The Masseuse (Ch. 4-7: Escalations) (Patreon)

CHAPTER 4

I was nervously looking at my phone all night after my session with Olivia, but it wasn't until late that evening that my phone finally pinged.

Olivia: Okay, here's your first message to send. Settle in, in case she replies -- I'll be ready to respond quickly.

I waited with bated breath, staring at my phone.

Olivia: I know it's not going to work between us, so this isn't some desperate play to get back together. But I actually do have a question for you, Emma.

I winced. God only knew what was coming next. But...well, she was right, I knew it wasn't going to work. This felt harmless enough. I copied the message and pushed send.

Emma replied a couple of minutes later.

Emma: Okay...what's the question?

Emma was never verbose, but this was...terse, even for her. I sent the message to Olivia, who responded almost immediately.

Olivia: Straight to the point, isn't she? Okay, next message.

Olivia: When did you know it was over between us?

I paused, reading it. Actually, now that the question was in front of me, I was kind of curious about that myself. I copied the message and passed it along again.

Emma took longer to reply, this time.

Emma: I just got more and more frustrated over the last couple of months, Rick. But the last straw was last month. The night we went dancing at Muse? I know you apologized, and I thought I could get over it but...I think that was kind of when I realized I was done trying to make it work.

I blushed, thinking of that night. It made sense. I hesitated, but sent Emma's reply to Olivia. She responded immediately.

Olivia: Oooh. What happened at Muse?

There was no way I was telling her that. I texted Olivia: Filling in missing context for you was not part of the deal.

Olivia: Mmm, it must be SUCH a good story if you don't want to talk about it. But fair enough. I'll have to think of another way to persuade you to tell me. ;)

And then, as I was still flushing over that message:

Olivia: Okay, reply:

Olivia: Thanks for telling me. I appreciate you being honest. Can I ask another question? I know my, uh...performance would have had to be better for it to work out between us. How long would I needed to last for you to have been...satisfied in that department?

I stared at this one for a while. Emma and I had basically never talked about our sex life, and certainly never this directly. Maybe that was part of the problem, I thought glumly. Still, the question was one I would have liked to have the answer to, and I knew that things really were over with Emma. Eventually, I mentally shrugged, copied it over and pushed send.

Again, Emma replied more slowly, but eventually, my phone pinged.

Emma: I'll answer if you answer me a question, Rick; for most of our relationship I wondered about this but didn't want to embarrass you by asking. Have you been this quick for everybody or just for me?

I blushed. I didn't really like this turn of events...and I really didn't want to send this text to Olivia. I sat for a while, considering. My phone pinged again.

Olivia: C'mon, I know she's probably replied by now, and you're probably embarrassed to send it to me. Just send it along. I won our bet, and I'm playing pretty nice. Here, proof of my good intentions...

Along with the text, she sent a selfie -- her, lying on a bed on her stomach. She was wearing...well, it was hard to say, because the light was dim, and the camera was pointed to capture part of her face, over her shoulder. You could see a hint of her mouth, one eye, past a ponytail, to tanned and toned back -- which looked bare...maybe no top on? And framed in the center of the shot, I had a great view of her round ass in booty shorts.

Damn.

The lady knows how to take a selfie.

I sighed, now both anxious and turned on. But she was right — I had lost and she wasn’t doing anything weird. I sent her Emma's reply.

Olivia: Ooh. Tell you what -- Since I’m feeling so nice right now, I'll let you answer this one if you want, as long as you tell me what you're saying so I know how to continue the conversation. So what's it gonna be -- do you cum quick for everybody, Rick? Or was Emma a special girl? ;)

I considered, but sent the reply -- first to Emma, and then to Olivia -- without too much agonizing. Keep it brief, and no reason to lie. To be honest, Emma, I've always been pretty quick.

Olivia: Aw. So honest!

Emma took a moment longer to reply.

Emma: Thanks. I wondered if it was me. To answer your question -- I needed you to last a lot longer. Like thirty minutes. It was...really frustrating. You were big and that was exciting at first, but it was always over so fast. Hands and mouth are great, but sometimes I need...you know, a penis. For a lot more than thirty seconds.

I flushed. And then, clearly feeling bad, she followed up.

Emma: Sorry. Not trying to be mean. You're a great guy, and we had a lot of good times. But the honest truth is that sometimes I just needed to get fucked, Rick. And while I was with you, I just...never did, really.

A great guy...Well, this was humiliating. And I was also a little turned on -- reserved, demure Emma had never told me "sometimes I just need to get fucked" in the two years I was with her. Did I send these to Olivia?

Fuck it, I thought. I sent them along.

Olivia replied...and sent another photo. I admit, I looked at the photo first -- her, on her back, making a pouting face up at her phone camera. It was clear she was, indeed, topless -- I could see the tanned expanse of her collarbone and upper chest, as well as the tops of her breasts. It was hot. Then I read her reply.

Olivia: Aww, such a nice guy, and she even liked your size...but I don't think you were ever going to last thirty minutes for her, do you, Rick? You don't last through our half-hour massage sessions, the idea that you could fuck someone for that long feels pretty unlikely. I guess it wasn't meant to be.

It was embarrassing to admit, but I agreed. Emma had wanted thirty minutes? There was no way. My phone pinged again. I realized I was starting to get hard -- the combination of Olivia's photos, Emma's frankness, and talking about Emma's frankness with Olivia...well.

I pulled up the next message.

Olivia: Okay, I've got a question for you before the next one, big guy. I'm feeling generous. It's been four messages, even though I very generously let you write one of them. I get six more. If you want to fuck her again, I'm pretty sure I could make that happen, knowing what you've told me about her. I am an excellent wing-woman, trust me. Of course, I can't make you fuck her for thirty minutes -- that's on you to figure out. ;)

I flushed. I had no idea how Olivia thought she could get Emma to fuck me, but I believed her.

It felt...wrong, though. I didn't have to think for long before I replied. No thanks. Just keep going, let's get this over with. I was glad that Emma was at least replying quickly, so I wasn't going to have this lost bet hanging over my head the whole week.

Olivia replied almost immediately.

Olivia: I knew you'd say that. You're just such a nice guy, you know? Okay, next message then:

Olivia: Hey, I asked. Thanks for answering. I appreciate that you're just being straight with me. I know I could last longer...I'm working on that. Anything else in the bedroom that I could work on?

I sighed and sent it to Emma. There was an immediate ping -- but it was another message from Olivia, and a photo.

Olivia: Really hoping she talks some more about your technique in the bedroom, big guy...

The photo this time was a shot down her body, starting just below her tits. In the dim light, you could see her flat stomach, the flare of her hips into her booty shorts, and long, athletic thighs emerging from the shorts. It was fucking hot. I started to reply to her...and then pulled the photo up again, as I realized something.

Next to her thigh, on the bed, there was a big, pink dildo.

Fuck, that was hot. Was she planning on getting off on this?

...Was I going to get off to this? Fuck, it was embarrassing, but those photos...I was thinking about jerking off, when my phone pinged again.

Emma: How honest do you want me to be, Rick? I don't want to hurt you.

Oh, god...I flushed. I was rock hard, and I could imagine how Olivia was going to have a field day with this. Swallowing hard, I sent Emma's reply to Olivia...who responded quickly.

Olivia: Fuck, this is gonna be good. Next message below. Hope you're as excited as I am. 

Olivia: Be brutally honest, Emma. Really. It won't hurt my feelings; I already know I wasn't what you needed. Just be direct and specific, that's what will help me the most.

As I was reading, another photo from Olivia came through. She was sitting back, knees and ass on the ground, next to a mirror with her back to it, twisting to take a photo of her reflection. Her butt in the skimpy shorts looked unbelievable; I remembered how it had felt in my hands. She was still topless, but with her back to the shot, so just a hint of the curve of one of her breasts was visible. She was sticking her tongue out.

The big dildo was resting against one of her legs. It was impossible not to mentally compare its size to my cock. Pretty similar, I thought.

Fuck it. I was so turned on. It felt humiliating to admit, but I had to rub one out. It was embarrassing that I was doing this while Olivia orchestrated a conversation with my ex about my sexual shortcomings, but it's not like Olivia or Emma ever had to know I was jerking off...

I sent the text Olivia had composed over to Emma, grabbed the lube, and started pumping my cock, flipping back through the photos of Olivia. God damn, she had an amazing body...

My phone pinged again. I pulled up a very long text.

Emma: I mean, your stamina was the main thing, Rick. When we first started hooking up, I thought that you finishing so quick was probably just nerves. But you were fast all the time; you never lasted past like, a minute. I guess...the other thing is that I wanted you to really pin me down and go to town, you know? Some aggression and dominance. But I could tell you were struggling from the moment you were inside me, every time. You would always just kind of freeze up, and then thirty seconds later it was over. It was so frustrating.

I flushed. Ouch.

I didn't have to send this to Olivia, I told myself. I sat for a minute or two, mulling it over. My phone pinged.

Olivia: Okay, either she turned in for the night, or you're getting cold feet about the terms of our bet. And nobody turns in for the night after you invite them to be brutally honest. Our next session is going to be a lot less fun if you back out of this, Rick.

My phone pinged again. A photo: only Olivia's face. She was making a pouting expression.

Well, fuck. Pumping my cock with one hand, I sent the reply to Olivia, who replied almost immediately.

Olivia: Not exactly a five-star review, huh? Mmm, but I want more details. Next message -- this is number 7 out of 10, if I'm not mistaken, so you're in the home stretch.

Olivia: Well, I appreciate you being honest, Emma. Can I get your honest opinion on one more thing? It'd help me out. I know I'm fast, but a lot of women can't orgasm from penetration. And most guys probably can't last half an hour. I get that I'm not what you needed, but I don't have THAT big a problem, right?

I flushed. I was really hard, and slowly stroking, but...these were no longer questions I was sure I wanted answers to. And then a photo came through.

It was similar to the shot from before. Olivia's back was to the mirror, twisting to take a photo of her reflection. Her ass looked unbelievable, and now she just had a thong on. She was still topless.

The pink dildo was nowhere to be seen...until I realized I could see it, peeking out from underneath her. She was riding it, the thong pulled to one side around it. I couldn't see much because of the angle, and the swell of her ass, but...she was definitely getting off to this.

My cock surged. My phone pinged again.

Olivia: I'll keep going...if you will. Unless you're...finished early? ;)

Fuck it. I sent the message she had drafted to Emma, and kept stroking myself, staring at Olivia's latest photo.

Emma's reply came after only a minute or two. Another long one.

Emma: Rick, I don't want to be cruel, but...normally I actually cum really easily from penetration. It doesn't take much. I have multiple orgasms. But I couldn't get off without a least a little thrusting, and with how you were always right on the edge, struggling, I just...could never finish. At first I figured it wouldn't be a big deal, that you could, y'know, get better with time...but two years is a long time to go without getting off that way, Rick. And I compared notes with some of my girlfriends and they kind of agreed that their guys can all at least last like, a couple minutes. So...yeah, I think it's a problem you should work on.

Fuck...Compared notes with her girlfriends? I didn't want to send that to Olivia. But I knew if I did...there might be a photo involved...fuck...I was aroused, and embarrassed. What the fuck was I going to do?

The answer felt pretty obvious. Finish masturbating. If ever there was a situation that called for post-nut clarity, it was this one. It certainly wouldn't take long, I thought, somewhat sardonically.

Just as I decided that and started to pump faster, my phone rang. It was a video call -- from Olivia.

Well, after the photos she had been sending, I really wanted to answer that video call. My cock was making the decisions at this point. I took a few deep breaths, and tried to make sure I was holding the phone up to only show my face, before answering the call.

"H-hey...." I tried to sound casual, but I doubted I pulled it off.

"Hi...so...did she stop responding, or are you having...performance anxiety?" Olivia was laying back on her bed, phone held above her. Only her face was in frame. She sounded slightly breathless.

"Uh, she..." I didn't know what to say. My face was red. My cock was hard. Fuck.

"I'll tell you what, Rick....why don't you read her response to me out loud." Her mouth quirked, amused. "I know she has to have sent you something if that's how you're answering. If you do...I'll put on a little show for you."

"W...what kind of show?" My heart was pounding.

"Well, I've been really enjoying our little texts back and forth...did you like the photos?" She smirked as I nodded, mutely. "I could show you how much I've been enjoying it, but you have to keep texting with her. I've still got a few more messages left from our bet."

My mouth was dry. "O-okay..."

Her grin broadened. "I thought you might like that. Why don't you pull her text up and read it to me. Oh, and Rick, one more ground rule..." her expression turned knowing. "I bet you've been jerking off, haven't you? If you cum, I'm going to end the call."

"N-no, I..." weakly, I tried to protest.

Olivia just laughed. "Sure, so why don't you show me a full body view?" She smirked at my blush. "That's what I thought. Now, what'd she say?"

I flipped away to my text messages, reading Emma's message aloud to Olivia. "Rick, I don't want to be cruel, but...normally I actually cum really easily from penetration. It doesn't take much. I have multiple orgasms. But I couldn't get off without a least a little thrusting, and with how you were always right on the edge, struggling, I just...could never finish. At first I figured it wouldn't be a big deal, that you could, y'know, get better with time...but two years is a long time to go without getting off that way, Rick. And I compared notes with some of my girlfriends and they kind of agreed that their guys can all at least last like, a couple minutes. So...yeah, I think it's a problem you should work on."

Having to read the words to Olivia was a lot more humiliating than just seeing the responses. Beet red, when I finished, I flipped back to the video call, to a slightly different view.

Olivia had put the camera on her bedside table or something. I now had an excellent view of her from behind, riding a pink dildo, her ass bouncing aggressively on it, as she looked back at the camera. "Oooh, fuck, Rick. It sounds like you really were a quick cummer for Emma, huh? She could get off easily normally, but...not with you..."

Fuck. I took in the view, her ass bouncing up and down on the big dildo, and started pumping my cock again. Olivia just kept talking.

"I figured this was how she felt...mmm, and she's talked with her girlfriends about it too. Girls always talk. What do you think she's told them? How she could cum with other guys, but not with you?" She was clearly enjoying my humiliation -- her words were punctuated by moans.

"I--I don't know, Olivia--" I was overwhelmed, couldn't think. The sight of her fucking the dildo was intoxicating, and the simultaneous humiliation of the conversation I was having with Emma -- was more than I could handle. I could barely form words...but I could pump my cock as I watched her pump the thick dildo in and out of her pussy.

"Mmmm," she moaned, and took a steadying breath. "Well, let's see...Text her this: Okay, thanks for being honest with me. Hey, what have you told your friends? And how'd they react? Just want to make sure I'm clear on what other people know in case I run into them." She kept rocking up and down on the length of the dildo as she talked.

"O-okay..." watching her, as I was pumping, there was no way for me to say no. Awkwardly, with my other hand, I sent the text.

"While we wait...Rick, how long do you think you'd last if you were this dildo?" she looked over her shoulder at the phone, a mocking smile on her face. "With my ass bouncing up and down on your cock? It was one thing to do it with the toy the other day, but..." she spanked her ass, and moaned "...this would be different."

Fuck. I could feel my orgasm building as I pumped my cock.

"I mean, you lasted, what was it...three pumps in that toy?" she smirked, picking up the pace on the dildo, and moaned again. "Do you think you'd be able to get one pump inside me without cumming? Or would it be like with Emma -- just holding still, desperately trying not to cum?"

"I--I could..."

"Could you?" She giggled. "It kind of seems like you might cum before she even gets a chance to reply..."

She wasn't far from the truth, but fortunately, my phone pinged. Fortunately? It was probably going to be embarrassing. Jesus.

"And ooh, good timing. If you read, I'll keep riding..." Olivia moaned, and continued to bounce on the dildo, moving faster now.

I pulled up the text, pumping my cock and, trying not to think about it too much, read it quickly so I could flip back to the video call.

"Emma: Well...they were confused when we broke up, and kept asking why, so I just told them everything. What happened at Muse; how you have a premature ejaculation problem and how I wasn't getting off the way I needed. To be honest, nobody had ever been with someone who came as fast as you; people had a couple of one night stands that couldn't last very long, but they were all pretty astonished that I had stayed with you for two years, only getting fucked for 30 seconds at a time..."

As I finished, Olivia moaned. "Aw, Rick...it sounds like all her friends know you're a quick cummer now...how embarrassing...and fuck, I really have to know what happened at Muse..." She was bouncing relentlessly on the dildo. Watching her toned ass shimmy on it, I felt my cock twitch in my hand.

"I almost feel bad for you, "she continued. "I'll tell you what..." There was a teasing note in Olivia's voice, now. "I know you've been jerking off. If you can hold back until I'm ready to finish, cumming with you might be pretty hot."

I was speechless. Just the idea of Olivia cumming was almost enough to make me cum.

She continued to moan and bounce, looking over her shoulder at the camera, making eye contact. "Show me that big dick."

Somewhat unsteadily, I moved the phone so my hand pumping my throbbing cock was in view.

"Mmm, fuck..." she moaned, and started bouncing faster. "Imagine if I was bouncing on that thick shaft instead of this dildo....mm....you look a little bigger than my toy, what do you think?"

"I ---" I was trying to hold back my orgasm, to make sure I could cum with her. I slowed my pumping down.

She made a pouty expression. "No, c'mon Rick. You can't slow down. You have to pump your cock the way I'm riding. Match your strokes to my movement." She slowed her pace down a little, but still much faster than I had been pumping, so I'd be able to match it easier. I sped up. It was incredibly hot, and all too easy to imagine her bouncing on my cock instead of on her dildo. I moaned.

"Mmm, that's it...I'm so tight and wet...your big dick would feel so good..." she moaned.

"Olivia...I--I can't last for very long doing this," I admitted, shakily. Even without the view and her sounds, this pace would have made me cum quickly. With the sight of her moaning as she bounced on a dildo, I could feel myself speeding towards a colossal orgasm.

"Of course you can't...you cum so quickly...come on, try to keep going...I'm starting to get close, and like I said..." she pouted. "If you cum, I'm gonna end the call...and finish myself off after."

"I-I'm trying..." the words came out desperately. "Y-you're just so hot...fuck...."

"Am I?" She smirked, moaning, continuing to ride the dildo, glancing at the camera to watch me pumping my cock. "Fuck, you look like you're gonna cum any second now...is it the sounds I'm making?"

"Yeah...you look so good, and the way you sound..." I whimpered. I furiously tried to stave off the orgasm I could now feel building.

"I can't help it..." her words were punctuated by gasps now. "It's just such a big toy, Rick...it feels like I'm riding a big, thick cock..."

I felt myself approaching the edge. I tried to slow down a little bit, but her words, and the sight of her, rhythmically fucking that dildo...

"A big, thick cock...just like yours...." she bit her lip. "This is how...I'd fuck your cock...if you could last...more than...two pumps...in me..." Between the words, she was bouncing and moaning. Her face was flushed.

Moaning, I exploded. I just couldn't hold it back any more.

She watched as I came, my cock throbbing and pulsing as I sprayed a huge load. "Mmm, and that's that, huh? Aww...what a shame..." She had a knowing smirk on her face and she slowed her bouncing down, doing some grinding instead. "Can't say I'm surprised, big guy. We'll work on it in our next session."

I was panting, dazed. "Olivia, c'mon, I--" I really wanted to see her cum.

"Sorry, Rick, I told you the rules. You don't get to watch me cum if you can't last to see it happen. Now, I'm gonna go take care of this. Why don't you figure out what to say to Emma? You can handle the rest of the conversation..." She smirked, reaching towards the phone, and the call ended.

Fuck. I sat there, feeling frustrated, and a bit ashamed, as the bliss of my orgasm faded. I composed a thanks for being so honest, have a nice life text to Emma.

A couple of minutes later, my phone pinged twice.

Olivia: That was fun. Sorry you missed the grand finale...we definitely need to keep working on your stamina next session. See you next week; remember to show up early for the PT session with Claire. xo

The second ping was a photo of a pink dildo, slick and shining, on some very wet bedsheets.

---

CHAPTER 5

Another Friday, another massage appointment...although this one had PT beforehand. As I got in the car to drive over to the massage parlor, my phone pinged...with a text from Olivia.

The last texts I had gotten from her had included some spicy photos. I felt a rush, and pulled it up quickly. I was not sure how the appointment I was driving to was going to go, but I had a familiar surge of embarrassment and arousal.

I stared at the message on the screen.

Olivia: You think Claire's pretty hot, right?

Claire was, in fact, pretty hot. The receptionist was petite, with blonde hair and bright blue eyes. Young, bubbly and enthusiastic, which was appealing. She seemed a bit naive and ditzy, but even that was attractive in its own way. I hadn't really seen much of her body -- she was always wearing jeans and a t-shirt behind the check-in desk -- but she seemed fit...

I considered how much I wanted Olivia to know about what I thought of Claire. Would she be...jealous? It's not like Olivia and I were in a relationship...would she tease me? I decided I would tell Olivia I thought Claire was pretty -- that felt true enough, and safe.

But as I was mulling it over, I saw the dots indicating that she was typing another message. I waited for her message before I replied. It came through shortly.

Olivia: You don't have to answer. I know you do. Think you could last longer with her than you do with me? She might be easier to handle...

I ran my hand through my hair. I was on my way to a PT appointment with Claire -- I didn't need to be thinking about how long I'd last with her in bed. That petite little body...but she was young, she couldn't be that experienced...maybe I could handle her...teach her a thing or two...My phone pinged again.

Olivia: Maybe as long as you used to last with Emma? I liked reading her perspective on your...performance. ;)

I blushed, thinking back to last week. One more text came through.

Olivia: Anyway, guess we can talk about it in person. See you soon! xo

It was obviously no coincidence she was sending me this right before my appointment with Claire...

I put the car in drive, and realized I was anxious, and now hard, too. Fuck. How did she always do this?

When I arrived, both Claire and Olivia were at the front desk, giggling together in a way that made me immediately nervous. But Claire saw me, and brightened up, smiling at me.

"Oh hey, Rick! Thanks for coming early. It means a lot that you'd let me practice on you."

Next to her, Olivia grinned. "Yeah, Rick. It's really nice of you to come so early." She smirked at me.

I flushed at Olivia's comment, but tried to focus on Claire. She was dressed differently -- instead of her usual casual attire, she was wearing leggings, and a low-cut sporty crop-top. It showed off both a tight midriff, and a surprising amount of cleavage...she was clearly well-endowed up top, for having such a tiny frame. "Uh, sure, no problem Claire. Happy to help."

"Okay, you can head back to the first room on your left. I'll be back in a second -- Natasha's going to cover the front desk for me." She walked down the hall to what must've been Natasha's office, knocking on the door. "Hey, Natasha?"

I stared at Olivia, who was still grinning, but Claire was back in only a moment, before either of us could say anything. "Okay, we can head on back. Natasha will be out in a second. This way!"

Claire cheerily started walking towards one of their rooms. I followed her.

Olivia trailed behind us, after a moment saying, 'Hey, Claire, mind if I sit in?"

Claire glanced back, all guileless smiles and positive enthusiasm. "Sure, no problem. Maybe you'll have pointers from your massage training, or maybe you'll learn something!"

I bit my tongue. I wasn't sure I really wanted Olivia there for this...Did I? But it didn't matter; it wasn't like I could say Uh, sorry, I might ejaculate if Olivia's in the room, I'd prefer if she didn't join us. 

I was resigned. She probably wouldn't do too much with Claire there...

We entered one of their massage rooms, but Claire had clearly set it up in advance -- the table was pushed to one side, and there was a bosu ball, some bands, a lacrosse ball, foam rollers, and a few other PT and exercise implements.

I looked around and blinked. "Wow...you are prepared."

Claire nodded. "Well, yeah. I mean, this is my first try at this sort of thing, I want to do it right. Now, let's see..."

She stepped up to me. She was a lot shorter, and was forced to look up at my shoulder. I looked down, and bit my lip -- I had a great view of a truly excellent pair of tits, a deep valley of cleavage. I looked away. "Raise your arm to your side, so it's parallel to the floor...okay, now rotate your wrist so your thumb is pointing towards the ceiling. Good. Now make a fist for me with that hand..."

Over the next few minutes, Claire ran me through a series of range of motion and strength tests. She gently probed my shoulder with her fingers, had me push my arm against her hand, and so on. I was kind of impressed -- she was being very thorough.

And then, while she was working, Olivia started talking. "You know, Claire...I was thinking. Maybe a man's opinion on your...situation...might be helpful."

Claire flushed a bit, and glanced over at Olivia. "Oh, I don't know, Olivia..."

"Aw, c'mon." Olivia smiled at her. "Rick's a good guy, and he might have some advice or a different perspective on it that could help you out."

Claire was clearly embarrassed. "I...I guess..."

I was torn between being curious and slightly terrified. I didn't know what game Olivia was playing, but I had a guess that Claire wasn't the only one who would be embarrassed by it. "H-hey, I mean, I'm happy to weigh in, but if it's something private or whatever, it's all good, I don't need to --"

But Claire was looking thoughtful and nodding. "No, she's right, I could actually use some advice, and I don't really know anyone I can talk to about this. And you're a bit older, maybe you'll have an idea. Also, jeez -- your mobility in this shoulder is like, terrible. No wonder you can't handle a full massage. Here's what I want you to do..."

She got me set up doing some kind of banded shoulder rotation. It felt a little uncomfortable, but I could feel the way the motion was similar to swinging a tennis racket. She really seemed to know what she was doing. While she set up, she started talking.

"So, uh, I started dating this guy a month or so ago. He, um, he's really nice...I like him a lot..." she blushed a deep crimson.

"That, uh, sounds great, Claire. I'm really happy for you." I tried for a positive, supportive tone.

"Yeah, it's nice to have someone to hang out with. The issue is that when we, uh, try to do...stuff..." she trailed off, still bright red.

I could guess where this was going, and could see why Olivia had wanted to 'sit in.' I glanced over at her. She had an amused expression on her face.

"Yes?" I tried to say the word as neutrally as possible.

"Well, he, uh...doesn't...last very long," she finished lamely. "I-it's kind of frustrating." She broke off, inspected my form. "You're not really doing those right. Look, put your hand here..." she took my hand, and put it on her collarbone, "...and feel how the muscle's engaging when I do it. I stared as I felt the muscles in her shoulder and chest flex. Her skin was warm, soft and smooth, and my hand now was really close to one her full breasts, pushed up by her crop top. I could feel myself getting aroused, and I was wearing athletic shorts -- it wouldn't take much for Claire to be able to see it. Fuck...

"Oh, uh, thanks. Yeah, that makes sense." I pulled my hand away, and tried again, trying to do them the way Claire had. "So...um, you're hoping for advice to help him last longer?"

Claire blushed. "I...I guess? Or like, are there things I could do...or avoid doing...I don't know. I just feel kind of bad. He always seems so embarrassed. I think he can tell I want him to last longer, and he wants to, but he doesn't seem to be able to..." she trailed off.

"I see...hmm..." I tried to focus and come up with some honest advice I could give her. Claire was so earnest.

A thought occurred to me. "Did, uh, Olivia have any good advice?" I glanced over at her.

She was clearly enjoying herself immensely. "Oh, not really to solve the problem, no. I had some suggestions for what she could do to have some fun with it, but in my experience, once a guy's a..." she lowered her voice, conspiratorially, "quick cummer for you, he always will be. Dudes just kind of get in their own heads. If they can't handle you the first few times, they'll never be able to handle you."

Claire giggled and looked down when Olivia said quick cummer -- it was obvious the dirty language was a bit thrilling for her.

But Olivia was making eye contact with me the entire time she was talking. When she finished, she ran her tongue over her lips. Fuck. Now I was absolutely starting to get hard in my athletic shorts. I worried again that Claire would notice.

"But I thought, hey, an older, experienced guy like you might have some ideas, Rick." Olivia smiled. It was an absolutely predatory smile.

"I, uh...right..." I didn't just want to agree with Olivia in front of Claire, but....it was true that for both her and Emma, I hadn't ever handled either of them, not really. I had always cum quickly. Fuck...maybe she was right. But Claire's earnest, hopeful face demanded a better answer than that. I wracked my brain.

"Well, hmm...I don't wanna pry, Claire, but is there like...something specific, that sets him off, that you could maybe...avoid?" My mouth was dry, trying to keep my tone...light. Just some friendly, casual advice, about how not to make your friend blow his load too fast, y'know?

Claire blushed and stammered..."Y-yeah, it uh, it's..."

Olivia smiled, and filled in, surprisingly gently, "her, uh, friend is having trouble any time her...breasts...are involved, Rick."

Oh. It was impossible not to glance down and consider the many ways those big tits could have made me cum. I could feel that I was getting harder as the conversation continued. I had to get ahold of myself. I swallowed, hard.

"I...I see...maybe uh...maybe you could...try different positions..." I said, lamely.

Claire considered. "Actually, now that I'm thinking about it, we have mostly done stuff that, um, features them prominently," she said. "That's a good idea. And, speaking of different positions, I want you to try something else. You're not engaging your core. Like, at all. We're going to try some bird-dogs. Do you know how to do those?"

I shook my head. Bird-dogs?

"Okay, I'll demonstrate. You get down on all fours like this..." Claire got on her hands and knees, and looked up at me. Well, she looked up...but she wasn't making eye contact. She bit her lip and blushed.

Fuck, fuck... She was obviously staring at my crotch. I wasn't totally rock hard, but I was hard enough that the outline of my thick length was clearly visible. I quickly got down next to her. She blinked a few times and resumed talking, obviously trying to pretend nothing had happened. "And you raise an arm parallel to the floor, and a leg as well. At the same time. Use your core for stability." She demonstrated. I tried to focus on following along. "Good. Do those for 90 seconds." She stood back up.

Olivia giggled. "90 seconds, huh -- a timeframe you're familiar with, Claire?"

Claire giggled as well. "To be honest, uh...90 seconds would be an improvement. He really, um...he really likes these." As I glanced up, she grabbed her full tits and gave them a demonstrative squeeze for Olivia, laughing. I stared briefly, and then tried to look back down at the ground before Claire noticed me checking her out...but I wasn't fast enough to avoid Olivia glancing at me with a smirk on her face. Fuck, how does she engineer these situations?

"So, Rick..." Olivia mused, "different positions, huh? Is that something that helps you last longer?" I could her a little teasing in her tone.

"Y-yeah..." I muttered. A lie -- but what was I gonna say? Well, Olivia, as you know, I can't really hold my load no matter what position I'm in?

"Oh, that's so interesting," Olivia's tone indicated purely academic curiosity. "Is there a position you find, uh, finishes you off most quickly?"

"With the girl on top," I muttered, blushing as I thought about my last massage appointment with her, and not looking up.

Claire chimed in. "Huh. Well, maybe I'll try some different positions out. Um, Rick, any advice for, uh..." she blushed, and started stammering to get the words out. "So, he, uh, really likes it when I, uh, y'know, use my...breasts...on...his…on him." She stopped for a moment, then continued, "but...but that, um, is over pretty quick, and even though I'm ready, to, y'know...do it, after...he's out of commission." She paused, trying to decide if she had been clear enough. “And he wants me to do that for him pretty often, so it means, uh…” she trailed off, clearly too embarrassed to continue, and also worried she’d been too vague to be understood.

Olivia smiled wickedly and provided a vulgar translation. "You're saying he likes it when you titfuck him, but he cums quick and then you guys can't have sex after?"

Claire blushed at her frankness, giggling and looking down again, but nodded. "It's uh....it's not the first guy this has happened with, either..."

Olivia laughed. "Well, that does sound like a problem. Any words of wisdom, Rick?"

"I, uh, hmmm..." I stammered. I was too busy thinking about what it would be like to have Claire's big tits wrapped around my cock. I could see why guys wanted her to do it, and i could see why they would have trouble handling it.

But Claire interrupted. "Hey, you're not doing the bird-dogs! You were supposed to go the full 90 seconds!" I blushed, and I could see Olivia open her mouth to make what was undoubtedly going to be a joke about my stamina, but Claire continued too quickly. "Your core must really suck. Do some sit-ups. 50 of them, take as long as you need. I'll hold your feet." Sighing, I rolled over, getting into position and Claire put her hands on my feet, leaning forward.

I realized that I had a problem. A few problems, really.

First, my cock was rock hard from the conversation we had been having. Thanks, Olivia.

Second, Claire was leaning forward to pin down my feet, the deep valley of her cleavage on full display. Her tits were almost perfectly pale, just a few freckles, and in this position it was all too easy to imagine how soft they were, how it would feel to have her lean over, putting my cock between them...

Third, and perhaps most importantly, I suddenly realized Claire, from this angle, could easily see up my athletic shorts. I was wearing underwear, of course -- I wasn't an idiot. In fact, I had opted for compression underwear. That helped a lot with containing everything, and I could feel it pinning my erection against one of my legs. But it also meant that, in this moment, I was pretty sure there was a clear outline of my rock-hard cock -- down to the thick ridge of the head -- that left nothing to the imagination.

"Okay, fifty of...these..." her voice trailed off. She was obviously staring down my shorts. Fuck.

I was staring at her tits, so it was impossible to miss the flush starting to creep along her neck, and the clear outline of her nipples through her crop top. She was getting turned on by looking at my dick? At that thought, my cock twitched. And her eyes widened when it twitched.

I tried to think quickly, of some way to diffuse the situation. Out of the corner of my eye, I saw Olivia taking in what was happening -- the angles, the silence involved -- and obviously calculating, assessing what she could say to escalate things.

Her lips quirked up in a smirk. "So he cums too fast for your tits, huh, Claire?"

"Y-yeah..." she said the words distractedly. I did a crunch, which put my nose practically right against the excellent tits in question, but Claire didn't really notice -- she was staring down my shorts. Fuck... This suddenly felt like a potentially dangerous situation. I wasn't going to get softer, that was for sure, and I liked Claire. I was worried she would feel offended, or harassed, or...

"Hmm. Follow-up question...how big is he?" Olivia had another wicked grin on her face, but Claire was too transfixed to notice.

"Oh, uh, I dunno...I used to think he was pretty big..." the words came out absentmindedly, her focus clearly on my cock. "But, um...I think he might...be average...or a little below average...I haven't...seen that many, you know...I'm not sure I've actually been with a guy who's like really...big...before..." She bit her lip, staring at the outline of my thick cock.

Damn. Being the object of desire was a nice change of pace. But I was starting to get worried. It was really turning me on. I was going to be leaking precum -- and that would be visible too. She didn't seem upset -- quite the opposite -- but I didn't want to cross a line with her and make her upset. How many sit-ups had she asked for? 50? I was on...twenty seven. I started trying to go faster, but it turned out she was right -- my core did suck -- and I actually needed to pause for a bit before I could continue.

Olivia, of course, continued. The woman was relentless. "Well, you know, that might be the problem." As she spoke, she moved a bit closer, so that she was behind Claire, and she lowered her voice, seductively. "If they're going to cum quickly anyway, it's a lot more fun in my experience if the guy involved is...y'know, packing. That way you at least get a bit of a show." Olivia winked at me. Fuck. This was so hot, but I needed to get out of this situation before I embarrassed myself. Thirty-five, thirty-six...I had to stop to take another breather.

"Y-yeah...that makes sense...oh..." Claire's eyes widened. I realized I was definitely leaking precum, and she could probably see a stain growing. I felt my cock twitch. Her lips parted, and she looked a little flushed. I guessed my twitching, leaky cock was putting on quite the show -- and she was enjoying it. Fuck... The wanton desire on her face was obvious. I didn't usually worry about cumming hands-free...but...Claire's big tits and clear fixation on the outline of my thick cock were enough to have me on edge.

Olivia must have known what I was thinking. She mouthed words to me over Claire's shoulder, and I glanced away from Claire's tits, reading her lips. DO. NOT. CUM...YOU. HAVE. TO. LAST. Fuck. She knew I was close...I gritted my teeth and cranked out a few more sit-ups. My core was on fire. Thirty nine, forty, forty-one... I had to get out of this situation.

Olivia kept talking. "I mean, think about it. It's probably pretty hot when he loses control for you, right? Feels good to know he can't handle your body? That kind of thing always makes me feel a certain type of way...." She glanced at me, and bit her lip.

Claire nodded, only half-listening to Olivia, her attention still singularly focused on my cock. "Y-yeah...it does..."

Olivia was leaning really close to her ear now, but was making direct eye contact with me as she kept going. "Now, imagine that good feeling, but he's...bigger...thicker...it feels different between your tits..." Claire was almost panting. So was I. And it wasn't the sit-ups.

"That...um, yeah, that would be hot..." Claire sounded like she was hypnotized. Her breathing was shallow.

"I mean, the whole experience is different," Olivia's voice was low, and seductive. "With more length, it could practically be slapping against your face while it was between your tits.."

"R-right...big..." said Claire. It was clear she was imagining one cock in particular at this point against her face...and between her tits.

So was I.

"And when he actually loses control, well..." Olivia continued, staring at me. "When they're big, you can really feel them throb. It's exciting."

"Mmm-hmm..." Claire's sound of agreement was more like a moan. And my cock throbbed as if in agreement with Olivia as well.

"The only problem..."and the smile in Olivia's voice was clear, now, "is that when they're that big, you really wanna know what they feel like...inside you. So you really want a guy who's big and lasts..." she winked at me. I wasn't sure how much more of this I could take. Forty-five, forty-six, forty-seven. My core failed again, and I had to take a breather.

"Yeah...that...that makes sense...I would want..." her words trailed off. I could imagine what she was seeing -- I had to be leaking enough precum that the head of my cock was probably clearly visible through the compression material. The way she was obsessing over my cock was so hot. I was now worried I actually would cum if Olivia kept going with this.

"What would you want, Claire?" Olivia's voice was soft. "I mean, I'm a bit of a size queen, so I'll just say it -- I like a nice, thick length inside me."

Claire breathed out through parted lips. "Y-yeah...that...yeah..."

Olivia grinned at me, but continued, softly, "And one that can last. Not one that's only good for two pumps."

Claire nodded, mutely, and let out a slow exhalation, staring at my cock.

Olivia kept talking, her voice almost like a purr. "You want a big one that can really, y'know, pound you into the mattress for an hour or so. It's an amazing feeling."

"Yeah...big...fuck..." Claire practically moaned the words. She was flushed, lips parted, breathing fast -- and she was staring at my cock, which I thought was probably going to tear the compression shorts, I was so hard. I could tell she was fantasizing about me fucking her into the mattress for an hour.

I was right on the verge of cumming. I had to end this. Forty eight, forty nine, fifty. I lay back, breathing hard. "All done. Damn, you were right Claire, I do need to do more core work." I tried to say the words casually, to bring both of us back.

"Oh, you um...looked good to me..." Claire blinked. She seemed a bit dazed. "Yeah. Good work. I, uh, I think our time's up, and I need to use the bathroom before I, um, go back to the front desk. Don't worry about the PT stuff, I'll get it later when I clock out. Thanks, um, thanks for letting me practice, you know...just thanks." Her face was bright red, and she made her escape as quickly as she could.

Olivia giggled, looking at me. She walked over and closed the door behind Claire. "You know, there's like, a full ten minutes left in your PT session before our appointment starts." She walked back over to where I was laying on the floor, and sat down facing me.

"That...that was kind of intense for Claire, I think, Olivia..." I was still incredibly turned on, and trying to get control of myself, I pushed myself up into a sitting position, arms on my knees.

"Oh, it was intense for Claire, huh?" She smirked. "I mean, you're not wrong. I think she went to the bathroom because she needed some alone time, Rick. I wonder what she's thinking about?" she blinked her eyes innocently.

"Olivia, c'mon, I --" I was so turned on, I really didn't want to continue this line of conversation.

"You know..." she tapped her chin, as if she was considering. "I think I might know." She leaned toward me, conspiratorially, whispering in my ear.

"I think she's thinking about you, Rick. I told you I was a good wing-woman. She's thinking about that big dick you've got. She's thinking about what it would be like to have your big cock between her tits, how it would be so much bigger than the guy she's seeing now. Maybe big enough that she could suck on the head of your cock while she was fucking you with her tits. Maybe there'd be enough shaft poking out to stroke you while she did it. She's thinking about how much thicker you'd feel in her petite little hands. I bet she was wondering if she could even get her mouth around the head of your dick."

Olivia bit my earlobe, and then her mouth moved lower, along my neck. I moaned. Just hearing her lay all this out was so hot. I could tell I was on the edge, and evidently...so could she.

"I could tell you were getting close, and I said you have to last, Rick," she whispered, a smirk on her face. "We're working on your stamina, remember? Don't cum yet. That's for our session, in a little bit...if you're good..."

"I'm trying..." the words tumbled out of me, desperate and needy, and she giggled.

"Mmm, that's the issue, isn't it? Because Claire was also thinking about what it would be like to have you on top of her...sliding that thick cock in and out of her. That's what she's thinking about right now, I bet. She's got her hand down here...she's touching herself thinking about you fucking her silly. She's thinking about how hard she'd cum on a thick cock like yours, pounding in and out of her. Frankly, she seems...kind of obsessed. You really owe me one."

As she spoke, Olivia slid her hands into her leggings, and moaned, mimicking Claire. "Oh, Rick..." Was she...actually turned on? I couldn't really tell if she was teasing me or really feeling it. She kept eye contact with me. Either way, it was incredibly hot. This wasn't the reprieve I needed.

"Mmm...but...now that I think about it...she wasn't actually thinking about your dick, was she, Rick?" She smirked.

"Wh...what?" I was confused. Claire had been staring right at it and practically drooling. I had been embarrassed that I let things escalate that far, but...there was no question in my mind, she was thinking about my dick.

"I'll explain, but first...let me just make sure I understand what Claire was seeing..." Olivia pivoted so that she was sitting in front of me, and pushed me back so that I was in a sit-up position again.

I was rock hard, and throbbing. Her eyes sparkled as she looked down at the view Claire had had of me doing sit-ups. "Mmm, she did have a great view. You're leaking, Rick." Her hand in her leggings moved. I was sure she was masturbating, staring at my cock. Fuck. My dick twitched. She giggled. "Oooh, and she could definitely see when it moves. Nice."

"Do y-you like it?" I tried to say it with confidence, but it came out more like a schoolboy asking a teacher for approval.

"Oh yeah, Rick. I think I've mentioned, I do like a nice...thick...cock...and watching the effect it had on Claire was...really...hot..." With each word, she sounded more and more turned on. "Pull it out and stroke it for me, Rick," she panted.

I didn't need to be told twice. With some difficulty, I pulled both my compression briefs and the athletic shorts down my legs. I mean, Olivia had seen my dick before. I was already slick with precum. I started to pump it, staring at her.

"Anyway..." the word was punctuated by little gasps, and she stared at my cock. I was really having trouble stroking slowly -- she was even hotter when she was turned on, and I was right next to her. My eyes roved over her athletic body -- the shape of her legs in her leggings, her ass against the ground, moving slightly as she fingered herself, her tight waist, the hint of cleavage visible in her top -- before resting on her face, as she kept talking.

"Like I was saying...she isn't really thinking about you." She moaned as I pumped a hand up and down my length.

"She's thinking about a big dick that could last. You couldn't fuck her like that. We both know that. I saw how you were looking at her tits. You'd probably cum even faster than the guy she was telling us about."

Now I moaned, thinking about Claire's tits. In spite of myself, I was pumping faster. Olivia noticed -- her grin grew wider. "It sounds like she really knows how to give a titjob, too -- that guy isn't the only one who has cum quick for her. I don't think you'd stand a chance."

Then, she moaned. "Can you imagine if she were kneeling in front of you, her big tits around that thick cock?" Her voice shifted, mimicking Claire's tone, breathless and bubbly. "Oh my gosh, Rick, your dick is the biggest I've ever seen. It feels so good between my tits. Oh...I can't even get my hand all the way around it. I...I can't wait to feel it inside me."

I slowed my strokes down. I could feel the edge approaching, but I wanted to prove a point for once. "I...I could last for her..."

Olivia smirked. "Oh, yeah?" She continued imitating Claire. "Rick, you're getting precum everywhere...your dick is leaking so much; it's getting all over my tits...and it's so big..." Olivia moaned again, making circular motions with her hand down her pants.

I stopped stroking, trying to control myself. I didn't have to cum if I didn't want to, I thought. But in my mind’s eye, I could see it -- Claire's tits wrapped around my thick cock, me thrusting into them, her hopeful, wanton expression, desperately wanting me to last so I could fuck her...

Olivia's smile was knowing, now, and this time her impression of Claire was still bubbly, but wanton with desire. "Rick...I know you're getting close...but you're so much bigger than the other guys I've dated...I need to know what you'd feel like inside me..."

Oh, fuck. I moaned. Her impression of Claire really captured the earnest need I imagined Claire would have, seeing how she'd been drooling over my dick. Even not stroking, I felt myself approaching the point of no return. It was just too easy to imagine how easily I'd blow my load for Claire's tits while she pleaded for me to last.

"...so don't cum yet...just hold back a little...I want you to fuck me..." Olivia said, staring at my cock. She sounded breathless, the way Claire might be, if she were looking down at my twitching cock between her big tits. But I was gone. And Olivia knew I was gone. She continued, a disappointed pout creeping into her impression of Claire, "C'mon Rick...you can last...you're so experienced...you're not gonna blow your load quick like those other guys, are you?..." She bit her lip in mock concern.

"Oh god, I --" and with that, I couldn't hold back anymore, and exploded, most of it getting on the floor of the room...but in my head, it was all over Claire's tits and face.

"Mmm...whoops, sorry," Olivia purred. "You weren't even stroking anymore, so I guess that must've been my fault. You know, I think she'd be simultaneously disappointed and kind of impressed by that performance, Rick." She stood up, wiping herself off with a nearby towel, which she then tossed to me. "But, yeah...it doesn't seem like you could handle her tits...I wonder how fast you'd cum if she actually titfucked you? Thirty seconds?" She giggled.

Fuck...I was dazed. Maybe she was right, but this had been so...hot.

She was at the door. "Well, I've gotta get the room ready for our session...see you in a few minutes," she smirked, and left.

---

CHAPTER 6

A few minutes later, I was in with Olivia, with the usual setup I'd have for a massage: naked, under a towel, face-down.

But she wasn't wasting any time.

"Mmm, that was pretty hot with Claire..." She was massaging my back, but her voice was in my ear.

"Yeah? Did...did you like it?" Face-down, I couldn't see the expression on her face. I had a brief moment of wondering if she was jealous about how much Claire's tits clearly turned me on.

"Well..." her voice had a teasing smirk, "I would've liked it more if I had gotten you to blow your load in front of her, or maybe made her have an orgasm in front of you...but yeah, it was fun."

I blushed. "W-why are you..." I wasn't sure how I was going to finish the sentence. Why are you teasing me? Why are you like this? Why are you so good at this?

Olivia didn't let me finish, though. "But you know, there's probably something more important we should talk about." Her voice had a sober undertone to it.

I knew what was coming. The text conversations with my ex-girlfriend Emma. The video call Olivia and I had while I was texting. It had all been pretty intense, and Olivia had gotten a real window into my relationship with Emma; playing with that had felt...well, pretty intimate. I wasn't sure what Olivia and I were doing, but...yeah, we should definitely talk. The thought was worrying. What if she didn't want to do these sessions anymore? Didn't I want her to stop teasing me about my premature ejaculation problem? Then why was the thought worrying? I felt like an emotional basketcase.

"Olivia, I--" I wasn't even sure how to start the conversation.

"I've gotta hear about what happened at Muse, Rick." Now I could hear the grin in her voice, even as she dug those talented fingers into the muscles of my upper back and forced a moan out of me. "It sounds like a really hot story."

Jesus Christ. She was toying with me, again. "O-oh..." I had forgotten that, in the course of texting with my girlfriend, Emma had mentioned an incident about a month ago at a club we had gone to. A pretty embarrassing incident, as far as I was concerned. "I-I'm not sure..."

"Mmm. I know you're not sure." Her voice purred. "That's why I want to hear about it so badly. I bet it's embarrassing." I flushed red. Why did she like humiliating me so much?

"So let's make a deal. I want to hear the story. The long version, no details left out. I get to ask follow-up questions. What...do...you...want...big guy?" As she spoke, her hands went lower on my body, tracing along my ass, over the backs of my thighs, and in towards my balls. I shivered and let out an involuntary whimper.

What did I want? A good question. I wanted to fuck her. I wanted to see her cum. I wanted a blowjob from her -- a real one, not one where she teased me so hard beforehand that I came in ten seconds in her mouth. Any of those would be satisfying. I considered. How to structure this so I actually got what I wanted for a change?

I wasn't sure, but there was one thing I wanted most of all. "I...I want to fuck you," I said. “From behind. I want to bend you over and fuck you.” Fuck it. She was so hot. I needed to be inside her. Just thinking about it was getting me hard. And I had just cum, during the "physical therapy" session with Claire -- maybe I could actually last longer than usual.

"Oh, I know you do, Rick..." The mocking tone in her voice was direct, matter-of-fact. "Are you sure, though? You know it'll be...embarrassing. You'd cum right away. You might not even get inside me."

"I-if you want to hear the story, those are the terms." I ignored her teasing, and tried to say it with a calm confidence...but there was a pleading note in my voice.

"Well...I don't know, Rick, all you have to do is tell a story...and in return I have to bend over, and take that big, thick cock you've got inside my pussy? Pump it in and out of me? I mean, if you don't cum before you get inside me, obviously..." Her hands traced circles on my body. "Is that really a fair deal?"

Her words sent a surge through my cock. "It, uh..." I flushed. "It's the kind of story you'll like, Olivia."

She smirked. "Mmm, you can be a real tease, Rick, you know that? Hmm..."

I waited. It really was the kind of story I suspected she'd like. I didn't really want to relive the embarrassment of that night, but if I got to fuck her...

"Okay, but I get to tease you while you tell it, and if I can make you cum before you're done, you still have to finish the story...but we're not having sex." She had a twinkle in her eye.

I flushed. "You...you know there's no way I'll be able to handle you teasing me." I gritted the words out, ashamed to have to say it out loud. But we both knew it was true.

"Aw, Rick...we've been working on your stamina...have some self-confidence..." she pouted for a moment.

"But you're probably right. You just don't seem to be able to handle me...what if we made it easier for you? While you're telling the story, I can't use my hands...or my mouth...besides talking, I mean," she said, smirking. "That really limits my options. And obviously, no penetration until you're done with the story...and bending me over, to put that big dick in me..." she let out a mock moan, looking over her shoulder as if she were looking back at me fucking her from behind. Fuck.

No hands, and no mouth...I thought about it. That felt like it took away the ways she'd made me cum so far...I just had to hold on while I told the story and she teased me. She was definitely good at turning me on just by talking, but...it would only take a couple of minutes... "Okay, it's a deal."

She let out a little squeal of delight; it was embarrassing how good it made me feel. "Great. Why don't you flip over onto your stomach, lie there, and I'm gonna pull up a chair -- no hands or mouth but I at least want to look you in the eye while you're telling it." She grinned, and pulled a chair over. I turned, laying on my side to look at her. "Okay, ready when you are." She sat, elbows on knees, staring squarely at me expectantly.

"So, this was a Friday night about a month ago. It was supposed to be a date night between me and Emma, but her friend, Brittany, had just gone through a break-up..." I broke off as she moved. "...I'm sorry, are you...raising your hand? Like to ask a question?"

"I'm trying to be very respectful and demure. You know, to help avoid any...accidents." She batted her eyes innocently, lowering her hand. "Please describe Emma and Brittany. I mean, I know Emma but...who's Brittany?" She grinned. "And if the story is gonna feature the two of them, tell me what they both look like. Are they hot?"

"Oh, um, okay..." I thought about them. "Well, like you've heard, Emma is nice. Quiet, demure. About my height, dark brown hair, um....I always thought she was hot..." This was weird, describing my ex to my...masseuse? I didn't know what Olivia was, but masseuse didn't seem to cover it, I thought.

Olivia leaned in. "Not nearly enough details. What are her best physical attributes, in your opinion?"

I flushed, "um....I really liked her mouth....um, kissable lips, you know? And, uh, she has a nice butt."

"Oh, I see. 'Kissable' lips, huh? That feels like some coded language...did she give good head? I bet she did, huh. And a nice butt...you guys ever do anal?" Olivia grinned at my discomfort, and waved a hand. "Aw, I know, not part of the story...yet, anyway. Please go on. And Brittany?"

"Brittany, uh..." Brittany was something else. "Well, Emma always called Brittany her hot friend. She's short; pretty, oval face; green eyes, long dark hair; incredible body. I think she was a personal trainer or something. A lot of time in the gym, and it showed. My buddies always wanted to know if she was single after they met her. Anyway, she's really hot. And outgoing -- talkative, confident, kind of a tease --"

"Mmm, okay. I think I get the picture. Your girlfriend Emma, and her hot, recently-broken-up-with-friend Brittany, who's a bit of a tease...I like this already. Please continue." Olivia leaned forward further, engaged, and I got a nice glimpse of the hint of tanned cleavage she always seemed to be sporting.

I continued. "Right. Okay, so Emma and I were going to have a date night, but Brittany had just broken up with that guy because he had cheated on her. Emma felt bad and asked if we could go out with her instead. I didn't really want to... I figured this was basically a girls night thing. It was probably going to mostly be the two of them getting increasingly drunk, maybe Brittany crying...or making out with some guy and THEN crying. Someone was eventually going to vomit in the ladies' room, and I'd get to be the bored, sober chaperone just trying to make sure they both got home safe without puking in my car.""

She smirked, "And? Is that how it went?"

I rolled my eyes. "Would I be telling you this story if it was? Well, Emma hinted that if I played my cards right maybe we could try something adventurous in a club or bar bathroom. She was almost never up for that sort of thing, and so I figured, sure. Anyway, this way I figured they wouldn't do anything too stupid."

I thought back. "We started off at a bar, sitting at a table drinking and listening to Brittany complain about her ex for a while. She's going off about everything wrong with him -- he can't drive, he called himself an "entrepreneur" but he had some failing apparel business and could barely pay his rent, the whole works. Finally she says something like and Emma, the worst of it is that his dick was just tiny. Like, vienna sausage tiny. The saving grace of this breakup is that now I get to fuck something that's bigger than my index finger."

"Oooh." Olivia leaned forward. "What'd Emma say? Did she tell Brittany what a big, quick-cumming dick you've got?"

"Well, I couldn't hear, but she kind of drunkenly giggled, and then leaned over to whisper in Brittany's ear. It must've been something about my size, because Brittany gave me...well, I think Brittany had kind of always dismissed me out of hand, but she gave me a different kind of look. Like, a respectful, impressed one, almost."

Olivia smiled. "Mmm...how about Emma, talking up her boyfriend's big dick but not mentioning that he can't last in bed. She is nice."

"Uh, yeah, it made me feel pretty good. I was kind of surprised -- Emma didn't like to talk about that stuff with anyone. Including me. She must've been getting drunk. Anyway, Brittany kept complaining, but as she was talking, Emma reached over and..."

Olivia glanced down at the towel that was covering my groin. "Ooh. Did big Rick get a hand job under the table?"

I flushed. "N...not a handjob, but she was definitely like, fondling me...feeling me up...I think Brittany always made her a bit jealous -- pretty, outgoing, guys chasing after her -- and so knowing that her ex was small and I was big made Emma feel good. Anyway, I think Brittany noticed. She was kind of watching Emma and I, and now her comments about how shitty her ex was were interspersed with comments about how lucky Emma was to have a guy like me."

Olivia giggled. "Rick, if this story ends with you having a threesome, I'm gonna call bullshit."

I sighed. "No...I said it was a story you'd like."

She pondered. "Actually...I guess if you told me you and Emma brought Brittany into the bedroom and you blew your load in five seconds because of how hot she was, I'd believe that...and like it..." she smirked.

I rolled my eyes again. "You know what, I'm just going to keep telling the story. Anyway, Brittany eventually gets tired of complaining about her ex and gets really animated about the three of us going out dancing so she can meet a guy like Rick, she said. That's how we ended up at Muse..."

Olivia laughed. "Brittany seems great. But I'm getting kind of bored, Rick...when does it get good?" She stood up and started stripping off her leggings and t-shirt. She was wearing a sports bra, and a little black thong. Her tanned, sculpted ass and long legs flexed as she stepped back over to me, and sat down again in the chair she had pulled up next to me. I stared. Her tits were inches from my face.

I was instantly hard. Fuck, she looked good in the dim light of the massage room.

Olivia grinned. "If I get too bored, I might not let you to finish the story...and then you won't get to fuck me." She pouted. "So why don't you get to the good stuff?"

"R-right...sure..." I tried not to get distracted by the expanse of tanned skin next to me, and kept talking. "So anyway, we get inside, we go to the bar and get some shots. Emma and I hang out a bit and dance; Brittany alternates between dancing with random guys and dancing with us. They do a few more shots. An hour or two of this goes by. The three of us are just kind of dancing, and then Emma leans over to me and -- she had to shout to be heard, mind you -- kind of drunkenly slurs into my ear that she has a fun idea about something we could do together, and to meet her by the bathrooms in a minute. She heads off."

"Oooh, our hero, about to get laid," Olivia giggled.

"Yeah, I mean, that's what I thought too. I felt a little bad about the idea of leaving Brittany alone, but I figure I can probably take her drink with me so nobody roofies her, and uh..." I flushed. "I mean, I didn't expect it to take...long, in the bathroom. A quickie, like you said."

Olivia smirked, but said nothing. I paused a moment, then continued.

"That's not what happened though. The second Emma was gone, Brittany turned and started dancing with me. At first, it was fine, and I figured, no big deal -- but after a minute it wasn't just dancing, she was absolutely just grinding her ass on my crotch. And like I said, Brittany barely gave me the time of day before, so I was surprised."

"Mmm...." in one fluid motion, Olivia climbed atop the massage table next to me, and pulled the towel away, lying next to me so I was spooning her, with her ass against my groin. "Like this?" she started grinding against me.

"Uh..." I moaned, "Olivia..." My cock had been hard, and now it was raging. She had an incredible ass, and I could feel my thick length between her cheeks. Her hair was in my face, her back against my chest...Fuck.

"What?" She asked innocently, "is this not how she was doing it? Did her ass feel better than mine?" She pouted.

I ignored her final question. "No...it...it was pretty much like this...just more clothes on..." Fuck, her ass against my hard cock felt good.

"Keep talking..." I could hear the grin in her voice. "You wanted to fuck me from behind, right? This is just a nice warmup."

Right. If I didn't finish the story, I wouldn't get to fuck her... I tried to ignore the sensation of her full ass, pushing rythmically into my groin, my thick cock nestling between her asscheeks, and continued. "Uh, well, she did that for a bit. I was...pretty turned on, honestly, like I said, she was hot, and then she started talking, saying..."

I bit my lip, remembering the feeling -- her ass moving in time to the beat, feeling my cock getting hard, and then Brittany's voice. "Mm, Rick, Emma wasn't kidding...you're a big guy..."

"Oh my god, Rick. Did you cum in your pants with her grinding her ass on you?" She gasped in mock-horror, but started grinding against me even more aggressively.

"N-no" I said, defensively. "Before I could even respond, she--she turned around, and kind of straddled me...so she was kind of straddling me, grinding herself against my cock..."

Olivia flipped around and climbed atop me, being careful not to touch me with her hands. Following the rules. My thick shaft was rubbing against her thong. I could feel the heat of her, and...I realized her thong was wet. Before I had started getting precum on it. Fuck. She was turned on.

As I realized that, she started sliding up and down the length of my shaft. I wasn't inside her, but it was impossible not to feel her pussy -- wet heat radiating off it, the sensation of her lips sliding along my length -- as she worked up and down my erection.

Fuck. I moaned. A few inches and a slightly different angle, and I'd be fucking her. The thought was consuming me.

"Like this?" Olivia asked, grinding up and down my length. "You...you seem distracted, Rick..." There was a teasing note in her voice. "Are you going to be able to finish the story?"

I tried to focus. "Y-yeah, kind of like this...except we were standing...a-anyway, I could tell it was turning her on...like she could probably feel me...how hard and big I was..."

"Mmm," Olivia moaned. "Big dick like yours, yeah, I bet she could. Did she say anything?"

"Yeah, uh, she-- she giggled, and uh, --" I moaned. I was trying to focus on telling the story --- I wasn't on the edge quite yet, but it was hard to make progress. Her thong kept getting wetter, which was making the grinding feel better and better. And...there had been rules about Olivia touching me, but none about...me touching her...I looked up at her, dark eyes staring down at me, tits barely contained by the sports bra that I could reach up to fondle...and a knowing smirk forming on her mouth.

I knew if I started touching her, there was no way I was going to finish the story. I put my hands by my sides and tried to get it together. "So she giggled...and said something like I can't believe Emma was keeping such a big secret from me."

"Oooh," Olivia's exclamation was almost a moan as she slid up and down my length. "Brittany, not above going after Emma's man...what did you do?"

"I --" I moaned. This was quickly getting to be too much. I knew if I let Olivia keep going, and if she started teasing me, she'd have me cumming in no time. I tried to focus on finishing the story. "I, uh, I asked her to stop, but she just laughed and said Mmm, you feel really turned on, Emma must not be satisfying you the way you need..."

But Olivia interrupted again. "Mmm, and you thought Brittany was really hot too, right? Did you ask her to stop because you were with Emma...or because you were getting close to cumming? Like you are now? With a hot girl grinding on you?" She smiled knowingly.

"I...yeah, I guess I was getting close...but I really didn't want to cheat..." I bit my lip, trying to fight off the sensations. I couldn't believe how quickly this had me on edge.

"Mmm, what a good guy. So..." Olivia leaned down over me, still grinding, but whispering in my ear now. "What happened next, big guy?"

"Well, Brittany didn't want to stop...she kept going for a bit...I tried to pull away but she was really holding on, and I knew she was drunk, I didn't want to push her over or anything and, um...it was feeling really good..." The embarrassment of the memory was palpable, and warred with the arousal I was feeling.

"Did she make you cum, Rick?" Olivia asked it with a smile in her voice.

"N-no..." I fought to hold on. I was almost at the end of the story, and focused, trying to finish it. "She---she could tell I was getting close though. I don't know how -- maybe something on my face, maybe precum leaking through my pants...anyway, she was watching my face, grinding, and then backed off, and giggled. She kind of drunkenly slurred out mmm, don't get too excited, big guy...I don't wanna make a big dick like yours cum all over the dance floor...what would Emma think? And she went and started dancing on someone else. It was just a tease for her, I think; she wanted to get a rise out of me to make herself feel good. To be honest, she was so drunk I don't even think she remembers the evening at all. I was glad she stopped -- if she had kept going I...I would've cum in my pants, like you were saying."

I flushed, breathing hard, feeling humiliated to admit it...and even more humiliating that I was close to blowing my load right now, even though Olivia wasn't using her hands or mouth at all.

I stopped talking, hoping she'd take it as the story being over. Olivia looked thoughtful, and slowed her grinding down...but then a knowing expression came over her, and she picked it back up again. "Oh, that's not the end of the story, though. You went to the bathroom to find Emma after, didn't you?"

Fuck. I definitely couldn't take much more of this...but she was right, of course, there was more to the story. "Y-yeah" I gritted out, moaning. "I, uh, found her, and she dragged me into a stall and locked the door behind us. She--" Olivia had picked up the pace of her sliding up and down my cock now, and as I watched, she pulled her thong aside -- I could feel her hot, bare, wet pussy rubbing up and down my thick shaft. I froze. Don't cum, don't cum, don't cum... I tried to hold back the orgasm I could feel building.

She giggled. "Aw, Rick, are you gonna freeze up and cum, or are you gonna try to finish the story and maybe get to fuck me? I'm so wet from your thick cock...it'd be a shame if I had to take care of this by myself, again..."

Fuck... I tried to continue "...she-she could tell I was really turned on...she knew I hadn't been that hard when she had left...she looked up at me, got down on her knees, and started unbuttoning my pants...while she was doing that, she said..." I moaned.

The closeness of Olivia's body, her wet pussy against my shaft was too much. I could feel that in another moment or two, I wasn't going to be able to stop myself from cumming. I tried to keep talking, rushing, trying to get the story out there before I came.

"She...well, Emma was really turned on, I could tell. She just started talking, and Emma never talked dirty like this. She asked me if I was this turned on because of Brittany. She said she could tell Brittany was horny for my big dick, that she'd seen Brittany checking me out all night, and she had known Brittany would try to make a move the second she walked away. That it was hot that Brittany wanted me, but that my big dick was all hers, all Emma's. That she was so good at making me cum, and she was gonna remind me why I was with her. It was so fucking hot, my quiet, demure girlfriend just drunkenly saying all this stuff. Then she said she was gonna wrap her lips around my thick cock and..."

It was too much. Olivia had picked up the pace, and was moaning in my ear -- carefully not touching me with her mouth. And remembering that night, Emma horny and on her knees in front of me, unexpectedly made it even hotter. I couldn't hold on any more. Moaning, I started cumming, bucking my hips as my cock pulsed ropes of cum all over Olivia's abdomen -- and mine, too.

But Olivia picked up where I had left off, having heard enough to guess where things were heading. "...and give you the best blowjob of your life..." she let out a little gasp as she felt me start cumming, but didn't stop sliding herself up and down my shaft.

And then she giggled. "...but I bet that was enough to make you cum, wasn't it, big guy? Did she even finish getting your pants off? Get her hands around your cock? Or did you just explode while she was zipping down your fly?"

"Sh-she...stroked me...once or twice..." I was still orgasming, my dick pulsing, moaning the words out as she slid up and down my thick shaft. It felt amazing -- but I also felt the familiar sense of embarrassment as I realized I wasn't going to get to fuck Olivia. Fuck, she made me cum early, again...

Olivia was delighted. "Awww...so she didn't even get to give you the best blowjob of your life as promised? And you're not gonna get to fuck me either...sorry, big guy." She slid up and down my length a few more times, before climbing off, and grabbing a towel to clean herself up.

"I know how much you were looking forward to...what was it...bending me over?" She gave me a cheeky grin, turning around and leaning away from me so I could see her round ass. "Spanking my ass while you fucked me?" She gave it a little slap. "Maybe I'll think about that a little later on, when I take care of myself, since you weren't...you know, up to the task."

Fuck. My cock twitched, and at the same time, I flushed, humiliated. She started dressing. I lay there a bit longer, panting, before beginning to clean up and do the same.

She had an amused expression on her face. "So one last detail I'm interested in from the story...was Emma pissed?"

I was bright red, and I answered without making eye contact. "I mean, yeah. I came all over her face and top before she could even put her mouth around me. I tried to play it off -- like her dirty talk was so hot that I just couldn't help myself -- but to be honest I think she thought it was borderline cheating that Brittany's dancing had gotten me that turned on, and she didn't even get to finish the job. It was pretty much the end of the night. We went and got Brittany and I drove us all home. A very long, silent car ride -- they both passed out. I think Brittany blacked out and didn't remember anything, but Emma sure did."

"Mmm. You were right, it's the kind of story I like. But you know, I'm not really sure your stamina is improving much," she mused, glancing at the clock as she finished putting her clothes on. "This was similar to last week! I thought PT beforehand might help, but it didn't, really. I'll have to think of some different approaches to try. Your lack of consistent progress is concerning."

"I---" I was speechless. Whose fault was that?

"Anyway, thanks for the story. Sorry you didn't get to...y'know, make it all the way through and get the prize at the end," she winked. "But there's always next time!" She walked out.

---

CHAPTER 7

Another Friday, another massage appointment.

It was weird, I thought. Behind the mix of nervousness and arousal I felt before these appointments...I felt...content?

The appointments had become part of my routine, in some strange way. I didn't know what would happen, but I knew at the end of the week I'd come here, I'd see Olivia, and we'd....well, play. It was always arousing, generally more than a little humiliating, and I wasn't sure I was getting enough actual massage to feel the benefits in terms of looser muscles and less tension -- but I did feel like it was helping me cope with the stressors of life.

So I was feeling pretty good when I walked in the front door and saw Claire sitting at the receptionist desk. I gave her a little wave.

She blushed, and looked down. Oh, right...I had forgotten the physical therapy appointment, which had gotten...hot.

I tried to think of something to say. "Uh, hey, Claire...thanks for showing me those exercises. They've really been helping. I can feel a difference already." This was, in point of fact, a lie; I hadn't been doing them at all. But I figured it was a harmless lie.

She brightened up. "Oh, good! Thanks again for letting me do a practice session with you."

I tried to keep eye contact, but it was difficult; she was wearing jeans and a tank top. The tank top really showed off her chest. I couldn't stop thinking about the things she was doing to make her unnamed guy friend cum too quickly.

Olivia strolled out of one of the rooms just then, her usual mischievous smile on her face.. "Hi, Rick. Stop flirting with Claire and let's get your appointment started."

This had what I was sure was the intended effect -- both of us got bright red. "I-I wasn't…you're terrible, Olivia. Okay, let's go."

But as we turned away, Olivia paused, as if considering. "I know, just teasing you. And actually, you know, Claire, you were kind enough to let me sit in on your PT session last week...want to sit in on Rick's massage appointment? If you're interested, I mean. You might learn some things."

Olivia glanced at me, and winked. "Assuming Rick doesn't mind, of course."

I thought about how the PT session had gone. "I don't mind if you want to, Claire." I smiled at her, trying to be enthusiastic without being, as I felt, totally creepy.

Claire bit her lip. I wondered if she was thinking about the PT appointment. "Well...let me see if Natasha will cover the front desk for me. I bet it would be interesting to see your technique, Olivia."

She had no idea.

So it was that a few minutes later, I was fully disrobed, under a towel, listening to Olivia give Claire some running commentary on how she started massages. "...So, I grab the oil like you might expect, but before I start touching the client, I start assessing for any tightness that might be visibly evident from how they're holding themselves on the massage table...like you can see Rick is holding one shoulder a little higher than another?"

Claire murmured agreement. "Hmm, I wouldn't have noticed it, but now that you've pointed it out, you're right..."

I shifted uncomfortably, and Olivia immediately said, "Hold still, Rick, I'm trying to help Claire learn something."

It went on for a few minutes like that. This was, I thought, way less fun than my usual appointments. I considered how Olivia would respond if I suggested I get a partial refund.

But as she started to massage me, I heard Olivia's tone shift. "So, Claire...how's the guy you were telling us about last week? The one with the, uh, stamina problem?"

Claire giggled, "Oh...um, I just broke it off with him, actually. Just this week. There was another, um...disappointing performance last weekend..."

Olivia made a delighted sound. "Oooh. You gotta tell me. What happened." I could feel her kneading my back harder, now, working her way lower.

Claire giggled again. "Well, he showed up on Saturday at my place, and I made dinner and we split a bottle of wine, y'know, just a nice little date. I wore this dress that always gets me lots of compliments that I figured he would like. It's, uh...pretty low cut..."

Olivia grinned. "I can imagine. Okay, so you were looking hot, you're both a little tipsy, and the girls were out. What happened next?"

Listening to Olivia talk to Claire about her sex life was definitely turning me on, and I had suspicions about where the story was going. Olivia's hands on me weren't helping -- it was like she was using extra massage oil, or something. Everything felt even more slippery than usual. I was grateful I was still face-down, because I could tell my cock was getting hard.

Claire smiled, "Well we started making out. I could tell by the way he was feeling me up that he was focused on, y'know, these -- " I couldn't see Claire gesturing at her breasts, but I could picture it "-- just like always, and so I wasn't surprised when he asked if I'd use my, uh, tits on him. And then I thought about what you were saying -- how if a guy is gonna finish quick anyway, you might as well have some fun with it..."

Olivia smirked. "Oooh, I can't wait to hear this. Rick, you can turn over now, I'll do your front. Claire, what happened next?"

Fuck...why now? I panicked a little, and tried to think about my options. Did I ask her to do some extra work on my hamstrings or something? But she glanced at me and winked. She was doing it on purpose...

Fuck it. I flipped over. I surreptitiously tried to adjust my semi-erect penis so that it wasn't quite so prominently protruding. Olivia started working oil into my traps and chest.

"Well..." now I could see Claire's face, and she was a little flushed -- perhaps embarrassed, perhaps just enjoying the story. "So, I got down on my knees, you know, and got my tits out, ready to...do the thing. And he, um, he got it out. He was like, really hard already. And I remember thinking -- he's not that big. When we first started dating, I thought he was pretty big, but lately, um...I dunno, I've been feeling like...he's more average...and when I looked at it then, all hard in front of me, it just seemed kinda...small." She bit her lip, and glanced down at the towel covering my groin. "So I decided to tease him a little."

Now it was Olivia's turn to giggle. "Oh my god, Claire. What did you say?"

I was now fully erect. Maybe seeing my dick last week had left her disappointed with this guy? The thought was admittedly kind of hot.

Claire smiled. "Well, it was right in front of my tits, and I just looked up and him and said 'Oh wow, your little guy looks really excited.'" Her tone was a little more breathy and naive than usual -- almost ditzy. "I could tell he didn't like that I called it his little guy, but his thing, like, twitched, and I could tell he wasn't gonna last long anyway, you know?"

Olivia looked impressed. "Damn. That’s a good line." Then her attention shifted. "Oh, before I forget, Claire -- I want you to feel his shoulder, here, and see what I'm doing. Take the heel of your palm, here..." Claire stepped up by my head, and now I was looking up at her as she stared down at me, following Olivia's instructions. I could see her eyes roving down my body, taking in the thick length of my cock under the towel. She bit her lip.

And then I could feel her hands on me -- smaller than Olivia's, and far less assured. She tried to follow Olivia's instructions.

Olivia inspected her motions with a professional eye. "You're doing the right movement, but not nearly hard enough. Really push into him."

Claire did -- but I was slippery with oil, more slippery than she'd expected. She lost balance as her hand slid from my chest down my abdomen. Her tits pushed into my upper chest and face as she fell into me. Her hand ended up only inches from the head of my cock.

"Ah, shit, sorry Rick..." she sounded really flustered. She was still staring at the outline of my cock as she righted herself and pulled her hand away.

"It's no problem," I assured her. "No harm done." Her tits had felt as amazing as I had imagined, full and pillowy. Fuck, no wonder that guy was cumming so quickly for her.

Olivia laughed. "It's all good, I did that a few times too when I was just starting...sorry about your tank top, though..." she touched Claire's shirt, which was covered in the oil. "It's probably ruined -- that stuff doesn't come out of clothes easily."

"Maybe I can keep it from seeping through and ruining my bra too..." Claire sighed and pulled her tank top off -- she had a sports bra on underneath that showed off even more cleavage, but was maybe just enough coverage that you could've gotten away from wearing it at a gym with no top over it. She inspected it for signs of oil. I was inspecting it too, remembering the feel of her tits against my face and chest as I stared.

"Well, it looks oil-free...can we keep going like this or should I go get a t-shirt or something?" Claire asked.

Olivia was quick to reassure. "If you don't mind, I mean, Rick's already shirtless, so it's not like you're underdressed, and that way we don't take up any more of his time slot...I mean, he doesn't usually take a full time slot--" she smirked "--but he's being awfully nice to let me show you a few things, so let's not make him wait."

Claire blushed. "R-right. Sorry, Rick..."

Olivia pressed on. "Anyway, I'll keep working on him, I just wanted you to see the shoulder technique I'm using, given his mobility issues. So, what happened with your friend's little guy? I'm dying to know." Olivia's hands resumed, working their way down my abdomen now.

Claire giggled. "Oh, right. So, like I said, I could tell he wasn't gonna last long once I got going with these, you know?" She gestured to her tits again. "So I decided I was gonna tease him a little more -- it's like you told me, you might as well have some fun with it..."

Claire bit her lip. I could tell she was trying to decide how detailed to be about the story. She glanced down at my groin, covered by the towel, and that seemed to help her make up her mind.

"So, I decided I was gonna tease him a bunch before I started. I looked up at him and batted my eyes and said 'you know, babe, last time your little guy didn't last that long...I really want to get fucked tonight, can you last for me?' Well, he was blushing, and kind of stammering about how he'd definitely last this time. So I said, 'mmm, baby, I can see you twitching, are you sure you'll be able to last? Maybe I should just, y'know, use my hands a bit first...'" She said the words sweetly, innocently, like she was just asking an honest question.

As she spoke, Olivia had reached my groin, and was teasingly under the towel with her hands, tracing circles along my thighs and brushing against my balls. I tried not to moan, focusing on Claire's story.

"Well, he seemed less certain after that, but I started pumping him with my hand, and kept talking. 'I'll warm you up...we wouldn't want your little guy to explode right away...' Well, I could tell that he might cum just from my hand if I kept going. So obviously, I did; I could tell he wasn't going to last long enough to fuck me anyway. I kind of did this, to show off, you know..."

She brought her elbows together in front of her, squeezing her breasts together through her sports bra, emphasizing her cleavage. "And then I started jerking him off faster, and said 'I bet I can make your little dick disappear between my tits, they just swallow you up, huh?' And, uh...well, I could tell he had lost it, he started kind of bucking his hips...so I said 'Aww, babe, you're small, but I figured you'd be able to last'...and I mean...that was it for him. He was done."

Olivia was staring openmouthed at her. "I...wow. You really, um, listened to my advice." She let out a small laugh.

It was almost enough to make me laugh, too...if I wasn't so fucking turned on. I was breathing hard, staring at her tits as she told the story, imagining how my cock would look between them.

Claire blushed. "It was, uh, really fun, actually. Frustrating, but like you said, once I realized he wasn't gonna last anyway, I just leaned into it..."

But she trailed off. She was staring at Olivia's hands under the towel, mere inches from my cock. "Can you...can you show me what you're doing there? Groin injuries are really common..."

"Hmm, sure...Rick, this is obviously an intimate area, but we can keep you covered...you don't mind, right?"

I stammered that I didn't mind. Olivia adjusted the towel, and started doing some technical explanations of the muscles she was targeting. They were both standing by my groin, looking down at my hard cock now, barely covered.

Claire seemed to be only half-listening to the explanations, but when Olivia asked her to try, she readily moved her hands under the towel, feeling along my upper thigh.

She glanced up at my face, making eye contact with me, and -- biting her lip -- she brushed her hand against the thick base of my shaft. She let out a sharp intake of breath as her fingers brushed along the first few inches of my length, and I let out a little moan.

The energy in the room shifted, palpably. The wanton desire in Claire's face was obvious. She was staring at me.

Olivia smirked, but just said "Mmm, careful, lots of nerve endings in that area..." and then, wiping her hand on a towel, pulled her phone out of her pocket.

She stared at it for a moment. "Shit, guys, I gotta handle this...Natasha just texted me some questions about one of her other businesses, and I need to pull some info off her computer. I'll be back in a couple minutes -- Claire, maybe you can, y'know, run him through some shoulder PT work? Sorry, Rick, maybe we can give you a discount or something, this isn't really fair to you...it seems really urgent...back in a few..."

She turned to face me as she was about to pull the door closed behind her, mouthing a few words. YOU'RE WELCOME. I WANT TO HEAR ABOUT IT.

To be honest, though, that barely registered for me. Claire hadn't stopped staring. She and I made eye contact for several more tense, silent seconds. She spoke first.

"I wanna see it." Her voice was a desperate whisper, breathless, needy. My cock surged.

"Claire, I--" I had absolutely no idea how to respond, but it didn't matter -- she was already pulling the towel away.

"Fuck...you're big..." she was staring, openmouthed. "I...wow..."

"D...do you like it? Bigger than the guy in your story?" My throat was dry, but the words came out more confidently than I expected.

"...yeah...a lot bigger..." She seemed entranced. "What do you want me to do with it?"

I was staring at her tits. She didn't wait for more of an answer than that.

"Fuck...it's just so thick," she whispered. She climbed up onto the massage table, between my legs. I felt the warmth of her body on my thighs as she moved so that her tits were positioned over my cock. She took a moment and pulled off her sports bra, revealing soft, full breasts, pale skin and nipples. She reached down, touching my chest and legs, getting oil all over her hands, and then caressing her tits, rubbing oil on them.

I couldn't stop staring. Her tits were perfect. "You look amaz--" but she wasn't wasting time, and I moaned as she wrapped her tits around my length. It felt amazing. She knew exactly what she was doing -- the pace of her breasts sliding up and down my shaft, the eye contact, the amount of oil, everything. She smiled up at me.

"Fuck, your big dick feels good. This is the biggest I've ever had, Rick. It's so thick, and I love moving up and down this long shaft..." she moaned.

"Claire...fuck..." I was panting, moaning, trying to stave off an orgasm already. Fuck, we had just started. All I could think about was her story, that she had just been mocking a guy who hadn't lasted long enough -- a guy with a smaller dick, even. I had to try to do better than that.

She could clearly tell. "You know...Olivia said you were experienced... that made me wonder if that meant you would be able to handle this...but.." I could feel the power dynamics between us shifting -- she was younger than me, but she gave an incredible titfuck, and she knew it. I tried to get myself under control.

She smiled. "You're a lot bigger than the other guys, but you're reacting just the way they all do...I bet I can make you cum pretty quick. It's kind of hot...your dick is so big, but I can still--"

"I-I can...last a while..." I tried to cut her off, to assert some degree of dominance in the conversation. But her tits, slick with massage oil, felt so fucking good, and I had thought about this happening to me, a lot, over the last week or so. I trailed off.

"Can you?" She was staring up at me, considering. “Okay...I'm just gonna...” and the smile on her face shifted to one that was a bit more vapid, a little bit ditzy and openmouthed.

Her tone shifted, too. "...Of course you can last if you want to..." she didn't say it sarcastically, though, like Olivia might have. Breathless, biting her lip, looking up at me as if she were powerless. "You're so big...you could do whatever you wanted with me...I don't even know if your big cock would fit, but if you wanted to fuck me, I couldn't stop you...you'd just take me..."

I could tell she was playing up this naive, helpless, overwhelmed act, but...it was hot, and in combination with this titjob, it was working on me. I felt my cock twitching...and so did she.

"God, look how big the head is...and those balls...I bet you cum so much..." she said it in the same way, overcome by my size, powerless as she looked down at my cock pumping in and out of the top of her cleavage. "Do you want to cum all over my big tits? Make that big dick explode all over them? You could last longer, but you don't have to..."

The mental images she was conjuring made it very hard to keep control, but I cared a lot about impressing her, and was barely holding on. Maybe the sessions with Olivia had actually improved my stamina?

And then, she adjusted her technique. Wrapping one arm around her tits to keep them tight and pumping up and down my cock, she took her free hand, and wrapped it around the several inches protruding from the top of her cleavage, and started pumping with her hand as well. The sensation was incredible -- tight around the head of my cock, and soft and pillowy against my shaft and balls. The view -- her petite hand and big tits wrapped around my cock, her lips parted, looking down at it -- was so hot.

I knew there wasn't anything I could do to keep this from making me cum.

"Oh my god, you're so big I can even jack you off while I fuck you with my tits...my hand barely fits around your thick cock..." she moaned. "Your big dick gets whatever it wants...I have to please it...I’ll do whatever you want…do you want me to keep going? Do you want to cum all over my tits, right now?" Her words were submissive, but I nodded, helplessly. "Are you sure? If you want to fuck me with that big dick instead, I guess we could try to make it fit..."

But I couldn't have responded to that, even if I had wanted to. I felt myself tip over the edge, and moaning, I started to cum. Claire kept pumping me with her hands and backed up slightly, ensuring that I mostly came all over her chest. The sight of her -- pumping my shaft, moaning, angling me so I sprayed rope after rope across her full tits -- was incredibly hot.

Fuck. I was staring at Claire's tits still as my orgasm began to recede. It had been, maybe...a minute? Maybe.

Claire shivered, as if overcome by what had just happened, and then looked up at me, blushing.

"Rick, I...wow...that was...I've never really said...done...it like that...I...you..." she seemed to come to her senses, then, and realized we were sitting in a room with an unlocked door, her top was off, and her tits were absolutely plastered with massage oil and my semen.

We both sprang into action, then, toweling off and redressing. We were just in time to preserve appearances when Olivia opened the door. "Really sorry. Rick, but I don't like to keep Natasha waiting, she gets kind of cranky..."

She glanced between us, the curiosity on her face warring with the smirk. "Thanks for finishing things up, Claire. I knew I was leaving Rick in good…hands."

Claire, blushing, didn't make eye contact. "Th-thanks Olivia. And, uh, a big thanks to you, Rick...really appreciate the...practice time..." Bright red, she scurried out.

Pitched so only I could hear her voice, Olivia whispered, "You owe me one. A big one." She winked, and then, in a more normal tone, said brightly, "Well, Rick, thanks for coming, as usual. I'll see you next week!"