Chelsea's 18th Birthday Ch. 01

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Shy Chelsea loses her virginity to popular guy.
10.2k words
4.49
141.9k
54

Part 1 of the 4 part series

Updated 10/20/2022
Created 10/20/2008
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This is a re-submission. A few things have been adjusted as to better communicate the story. A very special thanks to my editor, Alwaysupforu2004. He has helped me to see my story through my audiences' eyes.

This is my first story to post on Literotica. I enjoy probing the minds of my characters to add a second dimension to my writing. In this story, the italicized sentences or phrases are thoughts. Also, this story is written in two perspectives. It starts off being in the perspective of the young woman. The story will continue in the young man's perspective about three quarters of the way through. I thought this added a whole new way of getting to know the story's characters without being omniscient.

Enjoy! Please, don't forget to vote at the end and leave any comments that you have! Thanks so much!!

**********Chelsea's POV*************

Man he's gorgeous, she thought to herself as she peered across the mail room hoping she didn't get caught. They graduated from the same high school last spring, in the same class of 580-something. But she knew he had no idea. But she knew. Everyone knew Brent Hawkins. Even if you didn't go to any of the Baseball, football or basketball games.Jock, whore, asshole, she thought resentfully. She assumed he was an asshole, anyway. She knew he was a jock and was pretty sure he was a whore. Every weekend she could hear him watching porno flicks next door. Yeah, she lived right next door to this gorgeous man slut for two months and had he even noticed? Or said, "Welcome?" Or brought over a pie? Of course not. She almost laughed aloud at the thought of Brent Hawkins leading the welcoming party in the Westwood Apartment building.

Oh shit. He was coming her way. He half-smiled as he walked past her carrying his mail. She looked down at her own mail. Just some ads and a birthday card from her grandmother that was two days early. As usual.

"Happy Birthday," she heard.Is someone talking to me?

"What?" Chelsea was stunned.

"It's your birthday, isn't it?" She just stared back. "Looks like a birthday card," he said looking down at the big purple envelope.

"Oh, no. It's actually Saturday. And thanks." She blushed, hardly every making eye contact.

"Chelsea, right?"

"Yeah, how did you know?"

"You went to Broadmore, didn't you?"

"Yeah!"He remembers me!

"Yeah, you were the chick that got caught T. P.ing the cheerleader's locker room during the Homecoming pep rally."

Oh. Of course he would have to know her because of that. "Yeah, and I also live right next door to you," she said trying to change the subject.

"You do?" he exclaimed, obviously genuinely surprised. Talk about a major blow to your self-esteem.

"Um, yeah, 8B," she said.What a pig. She'd been here for two months and he didn't even notice?!

"I didn't notice," he said with a chuckle. She really shouldn't be surprised. "Anyway, welcome to the building. See ya around." He started jogging up the stairs before turning back and adding, "And if I don't see ya Saturday, happy birthday."

"Oh, thanks," she called after him. As soon as he was out of sight, she jumped up and down in place with excitement. "Oh, my gosh," she exclaimed quietly to herself.He is so hot! He is so sexy! His is so nice; somehow. Suddenly she calmed herself down when she realized that just because he said 'happy birthday' to her didn't mean that she had any more of a chance with him than she did before he had given her the time of day. What did she care anyway? He wasn't her type! Sure, he is the hottest guy she'd ever seen but he's a jock and she hated sports. And he was a whore. Probably. Thoughts of him banging some slut cheerleader flooded her imagination. She could see the sweat on his beautiful brow as he worked with such commitment to his task. His craft, most likely. Imagining him in a sexual tryst made her tremble. Why did she feel this way?

Chelsea made her way back to her apartment, making sure to give Brent plenty of time to get in his own apartment. She threw the mail on her bedside table and flopped down on her soft red comforter covered bed. She couldn't get the thought of him grinding and slamming into some faceless girl out of her mind. It was making her hot.He probably know everything about pleasing a girl. Before she knew it she was rubbing her chest through her fitted tee. She wished it was Saturday so she could hear Brent's porno. Then, the thought of him masturbating crossed her mind and she closed her eyes and smiled.Does he do it naked? Does he do it fast or slow? Does he use a toy? Gosh, do they even make toys for guys?

She slid her hand up her shirt and under her bra. Chelsea loved tweaking and teasing her nipples which were now rock hard. That washer masturbation. She didn't understand enough about her own sex organ but she did know that she loved her C cups.

The clock read 11:20 pm. She had to work at the seed store at 8 on Fridays and decided she'd better get some rest. As the darkness overcame her, thoughts of Brent flickered through her mind.

*******************************************************************************

"Chelsea, stop squirming." His voice was harsher than she thought it should be considering the circumstances.

"But it hurts!" she exclaimed as she tried to push him away.

Chelsea lay on her back, buck-naked, pleading with Brent who was pushing his hardness into her as his body lay on top of hers. He was too strong and held her down.

"Don't you want me to teach you anything?" he said sharply. "I thought you were ready to loose your virginity, Chelsea."

"I am. I love you, Brent."

"Love?" Brent laughed as he drew away from her. Now he was fully dressed and she heard voices. Female. Laughter. She looked around. She was laying on her back on a bench in the vandalized cheerleader locker room. The entire squad pointed and laughed making jokes.

"But she loves you, Brent!" one of them cracked.

''She's so wet she is dripping on the floor. Gross!"

*****************************

What a pleasant sound, her alarm. Seven o'clock had never been so welcomed into her bedroom. Why had she dreamt those terrible things? She had no desire for Brent Hawkins to be the one to deflower her. Well, maybe not 'no desire.' It didn't matter. She needed to get him off her mind fast. Why had he become such a presence in her mind now? She didn't care at all in high school. She had never given him a second thought before they talked. Ah, that was it, she knew. They had talked. Now she actually has made contact. And enjoyed it. Enjoyed him. Maybe he wasn't so bad after all. Yeah, she could see herself with him.

What? Come on! Stop it, Chelsea. Get a grip, Brent would never be interested. You're not into sports, makeup, orsleeping around.

Chelsea never thought herself to be beautiful. She was cute for sure, even without the war paint as she called it. Healthy build and average height. She liked having meat on her bones. The sight of ribs on a girl made her nauseous. And knowing that that fits into modern society's definition of beauty only pissed her off. Yeah, that's why she vandalized the locker room.

Locking the door behind her, she turned, astonished and embarrassed at the sight of Brent standing feet from her. His cute curly blond hair wet. Sweat pouring from his brow and cascading down either side of his shirt. He stood there breathing heavily and heavenly. She couldn't help but pass her eyes over his firm body.

"Hey," he said as he panted with his hands clenching his hips.

"What are you doing?" She didn't know what else to say. She was still alarmed.

"Morning run. Feels great," he managed to get out between his heavy pants. "You should try it."

Her brow furrowed and her jaw dropped in disgust at the way he had insulted her.I'm right! He is an asshole!

"Whoa, girl. I mean, you should run sometime. It's good for your heart, helps you clear your mind," he stated trying to ease the tension.

How embarrassing. Surely she was blushing now.

"Oh, sorry. Of course that's what you meant. But I don't know. It's kind of boring to me," she said trying to regain some sort of composure in the conversation.

"Wouldn't be boring if I was there. Or is that what would make it so boring?" He chuckled.

"Oh, no! No, I didn't mean, I mean, I didn't know you were talking about..."

"I usually leave at around 7. Anytime you want to join me, you're welcome to.

Are you kidding me? "Alright, thanks. Sounds good."

Brent walked past her without saying another word and slipped the key into his door unlocking it.

"Oh, and if I don't see you tomorrow, happy birthday." He flung his shirt off in one swift motion revealing his gorgeously toned body. Not too muscular, but just how she liked it.

"Thanks," she managed to say before he closed to door behind him.

******************************

She wasn't sure why she set her alarm so early. Six am interrupted her slumber as annoyingly as she had imagined that it would. Ah, but remembering why she was up so early on a Saturday morning woke her from her haze. Brent. Run. Body. Such a sexy body. She had to see it again. She showered and shaved her legs and everything. She donned her gym clothes from her senior gym class. Not too nerdy but it was all she had. Chelsea looked at herself in the mirror. Straight, jet black hair pulled back in a pony tail. Amazing green eyes that she got from her mother. She wasn't entirely happy with her round face. She thought it made her look younger than she was.

She was ready. She decided to wait until 6:55 to go into the hallway. No Brent. She sat and waited at least ten minutes.

It wouldn't hurt to knock, right? Either he left early or he's almost ready. Either way, no harm done.

Making sure to knock hard enough the first time, she hammered at the door. No answer.What am I doing? Chelsea felt stupid. She probably looked desperate. "I'm out,'' she said under her breath.

Just then the door to 8A opened slowly. She froze.

"Who is it?" she heard a sleepy grumble.

"It's Chelsea. It's 7:10."

The door opened for her to find a tall thin guy standing dazed in pajama pants and a wife-beater. "Who?"

Startled, she re-focused and said, "I'm here to see Brent."

"Oh," he grumbled. "He's in his room. Come on in." Slightly relieved and bewildered, she followed him in. He flew to the couch and got ready to re-enter his sleep.

Chelsea crept to the bedroom. The door was half way opened so she walked in. Why was he still asleep? Did she look at her watch wrong? No. Confused, she glanced around the room as if might find the answer to this riddle on plastered on the wall. Books, computer, more books, a desk. Jock, whore (supposedly) andnerd?

Her concentration was broken when she heard him stir. The only thing she could think to do was flee.

"Chelsea?!" a groggy voice halted her escape. "What are you doing here?"

She wasn't sure if she remembered how to speak. Even if she did, what would she say?

"What time is it?" he said, looking around.

"7:10," she stammered.

"And what's going on?"

"You invited me to run." Chelsea spoke before she could allow the panic to hinder her again.

Brent closed his eyes and threw his head back into his pillow. "Come here," he said. She hesitated but complied. "Today is Saturday?" She nodded and he sat up allowing the thin blanket and sheet to fall to his waist. As hard as she tried not to, she found herself admiring his body again. A quick glance at his lap proved what she'd heard about guys when they first woke up in the morning. There was a significant raise under the covers and she knew she'd just die if he caught her looking.

"I stay up late on Saturdays, so Saturday and Sunday I sleep in late. I should have told you. I'm sorry," he said in a half-trance state. "Shit."

This is officially the worst day of my life, she thought.I am so stupid!

"Damn, you're all dressed and everything."

"I'm really sorry," she mumbled as she turned toward the door, her entire body engulfed in humility.

"Hang on, wait." His hand clamped around her wrist and he pulled her around as gently as he could. "It's my fault. I'll make it up to you. I feel really bad."

She was about to burst into tears and he could probably tell. "Listen, Chelsea, do you have anything going on tonight?"

She shook her head no.

"Why don't I take you to dinner?"

"You don't have to."

"I want to. Call it an apology/birthday dinner."

She simply stood there, out of body, trying to process the entire situation.

"But if you don't want to, that's fine, too," he said, confused as to why she was acting so strange.

With that Chelsea snapped back to reality and answered, "Oh, no. That's fine. I'd love to go to dinner with you."

No! Don't say it like that, you twit!

"I didn't mean, like, I'd love to go to dinner with you. I meant, like, that is a good way to ... whatever."Stop before you make it worse! "Okay, I'm gone," she said quickly, longing for the exit.I am such a fucking idiot, she cursed herself looking down at her dirty tennis shoes and walking out the door of Brent's room.

"So, tonight then?"

She stopped short, surprised that he was serious. She's practically drooling on his floor and acting like a middle school girl and he acts like he doesn't even notice. "Seriously?" she asked.

"It's whatever, dude. If you got a boyfriend that'll get all pissed off, I get it, ya know. It's whatever," he said still sitting up in his bed.

"No, it's not that. I was just kinda surprised is all."

"And your boyfriend won't care?"

"No. Well, I don't have one."

"Uh huh. Well, I know where you live. I'll come over later. I'm going back to sleep." Brent talked to her as if they really know each other. And they really don't know each other very well at all. How can he be so confident when she's so nervous?

"Okay, later," she said and left without another word. As soon as she closed the door to her bedroom she screamed. She was going to dinner with Brent Hawkins? Her initial reaction was of disbelief and excitement. Eventually, her negative side got its say.So what? He's not your type and you're definitely not his. Just enjoy the free meal and get over it.

Chelsea ripped her clothes off and jumped into bed naked. She wanted to touch herself while she thought about her "date" with Brent later. She held her breast in her hands, rubbing the sensitive underside. This felt so good to her. Chelsea imagined Brent touching her here. Ooh... and kissing here there, suckling her tender nipples. Her hands squeezed her breasts. Out of nowhere she felt a pleasant tingle between her legs. Perhaps this would be a good time to explore this sensation. She slid her hand down her soft tummy to her bush. She spread her legs wide and slid a finger between her untrimmed lips. It felt okay. She wasn't sure what the big deal was with masturbation. However, she wasn't ready to give up on it. She circled her fingers around some more finding her hole. It was moist here. Chelsea wet her first two fingers with her juices and spread it over her entire vulva. And again. And again until her whole pussy was covered in her lubricant. This is starting to feel good. What if Brent would touch her like this? The thought sent tiny shock waves through her body starting at her clit. With a probing finger, she found the source of this amazing sensation. She liked this. She rubbed this area for a little while. It was feeling better and better with every stroke, she discovered. Chelsea found herself speeding up, unable to stop, not wanting to move from this one little spot. Squirming and moaning now, she rubbed harder and faster. Am I going to have an orgasm like this?

Chelsea pictured Brent making her feel this way. With his hands. Or maybe with his tongue? Imagining the strong and sexy Brent Hawkins with his head between her legs sent her over the edge into her first orgasm. Her entire body stiffened as she caught her breath. She rode through it bucking her hips and clenching her hand between her legs. She rubbed it a little bit more but found it way too sensitive now. Wow, she was sweating. It was time for another shower but this time she was going to take care of all this hair surrounding her newly discovered play thing.

So, that's what masturbation is all about! What took me so long to try this? She giggled as she headed to her bathroom.

She stayed home all day obsessing about the evening ahead of her. Where would they go? What should she wear? When was he coming over? What do they talk about?Don't make a fool of yourself!

She couldn't leave in case he came by. Knots began to form in her stomach. She obsessed until she made herself sick. Then she decided she should eat a little bit since she had forgotten to all day.

*****************************

"Dude, you don't have anybody to screw tonight, man!"

What the hell? The voice came from the hall just beyond her front door. She ran over and peered through the peep hole. There stood Brent and his friend, the tall lanky guy, talking in the hall.

"You've gotten laid every Saturday night since like, February or some shit."

Oh my god, that wasn't a porno, it was him!

"Dude, shut up. I had to break up with her. I'm tired of just seeing her on the weekend. It's bull shit. Not worth it."

"No pussy tonight, bro," Clay said.

"You don't know that, dude."

"You goin' to the club after your little fling with that weird girl?"

"I might and so what if she's weird? I think she's cute."

"Bro, seriously?"

"Yeah, seriously. She is cute. Anyway, don't worry about my dick. When the hell's the last time you got laid?"

"I'm waiting for the pretty ones, man," he teased, laughing proudly at his low blow.

"Dude, man, she'd fuckin' cute as hell. And maybe she has a brain. And I didn't ever say I'd fuck her anyway," Brent exclaimed.

"Sheis fatter than Danica, man," the tall guy said.

"Clay, the fucking skeleton in Ms. Hendley's bio class was fatter than Danica," Brent scoffed.

So, I'm cute and fat? I'm cute?! I'm fat?! She wasn't sure if she should be happy or devastated hearing this.

"Aren't you going to go talk to her?"

"Danica?"

"No, the weirdo."

"Yeah, in a few minutes."

"Where you gonna take her?"

"Hell, I hadn't really thought about it since I woke up; the second time."

"Dude, when she opened the door, I almost told her she had the wrong apartment," he said laughing.

"Clay, man."

"She wasn't even wearing make-up."

"And? Maybe she's confident enough that she doesn't think she has to."

"She should look into it, that's all I'm saying."

"Girls don't have to look like a $5 hooker to be pretty, dude."

"I like hookers," Clay joked.

"Yeah, just like your dad liked your mom," Brent added cleverly.

"You suck!" Clay exclaimed.

"Just nipples and clits, dude," Brent retorted making Chelsea smile.

"Whatever. I think you're phone's ringing."

*******************************

Twenty minutes later a knock came on her door. It was Brent. She opened the door enough to stick her head out. (He could see her "cute" face but not her "fat" body.)

"Hi."

"Hey, Chelsea, there's kinda been a change of plans for tonight. I was wanting to take you to get some Chinese or but my dad called and wanted me to meet him for dinner tonight at 7:30 at Juliard's."

Figures. I obsessed and made myself sick for nothing, she thought. Juliard's is a really nice place, no wonder he chose to go with his dad.

"So, you have a dress you can wear, right?"

"What's that?" she asked with two raised eyebrows.

"It's a really nice joint. The ladies usually wear a dress," he explained. "I can get him to cancel if you don't, and we'll just go somewhere a bit more chill."