Jay Friday
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The Masseuse (Ch. 24A: Decisions)
🕑 Added 2025-07-10 12:00:07 +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.
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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...
Which was why I was calling in those forty seconds now. I looked at her, sad, and trying to be gentle. "Yeah, I'm sure."
"O-oh...okay..." Claire looked crushed.
Olivia, who had just pulled off of my lap, leaned forward. She stood between my legs, eyes downcast. "Okay, it was forty seconds where you get to tell me what to do...so...what do you want me to do, Rick?" Her tone was...submissive? It was completely out of character for Olivia.
I stood up. I needed to move fast. Forty seconds wasn't a lot of time, and I knew this would put me right back on the edge again if it didn't finish me. "You lie down on the massage table. Touch yourself, and let me know when you get close."
She did so, rolling onto her side to face me, and beginning to work herself with both hands -- two fingers inside her from one hand, and the other working her clit. She was letting out little gasps. It was hot to watch, and I felt my cock leaking precum...
But I was keeping half an eye on the clock. I watched ten seconds tick by, then fifteen. I couldn't tell if she was going fast enough. Shit. I had wanted to win by making her cum, but I wasn't sure that was going to work. Well, she was supposed to be being submissive. I quickly reached down and tilted her chin towards me. She looked up at me, biting her lip, and I stepped close, my thick length nearly right against her face.
"A good girl would be able to cum quickly for me, Olivia." I tried to say the words dominantly as I looked down at her.
She looked both amused, and a little defiant. "I-I'm trying..." she moaned the words.
"Maybe you need some help." I climbed on top of the massage table, lying on top of her. I positioned the head of my cock at her entrance. I could feel her hands moving frantically now. She pulled one of her hands away, the other continuing to work her clit, and I thrust my length into her. I was worried about being too rough -- but she was incredibly wet.
She moaned. "Oh, fuck, so big..."
Fuck. I never got to hear Olivia out of control; she was always running the show. This was so hot. I felt my orgasm quickly building as I thrust into her a second time. She moaned again.
"Yeah? You like being underneath me while you take my big cock?" I had no idea whether I was going to last long enough for her to cum, but I didn't care anymore. Her body underneath mine felt amazing. I reached down, both hands gripping her ass, and thrust into her again.
Her voice was right in my ear. "Yes...I-I'm gonna cum..."
So was I. I thrust again.
"Fuck, Rick." I felt her tense underneath me, her hips locking, as her climax began.
I thrust one more time and then lost all control myself, pumping repeatedly as I exploded into her.
We lay there for a moment.
The silence was interrupted by the sound of the door opening and closing as Claire left the room. I felt a stab of guilt.
But my eyes were full of Olivia, looking up at me.
"I...I think we've got to talk about a few things over dinner." Her voice was quiet and pleased, and her smile was knowing.
I nodded.
---
Olivia and I had broken off the massage sessions. My platinum package was about up anyway, and having me repeatedly show up at the massage parlor to see Olivia, felt unfair to Claire. I had apologized to her, and she had accepted it, and said she understood, that there weren't hard feelings...but it still felt a bit like an open wound. I hoped time would heal it -- I liked her, and so did Olivia -- but it felt like the best thing to do was to give Claire space.
I didn't hear from Brittany again. At times, I assumed she, and Claire, and Emma were all off somewhere comparing notes about me. I felt bad about that -- a weird mixture of guilt and shame -- but I had made my choice. It was always going to hurt someone, wasn't it? And I wanted to move on.
On the other hand, I heard from Natasha all the time. She started taking steps to bring that mesh harness to market. I participated in several pitches and demos with her -- I'll let you imagine what they were like -- and she got some big investments. Those big investments turned into more investments, and I started to see some actual returns on my investment. It wasn't enough that I could stop working, but it was enough that I just didn't stress as much about work. If I lost my job, I could get another one, or maybe just work with Natasha full time. It felt less existential.
Anyway, like I was saying: Olivia and I broke off the massage sessions -- because we didn't really need them anymore. We saw plenty of each other outside of her work.
I'll also let you imagine the kind of sex we were having. It was, as you might suspect, mostly sex where she ran the show, and, as you might also suspect, it was mostly sex where, I uh...didn't last very long. Or if I did, it's because she was teasing me, letting me ride the edge. I'd like to tell you I got better at lasting longer. Maybe I did, a little, but she still knew just what to do if she wanted me to lose control. Every now and then, though, she'd look up at me with that same glimmer in her eyes from the forty seconds during the contest, then look away quickly, and I knew she wanted something different. I was always happy to oblige.
There is one time that I should probably tell you about in greater detail, though.
I showed up at the massage parlor at the time we had agreed on. It was late -- nobody else there, just me and Olivia. I had asked Natasha to leave a bit early -- and for a few other things -- and she had readily agreed.
Olivia greeted me by the door with a kiss and a smile. "Hey, I'm surprised you wanted to come back here since--"
I shushed her. "Why don't you head back to the usual room and...undress to the level of your comfort. I'll be in in a minute." I said the words with a grin.
She let out a little giggle. "Oh. It's like that, huh? Okay."
She sauntered away. I watched her go. I was pretty sure I would never get tired of staring at her ass.
It took me a few more minutes to join her. She looked up from the massage table as I entered the room and laughed.
"I didn't even know one person could even get that on by themselves."
I was wearing one of Natasha's prototype harnesses. "It, uh, takes some doing," I admitted. "But I've got a little practice."
Then I held up one for her. She let out a giggle. "Mmm, Rick, what do you have in mind?"
"There's a feature set I don't think you've seen yet...Natasha and I tried it a while back and...well, I think you'll like it. I wanted to make sure you got the chance to try it."
She sat up and I helped her into the harness. She was naked, and my fingers -- and gaze -- lingered on her skin, tanned, and warm. It took way longer than it should've. Olivia made it more difficult on purpose -- leaning away from me, brushing her ass against me, at one point lying her leg across mine -- and by the time she was in the harness, I was rock hard. I pulled out the laptop and tweaked some settings.
She looked at me curiously. "So...what's this feature set? God, feature set. You're starting to talk a bit like Natasha now. Maybe you're spending too much time with her..." a whine drifted into her voice, "...and not enough time with me..." As she spoke, she reached out, caressing my length.
Her touch, as always, was practiced, perfect -- exactly calibrated to feel incredible. I gasped, and almost simultaneously, she gasped.
"It...it makes you feel the level of arousal I'm feeling," I said. I was staring at her. Fuck, she was hot in the dim light of the massage room. The mesh harness looked outrageously sexy on her, clinging to the curves of her hips and breasts, her nipples poking through the mesh...
She bit her lip, watching me watch her. "Mmm...is this how turned on you are just from looking at me and having me touch your cock? Fuck, Rick..." She stood up and pushed me down onto the massage table. My cock twitched, and I heard her give a sharp intake of breath as she stood next to me, looking down at me.
"Remember the first time you were in here?" Her lips curved into a smile.
My face heated. "Y-yeah, of course..."
"All brokenhearted over Emma..." she teased. "And you didn't want to tell me why she had dumped you..."
"I...I didn't want the hot new masseuse to know I didn't last long enough to satisfy my ex," I confessed.
"Oh, but I could tell right away, Rick," she purred. She let out a moan, which made sense -- reminiscing like this was turning me on further. "And then...when I started massaging you, you got hard so quick..." she was putting massage oil on her hands.
"Well, you're really good at it." I blushed.
"I am," she said, wryly, "but you're also so sensitive...ah..." As she was speaking, she reached down, and wrapped both of her hands around my cock. It felt amazing for me as she lubed up my hard length -- which meant it felt amazing for her, too, the harness matching her arousal levels to mine.
"Fuck, this feels good," she moaned. "You...couldn't...last two minutes then...think you can do it now?"
I was breathing hard, staring at her hands as they worked up and down my cock. "I...maybe..."
Her lips curved up, and she leaned down to whisper into my ear, a smirk in her voice. I could her breathing was shallow. "No you can't. If I make you cum from a handjob, do you think the harness will make me cum too?"
"I--I don't know..."
She was pumping me faster now. I was trying to hold back, to slow it down. It would be nice to have actually improved my stamina since my first appointment, I thought. I had a lot more practice. I gritted my teeth, trying to last.
"Let's find out," she moaned. "It--it feels like it might...fuck, this feels so good, you must really like my hands on this big dick..."
Her moaning wasn't helping me to keep control. I met her gaze, the arousal in her face only making it that much harder to stave off the mounting orgasm I could feel ready to envelop me.
"Mmm...it's been like, a minute, Rick..." The glee and desire in her voice was out of control. "This is just like the first time..."
My face burned. So much for having a lot more practice.
She looked down at me. "Fuck, I can tell you're gonna cum if I keep going...you just can't control that cock..." Her hands were moving frantically now, almost spasmodically, her own arousal making it difficult for her to maintain her usual practiced touch.
She was, of course, right. "Olivia...Fuck, s-slow down...we can make it last longer..."
She gave me a knowing smirk, the wanton need in her voice palpable. "Y-you've never actually wanted that...you like...losing control...for me..." The words was punctuated with moans. We were both right on the edge.
I opened my mouth to respond, but couldn't.
She kept going. "You're such a quick...cummer..."
And then I was done, and as a result, so was she. I felt the orgasm envelop me. Moaning, I started bucking my hips, my cock pulsing. She collapsed on top of me, legs shaking, but continuing to pump my length.
Panting, a few moments later, she lifted her head off my chest to make eye contact with me.
Her eyes sparkled. "Fuck. Feeling how much I turn you on was amazing. I loved that."
She hesitated. I had never heard her hesitate before.
But then she continued, the same sparkle in her eyes. "I love you."
"I love you too."
