Over The Line [Phoebe & Unchained]

Just a little smut role play (still with some plot) about things going over the line during her massage sessions. Things have been going good with her normal massage therapist but when she has to leave the practice for maternity leave, Holly finds herself getting massages from the Apprentice Masseur. She didn't even know they did training when the masseur is under 18. She finds it weird to have a male massage therapist, let along someone underage, but she goes with it, after all, it is nothing but professional, and she will keep her undergarments on, unless he can tempt her to take them off.

Warning: Will have links to pictures in some posts that some will be NSFW​

Name: Holly Winchester
Age: 30
Appearance: NSFW

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[Ignore the dark eyebrows and roots. Holly is a natural blonde, with long wavy hair and green eyes.]

Job: Housewife of a very wealthy business man who is never home and mistreats her when he is.

​

---

"Aw." Holly couldn't help whining into the phone. The spoiled woman was used to having everything go her way because of who her husband was. He was rich and liked to flaunt the fact by getting her everything she needed and then more. It was a loveless marriage. At first, Holly had been smitten by him, but over the years, he started to ignore her more often, except for when he wanted to show her off. She knew she was just a trophy wife for the business man.

The reason she felt so upset was because her favorite massage therapist was going on maternity leave and was not even sure about returning. Holly had started getting massages from Cho, a young Chinese woman, who owned a place called "Massage and Go." She needed them because all the stress she had been feeling. The massages did wonders for her.

"But who am I going to get now?" She wasn't truly upset with Cho, because even she wasn't that selfish.

---

The next morning, Holly walked into "Massage and Go." She looked around, sighing. The only available person to do her massages was a young kid who was something like an apprentice masseur. The very idea was abnormal. Who knew a person could apprentice so young. Cho said he was 17 and really getting good, but needed more hands on practice. She gave Holly a discount for as long as she uses the boy's services.

"Hello! I'm looking for Darren." She walked up to the front desk and rang the little bell to get someone's attention. In her hand she held her gym bag which had the garments she would be wearing for her massage. With Cho, she did not mind being topless, but with this kid, she was going to at least wear a bikini, though it was a thong Bikini.

RE: Masseur Training [Phoebe & Unchained]

Therapy. Darren sighed. Yeah, like therapy was that important. It was a little weird, being an "apprentice masseuse." Was that even a real thing? He'd never wanted to massage people for a living. Not his whole life, anyway -- but both of his parents were very therapeutic, his father a psychiatrist and his mother, well, she was a masseuse herself, but for a much more prestigious company. Not one that'd ever take Darren, and he was just fine with that. Those two weirdos could be as therapeutic as they wanted, just as long as they left him out of it.

... Still, that didn't stop mom from pulling her strings, and somehow she'd managed to set him up at a smaller business as a "masseuse in training," but, really, Darren was just an assistant, someone they passed the smaller clients off to when everyone else was busy. At first, he hadn't wanted to take the job at all, but after seeing how much it paid hourly, well, Darren just couldn't say no. And talent must have been genetic, because he was good -- damn good. Not that it was hard, relieving people of stress and pain... it just came naturally.

When the woman approached the desk that day, the young man had looked up from where he'd been sitting, a magazine in his hands. Cho was off, which meant his job was to check clients in and assign them -- but the day was slow, and Darren wasn't busy. He blinked dumbly, looked around, then blinked again. "Uh." Clearing his throat, he stood and approached, nodding a bit to Holly. "Yeah, I'm Darren? Are... are you supposed to be my client?" He gave the girl a once-over and blushed at her figure, raising a hand to rub the back of his head. "I think there might be a mistake, I, uh, I'm not supposed to work with female clients."

Well, that made sense. He was just a boy, and it was hardly appropriate. Still, the place didn't have many masseuses on hand that day, and Darren was the only one available. He couldn't just pass her off to someone else. "Did you talk with Ms. Cho?" Darren questioned, crossing his arms and shuffling on his feet a little awkwardly.

RE: Masseur Training [Phoebe & Unchained]

Holly smiled at the boy. He was cute, for a kid, though she had to admit if she had saw him elsewhere and had no clue about his age, she would have never pegged him for just a 17 year old boy. He did have the boyish quality, but something about him gave off more of a mature vibe. Maybe it was his eyes. Holly mentally shrugged. Whatever, it didn't really matter.

"Yes, I am Holly Winchester. My husband is Gerald Winchester, the movie producer. Maybe you've heard about him? Anyways, I'm supposed to get my massages from Cho herself, as she is the best." The blonde sighed. "I can't rightly blame her for taking time off for maternity." Holly waved her hand, hoping she did not come off as entitled to the best, even though her husband insisted they had the best of everything, at least for appearance sake.

"I was looking for you. There is no mistake." She put her hands on her hips and slightly leaned forward, the cleavage in her blue blouse becoming more noticeable. "I did talk to Cho. She said you were one of the most promising up and coming massage therapists, but you needed more hands on experience with every sort of client." She chuckled. "I take that to mean this is the first time you've practiced on a female?"

"It's no big deal, sweetie. I've got a bikini to wear." She winked. "No need to be shy. Where would you like me? Back room?"

RE: Masseur Training [Phoebe & Unchained]

Darren blinked, his blush brightening a bit. "Uh," the teen starter, looking left and right for a moment, hoping Cho would show up from nowhere and save him from the mess she'd put him in. But he knew hat wasn't going to happen, and so he faced Holly again -- at least, he tried to, though with her full breasts halfway on display, it was hard to pay attention to her eyes or face. Darren stopped himself from looking and cleared his throat again, giving the woman a short nod.

"Yeah, I'm pretty good -- I mean, that's what the customers say, I... I wouldn't really know." He sighed through his nose and nodded again. "Never a girl, no, but I guess there's a first time for everything, right? Just, uh, go easy on me if I seem a little nervous." Darren looked her up and down at the mention of a bikini. This was going to be hard -- really hard, having to smooth oil over her, touch her in every place except the places he really wanted to touch, listen to every little sigh she made as he worked the knots in her muscles out...

He tried not to think about it.

"It's just this way," Darren instructed Holly, waving the older woman along. He led her towards the back of the building, opening a door up that led to a private room that they'd have to theirselves. "Just, uh, get changed and I'll be with you. I can leave the room, if you want," he offered, his hand still on the door. He was sure that she'd ask him to go, but Darren wasn't sure if that was better or worse. "Or, uh, I can see if we have a masseuse around, if you're more comfortable with that?" he asked, looking unsure.

RE: Masseur Training [Phoebe & Unchained]

Holly thought his nervousness was adorable. She wondered when the last time it was that someone was this nervous around her. She shook the thought away and started to follow him to one of the private rooms. It was a small room with no windows, and low calming lights. Soft relaxing music was coming from somewhere.

She rolled her eyes at him. "No need to find someone else. Cho recommended you for a reason, I'm sure. Now just turn around and I'll change." When she was sure he was no longer looking, she pulled her top off. She wasn't wearing a bra. Her naturally large breasts jiggled as the shirt caught them. She gave them a brief glance, before bending over to pull down her short cut off blue jean shorts. She also wore no panties. Her husband did not like when she wore clothes like this, but Holly loved to show off her body. He was hardly ever home to stop her.

She didn't mind if a little bit of her ass and cleavage were showing. It created excitement, because she liked knowing men and even woman looked at her with either desire or jealousy.

She grabbed her red and white flower printed bikini out of her bag. The bottoms were thong styled and tied on both sides of her hips. The top tied in the back. She put the bottoms on easily enough, but the top posed a problem.

"Hey, Darren, can you tie this for me?" Holly asked, turning around so the other could tie up the strings.

RE: Masseur Training [Phoebe & Unchained]

"Uh, yeah, sure thing," Darren said, and he closed the door fully, doing his best not to turn away from it. But that proved difficult -- he could hear her moving to take off her clothes, struggling slightly as she tried to wriggle her way out of them. Darren swallowed hard and looked back for a second -- just a second -- as Holly bent over low to pull off her shorts, naked breasts hanging in the air. His eyes widened a moment and he looked away again, though the entire room felt hot all of a sudden... and the poor, hormonal boy couldn't help from noticing that his jeans were suddenly a bit too tight.

"Huh?" When she spoke up, he turned again, blinking as she turned her back to him. Darren listened a moment, then shamelessly looked Holly up and down while she couldn't see him, eyes glued to her ass and the way her hips seemed to curve. "Yeah, sure." He sounded unsure as he stepped forwards, hands reaching out. He steadied them before taking the strings, hoping she couldn't tell how truly nervous about this all he was. Darren tied them easily enough and tightened them in a way that would cause her bikini top to tightly hug her ample chest, and he pat her lightly on the back, his hands briefly placed on her wide hips.

"All done," Darren said, moving up to hold her shoulders. He gently kneaded his hands in to them as he guided her towards the table, instructing her to lay down. "Alright, so, uh, back or front?" he asked, wondering if Holly wanted to lay on her belly or her back first. Either way, Darren found himself growing more excited... and a lot more nervous...

RE: Masseur Training [Phoebe & Unchained]

"Thanks!" She said when he finished with her bikini top. She had no real clue what was going on in his head. She knew she had a good body and the people stared, but there were times when she could be a little clueless, and she did space out every now and again. She wasn't really an air head, but some people might say otherwise.

"Mm," She lightly murmured when he started to massage her shoulders. Already it felt nice. She let him lead her to the table. "Back first, I think." Holly got onto the table, her ass fully in view as she got comfortable. That was the thing about thong bikini's; they did not leave much to the imagination. She was putting a lot of trust in this kid. A couple tugs and her bikini would be laying on the floor.

"I think I pulled a muscle in my lower back area yesterday at my dance class." She slightly turned on her side and reached around, touching the area that was sore. It was the place right where her back and ass met.

Next time I should bring more suitable under clothes. A bikini was not the best choice! She thought as she laid there.

RE: Masseur Training [Phoebe & Unchained]

Darren was growing a little more comfortable with her, himself, and the entire situation, truth be told... He still couldn't help himself from stealing the occasional glance or two, and he was supposed to put a towel over her ass, Holly might've remembered, but the teen either forgot or simply chose not too, his eyes taking in as much as they could before his skilled hands went to work. Neglecting the oils for now, Darren simply placed both of his palms in to her lower back, applying pressure and kneading the skin thoroughly.

"Dancing, huh?" Darren asked, hoping to distract the both of them. Well, a little bit of conversation went a long way, and if he kept her talking, maybe she wouldn't notice he was staring directly at her bottom the entire time he'd been working. "What kind of dancing do you do? I, uh, I don't really dance, but my sister does." He moved around a bit, hoping to hit the spot that seemed to comfort Holly the most, gauging her reaction carefully as he pushed in to her skin, palms working in to the warm flesh just above her ass now. "How's that feel?"

RE: Masseur Training [Phoebe & Unchained]

"Mmm, oh yeah, that feels great." His hands really were like magic. Cho had not been wrong when she said he was very good and had a lot of promise as a massage therapist. The blonde smiled, moaning gently every so often as he touched her in the places that were most sore. The tension and pain was slowly leaving her body, and she had never felt so relaxed.

"All sorts of dancing, but mostly the stuff my husband doesn't approve of." She smirked against the massage table. "He's really strict, but since he is never home, I can get away with a lot of things he hates, but I happen to like." She sighed. "Oh, never mind me, marriage life can be so complicated when there is money involved or famous people."

"The main type of dancing I'm focusing on is..." She paused, wondering if she should be talking to a kid about this. He was 17, so in less than a year, he would be considered an adult, but still. "Well, pole dancing..."

RE: Masseur Training [Phoebe & Unchained]

Darren quirked a brow, blinking slowly at what she had to say. Money, famous? Oh, well, it seemed kind of obvious now, didn't it? Holly must've been a trophy wife, or something like that, the teen figured. She was young, hot, had money, and, well, maybe he was quick to judge, but she didn't seem to be all there in the head, either. Not that she was stupid; but some people just didn't have to work for a living. When you don't use your brain enough, sometimes you forget it's there at all...

At her admission, he paused for a moment, his hands pressed against the small of her back, and Darren blushed. So she was crazy hot and she knew how to work a pole. Great. Could this get any better? Could it get any worse? This was practically torture. "I, uh, I don't think my sister's in to that," Darren chuckled nervously, feeling a little sheepish. He tried not to imagine Holly's naked frame grinding against a pole, but it was hard. Those jeans of his kept on getting tighter. He cleared his throat.

"That's cool, though. Do you have any other hobbies?" He was feeling a bit more adventurous, now. Darren listened to her soft moans and groans as his hands traveled, taking not of which places she enjoyed, which she didn't. Soon enough, he was all the way up her back and on her shoulders again, palms gently but firmly pressed in against the back of her neck, and he pushed her blonde hair out of the way so it didn't interfere with his work.

RE: Masseur Training [Phoebe & Unchained]

"Its nothing shameful, depending on the context. I don't dance at a strip club or anything. Though there has been a couple times I considered it... not that I should be talking about that here." She felt her cheeks warming. I really need to watch the kinds of things I say to him!

"Some people use it as a workout and does it work you out. No wonder I pulled a muscle, it takes a lot of strength to do some of the moves and I overdid it." She closed her eyes just sinking into the feeling of him touching her. "But you're right, it's just not for everyone." She bet his sister was on the younger side and did something cute like tap dancing or clogging.

"Well, I like swimming. We have a pool and I'm always either in it or our hot tub, no matter the weather outside. I like jogging and doing outdoor activities." She moaned louder than usual when his hands traveled to her neck. Apparently, she had a kink there she had not known about.

"Mm, that's wonderful. As I was saying, I like doing things that keep me fit, and believe it or not, I like to read. I get people take one look at me and assume I'm a dumb blonde." She scoffed at the idea, then turned over onto her back, to look up at him. Her large breasts were begging for attention beneath the flimsy thin bikini top. Her nipples were slightly hard, because of how good his hands were making her feel.

"What about you? What do you like to do?"

"Your hands feel amazing. Can we start the real massage with the oils?" She glanced down at her body and then back up at him. "You can start on my front side."

RE: Masseur Training [Phoebe & Unchained]

Darren smirked at her: "I don't think you're stupid," the teen offered, and for a moment, he felt bad about his initial thoughts of her. Maybe she was the hot, busty trophy wife, but that didn't mean she fell in to the same category as the rest of them. It was just a stereotype. Still, stereotypes always had a little bit of truth behind them. The boy tried not to picture Holly at a strip club, underneath the flashing lights and surrounding by music as she spun around on her pole. A chill went down his spine, and he tried to fight his raging hormones, but they seemed ready to take control. Darren had to be careful.

When she spun around to lay on her back, his hands immediately came up, hovering in the air, and Darren froze. "Uh." Her front was much more intimidating than her back. At least she couldn't see him staring at her round ass, the other way around -- now he'd be busy ogling two barely-concealed and very large breasts. Her constant moaning didn't help, either. The way she made her little noises and talked about her stripper fantasies, it almost sounded like she was trying to get him to make a move...

Yeah, right.

"I'll, uh, I'll try and ignore the important bits," Darren nervously laughed at her, reaching beneath the table for something. He came up with a small bottle of oil, lathered it on to his hands, then rubbed them together, reaching forwards to get started on her chest. His hands started at her shoulders then moved down to her sternum, gliding between her breasts and coating her in a slippery sheet of oil. Try as he might, there was just too much cleavage to ignore entirely, and while he wasn't quite fondling her, his hands were still touching her breasts every so often as they moved their way up and down.

Darren seemed to notice this, and so he cleared his throat again. "Sorry," he apologized, making eye contact for just a moment. "There's just, uh -- well, they're hard to miss." His cheeks were flushed again, and he went back to focusing on his work, using both hands to smooth the oil up and down one arm and then the other, messaging her skin and loosening her muscles as he worked his way up and down.

RE: Masseur Training [Phoebe & Unchained]

The feeling of the oil on her body made her sigh and moan slightly as his hands started to rub around her shoulders, belly and around her boobs. She could tell he was trying to avoid directly touching them, and could see he was having a little trouble keeping his teenage hormones at bay. She couldn't blame him though and still wondered what Cho was thinking allowing someone his age to work here, and why she would suggest he work on her.

"Well don't apologize. It's not like you can help it. There are part of me, and a pretty big part at that." She smiled up at him. "Just relax. I'm not going to be offended if you accidentally touch them, sweetie." Even though this couldn't go beyond professional, with the occasional accidental carcasses on her sensitive parts, she couldn't help enjoy the excitement it gave her. She could not remember the last time a man had touched her. Her husband had been away for a really long time on business.

"You don't have to pretend you're not looking. If you want this to be your job, you'll have to get used to looking at all sorts of body types."

RE: Masseur Training [Phoebe & Unchained]

"Yeah, I guess." Darren sounded i convince, and he still looked nervous, but with the second clearing of his throat, he nodded to the older woman and found his courage again, moving his hands to her chest and directly across her breasts. His palms caught them as they passed, lathering her top with oil, and as they slid on by and down her stomach, he released them with a faint jiggle, not daring to make eye contact with her.

He kept working his way down Holly's body, his palms pressing in to her stomach and across his hips before he quickly moved down to begin on both legs, rubbing his hands in to her skin in slow, circular motions. "Guess I should get used to it," he said aloud, looking up at Holly again. "If you want to turn back over, you can take your top off," Darren offered, heart in throat. That might've been a bit too far -- if it was, hopefully she didn't tell Cho about it. At least he wasn't insisting she take it off while she was laying on her back with her chest on full display like that...

Cheeky little bastard, Holly thought, though in good humor. She rolled her eyes at him when his attention was focused on her legs, and he was not looking at her. She knew going topless, or even naked was normal during some massage sessions, but usually not if the massage therapist was a male and the client was a female, and vice versa. She went topless with Cho with no problem, and the Chinese woman gave the best breast massage that Holly had ever had.

"Yes, you should get used to it." She set up briefly and untied her bikini top, letting it fall to the floor. "I will still lay on my back, though." She laid back down, her breasts jiggling as she did so, parts of them slightly saturated in the oil that had soaked through her bikini.

Nothing wrong is happening here. He needs to learn, that's all. She reasoned with herself.

RE: Masseur Training [Phoebe & Unchained]

Darren stopped his massaging for a moment to look up at her, his cheeks painted red. Stupid, that was a stupid thing to say -- she was probably going to get up and hit him now, then storm out, then tell Cho, and he'd be in a world of trouble. But that didn't happen. Holly sat up, and when the blonde reached behind herself to untie her top, Darren's blue eyes were as wide as saucers.

"Wh--?" he asked, but couldn't finish before her top simply fell, freeing her breasts. Darren watched as they bounced free, and he swallowed the lump in his throat, simply staring. Something was definitely going on her. Holly had to be some sort of MILF -- older women were in to that sort of thing, right? Looking for younger boys to take advantage of to show that they still "had it?"

Darren looked away and finished up on her legs before moving towards her core again, both hands resting on her stomach. He tried to be as professional as he could, starting to give her a genuine massage now that she was covered up in oil. Most of her was covered up, anyway. His fingers pressed in to her skin, working out all of the tension, before coming up and cupping one of her very large breasts with both hands, his palm smoothing over her hardened nipple, fingers digging in to her tender flesh as he began working on her tits now.

"Like that?" Darren asked, looking up at her eyes. He'd never massaged a woman's breast, after all. He cupped her large orb with one hand and gently squeezed it with the other, letting her nipple pass through the crevices between his fingers. The bulge in his jeans was fairly obvious now, and it looked rather impressive, from what she could see.