Diane's Inamorato Tutee

Charlie was breathing heavily from a combination of excitement and embarrassment. He shouldn't have a raging boner when this lady was trying to help him. He felt like a perv. She'd almost caught him looking at her ass earlier. Now, she had caught him with a hard-on. He waited for the scolding, but as she continued on with the massage, he was relieved she didn't seem to realize what had happened.

In fact, Diane did proceed as if nothing had happened, first to his other leg, then to his arms. When she finished, she re-covered him completely with the top sheet. She finished with a scalp massage, stroking and petting his head. Charlie was in heaven. His eyes were closed. His cock was still swollen, just not painfully hard. He'd almost drifted off.

"How ya doin' there, Chaahlie?"

He could barely answer. "Ah ... uh ... very nice, thanks so much Diane."

Then suddenly he perked up, "Are we about done?"

Diane stiffened. "No. Would you like to be done?"

His mind screamed "YES!!! Get us out of here," but what exited his mouth was "uhh...." as he tensed in the bed, hastened back to his teen reality of ego battling id, of hormones, of nerves, of insecurities, and this friend of his mom who might discover his uncontrollable, re-hardening member.

Diane felt his body go from very relaxed to instantly tense.

"Poor kid. He's wound like a spring. It just not .... healthy." she thought.

Maybe it was the wine. Maybe it was several conversations about Charlie she had during sessions with Cindy Simpson. But as she worked on him, Diane had shifted from feeling sorry for him, to being concerned.

"So Mr. Simpson, no answer? I'm a bit put off." She mocked aggravation. "Are we done? Really? We're only 20 minutes in. What in the world do you have better to do right now?"

Charlie once again was tongue tied. "Uhm I ... Uh ..." he turned his head toward her, and was relieved to see a beautiful grin. He sighed in relief.

"Oh I'm just teasing," she patted his arm. "At least about the "put off" part."

She adjusted his head facing back down, and rubbed his shoulders as she softly spoke. ".... So let's think about this ... You'd leave here. Then you'd realize your Mom paid for a full session ... with quite a nice tip by the way .... and what then? You'd drive around for 40 minutes, so she wouldn't know you scooted out early? .... instead of just getting a great massage? ..... that would be silly, don't ya think?"

"Yeah," he chuckled.

... and she was exactly right. That probably is just what would have happened.

"Then your Mom would come in for her next session, I'd have to refund her for your unused time, and she'd find out you shot out of here early anyway. That would be a mess .... So many worries ... so little time, yeah Chaahlie?".

After groaning in acknowledgement, he chuckled again.

"So what are your plans for next year?" She could feel his shoulders relaxing again.

"I'll be at Georgia Tech, I start in September".

It was something Diane already knew. She also knew he was very pleased about it. In fact, she knew a great deal about Charlie from conversations with Cindy Simpson during her sessions. She was keenly aware of Cindy's concerns about Charlie's social life. Diane had just blown them off as overstatements, or helicopter parenting. But they clearly weren't.

"Oooooh, Georgia Tech eh? You must have quite the brain to get in there."

"Uhm.. yeah ... I guess."

"A brain like that, attached to a body like this ..." she tapped his head and then his back "... you'll be knockin' 'em dead in college."

As soon as "girls" re-entered the equation, his demeanor changed.

He huffed a sigh of frustration as he thought to himself, "She doesn't understand how spastic I am. She doesn't understand what being a "geek" in high school was like. ... She doesn't understand anything."

Diane registered his sigh, and changed the subject, "Well, in answer to your earlier question, no Chaahlie, we're not done yet. Okay?"

"Okay," he answered, glad the conversation took a turn.

"How's your back feel?"

"Really good." He nodded in the head rest.

She patted his head, then turned away as if paused in thought. "So? ..."

After a moment, Charlie raised his head quizzically at the open question. As he looked toward her as she knew he would, he was again treated to another vision of Diane's gorgeous rear two feet away.

"... does this beat driving around and wasting time?"

"Uh ... yeah" he answered, and while his voice wavered, his cock didn't. It extended almost painfully downward. No panties! There couldn't be! He suspected even a thong would show, and he saw no evidence of one as he studied every detail visible.

He had enjoyed quite a nice look before he finally caught her reflection grinning at him in the mirror. Before he had time to react she quickly turned to him. His face blushed crimson. Feigning confusion, she said "Oh? You were wondering about that?" She pointed to a large device against the wall under the mirror. "It's a tanning bed, Chaahlie. Some of my clients use it. But mainly me. So ... you know ... no tan lines to muss over." She shrugged. His cock didn't. It went rock hard.

As she left him to process the idea that she often laid right there naked, she strolled around the table, smoothing the sheet over him as she moved. She smoothed it, stroking over his back, over his legs, stroking his body. At the base of the table, she reached under the cover and spread his feet to its edges. She adjusted the sheet, carefully pressing it to the bed between his legs until the outline of a very impressive cock was discernible beneath. Charlie knew her hands were dangerously close. With each pass, he squinched his eyes shut, and clinched his jaw at the thought of being discovered. Almost immediately a tiny wet spot appeared at its tip on the sheet.

She lifted the bucket of stones onto the bed and plopped it between his knees. "So Chaahlie, these are smooth heated cobblestones. They are quite healing, and sort of set the massage in." She rubbed oil on the first one.

"I'm going to place them under the sheet, just like this." She reached under the sheet and stroked his back with the first stone. Then left it in place at the base of his neck.

"How's that feel, Chaahlie?"

"Mmmmm"

Not too warm?

"Ugh uh, no"

She continued stroking his back and placing stones under the sheet about six inches apart along his spine. "Good. We have to do several of these. But they'll be delicately balanced on your body. Try to remain very still. They're kind of expensive, I'd prefer none of them slip off and hit the floor. Okay?"

"Uh OK"

"This final one goes just at the tip of your tailbone." Her eyes twinkled. Her tongue ran across her upper lip as she applied extra oil to the stone. She slid it over his tailbone, but then eased it further until it was midway down his crack. Warm oil dripped between his buttocks. Charlie gasped and started to flinch, but controlled the response.

His hands resting under the sheet, palms up, each received a stone of their own, as did the area behind his knees. By now the wet spot at the tip of Charlie's cock was the size of a 50¢ piece. The area was transparent to the point Diane could see the boy was circumcised.

She smoothed the sheet over his thighs, and when she again brushed near his cock, he tensed, as she knew he would. It was just enough to send the precarious gluteal stone sliding down his ass to rest on the bed beside his scrotum. Charlie's eyes sprung wide open. With his head remaining in the cradle lest he dislodge another stone, he tried to speak, but Diane interrupted.

"Chaahlie, what are ya doin'? You have to be still ......" Diane was grinning but tried to sound stern.

"Sorry..... I'm sorry..... It just slipped down."

"Oh I saw it slip, Buster, and I can't leave it where it landed because it can cause burns. Now don't you dare move an inch. Clear?'

"Clear," Charlie agreed.

I'm just going to reach ... ah ... yes ..." Diane slipped her fingers under the sheet as if searching between his legs.

Charlie gasped.

"Hold still!" she commanded as she began to fondle his erogenous perineum. She squeezed it between her fingers and thumb as if mistaking the spongy area between his ass and scrotum for her missing stone, as if trying to get a grip. "Ah is that it?" She asked as if speaking to herself.

Charlie's legs went stiff. His cock went stiffer. He started to pant.

With each squeeze, she pushed more blood into his obscenely engorged prick, and more semen out of its tip.

"Uh ... Ahh ... Uh" Charlie began to squirm.

"Ah, I'm having trouble finding it, Chaahlie. Sorry. Just a minute more I'm sure. Are you okay?"

"Oooooh, yes. I'mmm ookay." He was starting to involuntarily squirm.

"Ah, there it is. I found it." She retrieved the stone from the base of his cock, and replaced it on his tailbone.

Charlie was panting as if he'd just run wind-sprints. The puddle between his legs was so large she wasn't sure he hadn't cum. She'd find out soon enough though. "Alright Chaahlie, we'll give those about 5 minutes to do their thing. I'll be back." And with that, the Aussy blonde slipped from the room, and shut the door.

On the table, Charlie was desperate. Diane's perineal massage left him on edge. "She had to have known what she was doing, didn't she?" he wondered. "That couldn't have been innocent, could it?" His butt began to quiver as he gently humped the table in the aftermath, but he couldn't move enough to get himself off without dislodging the stones.

Outside the room, Diane fanned herself, poured her third glass of wine, downed it, then retreated to her bathroom for privacy and closed the door. Leaning back against the sink, she contemplated. Was she going to do this? Was she sure? She knew her project in the massage room would commit to anything at this stage. She had never crossed an ethical boundary in a massage session before. But she also knew this kid had a lot to offer if he could get past just some of his disabling insecurities.

She picked up her phone and dialed.

"Cindy? Hey, it's Diane. Listen, when Chaahlie arrived tonight, his back was really bad. I guess you know that. Anyway, he needs a bit of work yet. No extra charges. No worries. I'd like to go overtime to see if I can at least take care of his biggest issues. Just didn't want you to be wondering where he was."

Cindy thanked her profusely.

As she did, Diane had already eased her hand down the front of her pants. She was wet. She was tempted to finish herself there in the bathroom. Instead, she peeled her outfit off, went to her clothes cabinet adjacent to the sink, and retrieved a pair of thin white linen shorts she used to cover her bottom during her yoga classes. She matched it with a loose fitting white crop top t-shirt which hung straight down from her nipples ending around her belly button.

Charlie had not settled down. He was quietly moaning when Diane opened the door. He wanted to glance over at her, but he didn't dare lest he dislodge her precious stones.

Diane strolled to the massage table. As she began removing the stones, she made small talk. "Sorry it took a minute. I called your mom. I told her we were running a bit behind."

Charlie's brow furrowed. They weren't running behind.

With all the stones gathered, she added, "It gets hot handling these stones, so I changed to something more breezy."

The comment didn't register with him.

"Were the stones good?"

"Uhm, yeah," Charlie's voice cracked.

She pulled the head support off the bed, and had him scoot down. He lifted his midriff up allowing his cock to spring forward with such force it slapped his belly.

"Right. Okay Mr. Simpson over with you. On your back."

Diane held the sheet up blocking her view (and also blocking his view of her), providing an illusion of privacy for him even as he laid there, prone and stark naked. But he didn't budge.

"Uhm, I ... but ... uh ... Diane?..."

"No buts, Chaahlie. On your back right now. We haven't got all night." She shot a look at his face over the top of the sheet. "Do I need to help you, or can you flip over on your own?"

Charlie was as embarrassed as he'd ever been in his life. He was rock hard. There was no way she'd miss that, sheet or not. But he reluctantly complied.

Diane laid the sheet back over him covering his entire body. When the wet spot fell directly on his cock, it was no accident. She smiled. It was a perfect shot. He felt the cool moisture. He knew immediately what it was. After all, he'd felt the same wetness that morning in his boxers. The sheet began adhering to his skin, as wet cloth does. He gasped. He was so screwed!

Diane smoothed the sheet at his hips pulling it taut over his dick. As she did, Charlie nervously glanced down. Not only was the there an obvious mountain under the sheet, he could see his penis right through the wet material. "Oh shit!" he thought to himself. He felt a twinge of nausea. His trembling returned. What would his mom say when Diane told her about her perv son?

But Diane walked to the head of the bed as if nothing had happened. As she did, he finally noticed her change of clothes. Even in dim light the shorts seemed translucent, and .... Nipples!

She was wearing a white, short, loose fitting top .... and her nipples danced in it with each step.

"Holy FUCK!" he thought to himself. But his lips unconsciously mouthed the words, and it was everything Diane could do not to laugh out loud.

At the top of the bed, she leaned over his head, smoothing the sheet on his chest. The bottom hem of her shirt brushed over his face, resting on his chin allowing him a spectacular view of two perfectly shaped D-sized underboobs. Her breasts were naturally upturned, just enough to keep her nips out of his sight. Her skin was satin smooth with a delicate peach fuzz ascending her tummy.

Diane saw his cock bounce. She continued smoothing the sheet, petting his chest. "Enjoying the view Chaahlie?"

He jumped, and she giggled, then so did he.

She moved to his side and smiling gently, she met his eyes with what Charlie realized were the most beautiful blue eyes he'd ever seen.

"So were you? .... enjoying the view?" she asked

He blushed red, and whispered "Yes, the view was great. You're beautiful."

"You wouldn't lie to me now, would you?" she grinned.

"No ma'am"

"So Chaahlie, why do you think you're so nervous around girls?"

"I don't know ... uhm ... yeah .... I don't know."

"Seriously Chaahlie, why is it? .... You're nice looking, smart, and you're packing," she gave a nod to the cock nearly reaching his bellybutton and bobbing beneath the sheet. Without waiting for a reply, she said, "It's a nice one," she smiled.

Charlie's face felt like it was on fire. He was beet red.

"Oh make no mistake, Mr. Charles Simpson, I get it. You may have had some setbacks. But you are way more than capable, I promise you that."

She folded her arms taking a more serious expression, "You know what I think the problem is, Chaahlie? It's not what you're capable of. It's your confidence lagging so far behind what you're capable of. You need more confidence...."

Charlie nodded in agreement.

"... and so where does confidence come from?" she asked.

"Where?" his response was barely audible

"Confidence comes from experience, Chaahlie. Good experience. The more experienced a guy is, the more confident he is with women." She nodded her head. "It comes from experience."

Charlie nodded with her, and when he did, she leaned to his ear and whispered, "Do you have any experience .... Chaahlie?" Her hot breath in his ear was exhilarating.

"Uhm, no, not much," his words barely audible.

Still in his ear, she whispered "Does ... "not much" ... mean "none" .... Chaahlie?"

It was the kind of admission no 18y/o boy wants to make, but he nodded "yes" as his lips began to quiver.

"Perhaps ...." she whispered, as she moved her lips to his and kissed him.

She moved her face back, stroked his chest "....we could change that."

She stepped away again folded her arms, and raised an eyebrow. "You don't kiss and tell, do you Chaahlie?"

He vigorously shook his head "no".

She smiled then gave him another light kiss, "Well then mister, let's get you some confidence."

She strolled to the foot of the table, feeling flushed for the first time from the wine. She slowly slipped the sheet down, but only to his mid-abdomen. "Nice six-pack there Mr. Simpson" as she generously poured oil onto his chest and abs. His cock was rigid, bobbing well above his trembling frame. It lifted the top sheet up like the entrance to a pup tent, but she avoided it for now. Instead, she rubbed oil under the sheet onto his lower abdomen, running her fingers over his pubic hair. His cock levitated above her hand. Charlie's entire body went rigid. His heart raced.

Once she had him well oiled, she climbed onto his abdomen, mounting him cowgirl style. Keeping her eyes locked on his, she slid her pelvis from his midriff all the way to his chest, then back down, then up again, adding more oil, then down. As she repeated the process, the oil soaked her shorts. Using her feet, she slowly edged the sheet down until his cock was fully exposed behind her.

Charlie panted. He thought he felt the top-sheet slipping down, but he wasn't sure. Should he touch her? He wasn't sure. What was going to happen here? He wasn't sure. So, he gripped the mattress pad, white knuckled, nearly hyperventilating.

Diane was starting to tingle. Whether it was the wine, or the knowledge she had the power to give this quivering young man an experience he'd cherish forever, she didn't know. But she did feel her pelvis heating up.

"Chaahlie, do you know what a "one-off" is?" she asked. She felt the tip of his cock bump her just below her waistband as she continued sliding up and down his torso.

He had no clue what she was asking, but he nodded "yes".

"It's a one-time experience. It won't ever happen again. Do you hear me Chaahlie?"

He nodded. Now he got it.

"This is a one-off. Take as much from tonight as you can. There will be no reruns, and there will be no kiss and tell. Not to anyone. Are we clear?"

Charlie nodded again. He was now involuntarily humping, as she rocked back-and-forth while speaking to him.

She lifted up slightly, then shifted back, and as he looked down, the head of his cock appeared between her legs in front. Her oily shorts nuzzled tightly against her, and as she leaned back Charlie could make out nearly ever detail of her shaven folds. She began to slowly, sensually grind on him.

He was writhing. He watched his cock appear, then disappear between her legs. He wanted to put it in her. He could see right through the only barrier between his cock and her pussy. He wanted her naked. She was like a goddess. He needed to fuck her. The voice in his head pleaded with him, "Ask her Charlie! ... Tell her Charlie! ... Tell her you need to fuck her!" His cock reappeared, then disappeared ...

"Gssssch...Charlie's teeth suddenly clinched. Moaning, he began pumping his hips into her. His legs stiffened. He screamed "Ahhggggaawwd-ngh-nghumph".The first spurt hit his chin. "Ummph" His pelvis pumped, and white goo shot onto his neck and upper chest. "Ummph~Ummph~" he pumped a third and fourth shot.

Diane smiled sympathetically, sitting astride him, rubbing his chest, as he regained his senses. For the first time, Charlie released his grip on the mattress pad. Still in a haze, he reached for her reflexively, hugging her and pulling her to him, bringing on a final post-climactic jolt. He continued the tight embrace as his trembling body relaxed.

"Whoa. Sorry, I wish I could have ..."

"Shhhh, shhhh" she whispered, "There will be no wishing what might have been. We have time for those wishes. You just needed to get your first quick pop out of the way so you can enjoy the main course. We are not close to done with you, mister. Now let's get up from here."