Masseur and the MILF

She kissed me, pressing her neck down on my hand to do it, then pulled back. "I'm not asking you to meet my son," she said. "And we're not going to start dating. You're right I don't have the time for that. But I want to keep seeing you. I want to keep making you feel good, and I want to keep being your little MILF whore. It's more than sex."

"OK," I said and took my hands from her neck and hair and palmed her ass with both of them. "Then next time, I'm taking your ass and making you my three-hole MILF fuckpet."

She moaned and panted happily.

We fell asleep like that after I blew my last load of the evening into her, my cock still inside her.

* * * * * * *

"You should just ask Marissa out," Jessica said.

It was Tuesday morning. Eden and I had slept in on Sunday and fucked the rest of the morning away, but her son was supposed to get dropped off at 2pm by her ex and she wanted to get some cleaning done so I'd left her with a kiss, my cum dripping off her tits, at noon. I'd collapsed back at my place, exhausted, but the long sleep had left me ready for Monday.

And Monday had been like I'd started working at an entirely new Spa. Sure, I still had the occasional older client, but what Jessica had said had been true - my week looked like it had booked up with Trophy Wives and Club Daughters.

Thankfully, I think, nothing untoward or explicit happened. There was some light flirting, but no one got as forward as Rachel Killian had, let alone Eden; the weirdest part of it all was that all of them were sonice to me. Everything I could remember about the Greenmeadow membership was that it was snooty, snotty and could be quite rude. But these women were downright... pleasant. And I could think of only one reason - they were all, in the back of their minds, considering the idea of getting a piece of me.

That, right there, was a weird feeling and I dreaded the day someone made a move I had to turn down.

"Why would I ask her out?" I replied to Jessica. We were waiting in the lobby for my next appointment, a Club daughter who was running five minutes late already.

"Because you guys flirt every lunch," Jessica said. "Everyone is talking about it. And if you have a girlfriend then some of the horny bitches might back off." Despite thinking it was funny how popular I was with bookings when I first got there, by week two Jessica was getting annoyed with the overflow of women trying to squeeze in spots earlier than two weeks out by that point.

"Marissa isn't interested in dating," I told Jessica. "She was upfront about that, and I respect it."

"But you would though," Jessica guessed. "If she wanted to."

"Sure," I shrugged. "She's a great girl, and so far a decent friend."

"Yeah, I'm those things too," she said.

"And you're also a seventeen-year-old lesbian," I countered.

"Fine, fine," she sighed dramatically. "But I still think you should ask her out. She said that weeks ago, she might have changed her mind."

"It was last week, Jess."

The Club daughter ended up being too late to make the appointment worth it, so I used my spare fifteen minutes to do some re-stocking of my supplies and shot a text over to Eden asking when she was free next. She got back to me immediately with a picture of her and her son Oscar, both beaming, sitting on a bench at the park. 'Hey babe. Tony has Oscar Thurs night. Does that work?'

'My place this time,' I texted back. 'I want to give my MILF the full-body massage she deserves to get you nice and relaxed for afterwards.'

She sent me back an eggplant emoji, a peach emoji, a water spray emoji and a drooling emoji. I sent her back my address, followed by a heart emoji and a peach emoji.

Later, as the day was coming to a close, I sent Marissa a message asking if she wanted another massage after work since I had time to stay late. 'God, yes please,' she sent back.

I met her in the staff hallway and escorted her to my room. I'd already set it up with the breast bolster wedge, and soon we were into it as she told me about how she'd had some really crappy customers at the diner that morning, and then how one of the regular guys on the golf course had been a little extra tipsy and she'd had to cut him off, which he didn't like. That had led to a complaint getting filed against her, though it was so hard to read from the sloppy writing that she'd been assured it wouldn't even make it to her file.

We hadn't, and continued to not, talk about the topless selfie she sent me. Everything went professionally, and I didn't see more than a bit of side boob. And then, that night, she sent me another topless selfie but this time she was sitting on the floor of what must have been her bedroom, her boobs pulled out of the top of her pyjama shirt as she made a kissy face at her camera. She'd written in marker over her heart 'Trevor, Breast Friend' with a smiley face.

Thursday I rushed home from work to make sure I had everything ready. When Eden knocked on my door, I answered it dressed in a robe with all the lights in my little loft turned off and the inside lit by candles.

Eden had worn a cute sundress and had a little clutch in both hands and she bit her lip and grinned when I opened the door.

"Hey, baby," she said, almost bouncing with energy.

I'd decided ahead of time that I wanted to replay the way I had started things on Saturday, so I didn't say anything. I just stepped out of my doorway and scooped her up into my arms and kissed her hard, then brought her inside and kicked the door shut. Still holding her cradled in my arms, our kiss ended and I grinned like a fool. "Hey, beautiful." I slowly walked us over to my massage bench, which was set up in the middle of the lower level of the loft, and set her down on it softly. "How much do you like this dress?"

She raised an eyebrow. "It's one of my favourites, that's why I wore it for you."

"OK," I said. "Next time I want you to wear something you don't care about because every time I see you I just want to rip your clothes off."

"That would be so hot," she grinned and kissed me.

We made out for a little while, and then I stripped her naked - which didn't take long since she was only wearing the dress and no underwear.

"I've got a plan for you tonight," I told her. "Step one is giving you the full body massage and running my fingers over every single inch of your body, and step two is feasting on that delicious MILF pussy of yours until you've squirted at least twice for me. But for step one I need you to decide something for me."

"What's that, Trev?" she asked. She was naked and sitting on the edge of the massage bench, but somehow her energy and nervous excitement made her almost like a kid on Christmas morning.

I couldn't help it, I kissed her again first. "Well, I can use my regular massage oils," I said, showing her a bottle of the usual brand I used. But there was another, unlabeled brand next to it. "Or I can use this. I had a friend back in college who was a bit of a pothead, and she'd done research into THC oils and how to make weed massage oil. I've only tried it once before, and it worked really well. It's totally safe and gives your body just a bit of a high, and if some gets in your mouth then you can get a normal high from it. But, according to everyone who tried it in our program, the best place to use it is to lube your pussy or ass, because those spots are pretty absorbent. Basically, it gets your holes high."

"Trev..." Eden said, biting the corner of her lip as she considered it. "I haven't smoked pot since high school."

"I don't smoke pot at all," I said.

"How long will it last?" she asked.

"A few hours. That's why if we're trying it, we need to start now. Or we can wait until another time if you're not sure."

Eden bounced her foot as she thought for another long moment, then looked up at me with a grin. "Let's do it," she said.

I kissed her again, and she undid my robe to find I was naked underneath it, and already getting hard. Things moved quickly from there as she lay out on the table. I started the massage by kissing her bare back, then down to her ass and softly spreading her legs to give her a little bit of licking on her already wet pussy. Then I stood near the bottom of the table at her feet and pumped out a little bit of the weed oil and spread it on my hands, and started rubbing her feet, working the oil in between each toe and pampering her as she hummed happily. I worked my way up her legs and thighs, then over the meat of her ass. I kissed her back again and asked her how she was doing, and she said she felt great, so I kept going up her back and sides, all the way to her neck and shoulders.

"Alright, are you ready for more?" I asked her, putting my hand on her ass and sliding a finger into the crack.

She half-rolled over and stretched up to kiss me. "Finger my ass, baby. Get it ready for your cock so you can make it yours."

I kissed her harder, pawing at her tits with my oily hand and making her shudder, before urging her back onto her stomach. After reapplying some fresh oil onto my hands, I slid them both between her ass cheeks, oiling and massaging her soft skin, circling closer and closer to her puckered little hole. I teased it first, then worked my middle finger into the first knuckle. Eden gasped and giggled, flexing her ass on the invading digit. "Ready?" I asked her.

She nodded. "Do it, baby."

I pressed firmly, sliding my oily finger all the way in.

"Uuungh," she groaned, then hiccuped as she threw her head back. "Your finger is in my ass, baby. God, your finger feels so big, but I know you need to stretch me out. Get my ass high, baby. Get it perfect for your big stud cock. I want you to fuck my ass so hard, Trev. God, yes, finger me just like that. Is that-? Oh, fuck, a second finger already? MMmmmguh, fuck- it fit! Oh, babybabybaby, I feel so full and fucking slutty for you. Do you like fingering my ass, Trevor? Am I being a good, filthy MILF slut for you?"

"I love fingering your ass, Eden," I said, kneeling next to the bench so I could kiss her while I wiggled my two fingers inside of her, spreading the weed oil around. "And you're the best three-hole, cum loving, sexy as hell, premiere personal whore MILF I could ever dream of."

She closed her eyes, panting softly as she listened, her mouth agape and slowly curling into a smile as I fed her dirty talk kink. I kissed her again, then stood back up and started to slowly pull my fingers out of her ass, then push them back in. She mewled softly, her ass and hips shifting as she rode the feeling for a bit, before I slowly added a third finger. This took her breath away for a moment, and then she came, her ass clenching and her legs trembling a little.

"Maybe you should have tried anal earlier in life, hon," I said with a grin. "You might just be an Anal MILF after all."

"Fuuuuuck, I had no idea," she groaned, then looked back at me. "But I'm glad you're doing this, Trev. You're so fucking good to me, giving me everything I want."

I wiggled my fingers in her a bit more, then pulled out and watched her asshole quickly close, though not to that perfect pucker it had been before I stretched it a bit. "Turn over," I told her. "Time for the other half of your massage."

She did, humming happily to herself, as I wiped my fingers off with a wet towel and re-applied some more oil. I had fun working down her front and over her tits. She said the weed oil tingled a little more than usual on her nipples, but that was the only notable difference. I was just a few inches down her upper thighs, having avoided her pussy for now, when her eyes went wide.

"O-Oh... wow..." she said.

"What is it?" I asked.

"I think my high just kicked in," she said breathily. "My ass feels amazing, and God I want you to fuck me."

"Not yet," I grinned, continuing on with her thighs, and watched as she squirmed in place, flexing her muscles and absorbing the feelings running through them. Her nipples were poking out nice and hard, and she was arching her back a bit with her horniness and pushing her chest to the sky.

Spreading her legs, I got on the bench between them and looked at her pussy up close. I'd fallen in love with it that first time at her place, but I just couldn't get enough of how perfect and pretty it was. Aroused as she was, it was swollen a soft, ruddy pink, the inner labia spread slightly wanting something to fill it, her clit poking out from the little clit hood that capped it.

"Trevie, baby," she moaned, reaching down for me. "Fuck me?"

"I told you the plan, baby," I said with a smile. "Step two, I want a taste of this delicious pussy."

"Yes, baby," she whined, and pulled her legs wider apart for me, almost into a full split.

I dove in, slurping and sucking up her juices. I specifically did this before I started touching it with my fingers so that I wouldn't get utterly blasted from the high. I ate her for about five minutes, her pussy hot and leaking, as she sighed and giggled and mewled, calling out how she couldn't believe how good I was. And telling me how much she wanted me to fuck her ass.

When I eventually added my oily fingers and started lubing her pussy with the weed oil, she came just from the penetration, and it rolled through her into a second orgasm almost immediately as I added a little more oil and worked it inside of her.

Finally, with her pussy gaping open with a desire for more, I slid off the bench and went around to her face, cradling it in my hands and kissing her softly.

"Are you ready to be my three-hole anal MILF, Eden?" I asked her.

"God, I love the way you're willing to talk to me," Eden panted. "Tony thought dirty talk was beneath him."

"Tony was an idiot," I said. "You've got me now. You're my perfect little cum dump MILF pet."

"Trevor," she said, her eyes focusing a bit more on me as she put a hand in my hair and held me still. "I need you to fuck my ass right fucking now. I want to feel every inch of your cock claim my high-as-fuck ass and slam me so I'll never forget who it belongs to."

"As you wish," I said and kissed her softly. Then I manhandled her on the bench, lifting her up and flipping her over so that she was on her stomach bent over the side so that her feet were resting on the ground and her ass was pointed right at me. "Spread your cheeks, MILF," I ordered her.

"Oh, fuck baby, yes," she moaned, reaching back and spreading them. Her asshole was still just slightly gaped, a little winking hole as it rolled through the effects of the THC.

I didn't prep her anymore. She was oiled up all over. I just applied a bit more to my cock, stroked myself to ensure I was as hard as could be, slotted myself into place and started pushing in.

"Ye-e-e-eesss, my love," she moaned and gasped as the head of my cock wedged inside, and then almost easily I slid all the way into her as her sphincter rippled and her anal passageway gave way all the way to my hips pressing against her cheeks. "Oh, fuck, Trevor. You're in my ass. You're in my ass! Oh, God, you feel so fucking huge, but you're all the way in already. You're like Excalibur and my ass is the rock. You're a perfect fit, a perfect stud. God, fuck, you're so fucking big baby. It's so good. Fu-hu-huuuck yes."

I pulled out slowly, and pushed in again, and on the third thrust her knees started to buckle as she came wordlessly. I didn't stop fucking her though, and as she got her legs back under her I picked up the pace. It had to have been the weed oil, but her ass was pliant as hell, squeezing and rippling but stretching to accommodate my insistent cock. Soon I was fucking her steadily as if I was fucking her cunt, and then I picked it up more and I was really pounding her as I grabbed her by the back of her scalp and pulled her back to me.

"Fuck my ass. Fuck my ass. Fuck it, Trev. Oh my God, I love getting my ass fucked by you. You're taking my ass virginity and I fucking love you. Holy fuck, baby, you're so fucking good at ass fucking me. Please, baby, come in my ass. Make me gape. I want to do whatever you want. I'm your dirty MILF sex slave."

I pulled out of her entirely, watching her ass flex as if it were expecting another thrust, gaping open for a long moment as she moaned sadly at the feeling of emptiness, then I thrust into her again as she hiccuped and then started laughing.

"Fuck, that hurts so fucking good, Trevor," she gasped between laughs.

"You like that, my little bad bitch?" I asked and pulled out entirely and then shoved just the head back in. "You like it when I stretch your little asshole over and over?"

"Do it, baby," she whined. "Do it."

I did. I fucked her asshole, in and out, over and over, feeling that tightest ring resist over and over as the oil lubed my way in.

"Fuck, Eden," I grunted. "I'm going to come."

"Baby, I've been coming forever," she whined, tears actually dripping down her cheeks as she smiled sloppily back at me. "Give me it, I want to feel it. Come in my ass."

I pushed all the way in, and she gripped me like a tight, hot glove, and I exploded into her.

It took me a couple of minutes to really come back to awareness, and I was still hard in Eden's ass. My cock felt like it was super light and super heavy at the same time, like a steel beam without weight, and I realized that I'd picked up my own high from all the oil.

"Eden," I groaned, slowly pulling out of her ass until I popped out.

She moaned happily, rolling onto her side, and I managed to lift her up and slide her onto the massage bench. "Hey, baby," she grinned. "Up until this afternoon, I thought last weekend was the best sex I'd ever had. This definitely tops it."

I laughed, and she did too, and I crawled up behind her on the bench and spooned her as she tilted her head back so I could kiss her.

"You're still hard," she noticed.

"I am," I grinned.

"Good," she said, sliding off the massage bench and heading to my little kitchenette and grabbing a washcloth. "Because I want your next two loads deep in my cunt. Then you can pick where you put it on or in your personal MILF after that."

* * * * * * *

I lost track of how many times either of us came. Hell, I couldn't really remember the transition from the massage bench up to my loft bedroom, but that's where we ended up. I know I fucked Eden's ass at least a couple more times that evening. I also woke up to a massive, cold wet spot covering most of my bed from her squirting at least a few times.

I hadn't much cared when I got back from driving her back to her place - she'd sucked the weed oil off my cock, so she'd been way higher than I had gotten.

Work the next day was rough to get going, and Jessica kept making cracks about me having a 'big night' and 'I remember when I had my first beer.' Little did she know.

Eden texted me halfway through the morning, first a picture of her asshole as she spread her cheeks. It looked a little sore and swollen, but the picture after it of her happy, tired face said she didn't seem to mind. She also apologized for telling me she loved me in the heat of the sex, and I told her I didn't mind at all, and I loved her in the heat of the sex too. That made her send me a little video of her blowing a kiss at her cell phone camera and winking. "Thanks for understanding, baby," she said.

At lunch Marissa could tell I was feeling off, which she teased me about a bit. She even asked, quietly, if I'd stayed up too late jerking off to her topless pictures.

I grinned a little, "No, though I have to say they are pretty amazing."

That made her roll her eyes a little. "That's what they all say."

"Well, they all must be right then," I teased her, giving her a little nudge with my elbow.

Right near the end of lunch she turned to me. "Hey, are you doing anything tonight? I don't have a shift at the shelter, and there's this bush party happening. A bunch of the folks from the kitchen and the maintenance crews are going."