Academic Advising

"Hands on the desk," he told the blushing student, caressing her firm ass through her neon-pink panties. "You'll do what I say or you'll have an 8am lecture every day of the week, you understand? Your academic progress has been completely unacceptable and this is the only way to stay on track."

She'd walked in that afternoon carefree and innocent, just another sophomore coming back from summer vacation. She hadn't thought it was such a big deal, failing two of her classes last spring. Her blue eyes had widened as her advisor told her she was in danger of losing her scholarships, forced to move back home in humiliation. And Walter had known then that she was in the palm of his hand.

It had only taken a few minutes to convince Ashley that he could help her, could make all her problems go away, if only she'd be a good girl for him. She'd nodded uncomprehendingly. "Of course, Mr. Warren, I just want to keep attending this school. My parents would kill me if I flunked out. What can I do?"

What indeed. For starters, she could peel off her skinny jeans and let him have a good look at her long legs. She'd stammered out an excuse, pretended to be embarrassed, but with the merest words of encouragement-- "Do you want me to take care of you, or not?"--her pants were around her ankles. Ashley had bit her lip, staring at the floor, but clearly aroused by the forced exhibitionism. If she were truly uncomfortable with this arrangement, she would have run screaming to the dean's office by now. That's what Walter told himself as his lecherous gaze moved over her slim body.

And now he had her bent over his desk. A simple prompt was all it had required. If he didn't know better, he'd suspect that this particular student had been dreaming about being stuck in this position for a very long time... that, or she was just especially pliant. Hmm. How many college girls fantasized about their academic advisors?

"Ashley, my dear," he crooned over her shoulder, bucking his hips forward to rub his clothed erection against her underwear, "that's a good girl, assuming such a nice position for me. Now, why do you think I want you like this?"

"Uh, I don't know, Mr. Warren--"

"Sir. Call me Sir." The university didn't require students to be so formal, but he wanted to hear the word coming from her lips.

She swallowed, shivering a little at his command. Did she like being so obedient? "Yes, Sir. Um--you have me over your desk because--you want to fuck me?"

The term sounded especially vulgar when a woman so much younger than Walter was saying it to him. "Yes, sweetheart, that's right," he praised. "Of course I do. You've got such a plush ass." He dug his trimmed fingernails into it as he spoke, eliciting a whimper from the girl beneath him.

"I've got a tight little pussy too, Sir," she said, growing bolder by the minute. "All the guys say so."

"Really? How many young men have buried themselves in that slutty pussy, hmm?"

"I--I don't know... I don't keep track... Ten?" she offered helpfully.

"Hmm." His hand came down on her right ass cheek, hard enough to sting but not hard enough to bruise. "I like my holes a little...fresher. How about we change tack." Suddenly he was tugging at the waistband of her panties, pulling them down around her ankles. Her shirt was long enough to cover the top of her ass crack; he pulled it up and over her head, letting the fabric cover her face.

She struggled to turn around, but he planted a firm hand on her upper back, holding her in place. "Shhh. There's a good girl. How many boys have had your ass?"

"Mmph--" She worked her shirt out of the way enough to speak freely. "Nobody! No one! Sir--"

Her pleas were cut short as the older man reached around to stuff her panties in her mouth. "Good. That's very good. I think we're going to be able to make this a satisfactory meeting for us both." His fingers were tracing down her back, across her plump buttocks, between her soft thighs. One hand disappeared from a moment and returned wet and slick; Walter kept a pump-top bottle of lube hidden behind a file organizer on his desk. Sometimes while his colleagues left the office for lunch, he squirted a few drops into his hand and jerked himself off with the door locked and the blinds shut.

Ashley moaned as a single finger entered her virgin asshole, wriggling around in an effort to loosen her up and feel out the terrain. She could have stood up, run away, but the thought never crossed her mind. She was attracted to her advisor, she admitted it, although she hadn't expected to end up naked on his desk, let alone placed in such an unforeseen predicament. Why didn't he want her pussy? How depraved, taking her anal virginity without even properly asking for the honor of her first time. Her hips wiggled slightly at the thought. It was strangely arousing.

Walter continued pushing one digit in and out of the student's tight anus, watching it disappear over and over again, until her moans quieted. Time for another. He had thick fingers, good for stretching reluctant holes, good for wrapping around his own cock in moments alone. Good for thrusting in and out of wet cunts, too, but today that wasn't his mission. Ashley began to whimper again at the new intrusion, her hole fluttering around the unfamiliar invaders, and when even these noises subsided, a third finger entered, making her back arch as she let out a muffled wail.

"There, there," he soothed. "Almost ready..." Withdrawing his fingers, he stroked her back with one hand while searching for a condom in his desk drawer with the other. Once located, the packet was ripped open with both hands, followed by his too-tight dress pants, and the rubber was swiftly rolled down his flushed cock, eager for action.

"Now, here's a treat for you, my pet," Walter announced, pressing his engorged cockhead against the girl's tight ring, enjoying the sight of the puckered pink entrance tensing and relaxing around his tip. She was obviously doing her best to accommodate his wishes, her hands still on the desk, her mouth still stuffed with musky fabric. He'd been easy on her so far. It was time to make her regret making this appointment--just a little.

With one determined thrust, he sank his prick into her tight heat, his balls coming to rest against her cleft cheeks. His cock wasn't particularly long, but it was decently thick, with a pronounced mushroom head; she could certainly feel it inside her ass. Right on cue, Ashley let out a helpless noise that was halfway between a moan and a sob, more expressive than words could ever be. His dick jumped at the sound, twitching against her insides. He rested a moment before pulling out and sinking back in again, setting a moderate pace which he kept up for the next few minutes.

Ashley was shaking beneath him, head spinning at the sensation of being so utterly degraded: gagged and somewhat ineffectually blindfolded by her own clothing; fucked in the ass by her advisor in his own office. Surely he'd locked the door? She hoped she wasn't being too loud. If someone came in and saw her like this...

...she'd never come back to school again, regardless of grades or scholarships. It would be too humiliating.

Walter picked up the speed of his thrusts, too excited by the taboo nature of this encounter to hold back for long. He'd dreamed of taking one of his students over his desk for years, but never had the balls to actually go through with it. Then last month, his wife had left him, he'd learned that he was likely to be let go at the end of the year due to budget cuts, and he knew this was his chance, his time to act out his greatest fantasy. Ashley had walked in with a sway in her hips, a twinkle in her eye, and a poor academic record--and he seized on the heaven-sent opportunity without a moment's hesitation.

Her tight tunnel was almost too much for him, constricting around his cock even as he pumped in and out of her slickly, adding more lube whenever he felt the need. She felt so good, gripping him like that--did she even know what she was doing to him? His balls were slapping lewdly against her ass, he thought he could feel her pussy dripping beneath him, and her hips kept coming back to meet his. Oh, she was definitely into it. Maybe she hadn't been at first, but now... Now he'd fuck her for all he was worth.

Slamming into her, again and again; it was enough to make Walter's eyes roll back in his head. Little did he know Ashley had the same mind-broken expression on her pretty face, laying across his desk and drooling, finally accepting the filthiness of her situation. Her back arched--his hips stuttered--she was moaning, gasping, all her dirty little sounds muffled by the makeshift gag--he couldn't hold back any longer. With a low, guttural groan, he grabbed her hips and pulled her to him, cumming hard deep in her guts, filling the tip of the condom nearly to bursting. She felt his pace change; her whines grew higher, more desperate as she realized that he was finding his release.

His orgasm over, the two of them collapsed onto the solid wooden desk, breathing heavily. Ashley's pleasure had been completely ignored, but somehow she felt sated, enjoying the feeling of her advisor's thick dick slowly softening inside of her ass, his body pressed against hers. After a few moments, Walter looked at the clock on his monitor.

"Shit," he gasped, pulling out, tossing the full rubber in the trash underneath his desk, and hurriedly zipping up his fly. "Go, get out of here, I have another student at 4:30. Here--" He handed her a small mirror, distractedly combing his hair with his fingers and checking his clothing for wrinkles.

A few rushed moments later, Ashley's panties and jeans were back where they belonged, and the bewildered student was being ushered out of her advisor's office. "Don't tell anyone," he hissed in her ear as he patted her on the bottom. "And remember, I'll take care of your scholarship situation. Easy fix. Now go."

The girl all but ran out of the office, sure that every smiling face she passed on her way out of the building belonged to a person who knew what she'd done, how she'd just taken it up the ass for the first time. Her heart pounding, she made it back to her dorm without incident, although a few of the other students she passed gave her curious looks. Falling back onto her bed, she decided what she really needed was a nice hot shower, but it could wait... just until she finished fingering herself.