Diane's Inamorato Tutee

School was in spring recess, so that Monday was a sleep-in day. Charlie Simpson awoke late in the morning aware of two things. First, he'd soaked the front of his boxers. Second, he had a sharp cramp in his lower back, no doubt the result of humping the bed during his recent wet dream. Grimacing in pain, he rolled out of bed on to his feet. After rubbing the spot and gently maneuvering, the cramp subsided to an ache in his left lower back and upper butt.

He eased the waist band of his shorts over the tip of his rock hard erection, and pushed them down to his thighs where they dropped to the floor. He kicked them under the bed, lest his mom find them before they dried.

Charlie was a late bloomer. Only last year he'd stood 5'8", a skinny, nerdish boy, bespeckled, with braces, and very self-conscious of his lowly rank in the school social pecking order. But over the last year, a growth spurt turned the now 18yr old into a 5'11" 165 pound young man, with barely an ounce of fat. The latter was more attributable to the wonders of youth, rather than any extensive exercise.

He hobbled toward the shower, catching his reflection in the bathroom mirror in route. Pausing momentarily, he admired his physique. Gone were the braces. Everyday glasses had given way to contacts. He'd let his brown hair grow to medium length at his mom's suggestion. His chest and abs, both hairless, gave way to an impressive 8 inch penis, "Little Chuck," now jutting up from brown pubic tufts. It too had gained size over the past year which, unlike the rest of his physique, was probably due to daily workouts ... courtesy of Charlie's right hand, fantasy, and porn. In fact, he would be taking care of it presently, if not for concern of bringing on another lumbar spasm.

The steaming hot shower relaxed his back somewhat, as well as easing his morning wood, to the point that he was able to carefully towel off, take a leak, and pull on some clothes before heading downstairs.

Descending the stairs proved more painful though, and as he groaned one faltering step at a time. His mom appeared at the bottom with a worried expression.

Cindy and Dan Simpson were doting parents. Charles was their only child. They worried and rooted for their child as most parents do. He was a good kid, smart, caring. His shyness was a real concern though, especially with girls. Almost as an excuse to avoid social activities, he buried himself in schoolwork, sometimes far too deeply in Cindy's opinion. But he was driven to become an engineer, and his recent acceptance to Georgia Tech was cause for a huge family celebration.

"Charles, what's the matter?" Cindy asked

"Eh, nothing, mom. I ... maybe I slept wrong. I just got this catch in my back," Charlie responded, rubbing the area.

"Let me see," she demanded as he completed the last stair step. After a brief exam, she added, "I'm setting you up an appointment with Diane."

Diane Dupont was Cindy's longtime massage therapist. She received her certification shortly after arriving in the states from Australia some 20 years ago, and she was very good at what she did. Her husband had died in a terrible automobile accident, a few years before. In the aftermath, Diane seemed to have an absence of interest in kindling new relationships. Instead, she threw herself entirely into her business. What a shame, Cindy thought, because Diane was such a lovely lady.

As Cindy dialed her cell, Charlie interjected, Mom ... mom ... no! I'll be fine. I'm good. Reall ...." His pleading trailed off as Cindy shushed him, and Diane picked up.

"Diane? Hey, this is Cindy Simpson. Listen, I have a favor to ask. My son woke this morning with a terrible backache, and I was wondering if you might have an opening in your schedule for him." There was a pause. "Oh ... you're slammed huh? That's too bad...."

Charlie breathed a sigh of relief. He wanted nothing to do with an experience that screamed embarrassment. He hobbled toward the kitchen when he heard his mom say, "Oh Diane! Would you? I would sooo appreciate it. You have my card, put on $140. Thank you sooo much! I'll get him there at 6. Thanks again."

Then she turned to Charlie with very satisfied smile and said, "You're set for 6 o'clock this evening. She usually sees her last appointment at 5, but she said she'd stay late, and add you at the end. And that's that," she rubbed her hands together in success. "Now let's see what we can get you for breakfast."

Charlie spent the rest of the day in relative trepidation, and as immobile as possible.

...

"Damn!" Her 5 o'clock appointment cancelled. Diane cursed to herself as Jan, her receptionist, passed her the scheduling note. Normally, Jan would have called the next appointment in early, but as Diane had failed to mention the add-on, she thought the 5 o'clock appointment was Diane's last of the day. "Okay, Jan thanks. Why don't you take off. I'll lock up." Her young receptionist thanked her, then skipped out the door. Diane considered calling Cindy to bump her son's appointment up. Then she changed her mind, locked the door, and turned off the open sign.

Dupont Massage and Day Spa was a converted two bedroom cottage in Midtown. The original den now comprised the spa's entry area. There were shelves and tables loaded with an array of spa products for sale, along with a registration desk normally attended by her receptionist. The old dining area now served as a wine and tea room where clients received complementary drinks to relax before or after treatments. A large walk-in shower was available for clients before or after treatments, though it was rarely used.

It had been a long day, and Diane decided to enjoy a glass of wine before Cindy and her son arrived. She'd leave the open bottle for Cindy to enjoy during her son's massage.

The wine, peace, and quiet were relaxing. Her day had been booked solid. She'd had only 10mins to catch a late lunch. All were longtime clients, all straight females. No newbies. No unknowns. No men. So that morning her black yoga pants, sports bra, and slides seemed like perfectly fine attire. Diane worked to stay in shape. She enjoyed highlighting her body as a general fitness message to clients. On days where the clientele composition was different though, especially men, she preferred working in loose fitting scrubs, which though frumpy, tended to minimize any wrong messaging or "erection embarrassment" on "the flip".

Now it occurred she'd have a teenage boy on her table. How old was he? 16? 17? She realized she hadn't asked. She thought about changing her outfit. Not that this one was revealing per se. The sports bra was cupped, and barely showed cleavage, even given the nice set of bouncy D-cup naturals it contained. Her lycra tights were high-rise, calf-length, booty scrunchers. They hugged her figure well, nestling their midseam nicely between her cheeks. They were cute, but revealed any panty lines, which is why she went pantyless when donning them. She did keep several sets of scrubs in the bath closet which she could change in to, but no panties. "So that wouldn't be great either," she thought. "Besides," she realized, she could invite Cindy to the room to chit-chat during her son's session. "That was the ticket! Bring Cindy back. No worries then." She poured herself a second glass, and studied her business inventory printout.

...

Charlie arrived just before 6 o'clock. The spa appeared closed. He knocked softly. No answer. He saw the doorbell, rang it once, and waited about 30 seconds before happily heading back to his car. But the door opened behind him.

"Charles?" A soft accented voice asked.

"Uhm, yeah," Charlie said as he returned to the door. Suddenly very aware of the ravishing form in the doorway. She was about 5'5", blonde, blue-eyed, with a beautiful face, in a skin-tight black two-piece, with a figure that could cause climate change on its own. "Oh shit" Charlie thought to himself.

"Pardon?" Came the soft Australian response.

Apparently the "oh shit" had been utterance as well as thought. "Ugh .... it's Charlie.. uhm .... ma'am," Charlie recovered, as he extended a hand.

Diane shook his hand, then with a puzzled look asked, "Where's Ceendy?"

Charlie was confused "Uhm, she didn't come. Was she supposed to?"

"Well Chaahlie, Yeah, I'm sorry, but yes she was. She was supposed ... She needed to sign your treatment forms. You're not 18 are you?"

"Uhm.. yes ma'am, I am. I'm 18."

"Oh ... well ... I ... I guess we're okay then. Come in. Have a seat. I need you to fill these out."

Diane sat at the table opposite him. With glass of wine in hand, she studied Charlie. She noticed was how stiffly he'd taken his seat, complete with a grimace. It was obviously he was hurting. She also noticed, he was trembling as he filled out the forms

-- Area of pain? - Left lower back

-- Any medical issues? - no

-- Medications? - no

-- Previous massage experiences? - none

-- LMP?

"Uhm, what's this one?" he looked

She smiled at him as he passed the form across the table to her. "He seemed like a very nice boy" she thought. "Well mannered, clean cut ..."

She checked out the form.

"Oh ... LMP? That's Last Menstrual Period. I don't think you'll need worry about that one," she smiled as she slid the paper back to him.

Charlie was mortified. He blushed. He was trembling so much it was hard to write, which was even more embarrassing.

"Chaahlie? Are you alright?" Diane asked in a hypnotically soothing voice.

"Uhm yes ma'am. Uhm, I'm just a little ... uh ... nervous, I guess."

"Why are you nervous, Chaahlie? ... and please don't call me ma'am. Diane is what I prefer."

"Yes maa ... ugh I mean... Diane," Charlie responded.

Diane decided to let Charlie's non-answer ride. "Done with the form? I'll give it a look over while you're getting ready."

"Okay, Mr Charles Simpson, it looks like we're set. Right this way."

She directed him to a 12x15ft room with a massage table readied in the center. She pointed to several wall hooks. "Clothes go there. Then hop on the bed, on your tummy, and cover yourself with the top sheet. I'll give you a minute," and she was gone. The door shut behind her.

Charlie looked around in a daze. The room was dimly lit. Scented candles added to the ambience. Soft instrumental music punctuated with sounds of birds chirping and waterfalls played over a speaker system. He stiffly stripped to his skivvies, and hung his clothes as directed. Then he crawled onto the table under the sheet.

Diane knocked shortly after, and entered. She softly asked "So Chaahlie, you say you've never had a massage?"

"No ma'am" his voice cracked. "I mean Diane."

Diane smiled.

"So you're hurting here?" She asked as she brushed his left lower back through the sheet, immediately feeling the waistband of his boxers. "Sweet kid" she thought to herself.

She let him confirm where he hurt, then said "Chaahlie these won't do" as she popped his waistband through the sheet. "They're right where we'll need to be working. Here's how this goes, except for the body area I'm addressing, you'll stay completely covered all the time. So no worries. Right? We'll start as you are though. Then, in a while, I'll step back out so you can slip those off. Okay?"

Her voice was hypnotic. It enticed agreement. Charlie responded "Okay."

"So .... We're going to do a bit of a release first, Chaahlie."

She bent his right knee, pinned his right shoulder to the bed, then twisted him at the hip, forcing his right knee over the top of his left leg. Charlie's back felt like bubble wrap popping. She repeated the procedure on the left with a similar result.

"Whoa!" was all he could say.

"How does that feel?" she asked, assessing her work.

"Uhm, okay I think," he responded, surprised as he shifted on the bed.

"Get up and walk around," she directed. Immediately recognizing his hesitancy, she smiled and reassured, "You can wrap yourself in the sheet."

Charlie clambered off the table, wrapped like Moses, and began to pace around the table. A slow smile emerged. "Wow, that's like magic! That's unbelievable! How did you do that?"

Diane giggled, and clapped her hands. "We've still got work to do, buster. Now off with those togs" she pointed in the direction of his boxers, "then back up on the table ... under the sheet, mind you."

He just nodded.

As Diane stepped out, she was very pleased with the results of her lumbar adjustment. It was something most therapists didn't know how to do, but when successful, it really was like magic. So now the real work of the session was done. Unless he re-spasmed somehow, the rest would be standard relaxation technique with low back emphasis, toss in some hot stones for good measure.

Then she took a moment to consider her client. "My goodness, so nervous, high strung" she thought. He was so nervous it was contagious. She took on some of his tension. Was this a common thing for him? In general? She shook her head at that thought. If that were the case, it would be terribly debilitating. Casting those considerations aside for the time being, she gathered several hot stones in an insulated bucket, and waited briefly outside the door.

Charlie slipped his underwear off, and eased back onto the table, prone, naked, and feeling more than a little exposed, even under the sheet. Almost immediately, down below, Little Chuck started taking on a life of his own.

Diane knocked, then stepped back in. She placed the bucket on a cart and rolled it near the massage table, then attached a padded doughnut extension to comfortably support her client's head while he was facing down.

"OK Chaahlie, scoot up on the bed with your forehead here," she patted the top of the headpiece.

Charlie complied, but as he slid up on the bed, Little Chuck, now semi-hard, caught in the bottom sheet and popped downward, extending downward like a middle leg. Charlie jumped slightly. But, Diane had already turned to briefly check the stones which she thought were slightly overheated. She was oblivious.

He glanced her direction just to make sure. With her back to him, there at eye level, two feet from his face, was the finest ass he'd ever seen. Her tights highlighted every curve, every crevice, and Charlie suddenly felt like the head of his cock might spontaneously combust.

Diane caught his reflection in a small wall mirror. His eyes wide, his mouth agape, it was more an expression of awe, than of lust. "Well Chaahlie, you're a little more sure of yourself when you think no one's looking, aren't ya now" she thought to herself. With mixed feelings, she gave him just a moment to ogle, before turning back to him.

"Face down, Chaahlie." she directed.

Charlie quickly jerked face down into the headrest. She could she the edges of his face blush. With time he'd learn to be more nonchalant when "caught with a hand in the cookie jar," she thought. His startled response actually left her amused ... or was she amused that she was the cookie jar tempting him? ... maybe it was an element of both? She pondered the question, not quite sure of the answer.

Her sessions all began with the client fully covered by their top-sheet, neck-to-toes. As per her routine, she diligently detailed everything she was doing, before she did it. "Chaahlie, I'm going to touch here." "Okay, Chaahlie. I'm going to press there. Let me know if it hurts." "Let's see how these strap muscles are doing...."

"I'm going to put a little pressure on your lower back just to make sure you don't have one more pop in you."

She climbed onto the table, threw her leg over his back, mounting him, facing his feet. She placed her hands on the sheet covering his upper buttocks, and shoved straight down several times. Charlie's cock felt like it was being driven further down his leg with each shove.

He was focused on that when he realized she was asking a question.

"Uh.. what?"

"I said, any pain, Chaahlie?"

"Uh.. no"

"Good. That'll do." She gave him one more playful jolt, then dismounted.

"Okay Chaahlie, time for some warm oil. I'm going to slip the sheet down to expose your back." As she folded the top sheet down to the top of Charlie's butt, he tensed.

"Chaahlie?"

"Yes, ma'am?"

"Just relax, okay."

"Okay. I'll try. It's just that ... "

"It's just that you've got this strange old ugly lady puttin' her hands on you," she joked as she oiled and rubbed his back.

Charlie laughed

"What's so funny?" she teased.

"You're not old or ugly." The extent of understatement caused him to laugh again.

"Oh, Chaahlie, I don't know," she demurred. "But you do have a great body. Nice muscles. Do you workout?"

"Uh thanks. No, I don't work out much."

"Many girlfriends?"

Charlie laughed, "No."

"Alright Charlie, your back feels pretty relaxed to me. How does it feel to you?"

"Feels great."

"No girlfriends then?" she prodded, genuinely surprised.

"Nah ... not really."

Diane paused her massage briefly. "Are you gay then?"

"Hell no!" immediately shocking himself with his exclamation. He rarely cursed, and never around adults. So as he felt Diane step back, he quickly apologized. "I'm ... I'm really sorry Diane. That slipped out ...I ..."

"No, no ... it's okay ... so ... I mean, it wouldn't be a problem if you were ..."

"Well, I'm not."

She chuckled as she gave his thigh a playful pat. "Time for some leg work."


After informing him of the process, she tugged the sheet back up to re-cover his back, then slipped it off his left leg from the waist down, exposing most of his butt on that side.

"So ... let's see then .... not gay ... no girlfriends ..."

She deftly tucked the residual top sheet under his thigh just above the knee to "lock it down," keeping him well covered, and unaware she'd nearly brushed his cock in the process.

"I ... uh ... I just, I get nervous around girls," he gasped as she tucked the sheet.

"I noticed," she smiled sympathetically, "You're trembling. Just relax."

"Uh sorry. I ... uhm ..."

"It's okay" she patted his back. "Take a deep breath.... Now blow out ... " she had him take several more breaths.

His trembling subsided.

"There, that's better," she complimented, and over the next few minutes she worked oil over his lower leg and foot.

"Does that feel good, Chaahlie?"

"Mmmm, yes."

"Alright, I'm going to do some leg work up top, to make sure that glute is okay. Let me know if anything bothers you," and with that she began work on his thigh and glute. Beginning behind his knee, she slid her elbow up the midline of his oiled thigh and onto his buttock, increasing pressure, rolling her elbow there to treat deeper muscle layers. Charlie drew in a deep breath.

"You okay Chaahlie? Let me know if I'm hurting you."

"Okay."

Diane was working therapeutically, but the thought of a stunning MILF touching his butt brought him back from semi-hard to full-mast and oozing.

She reversed her technique, sliding her elbow down his hamstring to his knee, and again back up to his glute. She repeated the process a few more times. Then, starting at the knee, she proceeded to knead his thigh with both hands. Her thumbs pressed into the lower hamstring at back of his thigh, fingers massaging the inside. Almost immediately, her fingers brushed the tip of his cock in what should have been far enough down his leg to have been a "very safe" area. In fact, it was so far out of place that she wouldn't have been certain what she'd encountered had it not been for Charlie's immediate gasp, and stiffened legs. Her eyes widened, as she mouthed "Holy shit" to herself.

It was her accident. It was not his fault. She considered apologizing. Then she realized downplaying the incident instead would be less embarrassing for him. Nonetheless, this kid was packing some impressive equipment. To her, his insecurities became completely inexplicable at that moment.