Masseur and the MILF

Finishing my first day of work at the Club felt anti-climactic. I finally met the third masseuse, a friendly woman named Catherine, who went by Charlie, on my way out. She was in her fifties and had the casual demeanour of someone who had been doing her job for a long time and wasn't particularly concerned about doing anything else.

I went home and crashed in the little one-person loft I'd managed to find in town to rent. It was small, but it was all mine. I was sure if I'd asked my Mother would have let me move back home, but there I would have been dealing with my Father's disapproval at my choice of career and I'd gotten enough of that shit before I left.

Before I went to sleep that night, I couldn't help it. As soon as my head hit the pillow, my hand was on my cock as I closed my eyes and pictured those perfect tits on Eden. They weren't super big, but still nicely suited to her frame. Then I thought about her lips, and how expressive they were. How she smiled when she laughed, and she got a twinkle in her eye when she was teasing me. I thought about running my hand through her hair and grabbing her to hold her still as I kissed her.

It was somewhere between imagining me mounting her from behind, and imagining her riding me as she screamed my name, that I came.

After that night, I settled into a decent little routine. I was at work by 8am, the first client at 8:30 and I was out of there by 5:30pm. Most of the clients I didn't know, but at least a couple of times a day it would be someone who knew me through my parents or remembered me from around the Club during my teen years. It was smooth, if a little lonely, since the most contact I had with coworkers were brief encounters with Jessica when I was escorting clients to and from my room.

The highlights were my lunches with Marissa. I learned quickly that she was casually friendly with most people on the staff, and had worked at Greenmeadow for the past two years, but she generally liked to keep to herself. At least until I inserted myself into her lunchtime. We kept the conversation light, but it never got mundane. We only talked about the weather once, and that was because it was expected to pour buckets of rain and she was thinking she'd get off work early because of it. She had a laugh that I liked, and she had just a little touch of 'goth girl' to her that I wondered what she dressed like when she wasn't at work.

The only problem with Marissa was that, while we quickly became work friends, she didn't want to date. And that was OK, I just also happened to be horny as hell and so when I wasn't fantasizing about Eden, I was fantasizing about Marissa's cute lips and how big her breasts actually were under the deceptive polo shirts.

Leaving her that Friday after lunch, I had a smile on my face that made Jessica quirk her head to the side and give me a look as I returned to the spa. "You look like the cat that caught the canary," she said.

"Aren't you a little young to be using a phrase like that?" I asked her.

"OK, Boomer," she rolled her eyes. We'd developed a decent back-and-forth when clients weren't around, probably helped by the fact that I'd made sure to check with her that she was getting tipped out through the automatic tracking system the Club used. The Spa was members-only, and they all paid through their accounts so no money ever changed hands in the Spa including our tips. The clients just let Jessica know what membership number to charge and how much to tip. 'Tipping out' wasn't a required practice, but it was another one of those things that I'd learned about in my practical placements - always take care of the admin person, and they'll take care of you. So Jessica was getting 10% of my tips. "You've got Mrs Killian in five," she continued. "And then four more folks lined up. I did end up getting a walk-in request and filled that open 3:30 slot you had. Then you've got your favourite client."

"She was my girlfriend's mom, Jessica," I said, shaking my head as I walked back to my workroom to get it ready.

I didn't miss the fact that she hummed the tune to 'Stacey's Mom' behind me. Loudly.

Errant thoughts of my nearing appointment with Eden were interrupted when I met Mrs Rachel Killian. When I went out to meet her I was expecting another sixty-something woman with chronic arthritis in several digits who wanted her calves and ankles massaged to help with her worsening varicose veins - it was pretty much the most popular issue I'd faced all week.

What I met instead was a striking woman of some sort of mixed race. She was part black and wore her hair in long kinky braids threaded with white strands. She was tall and curvy, but clearly took avail of the Club fitness facilities as she wore her casual but trendy cream dress extremely well.

"Mrs Killian," I said when Jessica introduced me. "It's a pleasure to meet you."

"I have to tell you, Trevor. Eden didn't oversell you at all," she said. "I hope your hands are as good as she said they are, too."

I actually felt myself start to blush a little bit and pointed her to the changing areas so she could go get ready.

"I'd hit that," Jessica said once we were alone in the lobby.

"What?" I asked, turning to look at her in surprise.

"What? She's stupid hot," Jessica said.

"Jessica, you're seventeen," I said.

"And?" she laughed. "That doesn't mean I can't look at a woman like that and think, 'Damn!'"

"I didn't even realize you were into girls."

"They're all I'm into," she said. "And I know, you were just waiting for my jailbait self to turn eighteen so you could sweep me off my feet."

"Harr harr," I deadpanned with a raised eyebrow. "Seriously, that's not even a funny joke."

"Maybe to you," she snickered.

I started to wonder if maybe I was gettingtoo friendly with Jessica.

Rachel Killian came out of the changing rooms in the robe, her warm golden-brown skin more heavily revealed as I walked her down to the room. I ran through the questionnaire with her, and while she didn't flirt with me as directly as Eden did, she also wasn't as clinical or impatient as most of my clients. She joked lightly and smiled with a warm quirk to her plush lips. I was surprised to find out she was in her early forties, and she mentioned she had a couple of kids in their young teens.

I went through the motions, stepping out to allow her to get under the sheet on the massage table, and then re-entered.

Things went off track about twenty minutes into the appointment.

"Mmm," Mrs Killian groaned happily. She'd asked me to put some extra work into her thighs, and I was slowly working my way down her vastus medialus, working out a couple of tense spots. "Fuck, Trevor. I can feel that shooting right up to my ass."

"Is it going up this way, or this way?" I asked, tracing along the outside and inside of her thigh. "And is it constant, or shocks of pain?"

"Shocks," she said, and leaned around, arching her back so that she could take my hand and run it up her inner thigh. "My leg's actually twitching. Feel that?"

I did. My hand was on her bare inner thigh. She'd worn panties, so I wasn't in danger of touching anything truly inappropriate or even seeing it. The top sheet was folded neatly over her generous butt anyways. But the top half of the sheet had also fallen down, and as she'd raised her torso up off the table and bent back towards me, her boob was off the table and hanging there staring at me. Mrs Killian's breasts were pretty large and magnificent, capped by a wide, pale areola and a little pebble of a nipple.

"I do," I said, trying my damndest not to stare. "I probably hit a rough spot that's been building for a while. As long as it's just shocks and not a constant pain we can probably go a little heavier and work it out. Just tell me if it becomes constant and throbbing, and we'll give it a quick break."

"OK," she said with a nod. She let go of my hand and reached up, rubbing it down the side of her tit and tweaking her nipple casually. It happened entirely non-sexually, but felt like a sexual movement, and I wasn't sure what to do with it. But she went back down onto her belly, her boob crushing back to the massage table. "I trust your expertise. I just wish my husband had your hands, I'd be getting a different kind of shock."

I snorted, and she laughed, which made her butt jiggle under the sheet.

Nothing else truly untoward happened with Mrs Killian. I worked out that shooting pain, and wrapped up the massage on time. She thanked me, and said she was going to start booking longer times with me - she felt more relaxed than she had in weeks. She did give me a quick peck on the cheek as I walked her back out to the changing hall entrance once she was properly dressed again, and I didn't fail to notice Jessica give me the double-eyebrow lift to tease me without saying anything.

The rest of my Friday afternoon started to blend together, and I lost track of which client I was on, as I daydreamed of Mrs Killian's legs. They were nicely muscled, and her smooth, golden brown skin was like massaging a soft marble. Not to mention that peek at her boob.

It was funny; most of the Club clients were older, if not elderly, but I hadn't really considered the fact until Mrs Killian that I was dealing with wealthy old men. And what did wealthy old men like?

Trophy Wives.

I didn't know who Mr Killian was, but whoever he was I hoped he had a pipe in his pants and knew how to use it or else Mrs Killian going unsatisfied was a travesty to humanity.

And that was the weird shit going on through the back of my mind when I went out to get my next client and I was greeted by Eden, already in her robe.

"Hey, Trev," she said. "I got here a little early, didn't want to waste a second of our session."

"Hello, Eden," I said, and went to shake her hand but she pulled me into a hug and kissed my cheek.

"None of that now, hon," she said. "We've known each other too long."

"Alright, alright," I grinned and made sure not to look over at Jessica because I didn't want to give her any more ammunition.

Eden slipped her arm through mine and I walked her down to the room. "How has your day been?" she asked me. "My friend Rachel said she had a session booked with you."

"I did see her," I said. "I can't really talk about it though."

"Oh, that's fine," she said, patting my chest lightly. "She's got some great tits though, right?"

I coughed on my own spit for a second, needing to clear my throat as Eden chuckled and rubbed my back.

"Sorry, hon," she said. "I just wanted to know if she gave you the same extra tip I did."

"No comment," I said once I had my breath back.

We went into the room and I shut the door behind us. When I turned back around I was shocked all over again to see that Eden was already stripping off her robe and hanging it on the wall. She was only wearing a thong again, this time a black one that had two waistbands with open space between them in a cute lingerie-ish look. And she was braless.

"Eden!" I said, and reached over and flicked the switch on the wall to turn the glass opaque and frosted.

"Oh, you've seen it all already, babe," she said, giving me a quirky little smile. She was pretty as hell, that blonde bob of hers accenting her jawline and the curve of her neck, and she stood there with one hand on her hip and her breasts pointing right at me. She had that teasing gleam in her eye, so I knew she knew what she was doing. I also noticed she'd swapped out the barbel in her right nipple with a little golden ring. "And to be honest, we've got a whole hour and I want a full body massage. I want to be putty in your hands, so there's no point in me being bashful. Is that OK with you?"

"Eden, if that's what you want, I'm happy to do it," I said. "But I'm not the only person who works here and that could have been big trouble for either of us if someone had walked by and seen."

"I wasn't thinking," she said, stepping towards me and putting one hand lightly on my chest as she looked into my eyes. I found it kind of entrancing how she could look me in the eye on an even field. I wasn't particularly tall, so it's not like Eden was a towering woman, but as a teen I'd always seen her as 'an adult' and not really registered that much more detail about her other than that she was the hot stepmom of my girlfriend. Now it was different. "I'm sorry, hon. I shouldn't be so flippant with your job."

"I appreciate that," I said, and my hand naturally fell to her waist as I gestured with my other to the massage table. "Let's get started."

She smiled at me again, giving me another of those closed-lip, quirky ones that were half teasing and half sincere. "Of course," she said. "Let's use every minute."

Eden climbed up onto the table, not bothering with the top sheet, laying with her head sideways on the table so she could watch me as I quickly put my oil bottles back into their holsters on my belt. Her bare back and legs looked sleek and smooth, and I couldn't help comparing her to Mrs Killian from earlier - they were both beautiful women, but built differently. Rachel Killian was fit and voluptuous in the way that a woman could hold onto her body fat in the right places with weightlifting, while Eden was yoga-and-CrossFit athletic. She wasn't super skinny, and her mid-thirties body showed little hints that she'd had her child, but she was still sexy as hell.

I started at her feet, softly starting by applying oil to the soles and running my fingers around her toes and that cute gold toe ring as I asked her how the week had gone. She told me about how she shared custody of her son Oscar with her ex-husband, and how she missed the little guy when he was gone with his Dad. And she told me about a run-in she had with another Mom at the local playground she brought Oscar to, and how she was thinking of getting a dog when he was older. I worked my way up from her feet to her calves, then up her thighs.

As I reached her upper thighs, mid-conversation, she said, "Don't be afraid to work my glutes too, babe. Really go in on my ass." And then she went back to the conversation about dogs, and as I just kept up my progression she pivoted to asking about how I liked working at the Club and being back in town after three years away. And as I kneaded her ass, feeling those soft cheeks and the muscles underneath, I told her about how the job was fine for now, but I needed to try and get some sort of a social life going.

I couldn't be sure if I imagined it or not, but as I manipulated her ass, her cheeks naturally pulling apart occasionally with the movements and I got little peeks at the thin black fabric covering her asshole and down to her mound, it felt like she was pushing her ass up at my hands.

And then I was moving on. Reluctantly, but I couldn't tell myself I hadn't finished being thorough and had been drifting into self-indulgence. I slid my hands up to her waist and the small of her back, adjusting the higher waistband of her thong down a bit to properly start working her back.

"Have you met any cute girls yet?" she asked me. She'd closed her eyes at some point as I'd been massaging her butt, and she had a soft, serene smile she only broke to ask me questions.

"Well, I met one very beautiful woman but she's way out of my league," I said

"You'd be surprised what leagues beautiful women like to play in," she said. "But you know what I meant, you flatterer."

"There is one girl," I said. "She works here in a couple of positions. But she says she doesn't ever date, so I'm happy just to start making some new friends."

"That's nice," Eden said. "Though I'd bet it doesn't stay platonic for too long."

"And why is that?" I asked.

"Because either she'll figure out you're a catch on her own, or someone else will and she'll get jealous," she said.

"Now who's being the flatterer?" I asked, slowly working my thumbs up her back and reapplying more oil to my hands every once in a while.

"Just calling it as I see it, babe," she said.

And then we were quiet for a while, except for the happy grunts and moans of a person deep into massage-brain. It wasn't an official thing, just something I liked to think of as a factor of successfully getting a client to fall into a deep relaxation. The problem was that Eden's little grunts and moans, with girlish sounds in her chest or throat, were having an effect on me that I wasn't supposed to have.

By the time I got up to her shoulders, Eden was breathing deep and slow through her pouted-open lips. I moved further up her neck, softly moving her hair to the side and working my fingers up her spine to the base of her skull, and then back down either side and then along the tops of her shoulders and collarbone.

Without me prompting her, Eden opened her eyes slowly and grinned at me, then turned over onto her back. "All over massage, right babe?" she confirmed with me.

I swallowed a little. Usually a 'full body massage' kept a strip of folded towel on the chest and groin of a female client. Full didn't meanfull.

"Whatever you are comfortable with," I said quietly to her and positioned her head so she was looking straight up. "Try not to move for this next part." And I started to reverse my massage path, going from top to bottom and starting softly at her hairline and temples. I spent the next few minutes with every reason in the world to be staring at Eden's beautiful features, and I didn't waste them.

Soon enough I was massaging down her throat to her collarbone as Eden softly panted from the intimate face massage, her chest rising and falling as I tried not to glance up at it - I failed regularly, but not as badly as I could have. As I reached the top of her chest she opened her eyes, looked up at me, and raised an eyebrow. "You said anything, right Trevor?"

"I did," I said, assuming she was talking about how I would soon reach her breasts. I hadn't exactly gotten a lesson in my program on 'breast manipulation' beyond how to do a basic breast cancer screening, but I'd definitely gotten some practice with my study/fuck buddy back at college. That didn't change that it was right on the fucking line of being unethical, even if she was asking me to do it.

Of course, Eden managed to surprise me once again.

"Good," she said. "Because I feel amazing right now, and I want to do that for you, too." And she reached up over her head towards my waist as I stood at the head of the bed leaning over her. And she began to unzip my pants.

"Eden, this isn't-"

"Shhh," she shushed me soothingly and softly. "Trev, it's been almost two years since I've been with a man. You make me feel comfortable and safe, and horny just by being you. I want to do this for me as much as for you. So let a middle-aged, divorced, single mom ex-trophy wife do this for you."

She got a hand inside my pants, fingers teasing around the root of my cock, and I stopped really thinking about what the right choice here was. Mostly because I didn't care, because Eden was fucking hot as hell both in body and in personality and I hadn't gotten laid in a couple of months, and I'd been fantasizing about this all week.

One fucking week and I was already doing the thing I thought I never would. But it was fucking Eden Cargill. Daisy's hot mom.

Eden fished my cock out of the fly of my pants and turned on her side to look at it, but even as she had it in her hand, and moved her lips closer and closer, she hesitated as her jaw dropped open cutely. "Oh my God, Trevor. This is an absolute tool. I love the look of this big, angry vein," she said and then licked the tip of her tongue up the vein on my shaft.

"Oh, fuck," I grunted. I had one hand on her shoulder as she was laying sideways on the other, and slid it down to the back of her head as she brought my tip to her lips and softly fit it into the space between them, treating it tenderly like a tentative first kiss. "Eden, you are..." I exhaled heavily as she used her lips to massage my cock head a little, unable to finish my thought coherently.