Cassie’s Oral Education – Part One [Oral] [FFM]

Jack leaned back, stretched his arms over his head and yawned. He was having trouble focusing on the calculus text he was studying. It was almost 11 PM and he’d been at it for better than five hours. He’d pulled the same shift every day this week. The college library was starting to feel like his second home.

He blinked as he realized he was all but alone in the room. Only one other student remained, and that guy was hastily shoving his texts into a backpack, obviously eager to be on to something more exciting this Friday night.

The only other person in the library was Miss Delaware, the school librarian. He casually glanced over at her desk and his breath caught. She was perched prettily on the edge of her desk, dressed in a tight white silk blouse and a knee-length gray skirt, her long legs crossed in front of her, revealing just a hint of the creamy skin of her thighs. Her brunette hair was pulled back into a long ponytail, and her black-rimmed glasses sat on the end of her nose as she studied the book she was holding.

She was a fair bit older than he was, probably a little north of 30, but God was she hot. He wouldn’t have minded bending her over that desk and…

The door to the library swung closed with a loud click as his fellow student departed. The noise caused Miss Delaware to look up. She looked right at Jack. He flushed and swiftly buried his nose in his calculus book, praying she had missed his hungry gaze. After a minute he risked a quick peek out of the corner of his eye. She was studying him, her steepled fingers tapping against her full lips. She had uncrossed her legs, and was swinging them in front of her, offering tantalizing glimpses up her skirt every time her legs straightened. He realized he was gawking again, and averted his eyes, blushing even more furiously.

He heard her slide off her desk and start walking in his direction. “Please don’t come over here. Please don’t come over here,” he chanted under his breath, mortified that she might scold him for ogling her.

His wish didn’t come true. She stopped beside his chair, and he flinched as her fingers settled lightly on his shoulder. He looked up and saw her regarding him with a crooked smile.

“Studying late again Jack? It’s Friday night. Shouldn’t you be out somewhere trying to get into the panties of some lucky girl?”

He almost choked, and his face went beet red. He managed a weak grin and shook his head, his mouth working soundlessly. At the same time he felt his cock stir in his jeans. For some reason her casual use of the word panties had stoked a flame within him. He shifted slightly in his chair, and flushed anew when she gave him a knowing smirk.

She stepped behind him, both hands now resting on his shoulders. She began to massage the muscles, and he tilted his head to look up at her, his heart starting to pound.

“How old are you Jack? Twenty?” she asked.

He coughed, trying to work some moisture back into his throat. “Uh, twenty-one this past August,” he replied.

She smiled again, sliding her hands down his arms, giving his biceps a playful squeeze. “Twenty-one, legal for everything,” she murmured. She leaned forward and he nearly gasped as he felt her soft breasts touch the backs of his ears. His cock hardened painfully, and again he was struck dumb, not enough blood reaching his brain to process rational thought.

At that moment the door to the library swung open. Miss Delaware stepped back gracefully, and slid behind a bookshelf, out of the view of whoever was coming in.

Jack gave a start as he saw his friend Cassie enter. She spotted him and rushed over. He stayed seated, acutely aware of the protrusion in his pants and not wanting Cassie to see him in such a state.

She was in something of a state herself, he realized as she got closer. Her eyes were red and puffy, and it was pretty apparent she was really upset about something. As she plunked down in the seat next to him he also got the distinctive whiff of alcohol. She’d been drinking.

“Cassie, what’s wrong?” he asked.

“Derek dumped me,” she replied without preamble, her eyes shining with tears.

He reached out and grasped her hand. “I’m so sorry. What happened? No, never mind. You don’t have to spill. I can see that you’re upset.”

She gave him a sad smile, followed by an exasperated whack on the arm. “Of course I want to talk, silly. That’s why I came to you. You’re my best friend.”

He blushed, this time for entirely different reasons. Cassie and he had become friends early in his sophomore year, when she was a junior. He’d been seeing someone at the time, and so had she, so instead of romance blossoming, a friendship had. Since then they’d each been through multiple relationships, but had never been single at the same time, so the platonic state of their relationship had remained intact.

That’s not to say he hadn’t thought of getting together with her. Red-haired and so curvy his secret nickname for her was Jessica Rabbit, it was often hard for him to be around Cassie without his thoughts drifting to sex – particularly during those periods when he was single – like now.

He took a deep breath, still only too aware of the raging hard-on he hoped was hidden beneath the table. He gave her hand a squeeze. “So, why did that idiot dump you?”

She lowered her eyes and blushed, obviously embarrassed. “You’re going to think it’s stupid,” she mumbled.

“Never,” Jack promised.

“Because I wouldn’t give him a blowjob,” she confessed, the words tumbling out so fast he almost missed them.

“What?”

“I wouldn’t go down on him. He gave me an ultimatum: either get on my knees, or get out!” She choked on the last word, and she buried her face in her hands as sobs began to wrack her.

Jack reached out awkwardly to rub her shoulder, unsure of what to say. Though they’d been pretty open with each other over the past two-and-a-half years, they’d never gotten too in-depth when discussing sexual adventures. That policy had probably been for the best. He already had a healthy crush on her. If he’d been privy to the intimate details of her sex life it would only have inflamed his imagination further. He flushed guiltily as an image of Cassie on her knees in front of him flashed through his mind. The hardness in his cock had begun to abate but it returned with a vengeance at the mental picture. He flushed guiltily and shifted uncomfortably in his chair, trying to gather himself.

“He’s an asshole, and a complete moron for not realizing how lucky he was to have you,” Jack eventually managed.

Cassie sniffled and wiped her eyes, her smile sad and grateful at the same time. “You’re right, on both counts!” she declared. She giggled and covered her mouth, her eyes alight with amusement.

Jack smiled back. “Damn right I am,” he replied. “You withhold those ripe red lips of yours, baby. You only go down on those that deserve it!”

He was trying to be funny, but his words had the opposite effect on Cassie. Her face fell and tears started to spill down her face again.

“Cassie, I’m sorry. I was just trying to make you laugh,” he apologized.

She shook her head. “It’s not your fault. You just didn’t know.”

“Know what?” he asked.

She drew a shuddering breath and her blush returned, deeper than before. Her voice dropped to a whisper despite the emptiness of the library. “I’ve never given a blowjob before,” she confessed.

“For God’s sake girl! Why the hell not?” Miss Delaware demanded, materializing from behind the bookshelf where Jack had completely forgotten she was lurking.

Jack flinched and Cassie nearly jumped out of her skin. Her blush deepened to an alarmingly deep red as she realized the two of them were not alone. She looked wildly between Jack and Miss Delaware, anger and embarrassment and just a hint of curiosity warring across her features. After several long seconds she managed to regain a semblance of composure. She straightened up, and eyed Miss Delaware coldly. “What do you know about it?”

The librarian arched an eyebrow, lips twitching with amusement. “A very great deal actually. Enough to know that a beautiful girl like you, with a figure straight out of a swimsuit magazine, should never, ever get dumped. You should have guys eating out of your hand, not the other way around.”

Cassie suddenly looked very unsure of herself, flustered by the strange turn her private confession had suddenly taken. She looked to Jack for help, but if possible, he was even more bewildered than she was. Where was this going?

Miss Delaware came around the table and surprised Cassie by taking her hands. She tutted sadly. “Look at those luscious red lips of yours, just made for sucking. Are you saying you’ve never had a cock in your mouth? Not even in high school?”

Jack’s eyes nearly bulged out of his head at the crass question. He wanted to crawl under the table and hide. Cassie, surprisingly, didn’t blush, or try to pull her hands away. Instead, the curiosity in her eyes intensified. “No,” she whispered.

“Why not?” Miss Delaware asked.

Cassie lowered her eyes. “I was scared at first,” she admitted. “As the years went on and I still hadn’t done it, it started to become a bigger deal. Now that I’m older and supposed to be experienced, guys are going to have certain expectations. I’m afraid I’ll be so bad they’ll laugh at me,” she finished miserably.

Miss Delaware pulled Cassie into a hug. “Oh, you poor dear! It really isn’t as scary as you’ve built it up to be, and I can promise you that no guy is going to complain about getting a blowjob.”

Jack nodded unconsciously in agreement and Cassie reached over and gave him a smack.

“I’m still afraid I’ll do it wrong,” she complained.

Miss Delaware tugged on her lower lip, presumably deep in thought. Jack caught himself thinking how much he’d like to bite that lip and quickly looked away.

“I think I can help you,” she announced finally. Cassie gave her a blank look.

“Help me? What do you mean? Help me, how?”

“Why, I’m going to teach you how to give a blowjob. With Jack’s help, of course,” she added, her eyes dancing wickedly.

“What?” Jack and Cassie demanded in unison.

“Well, the best learning occurs when the student is able to have a hands-on experience. This way I can show you what to do firsthand. Then it will be your turn. I mean, I suppose a banana would do in a pinch, but why go that route when we have a handsome, virile young male at our disposal. Isn’t that right Jack?” she winked at him.

He realized his jaw was hanging open and shut it with an audible click. “Wait a minute. Did you say *show* her what to do?” he asked.

She gave him a naughty grin. “Of course. It is impossible to describe how to give a good blowjob. Cassie needs to see me in order to learn properly.”

“I’ll do it!” Cassie declared suddenly. Jack turned to look at her. He felt like he was in a waking dream. Two beautiful women wanted to practice oral sex with him as their training tool. It was beyond any fantasy he’d ever had. Still, he didn’t want to take advantage of his vulnerable friend.

“Cassie, I can’t, you’re drunk,” he said, the words more difficult than any he’d ever spoken in his life.

“What? I’m not drunk, you idiot!”

He gave her a puzzled look. “I can smell the booze on you.”

She gave him an irritated glare. “I had a shot of whiskey before I came here. I wanted to calm my nerves. You know I slur when I’m drunk. Do I sound like I’m slurring to you?”

He shook his head, his thoughts completely in disarray. Never in his wildest imaginings had he envisioned anything like this. “But you’re my friend,” he said feebly.

Her expression softened. “That’s exactly why it’s got to be you. I trust you, Jack. This isn’t exactly something that is going to work with some stranger.” She put a hand on her hip and pouted. “Don’t you find me attractive?” she asked, her eyes flashing wickedly.

He raised his hands in mock surrender. “I give up. If you ladies wish to have your way with me, who am I to stop you?”

He and Cassie shared a grin while Miss Delaware sauntered over to the entrance to the library. The click of the doors locking echoed loudly, and Jack gulped as she dimmed the lights. This was really happening. He stole another glance at Cassie. She looked as nervous as he felt, her chest heaving and her eyes a little wild now.

Miss Delaware gave them both an amused smile as she returned to the table. “No need to be nervous,” she said softly. “This is going to be fun.”

She tapped her fingers against her lip in that provocative way she had. “Where to start?” she mused. She eyed up Cassie, taking her measure. “I assume you have experience with men, aside from the whole blowjob thing?” she asked.

“W-what?” Cassie stammered.

“You’re not a virgin? You’ve been around the bases a time or two, right?”

Cassie blushed, but nodded. “Yes. I’ve been sexually active since I was sixteen, with several different guys.”

Miss Delaware nodded in approval. “Good, so you already know how to push a guy’s buttons. We’re not starting from scratch here.” She turned her attention to Jack. “And you? This won’t be a new experience for you, will it?”

He scoffed. “This? No, stuff like this happens to me all the time. Usually there are four or five women though.”

She gave an exasperated sigh, rolling her eyes at his sarcasm. “Not this exact scenario, obviously. But am I safe in assuming you’ve had your fair share of blowjobs?”

He nodded and mumbled, “I’ve done alright over the years.”

She clapped her hands together. “Excellent. An experienced partner will make this much easier.” She gave Cassie a wink. “Hard to give you a proper lesson if our subject’s gun keeps going off prematurely.”

Cassie snorted laughter and Jack glared at her. Looking back and forth between the two beautiful women who were about to go down on him he wasn’t confident his self-control would be up to Miss Delaware’s standards.

The librarian seemed to read his thoughts. “Don’t worry Jack. I’ll go easy on you,” she promised. “Now, let’s get started, shall we?” She motioned Jack towards her. He took a deep breath, got out of his chair and went to stand in front of her.

She stepped closer to him, close enough the tips of her breasts were brushing his chest. She smelled faintly of vanilla, and he unconsciously inhaled deeply. She smiled, obviously enjoying it as he swiftly slipped under her spell.

“This is going to be a lesson in three parts,” she told them. “Tonight’s lesson I like to call The Tease.”

“A lesson in *three* parts?” Jack squeaked.

“Three nights of practice should suffice,” she replied. “That should give Cassie a good solid foundation.”

Jack’s knees trembled. He had to do this three times? “Can’t we just squeeze in all three lessons tonight?” he asked.

She patted his cheek, her eyes dancing with mischief as she shook her head. “I admire your confidence Jack, I really do, but trust me when I say that you are going to need some recovery time between lessons.” Never taking her eyes off him she reached down between their bodies and gave his cock a playful squeeze. He gasped in surprise, his erect member twitching violently at her unexpected touch.

“Good to see you’re ready to go,” she purred. She turned to Cassie who was watching, clearly uncomfortable, yet intrigued at the same time. “As I was saying, tonight’s lesson is The Tease. This is a simple yet powerful technique, and is ideal for a couple’s first experience together.”

She reached back and untied her ponytail, shaking her long raven hair out so it cascaded over her shoulder. She looked into Jack’s eyes, and he felt himself drowning in twin pools of green. Never taking her eyes off him she began to slowly unbutton her blouse.

“What are you doing?” Cassie asked, looking around in alarm as though someone might be watching.

“A woman’s breasts are a formidable weapon when it comes to turning a man on. Surely you know that,” Miss Delaware said, nodding at Cassie’s voluptuous chest, which was straining the fabric of her tight sweater to the limit. “Though obviously not as important as your mouth in this scenario, they will play their part in heightening your partner’s ardor to the absolute limit.” She finished unbuttoning, and with a delicate shrug of her shoulders let her blouse fall to the floor.

Jack groaned against his will at the sight of her breasts, now hidden only by a lacy white bra. They weren’t nearly as large as Cassie’s, but they were full and perky, and he had to clench his hands at his sides to keep from reaching up and cupping them.

“See what I mean?” Miss Delaware said, giving Cassie a knowing smile. “Now, in a future lesson the bra will come off too, but with The Tease his imagination is your biggest ally. We just want to give him a taste to whet his appetite.”

Cassie nodded, soaking in the lesson, completely mesmerized.

“Your turn Jack. Take off your shirt please,” Miss Delaware commanded. His nervousness was long gone now and her eagerly complied, hastily tugging his t-shirt over his head and discarding it on the floor. She cooed appreciatively, running her fingertips over the hard muscles of his chest and abs. He glanced over at Cassie and found her staring hungrily at his torso. She flushed and quickly moved her eyes back to his face. He stifled a grin and turned his attention back to Miss Delaware.

She pressed closer to him, her soft breasts compressing against his chest. She turned her head, exposing her throat to him and giving him another dizzying wave of her scent. A low growl escaped him and he found himself wanting to nip at the exposed white flesh. The growl became a groan as she slowly began to slide down the front of his body. She continued her descent until her breasts reached the level of his groin. She paused there, her soft tits cushioning either side of his now completely engorged member. She reached around behind him, cupping his buttocks and giving them a subtle squeeze. His legs started to tremble beneath him, and his heart, already pounding, began to thunder in his chest. His cock was straining against the fabric of his jeans, and he silently willed her fingers to move to his zipper and give it its freedom.

Miss Delaware had other ideas though. She lingered there a moment longer, pushing her breasts back and forth over the back of his cock, then began to slowly move back up his body. As she stood, she unleashed her tongue on him, sliding it over his stomach and up to his chest. She paused as she reached his nipples. Her tongue circled his right nipple once, twice, three times, then without warning she gave it a nip. He grunted and pushed his hands into her hair, pushing her mouth against him.

She pushed back gently but firmly. She looked up at him and shook her head reprovingly. “Hands at your sides please,” she murmured. He took a deep breath and reluctantly complied.

She continued to torture him, sliding up and down his body, pausing at his groin and again at his nipples, using her breasts, her tongue and her teeth to drive him into a frenzy. All awareness of his surroundings was gone. He’d forgotten he was standing in the middle of a public library. He had even forgotten Cassie’s presence for the moment. All that existed was his tormented cock and the temptress who was abusing it.

She gave his nipple a long, loud suck then drew her lips slowly from him. She looked up at him, her eyes hooded and smoldering. “Mmmm. That was tasty, but I’m ready for something bigger now.” She reached down and squeezed his cock again, harder this time. “Yes, this is more like it.” She licked her lips and gave him a pleading look. “Jack, may I suck your cock? Please?”

He closed his eyes and groaned loudly, not trusting himself to speak. He gave her a shaky nod. She smiled and sunk down in front of him again, this time dropping to her knees. He held his breath as her fingertips deftly popped open the button of his fly. Her fingertips slid lightly up and down his shaft, still imprisoned in his jeans, before she finally relented, easing his zipper down. She gripped his pants and his boxers and in one quick motion yanked them down to his knees. His cock sprung free, and she gave a girlish giggle of surprise.

“It’s even bigger than I imagined,” she breathed, taking it in her hand and sliding her fingers up and down his length. She cupped his balls and squeezed them lightly, eliciting a loud moan in response. She licked her lips then bent her head over the tip of his penis. His whole body stiffened in anticipation and his hips rocked forward as he leaned to meet her mouth. Her lips were so tantalizingly close, but she raised her head and gave him an impish grin.

“My my, aren’t we anxious?” she teased. She gave Cassie a wink. “Are you taking notes?” she asked.

Cassie nodded, her gaze intent. She looked absolutely fascinated, Jack noted through the haze of his desire. Miss Delaware again bent her head over the tip of his cock. She blew lightly and he gasped, the nerve endings so sensitive that even a gentle caress of wind gave pleasure. With a sudden dip of her head she had his tip in her mouth. He gave an inarticulate cry and thrust his hips forward, trying to push his cock deeper into her mouth, but she anticipated his reaction and pulled her head back, releasing him. She gave his cock a hard squeeze then blew lightly on the tip again, her breath a cool contrast to her hot, wet mouth.

She repeated this procedure twice more and he had to clasp his hands behind his back to keep himself from grabbing the back of her head and holding her in place while he had his pleasure. She changed tactics. Slowly and deliberately she slid her tongue down the length of him. When she reached the base of his cock she took his balls in his mouth and sucked, gently at first then with increasing urgency. An electric tingle shot through him and he moaned again. He could already feel his orgasm building and she had only just begun. He took a deep breath, closed his eyes and steeled himself, determined to last.

Perhaps sensing his distress she pulled her mouth away from his balls. She gripped his shaft in one hand and began to work on him with her tongue again. Though still an immensely pleasurable feeling it allowed him to regain his composure somewhat and he felt his orgasm retreat.

She slid her lips over his tip again, then paused, swirling her tongue against the underside and moaning with pleasure.

“Please,” he begged. This was pure torture. All he wanted was to be deeper in her mouth, thrust to the hilt in that deliciously warm wetness.

Instead, she released him again. She turned and gave Cassie a wicked smile. “I love it when they beg.” She looked up at him. “Are you sure you can handle it?”

He wasn’t, but he nodded anyways. She smirked and bent back to the task. Her lips slid over him again, seemingly even hotter than before. This time they didn’t stop their descent, and he cried out as her mouth slid slowly down the length of him, taking him deep into her throat.

“Yes,” he whispered hoarsely, exhilarating in the feel of her mouth encasing him. His legs were trembling violently now. He pushed himself even deeper inside her and she didn’t resist him this time, opening her throat and welcoming his diamond-hard cock. She moaned loudly and sucked greedily at him. She slid her lips back up and down his shaft, more and more quickly, devouring him with a feverish intensity. He felt his orgasm building again, far more intense than before. He gritted his teeth, trying to fight the rising tide.

“Oh God, you feel so good,” he moaned. He was so close now. Another five seconds and he would explode inside her. “Yes, yes, yes, yes, arghh!” he cried out in pain and surprise as her teeth clamped hard over the tip of his penis. He was right on the cusp of spilling into her mouth, but the shocking agony of her teeth digging into him caused the orgasm to retreat once again.

“What are you doing?” he demanded hoarsely as she finally released his cock from between her teeth. Confused and angry and with bluer balls than he’d ever had in his life he glared down at her.

Part two coming soon!

Source: reddit.com/r/eroticliterature/comments/eq3a1l/cassies_oral_education_part_one_oral_ffm