Cassandra Ch. 01

Cassandra had the perfect mix of innocence combined with a love for mischief that made her kind of slutty in a fun way. She was a petite brunette with about medium breasts, an olive skin tone and eyes that always seemed to dance nervously like she was questioning it all.

About the time she turned 18 was when she first met Glenn. Glenn would become this guy who she'd have an on-again-off-again relationship with, but it was more of a situation where he would use her and she would let him because she was absolutely obsessed with him. He played in a local rock band called the Church of Sodom.

She had known of Glenn and had thought that he was cute for some time before she had actually met him. The first time they met, he was just a really cool guy completely at ease with himself. He knew she had a thing for him; everybody knew! He didn't ever say anything for what seemed like forever. Until one time she came by to hang out and he decided that it was time to approach the subject.

Soon after they started dating, but it was nothing too intense, as he had already figured out that he wasn't too serious about her. She just didn't hold his interest.

After a short while, he called out of the blue to break up with her and this is when the obsession really began.

A few months later, about the beginning of her senior year, things picked back up. In order for her to remain close to him, she had made sure that she became friends with his friends and their girlfriends during the short time that they first dated.

They were at a lot of the same parties, and during their time apart she had started drinking more frequently and had joined in with the typical high school party crowd.

She had even hooked up with a few of his friends while drunk so she wasn't quite the innocent he thought she was before. She was always around it seemed and he knew exactly why. I wasn't long before he decided to take what was being offered.

One night while they were both alone outside a party for a smoke he started rubbing her ass almost "on accident" to gauge her reaction. She didn't even flinch. She slowly turned around as his hand kept its place and she flicked her cigarette away to kiss him while snuggling her body close to his.

Things started to heat up, quickened by the gained lack of inhibition from the alcohol, and he was holding her against the bulge in his baggy jeans. One hand was slightly up the back of her shirt resting on the small of her back and the other was down the back of her pants squeezing her bare ass. She was doing her part by rubbing his cock through his pants. He was easing his right hand deeper in the cleavage between her ass cheeks and found his way to her slit from the back. If she wasn't wet yet, she would be soon.

Or at least she would have been if it wasn't for the Maxwell sisters! Judy, with her sister Kristy, half-fell through the back door on their way out. Kristy, the younger redhead, was being helped by her at-least-a-little-bit-more-sober sister. Any thoughts of romance were wiped away by the sound of Kristy puking over the railing.

Deciding to let the sisters take care of themselves, they headed down the street. Glenn, being a couple of years older, had an apartment that wasn't too far away. After a couple of blocks they ducked through an alley and sidled up against someone's garage.

They continued to make out and she could feel his growing interest. His jeans were pretty baggy so it wasn't much of a problem to get her hand in his pants and around his dick. After a few minutes of making out, including the dry hand job, she wanted to see it by the light of the moon.

She pulled him out over the top of his pants as she began to kneel, kissing first down his neck and then at his torso through his shirt. He could feel her breath as she paused for a moment; nothing like leaving a guy hanging! She began by taking small, quick licks of the head and of the shaft, with the occasional nibble. This brought him to a full erection as she continued further with some skin-fluting before finally wrapping her mouth completely around the head and half way down the shaft.

She slowly pulled back while increasing the suction. A couple licks to keep it wet, then a little further down. She only used her hands to keep things in place as she continued sucking back, pulling more blood into the pockets.

It was one Hell-of-a-blowjob to say the very least! Warm and wet just like it should be. Its long slender form easily glided in her mouth. She had only blown a handful of guys, but she knew at least a thing or two.

After bringing him to the point that it was almost painful, she stood up and kept up a slow, loose hand job as she lightly nuzzled in his neck.

"We should probably get back to your place," she stated matter-of-factly while looking him dead in the eye.

After putting everything back in its proper place they continued walking. Glenn wasn't known for his romance, but tonight was an exception as he held her close to him.

When they got back to his apartment they saw a friend of theirs, Mike, having a smoke by the backdoor entrance to his own apartment. It was one of those old houses that had been converted into an upstairs and downstairs living space. They had another smoke and talked with Mike for a bit before heading inside.

Once inside she wasted no time, and without hesitation removed her shirt and her bra all at once. I wasn't the first time that he'd seen her topless but he still appreciated the view. There wasn't too much variation in her skin tone considering she didn't spend a lot of time out in the sun and her slightly darker complexion wasn't as affected by the UV light. They were damn near perfect breasts. 36C and with the firmness you'd expect of an 18 year old. She often complained that they made it difficult for her to enjoy certain activities like jumping on the trampoline or even jogging, but she had to be at least a little proud of her rack; especially considering it was placed on such a petit frame.

Glenn pulled his zip up hoodie and t-shirt over his head as Cassy once again knelt before him, taking his cock into her mouth. She multi-tasked this with taking off his pants as she increased his excitement. If she didn't ease off she'd be going home disappointed. She had his pants and everything down around his ankles but he was in no position to lift his legs out of either of them. Before Cassy could realize what was happening he came right in her throat! She had swallowed before but she was not a fan. She gagged on his semen as she watched his erection disappear.

He flashed her a sheepish grin, "Damn girl, you were just too good; but since it is getting late..." She knew where this was headed.

Glenn crawled into bed and rolled over away from her gaze. Cassy knew that her only options at this point were to go home, go back to the party or watch a movie on silent so she wouldn't disturb Glenn's sleep. She decided to head back to the party when you saw that Mike was still outside smoking.

Well, Cassy knew she could probably at least get laid from Mike. In fact, if he took her from behind she could just fantasize that it was Glenn fucking her instead. They had hooked up in the past, but she wasn't sure if she wanted to go that route. Mike could sometimes get too attached too easily, but there didn't seem to be any awkwardness before. It was worth a consideration at least.

Mike seemed kind of surprised to see Cassy walking out the door after a period of maybe ten minutes. Mike may have been a little slow (or perhaps he was always just a little too stoned) but he was a good guy that usually tried to do the right thing. "That was fast", was all Mike could muster without feeling like he was prying too much.

"Yeah, I guess He wasn't really in the mood, but it just sucks 'cause now I'm back to nothing to show for the night".

"Oh. Well... I'm not really sure why he brought you back here then. Kind of shitty if you ask me"

"Tell me about it. So, why didn't you go to the party tonight?"

"No reason, I just kind of felt like hangin' here. I was doing some reading earlier, but I decided to come outside and enjoy the Fall chill. I've got some beer if you want a drink."

"That's cool, but I've got my flask." She pulled out the flask she had found in her Fathers top desk drawer. He hadn't drank for years and probably didn't even realize that it was missing.

She took down a couple quick swigs and offered it to Mike who gladly drank some as well. This was some quality whiskey that she had stolen from her Mom and Step Dad, the kind that doesn't really burn the back of your throat.

Mike knew she really just wanted to be with Glenn, but it had been awhile since he'd gotten any and he wasn't in a position to not follow a potential lead. He invited Cassy inside and she accepted. That was a good sign. They both knew where this was probably heading, but they progressed slowly as they were both unsure of the others intentions. As they drank a bit more, and laughed a bit more, they started easing closer to each other. The sexual tension was building and Mike could feel the familiar straining in his jeans. She noticed it as well and took that as being permission to proceed. She started rubbing him through his jeans and moved in for a kiss. She was hoping that the whiskey and cigarettes would hide the fact that she had a mouth full of Glenn's cum less than an hour earlier. After making out for a short bit she asked if Mike had any protection. He nodded yes, and left to the bathroom to get some.

While he retrieved the condoms, she dropped her pants and pulled her underwear down to her feet. She wouldn't be staying so she didn't bother to completely remove any articles of clothing. She warmed herself up a bit while beginning her fantasies of Glenn. She could feel the delicious, damp warmth of her pussy as she slowly slid two fingers in and out with the slow rhythm of a deep and passionate fuck.

When Mike returned, he was already naked and removing the condom from its packaging. He was hard so she knew it wouldn't be long. She bent over at the front of his bed frame, turned her head back his way and made eye contact. She opened her legs and Mike knew how she wanted it. Once he had the condom secure, he slowly entered her from behind. She was so turned on she felt like she could pick out individual nerves jumping with excitement. In her mind, the hands on her hips belonged to Glenn. The cock in her pussy belonged to Glenn. She wished away the reality of getting fucked by Mike as she pictured Glenn ramming her to no end.

She couldn't help but let out a little whimper at the intensity she was feeling. He adjusted their positions slightly so he'd have a deeper angle. She could feel her juices as his dick continued stroking in and out. His soft hands (the only reminder that this was Mike) grabbed her hips, forcing them back to meet his thrusts. As his thrusts got harder, she imagined the strained look that would be on Glenn's face if he was really there. The slow, deep, hard thrusts sending her so close to the edge. Mike plunged into her faster and harder. If she could only keep the fantasy image in her head she knew she'd be able to cum!

Until, with an exasperated grunt, Mike gave way to his own orgasm. Although he continued with a few soft and weakened strokes, Cassy could feel him getting softer. She wouldn't be getting what she needed tonight. Spent, he collapsed onto her back somewhat; planting light kisses along the back of her neck.

Those kisses made her skin crawl. It was too intimate. This was a mistake. Worst of all, She wasn't sure if an orgasm would have really changed that feeling. She said something about needing to leave. Mike stood up, acutely aware of the awkward situation, not knowing what to say.

As she pulled her clothing back into position and fastened her pants she half heartedly said goodbye, unable to look him in the face. If she had, she would've seen a saddened look on Mike's face as he wondered what he did wrong. And that probably would've been too much emotion for her to handle at that moment.