lesbian sex

Massaging the Teacher

A young man massages his older crush.

Spankmasters
May 2, 2024
15 min read
massageMassaging the Teacherteacher
Massaging the Teacher
Massaging the Teacher

Massaging the Teacher

Vince had been fortunate after graduating from high school three years ago. College hadn't been the right fit for him, so after two semesters, he left. But it was challenging to find a decent job, especially when you lacked experience and wanted to live in an apartment and own a car. He instinctively knew that college wasn't for him, but he had to discover something that would allow him to afford rent and groceries.

Fortunately, a friend suggested massage therapy because he was strong, understood sports injuries, loved to work with his hands, and assisted people. It didn't take long to obtain a degree and license in this field. So he enrolled in school, spent the next year there, and then became a licensed massage therapist.

Vince got his first real break at a job working as a massage therapist at a local parlor on the other side of town. It was a small place that only had three therapists and a few support staff. His pay was good, and with tips, he'd be making quite a bit of money. It also didn't hurt to flirt a bit, just like the women did, which would result in larger tips.

He struck gold in this career. He was earning a reasonable income, feeling optimistic, and had a girlfriend after several years of being single.

Then one day, she walked in... Professor Carrington... his high school mathematics teacher. She was a stunning woman he'd had a huge crush on. Every time she stood in front of the class in her blouse, skirt, and heels, she captivated the room. He knew every male student had erections during those lectures, and he certainly was one of them. For weeks, he fantasized about her and masturbated, picturing all kinds of provocative acts happening in the classroom after everyone had gone.

She was a few years older now, and he hadn't seen her since his first semester in the college, but she was still as gorgeous as ever. She matched her signature style, even coming to the massage parlor wearing this attire.

"Vince!" she exclaimed with a bright smile, approaching him and giving him a warm embrace. "It's been ages since we crossed paths."

He was stunned by the sensation of her warm, soft body pressed against his. He'd never hugged her before, nor had he shaken her hand. She had heated his body with her closeness, causing an instant erection. All his past fantasies flooded his mind, making him eager.

"Uh... it's great to see you again," he responded, reluctantly letting go of her. She held his shoulders with her hands, scrutinizing his physique.

"You've evolved into a very beautiful man," she complimented him. He found it unusual to receive this type of compliment from someone he had crushed on for so long. "You were a hunk even back then."

He turned red, stunned by the compliment. It's not often that your crush confesses their admiration for you. "Thank you."

"Trust me, you're looking pretty buff," she said, moving her hands down to his upper arms to feel his muscles. "You must still exercise a lot. You were already big even when I first met you."

He was taken aback that she had noticed him. In high school, he was quite shy and did his best to avoid attention. But her hand on his arm brought his thoughts back to school. "Yes... I've always loved working out."

"Anyway, what brings you here today?" She indicated the place where her left thigh met her body, very close to her... um... "I believe I pulled something in my thigh or hip while running."

"Okay," he responded. He intended to remain professional in this situation. "I'll examine that and see what I can do."

She smiled. "Well, there's a confession I'd like to make. My husband and I actually own this massage salon."

"What?!" Vince was incredulous. She'd undoubtedly remembered him since high school. "I had no notion."

"And I wanted to make sure you were paid well. So when I saw your job application, it didn't take much for us to pick you," she confessed, grinning.

"Wow!" he gasped. "Thanks for the consideration."

She smiled back. "You can repay me by giving me a good rub."

"Absolutely," he smiled back, noting the pleasurable time they shared. "I'll simply step out..."

"Don't you usually go without a shirt? I've heard you don't wear one," she mentioned.

"Uh?" Vince questioned, confused about how she knew.

"Oh... people talk. Why don't you go ahead and take it off?"

Vince looked at her, a tad unsure. "My shirt?"

"Yeah, just do it."

Vince removed his t-shirt, feeling a bit awkward. Her expression of longing and lust ON her face was clear.

"You look fantastic," she praised, her fingers lightly touching his chest and abs. They ignited his arousal.

He stepped back, a little uncertain. "I'll... I'll go... uh... out and... uh... let you get undressed, okay?"

"No need to go. In fact... why don't you assist me?" She faced him and waited.

Vince wavered, torn between fear and lust. This was a step too far. Would his fantasies match up to reality, or would it ruin them all? And worried he'd be fired if he didn't comply with her demands.

"Sure," he said hesitantly, his hands partially raised.

"No need to speak," she said softly. "I won't rat you out." She giggled teasingly.

He froze, his arms still raised as if to help her. His boss... his crush was asking him to undress her...

"Okay... I'll do it quietly," he murmured. His hands went to her blouse and pushed the buttons undone. She helped take it from her and laid it down. Then she turned around for him to unfasten her bra.

Vince choked down a breath. Would he ever see her nude? His childhood crush was now just in front of him. Was this anxiety or excitement? Her breasts, revealed under her blouse, were too good to be true...

"Just zip me, would you?" she asked, positioning her shoulders to make it easier for him.

He hesitated. His brain blanked out due to both excitement and fear.

"No problem," he stated, unzipping her leather skirt. His fingers trailed across the back for a peek. The hips of her pants were visible, and hints of her black panties could be seen beneath. When the zipper reached its end, she spun around playfully.

"Get my skirts off, would you?" she smirked, waiting patiently.

Vince wasn't prepared for this. He just wanted to take a peek at her chest. Imagine touching her breasts...

"Sure," he breathed involuntarily. She instructed him to pull the zipper down, and his hands automatically found her skirt. He slowly slid the zipper down, watching the flash of her black panties. When the zipper was all the way down, she turned around.

"Help me off with this, please," she asked softly.

Vince choked down a sigh. She had kicked off her leather skirt but remained just in her panties.

"Here you go," she asked, indicating her panties.

He went to her and helped her pull them off, his eyes on her legs the whole time. As she stepped out of them, she tossed them away with the other clothing.

"May I...?" she asked, gesturing to his head.

Vince's eyes widened in shock. She was taking off her panties. His heart raced like crazy.

"Yeah, our last piece of clothing," she added, giving him no time to deny. She pulled herself upright, her hands on his head, guiding him towards her.

"You're my boss... and my crush," he muttered stiffly. "I'm a little... scared."

She giggled. "Let's just get you up, shall we? And then they're all off." And she stood up, allowing him to feel her nude.

"Let me turn around," he said, almost inaudibly. He couldn't handle staring at her.

"Of course," she agreed, facing him. Vince began to support her as she slowly turned around, never ceasing to look at her bare legs. She lay down on the table, her legs spread wide, showing her glistening pussy.

"Is this okay for you?" she asked, sensing his confusion.

Vince swallowed those words. He couldn’t believe it... there she was, naked, possibly the hottest woman he'd ever seen. He just stood there, trying to stabilize himself so she didn't fall. "Um..."

"Help me off with my... bra," she whispered.

Vince went to her and carefully unclasped it. His eyes refused to leave her tits and nipples. When he had it off, he set it carefully on the table.

"You have a many virile fans of your superior body," she joked. She laughed as he found himself standing there, staring at her look of desire.

"Are you still game for a massage?" she asked, lifting her head.

Now overwhelmed with lust, he simply nodded and rushed to her, kneeling next to her so he could grab some oil. "I'm sorry... I'm not... I'm..."

"Don't worry," she interrupted. "You're good to me. It's okay."

"Dang!" he muttered silently as he sensed his throbbing cock could barely hold his weight. If nothing else, he knew it would create a huge tent in his T-shirt. Vince took a deep breath, trying to maintain his balance, before he rose. He could feel his rock-hard penis pressing against the fabric of his pants.

He wandered over to the head of the table, drizzled some warm oil onto his hands, and began to massage her upper back and shoulders. She murmured softly beneath his touch, but otherwise remained calm and relaxed. A few minutes into the massage, she started engaging him in conversation.

"So... Vince, what did the guys at school gossip about when it came to me?" she inquired.

Vince's mind flashed back to the countless casual conversations he had with his friends about her outside of class. They all held secret desires for her. And they all confided in each other about their inside thoughts.

"Well, not much, um... we all found you very... attractive," Vince stated, bravely attempting to remain politically correct.

"Mm... be a good boy and dish the truth, Vince. I'd really like to know."

Vince coughed for a bit, unsure of how to proceed. He carried on with massaging her large muscles.

"Um... I guess it's fair to say we all had a crush on you."

"Yes? That's sweet. Now, while I'm sharing, I'd like to let you know that I dressed specifically for that reason. I wanted to elicit the attention of people like you. Especially you. And I... I thought it was fun."

"We sure did appreciate your outfits," Vince managed to squeak out. He inched closer to her lovely ass, careful not to cause any accidental stimulation.

"Did you enjoy them?" she asked.

"Uh... yes... obviously."

His hands were trembling as he moved up her legs toward her feet, intending to finish the massage.

"Mmm... your hands feel so satisfying," she murmured sexily. "You are very strong, hmmm. Were you more of a cleavage man or a skirt man? Which bit of my body turned you on?" she teased, taking his mind off their inappropriate discussions.

His hands were shaking profusely. She knew his buttons; she had her way with him. He couldn't help but speculate if he should reveal his exact fantasies about her. He just didn't envision confiding in someone so much older. But how does one address their perverse thoughts to a crush?

"Honestly, it's difficult to say. I like both," he answered.

"Perhaps I could've let you know when I didn't wear any underwear during class and observe how you would react. Maybe I could've revealed just how aroused I could make you in the bathroom."

His mind nearly exploded with the mere suggestion.

"I'm afraid the repercussions would have been... significant," he lied, trying to sound calm.

She laughed it off before turning away and resuming her reclined position. "I like that. It indicates you're trying to live up to the reputation you have with your friends," she purred.

Vince continued massaging her feet, then moved onto her calves, and then to the backs of her thighs. She spread her legs, which offered the best view of her pussy. Vince let his fingers graze her soaked pussy and watched as her body quivered. Her swollen clitoris begged for attention and his eyes enjoyed the sight. He'd never thought about that side of her body before.

Vince maneuvered his erection for a more comfortable position and adjusted himself.

"Do you feel discomfort on the upper part of your thigh, some on the inside, and some on the front?" she asked gently.

"No... it's more of a problem with the location of your questions," he joked, attempting to lighten the mood.

She laughed as she responded, "I'm glad you see it that way. That feels much better."

Vince resumed his massage, moving to her crotch. His mind almost malfunctioned as he struggled to keep his arousal from overtaking him. His thumbs and fingers deepened their contact between her thighs, while his middle fingers curved around her cheek and probed her incredibly sensitive perineum.

"Mmmm... that is indeed better. I can't imagine a more relaxing experience," she said, transported to a different place by the sensations.

He shifted to the side of the table for a better view of her thighs, noticing her muscles tighten and relax repeatedly. His thumbs brushed against her... fingers... that lay between her thighs. She was pleasuring herself while lying down! This revelation stunned him, so much so that he stopped massaging.

"Is there a problem?" she complained, sitting up on her elbows and turning towards him. Her cleavage came into view, her unyielding nipples grazing the tabletop.

"I'm not sure I can continue, Ms. Carrington," he stammered, taking a step back.

She maneuvered to sit on the edge of the table, revealing her complete nudity to him. Her frame was stunning, her breasts even more enticing than he had imagined, and her nipples, erect and sharp. Her pussy was bare, and her arousal was evident by her swollen labia. She was captivating!

"Do you recall a conversation we had earlier about your husband and I being the owners of this establishment, wouldn't you?" she posed, slipping a finger across his chest and lightly tweaking his nipple. "Would you rather quit this job and find no work in this town, or provide me with the massage I desire, making a substantial amount of money?" She traced her finger towards his increasingly tumescent cock as she spoke, her eyes locked on it.

Vince's mouth felt desert-dry, and he licked his lips. He was losing blood to his throbbing member and could not think clearly.

"I understand that," she said, smiling, positioning herself atop the table. "Shall we resume the massage?"

Vince's chest felt tight as he watched her stretch out on the table, her posture so professional and like a star in an adult film. He returned to her shoulders and neck, rubbed them slowly, and moved his hands to cover her breasts. He could feel her nipples hardening under his palms, pulling them, squeezing them. Her thrill increased his arousal.

"So satisfying," she moaned. "That's correct... so satisfying."

He grasped one breast with both hands, caressing both of them. She permitted him to stay there for a moment. With his fingers wrapping her breasts, he gently pushed them farther out, exposing her erect nipples. He could feel them against his palms. He pinched them lightly, fulfilling her delight.

"Mmmmm," she murmured. "Just perfect. It feels amazing."

He held one breast in both hands, applying pressure, pulling, and caressing it. His cock was pulsing and aching.

" massage here," she stated, taking his hand and guiding it down her stomach. "The massage," she corrected herself, manipulating his hand and placing it between her legs. Lifting her knees, she displayed her pussy for his exploration. Unmistakably, her miniature cry was a sign of her desire. He pushed his fingers into her, teasing her clit in the process.

"Please, keep that up."

Reluctantly, he removed his fingers from her pussy, but she stopped him. "Hold on a minute; we can end your employment right now. Alternatively, you can comply with my request."

Vince had zero intention of quit, and even the thought of fulfilling his fantasies appealed to him. His mind raced with thoughts of her bodily fluids coating his fingers as he nominally navigated her, pushing his fingers deeper within her.

Her response was prompt, "Good choice."

Her voice trailed off as she drew his hand from her pussy, dragging him further down her body, presenting his erection with her face. Her lips gently brushed his shaft, causing it to grind against her forehead. He then felt her returns lips find the back of his thick head while she kissed her way up the shaft, gazing into his eyes as she circled it with her mouth.

"Mmmm.... such a terrific cock," she murmured.

As a result of this change in direction, he had to bend forward enough for his cock to gently brush the top of her head. She noticed right away, and instinctively moved her head to bob up and down against his member, teasing him with her lips. Simultaneously, he continued to pleasure her as he inserted a finger into her again, feeling her excitement and anticipation rise. Her hands were occupied undoing his work pants and boxers as she teased his shaft. Seconds later, his pants and underwear pooled at his feet, exposing his cock, which she immediately caressed with her tongue.

"Such a provocative cock," she uttered, before sliding back to the head of the table. Measuring his member with his hands, she eased his penis into her mouth. At first she went at it gently, rotating her tongue around the head. But her excitement only began to grow, and unbeknownst to him, his head began pushing against the back of her throat, eliciting loud inhales that augmented his arousal. He unable to resist the sensations.

"That's right....." she moaned, bobbing up and down as he eagerly fucked her mouth. Her tongue swirled about his glans with each thrust.

Vince slid his hand into her crotch, teasing her clit and then diving deep while spanking her clitoris with his palm as he fingered her, forcefully and vigorously. He continuously alternated between these actions, causing her desire to escalate. It didn't take long before her mouth expelled his cock and a loud moan slipped out, her body trembling and her pussy squirting.

Breathing heavily, she rose and approached him, holding his cock in her hand while she slowly stroked it. "Wow, you're a magnificent stone! I'm going to become a regular patron, along with my friends. You like that concept?"

"Yeah," he nodded slowly, still uncertain. But the prospect of making a fortune by fucking intrigued him. He would be admired. He would be desired.

"You'll make a tremendous fortune," she said, turning and pulling him toward her. She raised her leg onto the table, exposing herself wide and inviting him in. "Fuck me!" she commanded. "I need your hard dick in my vagina, right away, straight away!"

He moved toward her, his erection ready for her. As he came closer, his shaft slid off target and began penetrating her ass instead of her vagina. With all the oil, everything was slippery.

"Damn it," she moaned. When he tried to move back and adjust his position, she objected and held him in place. "No, not at all! This is even better! Fuck my ass! You're such a twisted individual. I'm deeply into anal play!" She moved herself around, probing and prying, attempting to sit him on her asshole. It wasn't as easy as her vagina, but he eventually pushed deeper and deeper. When the head broke through, there was only the decision of how far he wanted to penetrate.

Her body was jerking, she was so turned on. "Fuck me!" she cried out. "Fuck my ass!" She lowered a hand down to her genitals and was obviously stimulating herself in the process. Vince felt her grasp his member and his testicles occasionally as he gradually forced his way deeper within her. Then she grabbed her hips firmly and commenced thrusting in and out.

She was taut, yet it felt exquisite. She continued the low-toned moaning... not the high-pitched moans he'd prepared for... but a deep wail from deep within her spirit. She was genuinely reveling in this experience. And she was going to orgasm intensely.

Within a minute, she climaxed... making audible moans and squeals. She even spewed her fluids over his legs. As he took himself from her, she hastily reached out to keep him from leaving too fast, since her body was still incredibly sensitive from the exertion.

"Go slow... slow..." she moaned and then let out a piercing shriek as his cock finally emerged. "My God... that was remarkable," she whispered, trying to catch her breath.

She turned and threw her arms around him and kissed him. He had to hold her up, so she wouldn't fall, since her entire being was so drained.

"Yes, that was exceptional," she whispered again, still burying her face in his chest. Vince felt her supple skin against him, so delicate, her nipples so hard in comparison. And his cock was still hard, rubbing against her hip. "Hmm... you're still firm," she said while removing her arm from his erection and running her fingers along it. "But you can take care of that, right?" she giggled, moving her hand up and down a couple of times before relinquishing it. "I could help next time."

His erection was still throbbing and he had an urgent need to discharge. "Arg!" he grunted.

She kissed his cheek and started getting dressed once more. When she was finished, she was observing herself in the mirror, adjusting her hair and make-up.

"Make certain the room is spotless and ready for your next customer, is that right? It might be best if you take care of that once she's finished."

Vince retrieved his pants and contemplated if his erection would soften at all for his next massage assignment. "Yes, ma'am." He trousers were heavily bulging in the front. He would undoubtedly need to attend to his hard-on.

An expenses week had passed when he was informed that one of Professor Carrington's special friends was coming. She failed to divulge her name or the origin of her visit... he would have to determine this independently. He had just completed cleaning the room, when a woman in her late 50s was summoned.

"Hello Ms. Dietrich, my name is Vince and I'll be performing your massage today." He guided her to the room and shut the door. She strode toward the chair and set her purse down, then changed direction to face him. "What form of massage are you seeking today? Are you in any pain?" Vince inquired, going through his usual routine.

She grinned and headed in his direction, closing the gap until she was uncomfortably near. She couldn't quite reach the snug t-shirt he had on, but she placed her hand on his chest. "I've been informed you usually don't wear a shirt," she laughed, and then moistened her lips.

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