Jay Friday
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The Masseuse (Ch. 24C: Decisions)
🕑 Added 2025-07-24 13:00:09 +0000 UTCAuthor's Note: if you've for some reason decided just to skip ahead, please understand that this chapter is one of four different endings to the story.
They both blinked.
Claire spoke first. "Are...are you sure?" She looked me up and down, obviously thinking that I was pretty turned on, that it was her turn, and she'd probably be able to finish me in no time. And she was almost certainly right about that.
But I wanted this to go a very particular way. I nodded.
She swallowed, hard. She looked like she was about to cry, obviously thinking Olivia would easily be able to finish me in forty seconds.
Olivia, who had just pulled off of my lap, leaned forward. She stood between my legs, eyes downcast, perfectly submissive and demure. "Okay, it was forty seconds where you get to tell me what to do...so...what is it you want me to do, Rick?"
I took a deep breath. "I want you to take that dildo and finish Claire off."
Both of them stared at me, speechless. Olivia finally broke the silence. "Uh, rules-wise...who wins the date if she cums?"
Claire was ready with an answer. "I do. If Rick makes one of us cum, that person wins. Those were the rules."
Olivia waved a hand. "Yeah, but it wouldn't be Rick making you cum, it'd be me. So I should win."
Claire didn't like that answer. "That's bull--"
I intervened. "Olivia, while you're making her cum, I'm going to make you cum. After that, we're all going to get dinner and talk about..." I gestured with my hands, encompassing all three of us. "...this. Us."
Her lips curved up into a smile. "Wow, Rick. Pretty brazen of you. So you want both of us, huh...that wasn't really what I had in mind when I said 40 seconds of me being a good girl for you..." Olivia looked at me, thoughtfully.
Then a mischievous smirk dawned on her face. "I'll tell you what. You fuck me while I'm using the dildo on Claire. If you can make me cum, the three of us do dinner together. But if you end up cumming before you make me cum...if I'm the one who makes you and Claire cum, instead of you making me cum..." she rested one hand on the back of Claire's neck, and the other hand on Claire's thigh. "Well...I'm taking Claire to dinner, and you're out of luck. You want both of us? You gotta be able to handle both of us."
Claire bit her lip. She looked down at Olivia's hand on her thigh, and then looked between Olivia and me. "That...that seems fair...we're all really turned on...you'll be able to do it, right Rick? You just have to last." She looked at me hopefully.
I wasn't at all sure I could last long enough to make Olivia cum. I tried to think of how to shift what was about to happen, to make it more likely for things to turn out the way I wanted.
Claire smiled encouragingly. "We'll do it together...I'll be trying to help you get her to cum too..."
Olivia looked at me. Her smirk was knowing now. "C'mon, Rick. Two hot girls. Yours for the taking. A real man," she giggled, "...would say yes in a heartbeat."
I felt my face go red. Now I had to say yes. And Claire wanted to help me...I just had to last. "Okay. Let's do it."
"Okay..." Olivia picked the dildo up, and Claire lay down on the massage table. Olivia bent against the massage table next to her, glancing back at me with a grin. "Ready, big guy?" She wiggled her hips.
I nodded, staring down at her ass in front of me, already thinking about what it would feel like in my hands.
She leaned over Claire. "Are you ready?" she asked her softly, whispering in her ear.
Claire took a deep breath and nodded as well, and then gasped as Olivia stroked the dildo's head between her thighs.
I stepped up behind Olivia, grabbing her hips, and lined my cock up with her entrance. She glanced back at me. "Who do you think will cum first, Rick? Claire? You? Me?" The confidence in her voice made it clear she thought the last one unlikely.
My cock twitched. I took a deep breath, and slowly started to work my thick shaft inside her. "Whatever, Olivia. You've talked about how you're a size queen...you think Claire's hot...you're gonna love this..." She bit her lip, and meeting my eyes, moaned at me as I slid in.
Claire reached up and tweaked one of Olivia's nipples, making her gasp. "Mmm, you're so sexy, Olivia...I love the way you can take him..." she purred.
Fuck. The only problem with Claire trying to help me make Olivia cum was that it was turning me on, too. I tried to breathe evenly. I knew this was going to take some time -- I couldn't cum in Olivia in four or five pumps. I was going to have to fuck her.
And while Olivia was clearly turned on by having my cock inside her and clear next to her, she didn't seem to be out of control yet. I could feel her body rythmically against mme as she fucked the dildo in and out of Claire. "Mmm, Claire, I love the way your tits move while I'm fucking you with this, it's so fucking hot..." she reached down, fondling Claire's breasts, and I heard Claire let out a moan. At the same time, Olivia was bouncing back into my cock.
She looked back over her shoulder, smiling at me. "This was a good idea. Fuck, I love how big you are. Claire, he's just so thick...mmm, you feel so tight around this dildo, I can barely take all of him so I bet he really fills you up..." She was throwing her ass back onto my cock with enthusiasm now, punctuating the words.
Claire just wordlessly moaned in agreement in response. Olivia was thrusting the dildo hard into her now, and the way her tits were bouncing up and down in time with Olivia's ass bouncing against my hips was...distracting. More than distracting. It was fucking hot. I had never done anything like this. I could feel my orgasm building. I tried to hold still and focus on lasting.
But Olivia continued to fuck my length, rolling her hips back into me. "Ah...she's really wet, Rick. And she feels so tight. I see why you cum so quick inside her." Claire was panting now. So was I, I realized.
Claire made eye contact with me. Buried under the arousal written all over her face, I could see she was...concerned. I was starting to get worried, too -- I had figured Olivia wouldn't be able to handle both of us this easily. I saw Claire visibly gather herself, trying to reassert some control. "Olivia, do you like t-taking Rick's thick cock while you f...fuck me?" She tried to say it seductively, but the effect was somewhat spoiled by Olivia continuing to thrust the length of the dildo into her, eliciting moans from Claire.
"Mmm...what I like is how turned on you both are...do you think you'll cum first, Claire? Or will Rick?" Claire didn't respond. Olivia was thrusting it into Claire fast and hard now, and Claire's eyes were wide, staring down at the length of the dildo going in and out of her. I was watching it, too. Olivia was really going to town on her.
Olivia just kept talking. "I bet Rick will cum first. He's never fucked you to an orgasm. I don't think he's going to be able to last long enough to cum after you either." She made eye contact with me. "Let alone lasting long enough to make me cum on that big dick. Certainly not in a threesome like this."
I knew she had a point. I was trying to last. I had stopped moving, trying to last longer, but Olivia just kept backing that round ass up onto my cock. I was trying to focus on not cumming, but the way Olivia was fucking Claire while she was fucking me was impressive...and erotic.
As I watched, silently trying to control myself, I saw Claire close her eyes. "Oh, fuck, that feels so good..." she whispered the words, almost embarrassed, and then started meeting Olivia's thrusts with her hips, frantically working herself down onto the dildo as Olivia thrust up into her.
"That's right...take it..." Olivia purred. "You just need a good, hard, pounding for a change...one that lasts more than thirty seconds..." She looked back at me, and glanced down at my cock meaningfully. Her movements felt so good -- she was slick and wet, and each time her ass bounced off my hips I could feel myself get that much closer to losing control.
I tried to think of something to say, anything. Something to get Claire to focus, to break Olivia's rhythm, to distract myself from the mounting sensations. But it was all was too much. I looked down at Claire, who was lost to the pleasure Olivia was inflicting on her, getting fucked in a way my dick couldn't deliver. It was humiliating.
I felt myself boil over.
I was cumming and there wasn't anything I could do about it.
"Claire, I-I can't..." I barely got the words out before I started orgasming, hard. I grabbed Olivia's ass and thrust into her hard as I lost control.
"Mmm, I can feel you cumming, Rick..." Olivia said. "I guess you weren't really ready to handle both of us..." As my orgasm started to subside, she slowed down, and brought her other hand down to Claire's clit, working it with her thumb as she continued to fuck the dildo in and out of her.
The effect was almost immediate. Claire's eyes snapped open, and her whole body tensed up. "Oh god oh god oh g---" and the words dissolved into a long, drawn out cry, her legs shaking as she came.
Fuck. I leaned against the massage bench, dazed, watching as Olivia fucked Claire thoroughly through her orgasm.
When it was finished, Claire took a few deep breaths, clearly gathering herself. She and I made eye contact. Sorry, she mouthed. I tried.
Olivia glanced at me. "Well, you were the one who took us down this route, Rick. We talked about the stakes. You just couldn't handle it. So Claire and I are going to get dinner...sorry you're not invited."
Claire looked at me sadly. Olivia's expression was some weird combination of disappointed and smug that I didn't have the mental bandwidth to unpack.
I didn't know what to say, so I didn't say anything. I dressed quickly, my face burning with shame, and left. This was not how I wanted things to turn out...but it was too late now.
I spent a few minutes at home, wallowing in shame while I showered. All I was thinking about was Claire and Olivia at dinner, what they might be talking about, what they might do after, all without me...when I heard a ping from my phone. I finished showering quickly, hoping it was a text from Claire or Olivia. But it wasn't.
Brittany: Hey, you around tonight? ;)
Most nights, I would've ignored it, or put her off. I didn't like Brittany. I didn't trust Brittany. But this wasn't most nights. My ego was bruised. Brittany was hot. Brittany was into what I had to offer. A chance to reclaim some semblance of dominance had a lot of appeal. So after a moment, I texted her back.
Yeah. What's up?
Brittany: Claire just let me know she's out for the night. Want to come over?
Out for the night. Claire was out for the night. Well, that fucked me up pretty good, and it made my reply a foregone conclusion.
Yeah, I'll be in there in 20. Hope you're ready to play.
I was getting in the car when Brittany sent a photo in reply -- her, in the living room of their apartment. She was wearing some kind of pajama set that clung to her curves. Her tongue was out as if she were about to take a long lick of something.
If I had been paying closer attention I would've seen the two half-empty wine glasses in the background behind her.
But I wasn't.
Brittany came out of the elevators to meet me. She drew stares from other people in the lobby. She was wearing the sexiest pajamas I had ever seen -- green satin or silk or something, short shorts that clung to her hips and ass, leaving her legs bare, and a top styled after a men's shirt, cut loose and low enough to show off the swell of her breasts.
She didn't seem to mind any of the stares -- including mine. She smiled at me. "Hey, Rick."
"Hey." Now that I was here, it didn't seem like the best idea I'd ever had. I thought about turning around and walking out of there.
"Imagine my surprise when Claire told me she was out for the night but you were available...trouble in paradise?" Brittany said the words teasingly as she started walking towards the elevator.
"Yeah," I muttered, watching her ass sway as she walked away from me, thinking of Olivia.
Brittany's question was an unwelcome reminder.
Fuck it.
I was so frustrated by how earlier today had turned out. I needed to blow off some steam, and her body in those pajamas, and the way her lips curved up, had me thinking of countless ways I could do just that. I followed her. "Why are you at home wearing PJs on a Friday night anyway, Brittany? Not really your style..."
"Maybe I'm turning over a new leaf. Maybe I stay at home now instead of partying. Maybe I'm a good girl now." She looked up at me and licked her lips.
I felt my cock twitch. She glanced down, and grinned. The elevator pinged and we walked down the hall to her apartment.
There was a jacket on the hanger by the door that looked familiar, but I was only able to glance at it for a moment before Brittany had her tongue down my throat and a hand grasping the length of my cock through my jeans. "I can't stop thinking about this," she moaned as she gave my now-hardening cock a squeeze. She led me over to her couch, and pushed me down onto it, standing between my legs.
Jesus. In spite of the orgasms I'd already had today, I felt my libido go from zero to sixty almost immediately. She was hot and sounded so desperate for my cock. The memory of her, desperate for me to cum on her face, was etched in my mind.
This is what I had been hoping for, how I had wanted to spend the night with Claire and Olivia. I was rock hard.
"Take it out, Rick..." she purred the words, unbuttoning her top. She wasn't wearing a bra underneath, and her tits -- full and firm, her nipples hard -- came into view.
I didn't have to be told twice. I struggled out of my jeans and boxers, freeing my thick length.
Brittany knelt in front of me. She made eye contact, and spat on my cock, before starting to pump it with both hands, lubricating the whole length. I moaned. Fuck.
She took a few moments just staring down at it, openmouthed, as she worked it . "God, you're big, Rick. It feels so good in my hands..."
She knew how to handle me. She worked up and down my length with her hands for thirty seconds or a minute, before looking up at me seductively. "So...I have a confession to make..."
"Y-yeah?" I almost moaned the words out. If I hadn't cum so many times today I knew I'd already be right on the edge. As it was, her attitude, how sexy she was, the way her hands felt...I knew it wouldn't take long.
"I was actually having a bit of a girl's night here, when Claire texted me..." she continued to pump my length as she spoke.
I froze. From down the hallway, I heard the sound of a door opening. One of the bedroom doors -- either Claire's or Brittany's, I couldn't tell which.
"...and, well, I happened to be talking about you anyway, telling a...mutual friend of ours...about the...encounter we had..." She bit her lip, continuing to pump her hands up and down my slick cock.
All of the details suddenly snapped into place. The two wine glasses...and I realized I did know that jacket by the door. I had gotten it for Emma...for her birthday, last year.
Emma came around the corner, arms crossed. She giggled. "Hey, Rick."
"Uh, hi, Emma? What the f---" but I couldn't finish the sentence. Brittany bobbed her head down my shaft, and I moaned instead.
"Brittany was telling me about your, uh, hookup I guess...sounds like you still, um, cum quick. I would've thought me dumping you might've been a wake-up call, but I guess not..." Emma observed.
Brittany made an mmm of agreement, her mouth full of my length as she worked me. I struggled to keep talking, to focus on the conversation instead of the feeling building in my balls.
She smirked at my struggle to control myself. "Brittany asked me if I wanted to see firsthand how you were still cumming quick...and well, I've had a couple drinks, so I said sure..." she giggled again. "And so here I am. And here you are, about to blow your load quick, as usual."
I flushed. "I-I've been working on lasting longer."
Emma assessed me, her mouth quirking. "It doesn't really seem like it...you've been here for like, a minute or two, and those sounds you're making are awfully familiar."
She was right. I was getting close. Fuck. I tried to pull myself together, biting back another moan.
"I--I don't really want to do this with you watching..." I muttered.
Brittany pulled her mouth off my cock, and resumed pumping me with both hands. "So...don't cum then. Or just leave." she purred. She positioned her face underneath my cock, and started tonguing my balls.
I moaned as she worked me over. I was so turned on.
Emma crossed her arms. "Yeah, just don't cum, then, Rick. Easy." She had the same half-smile on her face as she rolled her eyes at me.
I looked between them, my gaze finally resting on Brittany's face, mouth open, as she relentlessly pumped my cock. I wanted to leave. But I knew it was too late for me to stop myself. I needed to cum. I felt myself about to boil over.
"Mmm...Rick...I know that look from last time..." Brittany's eyes had a glimmer of mockery in them.
"I do too," Emma chimed in. "I don't think he'll last another ten seconds, Britt."
Fuck. My face burned. I wasn't quite there yet. "I-I can..."
Emma laughed. "No you can't."
Brittany giggled. "Just cum on my face, Rick. We both know you're a two-pump chump. I don't know who Claire's out with tonight, but I bet it's somebody who can actually last long enough to make her cum."
Her hands were pumping me, relentlessly. Emma's smile was almost cruel as she watched, waiting for me to lose control. "God, Rick, you were always such a quick cummer for me, and I see nothing's changed."
And just like that, I couldn't hold back anymore. Moaning, I started cumming.
Brittany immediately pulled her hands away, and my moan turned to one of frustration as she ruined my orgasm, my big cock jerking and twitching above her face.
I hung my head, gritting my teeth in frustration, not making eye contact with either of them. Fuck.
Emma spoke first, her voice dismissive.
"Why don't you help Brittany clean up and then leave, Rick. She and I have a lot to talk about, and you probably don't want to be here when Claire comes home."
Brittany giggled as I helped her clean up, put my pants on, and headed for the door. "I liked doing it that way, Rick. I'm not sure you deserve to enjoy an orgasm. I'll text you. Maybe we can do it again sometime."
I wanted to tell her to go fuck herself.
But I doubted I was getting any more massages any time soon, the way Olivia had been talking. Who knew what Claire thought of me...especially after doing this with Brittany. So this might be my one sexual outlet for the moment...
And...worst of all...I had kind of liked it.
"We'll see," I muttered.
I could still hear their laughter from the hallway after I shut the door.
Comments
DarknessFalls888
Anticipating the last ending, my boy Rick gotta get a W, at some point!
