Masseur and the MILF 2; Part 3 (Alpha)

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Opening my front door, I couldn’t stop myself from grabbing Eden and pulling her into my arms in a kiss that ended up with her back pressed to the doorframe. She was dressed in a cute green top that hugged her moderate bust and tight capri pants, her hair back in a little spray of a ponytail. She almost looked like a college coed princess, except one of the super hot ones from a movie that had cast people clearly not the right age to be the ‘sexy’ background characters. 

I pulled her leg up with my hand on her thigh and she moaned sexily into my lips as we made out in the doorway. When we finally pulled away I hefted her up by her butt and her tinkling laugh rang in my ears as I carried her inside and kicked my front door shut behind us. My place wasn’t big, so it was only a half dozen steps to the couch where I lowered her down to her back. She pulled me back up to kiss her again, her hands scooping under my shirt to rub my chest as I stroked her sides and hips.

“Trev, honey,” she finally gasped, breaking our liplock.

“Mhmm?” I hummed, kissing my way along her jaw and then down her neck.

“I told you I had a surprise,” she said, her voice hitching sexily at the feel of my lips on her. “But there was a scheduling issue so it’s just me today, if that’s OK?”

I lifted back up to look her in the eyes. “Eden,” I said. “How could you ever not be enough?”

Her eyes softened a little as she smiled warmly. “You’d be surprised, honey,” she said. “Some people can be real assholes.”

With a shake of my head, I sighed and then kissed her again sweetly.

“But I have another problem,” she said once that kiss ended.

“What is it?” I asked.

“I got looped into helping my sister-in-law with some family stuff,” she winced. “And I couldn’t exactly tell her why I wasn’t available on a Tuesday night that I also don’t have my kiddo. So we’ve only got about an hour before I need to go.”

“Forty-five minutes,” I said.

“What?” she asked, confused.

“You’ll need fifteen minutes to shower off the sex smell and fix your makeup,” I pointed out. “Unless you already accounted for that.”

“I hadn’t,” she chuckled, then gave me a firm peck. “You are way too good to me. Now how about we get me naked so we can see how close to getting my legs behind my head we can get?”

Getting naked with Eden didn’t take long at all, and getting hard for her even less time than that. It turned out that she could get one leg folded all the way back and hooked behind her shoulder, but the other one couldn’t quite get there. Not that it mattered so much - I was still able to fuck her hard and fast enough that we were both sweating and sucking air.

She came twice, pretzeled up like that, the first one more explosive than the first. Her moans were heavenly, her joyous laughter almost orgasmic just by itself. I abused her nipples a little, pinching and tugging on them and making her pant with her cute little tongue teasing her lower lip. There were also short breaks so I could smush my face against her wet, sodden pussy and slurp at her juices, getting her taste all over my lips and cheeks as I drove my tongue into her, and then rose back up to let her lick it off of me as I went back to pummeling her with my cock.

I almost came, pulling out with just a minute or two to spare, and we took a quick break before Eden had me sit on the couch and she knelt between my legs and sucked me off. She teased me, whispering sweet little compliments that ranged from how she found me attractive physically, to how I made her feel, and even to how she admired me for how well I was handling starting my new life.

A woman like Eden admired me.

Then she climbed up and straddled my cock, slipping back down onto it as I cupped her ass cheeks.

“Did she ride you this good?” Eden suddenly asked me.

“What-?” I blinked.

“Marissa,” Eden clarified. “Actually, I should have said ‘Did she ride you at least this good?’ Because she better not be holding back on you.”

“She was… proficient,” I chuckled.

“Good,” Eden laughed.

“You really don’t care that I’m fucking her, too?” I asked.

“Did you tell her about me?” Eden asked.

“I mentioned that I knew a MILF,” I said. “And that I could maybe organise a threesome. She didn’t seem turned off by that at all.”

“A threesome, huh?” Eden smirked. “Every guy’s fantasy.”

“You are every guy’s fantasy,” I said.

“And so is Marissa.”

“Her too,” I shrugged. “You know I wouldn’t demand it, right?”

“You know I’d love it if you did, because I know you wouldn’t actually be demanding it,” she pointed out.

“Have a threesome with me and Marissa,” I said, putting a little force into it.

“I will,” Eden moaned. “God, that sounds like a blast.”

I sighed then. “There’s something else,” I said.

She slowed her up-and-down motion on my cock, her hands lightening on my shoulders since she didn’t need to leverage so much. “Ominous,” she said, raising an eyebrow.

“I… had an encounter,” I said.

“With who?”

“Another…  MILF,” I said.

Eden frowned. “Rachel wasn’t booked with you today, was she?”

“No.”

Now both of her eyebrows rose. “So someone else started hitting on you?”

“It was a little more complicated than that,” I said. “And if I explain anything more I would be giving away her identity, and that wouldn’t be fair. I just need to know if you’re not OK with it.”

“What did she do?”

“Oral,” I said. “On me. Next time she said she wants the full package.”

“Was she good?”

“Yeah,” I said.

“Is she actually a Mom you want to Fuck?” Eden smirked.

I hesitated a moment, but there was no denying that Jessica’s Mom was hot. “Yeah,” I said.

“And you’re going to tell Marissa,” Eden guessed. “And you’ll tell her about us. Without names.”

“It would only be right, right?”

She sighed, shaking her head and putting her hands on my cheeks, leaning in to kiss me as she started to grind on my cock. When she pulled away she was smiling a little. “If you were my boyfriend, or my husband, and you just started to cheat on me or something, it would be a problem. But this isn’t that - I’m your little MILF slut, and you’re being conscientious of me every step of the way. As long as you’re guarding your heart, Trev, then I’m fine with it.”

We kissed for a long time, making out again as she used her hips to stir my cock inside her, and then she dropped her chin to my shoulder and panted in my ear as she rose to another orgasm. I teased her asshole with one finger, and she sucked on my earlobe.

My groan helped her hold off for another minute, letting her know I was close too, and we came at the same time as we held each other.

“God, that was a big one,” Eden moaned softly as she sat up and ran her fingers through her hair. At some point, her hair tie had come out. 

“It was,” I chuckled.

“No, I mean your load,” she said. “I feel like I drank an entire Big Gulp or something. I won’t be surprised if I hear sloshing sounds while I’m driving home.”

I laughed, kissing her cleavage, then looked up into her eyes. “I love you, Eden,” I said.

“I love you too, Trev,” she grinned and gave me a wink.

I was inside her. We were in the sex. No clarification needed.

- - - - -

‘Hey.’

The text from Marissa was pretty much the vaguest possible.

‘What’s up?’ I asked. It was eight at night and I’d just sat down with a dinner of homemade chicken strips, planning on smashing through some show on Netflix that I hadn’t discovered yet. Thursday nights used to be a party night back when I’d been in the massage program, but now that I worked early Friday morning I’d pretty much given that idea up. Particularly considering my home town didn’t exactly have a bustling nightlife beyond a few bars.

‘I should be finished here in half an hour,’ Marissa texted back. ‘Want to come to my place and fuck? Can’t do more than that.’

I pursed my lips. First Eden, and now Marissa. Was I mad that I was only getting booty calls? Maybe I would, at some point, but for now the answer was Not At All.

‘Sure,’ I texted back. ‘See you soon.’

I checked the time. Half an hour until she was done shift, another ten minutes to get out of there, ten minutes for her to drive home, and ten minutes to give her time to change or get ready. That meant I needed to be at her apartment in a little under an hour. I had time to eat, watch half an hour of something, and grab a quick shower myself so I was showing up scrubbed clean and smelling nice.

The first bite of my chicken strip had a nice crunch to it and I groaned, high-fiving myself. Life was good.

- - - - -

“I am so sorry,” Marissa said as I got out of my car.

“It’s OK, Izzie,” I said.

“No, it’s not,” she said. “You must have been waiting here over an hour.”

“Half an hour,” I shrugged.

“It was fucking Cindy,” Marissa grunted, taking my hand and leading me towards her building. “She fucking batted her eyelashes at Walt and convinced him to let her off early even though I was working a fucking double to cover that stupid wedding.”

“What made the wedding stupid?” I asked with a chuckle.

She glanced back at me with a smirk. “Awful colour scheme, the bride was practically orange, she had so much fake tan on, and the mother-of-the-Groom was having a breakdown over the fact that the cake was chocolate even though that’s what the Groom ordered, and that the DJ wouldn’t play her wedding song. But that’s all beside the point because fuck Cindy.”

“Yeah, fuck her,” I said supportively. “Who is Cindy?”

Marissa snorted and shook her head, pulling me down into a kiss. She was still mostly dressed in her waiter outfit for working the event catering at the club, a white dress shirt and black slacks with a black bowtie hanging loose from the collar. She’d undone the shirt most of the way, revealing a white tank top undershirt ringed with some sweat, and her long blonde hair was pulled to the back of her head messily with a chunky hair clip.

We made it to her apartment and she let me in. “Can I get you a drink?” she offered.

“You, sit,” I said, directing her to the couch. “You served dozens of people tonight. I can get you a drink.”

“It’s my place,” she said, but let me guide her.

“You need to get off your feet,” I said.

“I probably stink,” she said. “I need a shower.”

“I can live with it,” I said, heading for the kitchen. “Wine or beer?”

“Wine, the rose in the fridge. Please,” she called.

I found the rose, and a wine glass, and poured her a decent glass before coming back out. I’d been expecting that she might have taken off her white dress shirt, and kicked off her shoes. Maybe let her hair down. I hadn’t expected to find her completely, gloriously naked and heading straight for me.

“This, I need,” she said, taking the glass from my hand and drinking about half of it in one go. “You,” she then said, putting a hand on my chest. “Deserve at least a nice-smelling booty call here. So come fuck me in the shower.”

It turned out that Marissa and I, unlike my experiments with Eden, didn’t have great chemistry for shower sex. It wasn’t that we weren’t willing, or that running my hands all over her curvy, soapy body and especially her tits wasn’t amazing, but Marissa was just… short. And I was relatively tall. And without a bath mat at the bottom of the tub, neither of us felt confident for me to pick her up and pound her against the wall without slipping and cracking both our heads open.

That’s how we ended up in her bedroom, Marissa lying flat on her stomach with a pillow under her head and another under her stomach so there was room for her tits, while I cradled her from above and fucked her as she worked her hips to hump back at me.

“God, fuck, Trevor,” she groaned. “Fuck me hard.”

“Better, same, or worse than the machine?” I chuckled, nuzzling into the crook of her neck.

“Ye-ee-ees,” she groaned, making me laugh. Then she put a hand on my hips, slowing and then stilling my thrusts, and she had me lay on the bed so she could ride me with her tits dangling enticingly over my chest. “Play with them,” she begged me. “Roughly.”

I did just that, finding her nipples and teasing them, then squeezing and massaging her heavy breasts. She was wearing her glasses and we looked through those little glass portals at each other.

“Just so you know,” she said, grinding on my cock. “I feel a little guilty about this being just a booty call. I want to do more, I just can’t. I have work early tomorrow.”

“I know,” I said.

“No, seriously,” she said. “I- Look. Friday, all of Friday, was really fun. And you’ve sort of proven you’re not a fucking weirdo or clingy. I want to spend more time with you. Maybe even do the dating thing. I’m just so fucking busy that it doesn’t feel fair. Like, I’m completely booked this weekend already. I’m booked every night until next Saturday.”

“So let’s hang out on Saturday,” I said.

“I have the morning shift at Greenmeadow. Carts.”

“So after that,” I chuckled, letting my hands fall from her tits to hold her hips. Why was it that both Eden and Marissa wanted to ride me to have a conversation? “Marissa, I know you’re busy. That’s OK. I would kinda, maybe want to do the dating thing with you too, but at your speed.”

“My speed seems to be meet, fuck, then date,” she chuckled ruefully. “Fuck, that feels good.”

I’d slid a thumb down to rub just above her clit. “Next Saturday,” I said again. “We’ll do something relaxing. Do you want to spend time indoors or outdoors after working carts?”

“Indoors,” she said. “And quiet.”

“OK,” I said. “I’ll figure something out. And I’ll manage dinner.”

“You’re sure?” she asked. “I might… call you for another one of these. Or two.”

“Oh, no, whatever will I do?” I asked in a fake dramatic voice. “Called by a gorgeous, smart, ambitious woman to fulfil her sexual needs?”

“Ass,” she chuckled, clapping both hands on my chest lightly.

“Well, that’s an offer,” I grinned, sliding my hands back to grab her butt.

“Maybe next Saturday,” she smirked at me again. “If you’re good.”

I growled, massaging her ass cheeks.

“You’re not just a good fuck,” she said to me like she needed to make sure I knew it.

“Neither are you,” I said.

“Are you fucking that MILF you mentioned maybe doing a threesome with?” she asked.

I swallowed but didn’t back down, nodding. “I am,” I said. “A little like what we’re talking about. Some emotional connection, but not actually talking about dating. Her life is mostly full already, and we care about each other but it can’t really be more than that.” I kept steady eye contact with her. “Is that a problem for you and us maybe, kinda dating?”

Marissa bit the corner of her lip, considering the question. “I… Not for now,” she said. “And maybe not for a long while? Like, if we do start dating, with dates being every couple of weeks or something, then that’s only like six dates over the rest of the summer. Then I’m in school again for my final year and I’ll be working a little less, but I’ll still be volunteering and finishing my thesis. Maybe you having something else going on… makes sense.”

“Hey,” I said, taking her waist in both my hands and stilling her. “Seriously, Marissa. If it’s a problem, it’s something I’ll work to figure out. She already knows I’m seeing you, and is encouraging me to actually get into a relationship with you, and she knows I’m telling you about her.”

“She is,” Marissa said, half a question.

“She is,” I nodded. “I- It’s complicated. I think she’d rather see me happy with you than for our thing to make us not a possibility.”

Marissa sighed a huff, blinking. “I think I need to meet her,” she said. “Then I’d know.”

“Um, OK,” I said. “I’ll figure something out.”

“No, I mean- I think the threesome needs to happen,” Marissa said. “I think, if we have that experience, and I feel like I can trust her, then you and her wouldn’t be a problem for me at all.”

“O-Kay,” I said, drawing it out. “Alright. Then I’ll figure that out.

“OK,” she nodded.

We sat there for a moment.

“You’re fucking someone else other than that, aren’t you,” she guessed. I must have given something away in my expression.

“I’ve been… approached,” I winced. “And got some oral.”

“At work,” Marissa sighed.

“Yeah,” I said.

“Some client princess?” Marissa guessed. “Fuck, was it that Paula Polterri girl? She’s such a fucking skank-”

“No, it wasn’t,” I said. “It was, uh… Well, I’m not supposed to say.”

“If it wasn’t a princess, then it was a Club MILF,” Marissa said, chewing on the inside of her lip as her brow furrowed. The fact that my cock was still buried deep inside her, and she was squeezing it with her Kegel muscles, was hopefully a good sign.

“Marissa,” I sighed. “It would be rude-”

“Jessica’s Mom,” Marissa guessed, then snorted - my expression gave me away again. “Nailed it. Does Jess know?”

“No,” I said. “And she’s not going to. Violet said she wanted to reward me with something other than cash, so she booked an appointment and gave me a blowjob. But she promised more, she wants to fuck, and said she would every week until I told her I needed to stop.”

Marissa nodded slowly, then raised an eyebrow. “Hold on, why the fuck are you getting a reward and I’m not?”

I shrugged and lifted my hands. “I… don’t know? Maybe I’m just easier to find? And I work with Jessica directly.”

She snorted and chuckled. “Whatever,” she said. “Violet Darrington is hot, and if there isn’t even an emotional thing then all I asked is you don’t get fucking fired.”

“Really?” I asked.

“Trevor, are you really going to question this decision?” Marissa asked, leaning down and squashing her tits against my chest as she looked at me from up close.

“No,” I said. “No, I guess I’m not.”

“Good,” Marissa said. “Then roll me over and pound my cunt until I orgasm so hard I pass out. I need that kind of sleep. If you don’t pop before then you can fuck my titties and cum all over my face.”

“That’s nasty,” I snorted.

“That’s me betting I can make you come before I get there,” Marissa smiled wickedly.

I sighed and wrapped my arms around her, rolling us over so I was on top. “Just remember, when you’re at the diner tomorrow morning and walking funny, you asked for this.”

“Do your worst,” she said, beaming a smile at me as she took my hands in hers and squeezed my fingers. “Make me fucking f-feeeel- Oh, fuckballs, yes!”

- - - - -

“Trevor,” she said. “Trevor, can I speak to you for a moment?”

It was that tone. The one that I’d heard a hundred times. Maybe thousands. The one that made me clench my jaw on one side and my fingers twitch just a little.

“Yes, Mother?” I answered, turning to see her.

It was early enough that I would never have thought to look for her in the Greenmeadow parking lot. But then, I worked a day job and she hadn’t worked a day in her life. It was tough, looking back at my childhood and teenage years with the perspective of having seen a bit more of the world, to really hold all of my frustrations with her. I’d grown up with the same silver spoon shoved down my throat that she had, after all. The thing was that I choked on it.

She’d gotten a new car, based on the Mercedes she was walking from, but that wasn’t very surprising. Neither was the fact that she was parked in a handicap spot - she’d gotten tickets for that multiple times over the years and never seemed to care, always having an excuse. My mother was dressed in a tight white skirt that went down to her knees and a blouse that billowed stylishly, along with a large pair of sunglasses covering her eyes and her hair perfectly styled even before any stylist could have been open. She knew how to take care of herself in the beauty department, which was good because she’d never been much of a homemaker.

“Trevor, dear, it’s so good to see you,” she said, coming over and wrapping her arms around me. I hugged her back. “I wish you would come by the house.”

I suppressed my sigh. “You and I both know how that would end up,” I said. “It’s nice to see you.”

“Oh, my baby,” Mother said, pinching my cheek lightly and tutting. “You will always be welcome at home. Never mind your Father.”

She and I both knew that wasn’t really the case.

“I need to get into work,” I said. “Can we cut to it?”

“It’s about this work, dear,” Mother said. “People are starting to ask… questions. Your Father is getting agitated that his friends, and their wives, are talking about you.”

“Talking about me how?” I asked. “Are they saying I’m doing a bad job? That I’m doing something wrong?”

“No, dear, no. Just… talking.”

I sighed. “So Father, who disapproves of my career path, doesn’t like the fact that I’m doing a good job?”

She frowned. This clearly wasn’t going the way she thought it should.

“Mother, what was the best-case scenario for coming out here this morning?” I asked. “If you were to get in your car and think ‘That all worked out perfectly,’ what would it look like?”

“Well, you would come home, obviously,” Mother said. She really did love him, it was just how she showed it and acted on it that was the problem. “And you could start working at your Father’s company. He’d have to start you right at the bottom, but he’d pay you well and you could work your way up quickly, and he could talk about how you wanted to do it that way to earn your place. And then we could find you an appropriate girlfriend, and you could get married in a couple of years…” She trailed off at the look on my face.

“I’ve got my own career,” I said. “I’ve got my own home. He doesn’t get to control me or decide how I live my life. And neither do you, Mother. I’ve been happy, the last couple of years while I was away. And I’m happy now here, building my life. I get to pick what that life looks like. Especially who I date.”

“Callie Peterson is single,” she said. A hail mary pass if I’d ever seen one. She knew I’d crushed on Callie back in middle school, and Callie’s ‘awkward phase’ had seen her modelling in Teen Vogue a couple of times and she’d only gotten prettier from there.

“Callie Peterson hasn’t even shown an ounce of interest in me, and I doubt she would start now,” I said. “And Doug Peterson is even more controlling than Father. I wouldn’t be surprised if a guy has to sign a prenup and submit three years of financial statements just to date Callie. Hell, he’s probably shopping around for an arranged marriage for her and requires six generations of pedigree and to squeeze the guy’s balls just to make sure they’re healthy and so he can show dominance.”

The look on my Mother’s face was a little priceless.

“I love you, Mother,” I said. “And if you ever want to grab dinner, I’d be happy to meet you somewhere. Just the two of us. I’m sorry I can’t be the perfect robot son Father wants.” I left it unsaid that I disappointed her at times as well.

“Oh, Trevor,” she sighed, hugging me again. I hugged her back after a moment.

“I gotta go, Mother,” I said.

“OK,” she said. “OK. Um, Violet Darington told me you were a lifesaver, but didn’t expand. Whatever you’re doing… just know I’m thinking of you.”

I hugged her a little tighter. “Thanks, Mom,” I whispered.

Heading into the staff entrance, I surreptitiously wiped at my eyes under my sunglasses and left them on as I walked the back corridors. I’d forgotten how much it hurt to feel like I was never enough.

- - - - -

“Why do you look like shit?” Marissa asked as I sat down at our usual lunch table. I worked the same schedule every day but she was constantly working different ones, yet somehow she always had the same lunch hour as I did.

“Rough morning,” I said, waving it off like it was nothing. The morning really hadn’t been that bad. Mostly the usual stint of old folks with their array of aches. One of the ‘club princesses’ had come in as well, Jessica making goofy eyes at me as I escorted her back. The girl had been blushing up a storm throughout the intro interview and had made one awkward joke that might have been flirting or might have just been trying to break the tension. It hadn’t worked, but she’d still left with a smile on her face after the basic massage.

“Someone get pissed off?” Marissa asked. “Kick you in the face when you push their pressure points?”

“No,” I smirked a little. “Nothing like that.”

She leaned in close, dropping her voice to a whisper. “More MILFS making passes at you, but the ugly ones?”

I snorted softly and shook my head. “No, not that either.”

“Talk to me Trev,” Marissa said, patting my thigh under the table as she looked at me in concern.

I groaned and stretched, blowing out my breath in a long stream as I looked up at the ceiling and then back at my food. “I had a run-in with my Mother,” I said.

“Oh,” Marissa replied, clearly unsure about the obviously missing context around a statement like that.

“Same shit, different year,” I said.

“That bad?”

I shrugged. “Not as bad as when I left. And not nearly as bad as my Father. Just… yeah.”

“Fuck,” Marissa sighed. Her hand hadn’t left my thigh and she gave it a squeeze. “I don’t know if I made it clear, but I don’t exactly have the greatest relationship with my parents either.”

“I put two and two together. Moving out right at 18, working your ass off-”

“I like to think I have a pretty nice ass,” she joked.

That got another smirk out of me, and our eyes met so she knew I wanted to say something dirty but held back.

“Serious not-serious question,” Marissa said. “If you got invited to a wedding and needed to take a +1, and I went with you, what would your parents think?”

“I wouldn’t care,” I said.

She gave me a look. “But what would they think?”

I shook my head. “I’m not really sure, but they’d be polite to your face and then constantly ask me questions like ‘Are you really sure she’s right for you?’ behind your back and that would start fights between me and them.”

“So basically the exact same shit my parents would say, but based on wealth and not culture,” she said.

I blinked, looking at her again. Marissa was pretty damn white. I was also pretty damn white.

“What… culture…?”

“Poor white trash,” she chuckled. “If I brought you home, they’d congratulate me on successfully gold-digging and tell me to take you for all you’re worth. And then they’d try and set me up with one of the going-nowhere-fast assholes they know because they want everyone to be as miserable as them.”

“Well, shit,” I said.

“Yeah.”

We ate in silence for a couple of minutes, absorbing the conversation, and then I got a text and quickly turned my phone back over.

“What was that?” Marissa asked.

“It was…” I said, then glanced around to make sure no one else in the breakroom was listening. “Someone making plans. For tomorrow.”

“Like… plans plans?” Marissa asked, raising her eyebrows and blushing a little.

“Do you want me to tell you stuff like that?”

She hesitated and then nodded.

“Plans plans,” I said. “And she keeps promising a surprise, so I think it might be with someone else.”

Marissa blew out a breath. “Can you do me a favour?”

“Keep my trap shut?”

“No,” she said. “Tomorrow night, call me. At like midnight. I should be home from the shelter by then. And I want you to tell me what happens. Graphically.”

“Really?”

She nodded. “Really.”

“OK,” I said.

“OK,” she agreed. We were both blushing a little and went back to our food.