Cady’s heart was absolutely pounding as she got to her room and closed the door behind her. With just a few words from Kelly, she had gone from unspeakably mortified to absolutely exhilarated. He’d agreed to come join her at the end of his shift in another hour. She’d left him a tip that was suitably generous, but — she thought, wincing, of the sex worker comment — wasn’t so large that it would raise any eyebrows on the spa receptionist either.
Now, what does a single middle-aged litigator traveling for work wear for an unplanned sex date with a gorgeous young hottie? It was a somewhat familiar dilemma, as she fondly remembered Lucas from her girls’ weekend. They hadn’t kept up any pretense that they would ever be in touch again, but every once in a while he would send her a text of his view of the lake or the mountains, knowing how much Cady loved it where he was. It was just a way of saying “hi”, and it always fondly reminded her of being out there and meeting him. Since her own view of the parking lot of the office she was usually at sucked, he usually got a quick upskirt shot back.
But tonight, there was a different man that she hoped would go up her skirt. Taller, blonder, even younger, and just as gorgeous. Lucas had a certain intensity about him, whereas Kelly seemed laid-back and with an easy laugh. He seemed like exactly the right kind of person to name after a champion surfer; he must have even been a chill baby.
Cady opened her suitcase in despair. Work clothes, stuff to sleep in, workout clothes, a swimsuit, and the spa robe were the options. The only viable options were the little cotton shorts and white t-shirt for sleeping. The robe felt too — Hugh Hefner, and the others were just ridiculous. She brushed her teeth and tried to fix her hair, which was a little wild from being in the face cradle. She appraised herself in the mirror and hoped she’d be attractive enough.
Cady had not been reading her book in bed for very long when she heard the soft knock that — good grief, just the knock made her insides melt — meant he had arrived. She welcomed him in and saw that he had brought an entirely decent chilled bottle of sauvignon blanc with him as well. He smiled broadly at her as he came in the room. “Best bottle I could talk them out of at the bar.”
“That’s very sweet of you to bring, Kelly, thank you so much for coming. I have to apologize to you again, I cannot believe that I said what I ….”
And just like that, he cut her off with one tanned forearm wrapping quickly around her waist and two fingers to his lips. He was smiling, and he spoke with an almost conspiratorial tone as he leaned down towards her neck, although no one was around to hear.
“I had to say what I said. I don’t want to lose my job for massaging my clients between their legs…no matter how much I might want to. But believe me, there is nothing to apologize for. I like a woman who knows what she wants, and knows she deserves pleasure.” And he relaxed his arm from her waist, pulling back slightly to study her reaction.
Cady was momentarily at a loss for words. She did know what she wanted, and she definitely wanted this man to stay in her room as long as she could keep him. He smelled amazing, and his pulling her in and hearing his breath warm on her ear and neck as he bent and leaned down to her height was making her dizzy. His voice was warm
“I….thank you. I do like….pleasure.” *Good work*, *Cady,* she thought. *You’re definitely dazzling him with your conversation here.*
To her relief, he laughed, that great laugh that she remembered from before. “Me too. Have any cups?” He asked. “It’s a screw cap, no worries there.”
They sat on the sofa in the suite, side by side, and had the wine and talked for a while. He was so very young, but they still had enough in common to talk about between places they had been and beaches they liked. He was just as easygoing as he had seemed to her before, and she felt comfortable with him right away.
“So….can I ask you why you wanted to come up here? You must have girls your own age chasing you all the time.” Cady asked him.
“Ohhhh, this is the part where the clearly hot lady fishes for compliments, but that’s ok, I’ll play along…You’re going to sit there in a see-through white t-shirt that shows off those perfect tits and perfect nipples and shorts that are about three inches long and bat your eyes at me and ask why I on earth I wanted to come up here, but that’s ok, I’ll play along,” he responded, flashing that dimple again. “You know that milf is now, has always been, and always will be a thing, right?”
“I know about it, sure…”
“And you know that for most of that massage, I was hard as a rock, don’t you?”
Cady stopped with her cup halfway to her lips. “You were not. You’re a professional massage therapist!”
“I am also a heterosexual man without a girlfriend at the moment, and I absolutely was. You couldn’t see me, and I made sure not to brush against you with it…and I made sure I was out of the room before you got up, remember?”
“Huh, ok. I did not realize that.”
“You have really soft skin, and you have these really nice calf muscles, and thigh muscles, and shoulder muscles, and I just, I couldn’t help it. I loved everything I touched. I loved your tiny little hands even. How can you be an entire grown woman with baby hands like that?!” He laughed, leaned back just a little, and grabbed her hand to study it again, and Cady couldn’t take it. She leaned into him and kissed him, unhesitatingly, on his perfect mouth. She tasted mint and wine and heat and desire, and she grabbed the back of his head to hold him to her. When he released her hand, she pressed it to his chest and felt the most beautiful indentation between his firm pecs, and her pussy throbbed at the thought of what his chest must look like. How many times had he surfed shirtless off some beach in Hawai’i or California or Thailand and she hadn’t been there to see it? It was tragic.
He kissed her back with enthusiasm, and his hands wrapped around her waist. There were those hands again, damn he was strong. And through the thin white t-shirt she could feel the slight callouses on his fingers and it drove her wild. Was it evolutionary? This is a man whose hands could change the oil in my car or build me a bookshelf so I must mate with him? Heaven only knew, but they sure did work.
And before she knew it, she was on him. Straddling him on the couch. And she knew he hadn’t been lying before, because he already felt as hard as could be underneath her. And the thin white t-shirt was off in a flash, and she arched her chest towards him, aching for him to take her nipples into her mouth.
But Kelly was clearly in no particular hurry as he stared down at them — he really was tall, she thought — and massaged one nipple between his fingers. “They’re so perfect,” he murmured, “they’re pink and small and perky and I just love them.” And finally, he took one in his mouth and licked, ever so gently, all around it and up the firm quivering tip. Cady exhaled with a deep breath that was part relief and part pleading for more.
“You grew up in Florida, right?” “mmmmmm” was all he said, as he licked and sucked her tits, but it didn’t seem to be a contradictory “mmmm.”
“You know muscadine grapes? Or scuppernong grapes? Scuppernong is a subset of muscadine.” At this apparent botanical lesson out of the blue, Kelly laughed with her nipple still in his mouth and then pulled away, grinning.
“Your pillow talk is kind of weird, you know that Cady?” he said, and oh God, he had these twinkly blue-grey eyes that seemed so happy…
“I know, I’m getting there. You know the grapes though, right?” Cady found herself short of breath from panting and found it a little hard to talk.
“Yeah, I know them. Really juicy, but tough hulls. Pop the insides in your mouth, leave the hull…My mom used to grow them.”
“Perfect. So what I want you to do is bite my nipples just like a muscadine, and suck out the inside. Bite down until that nipple pops just right between your teeth, and suck it.”
And Kelly grinned and said, “I know *exactly* what you’re talking about, but you’re going to taste so much better,” and within a few seconds Cady was in ecstasy. His teeth provided the perfect amount of sting, and made her body sing and throb like a perfect chord picked out on a guitar. After a little while, she separated his mouth from her from the shortest possible time needed to pull his shirt off from over his head, and for just a second it took her breath away. He was flawless, just a perfectly muscled chest with ginger-blond hair and taut pecs above defined abs, covered in that effortlessly smooth skin of the young. “Oh God, will you look at you,” she breathed, “I could just paint you.”
“Like one of your French girls,” he teased, “but would you share what is obviously a large enough door with me?”
“You can have the door, Kelly honey, I’ve lived my life. It’s been a great life goodbye, cruel world….just let me fuck you one time before I go…”
“Only once?” he breathed heavily in her ear, pulling her bare chest to his bare chest. “Baby, I’m not sure you realize exactly what you’ve summoned here tonight.”
Source: reddit.com/r/eroticliterature/comments/h790qf/the_work_weekend_part_2_mf_milf_age_gap_female
Part 1: [https://www.reddit.com/r/eroticliterature/comments/h0nwfn/the_work_weekend_part_1_mf_milf_age_gap_female/?utm_source=share&utm_medium=web2x](https://www.reddit.com/r/eroticliterature/comments/h0nwfn/the_work_weekend_part_1_mf_milf_age_gap_female/?utm_source=share&utm_medium=web2x)
The pillow talk adds a previously ‘human’ aspect to this story… so hot… on to part 3
Without searching, I like to think this the first post to tag grapes in it but ?♀️