Jay Friday
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The Masseuse (Ch. 21-23: Contests)
🕑 Added 2025-07-03 19:00:07 +0000 UTCAuthor's Note: If you haven't read this before, I've written four different versions of Chapter 24 -- four different endings for the story. That's why Chapter 23 ends where it does. I'm going to shoot for editing and posting one ending a week for the next four weeks, so you won't have to wait too long for the ends.
CHAPTER 21
I couldn't focus at work for the rest of the week.
First, Natasha and I were hashing out the terms of an investment in the company that held her proprietary technology. I was trying to be responsible and not put in all the liquid cash I had -- this felt like such a sure thing, and she was offering really favorable terms, but obviously nothing is a sure thing. So I was agonizing over it.
Brittany was also blowing up my phone nonstop. When I hadn't responded on Monday, a barrage of texts came through over the course of the next few days.
Brittany: I don't like to be ignored, Rick...
When I didn't reply to that one, she sent another.
Brittany: Seems like you're forgetting that I know stuff you wouldn't want me to share with Emma or Claire...
Fuck. I tried to remind myself of what Natasha had said: this was a secondary problem. I ignored her.
Brittany: Did you block me again? I might have to tell Claire about that...and who knows what else we'd talk about...
I hesitated, mulling it over, and then texted her back. Didn't block you, just busy with work this week.
Brittany responded almost immediately: Aw, sounds stressful. You should let me help you relax.
My phone pinged again, and a video came through: Brittany, sloppily sucking on two of her fingers while she made eye contact with the camera and moaned. It was hard to think of anything besides the last time I had seen her with that expression on her face -- when I had started cumming all over her. How obsessed she had looked with my cock. I was hard.
I didn't like her, but it was admittedly tempting to...blow off some steam. But I decided I had already made things complicated enough. I needed to stay focused on Friday.
I replied. Sorry, can't this week. Maybe sometime soon, though. Was it fucked up if I strung her along until after Friday so I could see how things worked out with Claire and Olivia? I decided it was fucked up...but only a little, given how she had treated me.
Brittany: Mmm, okay, but don't keep me waiting too long...
That seemed to mollify her, and she stopped texting after that. I was relieved. For now.
That just left my massage appointment on Friday, which entirely consumed my thoughts. I was excited -- both Olivia and Claire seemed excited -- but it also felt like I needed to take Natasha's advice: do whatever you need to do in order to figure out what you actually want.
When she had said it, that felt like brilliant advice. As Friday loomed closer, it felt useless. I liked them both. What would help me figure out what I actually wanted?
I didn't know. But it did make me curious.
I texted Claire and Olivia -- sending separate texts, but saying the same thing: How do you want this to go on Friday?
Claire responded first.
Claire: Well, I liked watching you and Olivia last time...but I want to participate this time...especially now that you know I can be dominant, too...
She sent a photo. Her, looking down at the camera, a bratty smirk on her face.
Well, that was pretty hot. Oookay.
Olivia responded at almost the same time. First, she texted an eggplant emoji, a sweat droplets emoji, and a peach emoji.
That seemed pretty hot too.
Then she texted a message.
Olivia: I mean, you get what you really want for your 40 seconds. But the rest of the time, I'm gonna be running the show. I've got a few ideas...it's going to be so fucking hot. Curious how long you'll last for both of us. I'm guessing it's not gonna take that long, big guy.
Jesus. My phone pinged again.
Olivia: Also...afterwards, what I want is for you and I to go out for dinner or something after the appointment, like last week...if you want to, that is.
I thought back on our date last week. It had been really nice after the massage appointment to just...hang out with her. And...maybe we'd get the chance to do something else...It's a date.
The following day, my phone pinged again.
Claire: hey...wanna grab dinner after the appointment on Friday?
Well, fuck. I tried to think of a way not to tell her. But I decided being honest was best. Sorry, I already made plans with Olivia. Saturday?
She sent a selfie: her, pouting, with the camera at an angle that put her cleavage on full display.
Claire: Aw, too bad...maybe on Saturday. Let's see how Friday goes first.
That was the first time Claire hadn't said yes. It felt kind of...weird. It made me nervous about Friday.
Friday rolled around. I kept pulling up the various photos Claire and Olivia had sent me, imagining what this might be like. I re-read Claire's last comment over and over. The situation felt...off. There was this sense of...friction, between them.
I knew it was because of me, presumably. I tried to keep repeating Natasha's advice. What would help me to decide what I wanted? Nothing brilliant came to mind besides continuing to date them both.
---
I opened the doors to the massage parlor. Claire and Olivia were both by the front desk, Claire sitting behind it and Olivia lounging against it. They were wearing, I realized, matching outfits. Black crop tops and matching black tennis skirts. Olivia was in front of the desk facing me, and so it was easier to see her -- strong, tanned legs visible below the skirt, abs above...fuck, she looked good. Claire leaned forward as I approached and I was treated to a great view of her cleavage as well.
They both giggled; I knew my staring was probably obvious. I tried to regain my footing. "H-hey, you two..."
"What do you think, Rick?" Olivia gave a little twirl. I caught a glimpse of her ass, which looked great in the short skirt. "Quite the coincidence that we came in today wearing the same outfit..." Olivia had a grin on her face.
"Aw, Rick, you're staring..." Claire grinned up at me from the desk, her tone the same bratty, slightly ditzy tone she had used when I had been at her apartment last week. "Olivia and I had a little chat earlier this week and...coordinated a few things to make sure this appointment is especially fun." There was a bit of a competitive edge to her voice.
"Anyway, you can head on back to our usual room and disrobe to the level of your comfort, Rick. Claire and I will be coming shortly." Olivia glanced at Claire and winked at her. Claire giggled.
I realized I was still staring, mouth slightly open. I closed my mouth. "Uh, o-okay..." I hadn't expected them to coordinate.
"Just...a few things before you go...we wanted to make this interesting..." Claire stood up from behind the desk, and came around to stand next to Olivia. The top was impossibly tight on her tits; I could see her nipples standing out through the fabric. She probably wasn't wearing a bra. She flipped her hair, done up in a ponytail, over her shoulder.
"We thought a little contest between us might be fun..." Claire said, teasingly. "And after you told me you and Olivia were going on a date tonight...I thought you might be willing to wager that. If I win, you go on a date after this with me instead. If Olivia wins, you go with her as planned."
I blinked. "Uh, if Olivia's okay with it..."
Olivia nodded. "I mean, I'll win. I'm pretty good at this, and I know what makes you tick..." leaning against the desk, she slowly crossed one leg over the other. I stared.
"Okay...what are we betting on?" I was trying to rapidly recalibrate my sense of what this appointment was going to be like, and failing.
Claire leaned in, whispering to me. "We're both going to tease you. And whoever makes you cum, wins."
Olivia giggled. "So all you have to do is try to hold back. I mean, if you can control when you cum, you basically get to decide who you go on a date with, and you get an orgasm. You're so good at self control, I'm sure it'll be no problem."
I blushed.
Claire smirked. "I dunno, Olivia...I think he's gonna bust for me pretty quick. Did you see how he was looking at my tits earlier?"
"I did..." Olivia mused. "This'll be interesting...but I think we've talked enough..." Olivia stepped up close to Claire, and put one hand on the small of her back. Claire let out an intake of breath at Olivia's touch. "Let's let Rick go and disrobe to the level of his comfort." Olivia winked at me.
"See you in a minute, Rick."
Fuck.
---
I was lying on the table, face-up, a towel over my dick. I heard the door open and glanced over just in time to see Claire and Olivia both entering -- and to see Olivia turn off the lights, Claire giggling.
There was a little light coming through the small window in the door, but not really enough to see by -- just enough to make out dim shapes. I could hear the two of them moving around the room, but not really see anything distinct...
So I was just about startled out of my skin when a moment later, Olivia's voice purred in my ear. "Just let me know when you want to use those 40 seconds. Totally up to you. But otherwise...you're not really going to get a say in what's happening..."
Claire chimed in, voice bratty and plaintive from somewhere near my feet. "I want to see his cock, Olivia. We can't see it with the lights off."
Olivia's voice was amused, teasing. "You're kind of obsessed with his dick, aren't you, Claire."
"It's just so big...thick...I like the way it looks..." I felt one of her hands slide up my thigh, under the towel. I realized I was already rock hard.
"Mmm. Don't touch it yet." Olivia's voice was admonishing.
"You're just worried I'll make him cum and win in like, two minutes." The words came out brattily, and her hand wrapped around me in spite of Olivia's instructions. I let out a moan -- I could tell it was Claire's hand. Petite, barely wrapping all the way around my shaft. She started to stroke me, slowly.
"Claire, you need to behave..." There was the sound of movement, rustling, a gasp from Claire, and a satisfied snort from Olivia. "Wow, I can't believe you're this wet already, Claire..."
Claire moaned, and I felt her let go of my cock.
My cock twitched. What was Olivia doing?
"Rick, you've gotta feel this..." I feel one of Olivia's hands on mine, guiding me between Claire's thighs. She was sopping wet. I slowly ran my fingers over her; she moaned. Fuck. I felt my cock twitch.
"W-we're supposed to be teasing Rick..." Claire was breathing heavily.
"Mmm, we are...but you're being a brat, like I said. Are you ready to behave?" Olivia's voice was still amused.
"I-I can be dominant too...we don't only have to follow your rules..." Claire's voice was bratty, sullen.
"Oh, I see. You don't understand that while we're in this room, I'm in charge. Let's just make that totally clear, then." Olivia's voice had an edge to it, now.
I heard her move across the room, and the lights flicked back on.
I blinked at the sudden brightness; it took a few seconds for my vision to return. During that time, I heard the sound of a brief struggle, and Claire let out a little gasp.
When it did, I gaped at the sight before me. Claire was bent over the table above my midsection, her face almost touching the towel over my dick. Olivia had a fistful of Claire's hair with one hand, bending her over. Claire was twisting to look back at Olivia, a look of astonishment and arousal on her face.
In Olivia's other hand was a thick, black dildo. "This is one of Natasha's older products -- not a lot of tech behind it, but it gets the job done...and I thought it might be useful because it's almost as big as Rick..." with a deft motion, she slipped it in between Claire's thighs.
"f-fuck...W-what are you doing..." the words came out of Claire as a half-gasp, half-moan.
"Putting you in your place. Which I think is what you want anyway." Olivia had a satisfied smirk on her face. "Rick, take that towel off so she's got something to look at while I fuck her with this."
Jesus. I was frozen for a moment, taking in the sight of Claire, bent over, looking back at Olivia. Olivia was adroitly starting to move the dildo in and out of Claire, slowly. Claire bit her lip and made eye contact with me. I was rock hard. I slowly pulled the towel away.
Claire stared at my cock, inches from her face, moaning. Whatever bratty demeanor she'd had was clearly...well, getting fucked out of her.
"Is that what you wanted to see?" The amused note in Olivia's voice persisted as she worked the dildo in and out of Claire, one hand still holding her by her blonde ponytail.
Clare opened her mouth to respond, but ended up just moaning some more. Olivia was picking up the pace, sliding the dildo in and out of her. Claire settled for just nodding, a look of wanton abandon on her face as Olivia fucked her with the dildo.
"Rick, why don't you stroke that big dick for Claire. Match my strokes." I did as instructed. I was leaking precum. Watching Olivia dominate someone else for a change was...incredibly hot. Olivia let go of Claire's hair and grabbed her ass with one hand instead, picking up the pace. Fuck. I had just started pumping and I could already tell I wouldn't last long with this happening in front of me.
"Mmm, it sounds like you're having a good time, Claire...are you imagining that it's Rick's big dick doing this to you?"
Claire nodded, breathlessly moaning.
Olivia smirked. "Has he ever fucked you like this before?"
Claire shook her head, and tried to form words. "N...no..." Fuck, seeing Claire totally out of control was hot. I wasn't going to last much longer.
"Huh. Why not?" Olivia asked, innocently. My face burned, but I kept pumping my cock quickly, the way Olivia was fucking the dildo in and out of Claire.
Claire was moaning uncontrollably now, but tried to form the words. "H-he...hasn't been able to...last...oh, fuck, keep going, yes..."
Olivia paused, and then slowed down. "Ohhh..." she said, as if a lightbulb was going off. "He cums too quickly? Well, I don't think it's really fair for you to be fantasizing about Rick's dick if he couldn't fuck you this way..." She smirked. "And Rick, you're supposed to be matching my strokes. And now, I'm not stroking. So you should stop pumping."
She slowly pulled the dildo out of Claire, and reluctantly, I pulled my hand away.
I realized that, without meaning to, I had gotten right on the edge of an orgasm. It made me realize that the stakes here were...well, perhaps kind of significant. Whether I was actually in control of myself or not, I could imagine that probably both Claire and Olivia wanted to be the one to make me cum. Whoever I didn't cum for was likely to be pissed. I tried to calm myself down. Who...who did I want to cum for? Who did I want to date?
"W-why did you stop?" Claire made a frustrated, needy sound.
"To remind you that I'm in charge, Claire. I'll make sure you finish later...if you're a good girl." Olivia smiled wickedly.
Claire stared at her, openmouthed, the fight between her pride and arousal obvious on her flushed face. "W-we said we'd tease him together..."
"We will. But you were trying to make him cum right away. There's way more teasing to do. Don't worry, you'll get your chance to win the date with him." Olivia set down the dildo to one side and started to put massage oil on her hands, eyeing me. "I mean, look at him. He looks like he's ready to pop already. It could happen for either of us."
Claire glanced at me, taking in my erection and heavy breathing. She giggled, seeming to regain some of her composure. "Yeah, you're right. Did you like watching Olivia fuck me with that dildo, Rick?"
"Y-yeah..." I stammered the words out. I felt completely ill-equipped to handle the constantly shifting dynamics.
"I could tell...I was watching your dick leak while you pumped it in front of my face...if you had cum it would've gotten all over my face..." Claire bit her lip. I blushed -- thinking partly of Claire, but partly of Brittany. Fuck.
"Mmm, I think he's embarrassed by how close he was to that happening..." Olivia giggled. "So here's what's going to happen next. I've always been curious whether you're a tits guy or an ass guy. I don't think you can handle us touching you right now, so you're going to jerk off while we tease you. A minute from me, then a minute from Claire. We'll do this for...let's say, three rounds. If you cum while one of us is teasing you, then that's it; one of us wins the bet."
She had a small smile on your face. "But you can stroke as much or as little as you like. We're doing visual teasing and talking only. So you're in complete control, really. You get to decide when you cum, and who you cum for. You two ready?"
Claire nodded. I nodded, sitting up. This sounded easy, I just needed not to...
Olivia stepped right up in front of me, and then turned around, running her oiled-up hands up the back of her thighs, and lifting up the tennis skirt. She wasn't wearing anything underneath. I stared, openmouthed, at her tanned ass as she grabbed it with her hands, massaging oil into it.
Then she started...well, twerking in front of me.
She could really move. I watched her oiled ass shimmy and bounce. My hand -- as if it had a mind of its own -- drifted to my cock, and I started pumping.
"Mmm...are you imagining what it'd be like if you could actually last long enough for me to give you the ride of your life?" Olivia giggled, staring at me over her shoulder.
I nodded. I was pumping slowly, much slower than her bouncing, but I could still feel my orgasm building. I wasn't sure I cared. I was almost mesmerized.
She started whispering. "You still have those forty seconds where you can tell me to do whatever you want...maybe what you want is for me to sit on that big dick and ride you until you blow a huge load..." she bit her lip.
It was what I wanted. I could feel my orgasm closer and closer. I opened my mouth, but she kept talking. "Or maybe you want me to grind on you while we're dancing at some club, the way Brittany did..."
I heard a sharp intake of breath from Claire. "Brittany did what?"
Olivia glanced at her and at me, trying to read our expressions. "Uh, do you know Brittany or something?"
Claire said, "She's my roommate." Her tone was flat. Olivia's eyebrows went up in surprise.
I stopped stroking, trying to defuse the situation. "I told you she was friends with Emma, Claire. She, uh, found out how big I was a few months back, while Emma and I were together, and was grinding on me at a club one night when Emma was in the restrooms. But that was it." That night, anyway.
Claire looked a little mollified. "Okay...I guess...and hey, Olivia, you've had your minute now. My turn."
I could see Claire was still...thrown off. She didn't like learning something new about Brittany and me. Fuck. She didn't know the half of it.
Olivia made eye contact with me, a questioning look in her eyes -- maybe wondering why I hadn't told Claire before now -- but didn't say anything, just stepping to one side.
Claire stepped in front of me, looking up into my eyes. "We'll talk about that later..." she said the words gently enough.
"Right now, I want to talk about something I've noticed..." as she spoke, she was fondling in her tits, squeezing them through the crop top. I couldn't help but stare; I could see her nipples were rock hard through the thin material.
"Wh-what?" I found my mouth was dry.
Talking about Brittany had taken me off the edge of an orgasm, but Claire, inches away, squeezing her big tits in front of me, had my hand drifting toward my cock again.
"Well..." she slowly stripped her top off, pulling it over her head, and letting her big tits fall free in front of my face. "It seems like...you cum really quick any time my tits are involved..." she bit her lip. "Do you think you'll ever be able to handle them?"
This wasn't her bratty act; she asked the question in a small voice, as if she were curious, almost embarrassed to have to ask me. I was staring at her tits and didn't respond immediately.
She picked up the massage oil and started oiling them up. "I mean...the first time we were together...I titfucked you, and you lasted like, no time at all...but maybe that was just because it was our first time..." she said, squeezing her tits as she rubbed oil into them.
Olivia giggled. My cock surged. Fuck, was she really going to recount every time we'd been together? In front of Olivia. I gave myself a slow pump, staring at her hands working oil into her tits.
"And then...the next time...I thought you were going to really pound me with that big dick...but...you put your hands on my big tits, like this..." she gave them a demonstrative squeeze, and I felt the blood surge to my cock, throbbing. "...and then you came, like, ten seconds later...so it doesn't seem like it was just because it was your first time with them..."
Fuck. This wasn't good. Or rather, it was too good. I had to stop stroking. But it was hard not to want to stroke, those big tits right there...
Olivia murmured, "Wow, Rick." I could hear the amusement in her voice, which only made it hotter.
Claire continued. "And...I was telling you about that guy I hooked up with in college...who came right when he touched my tits...." she bit her lip, pinching her nipples. "And you were so excited you didn't even touch them, you just blew your load...honestly, maybe even faster than the time before that..."
I was stroking faster now. Claire continued to pinch and fondle her nipples. "And then...I told you about how I can sometimes make myself cum just from playing with them...and you couldn't even last long enough for that to happen..." She was staring deep in my eyes, expectantly.
I was done. Staring, pumping, I could tell I was going to cum in only a few more strokes.
"Time's up, Claire." Olivia said it, grinning, and I felt the orgasm recede a little at the realization that the minute was up. I stopped pumping. Claire pouted and stepped away. Fuck. That had been really close. I tried to regain composure.
I knew that this was an opportunity, that I should be trying to control myself. Who did I actually want to go on a date with? Natasha's words rang in my head again. What did I actually want? But I couldn't really think straight as Olivia stepped back in front of me. Right now, all I wanted was to cum.
Olivia made eye contact with me, as if considering how to use her time. She had a gleam in her eye. "Did you like hearing about Claire's big tits making some other guy blow his load in no time?"
I blushed. "I, uh, I guess..."
"Mmm. It certainly sounds like you did. So why don't I tell you about a time a guy lost his load for me in a super embarrassing way. This was, I dunno, probably four or five years ago...I was in college, and my ass didn't look quite like this yet..." she stood in front of me, turning, and gave her ass a little slap, making it jiggle. I stared, and gave my cock a slow pump. "...but it was still pretty fucking good."
"I was dating a guy, Greg," she rolled her eyes, indicating her current opinion of Greg. "He was fine, I guess, but what was really the most fun about Greg was his roommate, Steve. Steve was a nerdy guy -- skinny, glasses, never much luck with girls. I loved teasing Steve. It was obvious I was one of the hottest girls he had ever been around -- any time we were in a room together he couldn't take his eyes off me. And I could tell he liked one part of me in particular..." she grinned, and gave her ass a shake.
"Anyway, I was always looking for ways to tease Steve, and one weekend, Greg, Steve, me, and some friends of ours decided to go hiking. Greg was driving, and there were like, seven of us -- not enough room for everyone to take one car to drive to the trailhead. So I said the girls ought to sit on the guys laps..."
She bit her lip. "Everyone was fine with that, but, well, I couldn't sit on Greg's lap with him driving. But I said I was okay sitting on Steve's -- after all, we were just friends, and he was Greg's roommate, so there was no problem, y'know? And I don't think Greg cared -- Steve was not exactly a sexual threat, if you know what I mean."
I caught myself nodding as I stared at her ass, imagining where this was going. I was pumping a little more quickly now, putting myself in Steve's shoes, imagining the prospect of Olivia sitting in my lap.
"Well, I climbed into the back seat and sat down on top of Steve..." as she spoke, she stood in front of me, bending over as if to sit on my lap, but hovering, her oiled ass an inch or two above the head of my cock.
"Did he...was he hard?" I practically whispered the words, staring at the throbbing head of my cock and her perfect ass.
She smirked. "At first I think he was too nervous, but I did a little strategic wiggling..." she wiggled as she spoke. "And, well, I got a rise out of him. He wasn't nearly as big as you, but I could tell he was having a good time with my ass on his lap."
I was pumping, staring openmouthed as she wiggled her ass above the head of my cock, imagining her teasing some nerdy kid.
"Mmm, you're such a tease, Olivia..." Claire giggled, and I heard her let out a soft ah. I glanced over...she was playing with her tits, still squeezing them. Fuck. She thought it was hot too. I turned my attention back to Olivia expectantly.
"Well, I kept teasing him like that for fifteen or twenty minutes. He was rock hard. Then we turned onto a gravel road that led to the trailhead, and it got really bumpy..." she giggled, shaking her ass above my cock. I was pumping faster now -- not deliberately, but my brain was on autopilot. I could feel the orgasm building.
"So...I took his hands, and put them on my hips, and leaned back and said 'I don't have a seatbelt, so you'd better hold on tight...' And I mean, I could practically feel him throbbing against me. He started kind of...using his hands to grind me down against his dick." Olivia grinned, clearly enjoying the memory.
I kept pumping. "Did...did you make him cum?" I realized I was right on the edge, that we were probably less than ten minutes into this massage appointment. But that didn't matter. This was too hot.
Somewhere, in the back of my mind, was the knowledge that when I came did really matter. That cumming for Olivia would have consequences for Claire, and vice versa. But right now -- I didn't care. The combination of the two of them was way too much for me, and it just so happened that Olivia was talking. I had to cum, and I wanted to do it now.
She laughed. "Oh, yeah. A few minutes of my ass bouncing against his dick was way more than he could handle. It was a pretty noisy ride and I didn't think anybody else could hear us, so eventually I leaned back and whispered you can finish if you want, right in his ear...." she leaned back, looking at me expectantly.
I moaned as I crested over the edge, and started spraying a load all over Olivia's ass.
"...and he moaned and started cumming in his pants. He had to try to clean himself up in one of those shitty park bathrooms," she finished, looking back at me smirking.
I was still pumping onto Olivia's ass when Claire let out a pouty little whine.
"Aw, no fair, he came so fast. What about best two of three? I think we have time..."
Olivia glanced at her, at the clock, at my load, and finally, at me. "Sure, Claire." She grinned. "Let's clean up and give him a minute -- we'll see if he lasts longer the second round. Somehow...I doubt it."
Fuck. I inhaled deeply, trying to take a minute to gather my thoughts. There was a bit of a knowing look in Olivia's grin. Claire was biting her lip and staring at my cock, which was just starting to soften.
I agreed with Olivia -- I didn't think the second round would take long. But, I told myself, I could at least be in control of the outcome.
Couldn't I?
CHAPTER 22
Five minutes later, I felt reasonably recovered. I was a lot less on edge, having cum once. I was cleaned up, and so was Olivia.
I had spent the intervening time trying to figure out who I wanted to win this little contest.
I considered Olivia first. If she won this round, she'd have two out of three and have won it all -- I'd keep the date I had already agreed to with her. We had a great time last time; I was sure it'd be fun.
Claire...I felt kind of bad for. She had wanted to go on the date with me, Olivia had just asked first. And...I felt guilty when I thought about her and Brittany. About me and Brittany. I'd try to let Claire win, I thought. It wouldn't make up how...badly I'd behaved, but a date with her without any weirdness with Brittany would be a good start. It would give me a chance to explain things to Claire.
And...I still had time to reconsider if Claire won this round, since they'd be tied after this round, so there'd be a third. I felt good about that decision.
That resolved in my own mind, I turned my attention back to Olivia and Claire, who had started arguing almost immediately, and were still going.
"No, I went first last time," Olivia was saying. She had a reasonable, if steely, tone in her voice. "So you get to go first this time."
"That's bullshit, Olivia, and you know it. He just came, so whoever goes first is basically just warming him up!" Claire, on the other hand, was petulant.
"Ladies, please..." I tried to put a smooth, girls-lets-not-be-fighting-over-little-old-me tone into my voice.
I regretted my choice immediately. Olivia glanced at me, clearly astonished at my audacity, and opened her mouth to say something that I'm sure would've put me in my place. But Claire glared at me, and spoke first.
"I don't want to hear it from you. I'm expecting to hear all about whatever you've done with my roommate. I can't believe you told me she was just Emma's friend or whatever. You're being so fucking weird about it. And you came for Olivia just now instead of me on top of that..."
I winced. I felt really guilty. Not for not mentioning that I had danced with Brittany one time when Brittany was wasted...but because earlier that week I had cum all over her roommates face. In my defense, I had been blackmailed...but the fact that she even had blackmail material was kind of my fault, too.
Olivia shrugged. "Look, Claire, you seem pissed. This is supposed to be fun. We could always call this off and continue it next week..."
"Oh no. I said best of three and I meant it." Claire was looking at me with increasing annoyance. I didn't blame her.
Claire took a deep breath, obviously trying to get herself under control. She eyed my cock, which was -- remarkably -- still soft. The guilt I was feeling was more effective than a cold shower.
Claire considered. "Tell you what, Olivia. I'll go first if you give me three full minutes. That gives me some time to get him warmed up again. After that, we tradeoff every 60 seconds."
I paused, taking stock of how I was feeling. "That seems--"
Claire just held up her hand, palm facing towards me. "Zip it, buddy." Wow, she was...actually pissed.
Olivia considered, and then nodded, slowly. "Okay, that's fair. 3 minutes for you, then we trade off every 60 seconds. Let's talk ground rules for this round: touching is allowed. But no penetration."
Claire nodded her agreement. "What about oral?"
Olivia eyed me, smirking, and licked her lips. My face heated, and I felt my soft cock reacting to the implication. The one time she'd given me a blowjob, I hadn't lasted long at all. She pursed her lips. "Tell you what...you decide, Claire."
Claire mulled it over before grinning. "No oral this round."
Olivia shrugged. "Fair enough. Start when you're ready."
Claire started massaging oil into her big tits, getting it all over her hands and breasts. My cock twitched at the prospect. I remembered the titfuck she had given me. She really knew what she was doing. "Helping" her win would be no problem. This would probably take way less than her initial three minutes.
Claire stepped up in front of me, looking down at my cock as if considering how to use this time. "You know, I think that's the first time I've ever really seen you soft...it's still so big..." she said the words in almost a whisper. She reached down, caressing it.
"It...it's not gonna be soft for long..." I said the words softly. Her touch felt so fucking good.
Her tone was firm, but quiet. "So...we've gotta resolve this Brittany thing, Rick." She bit her lip, even as she continued to fondle my thickening length.
"I, uh, Claire, it wasn't like I was trying to, y'know, hide anything..." I felt myself getting red. And hard.
She just kept talking as if I hadn't said anything. "I mean, I know she's a hottie...she's got guys in her room all the time...and you told me she knew you and Emma..." she mused. She leaned over more. Any closer and she'd be smothering me with her tits.
I swallowed, now fully hard, simultaneously aroused and guilty. Claire added her second hand. She was so petite that her hands barely wrapped all the way around my shaft, and she probably could have fit four of them along my length. I stared down as she pumped me. Even though I had already cum once, this was hot.
"I just feel like you're not being honest with me, and I don't understand why. I don't know Brittany well, but we've talked about a few things, Rick. And Brittany has a very particular fetish...one that you'd probably be a good fit for..."
"Ooooo. How interesting, Rick. You didn't mention this to me..." Olivia's voice was intrigued.
Oh fuck. I tried to school my expression to be carefully neutral. "D-does she?"
Claire was staring at me, leaning forward. I couldn't look at her, though -- I was staring at her hands, working my thick shaft, and her big tits, which were hanging just an inch or two above my cock. They looked so soft and inviting...
"Are you telling me you don't know, Rick?" She frowned a little.
I really didn't want to have this conversation. Fuck. "C-Can we talk about this another time? Uh...maybe if we go on that date?" Maybe I didn't want Claire to win this round.
She frowned deeper. "I mean...it feels like you're trying to hide something from me, Rick. And I don't like that." She was pumping me faster now. I glanced up at the clock. It had been just over a minute. Fuck, she had two more minutes of running the show...and I could feel my orgasm building.
But she paused, as if considering her approach, and then her demeanor shifted, becoming less angry, more teasing. "Okay, sure, if you don't want to talk about it right now, we don't have to, Rick..."
A breathless, slightly ditzy smile formed on her face. Her cheerleader, mean-girl smile. My heart started beating even faster.
"In that case...I wanted to keep talking about what I was asking earlier...do you think you'll ever really be able to last for my tits?" She bit her lip, as if concerned, and leaned forward a little, the head of my cock nestling between her tits.
"Claire, I've been trying..." but I trailed off into a moan as my cock touched her tits.
She gave me a small, knowing smile. "I know...I can tell. You're trying so hard. But Rick, I really want you to make me cum. I want to get fucked hard...the way Olivia was fucking me with that dildo earlier, you know? But...you keep cumming so fast..." She pouted.
I was definitely blushing now. "I--c'mon, Claire..." Did she have to do this in front of Olivia, too? During this weird contest they had come up with? The way she was teasing me, the humiliation of it...I was starting to get close.
She had both hands on my cock, still pumping, the head and first inch or two of my cock moving in and out of the valley of her cleavage. "Brittany doesn't have tits like these, does she?" Claire smirked as I shook my head. "Neither did Emma, I bet...neither does Olivia..." she glanced over at Olivia, who was uncharacteristically silent, studying my face and reactions.
She shifted forward, putting more of my cock between her tits and shortening the strokes she was making with her hands. "But hey, maybe you'll be able to last this time...you came once already a few minutes ago..." Claire smirked, wrapping her tits more tightly around my cock with one hand. I moaned. I couldn't help it. My dick was big -- the head was poking out the top of her cleavage, almost jabbing her as she looked down at it. Her tits were big enough to wrap around almost my entire length. One of her hands was wrapped around the base, where my cock met my balls, pumping. I was slick with oil, and so was she -- I smoothly glided up and down between her hands and breasts.
I stared back, watching as she fucked my cock with her cleavage. The sight was incredibly erotic. I felt myself building quickly towards orgasm, but that was the point -- to let Claire win this round. It felt so good to not be trying to last, for a change, to just let her drive me to cum. Another ten or fifteen seconds and I'd explode -- I looked up at the clock. Lots of time left in Claire's three minutes. She'd win the round.
She stopped.
I let out a strangled, frustrated, moan, and looked at her.
She had a small smile on her face. "Tell me what's going on with Brittany, or I'm not going to keep going."
A rising sense of panic overtook my arousal. "Claire, there's nothing..."
"Rick..." she gave me a pitying smile. "You're a bad liar, and you're an even worse liar when you're aroused. Besides that, I know Brittany's got a fetish for big dicks cumming on her face. There's no way she'd give up a shot at you if she knew you were big."
She considered. "You know what? Fine. Don't tell me. But I'm going to win this contest, and make you go on a date with me -- but the "date" is just going to be coming back to my apartment after this and figuring things out with Brittany. I know she's home tonight, and I'm done with your bullshit, too. The three of us can get in the same room and talk about it."
Olivia gave a little, surprised, hmmm in the background. But I was focused on Claire. Fuck. I really didn't want to do that. "Look, yes, I know about her...fetish, but---"
Her mouth tightened. "Right. Okay. So you were definitely lying before when you pretended not to." She looked in my eyes, and her voice lowered to an almost-threatening whisper. "You're going to cum for me, and then I'm going to win the next round, and we're going to figure this out."
Fuck. I had never seen Claire like this. I did not want to "hash it out" with Brittany and Claire at the same time. I tried to calm myself down. I glanced at the clock. I only had to last another 60 seconds, and that would give Olivia two rounds. I could do that. Then I'd let Claire cool off...in a few days, she and I could talk about it separately.
"Anyway...I know how to get you off..." Claire was all syrupy, bratty sweetness again. "Like I was saying earlier...I really want to get fucked by that big cock, Rick, the way I need...but I don't know how many dates I want to go on if you can't even last 30 seconds between my tits..." she said it, teasingly, pumping up and down.
Fuck. Her voice...those big tits, slick with oil...and I had already let myself get so close to the edge...pulling back now was going to be hard. I fought to keep control, not saying anything.
"Mmm...I do love that I can look down and see the thick head of that cock while its between my tits..." she stared down at it, almost cross-eyed as she bounced her tits up and down around it. "My tits swallow up most guys...but not you..."
I was helpless, looking at her enjoying pleasuring my cock. I could feel a tidal wave of an orgasm heading towards me.
"Aw...I can tell you need me to slow down if you're going to last any longer...but if I have to slow down while I'm titfucking you, how will you ever fuck me the way I want?" she said the words plaintively.
I could feel the wave about to crash over me. "Claire, I..." I wasn't sure what I was going to say. That I was sorry? To ask her to slow down? That I wanted to tell her the truth?
She leaned in close, her voice a whispered, sultry, hiss. "This is why Emma broke up with you, huh? Because you could never fuck her properly? I bet Brittany knows all about it too, maybe the three of us can talk about it on our date..."
It was all too much -- the shame, the guilt, the arousal, how good her tits felt, the idea of her and Brittany comparing notes on me, of talking about how quickly I cum and what Brittany and I had done. I groaned, thrusting my hips against her chest, and started cumming. She kept pumping my cock up and down against her, smearing it everywhere.
Olivia pursed her lips. "Uh, well. That was fast, given that you just came ten minutes ago. I guess we're tied then, Claire."
Claire's lips curved up in a smile. "Yeah. Winner takes all in the next round."
I slumped. Fuck.
CHAPTER 23
Claire threw a robe on and left the room, saying she had to use the restroom. But it looked more like an excuse to take a second to gather her thoughts.
Olivia blew out a breath, giving me a serious look. "Are you...sure you want to keep doing this, Rick? Claire looks like she's having a shitty time, and, uh...I think the stakes feel...increasingly high, here. She's gonna be pissed if she doesn't win that date...and I have to admit, I'm gonna be pissed if I don't win it."
She was right, but I didn't see an alternative. "I think stopping now would be even worse," I confessed. "Claire's already feeling like I'm hiding stuff from her..." I sighed. "And I am, Olivia."
She bit her lip. "Yeah, I could tell. She's right -- you're a shitty liar, Rick. You should just be honest about...whatever it is."
I nodded. "I will. Give me a minute when she comes back in and I'll try to set the record straight. I feel awful."
Olivia gave me a small smile. "You really like her, huh?"
"I...yeah..." but I trailed off. "But I really like you too, Olivia. I...I was excited when you wanted to go on another date."
She gave me a much bigger smile. "I was excited when you said yes."
I ran a hand through my hair. "I...y'know, I think...I need to make a choice. This...well, it started off fun, but it feels like it's going off the rails, and I feel responsible."
The smile on her face turned sad. "So...what...who...are you going to choose?"
I didn't know.
My face must have showed it, because she giggled. "Well..." she said, stepping right up next to me, to whisper in my ear. "I had better make sure that this next round reminds you of what you'd be choosing, if you picked me." I felt blood flowing to my cock as she nipped at my ear.
She stepped away. "It makes me sad, but you're right. You've gotta make a choice."
She glanced at the door as Claire walked back in.
Claire took a deep breath, and gave me a look that was all disappointment. She opened her mouth, clearly about to lay into me.
But I held up a hand, gently, and said "Hey, look, Claire, I'm...I'm sorry. Brittany...well, it's complicated. But the long story short is that I saw her masturbating the last time I was with you at your place, she blackmailed me when I didn't want to tell you, and I..." My face heats. "I, um...helped her with her fetish. I didn't want to...it just kind of happened."
Claire blinked a few times. "I...I thought as much." Now that I had admitted it, she seemed a lot less upset. "Why didn't you just tell me? We're dating, not married...I just wanted to know what was going on..."
I sighed. "I didn't want to upset you; she's your roommate and it felt fucked up. But I should've told you. I don't care at all about Brittany; I just got carried away. You know how I feel about her...remember how upset I was when it seemed like she might work here?"
Claire nodded, thoughtfully.
Olivia had cocked her head and was looking at me. "Uh...I'm sorry, this is the Brittany who nearly worked here?"
I nodded, realizing I hadn't really filled Olivia in either. "I, uh...I went to Natasha and asked her not to hire her. But she had already decided not to..."
I trailed off as I realized Olivia was pinching the bridge of her nose. "You...really have to work on your communication skills, Rick..."
I felt a little sheepish. "I...yeah, I guess you're right."
Olivia took a deep breath, clearly trying to re-rail the situation. "Okay. Claire, do you want to keep playing? No harm in calling things off. Things feel..." she considered, choosing her words carefully, "...a little higher-stakes than it was when we started."
Claire nodded. "Let's finish the game. If I win...Rick and I can talk about this on our date."
Olivia hesitated. "Look, Claire...I still want that date with Rick. I'm not going to compromise on what I want just because you're pissed at him and need to have a conversation. I'm gonna try to win the next round." Her voice was kind, but firm.
Claire nodded. "Me too. Anyway, he's cum twice -- he's quick, but even he ought to have enough control to influence who wins here. I think how this goes will be...telling."
They both looked at me, a mix of curiosity and amusement written on their faces. I looked back at them.
Claire was on the left. Her blue eyes were a little puffy, I realized -- she might've been crying in the bathroom. Shit. She had put one of the terrycloth robes the spa kept available for clients on -- it was a bit long on her petite body, and it hung open in the front, revealing the tempting inner curve of her tits, so large for her frame. I made eye contact with her. I mouthed the word sorry at her. She nodded, and bit her lip.
Olivia was on her right. Taller than Claire -- almost as tall as me. Her long dark hair was in a ponytail that ran down her back, and the skirt and crop top revealed an astonishing amount of tanned skin -- shoulders, abs, and long, lean, thighs and calves all left bare. The way she filled out her skirt hinted at her round ass. Olivia stared directly back at me, and gave me a knowing smile -- like she knew just what I was thinking. I felt my face redden.
I realized...I did know what I wanted, after all. For the first moment, I felt a real sense of clarity as I considered both of them.
I opened my mouth, trying to figure out how to articulate this, but -- in predictable fashion -- Olivia cut me off.
"Okay, rules for the last round...everything is on the table," she grinned. "Since I think we both know Rick tends to...finish...unexpectedly...we alternate every fifteen seconds. That ought to make it interesting."
Fuck...every fifteen seconds? That meant if I wanted to pick, I'd probably need to get close to the edge, hold back through someone else's teasing, and then try to finish when I wanted to...or I'd be headed out to dinner on the wrong date.
Claire nodded her agreement with the rules, seeming to shake off some of her disappointment. "Let's also say that if Rick somehow manages to make one of us cum...that person wins the date, even if he hasn't cum yet...and that person gets to finish him off." She smirked at me. "Oh, yeah, and Olivia, he hasn't used the 40 seconds you gave him...fair's fair."
Olivia giggled, perhaps sensing that Claire was trying to get back into the spirit of things. She gently leaned over and squeezed Claire against her. "Ooh, you're right. Wonder what he'll have me do. Maybe he'll make me jack him off and spray a load all over your tits..." as she spoke, she reached out and gently squeezed one of Claire's breasts, making her moan.
Claire shivered, and then made eye contact with me. "Yes, or maybe he wants to bend you over and fuck you like a good girl..." she reached around and slapped Olivia on the ass, hard, making her gasp. "Although, I've heard he cums pretty quick when he does that..." she giggled.
Fuck. I was starting to get hard again, staring, openmouthed. They both looked down at my cock, obviously noticing.
"I think Rick's ready to go..." Olivia purred. "Fifteen seconds at a time, there's going to be a lot of back and forth..."
Claire nodded. "I-I was thinking..." her face was a little pink.
Olivia was being uncharacteristically gentle. "What's up?" She said the words softly.
Claire leaned up and whispered in her ear. Olivia broke into a grin. "Yeah, I'm game for starting that way."
Simultaneously -- Olivia assured, Claire a bit more hesitantly -- they both stepped forward and kneeled in front of me.
Fuck.
Claire bit her lip, looking up at my now-hard cock with a bit of awe. "He's so big...m-maybe you want to go first..."
Olivia smirked. "Yeah, I'll go first...mmm, Rick, how long did you last the last time I gave you a blowjob?" She looked up at me through heavy-lidded eyes and licked her lips.
I recalled it vividly, and swallowed hard. "N...not long..." I admitted.
Olivia ran her hands over my length, and I let out a moan. "I guess we'll see if your stamina has improved at all since that appointment."
Without another word, she opened her mouth and started bobbing on my cock.
True to her word, she clearly wanted to win. She was moving her mouth up and down aggressively, dark eyes staring up at me. As she took as much of my length as she could in her mouth, she wrapped both hands around my length, working them up and down along my shaft with her mouth as well.
"Oh, fuck, Olivia..." I moaned the words out. I had planned to cum when I wanted, but all thinking, all plans, went out the window. Her hands and mouth felt incredible, working in unison. I was racing towards an orgasm. To my credit, I think I had lasted three pumps when she had tried this, weeks ago. She was bobbing up and down quickly, and I had easily passed that point -- maybe the many appointments had paid off, maybe it was that I had cum twice already -- but wasn't going to last indefinitely.
Claire was looking up at me, glancing between Olivia and my face, clearly impressed. "Damn, she really knows how to work a big cock, huh Rick..." she made eye contact with me. "Are you actually gonna be able to decide who to cum for? Maybe you'll just have to blow your load when it becomes too much...when you can't help it...maybe you aren't in control after all, even though you've cum twice already..."
The way Claire was talking was only contributing to the rising orgasm. As I watched, looking down at Olivia bobbing on my cock, I saw Claire move her hands -- one between her thighs, and one to squeeze one of her tits.
I was going to cum. Already. I felt ashamed, but helpless. It was just too hot.
"Time, Olivia..." Claire said, eyeing me as she squeezed one of her breasts. Fuck.
Olivia pulled herself off my length, giving me a wry smile and obviously needing to catch her breath. "Mmm, you are lasting longer. I'm a little impressed."
Then she turned to Claire, reached out, and tweaked one of her nipples. Claire let out a gasp that was half-moan. "Claire, that was more than fifteen seconds...you were letting me get him really close so you could finish him, weren't you?" Olivia giggled, and Claire blushed. "Clever, but turnabout is fair play. That's the new rule, then. Each of us gets at least fifteen seconds, and we have to keep going until the other person says to stop." She moved a little to one side.
Claire positioned herself directly between my thighs, looking up at my cock -- which was hard and glistening. She let out what was almost a whimper. "I-it's so big...I don't know if I can even get my mouth around it..."
Her voice was desperate. My cock lurched as she leaned forward and gave the tip a tentative kiss, her soft lips against the head, and then with a muffled Mmpph, forced her mouth around the head, and wrapped a petite hand around the shaft.
She bobbed up and down a few times -- far less practiced than Olivia, she got a lot less of the length, and her eyes watered a bit. The enthusiasm was there, though. She pulled off for air, moaning, and pumped me with both hands a few times.
"Fuck, you're just so big, Rick...it's so thick that it's hard to get it all in my mouth...god, and the length..." She was aggressively pumping me with both hands, staring down at my cock. I could feel myself headed towards the edge of an orgasm again. There was something in the way she talked, the helpless look in her eyes, that was a huge turn-on.
"I want you to cum all over my tits..." she moaned the words out, moving her gaze from my cock up to meet my eyes, and adjusted so she was stroking my length right in front of her chest.
"Fuck, Claire..." Again, whatever my plans had been, I couldn't think of them in this moment. Staring down at her -- my cock framed against her big tits, both hands struggling to wrap around my thick length, pumping with abandon, as she looked up at me, eyes full of need -- I felt myself about to crest over the edge.
"Time, Claire," Olivia said, a grin in her voice.
Claire pulled away, a pout on her face.
Olivia considered me, a speculative look on her face. "Interesting, that you haven't cum yet," she observed.
"I-interesting?" I spluttered the word out.
"Yeah, interesting." Claire chimed in.
Olivia continued. "I mean, you had a chance to cum for either of us there if you wanted. You didn't. Are you...playing with us, Rick?" Her tone was a bit dangerous. My cock twitched.
"N-no, you keep trading off right when I'm about to cum!" I protested.
She stood up. "He's warmed up, Claire. It's time to up the ante." She turned around, straddling me, her round ass just above my thick cock.
She leaned back, her back against my chest, and twisted to whisper in my ear. "Remember that time you watched me ride that dildo?"
"Y-yes..." I couldn't look anywhere besides toned back, her ponytail of dark hair streaming down it, and her round ass, about to sink into my lap.
"That's how I'm going to ride you, big guy." Without another word, she lowered herself, biting her lip and letting out a hiss as she adjusted to my length sliding inside her. Fuck.
Her movements were smooth, fluid. I reached down, squeezing her ass, feeling it as she bounced on me. She felt incredible...and she was picking up the pace.
This was not going to take fifteen seconds. So many of my fantasies over the last weeks -- months, even -- had revolved around Olivia, riding my cock, making me cum as quickly as she could.
And now it was happening.
"Is it what you were hoping for, Rick? I love taking this big cock..." she moaned, spearing herself on me, again and again. Fuck. I slapped her ass, and she moaned again. It had only been a few seconds, and I was already almost there.
I made eye contact with Claire. I could tell she could see what was about to happen. There was a sad look in her eye.
"She's gonna make you cum, huh?" It was Claire; she was standing off to one side. Seeing that look -- aroused, but with a little sadness, and the stab of guilt that accompanied it -- was enough to slow down the orgasm that was about to crest over me, just a little.
But Olivia was bouncing more rapidly now, making little gasps, and I felt myself quickly speed back towards the edge, about to explode --
Claire blinked once and smiled. "Time, Olivia."
Olivia let out a disappointed hmph, but pulled herself off me. Claire was clearly pleased I had managed to hold on, and smiled at me. "Sorry...I wondered if a little guilt-trip might help you last..." she said.
I paused, realizing that this wasn't going how I wanted at all; my ability to make a decision went out the window the moment one of them started working me over. They were both doing their best to win. I realized -- for the first time in literally months -- it felt important to choose when and how I came.
Claire was stepping up to me, about to do who knows what. Olivia was watching closely. I knew I was just going to be right back in a haze of arousal where I didn't have any control over the outcome, and they'd hand me back and forth between them until I exploded for one or the other. Maybe it'd be right now, all over Claire's tits; maybe Olivia would find a way to distract me and then milk my cock with her hands. But one way or another, it wouldn't really be my choice.
I did the only thing I could think of, and held up a hand. "I want to use those forty seconds where I get to tell Olivia what to do, now."
They both blinked, surprised.
