0 comments/ 31209 views/ 4 favorites Simple Simon By: Simon_Magus Class was finally over for Simon. He was just an average college student; despite trying to play the nice guy most of the time. On the way back from class Simon had noticed some homeless people, and one in particular. She seemed different from the other homeless people there; she had a glint of intelligence in her deep blue eyes that was rarely seen in the homeless of the area. Her face was also clear and could almost be described as beautiful. The face was about the only thing you could see of her with her wearing at least five layers of clothing and dirty, floppy hat. Simon walked up to her. “Hi there,” he said standing right in front of her. She looked up at him and gave Simon an instant look of distrust. “What do you want?” “I would just like the pleasure of your company.” He said with a smirk. She still had a look of distrust and disbelief in her eyes. “Don’t worry, just a simple walk and talk. And I’ll make it worth your effort.” Simon extended his hand to her to help her from her sitting position on the ground. “What do I get?” Her look of disbelief and distrust had faded. “You get simple comforts that you have been without for what looks like a while,” he said and with that she took his hand and rose to stand beside him. She simply nodded and they were on their way. They talked at much length about seemingly unimportant topics. It was a long walk back to Simon’s dorm but neither of them seemed to notice. She was genuinely enjoying the company of this stranger, she couldn’t figure out exactly why, but she found him attractive. “Ok, we’re here,” she said, “now where is my reward?” They had reached their destination, and it was time for Simon to giver the woman her reward. Simon led her in to his dorm room. It wasn’t a very big room, but it had all of the comforts of home. “Your reward is here, you get use of the shower, which is something you are in dire need of, and after that I’ll take you out for a meal,” he put it simple and straight. The gifts were enough for her though, and he was right, she hadn’t had a shower in a very long time and it would feel good to be clean again. She smiled and nodded at him and disappeared into the bathroom. Within seconds her clothes were off and on the floor. She started the water and looked for a washcloth and the soap, there was none. The woman quickly wrapped a towel around her and went back to the room with Simon. Simon knew why she was back before she could ask for the soap and washcloth. He was stunned at how good she looked in that towel that he had an instant hard on as soon as she walked in. Simon handed her the missing items. “There is also a razor in there that you can use,” he said. She was embarrassed. She had completely forgotten that it had been quite a while since she had shaved her legs or anything. Her hopes had been that the focus would have stayed on her breasts, which were barely covered by the towel. “Thanks,” she said, “by the way, my name is Kristy.” She disappeared back into the shower. The first thing Kristy did when she got into the shower was shaved her legs and armpits. It has been way too long since I did this last, she thought, I almost feel like a woman again. She decided then that it was also time to shave her cunt too. After washing her hair and the rest of her body, she took time to inspect it. Kristy felt normal again, and it excited her. Her hands massaged her breasts. She started to get wet between her thighs and it was the first time in years. Living on the streets had been rough, but now was her time. Kristy’s right hand started to wonder away from the right nipple, which was swollen and sensitive from play, and found its way to the wet pussy. Her fingers gently massaged the clit, but it had been such a long time since she had felt this good that she was quickly to orgasm. Fuck, she thought, I finally get a chance to masturbate and I cum too quickly to enjoy it. Kristy exited the shower and went back to Simon wrapped up in a towel again, not wanting to put on her smelly clothes while she was this clean. Simon was in shock again when Kristy came back in with only a towel. He also finally too a good look at what she looked like. Her hair was still wet and sleeked back, but he could tell that it was redder than he had first thought. Her breasts amazed him, his first impression was that of a small B cup, but in reality she was a full C cup. The rest of her body was trim and a firm, tight ass that was the end of the sexiest legs he had ever seen. At some point she had asked him for something to put on, but still mesmerized by her beauty that he threw her clothes at random. She ended up with a t-shirt and a pair of jeans. Both seemed to fit fairly well. Her meal was whatever she wanted at a restaurant across the street from the dorm. It was all good enough for her since she was just glad to finally get a decent meal. Most of what she ate previously was scraps from restaurant trash or the local soup kitchen. Neither appealed to her. Kristy pigged out on whatever she could get her hands on. Soon enough later the meal was over, and so was the reward. They slowly wandered back to the dorm. Kristy was sorry that it had to end. “Look,” Simon said, “it is suppose to be really cold out tonight and I would worry having you out on the street so why don’t you just spend the night in here.” “Really?” she asked with a look of pure joy in here beautiful blue eyes. “Yep,” Simon said. They had really enjoyed each other’s company and neither wanted to separate from the other. “You can sleep in the bed, I’ll take the futon.” Simon grabbed a blanket and went to the futon. He stripped down to his boxers and crawled under his blanket. Kristen did similar and went to the bed and stripped her clothes off and crawled under the covers. She didn’t sleep much that night; she had spent too many nights on benches and under streetlights to be comfortable in a bed. She just watched Simon sleep. At some point during the night, Simon had kicked off his blanket and was sprawled out on the futon in just thin boxers. Kristy watched him grow a hard on as he fidgeted on the futon. She had gotten wet herself at watching the spectacle. Her fingers were slowly massaging her clit and nipples. She was careful though; she didn’t want to have to explain a massive wet spot on the sheets when she came. Morning finally came and Simon, who was a creature of habit, got up to take his morning shower. He hadn’t noticed that Kristy was finally asleep and her breasts exposed, nor did he notice that her clothes were still in the bathroom; he just got in the shower. He was there for the main purpose of releasing the tension of his morning wood. Kristy heard the sound of the water running and woke up. She remembered Simon’s late night stiffness and got excited. She crawled out of bed and wrapped a towel around herself, this time only around her waist leaving her chest free. She proceeded to open the bathroom door quietly, as not to disturb Simon. Her nipples were still red and sensitive from their all night play, but now they were also hard with excitement. She felt herself getting wetter by the minute. She peeked through the shower curtain and saw that Simon was in deep concentration with his hands on his cock. She slowly slid the shower curtain further and further. When it was almost all of the way open she stood back and said, “Hey, why are you doing that to yourself when you have a perfectly good woman right here?” Simon instantly froze and his face turned beat red. There was nothing that he could do; he just stood there with his tool in his hand staring at the tits of the woman in front of him. “So what were you thinking about while you were washing yourself so vigorously?” she asked after a little while of staring at his manhood. “To tell you the truth,” He managed to squeak out, “I was thinking of those.” He pointed the hand that was on his cock at Kristy’s glorious breasts. “So come here and take them,” she said cupping her breasts as if to present them to him. Simon almost lunged at her. Kissing her firmly on the lips and groping at her tits harshly as he was frustrated at being interrupted during his beat off session. His erection had pushed in on her towel that the towel fell off as soon as they embraced. Kristy felt his massive dick between her legs and became soaking. She had to have him NOW. She pushed him back into the shower and against the sidewall of it. Kristy was ravenous; she got on her tiptoes and then lowered herself onto his cock. At this point he took back control and grabbed her waist and began pumping her at a furious rate. They were both in ecstasy. This was the first time she had had a man in her in ages. After much time, she came, and came hard. She collapsed and was on the floor of the shower panting. Simon hadn’t cum yet, and she could see that. He helped her up to her knees and placed himself between her perfect breasts. She smiled and squeezed her tits together and began to bob up and down. Simon rammed his cock through her melons. It wasn’t long before his cum covered her face and tits. Kristy lapped it up from his cock like it was the nectar of the god, and rubbed it into her skin like lotion. He fell onto the floor with her. They embraced once again gazing into each other’s eyes. Later he offered for her to live there with him, and she accepted. Simple Simon +++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.