She looked up at him and batted her eyes winsomely at him. “As badly as I want to taste that hot, sweet cum of yours I’m trying to teach a lesson here. Cassie needs to learn how to take a full load, and you’re going to give it to her.” She gave Cassie a devilish grin. Jack looked uncertainly at Cassie, but she was staring at his engorged member, which was standing as straight as a mast, glistening with the saliva of Miss Delaware’s hungry assault. He blinked as he saw the naked lust in her eyes. He growled low in his throat, his ardor rising once more.
“Your turn Cassie,” Miss Delaware said. She got to her feet, retrieving her discarded blouse. She turned her back to them, ridiculously modest considering what had just happened, and buttoned up before turning back to face them both.
“Are you ready, honey?” she asked Cassie. Cassie drew a deep breath and nodded firmly, her eyes still lingering on Jack’s erect penis.
The librarian gave her an encouraging smile. “Good. As you can see, he’s more than ready. Why don’t you take that sweater off and let those big, beautiful breasts of yours out to play.”
Cassie did as asked, reaching up and tugging her sweater up and over her head. Her glorious breasts spilled out, heavy and full and pushed up to their fullest advantage in a tight red satin bra. Jack stared as her prodigious bosom and started to pant in response.
Cassie wasn’t done disrobing, however. With a sultry wink at Miss Delaware she unzipped the tight black slacks she was wearing and pushed them down to her feet before stepping lightly out of them. The librarian gave her an approving nod.
It didn’t seem physically possible but Jack felt his cock harden even more at the sight of her in just a bra and matching skimpy red panties. Her curvy figure called to the most primal part of his brain, and his vision misted with a red haze as lust completely overwhelmed him.
She sauntered towards him, exaggerating those beautiful curves even more. He stood stock still, afraid that the slightest movement might scare her off and end this beautiful dream he found himself starring in. She slowed but didn’t come to a complete stop until the tip of his cock pushed up against her belly button. He thrilled at the intimate contact and stared at her, drinking in her incredible beauty as she stood in front of him, nearly naked, chest heaving with equal parts nervousness and lust.
She reached out almost gingerly and caressed the muscles of his shoulders and arms. She stepped closer, pushing her breasts against him and forcing his cock straight up between their bodies.
She looked into his eyes. “Thanks for doing this for me Jack,” she said.
He almost laughed at the sheer absurdity of the statement, but the sincerity in her eyes stopped him. He swallowed and gave her a reassuring nod. “My pleasure,” he replied.
She arched an eyebrow, then leaned in and nipped him hard on the earlobe. “It will be,” she promised. She continued to suckle at him for several seconds and he closed his eyes, enjoying the intimacy that he’d often imagined with her.
Her lips traveled from his ear to his neck, and then across the stubble of his jawline. He turned his lips to meet hers, trying to steal a kiss, and felt a stab of disappointment as she turned her head away with a shy smile. Disappointment faded fast, however, as she slowly sank to her knees in front of him.
Like Miss Delaware had, she pushed her breasts against either side of his cock. The sheer size of her tits completely encased him in pillowy softness, and he moaned loudly as she slid up down, her hands pushed hard into the side of her breasts, fucking him with her tits. He started to bend and straighten his knees, moving in opposite time to her, panting now as she stoked his lust.
“Careful,” Miss Delaware cautioned. “You’re getting him pretty worked up, and he was quite near the brink to begin with. Let him cool down a bit.”
Cassie smirked. She stopped moving and looked up at him, green eyes innocent and wide. “You having some trouble there, tiger?” she teased.
“A little,” he croaked.
“Poor dear,” she commiserated. She released his cock from its pillowy prison and regarded it thoughtfully. “It *is* big, isn’t it?” she said to Miss Delaware, who was still watching with a critical eye.
“Mmm hmmm,” the librarian agreed, desire plainly evident in her eyes.
Jack blushed and cleared his throat awkwardly. “Will you two stop it? I’m not a piece of meat, you know.”
Cassie arched an eyebrow at him. “Oh? Are you feeling taken advantage of? Shall I stop now?” She made as if to stand up, but he put his hands on her shoulders pushing her down.
“Um, that would be a no,” he replied.
The next ten minutes Jack learned why it was often said that there was a fine line between pleasure and pain. The experience was almost akin to torture as Cassie brought him to the brink of pleasure again and again, never quite letting him pass the threshold into release. She had obviously taken Miss Delaware’s lessons to heart and was doing a masterful job of emulating the sexy librarian, even throwing in a few twists of her own to torment him. Finally he couldn’t take anymore.
“Please Cassie, let me cum!” he pleaded.
“You’re right. It is nice when they beg,” Cassie said, sharing a grin with Miss Delaware.
She bent back to his cock and set to work, lips sliding up and down him hungrily. She reached between his legs and cupped his balls, her hand squeezing each time her mouth reached the base of his penis. He felt his pleasure rising, and knew that she sensed it too. Instead of backing off this time she increased her pace, gobbling him greedily as he thrust deeper into her mouth.
“Oh God, Cassie! Oh Cassie! Oh Cassie! Yes, Cassie! Yes!” His orgasm hit him with the force of a tsunami, more intense by far than any he’d experienced in his life. His whole body shook with the explosion of his lust, and he thrust as hard as he could, pumping hot semen down Cassie’s throat.
Cassie weathered the flood, drinking him hungrily as he spilled into her, even moaning with the pleasure of the act, though her moans were drowned out by his cries of ecstasy. Finally the torrent ended and he was left weak-kneed and shaking, Cassie’s mouth still wrapped around him as she drank down the last few drops. Finally she finished and slowly pulled his cock from her mouth.
“My God, Cassie, that was fucking incredible!” he breathed fervently.
A huge grin split her face as she looked up at him. “Really? You’re not just saying that? I was good?”
He nodded vigorously. “More than good. You were amazing. Are you sure you’ve never done that before?”
She shook her head shyly. “Miss Delaware had you pretty worked up before I got my mouth on you,” she protested. “That’s probably what made it seem so intense.”
“True, but even with the ‘warm-up’ it still would have been mind-blowing. Seriously Cassie, that was the best oral I’ve ever had. And I’ve had a lot,” he told her with a smirk.
Slow clapping interrupted them, and Jack swiveled to see Miss Delaware walking towards them. His lust satiated, Jack suddenly felt self-conscious. He helped Cassie to her feet before hiking up his boxers and jeans, keeping his eyes studiously on the floor until he’d managed to get himself sorted. When he looked up again Miss Delaware was watching him with an amused smile.
Beside him Cassie was getting dressed as well, though she was taking her time, not afflicted by a sudden bout of modesty like he had been.
“Congratulations Cassie. You’ve given your first blowjob. Pretty successfully I might add, given the condition of our young friend here,” Miss Delaware said, inclining her head towards Jack.
Cassie beamed, obviously over the moon at overcoming the sexual hurdle that had plagued her through her teenage years and into her adult life. “Thank you, Miss Delaware, and thank you too Jack.” She regarded him solemnly. “I mean it.”
He still felt ridiculous at being thanked for what had just occurred, but he just smiled and said. “It was my pleasure.”
“There’ll be more pleasure coming your way, Jack,” Miss Delaware promised. “Remember, I’ll need another two nights with you and Cassie to complete her oral education. Go home and get some rest. You’re going to need it.”
The next day was a hazy blur for Jack. Despite Miss Delaware’s admonition that he rest up, the memory of the night before and the promise of what was to come completely encompassed his thoughts, allowing him only brief snatches of sleep before he was awakened by fevered dreams of Cassie and Miss Delaware savaging his cock. His brain was only half the problem though. At twenty-one, Jack was a virile young man, and his body wasn’t about to let him forget it. As he began to get ready for class he found himself walking around his room in a constant state of arousal, cock hard against the inside of his jeans. Unable to quell his desire, and knowing he would be incapable of maintaining any sort of concentration anyway, he skipped his classes for the first time since his freshman year.
His second night in the library was even more erotic than the first. Miss Delaware taught Cassie the technique she laughingly referred to as The Gobbler. This was the art of giving the sloppiest, messiest, most enthusiastic blowjob imaginable. She and Cassie took turns eating his cock like it was an ice cream cone and they hadn’t had a meal in days. At one point they’d double-teamed him, tongues working eagerly over opposite sides of his bulging shaft. Somehow he’d managed not to blow his wad at that point. He still wasn’t sure where he’d found the discipline. It hadn’t helped that both women had been completely topless at the time, bare breasts rubbing enticingly against his thighs as they pleasured him with their tongues.
They’d brought him to the brink and then Miss Delaware had given the reins to Cassie to finish him off. It had happened quickly and was again so violent his eyes had almost bulged out of his head. Just as he’d hit his climax she’d pulled her mouth off him and leaned back, making him cum all over her tits. It had been hot as hell, and had even trumped the previous night as the best oral he’d ever had.
Now it was day three, and again he’d had little sleep, spending the night visualizing in vivid detail the events of the past 48 hours. He’d even tried masturbating, hoping that the relief would allow him some respite from his sexual imaginings, but it was hopeless. Five minutes after spilling he was again hard as a rock, thoughts of Cassie’s ripe mouth on him driving him wild.
He arrived in the library at their arranged time, his exhaustion forgotten as lust began to thrum through his body. Cassie was already there, deep in conversation with Miss Delaware. They cut off abruptly as he entered the room, and as he drew near he could see that Cassie was blushing furiously.
“What are you two seductresses cooking up for me tonight?” he demanded as he approached the table. Both gave him looks of wide-eyed innocence in response, their four eyes twinkling mischievously back at him.
“Fine, keep your secrets,” he taunted them. “It’s not like you can top last night.”
“Oooh, that sounds like a challenge,” Miss Delaware replied, eyes suddenly smoldering with hungry promise. The look was so intense that Jack had to catch himself from taking a step backwards.
“Don’t worry Jack, I don’t bite,” she said, taking a step towards him.
“That’s not how I remember it,” he said, wincing at the memory of her teeth clamping down on his cock that first night, forestalling him from cumming before Cassie had had a chance at him.
“What? Oh, that’s right! I guess I do sometimes,” she giggled, surprising him by blushing. “Well, you’ve got nothing to worry about. Cassie’s giving a solo performance tonight. I’m just going to be observing.”
He would have been lying if he’d denied feeling a twinge of disappointment at the news. Having two incredibly beautiful women worshipping his cock with their mouths had been an intense turn-on. Still, this was the last night – Cassie’s final exam, so to speak – so he was eager to find out what Miss Delaware had lined up for tonight’s lesson plan.
“Tonight’s technique is The Submissive,” she told him. “It is incredibly intimate and requires absolute trust between the man and woman. Cassie will be completely at the mercy of your lust and of your self-control the whole time.” She gave him a sharp look as she imparted this information. He met her eyes and nodded solemnly in understanding.
“There are many variations to this technique, and it invites all kinds of naughty possibilities,” she said, adjusting her gaze so that it encompassed both of them. “It works very well as a second half act to The Tease, and bindings and blindfolds can give it extra stimulation.” She paused, deliberately loosening the long tie she wore around her neck. She removed the knot and moved over to stand behind Cassie.
“Arms behind your back,” she commanded. Cassie complied without a word of protest. Miss Delaware twined the tie around Cassie’s wrists, snugging the makeshift binding. Satisfied, she stepped back. “On your knees,” she said, gesturing to the floor. Cassie sank down slowly, her short skirt riding up as her bare knees sunk into the carpet.
“Jack, come here,” Miss Delaware told him. He stumbled forward, mouth dry at the sight of Cassie bound and on her knees before him. “Unzip, and pull your cock out,” Miss Delaware prompted. He gulped and did as he was told. His member sprang up out of his boxers, huge and red and already throbbing with need.
“Cassie, take him in your mouth. Just the tip, mind you. Remember, he is the one in control tonight.” Jack gasped as she opened her mouth and obediently slid her lips over the sensitive tip of his penis.
“Now Jack, you reach behind and grab Cassie’s hair. Some couples like it rougher than others, but I’d recommend a gentle touch for your first time,” she instructed.
Jack gulped and twined his hands through Cassie’s hair, palms resting gently on the back of her head. She trembled slightly under his touch, but was otherwise stock-still, waiting for him to guide her.
“Okay Jack, use Cassie to pleasure yourself. Show her exactly how you like it, how fast, how hard and how deep.”
He took a deep, shuddering breath, unnerved by the power he held over the beautiful woman sitting bound and waiting, her mouth still wrapped around the tip of his cock. Slowly, and very deliberately, not wanting to seem too eager, he pushed on the back of her head. He encountered no resistance, and he groaned as her lips slid down the length of his cock. He paused, reveling in the feel of being deep in her throat, her ripe lips resting lightly against his balls. He pulled lightly on her hair and her mouth retraced its path, sliding back until her lips were barely touching the tip of his glistening cock.
“Blow on it,” he commanded, settling into his role as the dominant. He was vaguely aware of Miss Delaware murmuring her approval. Cassie responded without hesitation, blowing lightly on his wet penis, the cool air of her breath pebbling his skin.
He pushed her mouth back over him, more forcefully this time and groaned again at the contrast between his cooled skin and her hot mouth. He slid in and out of her mouth a half dozen times, urgently, but not roughly, summoning his willpower to keep from ramming himself down her throat. He felt his ardor rising swiftly and he pulled out of her mouth, panting heavily.
He let her wait as he gained some semblance of control. He decided to improvise, kneeling down in front of her and unbuttoning the front of her blouse. She shot a questioning glance at Miss Delaware as he pushed open the shirt, exposing her breasts.
“Eyes on him!” the librarian snapped. Cassie flushed and faced Jack.
He pushed her shirt back over her shoulders until it caught on the bindings of her wrists. With a deft motion he undid the clasp at the front of her bra, letting her magnificent breasts out of their silk prison.
“Fuck me with your tits,” he demanded hoarsely.
As she had the two nights previous she enveloped his member in that wonderful softness and began to slide up and down.
“Yes, just like that,” he whispered. She continued as instructed and he felt his pleasure building again. He knotted his hands in her hair again and bent her head forward, so her chin was tucked to her chest. As the tip of his penis emerged from between her breasts it went straight into her mouth. He moaned at the sudden return to heat and wetness. She dropped back down, and out he popped, his cock disappearing back in between her tits. Up and down, in and out, his cock started to thrum as his desire rose to a fever pitch. He gripped her hair tighter, pushing more urgently, ever deeper. Cassie began to moan in time to him, obviously nearly as turned on as he was. The knowledge that she was enjoying this shattered the last of his resolve. He cried out and thrust himself as far into Cassie’s mouth as he could, cum shooting out of him like a geyser. She sucked him eagerly, greedily, her lips wrapped like a second skin around his pulsing cock.
Finally his load was spent, and his legs almost buckled as he stepped back, gingerly releasing his grip on Cassie’s hair as he pulled himself from her mouth. He was flushed and his heart was pounding as though he’d just run a mile flat out. He gazed down at the goddess still on her knees before him, still bound and disheveled, her eyes on the floor, still playing the role of submissive. He hastily rearranged himself, pulling up his jeans and zipping up before turning his attention to Cassie.
He reached out and gently re-clasped her bra, then pulled her shirt back over her shoulders and re-fastened the buttons. He reached behind her and tenderly unwound the tie knotted around her wrists. Grabbing hold of her hands he helped her get to her feet. She continued to stare meekly at the ground, so he tucked a finger under her chin and forced her to meet his gaze. A riot of emotions warred across her face – wonder, trepidation, confusion, fear and unmistakable desire all trying to lay claim to her. He smiled at her and she smiled back.
“How was I?” she asked timidly.
He shook his head in wonder, words failing him. As he looked down at her he became aware of the strength of his feelings for her. He’d always carried a flame for her, but the events of the last few nights had stoked those feelings to a bonfire. He felt a crushing dread that it was all over now. He wanted desperately to kiss her right then, but fear of rejection, incredibly ironic considering what they had just experienced, kept him from bending his lips to hers. He just about pushed away from her, but decided he had to know one way or the other.
“Fuck it,” he growled. He wrapped his arms around her and kissed her with every ounce of passion in him. She stiffened for a second and then melted into his arms, hungrily reciprocating.
“Finally!” Miss Delaware exclaimed, breaking the spell.
Jack reluctantly broke the kiss. He turned to face the librarian. Cassie’s right hand slipped into his left and he felt himself grinning foolishly. Miss Delaware was watching both of them with a devilish amusement twinkling in her eyes.
“I was wondering how long it would take the two of you to figure that out,” she said, rolling her eyes at them.
Jack and Cassie both stared at her, confusion writ large upon their faces.
“Oh, come on, it was pretty obvious what was going on from the very beginning. There I am, looking stunning and doing my best to seduce young Jack here, and you come sashaying in and next thing I know I’m all but forgotten.”
“She was upset. She’s my friend. I couldn’t just ignore her.” Jack protested.
Miss Delaware snorted. “All I needed was one look at you with Cassie and I could see how smitten you were with her. This lonely librarian never stood a chance,” she pouted.
Jack started to protest again, but she held up her hand. “Don’t, Jack. You may have been fooling yourself and repressing those feelings out of respect for a friend, but they were definitely there. And once I saw the trust Cassie had in you, sharing those intimate details with you, the inner Cupid in me took over and here we are.”
“Wait a minute,” Cassie said. “Are you saying that all this,” she made a lewd gesture with her hand and her mouth, miming a blowjob, “was your way of setting us up?”
Miss Delaware grinned mischievously. “You couldn’t have given me a more perfect opening, with that sob story of yours. Let’s just say it inspired the romantic in me. And,” she said, eyes dancing wickedly, “I got to have a little fun myself.”
Jack just stared back at the librarian, astounded at the sheer audacity of her plan. Even more amazed that it had worked. Cassie, however, was regarding Miss Delaware with unveiled hostility.
“Kind of taking liberties, weren’t you?” she accused. “Sucking Jack’s dick when your master plan was to have us wind up together?”
Miss Delaware sighed and rolled her eyes. “It worked, didn’t it? Yes, I may have been… enthusiastic in my role as teacher, but I knew you never would have released your inhibitions if you hadn’t seen me do it first.”
Cassie glared back, but her shoulders eventually slumped in defeat. “I guess,” she muttered.
“And Jack, would you have truly let Cassie, your good friend, do what she did if I hadn’t already stoked your lust so you were no longer thinking straight?”
He shook his head, smiling ruefully. “Probably not,” he admitted.
She rubbed her hands together in satisfaction. “Well then, my work here is done. Besides, now when someone asks you how the two of you got together you are going to have one whopper of a story to tell. No one is going to top this one!”
Jack laughed, “That’s true. I can’t wait to see the look of my buddies’ faces.” He winced as Cassie punched him hard in the shoulder.
“Ow! What the heck?“
“You aren’t telling anybody about this, ever!” Cassie told him.
He gave her a mournful look. “Come on. You know how Drew is always bragging about his sexual conquests. This would shut him up!”
Cassie rolled her eyes and put her fists on her hips. “Jack…” she warned.
He raised his hands in mock surrender, laughing at her expression. “Alright, I give up! It’ll stay our secret. I’m zipping my lip,” he said, miming twisting a key in front of his mouth and throwing it over his shoulder.
Her expression thawed. “Wise decision,” she murmured. “Besides, you’re going to have even better stories to tell in days ahead,” she told him, her expression positively naughty.
He gulped. “Better stories?”
She nodded, stepping into him. She reached down between his legs and stroked him. “For three nights I’ve had this big cock of yours in my mouth. Now I want to feel it inside of me,” she purred.
Blood rushed from his brain to his cock in the blink of an eye, and with a grunt of primal lust he scooped Cassie up and threw her over his shoulder, marching towards the library doors. Miss Delaware stepped to one side, letting her star pupils pass, a mixture of amusement and envy on her face.
“Jack, what are you doing?” Cassie giggled.
“What I should have done a long time ago,” he growled. “I’m taking you to bed.”
Source: reddit.com/r/eroticliterature/comments/eq3v2v/cassies_oral_education_part_two_oral_ffm