The Masseuse (Ch. 1-3: Wagers) (Patreon)

Authors Note: Readers who have been following me since the early days on Reddit, or those who've gone deeply down that rabbit hole, will recognize this series. It's one of the first things I ever wrote. It's imperfect and as I re-read it, I can see a few places I'd handle things very differently with so much more experience writing under my belt...but overall, I think it holds up pretty well, and I really liked writing this story, so I'm reposting it here.

I've lightly edited it to improve things in a few places but the plot's the same. This isn't a new story, but I wanted to bring it over to Patreon eventually, and this is the definitive edition. :)

My plan for right now is to leave this whole, edited series as a paid reader exclusive. If you haven't read it, I hope you enjoy; please consider it a small thank you for supporting me. If you've already read it, perhaps this prompts you to revisit it. :) I'll probably post a little chapter bundle every few weeks until I've posted the full series.

CHAPTER 1

It had been a shit week.

It had started on Monday with my boss telling me that I was getting put on a performance improvement plan; I wasn't delivering like she needed. A low performer. Not hitting targets. She was kind when she delivered the news, but it stung anyway.

On Tuesday, I had learned that my mixed doubles tennis partner decided she was going to play with someone else in our league this season. "Nothing personal," she said...though she looked uncomfortable, like maybe it was personal. "I'm just hoping for someone who can, uh...bring some power to complement my speed, you know?" I knew she had been a lot better than me, but again, it still stung.

But the real nail in the coffin was on Thursday, when my girlfriend dumped me in a bar, right at the start of what was supposed to be our date night. Seeing the crushed look on my face, she had said, "Sorry, Rick. I just don't think we're compatible."

"What do you mean? We get along great!" I was aghast. Sure, we had our spats, but I hadn't expected this at all. "What...what's the issue?"

"Yeah, um...I...haven't really been getting what I need for a while." She glanced around, lowering her voice like she was saying something embarrassing.

"Oh. I'm sorry. Look, it's been a hard week, I can do a better job of listening..." but I trailed off as she shook her head.

"I'm not talking about the last week. And I'm not talking about my emotional needs," she whispered.

Her face was bright red. After a moment, so was mine. I knew exactly why she was dumping me.

"Emma, I--" but, message delivered, she had scurried out of the bar.

---

As a result, on Friday, as I walked up to the spa entrance, I rolled my shoulders, feeling the tension in them. I was looking forward to this. The place had great reviews online, but I had never been.

I walked in, and the receptionist greeted me, checked me in, and directed me to a room. Moments later, my masseuse walked in. A younger woman than I expected, she was pretty. Asian, maybe, with tanned skin, dark hair and eyes. She was wearing yoga pants and a tight-fitting tank top that showed off a great figure. Yeah, I was looking forward to this.

She smiled and shook my hand. "Hi, I'm Olivia. Looking forward to working with you. Since this is your first massage with us, a few questions before we start." Her tone was personable and friendly. She matter-of-factly ran me through a questionnaire -- any injuries (yes, my shoulder, from years of badly playing tennis), scent sensitivities (no), any heart conditions (no), oil or no oil (oil, please), and would I prefer a silent massage or was talking okay (talking was fine, thank you). Finally, she looked up, smiling.

"Okay, we're through the checklist, I'll get started in a moment. Go ahead and disrobe to the level of your comfort -- if that's naked, you can use that towel over yourself. When you're done, lay down on the table face down, and I'll be right back." She walked out of the room. I stared after her, watching her ass in those yoga pants as she walked out of the room. Damn. She wasn't just pretty, she was hot.

I stripped, lay down on the table face down, and tried to relax. I heard the door open behind me and Olivia return. She did something with the switches on the wall, and the lights dimmed.

"I was glad when you said you didn't mind talking. I do like to talk during massages. I've never been a fan of those stuffy formal places where some stranger is massaging you in complete silence. It just feels...impersonal. Hope that's okay; let me know if it gets annoying and I'll shut up." As she spoke, I could feel her hands -- warm, and wet with oil -- touch my upper back, probing and rubbing.

"I don't mind." Her fingers felt amazing. Her touch was strong, confident, and I could already feel her putting pressure on knots in my muscles, smoothing over them. I had to stifle a moan.

"Not to be too informal but damn, dude, you are tense. You lie on rocks for your 9-5 or something? I've seen construction workers with fewer knots in their back than you've got." She started to dig the heels of her palms into my knotted muscles more forcefully, and I felt some of the tension start to melt away.

"Ha, yeah, I can't say I'm surprised. It's been a hell of a week." I failed to stifle the moan this time.

"Oh? Tell me about it." I ran her through the whole sordid litany -- getting called in to my bosses office, dumped by my doubles partner, and then dumped again by my girlfriend. She made sympathetic noises throughout as she continued to knead my back and upper arms.

"Aw, that's a tough way to end a shit week. Why'd she dump you?" She asked the question with idle curiosity and compassion in her voice. I felt my face redden, which I was hoping wouldn't be visible to her in the low light with me face-down.

"Uh, she didn't really say...just that we weren't compatible, uh, that she wasn't getting what she needed." I tried to keep my tone nonchalant instead of embarrassed, but she was working over my legs and calves, now, and I let out a grunt at the end of the sentence as she dug in on my calf muscles.

"Oh, I see. Well, that happens sometimes. I've got a few exes I wasn't compatible with, either. I know it hurts, but good to just break it off if you aren't getting what you need, right?" Unless I was mistaken, there was now a bit of a knowing smile in her voice. "Anyway -- can you flip over? I'll do your front next."

As I started to flip myself over, like any red-blooded man getting massaged by an attractive woman, I mentally took stock of my, uh, state. Her hands on my back had left me still mostly soft, but fairly engorged. I was pretty happy with that -- soft enough that I wasn't presenting her with a raging hardon under the towel, but big enough that I had a nice masculine bulge. I hoped, anyway.

"So..." as she started on my chest, she made eye contact with me. Her eyes were pretty -- dark in the dim light -- and her lips curved into a small smile. "Not to pry...but she said she wasn't getting what she needed, huh? Were you?"

"W-what do you mean?" Again, I tried to play it cool, feigning indifference.

"Well, in my experience, when a girl says that without specifying anything, it usually means problems in the bedroom." She smirked, in a knowing kind of way. "So I'm curious if you were both dissatisfied or if it was just her." As she talked, her hands were working down my stomach, and I realized -- with a jolt of excitement, mingled with horror -- that I was getting hard. It was her fucking smirk, the way that she seemed to know...

"Oh, I don't think that it was anything like that. She always said that she was pretty happy with that, uh, side of things, and so was I." It wasn't a lie -- Emma had only ever had nice things to say. Admittedly not especially enthusiastic nice things. Kind things, if I was being honest.

"Yeah?" Olivia had been moving up my legs, was now working on my upper thighs. She was leaning over very close to me -- I could feel her dark hair brushing me, the warmth from her skin, and she had adopted a whisper, leaning close to my ear. Her tone was a bit...teasing? "You know, sometimes girls will say things are fine because they don't want to be mean..."

I was unbelievably conscious of how close her talented hands were to my now-very-hard member. "Oh, I uh....yeah, I know, but..." I stammered as her hands crept closer and closer to my cock, unable to get a coherent word out.

"So...are you sure there weren't any bedroom problems? Maybe she was just being nice to you." Her face was inches from mine, and the smirk had gone from knowing to almost mocking.

It was admittedly hard to focus with her pretty face and full lips inches from me. Glancing away, I could see down her tank top, the curving shadow of appealing tan cleavage. Her hands were working closer and closer, massaging my upper thighs and groin, tantalizingly around, but not on, my cock.

"I, uh...I really don't think so..." I sounded about as unconvincing as possible, now, even to myself.

"Rick..." she said my name teasingly, chiding. "Come on. I don't even know you, and even I can tell you don't really seem like a guy who knows how to take care of a lady. You're wound too tight." Her smirk became almost mocking.

"Wh-what's that's supposed to..." I tried to muster indignation, but I trailed off as her hands, finally, almost casually, reached my cock, gently wrapping around it under the towel.

"What's that supposed to mean? I'll tell you." She was whispering right in my ear now, her hair across my face. I could feel her tits against my chest as she leaned on me. Her hands were gently pumping my cock, and the combination of precum -- which I was leaking -- and massage oil made them slippery. "Rick, I've been massaging you for ten minutes. You're rock hard just from having a pretty girl massage you. This is supposed to be a full half hour massage but there is absolutely no way you could go that long without cumming all over the place. Of course your girlfriend left you. You've got a short fuse." Her smirk deepened. "You just don't last long enough. You're a quick cummer."

I moaned. With her hands pumping my cock, and those words in my ear, it was the only response I could give.

"So no, I don't believe there were no bedroom problems; I think she probably wasn't getting fucked the way that she needed. In fact, I'm so sure...I'll tell you what. Let's make a bet. If you can handle yourself through, let's say, two minutes of a handjob right now, I'll believe you. Hell, maybe I'll even let you take me on a date. I saw how you've been looking at me. You'd like that, wouldn't you, Rick? I'd be a great rebound. So what do you say -- two minutes of this and you can convince me you didn't get dumped because you're a two-pump chump."

In my pleasure-addled haze, I tried to consider. I was really turned on. But two minutes wasn't very long. Maybe I could last. "Okay--"

She cut me off. "Easy, cowboy. I wasn't done. But if you can't last -- you've got to buy one of our three-month platinum packages. And you have to use it. That means you're coming back here to see me once a week, for the next three months, and we're going to spend a lot of time talking about your little endurance problem while I massage you."

"I--that seems--" I was too turned on to think about anything besides her hands, relentlessly pumping up and down my cock.

She paused, pulling her hands away. "I mean, if you don't want to try, I can also just resume the usual massage." She smiled, enjoying the look of wanton need in my eyes. "I mean, a real man could do it. It's just a handjob. But if you already know you'll lose, it's not really a good bet to take. I get that." Her smile widened into another smirk.

I felt an absolutely overwhelming combination of emotions -- first and foremost, frustration that she had stopped stroking me. But alongside that, I was insanely turned on, and it had me feeling a mix of shame and embarrassment. I had no idea how she had so quickly sussed out the reason that Emma had dumped me, but Olivia's hands were so talented; I was not at all sure that I could last long enough to win this bet. And, with how things were going at work, I was not at all sure that I should be buying a massage package to see this woman on a weekly basis.

But I was thinking primarily with one thing -- and it wasn't my brain. "I can do it."

Her grin deepened, and she leaned over close enough that her lips touched my ear as she whispered. "Mmm, so confident." Her hands resumed pumping the shaft of my cock. "We'll find out." She glanced at the clock. "Two minutes -- starting now."

I tried to get my shit together, tried to focus on anything besides the physical sensations -- her hot breath in my ear, the weight of her soft tits on my chest, and the tight grip of both of her hands as they moved up and down my cock. But she was already talking again.

"What kind of date do you want to go on, if you win?" She pulled her lips away from my ear, making eye contact with me. "Dinner someplace fancy? I've got a little black dress that makes my tits look amazing; I think you'd like that..." she glanced down at her tits. "Or a hike, maybe? I bet you'd like to see me in yoga pants going up a hill in front of you. Could you keep up, though? The bedroom might not be the only place you don't have enough stamina..." She giggled, continuing to pump me.

My breathing was quickening in spite of myself. The talk of her body was just turning me on more. I shut my eyes and tried to direct my thoughts elsewhere -- I didn't need to imagine what a date with her would be like, there wouldn't be one if I couldn't pull it together -- but she just kept talking.

"I bet that's not what you really want, though. You probably just want to watch movies at your place. We could both wear pajamas, and snuggle under a blanket, and watch -- I don't know, it wouldn't even matter what we were watching." She was pumping me faster, now. "Eventually I'd distract you, and we'd be making out...and then we'd be in your bed, and you'd be sliding this cock into my tight little pussy, pumping in and out, in and out..." She moaned, in time with her hands pumping up and down my cock. "Maybe you'd bend me over and fuck me from behind...I like it when a man takes charge. You could pull my hair, spank me...I like that, Rick..." She continued moaning, and bit her lip, as if she were picturing it.

Oh, fuck. She was indeed painting an insanely hot picture. I could feel myself getting close.

"Mmm...." she slowed her strokes down. "But that's not what would happen, would it?" She stared into my eyes, the smirk on her face growing. "You wouldn't be able to last long enough to make it inside my pussy. You'd cum from fondling my tits, or from squeezing my ass, from me going down on you...or from a handjob, just like this one. You can't fuck a girl like me from behind. Or in missionary, or any other position. I'm just too much for you to handle."

I moaned, right on the edge. Her strokes were slower, and that was the only reason I hadn't cum yet, but my ego demanded I reply. "N-no, that's not true, I--"

But she glanced at the clock and cut me off, totally in control. "Forty five more seconds and we can go on that date, Rick. But we both know you're not going to make it that long. You can't handle this. That's why your girlfriend dumped you. Did you ever even get to fuck her? Or did you just cum before you could stick it in?"

She smirked, and picked her speed up again, and -- with a surge of humiliation -- I knew it was over. The sensations combined with her words were just too much. I couldn't answer her questions. I moaned again as I approached -- and sped right past -- the point of no return. Her smirk widened further; clearly she knew what was happening as well. "But, hey, we can talk about it more next week, since you're buying one of our packages." She giggled.

I gripped the massage table and, groaning, I arched my back, spraying rope after rope of cum all over her hands and the towel. It was a hard, intense orgasm, and she continued to pump my cock through it -- I came hard enough to see black spots in my vision and was panting and limp on the table when it ended.

She was standing by the door before I was coherent enough to realize. "Well, Rick, I know we're not at the end of your time, but I'm going to have to cut the massage off there; as a professional, I can tell when a client is at the limit of their ability to tolerate my particular style of pressure massage, and I believe we've reached that point. Maybe your...stamina...will increase in future sessions. When you're ready, you can toss the towel in the hamper over there and get your clothes back on." Smirking and shaking her head, she stepped out of the room. Dazed, I slowly dressed myself. As I was doing so, I heard her talking with the receptionist.

"Hi, Claire. Yeah, I know we aren't at time, we had to cut his massage short -- he was a little...sensitive to massage. First-timer, you know? But good news, I think it really relaxed him, and he wants to book the 3-month platinum package. Can you help him with that at checkout? Yeah, he said he wants the massages to be with me, so you can just work with him on my calendar. It's probably fine for them to bump right up against other appointments -- I don't think he's ever going to use the full time slot. Thanks!"

I let out a dazed sigh and put my clothes on. I felt disoriented, but one thing was for sure -- I had lost the bet. The only question was whether I was happy or sad to be buying a platinum package and seeing Olivia again next week.

CHAPTER 2

The week had started -- again -- badly.

My performance improvement plan began on Monday, and I almost immediately dropped the ball in an important client meeting with my boss. After the meeting in the elevator, she told me that she knew I was trying my best. Her eyes were sympathetic, even a little sad.

And without my usual doubles partner, I had signed up for some solo tennis -- but found myself getting circles run around me on the court, and lost every match. Wheezing after one match, I resolved to start trying to work on my cardio -- I didn't seem to have the endurance I had a few years ago. Part of getting older, I guess.

And, last and perhaps worst of all, I sporadically texted a bit with Emma, my ex-girlfriend. She was kind, but uncharacteristically firm with me. She was fine continuing to be friends but didn't see a future with us together. Any time I tried to say I was willing to change to try to meet her needs, she just said that they had been going unmet for a long time, and she didn't think that was likely or realistic. Which hurt. So it wasn't really a banner week, I thought, as I wrapped up work on Friday. But there was one big question mark at the end of the week: this massage appointment.

I stopped at home after work first, showering, and found myself jerking off in the shower. It was pretty easy to get aroused -- the experience last week with Olivia had been one of the hottest things that had ever happened to me, and I mentally played it back, getting to completion in no time. With the clarity that only comes after an orgasm, I felt a certain mixture of shame and embarrassment -- yeah, it had been hot, but she had basically been...mocking me for cumming quick. Why was I so turned on by that?

I mulled this over, not arriving at answers, but glad to have released some of the pent up sexual tension I was feeling, as I dressed and headed to the massage parlor. When I arrived, the receptionist recognized me. "Hey, good to see you back! You're a bit early. Olivia won't be ready for a few more minutes. Have a seat."

I sat and waited. Even though I had jerked off only twenty minutes before, I found that I was horny -- the prospect of seeing Olivia, I guessed. It was hard not to repeatedly play back the last session in my mind.

"Actually -- can I ask you something?" I glanced up to see that the receptionist was talking to me.

"Sure, what's up?"

"Well, to be honest, we don't get a lot of folks who have a first session that ends early, but still book a platinum package and come back. Usually if they can't even finish their session, they don't want to try again. Especially men -- I think they get embarrassed for not lasting longer, or something." She smiled. "I'm assuming you were happy with the experience. I'm wondering if you would write us a review online and maybe mention it was your first time and even though you couldn't last the full session, you purchased a package."

"I, uh...I'm not sure that part is what I'd focus on..." Even the reminder that I hadn't lasted the full massage was embarrassing. She gave me a pleading look "Please? You can talk about other stuff too, we obviously want honest reviews. But be thorough. I mean, you came early, so..."

"Uh...what?" Had Olivia told her?

My face must have changed, because she looked mortified and apologetic. "I mean, it's not a problem that you came early! We love it when clients show up early! It keeps us on schedule! I just meant that since you have to wait anyway, you can write a really thorough review...you know what, don't worry about it..."

"Oh, uh, no...hey...no worries...happy to do a review." I studied her, realizing that maybe she wasn't deliberately making double entendres. She was just a college kid. I needed to relax.

"Great -- you can use my computer if you like!" She motioned me over, and I joined her behind the desk. "My name is Claire, by the way."

"Well, nice to meet you, Claire. I'm Rick." She was six or seven years younger than me, maybe a freshman or sophmore college student doing this part-time. Petite, cropped blonde hair, blue eyes. Very young looking -- but pretty. I sat down next to her and started to fill out their online review form. I tried to make it as positive as possible. I was about three-quarters of the way done when someone behind me cleared their throat.

I turned around to an older woman, maybe in her late 30s or early 40s. She was...statuesque, that was the word. High heels only made her height more noticeable -- with the heels on, I was looking up at her face. Which was pretty, if angular -- green eyes, long blonde hair, high cheekbones, and attractive lips...that were currently drawn into a disapproving frown.

Claire hastily intervened. "Oh, uh, sorry, ma'am. This is one of our platinum package clients. He offered to write us a review when I asked and I figured, why not now? Hope that's okay. Rick, this is Natasha, my boss. She owns the parlor."

Natasha's frown eased, and the corners of her lips turned up. "Ah, I see. Thank you. And Rick, thank you, both for your patronage and for reviewing us. We're still trying to get our name out there, as it were, and I'm told reviews really help." She spoke with a faint accent -- something vaguely Eastern European, maybe -- and studied me, her eyes glancing up and down. Her smile seemed to have a different edge to it when she finished her examination. "You look like you carry a lot of tension -- I hope you'll consider continuing to return. I don't even need to touch your shoulders to see that you're wound pretty tight."

I blushed -- Olivia had used those words, at one point, during my last massage, and she hadn't been talking about the knots in my shoulders -- and nodded. "I really, uh, enjoyed my first session, ma'am." Why was I calling her ma'am? I was the customer here. "It helped relax me tremendously."

"I see. Good, good. Can I ask who your masseuse was?" My eyes had drifted from her face to her chest -- the woman had what I can only describe as an absolutely incredible pair of tits. Soft, inviting, and currently framed marvelously by the low-cut dress she was wearing.

"Uh...Olivia..." I was finding it difficult not to stare at her tits, but forced my eyes up. "She was great. She suggested the platinum package and uh....it seemed like a good idea...she was really persuasive..." I flushed a little saying it. I didn't want Olivia to get in trouble.

"Did she, indeed." Natasha nodded. "Well, you'll have to let me know after a few sessions if it helps. Her particular style of massage can be hard to take a full thirty minutes of. Some men find they don't have the requisite control..." -- did her lips quirk? -- "...of their muscles, you know, to sustain the full half hour. Did you, ah, wrap it up early?"

I flushed. What the fuck was with all the focus on how long these sessions lasted? "Uh, yeah. It was intense. But I felt very relaxed after."

Her smile reappeared, and her voice definitely had a bit of a teasing note in it. "Good, good. Well, if you find yourself having ongoing trouble handling Olivia, perhaps consider booking a session with myself, or one of our other practitioners."

What? Did she...know? "Uh, I --" I blushed and tried to keep my eyes from drifting towards her tits again, imagining what a massage from her would be like. "Thanks, I'll keep that in mind."

"Now, unfortunately, I have work to do. Thanks again for reviewing us and your continued patronage. Claire, make sure he gets a discount of some kind, or maybe one of our t-shirts. Whatever." She waved her hand, as if such things were beneath her, turned, and walked away. I watched her go.

"Wow, a t-shirt. She must like you. Normally she's, uh, kind of standoffish," Claire whispered. "I mean, she's a good boss, but she's definitely intimidating."

I nodded. I could imagine that.

I finished the review a few minutes later, just as Olivia poked her head out from one of the rooms. "Hey Rick, good to see you again." She had her dark hair in a ponytail, and bright red lipstick on. This week, jeans and a tight t-shirt accentuated her body. "Why don't you come on back."

I said farewell to Claire and headed back to the room.

The preliminaries were the same as my first visit: Olivia left me alone to disrobe, returning and dimming the lights a moment later. My heart was pounding, wondering what would come next.

"So, how was your week? I remember last week was rough -- any better? She began to knead my shoulders.

"Uh, a bit better I guess..." I was confused -- no acknowledgement of what happened last time? Are we just not gonna talk about it? But she kept plowing ahead with the small talk, and I certainly wasn’t going to be the first to raise…what had happened.

"Yeah? That's good then, but I gotta say, you're still carrying a lot of stress. Have you talked with your girlfriend at all since she dumped you?" She kept kneading my back.

I hesitated, not sure if I really wanted to talk about this with her. "I, uh, we've talked a bit...I don't think we're going to get back together."

She made a little sympathetic pouting sound.

I continued. "She, uh, doesn't really want to talk about why she dumped me."

Why had I said that?

"Aw, sorry, Rick." And then I heard the smirk in Olivia's tone before the words came out. "It sounds like she's trying to be nice. I tried to tell you about that last time."

"Uh, yeah, I guess..." Even just hearing the smirk I knew was on her face reminded me of last week, and sent blood rushing towards my cock. I didn't know what to say. I guess we are going to talk about it after all…

"You were on a performance plan at work too, right? How's that going? And...you play tennis, yeah?" Or maybe we aren’t going to talk about it... I felt off-balance; I couldn’t tell if we were having a normal massage or something else. I decided I'd lean in to small talk. She continued working my back as I relayed my many misfortunes to her -- client meetings flubbed, matches lost, the whole works.

"You know, Rick...you seem to have quite a few...performance problems." Her voice had lowered to a sultry tease, and I could tell that the smirk was back on her face.

"I-I'm just going through a slump--" but the amusement in her words was unexpectedly so fucking hot and humiliating, I could barely focus on what I was saying. I knew what she meant. My cock was rock hard.

"Are you, really, now." She practically purred the words out. "I just remembered that I asked you a few questions at the end of our time together last week and I don't think you answered." She paused in her ministrations on my back, and said "Flip over, please."

"D-did you? I'm not sure I remember..." As I was talking, I flipped over. There was no artful way to arrange the towel to hide the fact that I was rock hard.

"Well, it's hard to stay focused on anything but the physical sensations during massages sometimes." Her voice was mocking, and I blushed. "I asked you..." and her voice lowered again as she leaned over in my ear, "Whether you ever actually fucked your girlfriend, or if you always came before you could even stick it in. I mean, if it's just 'a slump', you must've performed for her at some point, right?"

"I-I'm not gonna talk about that..." My cock was throbbing, and my face was beet red.

"Oh, you don't want to tell me?" Olivia giggled. "How interesting. It must be really embarrassing. What if we made another bet, then. If I win, you have to tell me. In detail. Excruciating detail."

I considered this. "What do I get if I win?"

She looked thoughtful, pursuing her lips. "Mmm...I don't know....what do you want, Rick?" She said it seductively, provocatively. Looking at her in the dim light, with the shadows playing across her pretty face and full, pursed lips, with that bright red lipstick...my cock throbbed. I gave her the answer that any adult male human with a functioning penis would give in my situation.

"A...a blowjob. You have to go down on me." I blurted it out before I could think about it too much.

She chuckled -- a rich, low, throaty sound. "Well, well. How bold. I'm kind of impressed. Okay. If you win, a blowjob from me. Now, here's what I think we should bet on. I'm going to describe to you what I think your sex life with your ex-girlfriend was like. If I'm right, I win, and you have to give me all the juicy, embarrassing details about what you were like with her in bed. If I'm wrong...well, you get your blowjob." She blew me an exaggerated kiss.

It was increasingly difficult to focus on whether this was a good wager, but I was so turned on, I was past caring. What, she was going to guess the details of my sex life with my ex-girlfriend? That felt absurdly unlikely, I told myself. I sat up on the massage table, figuring that the pretense of a massage was over. "Okay, it's a bet. Tell me about my sex life, then."

She laughed, and sat down next to me on the table, tracing circles on my naked thigh. I shivered, and she started talking in a low voice.

"Well, I'm guessing your ex-girlfriend is pretty, but not that outgoing -- she's quiet. You were dating a while, but not so long...maybe two years? I don't think you lived together. You've wanted to, but you were hesitant to ask her, because you were worried she'd say no."

I blinked, coming out of my aroused haze for a moment, suspicion on my face. "Uh, yeah, that's all almost exactly right. How do you know all that? Are you friends with Emma or something?"

She giggled. "Emma, is it? No. I mean, I wish. I can only imagine the stories she’s telling her girlfriends now that she's dumped you. Women talk, you know. And I bet she's got some good stories."

She watched me turn beet red again, and continued. "No, I don’t know her…I’m just making guesses. Educated guesses based on what you've told me, but guesses. If you lived with her you would've told me about finding a new place or moving her stuff out or whatever when I asked about your week. She's gotta be kind of introverted or you would've been too intimidated to ever have a shot with her -- no offense," she added, with a laugh. But it stung, and I reddened even more.

"And I guessed two years because I think that's about as long as a relationship could last between a nice, quiet, introverted girl..." her voice took on a mocking tone, "...and a guy who cums too quick, before she goes looking to get fucked properly."

My cock was throbbing. I swallowed hard and nodded.

"I could make all kinds of other interesting guesses about you, knowing what I know. But I still haven't gotten to your sex life..." she looked me up and down, as if assessing. "Let's see...I don't exactly remember just how..." She reached out, underneath the towel, and grasped my cock, stroking its length. I moaned, helplessly. I wasn't expecting it and found myself right on the edge. Don't cum, don't cum, don't cum, I thought, trying to control my breathing. Fortunately, she released me after only a moment or two.

She continued as if she hadn't noticed my internal struggle at all. "Ah, right. You know, you're pretty big. Definitely enough to be impressive to a quiet, introverted girl. Okay. Here's my guess." She pursed her lips -- I stared at her lips, entranced, waiting for her to guess, wondering if she'd be wrapping them around my 'pretty big' cock. My bruised ego felt somewhat mollified by that remark.

"So, you're a bit skinny, but your dick looks pretty good. And your libido seems normal. I'm guessing you try to fuck her, say, once or twice a week. She's mostly receptive -- the girl's gotta be starving for a good dicking-down at this point, and your cock at least looks like it ought to be able to deliver that, so it probably doesn't take too much convincing." She grinned, and looked at me for confirmation.

I blushed. "Yeah, right so far, but that's not really--"

She cut me off. "Oh, I know, I'm not done guessing yet. Please try to hold back from interrupting...prematurely." She smirked. I blushed. "Where was I? Right, it probably doesn't take much convincing. I'm guessing, though, that maybe...mmm..." she paused, looking me up and down again, before continuing, "...let's say, like, half the time, you cum from foreplay. Not even an actual, focused blowjob or a handjob, just, y'know, touching her or her touching you while you're making out, stuff like that."

"I-I mean, I don't know if it's exactly half..." But the sinking sensation in my stomach was palpable, fighting with my body for arousal. I had no idea how, but Olivia seemed to know me really, really well.

"I said about half. The rest...well, most of the time you cum if she does anything, and I mean anything, involving your cock. Blowjob, handjob, titfuck...hell, I don't know if you guys use toys -- actually, there's no way you use toys, you don't have the sexual confidence -- but my point is, any attention on your cock for a sustained period of time, and you...pop." She mouthed and pantomimed an explosion. "Maybe...once every couple months, you get further than that."

"Yeah...." This was mortifying. She had me dead to rights.

"And that last fraction of the times you all are intimate...well, I imagine you're excited." Her eyes sparkled. "Really excited, to be getting inside her. So is she, I'm sure -- just dying to get fucked, hoping that nice, fat cock can finally live up to its potential."

That whiplash any time she paid my dick a compliment alongside the many insults to my sexual prowess was so unbelievably hot. I waited, trying to control myself.

She sighed, as if regretful for Emma. "But it's not to be. I bet you've never been inside her. You get as far as standing between her legs, or maybe you're looking down at her ass, while she's bent over. She says something, probably anything, like..." She thought for a moment, and then, adopting a breathless, moaning, tone, leaned in to my ear and said, "god, Rick, fuck me, please. I need that big dick in me. It's been so long."

I froze. I hadn't expected her to do that, to imitate my girlfriend begging for my cock, and I was unexpectedly, immediately, right back on the verge of cumming. I silently fought to keep control of my cock -- I wasn't even touching it! She wasn't even touching it! After a moment, I had staved off my orgasm, but only barely.

She watched my silent internal struggle for a moment with a wicked smile that turned pitying. "So...yeah. That's it. You've never really fucked her, and she dumped you after two years of watching you cum without an orgasm herself."

"Wrong!" I was elated. Well, elated probably wasn't the right word. I mean, it was mostly right, and it's not like the truth was really better, but...I had definitely won the bet.

"Oh? What part? It had better be something important." She looked like she was ready for me to try rules-lawyering my way out of something.

"I have fucked her." I looked triumphant.

"Have you now..." Olivia mused. "It seems unlikely, but I suppose, maybe..." She smirked. "How fast did you cum, though?"

"Nuh-uh." I said, trying to reason through the fog of arousal. "You only get the details if you won the bet, and you didn't. I've fucked her."

'Fucked' was probably not how Olivia would see it, but...

"Mmmmm..." she let out a low, throaty, hum. "Okay, describe where I got it wrong in broad terms; I just need to believe that you're not bullshitting me to know you won for real." She smiled. Her smile was very persuasive. Anything involving her mouth would have been very persuasive.

"Okay, that seems fair...well, you got most of it right, up till the end. I, uh...I usually don't make through foreplay. And then if I do and she goes down on me or whatever, I, um....yeah, that's it."

She giggled, and I blushed, the reality of the situation suddenly crashing home -- I was sitting, naked except for a towel, my cock throbbing, next to a hot girl, telling her about my sexual inadequacies. And she was laughing at me.

"So where was I wrong? You've said you fucked her?" She raised an eyebrow skeptically.

"I, uh...yeah. I mean...not for long, and not as often as I'd like, but...I've been inside her. Y'know, now and then." I tried to say it matter-of-factly, but somehow it sounded like a boast -- the saddest, most pathetic boast of all time.

"Mmmm...I'm not sure I believe you. Tell you what, give me a few additional details. If they check out, I'll believe you, and consider you to have won the bet." She looked at me seriously, and then blew me a kiss.

All I could think about were those red lips, wrapped around my length. "Okay...what do you want to know?"

She looked smug. "I want to know how long you lasted, generally speaking, and I want to know how she behaved after sex."

I blushed. Well, fuck, this was embarrassing. I thought about how to answer in a way that wasn't going to make me die of shame.

"I mean, if you don't want to answer, we can call this wager off..." she let the words hang, tantalizingly, in the air.

"N-no..." I thought quickly, and decided being vague was the best play. "I, uh, I lasted thirty seconds to a minute, most times." I hoped giving a time range would be enough.

But Olivia had a small smile. "How many pumps, Rick?"

"I....wh...that's pretty specific..." I muttered. "You didn't win the bet..."

She laughed. "Okay, you're embarrassed enough that I'm feeling like you're being honest. I guess you won." She stood up, and then kneeled in front of me. I blinked. It was actually going to happen!

"Oh...great...good..." I stammered, looking down at her kneeling between my legs. There was only a towel between my cock and her face. My cock twitched.

She smirked up at me. "Tell you what...while I get started, what if we keep talking about it? It's turning me on..." as she spoke, she kissed her way up the inside of my thigh. Her warm lips on my skin felt incredible.

I moaned, putty in her hands. I probably would've agreed to anything. "S-sure..." I could feel her mouth curve into a smile against my leg.

I was so preoccupied I barely even registered the question anyway. I tried to calm myself down, taking deep breaths. It was only now occurring to me that 'winning' might mean I only further embarrassed myself by cumming too fast during a blowjob from her. That was now a very real concern. Maybe talking would help distract me from the sensations I knew were coming -- those full, red lips, bobbing up and down...

Her voice snapped me back from my imagination. "So let's see...'thirty seconds to a minute', huh?" Her tone was sultry, her words punctuated by kisses, her mouth and hands both running over my thighs.

"...Maybe you do last that long, but I bet it's a lot of motionless holding in place, deep breathing, and careful, shallow movement. I bet that your best is about five pumps, but your usual performance -- when you make it that far -- is more like two. Two slow, weak, embarrassing 'thrusts' into her tight, wet, needy pussy, while you desperately try to control yourself, and then you just can't hold back anymore." She pulled the towel away from my crotch, giggling.

"You said you fucked her, but no real man would think of it as fucking her." She looked up at me, pretty face characteristically smirking, and I looked down at her, embarrassed. My cock -- throbbing, glistening with precum, and rock hard -- was only inches from her face. She glanced down at it, amused. "Such a quick cumming dick."

My throat was dry. This was making it harder to keep control, not easier. I swallowed. There was no way I was going to last very long for her mouth. And, worst of all -- she had guessed right. "Y...yeah..."

She giggled, again. She was running her hands everywhere but my cock now -- over my balls, up my thighs, over my stomach -- and kissing next to my cock. I could feel her breath on my length.

"And...what was my other question again? Oh yeah, how she reacts..." She pursed her lips, an inch away from the head of my cock, as if considering. "Let's see...she's quiet...introverted...nice...hmmm. I bet she mostly didn't say anything at all. But every now and then she would have said...something. It was just too frustrating for her. It wouldn't be rude or too direct..." her eyes lit up. "Oh, I've got it. I bet she starts by complimenting your dick..."

Ashamed, aroused, and with her mouth right there, I waited to see what she would say, hoping I'd be able to control myself.

"Let's see...she probably says something like...God, your dick feels so good...I wouldn't be able to take it for very long anyway, it's just so big, I'd get sore if you fucked me for too long, but maybe you could try to last a bit longer next time..." Olivia's tone was teasing, pouty, sarcastic. Emma had said things like that after we had had sex. But Emma had been kind, trying to build me up. Olivia said it like a bratty girl who wasn't getting fucked the way she needed, and who was going to be mean about letting you know that. I was right on the edge.

And then she bobbed once, twice, taking most of the length of my shaft into her mouth. I hadn't expected that, and I froze, trying to keep from cumming immediately. I felt her tongue, swirling around me, and moaned. She kept eye contact with me the whole time. She gave me one more pump inside her mouth, then pulled away, stroking my shaft with her hands, and looking up at me expectantly.

She had judged the situation correctly; the third pump on my cock, combined with her words, had been too much. My hips bucked, and I came everywhere. It got on her, the towel, the floor -- everywhere.

As my orgasm subsided, she giggled, wiping herself off with a towel. "Wow. Well, that was a whole three pumps. Above average for you, right?" She put a finger to her lips, as if considering. "Oh, but wait, I guess this was just a blowjob, not fucking. You know, if I was your girlfriend, I don't think you'd ever have the stamina to actually fuck me." She stood up.

I slumped, dazed. Fucking her...? The thought was intoxicating, but I knew she was right -- whatever mental games Olivia was playing with me, Emma hadn't done any of that, and I still couldn't last for Emma. I probably couldn't even make it inside Olivia without cumming. Her teasing was just so fucking hot.

"Anyway, congrats on winning the bet this week. I guess we're tied now, or whatever." She grinned. "Although I wouldn't let victory go to your head...that was the shortest blowjob I've ever given. I'm not even sure it counts as a blowjob. And you 'won' by explaining to me how, in fact, every now and then you were able to last five half-assed pumps inside your ex-girlfriend." I looked down, even more embarrassed. Worse, I could feel myself getting turned on by her words.

"Let's see. So, uh, we didn't use the full appointment time again, you lasted..." she glanced up at the clock. "Oh, dear. Not even ten minutes. I'm a little worried your tolerance for this style of massage is slipping, Rick." She put a look of mock concern on her face. "As much as I'm enjoying our sessions -- you're a great client -- maybe we need to go back to basics, and focus on your...stamina...next week. Take your time getting dressed, and if you don't mind, tidy the room up before you step out into the hallway -- it's a little messier in here than it usually gets, and I don't really think that's my fault."

She turned, and blew me a kiss from the doorway. "See you again next week."

As I set about trying to clean the room up, I realized I was looking forward to next week's session.

Through the haze of arousal and humiliation, I knew I was in trouble.

---

CHAPTER 3

It had been yet another bad week, but somehow, I cared a lot less.

My performance improvement plan continued at work. My boss and I were doing daily meetings at the end of the day to talk about what I needed to improve. She had always been kind, and it was clear she really didn't want to have to fire me. I was trying to get better, and maybe improving a bit -- but to be honest, I was distracted. It didn't feel as existential.

I canceled my tennis matches for the week and went running instead. What was the point of losing again? Sucking wind after the first mile, I almost gave up, but time alone with my thoughts felt...right, given everything that was going on, and that made it easier.

My ex-girlfriend, Emma, had gone radio silent over text. I missed her...a bit.

I was, to be totally honest, preoccupied.

I was replaying my last appointment with Olivia over and over in my head. She had teased me, gotten me to tell her how quickly I had cum with my ex-girlfriend, and then made me cum quickly herself. All in, like, ten minutes. She had me wrapped around her finger. All I could think about was her face, looking up at me, and the knowing smirk as I came.

Maybe preoccupied wasn't the right word. I was obsessed. I could tell it wasn't healthy, but I wasn't sure I cared. She was just so fucking hot.

One question kept running through my mind: why the fuck couldn't I last longer with her?

I mean, I wasn't hoping to be some marathon man. I had always cum quickly. Sex with my ex-girlfriend Emma had been...well, consistently brief.

But even so. With Olivia, my arousal was on a completely different level. I felt like I was barely holding it together just listening to her talk. I was on edge from the moment she opened her mouth. It was embarrassing. Humiliating. As I thought about the last two appointments, I was pretty sure I had only lasted as long as I had...because she had let me. She was keeping me on edge, and I was cumming exactly when she wanted me to.

It was hot. But I had to get myself under control. I wasn't going to skip our next appointment -- that would be admitting I couldn't handle her -- but I wanted to show up relaxed, focused, and...well, I wanted to last.

Friday rolled around. I jerked off twice -- once in the morning, and once after work. Emptying the chamber had sometimes helped me last a little longer with Emma. And it wasn't like I was lacking for spank bank material after my last session. Olivia's mouth around my cock, her mocking moans, and the teasing...it was way too easy to cum when I thought about that while I jerked off, which was even more humiliating.

But it did help me clear my head. When I showed up at the massage parlor a few minutes early for my appointment, I had slightly more equilibrium than I might have otherwise. I waved to Claire, the receptionist, who greeted me with a cheery smile.

"Hey, Rick. You came early again! So punctual!"

Did she have to phrase it that way? I reminded myself that she was just a college kid. I was sure Olivia hadn't said anything to her.

I made small talk with Claire for a few minutes; it was obvious I was now "a regular" in her mind. She was indeed a student at the university, and worked here part time. She was a kinesiology major; she hoped to become a physical therapist and had thought a massage parlor would be a good gig for her resume. She was animated, enthusiastic while she was talking about her hopes. Her enthusiasm was infectious, and now that she was out of her shell, I found her attractive -- in a naive, youthful, bubbly kind of way. It was fun to talk to her.

"Olivia actually mentioned to me that you might come early." Claire smiled.

"Did she?" Claire's word choice was unfortunate, but probably innocuous, I told myself. But I was sure Olivia's phrasing had been deliberate, and I didn't like that she had mentioned anything, to anyone else, about me.

"Yeah. And you know, since you seem to come early so consistently, I actually had a question for you." She looked incredibly nervous. It probably didn't help that I was wincing every time she said that I 'came early'.

"Sure, Claire. What's up?" I was undeniably curious.

She was stammering, obviously anxious about making the request. "Well, um...for one of my classes... I'm supposed to put in some practice physical therapy hours on volunteers....and Olivia was talking about your sessions...she, uh, mentioned she's had to cut some of your sessions short...I was wondering if I could practice on you? It might really help you out with your sessions lasting longer..."

I almost choked. "Olivia...mentioned...what? What about cutting our sessions short?" I was ready to die of shame. And what kind of PT was Claire talking about?

"It's nothing to be embarrassed about!" Claire said quickly. "I actually think it's kind of cool!"

"Y...you do?" The shame faded a bit, and now I was just...confused.

"Yeah, I think it's great for people to keep playing sports as adults, and shoulder injuries are really common for tennis players. Of course that limits your ability to receive intense massage. I think I could probably help you out...you'd be able to handle more massage, and we could work on range of motion, that kind of thing, it'd help your tennis game..." She trailed off at the look on my face. Her face was anxious, worried she'd somehow offended me...but otherwise, totally guileless. No double entendre, no teasing meaning. Just a pretty college girl trying to meet some kinesiology course requirements.

Fucking hell. Olivia had really gotten inside my head. But it did seem like Olivia hadn't been talking about my sessions with Claire after all. Still -- as I looked Claire up and down, it was hard not to think of the petite blonde giving me a completely different kind of PT than was taught in a kinesiology curriculum. Relax, I thought. Focused for this session with Olivia. You're going to last. I tried to course-correct.

"O-oh, okay...yeah, I'd be happy for you to practice on me..." I was sure I was blushing, but Claire's enthusiasm and relief were so obviously overwhelming that I'm not sure she noticed.

"Great! Thank you so much. This'll really help me out. Maybe you can just show up a half-hour early to your next appointment? I'll clear it with Natasha but we should have rooms available." I nodded.

Olivia chose that moment to walk down the hallway. "Hey, Rick, good to see you again. I'm ready for you. Come on back."

I stood up, and realized the conversation with Claire had gotten me semi erect. Jesus, get it together. She isn't even teasing you on purpose. I surreptitiously tried to adjust myself as I followed Olivia.

Olivia was wearing tight-fitting slacks -- I stared at her ass as she walked ahead of me down the hall -- and a polo shirt that revealed more than a hint of her tan cleavage as she looked back at me. Her dark hair was tied back in a ponytail again.

She flashed me a smile as we entered the room. "So, remember what I said last week?"

I tried to recall if there was something specific. "Uh..." The only thing that came to mind was the sight of her, kneeling between my legs, smirking as she said 'Such a quick cumming dick.' I suspected that wasn't what she was talking about, though.

She laughed. "I guess we talked a lot, huh? I meant what I said at the end. I'm a little concerned about your stamina. I know this style of massage is intense, but you're not really fully utilizing our time slot. I looked back, and in our first session you lasted fifteen minutes before we had to wrap it up....but last time you only lasted, like, ten. I gotta be honest, most men can last a lot longer than that, and it's rare for the second session to end so much faster than the first." She paused, waiting for me to respond.

I reddened. I already knew she thought I came embarrassingly quickly, she didn't need to rub it in with comparisons. "Olivia, I..."

"Claire mentioned that she was going to ask you about letting her do some PT on your shoulder next time before our session. I think that's a really good idea -- she's not licensed but she needs the training hours, so it'd be free, and I think you'll benefit immensely."

Ah... Like last time, her tone was starting off completely non-sexual. Gotcha. I resolved that I wouldn't let that throw me off, and I'd just roll with it. "Yeah, she mentioned that in the lobby just now -- I said yes. She seems really nice."

"Great." Olivia nodded. "Yeah, I like Claire. She kind of reminds me of your description of your ex-girlfriend...Emma, right? Nice, kind. Claire's a bit introverted too, it takes a bit to get her to warm up to you, but she's super friendly once she opens up. She's a lot younger than you, though, so don't get any ideas about dating college freshmen, mister." She grinned, and faux-punched me on the arm.

"R-right..." I tried to be normal. Nonchalant. Not to think about what it'd be like to have a massage session with Claire.

"Anyway, go ahead and disrobe to the level of your comfort; I'll be back momentarily..." she breezed out.

I swallowed hard, disrobed, and got on the massage table with the towel over me. Olivia returned and dimmed the lights, and moments later, I felt her hands -- slick with oil -- on my back.

"So, have you noticed that you're feeling less stressed since you started coming here?"

I considered this. "Actually...yeah. It wasn't a great week or anything, but I don't feel as frustrated."

She made a pleased sound. "That's great! The connection between our bodies and our mental state is so deep and profound. Can't say I'm surprised." She was kneading me with her hands, working her way down my back. "Any more conversation with Emma? Mending things?"

"No...y'know, I think we both just recognized it wasn't going to work out. Maybe I'll reach out in a couple of weeks or something." I tried to relax. For the moment, it felt like a run of the mill, normal massage. Maybe she's done having her fun?

"Sure, you could do that." I could hear the knowing smile in her voice. "Although, y'know, when people break up because someone's needs aren't getting met, sometimes there's not much point in reconnecting..."

I took some deep breaths. Ignore the teasing. "Yeah, I guess you might be right. Anyway, I'm feeling okay about it."

"Well, good. I hope the massage is helping you to feel more even-keeled."

I almost laughed. These sessions were the most confusing half hour of my life, every single week. Well, most confusing...ten to fifteen minutes. "Even-keeled isn't the word I'd pick, but yeah, I think they are actually helping."

"Good. There's actually...something else I wanted to raise with you." Olivia's hands continued, but her voice had shifted. "I've been thinking about our little bet from last time..."

My cock jumped. I was lucky I didn't pass out, the blood rushed out of my head and into my dick so fast. "Y-yeah?" Fuck, so much for her being done having her fun...stay calm... I tried to take a few deep, steadying, breaths.

"Well, I know I said you won the bet, but..." she leaned close to my ear. "I don't really think that's true, do you?"

My heart was pounding again. I was still face-down, and her hands were kneading lower, working my hamstrings and my ass -- her proximity to my balls, and my rapidly hardening cock, was intoxicating. "I mean, yeah, I think--" I stammered.

She continued, as if I hadn't spoken, a mocking note in her voice. "I was mulling it over. I know you thought you were fucking Emma. But I don't really think you know what it's like to actually fuck a woman." One or two fingers gently grazed my balls between my thighs. I moaned. Fuck. My hope to keep it together and not let her get inside my head was rapidly disappearing in the haze of arousal. How is this always what happens, I thought helplessly.

"I--yes--I--" I was trying to form words, but mostly failing.

She cut me off. "Oh, I'm wrapped up on your back now. You can flip over." The teasing note in her voice was unmistakable. I flipped over, too turned on to even think about trying to hide the way my cock was tenting the towel up.

She started rubbing oil into my chest, making eye contact while she was doing so. "Anyway, I'm sure you thought you were really railing her, or whatever." She rolled her eyes. "But I don't think you really ever fucked her."

I paused. "W-what do you mean? I..."

But she just pressed on. "I mean, it sounds to me like you put your cock inside her, and then just kind of...held still, quivering, trying not to cum..." she made some pathetic mewling sounds, a very emasculating impression of me, "...for like thirty seconds before you blew your load. Maybe one or two halfway-in, halfway-out pumps in there, but not like, actual fucking."

I flushed with humiliation. She wasn't far off, but..."I-I have fucked her."

"Mmm, I don't think so. I don't think that counts. So I think I won last week's bet." She looked smug.

"Wh-what, no, you can't just decide that! You're just mad you didn't guess correctly!" I was indignant. I had won the wager! Yeah, I hadn't ever lasted very long with Emma, but...but I had certainly fucked her...hadn't I?

"Hmm...." She pursed her lips, continuing to massage downward towards my abdomen. "Well, what about another wager that could help us resolve our difference of opinion?"

"W...what kind of wager?" I was embarrassed, humiliated by this line of conversation...but I was also rock hard, wearing nothing but a towel, with a pretty girl running her hands down my chest. So I was feeling open to further discussion.

"Well, if there were some way for you to show me that you know how to fuck a girl, in spite of all the evidence to the contrary..." she mused. Her hands kept going lower, pulling my attention from her words.

"I---I do--" I tried to insist, but I trailed off into a moan as she traced one hand up my thigh, brushing against my balls.

"Of course you do, Rick." Her tone was patronizing and she made eye contact with me. "I mean, I'd let you try to fuck me, to show me. But we both know that what would happen definitely wouldn't count as fucking."

"I could--" but I stopped as she grabbed the base of my cock and gave me a single, agonizingly slow, pump up and down with one oil-slick hand.

"Rick." She leaned in, her voice soft. "Come on. The idea that you could handle being inside me -- let alone thrusting in and out of me -- is...cute."

I flushed. It was embarrassing how right she was -- I could feel how on edge my cock was. If I kept thinking about fucking her, I'd probably cum. I looked away -- aroused and humiliated, wondering if she'd make me blow my load just to prove her point.

She didn't, though -- after a moment she pulled her hand away. "No, we need another way..." Her eyes lit up. "Hmm...." She stepped away. "Rick, I'll be right back, I just need to grab something. Maybe try to, uh, get yourself under control, so you've actually got a shot at winning a bet. I've got an idea for how to settle our disagreement."

I waited as she left the room. She was gone about thirty seconds. It was amazing how active my imagination got during that time. I tried to calm myself down, but the uncertainty was maddening. What the fuck was she getting?

She came back into the room with a wicked grin on her face, shutting the door behind her. "Okay, here's the wager. In addition to this massage parlor, Natasha has a couple other businesses...including one that makes a line of sex toys." She smirked. "We're gonna see if you can fuck this."

She produced a tan, fleshlight-looking device, holding it up for me to see. "It's a masturbatory device. You -- well, I'll do it in this case, I don't really think you actually know how women move when they're getting fucked -- pump it up and down your cock, thrusting into it, and--"

"Yeah, I mean, I get how it works, Olivia." I blushed. I had seen toys like these before, but never used one.

She laughed. "Good. So here's the bet." She glanced at the clock. "If you can fuck this for...let's say...five minutes, since it's not actually a wet pussy...I'll agree that you won our last wager; I was wrong about your amazing sex life with Emma." She paused, letting the sarcastic words hang in the air.

"But if you can't, you've gotta agree that you've never actually fucked a woman before. Sticking your dick in someone motionlessly for thirty seconds before you blow a load isn't fucking."

I considered, trying to imagine what it would be like to have Olivia using that toy on me. She was so good with her hands...and I knew she'd be talking the whole time...I didn't like my odds.

I flushed, before timidly saying, "Uh, maybe three minutes? Five minutes feels..."

She laughed. "Wow, such a confident guy...Fine, three minutes. I don't really think it matters. I'll have you cumming in way less than that."

That stung -- it was embarrassing that I was the one talking her down about how long I could last. I tried to think about some way to salvage a semblance of manhood. "What if...we raise the stakes?"

She looked intrigued. "I'm listening."

"Well, whoever wins, we agree they won last wager...and on top of that...if I win, I get to fuck you." I tried to say it without a tremor of arousal in my voice, but failed.

She smirked. "You really want to fuck me, huh?"

I nodded. I didn't trust myself with words. I wanted it so fucking badly. I was obsessed with her.

She whispered in my ear. "I guess if you really do know what fucking looks like, we could do that. Even though you'll cum right away. Deal."

I was elated. Three minutes...I can make it three minutes... I started taking deep breaths, trying to calm myself down, willing my cock to be less rigid.

Olivia thought for a moment, and then looked smug. "Okay, but those are some high stakes. So, if I win, you have to send Emma some text messages I write on your behalf, and send me her replies." She leaned forward. "I really want to hear her side of the story...how she finally had to break up with her quick-cumming boyfriend after two years of not getting fucked the way she needed."

"Wh-what?" I was shocked.

She smirked. "They won't be anything weird, and if you're really uncomfortable, you don't have to send them, or I’ll reword them. But I bet I can get her to tell you all about your...shortcomings...under the simple guise of closure."

The sinking feeling in my gut was palpable. I wasn't sure I really wanted to hear directly from Emma about how dissatisfied she'd been, let alone having Olivia hear specifics from Emma..."H-how many texts?"

She thought for a moment. "How about ten? That's enough for one conversation if I play my cards right."

I mulled it over. "I-I don't know Olivia..." but I trailed off, speechless. She was stripping off her pants. She was wearing a sporty thong, which showed off tan, athletic legs and a well-sculpted ass.

"Rick..." she moved back over, closer to me. "Come on, you're not gonna get back with her either way, right? You really want to fuck me, right? High stakes, Rick. Risk...and reward." As she spoke, she climbed up on the table. She was straddling me, now, groin-to-groin -- only a towel and her thong between my cock and her pussy. I could feel the heat radiating from her.

"Okay..." There was no way for me to say no, no way to resist. She smirked.

"Hey, you just have to make sure you win, right? So...three minutes...starting...now." She looked back at me from the clock. "Mmm, plenty of time. I think this is a great opportunity for some stamina work, don't you think?" She whipped the towel off of my cock.

"Huh?"

"Rick, I'm trying to help you out here..." she said, mockingly. As she spoke, she was lubing up the toy with massage oil. "...we need to work on you being able to tolerate these sessions for longer. So I won't give you all I've got right away. Who knows...maybe this way you'll actually win the bet." Her tone made it clear that she thought that was incredibly unlikely.

"Oh...I mean, that sounds gooo--" I moaned, as, making eye contact with me, she slowly sank the sleeve of the toy over my cock.

"Mmmm," she purred. "Such a tight fit." She had about half of my cock inside the toy; I could feel it gripping my head and the upper half of my shaft. "You really do have a nice, thick cock. If only it could last..." She pouted, still staring into my eyes.

I was silent, focused on keeping control. The toy felt...well, it felt a lot like the real thing, and having Olivia on top of me, straddling my lap...the sight of her legs over mine...it looked a lot like the real thing too. It was all too easy to imagine that this was what it would be like to have her riding me. I tried to push the thought away.

She giggled. "Are you thinking this is what it would be like to fuck me, Rick?"

I nodded helplessly, and her giggle turned into a laugh -- a mocking one.

"Aw, Rick. It wouldn't be like this at all. For one thing..." she leaned over me, pushing her tits against my chest so she could whisper in my ear, "I could take your whole cock. You're big, but I like big. I'd ease down onto you, just...like...this..." She bit my earlobe, and sank the sleeve of the toy the rest of the way down, so that my entire length was inside it. As she did that, she moaned -- exactly the way she might if she were adjusting to my thick length bottoming out inside her.

I froze, willing myself not to cum. God, she was just so hot....

"Now this is nice...but it still isn't fucking yet, Rick. I know maybe this is what you're used to, just holding still with that big dick buried in someone..." she teased, "but typically there's a little more motion involved. Why don't you get used to the sensation, and then we can proceed. This is good practice."

I tried to pull myself together, but it was almost impossible. I couldn't form words. Looking up at her in the dim light -- the knowing smile, her dark hair, her tits against my chest -- combined with the sensation on my cock, and her mocking tone, was so much.

She could tell I was struggling. "This is about as far as you would get with Emma, huh?" She laughed, false sympathy in her voice. "Aww...thrusting is just too much for you...I can't wait to get all the details out of her..."

I blushed. I was so close to cumming already, and she was right -- there had been a lot of time motionless inside Emma, trying not to cum.

"But you know what, Rick? Emma sounds like a pretty demure girl. She's nice. Reserved. She probably didn't like to be on top, huh?" She didn't bother waiting for a reply, she just continued. "I'm a little different. I like to ride..." and as she spoke, she started pumping the toy up and down on my length, and gyrating her hips as if she were actually riding me. She leaned over me, continuing to pump, her ass bouncing off my thighs, and whispered, "especially such a nice, thick cock...it has to be able to last, though, so I can get off too..." and she moaned again in my ear.

This was it. I gripped the massage table, trying to keep control. But there was no way. Ten seconds of this and I'd be cumming. I didn't stand a chance. But just as I was about to hit the point of no return, she stopped.

"But...you know…this still isn't really what fucking me would be like." She grinned, wickedly. "You haven't touched me, or even said anything, Rick. You're just lying there like a starfish trying not to cum."

I blinked, and she gave a snort at the confused, slightly hurt expression on my face.

"I'm fucking you. If you want to fuck me, you've gotta...I don't know...do something...anything." She smirked. "But I bet you can't. Not without your quick dick exploding."

That stung my pride, and I finally found some words. "I--I can--"

She laughed. "Oh, yeah? Okay then. Let's see. It's been..." she looked at the clock. "Oh, wow. One whole minute. Good for you. Two minutes to go." I glanced up at the clock. She was right. Fuck, only one minute?

Her tone was mocking as she continued. "I'll tell you what. If you can fuck the toy -- really fuck the toy, thrusting into it, hands on my body as if you were fucking me -- for fifteen whole seconds, you don't have to make it the whole time. I'll consider that a win for you. And then...we can fuck for real." She bit her lip. "I have to admit, if you could really fuck...well, like I said, you've got a nice dick, and I do like them big. I'd be into it...for, you know, all two of the pumps you'd give me before you started cumming."

My cock twitched, and I almost came right there. There was no way I was going to last through two minutes of this, with her on top of me, teasing me while I tried to hold still and not cum. Fifteen seconds...well, maybe. It was a lot less time, even if it was going to be more intense…

"Okay...deal." I tried to mentally prepare myself for this. Fifteen seconds...it's only fifteen seconds... I tried not to think about getting to fuck her if I succeeded, worried it would only make me lose control more quickly.

"Mmmm...okay..." she murmured in my ear. "Grab my ass and start whenever you're ready...big guy." Fuck, everything that came out of her mouth was almost enough to make me cum.

Slowly, trying to keep my breathing even, I grabbed her ass. It felt amazing, round and toned. I squeezed it, and she giggled in my ear. I felt her flex under my hands. "Mmm, taking your time, huh? Fair enough...the clock doesn't start until you start thrusting, though...so you had better not cum from feeling me up..." She started moving a little, letting me feel her butt moving against my hands. Fuck. I tried to stay calm, but I worried I would cum from feeling her up. I needed to go for it.

I took a deep breath and started thrusting. As I did, she began moving the sleeve up and down my cock, twisting it as she met my thrusts, and bouncing her ass under my hands. It was too much almost immediately -- the toy felt amazing, her body moving felt incredible...it was what I imagined her riding me would be like, with her ass in her hands and the way she was driving the toy down to meet my thrusts. I got maybe three thrusts into the toy, and could tell my orgasm was inevitable -- but I was trying to hold on as long as I could.

Maybe I could just hold it back for fifteen seconds?

And then, in my ear, she moaned, "Oh, Rick, that big dick feels so good, don't cum yet, keep going --"

As you might imagine if you've been following along this far, that was way more than I could handle. I got out a strangled "oh, fuck, Olivia--" that dissolved into a moan, as I immediately came buckets into that toy, rope after rope.

She kept pumping it up and down my shaft, her ass bouncing atop me, and her tone shifted, to mock-disappointed-lover, as she plaintively moaned, "Aw, baby, no, that was so fast..."

As my orgasm subsided, I flushed with shame. Fuck...I came right when she wanted me to cum...yet again. "Olivia, I..."

She giggled at my embarrassed look. "To be honest, you made it further than I thought you would. Can't believe you actually had your hands on my ass without blowing your load. There's still no way you could handle fucking me, obviously. But we'll call it progress on your stamina." She wiped some of the massage oil off herself, cleaning up a bit, and started putting her pants back on.

"Uh..thanks, I guess?..." I was dazed, and in no condition to respond.

"Anyway, I win. Again. Put your number in my phone. I'll send you the first text for Emma later today. I'm gonna want you to send them late at night -- any time after like, 11pm is fine. I want replies from her with late night vibes, not whatever she'd say on her lunch break at work. Just send me what she says as you get it, and I'll text you what to say back." She said all of this with a little glee in her voice. "I can't wait to hear what she has to say about your performance."

Oh. Right. "Okay...you did win..." The bliss of the orgasm was fading, leaving me crestfallen and more than a little worried as I put my digits into her phone.

She pouted. "Aw, Rick, don't be so down about it...I know you wanted to fuck me, and since I won, this does mean you've lost all our wagers so far. You're 0-3. But hey, this appointment lasted -- " She glanced at the clock. "-- sixteen whole minutes! Better than your first one, even. And you looked like you enjoyed the session."

She smirked, looking back as she walked out the door. "Anyway, I'll be texting you. Remember -- thirty minutes early for the next appointment, you've got PT with Claire. We'll have lots to talk about in our next session. See you next week!"

What the fuck was she going to have me say to Emma?