Simple Simon

Literotic asexstories – Simple Simon by TheDarkestPlace,TheDarkestPlace
+++Good sex at the end, but not a “quick wank”+++

Simon’s life was anything but simple. He was like any other kid in high school, in love with the handful of beautiful, popular girls—girls that frankly had better options. He had buddies he hung with, but most of them wound up hanging out with the other guys on Saturday night. He remembered seeing the scene in “Say Anything” when the local losers sat in front of the Gas-and-Sip and gave bad relationship advice to Lloyd. He didn’t see himself as the romantic lead in the scene. He saw himself as the guy claiming they didn’t have girlfriends “by conscious choice.”

Walking home alone that night, he came to a genuine conscious choice. In a week he was going to graduate from high school. It was time, by the gods, to stop playing high school games. No more longing in vain for prom queens and cheerleaders, no more wondering what his buddies would think if he went after a girl with less obvious physical allure. He wasn’t lowering his standards. He was going to find a girl that made him laugh, that made him think, that made him feel something more than physical lust and a vague hope of an improved social status. It was going to be simple.

About a week after graduation, he started a summer job at a kiddie amusement park: the kind with low-flying rides that entertained three-year-olds but left anyone over the age of seven less than impressed. It was work, and he liked being outside a lot better than he had liked working in the kitchen at a restaurant. The park was staffed by a mix of high school and college kids. His status as a recent graduate, eighteen wonderful years old, provided him a chance to slide in with the older kids at the lunch table. And the joy of that was that these kids partied pretty hard and pretty often. He found himself allowed to tag along with a new crowd.

The first Saturday night found him at a house party packed with college kids on summer break. A month ago he would have found himself trying to make time with, and consequently being rejected by, slightly older versions of the girls that had rebuffed him in high school. But this was not the case anymore. Simon scanned the room for girls not standing in the big circle around the cluster of well-muscled jocks hammering back beer-bongs. He found a trio of girls sitting in a corner, drinking slowly and talking amongst themselves. He recognized one of them as Cassandra, the busty but chubby redhead who had trained him on his first two days of work. He had an “in.” He moseyed on over.

“Cassandra, hi! I just wanted to thank you for being patient with me the first couple days of work. You were really cool.”

“Sure, Simon. Not a problem.”

“Well, I’ll let you get back to your friends. Looks like you were having a good time.”

“Cass, who’s your friend?” a short girl with glasses asked.

“Becca, this is Simon—um it starts with a W…”

“Waters.”

“Well, Simon Waters, have a seat,” Glasses ordered, making one the third girl, one with several facial piercings, slide over.

“Look out, Simon,” Cassandra whispered as he shrugged and moved to sit down.

“Did she tell you to be careful?” Glasses said as he plopped down beside her. He didn’t want to give Cassandra up, so he looked as if he had no idea what she was talking about. “I know she did. She tells me I’m a ballbuster.”

“Really?” he said, mockingly covering his groin with his beer.

“So, Simple Simon, you’re a typical young man, why you over here by us instead of by that gaggle of peroxides over there?” She slid her glasses down her nose and looked over the top of them at the beer-bong crowd.

“I came to say thank you to Cassandra.”

“Could have done that at work.”

“Becca, the kid was just being nice,” the girl with nose, ear and brow piercings added, seemingly bored with the proceedings. “I’m sure he has other places he’d rather be. Let him go about his business.”

“Is that what you want, Simple Simon? To leave us and go about your business? Or are you checking us out?”

“Wow, Cassandra!” he said. “I’ve met two of your friends, and I like one less than half of them. Sorry to have interrupted.” He got up to go.

“Hey, come back when you can stay longer,” Glasses called out as he began to walk away. So much for the simple life and meeting a different group of girls.

He ran into Tony, one of the friendlier guys from work. He talked to him for all of about thirty seconds before Tony’s girlfriend grabbed him by the hand and led him off. Simon turned to look around the room and found himself face to face with Cassandra.

“Sorry about Becca and Carmen. They are kind of snots to younger guys.”

“Hey, I’m not upset with you, Cassandra. You’ve been nothing but wonderful to me. I hope I didn’t get you into hot water with your friends.”

“Fuck them. I don’t base who my new friends are on whether or not my old friends like them. I decided that a couple years ago.”

“H-mmm,” he grunted, half-smiling. Cassandra looked at him questioningly. “I just decided that a couple weeks ago.”

“And that’s why you chatted us up instead of the peroxides?”

“Would you be grievously offended if I said yes?”

“Considering I just said pretty much the same thing to you…I think that would be a little unfair. Well, just remember that my friends have been around the block a few more times than you, and they saw right through that. They get pretty jaded. Some guys at school act like we should be grateful just that they are talking to us instead of the party girls.”

“Well, I’m not trying to be condescending or anything. Let me be straightforward. Cassandra, I am hereby openly declaring that I find you interesting as a person and it would be pleasing to me if we had normal social interaction.”

“I also find that acceptable.”

“Sounds like Vulcan pillow talk.”

“Or a scene from “The Big Bang Theory!” Dropping Star Trek references this early in the conversation? You really are comfortable with me.”

“Well it seemed less geeky than the ‘Iliad’ shout-out I had kicking around in the back of my mind.”

“Cassandra giving you a warning and you ignoring it?”

“Pretty much. Glasses tore me a new one and Piercings just wanted me to go away. And I hadn’t even asked her if she had any more interesting places pierced!” Cassandra laughed. Wow! He liked her! And truth be told, she was physically attractive when you actually looked at her. Which he did: nice bust, pretty blue eyes, bright red hair you can’t get from a bottle. Honestly, most of the girls he had known in school probably would have been a little put off by the fact that he fell silent and just looked like that. He lost track for a moment.

“Simon, you are not exactly good at being subtle, are you?”

“What?”

“Well, you’re taking a good long look and I can see the wheels turning in your little head. Plus which, I don’t know if you remember, but when I got close to you on the controls of the airplane ride, you smelt my hair.”

“I remember. Your hair smells great. It’s got more than one scent to it, too. One of those mixed scents that guys can’t identify, but it’s very…girly.” She smiled again.

Much of the rest of the night was a blur. They didn’t drink that much, but got together in a corner and talked on and on for hours. Sometimes about work or people, but often about “Lost” or “Lord of the Rings.” She had a moist spot for science fiction that rivaled his hard-on for swords and sorcery. At some point, he had been looking at the curve of her breasts against her “Joss Whedon is My Master Now” t-shirt for just a little too long to tolerate, and he leaned in and kissed her. It was a nice soft kiss with just a touch of dancing tongues. The scent of her beautiful red hair filled his nostrils. He could have stayed in the moment forever if it weren’t for the feeling of someone watching them. He gently pulled back. Glasses was standing over them looking in askance.

“Cass, I know you’re probably having fun re-living the prom, but Carmen and I are bored to tears with this place. You riding home with us?”

“Well, Becca, I believe I’ll find my own way home, since I am obviously having making out with this handsome young man here.”

“Um-Cassandra—I rode my bicycle here. I only live a mile away.”

Glasses guffawed. It wasn’t appealing.

“Well, Becca, WE have decided to accept your ride back to my house,” Cassandra said.

“It’s really kind of you, to offer,” Simon said with a shit-eating grin.

The ride to Cassandra’s was really rather quiet. Glasses and Piercings were not amused with his presence. And Cassandra and Simon were fairly busy sucking face in the backseat. He did make sure to thank Glasses again for the ride.

Cassandra stayed with her parents during the summer, but it was a huge suburban house and she had her own entrance—kind of like Fonzie’s pad at the Cunningham’s house. Her room looked a lot different, though. A big king size bed with plenty of plenty of girly covers and walls decorated with posters of David Boreanaz, Nathan Fillion and Adam Baldwin. She was a hardcore Browncoat, but he noticed that when she walked into the room she paused for a moment, kissed her fingertips and touched her autographed picture of Anthony Stewart Head.

“Cassandra, I’m looking forward to this more than you can imagine, but if James Marsters or Nic Brendon turns up in the bed, I’m leaving.”

“Little boy, if James Marsters or Nic Brendon turns up in my bed, I’ll pay you 100 bucks to get it all on video!” Man, he really liked this chick. And even considering his serious naiveté, Simon was certain he was going to have his first ever sexual experience with her; right now.

He went right for the breasts as soon as they began to kiss, and she was more than okay with that. She pulled off both of their shirts in about ten seconds. She led him to the bed and laid him down. She straddled him and began to trace designs on his chest. Runes of some sort, he thought, but found them pointless since he was already totally under her spell. She took her own bra off, letting the objects of his fascination tumble out before him. “Damn!” he whispered.

“Simon. I have an awkward question for you. Am I—um popping your cherry tonight?”

“Yes.”

“Baby, I’m gonna treat you good. Just relax and enjoy, because I got a long list of things I think you’re gonna like.”

“That sounds good,” he said, massaging her breasts and wondering what could feel better than her grinding against the front of his shorts. Cassandra soon removed those shorts. She slid down, kissing his chest, and finally settling her full lips on his erection. He bucked and rose his hips high off the bed. He could tell that he was about to cum, and wondered exactly what he should do about that.

“Let it go, baby,” she whispered. He did, and she aimed it at her breasts. “Pearl necklace,” she whispered with a little laugh. She lowered herself onto him, crushing her breasts against him and sliding a little to spread his semen between them. It certainly was not what he was expecting, but he liked it. In the fog of his lust-saturated mind, it seemed fair somehow.

She rolled off him for a moment as she slid out of her own shorts and panties and kicked them to the floor. She reached into the bedside drawer and pulled out condoms. She opened one up and slid it over his penis, which had almost instantly returned to a full erection. Youth has its advantages. “Are you ready, Simon?” she said softly. He nodded. “You are a beautiful man, and I am glad to share this moment with you.” She straddled his erection and gently guided it into her. Suddenly he knew what it was that would be better than her grinding against him with their clothes on. She rocked back and forth gently for a while, changing angles and positions and letting him feel the pleasure of being inside her. He reached for her breasts, and she nodded as he began to massage them. She slowly pulled her self to an upright position and he reached up, trying to follow her breasts. She pushed him back down and began to play with her own breasts as she gently rode him. Soon, she dropped a hand to her crotch and began to massage her clit as she rocked back and forth. He watched in amazement as she began to really heat up.

Seized with an overwhelming outpouring of energy and lust, he reached up to her full hips and grabbed them firmly. He began thrusting up into her with all of his might. She was a little surprised, but adjusted quickly to this thrilling new stimulation. “Oh, hell yes,” she whispered as he continued to pick up speed. She closed her eyes and began to nod emphatically. “You’ve got the spot. Hammer me!” He drove himself in as deeply as he could go, time after time. She began to emit a little squeak and then a loud moan. Simon didn’t know much, but he knew that she was about to cum. She unleashed her passion with a triumphant, “Oh yes! Oh yes! Oh yes!” and then let herself collapse on top of him.

While she was older than Simon, she wasn’t older by much, and even a good hard orgasm didn’t leave her spent. Simon lay motionless and a little uncertain, but she knew what he needed. “Roll me over and fuck me until you finish, Baby.”

Simon knew what he had to do. He put Cassandra on her back and she drew her heels almost all the way up to her plump little rump. He crawled in between her legs and drove himself firmly into her welcoming body. He grabbed her by her surprisingly firm haunches and launched himself wildly for a moment until he found that there were different angles and speeds he could try. He decided to try and make it last. At one point, he picked her bottom up off the bed and let her grind her sweetness against him. He brought himself to a kneeling position and drove himself into her and pressed his groin against the ginger hair of her womanhood while he reached down and tweaked her nipples. “By the gods, I love your tits,” he whispered. She smiled and reached down between her legs and diddled herself while he enjoyed them for a few moments longer. Then he set to work on finishing their lusty enterprise. He realized that he had found an angle that hit the spot she had been touching on her own. He drove himself in on that angle for as long as he could, and just before he released his second orgasm, he was surprised to hear her enjoying a second of her own. He finally let go, and was certain there was no way the condom could hold so much semen, but when he collapsed and rolled away, everything seemed intact.

They both breathed heavily for a few moments. She handed him a Kleenex, and after a moment of looking perplexed, he figured out exactly how to remove the condom without making a mess.

“Well,” he said at last. “I’ll call ya.” He got up and pretended he was about to leave. She didn’t buy it for an instant. She just smiled and patted the bed next to her. He grabbed his cell phone from his pants and sat down next to her on the bed. She draped her arms over his shoulders from behind and watched him begin to text. “Mom, not coming home 2nite. Staying w/friend. Safe n sound.” He felt her breasts against his bare back. “n happy!” he added.