As Christian stared out of the window on the bus ride home from school, he kept replaying the events of the day over and over in his head.
He had been sitting in his senior year biology class, reading over some class notes after the lecture had finished, when he felt a tap on his shoulder. Turning, his breath caught in his throat as he came face to face with the brightest set of blue eyes that he had ever seen in his life. A moment passed and he began to blush after realizing that he'd been staring at Tiffany Andrews, one of the girls in his class and the love of his life, a fact that was unbeknownst to her. Tiffany giggled and then smiled shyly, allowing Christian to see precisely why she drove him to his knees. While like any other man, Christian loved the curves of a woman's body, he was first and foremost passionate about a woman's facial features, of which Tiffany's were his ideal: her aforementioned bright, blue eyes that shone as if there were irradiated by the sun, her delicate nose and mouth, and her incredibly sexy cheekbones. She also had long, silky, brown hair that possessed a natural curl and came to just below her long, graceful neck. Finally, as the piece de resistance, she had a smattering of light freckles across her cheeks and nose that added to her air of innocence and intense sexiness; Christian had often dreamed about coming all over them after Tiffany had fucked him with her throat.
Perhaps not surprisingly, her body was amazing as well: big, handful-sized breasts that always pushed against her tops, a tight stomach that could frequently be seen from her midriff-baring shirts, and long, sculpted legs that ended in a heart-shaped, juicy ass. She was a little bit on the taller side at 5'6", and was generally in great, toned shape. In short, she was perfect.
After the brief moment of awkwardness had passed, they exchanged short pleasantries and talked a bit about their classes and mutual friends; while the two had spoken on several occasions and were friendly with one another, Christian felt that he hadn't had the chance to get to know her as well as he would have liked, and her chronically busy schedule had kept his from asking her to do something together outside of school. The one thing that had never ceased to baffle him, and yet relieved him to no end was the fact that she had never had a boyfriend throughout high school. While there was of course some speculation as to the orientation of her sexuality, the way that she subtly flirted with him left him with no doubt that she found men to be attractive.
Eventually, Tiffany got to the head of their conversation by mentioning that she had been really enjoying their biology class, but that she was having some difficulty with the last couple of units. As the pair had a test coming up in a couple of weeks, she wanted to know if he would be willing to get together sometime and have a study session. After answering in the affirmative and setting up a date for the upcoming Friday night, it suddenly dawned on Christian what had just happened, leaving him flabbergasted.
Entering his empty house, Christian threw down his backpack, took off his shoes, and headed straight to his room. Upon entering, he flipped on his PC, took a piss in the adjoining bathroom, and began to strip his clothes off. After taking his pants off he noticed that his cock had slipped through the front hole of his boxers, and it was sticking out obscenely into the air. Removing his final article of clothing (after some careful bending to get out of his underwear), he began to gently jerk his cock and moved over to his full-length mirror. Staring back at him was a 6'3", 185lbs, 18 year old male who looked like he was about to cum. Letting go of his penis, he continued to check himself out to make sure that he would be the perfect specimen for his upcoming study date. Semi-short, shaggy brown hair, blue eyes, handsome face, reasonably built body from hours spent at the gym, hint of a six pack stomach, and a lovely, circumcised cock weighing in at 6.5 inches long and 5 inches around. "She should be fairly pleased," he thought to himself.
Lightly stroking himself again, Christian made his way to his desk and sat down in front of the computer. Logging into the internet, he opened up windows to his two favourite sites: literotica and a picture gallery link site. After some brief searching, he found two items that caught his interest: a story about a young high school girl who had a fetish for sticking dildos in her ass, and a couple of websites that had sample pics and movies of guys and girls licking, fingering, and fucking one another's asses. He also found a series of comics in which anime girls also had penises and were fucking one another with them. Feeling the cum boiling in his balls, Christian let go of his erection and began to play with his sack instead, wanting his orgasm to build up even further.
After a while he found another story to read, this one being about a pair of high school guys going on a camping trip before starting college. The two were out on a hike in the woods one day when they came across a girl masturbating in a clearing. She caught them beating off while looking at her, and offered to let them fuck her if they did whatever she said. Going back to her cabin, she came back with some lube and had them fuck each other in the ass before letting them take her in the pussy and ass at the same time.
Finally, Christian couldn't take it any more and went into his bathroom. From under the counter he removed a bottle of oil, put it on the side of the bathtub, and got in. Generously lubing up his hand, he began to gently rub his anus and moaned with pleasure. After a couple of minutes of rubbing, he took his index finger and slowly pushed it in and out of his ass, massaging his prostate in the process. Getting into a good rhythm, he started to stroke his raging erection with his other hand, and within minutes he began to cum in buckets, imagining that he was doing so all over Tiffany's freckles and big tits. Sperm shot into the air and landed on Christian's hand, cock, stomach, chest, and face as he cried out in pleasure. With each spurt, he could feel his anal muscles contracting around his finger, sending additional waves of pleasure through his body. Breathing heavily, Christian continued to stroke his cock as the orgasm subsided and he basked in the glow of pleasure that he had just experienced.
Friday came along very quickly, and Christian was as nervous as hell. Tiffany sat beside him in class that day and they had gotten along very well, which helped to put him at ease, and yet he still felt that there was a lot riding on the upcoming evening. Should he tell her how he felt about her? She he try and kiss her? If she rejected him, would he be able to handle it? In any event, he was still elated at the chance to even spend time with this amazing girl, and he knew that if things were meant to be, they would work out. One thing that he knew he had to remember was not to stare at her when they were studying tonight. Having been stealing glances at her all day, she was looking as sexy as ever in her tight, low-rise jeans, white button up shirt with a v-neck sweater over top, and hair put up in a messy twist at the back of her head, something that showed off her perfect face to him even more.
After class was over, the pair walked back to Christian's place at a leisurely pace, continuing the chat that they'd been having through the day. Christian was elated to learn that the two had a good deal in common and that they meshed together very well. Both were flirting openly, and it seemed as if things couldn't be going any better.
Upon arriving at his house, Christian led Tiffany, or Tiff as he was now calling her, to the kitchen where he proceeded to make a batch of grilled cheese sandwiches. As the pair of them ate, Christian couldn't help but notice how cute Tiffany was when she was taking little nibbles of her sandwich: the way that her mouth moved when she was chewing, the half-smile that she was forced to make when she was talking with food in one cheek, and the way her eyes shone when she was talking or listening to him…
"Christian?" Tiffany asked, snapping Christian from his lovebird daze.
"What? Oh, sorry, what were you saying, Tiff?" Christian replied, having no idea where they were in their conversation.
"I was just asking you where you learned to make such great grilled cheese. It's really tasty!"
"Oh, you know, just lots of practice I guess. It's made with organic cheese, so maybe that's the difference?"
"Maybe….Chris, I have to ask you something," Tiffany said as she adjusted herself in her seat at the table. Christian couldn't be positive, but he thought he saw her move her chair a bit closer to him in the process.
"Sure, what's up?" Christian replied.
"Well," Tiff began, "I've noticed that over the course of our knowing each other, as we've been becoming friends, you always seem a bit…surprised when you see me. And sometimes, like just now, you sort of just zone out when I'm talking to you. Have you noticed that, too?"
"Yeah, I guess so…" Christian replied.
"Well, I really like you, and I find that we get along together really well, but I'm just sort of worried…I guess what I'm trying to say is that if you feel that I'm bothering you at any point, or if you think that I was being a bit imposing by asking you to study with me, then you can just tell me and I can back off."
Completely thrown off his guard by her words, Christian couldn't help but laugh; she couldn't be farther from the truth!
"What's so funny?" Tiffany asked, a slight smile on her beautiful face, and yet a tone of seriousness in her voice.
"Oh, it's nothing," Christian replied. "It's just that that's not it at all."
