie did not know if Carl was trying to frustrate her or just not sure what he was doing. His erection was clearly visible, why wasn't he pounding it into her dripping wet pussy yet? She had seen her brother's porn collection and guessed Carl's was similar; surely he had some idea of how to fuck. Although she was enjoying all the attention he was lavishing on her breasts, she wanted more. She wanted him inside her. She put her hands on his shoulders and pushed him back.

"Lie on your back, on the floor," she said insistently.

The moment he was supine she straddled him.

"Like this?" he asked.

"Exactly like that," she replied as she squatted over him and grabbed his cock.

Carrie made a mental note of its girth. She would brag about this conquest. Several of her friends would be quite jealous she was able to ride a monster dick like Carl's. She underestimated the length of his dick and the tip of his erection pressed against her labia sooner than she expected. She winced as it stretched her wide open. Carrie had intended to decrease her descent and take him in slowly. Instead, she had forced the first couple of inches in right away. She paused, allowing her body time to adjust to the intrusion. The look on Carl's face was priceless. He was staring between her legs, watching her pussy swallow his cock. She wondered how much of his book on Tantric sex he had completed. It was unlikely he would last more than a minute with it being his first time. Carried hoped his average refractory time did not increase after his second climax.

Report Story

bytk5555© 13 comments/ 106664 views/ 74 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: