Masseur and the MILF 2; Part 2 (Alpha)

Sponsored by Toodles

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‘Hey,’ I texted while I was lying in bed. ‘We didn’t talk about boundaries or what might be clingy to you, so this is my one text. I had a lot of fun last night - with all of it. I know you’re crazy busy, so let me know if you want to hang out and do stuff, or ‘stuff.’ Otherwise, I’ll see you Monday and try my best to not be weird :P’

I had visions of Marissa in my head, and I didn’t really want to roll out of bed while her curves were floating through my imagination. The great thing about working a standard shift at Greenmeadow was that my weekends were all my own, so sleeping in late and jerking off was totally on the menu. The fact that I was also able to scroll back up to her previous titty pics she sent me made it even better.

My flow was interrupted by getting a text from her though.

‘I had a lot of fun too!’ She sent. ‘But I’m totally booked all weekend. Unless you want to come be the Cart Girl’s unpaid intern all day ;)’

I chuckled and smirked a little. ‘Tempting, but then I’d be competing for your tips. You’d be surprised how well I can rock a tight pair of khaki shorts.’

She sent me a trio of crying laughing emojis, followed by a kissing emoji before saying she’d see me Monday.

I was halfway back into the groove, remembering Marissa’s tits as she’d rode me in cowgirl, when I was interrupted by a call. For a second I was hoping it was Marissa calling me for a quickie or something, and had a weird emotional rollercoaster as I realised it wasn’t her, but then got happy all over again when I realised it was Eden.

“Hey, Eden,” I said, answering it.

“Hey, Stud,” Eden said, and just the tone of her voice sent tingles through me. I could hear the cute smile on her lips. “I just wanted to call and see how your date was last night? Did you get some?”

“I don’t know if it’s fair to kiss and tell, is it?” I asked. “I’m supposed to be a gentleman.”

“Ugh, you tease,” she laughed. “Maybe this will convince you - I rubbed my pussy last night thinking about you and some young thing fucking like rabbits.”

I groaned a little. “Eden, gorgeous, if you think I’m the teasing one…” She laughed on the other end of the line. “Look, I might not give you all the dirty details,” I continued. “But it was a pretty interesting evening.”

Eden listened as I told her about the party, and then everything that had happened with Jessica. She was cheering for me when I told her about the kiss with Marissa in the woods, and then shocked and worried for Jess. I had to ask her not to ask around since I didn’t know what sort of privacy the teen and her mother would want to have around the situation. Then I got to bringing Marissa home, and snuggling on her couch while we watched a movie.

“Please tell me that isn’t all you did,” Eden said. “I’m living vicariously through you here, Trev.”

“Are you touching yourself?” I asked with a little smirk.

“No,” Eden said. “Well, just my nipples. I’ve got the kiddo all weekend, he’s just out with his grandparents for an hour or so doing some errands while I have a moment to myself, but they could be back any time.”

“Have I mentioned that I love your nipples?” I asked, my smirk growing. “I love kissing all around them, and wrapping my lips around them and sucking, and tonguing them, and-”

“Treeev,” she groaned, making me chuckle.

“We had sex,” I admitted. “And it was good. Really good.”

“Is she a freak like your little MILF pet?” Eden asked lowly.

“She has freakish tendencies,” I said. “We’re taking it a little slower than we did on that stuff.”

“Mmm, good,” she hummed. “This girl sounds like the right speed for you, darling. I want you to be happy; hopefully, that means she might be open to me getting a piece of you sometimes too.”

“Marissa and I aren’t dating, or official or anything,” I said. “Right now it’s kind of just ‘fuckbuddy’ stage.”

“But you do want to date her,” Eden guessed. “And don’t lie, Trev. I can hear the way you talk about her.”

“She’s… pretty great,” I said.

“Then don’t pressure her, but make your intentions clear,” Eden advised me. “Doing it while that cock of yours is in her wouldn’t hurt either.”

I snorted and we both laughed.

“Ugh, I wish I could just get you to come over, but I really do have a bunch of stuff I need to get done before my parents bring back the kiddo,” she said. “I’ll be thinking of you in bed tonight, Trev.”

“I’m thinking about you in bed right now,” I groaned.

She hesitated a moment, then breathed heavily. “Send me a picture?”

“Hold on,” I murmured, and quickly threw my sheet off myself and took a picture of my rock-hard cock as I stroked it with one hand. I sent it off to her.

“Fuck,” Eden sighed. “OK, now I’m definitely fingering myself tonight.”

“Send me something when you do,” I said.

“I will, Stud,” she said, that warm smiling tone back. “I better go now. I’m so glad you had a good date! And I’m looking forward to Tuesday.”

“Thanks, Eden,” I said. “And me too.”

“Love you in the sex,” she said and then made a kissing noise.

“Love you in the sex, too,” I chuckled.

I dropped the phone and let out a long breath, still holding my cock. Talking with Eden reminded me that Marissa had been open to a threesome with a ‘MILF’ I knew - now I just needed to figure out a way to make that happen.

Then again, Eden had insinuated that I would be getting a surprise on Tuesday, too. And that it may or may not be her MILF friend Rachel.

I had more than enough mental ammo between the three of them to get myself there.

- - - - -

“Oh my God, Trevor,” Jessica said as I walked through the door to the Greenmeadow spa area. She came around from her little plinth where she worked most of the day and crashed into me with a big hug. “Thank you so much.”

“Hey, Jess,” I said, giving her a squeeze back that matched hers. “How are you feeling?”

“Still kinda shitty, but better than Saturday,” she sighed, pulling away but keeping a hand on my arm for the moment. “My mom was pissed and tearful, but she said I’d done the right thing when push came to shove and trusted the right people. I’m grounded, but she let me keep my job here.”

I let out a relieved sigh. “Did the Doctors figure out what it was?”

“Alcohol poisoning,” Jess said. “Apparently some of the drinks I was taking at the pre-party were someone’s Uncle’s moonshine or something, and not just vodka spritzers like I thought. They pumped my stomach, and I was in the hospital all Saturday and got sent home yesterday morning saying I was lucky you and Marissa got me there when you did. So now you’ve saved my life and stuff, so…” She crashed right back into me and gave me another hug. “If I’d gone unconscious and people decided to just let me sleep it off or something, I might have died,” she mumbled into my shirt.

“I’m glad I was there to help,” I said, rubbing her back gently. Thankfully we were alone in the lobby - appointments didn’t start for another twenty minutes or so, but the steam and cold rooms were open for use as soon as Greenmeadow opened.

She pulled away again and wiped under her eyes. “Um, sorry,” she said. “I just- Thanks.”

“You’re welcome,” I said, taking her hand for a moment and giving it a squeeze before letting it go. “Now, little Miss Moonshine, I need to get ready for the day, but you tell me if you’re feeling like crap - if you need a half day I’ll figure out a way to cover for you.”

She groaned at the nickname. “Please, not that,” she said.

“Oh, it’s that,” I said with a grin. “Just between us, though.”

She rolled her eyes and sighed dramatically, but as I turned to head down Massage Alley I saw the flicker of a smile at the corners of her mouth.

- - - - -

“Did Jess find you?” I asked Marissa by way of hello as I grabbed a seat next to her at our usual lunch table.

“Hey,” she said. “No, not yet, but I’ve been running the Booze Cart all morning on Course 2.”

I gave Marissa a quick recap, and we commiserated a little about our own first ‘too much to drink’ escapades. Neither of us had thankfully gotten to the point of alcohol poisoning, but the stories were funny. Then our conversation moved on to work stuff, and the random crap we’d usually bullshit about over lunch.  She mentioned that we needed to watch the rest of Starship Troopers, but otherwise, our night together wasn’t mentioned at all.

And it was kind of nice, not feeling pressure to address things or something.

Right at the end of lunch, as she was cleaning up her garbage, Marissa stopped and winced a little then rubbed her shoulder. “You think you could do that thing for me again?” she asked. “I’ve got like, a half hour after work.”

“Have you been doing the stretches I showed you?” I asked.

She blushed a little as she chewed on the inside of her lip. “Not really,” she admitted.

I sighed. “Alright, yeah. I think I’m booked through five, and a few minutes after that?”

“Sounds good,” she said. “Thanks, Trevor.”

“See you then.”

- - - - -

“Oh, you fucking bastard,” Marissa groaned in pain.

I coughed lightly to the side, trying to hide my snort. “I told you to do the stretches,” I said.

“Yeah, well it didn’t hurt this much the last time you did it,” she said. “Owowow, that fucking hurts!”

I sighed and eased up a little. “Did something stressful happen over the weekend? You’re knotted up like crazy.”

She was face down on my massage table, topless and with a towel covering her ass. I’d been hopefully expecting at least a topless show, what I hadn’t expected when Marissa showed up a few minutes after our official closing was that she’d strip out of all her work clothes with a tired smirk before hopping up on the table. That impish smirk hadn’t left her lips until I’d started to press into her tension points.

“Um… fuck… if you mean other than helping a girl to the ER?” Marrisa moaned. “Then, um, there was a fight at the women’s shelter I had to help break up. And I got stiffed on a bill at the diner Sunday morning. And I’m falling behind on some correspondence I need to follow through on for my graduate program.”

I sighed again and shook my head. “Izzie, you really need to find time to relax. You’re fucking impressive, but you’re running your body ragged. When was the last time you did something mellow, and just for yourself?”

“.... well, there was Friday night,” she said.

“The part counts until the end, but our sex definitely wasn’t mellow,” I chuckled.

She snorted and grinned at me. “Fair enough.”

“When before that?”

“I… don’t know,” she said.

I took a breath and wondered what the fuck I was doing, risking my job like this. “Alright,” I said. “Then the way I see it, if you're not going to mellow out yourself, I’m going to do it for you.” I wrapped my hands around her hips and turned her over onto her back. Her breasts swung heavily and settled, and she ended up naked and looking up at me.

“Oh yeah?” she asked, eyeing me up and down. “How are you going to do that?”

I pulled my chair over next to the massage table and then manhandled her so that she was pulled most of the way down, her ass right at the end and her legs on either side of me. “I’m going to perform a very technical procedure,” I said, rubbing her outer thighs and then slowly spreading her legs more open. “Something I’m not supposed to do just on a whim in here.”

“Yeah?” she grinned at me. “Is it a big secret among massage people?”

“Oh, not that big a secret,” I said. “But when done right it can be dangerous. Maybe even deadly.”

“Doesn’t sound too mellow to me,” Marissa said.

I leaned over her and kissed her gently, and soon we were making out. She brought her hands up and held onto me, keeping me there as she fed me her tongue and then sucked on mine playfully.

“Ready to be the All You Can Eat Buffet?” I asked her quietly.

She snorted and pulled away from me a little. “Please do not call me a buffet,” she laughed.

“Alright, breadstick,” I said.

She rolled her eyes and I kissed her again as we were both smiling. Then I started kissing my way down her chest and stomach towards her pussy.

We had a good forty minutes left in the hour she’d told me she had, and I intended to spend every goddamn minute helping her relax.

- - - - -

The photo came in late at night and I was already in bed. I groaned, wincing a little as I thumbed my phone on and unlocked it and the light blasted in my face. The text notification was all the warning I had and then I was looking at a picture of Marissa from the night we’d spent together. Her hair was messy and she looked like she’d been fucked good - her bare breasts were also covered in my cum.

‘Still owed you this one ;),’ she’d texted with it.

Then another picture came in and if it wasn’t so lewd I would have almost found it artistic. It was Marissa, naked, squatting and leaning back with a light on overhead casting her in stark light and shadow. Her knees were spread and she was up on the balls of her feet. And she had a clear plastic or glass dildo currently pumping into her pussy. Her jaw dropped and I could practically hear the sound of her moaning an orgasm.

‘This one is to say thanks for today.’

“Well,” I said to myself. “I’m hard.”

I was trying to decide what to send back to her when I got another text, but it wasn’t from her.

‘I got a little messy thinking of you :P,’ Eden had sent, along with a picture of her laying on her stomach, her legs spread enough to see her pussy lips were creamy and the sheets under her had a big wet spot.

“Fuuuck,” I groaned.

- - - - -

“OK, I need you to not be weird about this,” Jessica said.

It was the middle of the afternoon on a Tuesday, so I wasn’t quite sure what I could be weird about. “That tells me almost nothing about what you’re worried about,” I said.

The lobby area of the spa was as serene as usual, the lighting toned down a bit and the nature sounds piped in through the hidden speakers. There had apparently been a big group that had gone into the saunas a half hour before so it was hard to say how long that would remain true.

“Your next client is my Mom,” Jessica said. “She wasn’t sure how to contact you or whatever, and she wants to talk to you about what happened on the weekend.”

“Um, alright,” I said. “You could have just given her my number or something. Or she could have dropped by, she doesn’t need to be a client.”

“I think this gives her an excuse for her to give you a big tip or something,” Jess said. “She comes from… Well, let’s just say she comes from money and that’s how her family says thank you.”

“Alright,” I sighed. “But you’re still taking your cut, coming from family or not.”

Jess rolled her eyes. “Yeah, right,” she said. “She’s tipping you for saving my life, I’m not doing that.”

“You’re a good kid, Jess,” I said. “I’ll make you a deal - if she tips through the system, then you get your cut. If she hands me an envelope of cash or something, I’ll keep it to myself.”

“Deal,” she said.

Her mother showed up a couple minutes later and looked a lot more put together than the last time I’d seen her - she was dressed in a nice floral print dress that ended around her mid-thigh and had three-quarter sleeves and a wide pink belt. It was girly and fun, but also mature. The thing that really stood out to me was her hair though - when she’d shown up at the ER that night it had been pulled back messily and she’d been in a panicked state. Now she’d clearly taken the time to not only do her makeup to an attractive level, but she’d also gotten her hair done and it showed off a cascading, brunette volume with soft golden highlights.

“Trevor,” she said warmly, walking right up to us. “Please, can I give you a hug? I just- ugh, thank you.”

I opened my arms and she hugged me almost as tightly as her daughter had the previous morning. They were of similar height, and now I knew where Jess got her fierce embraces from.

“Mrs-” I started, then stopped and chuckled as we separated. “I’m sorry, but you’re still ‘Jess’s Mom’ to me.”

“Violet,” she said. “Violet Darrington. And that’s OK, Jess hasn’t exactly told me your last name either.”

“Trevor Brantford,” I said, holding out my hand.

She shook it and gave me a look. “Are you Tina’s son?”

I cleared my throat a little. “Ah, yes,” I said.

“Hmm,” she hummed, giving me another thoughtful look, then glanced at her daughter. “Everything set for Trevor to take care of me, baby?”

“Maybe not ‘baby’ at work, Mom?” Jess groaned.

“You’ll be my baby forever,” Violet smirked at her daughter.

“Yes, you should be all set,” Jess sighed, then looked at me. “Please, for the love of God, take her back so I don’t get embarrassed anymore.”

“So,” I said, offering Violet my arm to escort her. “I think I would love to hear all your embarrassing stories about Jess.”

“Wait, no!” Jess called, making the two of us laugh.

I led Violet Darrington back to my work room and she looked around curiously as I closed the door and gestured for her to take a seat on the massage table while I pulled around my chair. “So, Mrs Darrington,” I said. “Have you ever had a massage here or at another facility?”

“It happens in here?” she asked, not answering my question. “With a glass wall out into the hallway?”

“In here, yes,” I said, standing and moving the switch near the door. “But for your privacy, Greenmeadow has these fantastic walls.” I flipped the switch and the glass turned opaque.

“Wow,” she said. Then blew out a breath. I flipped the switch again, turning the glass clear again. “Actually,” she said. “Could you just leave it blocked?”

I frowned a little but nodded. “If that’s what you’re comfortable with.” I flipped the wall back to opaque and went and took my seat again. “So, have you had a massage before, Mrs Darrington?”

“No, and that’s not why I’m here, Trevor. And please call me Violet.”

“Alright, Violet,” I said. It wasn’t an uncommon request from the clients to use their first name. I made a small note on my record sheet for her, underlining her first name. “But I am a masseur and you’re in my office. If this is about Friday night-”

“It is,” she said quickly, and I got the feeling she was working herself up to… something. I wasn’t about to get served or something, was I? “Look, Trevor, I’m extremely grateful for what you did for Jessica. You went out of your way to help a way-too-drunk teenager, and you saved her life doing it. You saved my baby's life.”

“Like I told you that night,” I said. “Jess is a good kid and a good coworker. I like to think I would have helped any of the girls she’d come with if they were in the same boat, but Jess knew to come to me and Marissa when she felt off. She did half the work for me.”

“Still,” Violet said, shaking her head. “You proved that you’re a good man, Trevor. My boyfriend didn’t even want to get out of bed when you called.”

“Uh, I’m sorry,” I said. “About him, and I, uh, guess it’s not ‘Mrs’ then.”

She smirked a little. “Technically I’m still ‘Mrs Darrington,” she said. “But my husband died several years ago.”

“I’m sorry again,” I said.

“Don’t be,” Violet shook her head. “He was a pompous ass and didn’t care about me or Jessica one bit. Cared more about his fast sports cars and racing them all over the world, and that’s what took him. I sold every single one of them as soon as I could, and mine and Jess’s lives barely changed at all. But that’s all neither here nor there. Are you and Marissa together?”

It was a bit of a switch in the topic that I wasn’t expecting, but it only took me a moment to blink and pivot. “No,” I said. “We’re not officially dating or anything. Just friends right now.”

Violet took another breath and then nodded. “I want to give you a reward for saving my daughter’s life,” she said. “And-” she held up a hand to stop my reassurance she didn’t need to. “-I’m going to ask that you don’t tell Jess about the nature of the reward.”

“I’m not… sure what you mean,” I said with a frown.

She stood up from the table and quickly undid the wide belt on her dress, then let it separate and fall off her shoulders as she shrugged her arms out. Her breasts were small and perky, and her warmly tanned skin looked sleek and well-toned. She hadn’t been wearing a bra and her nipples were already hard. “A hero deserves some spoils,” she said. “And my daughter’s life is worth more than cash. I thought maybe you’d like a blowjob, or more, once a week? At least until you’re seeing someone and have someone closer to your own age to get stress relief from instead of an old lady like me.”

I had to work my jaw a few times before I could actually say anything. “Um, OK, um,” I stammered. “First off, you might be older than me, Violet, but you’re not old. I get old through here on a daily basis, and a lot less gorgeous women like you. Second, I thought you had a boyfriend?”

She sighed and shook her head, leaning down and taking my hand and lifting it to her breast. I couldn’t help naturally cupping it and starting to massage it. “Mmm,” she moaned softly. “I should have been more specific. My ex-boyfriend didn’t want to get out of bed. So he’s no longer welcome anywhere near it.”

I took another breath, feeling her tit and groaning softly. “Not to sound unthankful, but this really isn’t necessary,” I said.

“And that, Trevor,” she replied, leaning down to grab my other hand and bring it up to her free tit. “Is exactly why I feel like this is exactly what you deserve.” She slipped down to her knees, spreading them so she could scooch closer, and then reached for my belt and zipper but hesitated. “If you’re actually telling me no, I understand and will stop. I don’t want you to think you have to let me do this because I’m a Club client or something. This isn’t something I’ve ever done before.”

I sighed, pulling my hands from her breasts. “Violet,” I said, giving in. “As long as you don’t feel like you need to do this, then everything is consensual.”

She grinned a little and went to work getting my cock out. I had to lift my hips to let her pull off my pants, and my briefs quickly followed which led to her cooing in respect. “Oooh, Trevor,” she hummed. “That’s a nice-looking cock.”

“Grew it myself,” I chuckled, which made her smile and roll her eyes a lot like her daughter did.

Violet went to work, stroking me with one hand and getting her mouth around the head quickly. We only had a thirty-minute appointment and had already burned about five talking. She was energetic in her sucking, working her lips up and down my cock quickly and humming little moans before pulling off and giving the underside of my cock a long, broad-tongued lick. Then she was right back to sucking me off. She was grinning with her eyes as she looked up at me every once in a while. She even took my one hand and brought it to the side of her head, encouraging me to run my fingers through her hair and direct her speed a bit. 

Her hair was luscious and thick, more so than either of my other two recent partners, and I luxuriated in weaving my fingers through the soft waves and gripping her by the scalp, feeling powerful as I slowed her down or sped her up. She seemed to enjoy every moment of it too, flashing me hungry looks.

When she pulled off again she was grinning, the tip resting on her bottom lip. “This,” she said. “Is a fucking nice cock. I think I’m going to have fun with this. How soundproof are the rooms?”

“Enough so that you can’t hear people groaning in pain when getting a deep tissue massage on a bad tension point,” I said.

“I don’t know how loud that is,” she chuckled.

“As long as neither of us are screaming then we should be good,” I said.

“Then next week you’re fucking me,” Violet said. “I’d hop on this dick right now but I’m on my period, so I’ll just make love to you with my mouth.”

I groaned at the idea of fucking Jessica’s Mom. It was so wrong but so right. She was smoking hot, and even if she didn’t have tits to rival Eden, let alone Marissa, from what I’d seen she had a nice ass and her legs and torso were really toned.

By the time I was about to pop, I thought I might have been able to have fallen in love with Violet Darrington. She might have been closer to two decades older than me than she was one, but just the way she looked up at me with those eyes and seemed to love sucking my cock… Phew.

“Come in my mouth,” she panted quietly, one corner of her lip curling up in a pleased smirk as she stroked me quickly with both hands and opened her mouth. “Come right in my mouth, my hero. I want to drink it all down.”

“Fffuuck,” I groaned. “God, fuck, Violet.”

She stuck her tongue out, teasing the bottom ridge of my cock head, and that acted like a launch button as my cum surged out of my balls and started loosing strands that hit the roof of her mouth as we both moaned. She took every rope of cum as she kept teasing that spot on the underside of my cock, her eyes locked with mine and showing me sheer pleasure and joy at having worked me up and then gotten me to blast off.

When I was done I was seeing spots a little and had to sit done, which made VIolet smile to herself as she made a show of swallowing every drop of the big load I’d just fed her. Then she stood up and sat on my lap, pulling my face down to her tits. I sucked one nipple between my lips and she moaned.

“Fuck, Trevor,” she groaned. “I can tell you’re going to be an amazing fuck.”

“I feel like I’m just going to be trying to keep up,” I chuckled, then switched to the other nipple.

“Maybe,” she grinned. “But only because I haven’t been fucked properly since, like, college.”

We were running out of time and after a few more kisses to her breasts we had to stand up and she got her dress back on pproperly, then fixed her hair in the little mirror that was on one wall.

“I’d kiss you, but I’ve got cum breath,” she said. “I’ll have to remember to do that next week.”

“Violet, that was- Fuck. Amazing. But seriously, you don’t need to thank me like this every week.”

She shot me a look. “When you tell me you’ve found someone and need to stop, I’ll stop,” she said. “Until then, just assume that whatever I do with you is what I want to be doing. OK?”

“Alright,” I agreed.

She got close and hugged me again, but pulled my hands around behind her and onto her ass which was big and firm. “It’s good to be held by a man,” she murmured, hugging me tightly.

“It’s good to be held by a woman like you,” I said.

She pulled back with a grin and winked at me. “I’ll make sure Jess has me scheduled regularly,” she said. “You might want to get yourself together too. You look like you just got a damn good blowjob.”

I laughed and checked myself in the mirror. She was right.