The Masseuse (Ch. 14-20: Betrayals and Blackmail) (Patreon)

CHAPTER 14

It was Wednesday night, now. I was due to go to the massage parlor tomorrow to meet with Natasha for additional control data...and to talk about Brittany.

I was anxious about it. Racing thoughts kept me from sleeping. What if Natasha didn't take my advice? What if Brittany started working there, became friends with Olivia and Claire? Learned even more information to make fun of me with?

I tossed and turned for a long time before I finally fell asleep.

---

Thursday.

The parlor was somehow darker than it usually was, more poorly lit.

Natasha greeted me at the door, locking it behind me, and led me back to one of the massage rooms. "Sit down here, Rick. I've decided upon a way to gather some new...testing data, and also for you to weigh in on the hiring matter you raised." There was a single chair set in the center of the room.

I sat down. "Okay, how?"

Brittany stepped out of the shadows, looking at me curiously. She was dressed in a similar outfit to the one Olivia had worn in the photo shoot. Stiletto heels. Tight leather pants clung to the curves of her ass. A corset pushed her tits up, accentuating her tiny waist, and left her pale shoulders bare. Her long dark hair fell in waves down her back. And her brow was furrowed, a look of confusion on her face, that was quickly replaced with one of contempt.

"Natasha, what's he doing here? I thought we were going to keep doing my interview, or maybe some other tests?"

Natasha smiled and stepped back to the edge of the room. In the dim light, her face was shadowed. "Rick is a business partner of mine, Brittany. His input on my business decisions is extremely important, including on hiring. He has some reservations about your candidacy. It will be up to you to change his mind; I'll observe."

Brittany considered this, glancing between me and Natasha a few times before focusing on me. "Aw, Rick, do you not want me to work here?"

She stepped forward to stand right in front of me. "Why not?" She pouted.

"Y-you're a jerk, Brittany. You've basically always been rude to me..." but I trailed off as she leaned in closer, her face inches from mine, her full tits pushed together from the corset. She was so fucking hot. I felt my face flush. Shit.

"You're just worried everyone will know what a quick cummer you are, huh?" she whispered.

She trailed a hand up the inside of my thigh; I shivered. I could feel myself getting hard. "You know, I still think about that night at the club...when I was grinding on you..." She was still whispering.

"Y-you do?" I swallowed.

"Mmm, I do. You were so big and hard... and I bet if I had kept going I would've made you cum in your pants, huh?" she smirked. She continued to trail a hand up and down my thigh -- and every time she went back up, she got a little closer to my cock.

I didn't say anything. It was bad enough that she was getting me hard.

"I didn't know it at the time, not really. But now...with all the stories Emma told me..." she giggled. "Well, it's obvious in retrospect. You were probably about the blow your load on that dance floor, weren't you?"

As she spoke, she moved in closer, kneeling between my legs and starting to unbuckle my belt.

"It doesn't matter..." I muttered.

She looked up at me, frowning prettily. "I mean, it kind of does, don't you think? That night you obviously found me attractive...and..." she unzipped my pants, pulling both my pants and my boxers down and revealing my throbbing length. "...yeah, I think you still do, don't you?"

I looked away.

"So why don't you want me to work here?" She was running her hands over my bare thighs, now.

"Like I said...you've been nothing but rude to me..." I tried to focus, but her hands on my thighs made it difficult. My cock twitched, and I could feel myself leaking.

She cocked her head, her hair falling to one side. "Then why are you so hard? You look really turned on..."

I spluttered. "You-you're hot, but that doesn't mean..."

She giggled. "Aw, thanks Rick. That's sweet. I guess I see what you're trying to say. You don't like that I tease you about all the stories Emma's told me about you cumming quick. You don't like that I heard you blow your load in like, thirty seconds -- with breaks -- while you were fucking my roommate the other day. You don't like that I texted you to make fun of you. And you probably don't like that you're so turned on right now for me in spite of all that. Right?"

Her hands were impossible close to my cock now.

"Yeah, exactly." I tried to say it with certainty, finality. But it came out like I was grateful she had explained it more clearly than I could.

"But that's not really what's going on here, Rick." She looked up at me seriously. "What you really don't like is that I know exactly what you are."

"W-what? You don't--" but I cut myself short with a gasp as she took a single finger and stroked it from the tip of my cock -- where I was leaking precum -- down the bottom of my shaft. She kept flicking it up and down over the point where my thick head met my shaft.

"You might have been able to fool Emma for years. Maybe you'll fool Claire for a little while. But you can't fool me. I know the truth. You love how quick you cum. You love losing control for pretty girls. Pretty girls like me." She smiled, her eyes on the tip of her finger sliding up and down.

I couldn't form words. The stimulation from her finger wasn't enough to make me cum, but I was so turned on, it was hard to even think.

"In fact...you want me to make you an even quicker cummer, don't you?" Brittany said, smiling wickedly. "You want me to make it so you can't even look at Claire -- or another woman -- without blowing your load."

"Nnnooo," I moaned. I didn't want that. I wanted to last longer, not cum even faster than I already did. But her finger on my cock was driving me crazy. It wasn't going to make me cum, but I could feel the need growing.

"Mmm, you say that...but then why do you keep coming back to the massage parlor, Rick? If you don't like cumming so fast, why do you keep seeing Olivia?"

How did she-- but I couldn't think straight.

"Nn..." the word turned into a groan. I had to cum.

"No? You sound pretty turned on, though...I mean, you at least want me to make you cum, right?" The smirk on her pretty face was so sexy.

I nodded frantically.

She adopted a look of concern. "I'm not sure that's such a good idea, though...if you cum from this little stimulation, Rick, you'll just get faster and faster...I'm only stroking you with one finger..."

Was that true? Did I care?

She pouted, continuing to run her finger up and down my shaft. "I mean, if you don't want to cum quickly, I shouldn't make you cum...it'll just be helping to ruin your stamina..."

"So...are you sure you want to cum? I'm confused...I'll help you if you want, but that seems like you do want to cum faster," she said, a puzzled expression on her face.

"Yes, I...N-no...fuck..." I was desperate, needy. I tried to buck my hips, to thrust against her finger to get more pressure and sensation, but somehow she anticipated this, and kept things exactly the same -- her one finger, lightly stroking up and down the most sensitive part of my cock.

"Your big dick will be even more useless than it already is...are you sure that's what you want?" She blinked innocently up at me.

I didn't know if what she was saying was true or not, but I had to cum. "Brittany, please..."

At the word, her eyes lit up. "Oh, what a good boy. So polite. Please what?" Her finger was relentless, continuing to flick up and down.

"Please...make me cum..." I gritted the words out.

"Is that...all you want?" She pursed her lips. "I think if you want to cum so badly, then you also want me to make you an even quicker cummer, right? Say please, Brittany, help me blow my load even faster. She looked expectant.

I flushed with embarrassment and humiliation. But I had to get off. "Please...make me blow my load...even faster..."

Brittany giggled, delighted, and pulled her fingers away. "Okay...let's see how many pumps from my whole hand you can handle...Emma said that handjobs were how you generally lasted the longest. Mm, you're thick..."

She wrapped a hand around the upper part of my shaft.

I was silent, needy and ashamed. I could feel I was right on the edge, and I knew this was going to be fast, was going to confirm her impression of me, was going to confirm what she was saying that I'd just cum faster and faster -- but I wanted to cum so badly that I didn't care.

With a tight grip, Brittany pumped up and down. "One..."

Moaning, I exploded immediately -- the contrast between her single finger on my length and her whole hand enveloping me was just too much.

She pulled her hand away instantly. I helplessly bucked my hips, thrusting, trying ineffectually to get some additional sensation on my cock, anything. My orgasm ruined, I groaned, breathing hard.

She grinned. "Aw, over so fast...you must like me a lot more than Emma..." She blew me a kiss.

Natasha stepped forward. "Well that was...interesting. Rick, has that changed your mind at all?"

---

I snapped awake. I glanced at the clock. 4:22AM -- early Thursday morning. It had been a dream.

A wet dream, I realized, the feelings of embarrassment and shame that I was already feeling intensifying. I mulled that over as I changed my sheets. I didn't want to cum more quickly. I felt firm in that. But...there had been something undeniably hot about what Brittany had been doing.

Fuck. This wasn't what Natasha had in mind...I hoped.

---

CHAPTER 15

As a result of the dream on Wednesday night, I showed up anxious and trepidatious.

Natasha greeted me with a broad smile. "Well, it's official now. You're in on the business." She was wearing a tight-fitting, low cut red dress and black heels, like maybe she was going to a gala or a cocktail party after we wrapped up here. She looked classy...and hot.

"Uh, thanks...that was a lot of legalese..." I had signed both an NDA and some additional paperwork earlier in the day. I shook her hand. As usual, her touch was warm, sensual.

"Don't sweat it. As long as you're not stealing company secrets or tweeting about stuff or whatever, you'll be fine. If you are, I'll have you by the balls." Still grinning, Natasha ushered me inside the massage parlor, locking the door behind me. "Now...would you prefer to discuss the HR matter you were interested in first, or do the control testing I have planned for tonight?"

"Uh...let's tackle the hiring thing first...Brittany..." I took a breath. I had thought a lot about what I was going to say. My eyes kept wandering down to her body in that dress, though...

Natasha waved a hand. "I decided not to hire her."

"Uh, what?" That simple? And after that weird fucking dream I had?

Natasha nodded. "My businesses are fundamentally about giving other people pleasure, relieving tension, things like that. I could tell from talking to her that Brittany isn't...really about that. The way you reacted confirms it. I like teasing and power dynamics as much as the next person, between consenting adults. She's...well, almost cruel. That's different, and it's not what I'm looking for in someone who works for me."

"That...that makes a lot of sense..." I was still stunned. I felt a sense of relief, but also like...it had been too easy.

Natasha laughed. "Anyway, come on back." She led me into one of the massage rooms.

"As I mentioned, I need more control data to improve the harness. The best way to gather that is to see how you respond when you're having intercourse with a woman, without the harness stimulating you." She paused. "Let's say, three minutes of data or so would be a good start; we can see how that improves the modeling."

I blushed. "Uh, three minutes of, like...penetration?"

She nodded.

"Okay...uh...all in one session?" Maybe if I held really still...

She grinned. "I thought you might ask that. Yes, one session, Rick. 3 minutes of control data. It's not that long. Let's get you in the harness..."

As before, she started strapping me into the mesh harness, attaching electrodes and various sensors. While she spoke, she kept talking.

"Now, we'll needed someone else to monitor the data. So I asked for one of my other business partners to come help."

For a moment, my heart stopped. But then Olivia walked into the room, dressed in jeans and a t-shirt, carrying a laptop. She gave me a smile. "Hey, Rick. I hear you've joined the team."

"H-hey..." I tried to return the smile. At least it wasn't Brittany here, like in my dream -- but the idea of Olivia watching me fuck, looking at the data, was...well, a bit concerning.

Wait a minute. Fuck who? "So, uh are you...helping me...to generate the control data, Natasha?"

In answer, she turned away from me, unzipped the dress, revealing an expanse of toned back and a lacy black bra. I swallowed, hard.

"That's right. Are you amenable to that?" She looked over her shoulder, into my eyes, biting her lip. I could see Olivia smirking out of the corner of my vision, but couldn't look away from Natasha's body. She had to be ten, maybe fifteen years older than me...but fuck, she was hot.

"Uh...yeah I'm amenable...three minutes just might be...a long..." I trailed off. Both she and Olivia were giggling, and I felt myself blushing.

Natasha ran a hand teasingly down my chest; I could feel her fingertips through the mesh of the harness, and couldn't help an intake of breath. She was just so...sensual.

"Mmm, don't be scared. I'll help you. And you've been working on your stamina with Olivia, haven't you? Surely you can last three minutes...it's not that long a time..."

I gulped. "I'll t---" Natasha leaned in and kissed me on the lips. She was doing something with her tongue that was practiced, dominant. I felt most of me melt, and one very specific part of me stiffen. I moaned, helplessly.

She broke the kiss off and pushed me back onto the massage table. She stepped out of her dress, keeping her heels on. Maintaining eye contact, she slid her panties down her legs. Fuck. She was hot, and it was impossible to meet her gaze -- I just kept staring at her toned body, her tits in that bra, the way her legs looked in those heels...

"Getting really clear data, Natasha. Wow, he's ramping up quick, even for you. He's at like a seven out of ten on most metrics and his pants aren't even off yet." I could hear amusement in Olivia's voice. Yeah, I was really turned on -- rock hard and leaking already. I felt a sense of embarrassment. A seven out of ten? What was I supposed to be at?

"Ignore her..." Natasha murmured, as she stripped off my clothes. "Focus on me...my body..." she settled next to me on top of the massage bench, running her hands over me.

"I can see you like it..." her hand ran down my abdomen, wrapping around the thick base of my erection. "...and I like yours," she whispered. "This is going to be fun."

I moaned.

She moved from my side to expertly straddle me. I could feel her wet heat against the head my cock. She looked me in the eye. "Ready? Three minutes..."

I bit my lip. I was...really turned on. "Okay..." I tried to brace myself.

She placed her hands on my chest for balance, put her heels on either side of my legs, and slowly sank down on my length, letting out a hiss. "Mmm...how do I feel?" Fuck. She was warm, wet. It felt amazing.

"G-guhhh..." As I tried to tell her she felt good, she bounced a few times, almost experimentally, up and down my length, and let out a little moan.

That was it. I felt myself right on the edge.

"Uh, he's at like a 9.6, Natasha..." Olivia warned.

"Thank you, dear," she purred. She lifted herself up so that only the thick head of my cock was inside her. "Let me know when he's back at, say, an even 9.0." She glanced down at me, smiling.

"Those readings are how close I am?" The idea was strange.

"Oh, yes. There are all kinds of data that your body is putting off when you get close to cumming. Neurological activity, nerve stimulation, blood pressure, the works. The harness reads all of it."

"Oh...." I tried to calm myself down. Natasha glanced over at Olivia. Olivia waited another ten or fifteen seconds, watching something on the laptop, and then gave her a thumbs up.

Looking down at me, Natasha bit her lip, and said "Now, then..." and slowly, sensually, impaled herself on my thick length once, pulled up, and did it a second time. Fuck. She just...really knew what she was doing. There was something in how she moved, some trick of her hips, that just made it feel incredible. I felt the orgasm building.

"Um...9.8 now..." Olivia sounded somewhat incredulous.

Natasha giggled. "I don't think you can handle me, Rick."

"Y-you wanted data....because I'm an outlier..." I muttered the words defensively, feeling ashamed. There was something about having numbers put to just how little control I had that made it that much more humiliating.

"Mmm. Just so. Take your time..." she said the words teasingly. She leaned down to whisper in my ear. "Do you think you have so much trouble controlling it because it's just so big?"

I didn't know what to say to that. "I, uh, maybe..."

"Or are you having trouble because of what I'm doing? You really fill me up. It feels...good...thick..." As she spoke, she was doing something -- flexing herself, around me. It felt incredible, almost a milking sensation. I moaned helplessly, feeling myself speeding towards the edge of an orgasm.

"9.9, Natasha..." Olivia just sounded amused, now. 9.9 seemed accurate, a small part of me thought, as the rest of me fought to stave off an orgasm.

Natasha sighed regretfully, pulling up and backing off again. "Mmm, you feel good, but it is frustrating to have to keep stopping...How much data do we have?"

"About ninety seconds worth. Pretty, uh...stop-and-start, though..." Olivia continued to sound amused.

I flushed, feeling that in my ego. "Y-you can go again if you want..."

Olivia laughed. "I wouldn't, he's at a 9.6...ooh, a 9.7, I think he likes my laugh..."

Fuck. This was embarrassing.

Natasha was whispering in my ear again. "I don't think you're going to be able to last for three minutes of data, Rick...I've barely gotten started. Would you like to come back for another session? If you did that, I could make you cum right now; we can get the rest of the data another time."

"Okay..." I could barely form the word. How did I always end up here, desperate to cum?

"Mmm, I thought you might. But..." her lips curved up into a smile. "...say please." she looked at me expectantly.

God dammit. In front of Olivia, too. "C-c'mon, make me cum..."

"Rick..." she pouted. "You can do better than that."

"P...please...make me cum..."

I heard Olivia giggle. I flushed with shame.

"Mmm, good boy..." As she spoke, I could feel her begin to flex around my thick length, that milking sensation, but it kept going. She was silent, keeping eye contact with me, holding her body motionless over mine, as she milked my length.

I was gone. She wasn't even moving up and down, but whatever she was doing, I could feel it send me over the edge.

"Oh, fuck..." I bucked my hips and started cumming. She held a small smile on her face, effortlessly staying atop my bucking hips, riding out my orgasm as I came inside her. Whatever she was doing with her pussy, it was extending my orgasm, drawing it out over a longer period of time. I was panting and out of breath when it subsided.

"Mmm. Very interesting. Thank you, Rick." Natasha carefully dismounted and began cleaning herself up. Olivia turned the laptop to face her.

"Not bad -- over two minutes of data, actually..." Natasha mused, and then winked at me. "We'll have to find another time for you to come in again, soon, though." I nodded wordlessly, spent.

"See you tomorrow, Rick. Maybe we can talk about this during our session." Olivia gave me a cheery little wave, accompanied by a smirking grin, and strolled out of the room.

Why had it needed to be Olivia, of all people?

---

CHAPTER 16

The next day, when I showed up at the massage parlor, Claire was at the front desk. She gave me a little wave.

"Hey...Brittany said she didn't get the job," she whispered.

"Yeah...when I talked with Natasha, she had already decided not to hire her." I continued to be pretty surprised.

"Oh...wow. Well, Brittany is pretty upset about it, but whatever. I'm sorry she, uh, overhead us..." Claire bit her lip nervously. I realized we hadn't really talked about it since I was at her place last week.

"Hey, don't sweat it. She's an asshole, that's not your fault." I smiled encouragingly at Claire. "Want to hang out again this weekend?"

Claire beamed. "Yeah! You should come back over to my place...I'll make it up to you..." She glanced around, making sure we were alone, and lifted up her t-shirt, flashing her tits barely contained by a pink bra.

Her tits looked great -- not that I had needed any encouragement. "Well, you've convinced me. Tomorrow?"

She nodded, lowering her shirt. "Why don't you come over in the evening -- say, 7:00? Brittany usually goes out and I can make us dinner."

"It's a date." I grinned. She grinned. We both grinned.

Olivia, of course, chose this moment to appear. "You guys being gross again? Yeah, I figured. Rick, come on back when you're ready." She smirked and ducked back into the massage room.

I gave a little laugh, shrugged at Claire, and headed back to the room for my massage.

---

Olivia left the room while I disrobed and got under a towel as usual, before returning.

"So, you're investing in Natasha's companies now, huh?" She started working on my shoulders.

"Well, not really investing, but she asked me to advise...mostly I think she just wanted more testing data..." I bit my lip, thinking about Natasha riding me.

Olivia giggled. "Well, from what I could see, you seemed to enjoy participating in the tests..." she continued to work my shoulders and back.

"Uh, yeah..." I flushed, thinking of Olivia watching the test, watching as I blew my load incredibly quickly. "It was...fun, I guess."

"A shame we couldn't get all the control data she needed in a single session..." She lowered her voice to a whisper, leaning in so her lips were close to my ear. "Did Natasha feel good? Did you like being inside her?"

"Yeah, she..." I trailed off. I could see where this was going; she was going to tease me for how little control I had. Y'know, I thought, I didn't have to let this get to me. I tried to be nonchalant about it. "...I mean, yeah, she felt great."

"Aw, you sound a little defensive..." I could hear the smile on her face. "Embarrassed by how easily she had you cumming?"

My face heated. "She...she definitely knows what she's doing, that's for sure." I didn't have to let this get to me, I told myself. I could feel a familiar twinge in my cock that I tried to suppress at her teasing words.

"Mmm, she certainly does. The woman's a genius when it comes to sex products, so it doesn't surprise me that she'd be a genius when it comes to sex, too. I couldn't see what she was doing, obviously, but the readings were...impressive. But...Rick...we both know it wouldn't have mattered whether she was a genius or a virgin...you'd cum fast either way." She was continuing to work my back.

I could see what she was doing, and I once again tried to avoid rising to the bait and getting more embarrassed or defensive. "Maybe; who knows," I said neutrally.

Olivia giggled and leaned over so her voice was right in my ear. "I did really like seeing the harness measuring all your reactions. I wonder what it'd show during one of our massage sessions...." She ran her tongue along my earlobe. My cock lurched.

Fuck. She always seemed to know just what to do. I didn't say anything, trying to avoid responding to her teasing and not getting incredibly turned on.

"You can go ahead and flip over, Rick. Y'know, I was thinking, you've been seeing me a while now..." She paused.

"Yeah..." I acknowledged, guardedly, as I flipped over.

"How come we've never...done it?" She was looking down at me now, a half-smile on her face and curiosity in her voice as she studied me.

"W..what do you mean?" I tried to ask the question neutrally.

But I knew exactly what she meant. She had made me cum many different ways, but we had never had actual penetrative sex. I thought about what it would be like to fuck her all the time. She teased me about it all the time.

"Well...you've fucked Claire, and now Natasha..." she smirked. "Fucked might be a strong word, but anyway, you've been inside them. But you've never been inside me...Am I not your type or something?" she bit her lip, trailing off as if musing.

I wasn't sure how to respond. It's not like I didn't want to. I wanted to fuck her so badly. "Olivia, I--"

"Natasha and Claire are both blondes, and their tits are bigger than mine...maybe that's what you like..." she thoughtfully ran a hand through her long dark hair, cupping her a breast with her other hand.

I looked her up and down. She was in black leggings and a grey tank top today. Toned, athletic, pretty face, tanned skin, dominant, bratty and teasing...

"Uh, n--" I wasn't sure I had a type, but if I did, Olivia certainly more than met the qualifications. She was incredibly hot. But Olivia cut me off again.

"You know, I feel like we used to make bets all the time during our sessions, and we haven't done that in a while," she mused. "This is giving me an idea. What if we made a bet today?"

"Um, okay...what kind of bet are we talking about here?" I flushed, thinking of all the bets I had lost with her. How it never took her long to get me cumming.

She pursed her lips, looking down at me. "Hmm...let's talk about the stakes first." She had a playful grin on. "If I win, you have to take me on a date."

I blinked. Not what I had expected. "Um, what?"

"A date, Rick. We go out together, have a fun time, you probably pay for dinner...I imagine you've heard of them?"

I blinked again, blushing. "Uh, yeah, I know what a date is. I guess I just didn't realize you were...interested...?"

That wasn't exactly what I meant...but I wasn't sure exactly what I meant.

"I don't know if I'm interested," she said, the same playful grin in her voice. "But that's the point. There's only one way to find out."

"Uh, alright. If you win, I take you on a date." This was a confusing turn.

"So what do you want if you win, Rick?" She asked the question softly.

The answer was, as always, easy. "I get to fuck you. From behind." I tried to sound confident instead of desparate. The idea of doing Olivia doggystyle -- teasing, bratty Olivia, who was always dominating me, always making me cum whenever she wanted -- was a complete obsession at this point, even if I knew I wouldn't last long.

Olivia giggled. "Ooh, so specific." She twisted, giving me a profile view of the swell of her ass, flaring out from her tiny waist in her leggings. "You don't think you'd impress me enough on a date to get to do that anyway? You could wine and dine me, and then take me back to your place? Oh...are you worried I don't put out on the first date, Rick? Or maybe you want to fuck me, but I'm not girlfriend material..." She pouted.

Fuck. My face reddened, whatever thoughts I'd had about not reacting gone out the window. "No, I..." I trailed off, flustered -- and getting hard -- as she started giggling.

"Mmm, I hope I win. A date would be so fun," she purred.

I tried to regain some semblance of equilibrium; even for a session with Olivia, this hadn't been how I had expected this to go. "So what's the bet?"

"Well, I was thinking how we've done so much work on your stamina..." she trailed off as if considering. "...you haven't improved that much, but maybe you're ready to give it a shot..."

Ignore the comment about your lack of improvement, I told myself.

"Olivia, give what a shot?"

She leaned over next me to whisper in my ear. "Here's the deal. We get you nice and hard. We get me nice and wet. I climb on top of you and take you inside me, but holding still. And then I start masturbating, Rick. With your big dick inside me. And we see who cums first. Whoever cums, loses the bet; if I cum with you in me, you get to fuck me from behind. If you blow your load, you take me on a date. How's that sound?"

My heart had started pounding. "Y-yeah..." I was so turned on. I couldn't process whether I was likely to win this. I doubted it. But the idea of finally getting inside her was intoxicating all on its own. I had to say yes.

She smiled. "Good. It's a bet, then. Now..." she reached under the towel and wrapped one hand around my shaft. I let out a gasp at her touch. "Mmm, looking forward to this, huh big guy? Already so hard..."

She pulled the towel away, and then as I watched, she stripped off her leggings and panties. Climbing on top of me, she whispered, "Give me one second...I know you're ready to go, and it's pretty hot how turned on you are, I just need a little more...ah...to be ready to take...mmm...that monster..."

I watched as she stuck two fingers in her mouth and sucked on them, making eye contact with me, before sliding that hand down between her thighs. She eyed my cock and bit her lip.

I tried to calm myself down, watching her. I could feel my cock twitch; I had spent so much time thinking about this -- what she'd sound like when I slid into her, how she'd feel, what she'd say -- that I was worried I'd lose immediately.

I tried to focus. I wanted to win, if I could. What would help do that? She was always painting pictures in my mind, maybe I could do the same thing... "Are you thinking about what my big dick is gonna feel like?" In my head, it had some bravado, but it came out more whispered than I would've liked.

"Mmm...I'm thinking about how hot it is that you just can't handle me...I'm wondering whether you'll cum just from me sliding your thick shaft inside me..." I twitched again as she watched. Precum was starting to drip down the head. "Fuck, you’re so turned on I could make you pop right now. I guess that's not the bet, though, huh..."

Slowly, she reached out for my cock, pausing before she touched it. "I'm not trying to make you cum, I just need to lubricate you a bit..." I mentally braced myself, and she gave me a quick stroke, spreading precum over the head and down part of the shaft. Her hand felt exquisite. "Mmm, that should work."

She grinned. "Now, you just have to last through one downward stroke to get all the way inside me, Rick. I'll go slow. Ready?"

I wasn't sure, but I nodded anyway.

Biting her lip, staring at me the whole time, she rubbed the head of my cock up and down against her wet pussy. I tried to calm down, to think about anything else besides that I was finally getting to fuck her. It wasn't working -- I could feel her slick, tight opening, heard her let out a low sound in the back of her throat as she started to push down onto my thick head, felt her parting around me, felt the orgasm building --

"O-olivia, wait..." I could hear the desperation in my own voice, and she paused, listening to me, for once. I held incredibly still, right on the edge, trying not to cum, trying to actually get to participate in the bet, acutely aware of how embarrassing this was...

I tried to get myself together. She was silent, just watching me, expressionless, for twenty or thirty seconds. Finally, I nodded.

She giggled, which made my cock twitch; she made an mmm as she felt me move inside her. "I didn't think you were going to be able to control yourself. I'm kind of impressed. Let me know if you need me to stop again..."

She resumed working me inside her. She let out a little moan as she got the next few inches in, followed by a, "Fuck, you're thick..." She was moving slowly, watching my face intently.

She had about three-quarters of my cock inside her when I felt myself approaching the edge again. "W-wait..."

She giggled, but then composed herself, and silently watched me again. After another thirty second break, I nodded.

"Mmm...this is out of character for me, but I'm not teasing you too much...I'm trying to be a good girl for you..." As she said it, she sank herself down, bottoming my thick length out inside her, and moaned. I was immediately back on the edge again, but she held motionless, and I felt the orgasm recede.

Fuck. I had almost cum three times and we hadn't even started the bet yet. Not a good sign if I wanted to fuck her.

"Mmm, you really are big, Rick. You feel great. I'm not sure I've ever felt this full...this is gonna be fun. Let me know when you want me to start touching myself. I'm trying to give you a fair chance..." She smirked down at me.

She was so tight, and I could feel myself throbbing at her words. I gave it a little time, but I didn't think I was going to calm down either way. Looking up at her -- eyes glittering in the dim light, small smile on her face, my thick cock buried inside her, the feel of her toned thighs against mine -- I knew I might eventually cum, even just holding still like this. I took a few deep breaths, and said "Okay, let's do this."

She reached down, rubbing herself, and moaned. "You know, I mostly like to get off with something thrusting into me...or riding something...but this feels really good...so full, and touching myself knowing you're watching and barely holding back...the way you're staring at me..." She let out a little gasp, and I could feel her getting wetter around me. Fuck, it was so hot to hear her getting off on my dick.

"How do I feel, Rick..." she trailed off and moaned, staring down at me, mouth open, moving the heel of her palm of her hand against her clit.

"Y-you feel amazing..." I was breathing hard, trying to ignore the rocking sensation the motion of her hand was causing. She wasn't moving her body on me, but the slight sense of movement was incredible. It made it all too easy to imagine what it would feel like to put my hands on her hips and just start driving my whole length up and down inside her; I would probably cum in a single thrust. I could feel my orgasm approaching.

"Ah oh yeah?" Her breath was short now, ragged as she worked her clit. "You like this? Better than Natasha? Better than Claire?" She smirked at me. "I know you've been thinking about this for a while..."

"Fuck, y-yes...you feel incredible...so fucking hot..." I felt a little guilty; I wasn't sure whether I was agreeing that I had been thinking about it a while, saying yes to liking it, or that she felt better than Claire, or all three. But I wasn't in control of what I was saying anymore; every ounce of my focus and willpower was going towards keeping from cumming, making this last as long as possible.

I was staring at her hand, now, as she continued to grind the heel of her palm into her clit, the rocking sensation driving me ever-closer towards cumming. My cock twitched.

"Mmm, I can feel you moving..." she purred. "You're getting close..."

"I was just thinking.." she was looking me in the eyes, her face flushed. "After all these weeks...I bet you'd really like it...if I came before you...wouldn't you?"

That idea was so hot. The words went straight from my ears directly to my balls. I could feel myself crossing the point of no return. I tried to hold back. "Y-yeah..." I muttered distractedly.

"You'd love to turn the tables on me...make me lose control for a change, with this big dick filling me up...that would be so hot for you, wouldn't it...win the bet and get to fuck me from behind..." She was leaning forward, lying on top of me now, so she could whisper in my ear; I could feel her hand trapped between us, moving quickly, frantically working her clit as she spoke.

I couldn't respond. Every muscle in my body was clenched, every fiber of my being trying to stave off a massive orgasm.

"...Fuck...but that's not gonna happen...I can outlast that quick-cumming dick...gonna make you bust..." she was breathless, barely forming words, and sounded like she was getting increasingly close to cumming.

I probably only needed to last a bit longer, I thought. But that was out of the question. The way she was talking was so hot. I couldn't hold on any longer. "Fuck, Olivia, I can’t, you're gonna make me---"

I started involuntarily thrusting up into her, losing control. I could feel her, slick and tight around me, with each throb of my thick cock as I pumped in and out of her. Stars exploded behind my eyes and I could feel each individual contraction, every rope of cum spraying into her.

A few moments after I began to orgasm, she gasped, and said "Oh, fuck yeah, you can't handle me, y-your big dick is cumming--" and her words abruptly dissolved into a moan as well. Her legs were shaking uncontrollably; the sensation of her clenching as she orgasmed around me was incredible. I wrapped my arms around her, thrusting into her with abandon as she collapsed on top of me.

We both rode out our orgasms, and the room was silent, the two of us still and panting. After a few moments, she slowly pushed herself up so that she was looking down at me. There was a small smile on her face.

I smiled up at her.

"So...you owe me that date," she said, grinning.

"B...but you came!" I was dazed, but somewhat taken aback.

"You came first, Rick."

"But...we both came...I think it's a draw..." I tried to reason.

"Oh...ah..." As she spoke, she slid herself off of me and began cleaning up. "Hmm, well...I guess that means we both lost. So no date, and no fucking..." she grinned. "Unless you want to say we both won, and do both."

I could barely string together sentences, but I didn't need to. "Both," I agreed.

She smirked. "I thought you might. How about tomorrow night?"

Tomorrow night was...Saturday. Claire.

My face must have fallen, because she kept talking. "You already have plans, huh?" She glanced up at the clock. "Well, it's not even 6:30 now, since you still aren't using the whole time slot...what about tonight? I could meet up for dinner around 8?"

"Uh...sure..." My brain was operating a few seconds behind.

"Cool. Text me the place and what the dress code is. See you at 8 or so!" She gave a cheery wave and walked out.

I sighed, cleaned myself up, and left to get ready. Fortunately, I didn't see Claire on the way out. I was probably in trouble, I thought. It was one thing to be doing massage sessions with Olivia while I dated Claire; it was another to be going in dates with both of them. I felt guilty.

---

CHAPTER 17

I got home and showered, and I realized that I definitely had a problem.

There was part of me, I think, that had been hoping my obsession with Olivia would at least wane a little bit, in the wake of finally getting to fuck her.

But, if anything, it had only gotten more pronounced.

I couldn't stop thinking about how she felt orgasming around me, the smooth sensation of thrusting into her, the way she looked down at me, that knowing smirk on her face, how she sounded while she was rubbing herself...

Glumly, I looked down at my cock -- now hard, as a result of this line of thinking -- as I toweled off. And now I was going on a date with her tonight, and a date with Claire tomorrow night. I liked them both, but...this didn't feel fair to them. I needed to make a decision.

Sighing, I got dressed. I was meeting Olivia at a nice sushi place I liked in half an hour, and I needed to get my shit together.

---

Olivia met me outside the restaurant. She was wearing a little black dress and pumps. It was both tight, and backless -- showing off tanned skin, ample cleavage, and toned legs. She looked incredible. I was staring, and I knew it.

"I love sushi. Great choice." She smiled at me and took my arm as she walked up. "Rick, your mouth is open," she whispered, grinning. I shut it.

We had a great meal, and I learned more about Olivia in an hour than I had in the weeks I'd been seeing her. She was a year or two younger than me, had a psychology degree and had expected to go into counseling or therapy, but she had listened to a guest lecture from Natasha, thought she was brilliant, and went to work for her instead -- the pay was better and the work more interesting. I told her about my job, about tennis, and so on. She was smart, and funny, and...well, likeable.

It was the most non-sexual conversation I'd ever had with her. We were settling into some post-dinner drinks when that changed.

"So...how do you feel?" she grinned.

"What do you mean?"

"Well, I don't know if you remember this, but in our first appointment, I said if you could last two minutes through a hand job," she said softly, "that I'd go on a date with you. You, uh, didn't...and haven't...but here we are. On a date." She winked. "That was nine weeks ago. I looked back at my calendar."

I blushed. "Uh, yeah..." I wasn't sure what to say to that.

"Emma had just dumped you, remember?" She took a sip, looking at me over the edge of her wine glass.

"Yeah..." I hadn't thought about Emma in a long time. "That feels like it was about ten years ago, if I'm being honest."

Olivia giggled. "Had other things on your mind? Or other people?" She traced a hand down from her collarbone to the swell of her breasts. I followed her fingers with my eyes, my mouth suddenly dry.

I was feeling a sense of whiplash. Olivia was...well, the terms of our arrangement had felt like they were confined to the massage parlor. But here I was in a sushi restaurant, feeling a familiar rush.

"Olivia...what...what are we doing here?" I blurted the words out, and then lowered my voice as I realized other people had turned to look at us. "It...it's one thing for us to do these...uh, appointments. They feel like somewhere in between sex work and friends with benefits....this is something else."

She pouted. "Aw, you don't like me?"

"No, that's not what I'm saying, I---" but I blushed as she waved me to silence with a smile.

"Rick, I'm just giving you a hard time. I know what you're saying. I've been thinking about it since our last talk. Look, as you may have noticed, I know what I want....most of the time....and I know how to get it. But what's happened between you and me wasn't something I planned."

She stared at me, smirking, and lowered her voice. "It's not like you walked in for your first appointment and I was planning to make you blow your load quick. It's just been spontaneous fun. That's what's made it so engaging. I can see you like it, and I like it, and I like you. I like how easy you are to tease..." She licked her lips, "...in every sense of the word. So, yeah, I'm interested in seeing whether there's something more here. If you don't want to see if there's something more here, well, I'll be disappointed, but I'll understand. If you are...well, we'll figure it out together, just like this."

I mulled this over, considering. I still felt guilty.

She laughed. "Okay, l know what you're really raising. Have you told Claire you're not dating other people?"

My face reddened. "N-no...but I haven't told her I am seeing other people..."

"I thought that might be it. So why don't you just tell her?"

I bit my lip. "What...what if she's pissed?"

She leaned forward, lowering her voice. "Rick, she knows we're doing all kinds of stuff in those sessions. Before you went on a date with her I explained to her that our sessions had generally ended with you cumming for me. She masturbated in front of us. If she's upset that we are getting dinner together, there's some real willful ignorance there."

"But I'll tell you what. If she stops seeing you or something, and you're really down about it, I'll just have to think of a way to cheer you up. I mean, I cheered you up after your breakup with Emma, right?" She giggled.

I supposed that she had. I was trying not to imagine how she might cheer me up. I realized I was getting hard.

"I bet she won't stop seeing you, though. If anything, I bet she'll feel a little like she's gotta lock it down. Your problem is gonna be trying to keep her from jumping your bones. I think she finds me both intimidating and, let's say, inspiring. No idea why." Olivia winked at me.

I laughed, shaking my head. "Jesus, Olivia."

She blinked innocently. "What?"

"Never mind. So...what would you like to do now?"

"Mmm..." her eyes sparkled. "You know, I'm remembering now...we both won the last bet, didn't we? So we still have the other...side...of the bet to fulfill?"

I had actually been actively trying not to think about it for the entire meal. "Yeah..." My mouth was dry again.

"Do you think you can handle it? I know you've been thinking about it for a long time," she teased.

"Yeah, I--" I was rock hard now.

She cut me off. "I have a little game in mind that I thought would be fun to play. Why don't you pay for the check and come to the bathrooms. Knock three times on the family restroom door so I know it's you." She stood up, putting something on the table, and walked away.

It was a black, lacy pair of panties. I stared, blushing, and then grabbed them and tucked them into my pocket before looking around to Fuck. I stared at them for a moment before pulling them off the table and tucking them into my pocket.

---

The two minutes it took to flag down the waiter and pay our tab were the longest of my life, but at least gave time for my erection to subside. I knocked on the bathroom door, and Olivia opened it, grinning, and pulled me inside, locking it behind me. It was actually a spacious bathroom, but she was standing very close to me, looking up at me. She bit her lip. "You gonna show me what that big dick can do?"

I swallowed, hard, and nodded. "Y...you mentioned a game?"

"Yeah. I'm realizing that maybe I've been making the bets in our massage appointments too...hard...for you." As she spoke, she stepped back from me, turning away and unzipping her dress, revealing her smooth, tanned back. I stared.

She looked over her shoulder at me, making eye contact. "But I do want you to try to last longer for me...and our last appointment got me thinking." She grinned, as she stepped out of her dress, naked except for her pumps. She was still facing away from me as she tossed her dress over the edge of the sink. I could see the swell of her ass in front of me, and her tanned tits in the reflection of the mirror. I was rock hard again.

She continued. "You seemed to like the idea of me cumming before you...of getting the chance to dominate me for a change. So here's the deal. You fuck me from behind, like we agreed. For every thrust you get in me, I'll give you ten seconds of time in our next appointment where I'm such a good girl for you." She looked up at me through lidded eyes. "No teasing, no humiliating..." she bit her lip, staring at the bulge in my pants. "Just me, and that big dick, doing whatever you want. I think you'd like it a lot."

My cock lurched. There was something in the tone she said the words with that implied -- I didn't know exactly what, but some combination of subservience, my pleasure, letting me use her, whatever. I could feel myself leaking precum in my boxers. Fuck, that was a hot idea.

She grinned. "So I'm sure you'll last a nice long time, right big guy? Really pump me with that cock...and then use me next session..." She bent over the sink, and wiggled her ass at me. "Fuck, I can't wait to see how long you can actually last with those stakes. I'm ready when you are." She looked over her shoulder at me.

I've never stripped down my pants and boxers so fast in my life. My cock sprang out and I stepped up behind her. I was so fucking turned on. I took a second to try to calm myself down a bit. I wanted to last before, but with these stakes...I thought about all the things I could tell her to do -- a sloppy blowjob...maybe riding me like I'd seen her ride a dildo...Hell, maybe just not talking so much shit about how fast I came. Setting the rules for a change would be nice.

My cock twitched. This wasn't helping to calm me down. She smiled at me knowingly. "Mmm, thinking about what you'll have me do already? I'd focus on this, big guy..." she rolled her hips back, just barely brushing me with her ass. "I'm ready for you. I spent the whole time you were paying the check thinking about how fucking hot it's going to be to see how long you can last. Ten seconds per thrust. I'll count for you."

I flushed. This talk wasn't going to help me last longer. I slowly pressed the head of my cock against her entrance. She was right -- she was wet, ready for me. I heard her make a small gasp as I grabbed her ass, pushing my thick head inside her. She moved a little, adjusting the angle, and I began to slide in.

I could feel the orgasm building already, the sensation of her slowly pushing back as I pushed in, the feel of her ass under my hands... She gasped, as more and more of me slid inside her.

I pushed the rest of my length into her, feeling her ass against my hips and thighs as I bottomed out.

She moaned. "Oh, fuck yeah. I want you to pound my pussy as hard as you want, Rick. Don't hold back."

I froze. I was finally doing it -- she was bent over in front of me, her ass in my hands, my thick cock buried all the way in her. I wanted to really rail her too. But I was grappling with the familiar sensation of a mounting orgasm.

"I'll count thrusts for you..." the words came out with a moan. "That was one..."

My face flushed. Shit. I had to get more than one thrust. Slowly, almost tentatively, I pumped my cock in and out of her again, and paused.

"Two..." I could see the knowing smile on her face in the mirror.

That fucking smirk got to me. It always did. I felt myself right on the edge.

"What's the longest you ever lasted with Emma, Rick? Like, five pumps?" she teased.

I could see my face was bright red in the mirror. The humiliation only made it harder to get myself back under control.

She didn't wait for me to answer. "You said she had a nice ass, right? But you like mine too?" She put on a mock frown, and I felt her roll her hips under my hands, pushing her ass against me. I moaned.

"I'll take that as a yes...think you can give me five before you cum?" she giggled. "I mean, I helped you get over Emma...I think it's the least you could do...or do I feel that much better than her? Maybe you just can't handle me..."

I took a few deep breaths, trying to get myself under control.

"Did Emma let you spank her while you fucked her from behind, Rick?"

"I-I mean..." I hesitated. I had tried it, a few times, but it hadn't been Emma's favorite thing. Talking about that with Olivia felt wrong, though.

"Mmm, she was kind of demure, wasn't she?" She had a wicked grin on her face. "I want you to spank me and fuck me."

"I...I need a second..." As embarrassed as I was to admit it, none of this talk was helping to bring me down from the edge of an orgasm.

She giggled. "Aw, c'mon, Rick. A real man would slap my ass and fuck me with an invitation like that. You're a real man, right?"

Fuck. I let out a helpless, frustrated, ashamed growl, and grabbed her ass more tightly. I slapped her, hard, which elicited a satisfying ah from her. And then I gave her a quick, fast pump, working my length in and out of her.

"Mmm...three..." she purred the word out.

I gave her another spank, and another pump.

"Ah...four..." it was a moan this time, but a knowing one.

And that was it. Moaning myself, I pulled out, and pumped my cock furiously, spraying cum all over her ass and back. She giggled delightedly.

"Mmm. That was a big load for only four pumps, Rick. Maybe we can beat your record with Emma another time; it'd be a shame if all our work on your stamina hadn't improved things." She leaned over, grabbing some paper towels and wiping herself off. "But maybe I'm just hotter than her." She winked at me.

I was breathing heavily still...and still feeling the sting of humiliation. "Fuck, Olivia..."

She grinned. "You certainly seemed to enjoy it...even if it didn't last that long."

We both cleaned up and dressed. I left the bathroom first; Olivia waited and left a minute or two later.

She smiled at me as she left the restaurant. "Well, I enjoyed that date."

"You know, me too." I really had.

She stepped forward, arching up, and kissed me, thoroughly. Fuck, she knew how to use her tongue. My cock lurched.

She smiled again, but her knowing smile, this time. "Mmm, maybe that gives you some ideas for your forty seconds...although I'm not sure you'll even need all of them." She licked her lips.

Fuck. I blushed. "Uh, yeah, I'll be thinking about...that..."

"Good." She seemed satisfied. "I'll be thinking about what's going to happen during the rest of our appointment. You seemed to like it when I told you a real man would just fuck me," she mused.

I had no response for that.

"Anyway, don't have too much fun tomorrow night...or if you do, at least tell me about it. See you next week, Rick."

I watched her go. Now I just had to think about what the fuck to say to Claire tomorrow.

---

CHAPTER 18

I showed up at Claire's apartment at 7. I had brought flowers and a bottle of wine. I was nervous about the conversation I needed to have telling her Olivia and I were...dating? Well, had gone on one date, anyway. A date I had enjoyed immensely.

I took a deep breath and knocked on the door.

Claire was wearing...a little black dress. It was tight, backless, and showed off her tits incredibly well.

It was, I realized, the same dress Olivia had been wearing last night. I was completely thrown by that realization. Had they planned this? Was it just coincidence?

She clearly noticed me staring. She grinned. "Like it?" She gave a little twirl.

"Y-yeah...you look fucking great..." I knew I was blushing. I did my best not to mentally compare how it looked on her and Olivia. They filled it out very...differently...stop, I told myself. I couldn't ask -- what if they hadn't planned it? It wasn't how I wanted to introduce the idea that I was dating Olivia too.

I handed her the flowers. She turned pink.

"Aw, thanks Rick. Come on in. Dinner is almost ready. Brittany left like half an hour ago and probably won't be back until late, thank God..."

Claire had made an excellent risotto; we talked for an hour or two while we ate, our conversation meandering. We had finished a bottle of wine each and were both well on our way to being drunk.

Claire especially -- she wasn't that big a lady. "So how have the appointments with Olivia been?" she giggled.

"Uh, good, I've actually been meaning to---" I tried to charge into it, but she cut me off again.

"I liked the one I got to watch...she really worked you over..." she was blushing and biting her lip.

"Y-yeah? She, uh...yeah, I guess she did..." I wasn't sure how to re-rail this conversational train.

"Yeah, it was pretty hot. You've had another appointment since then, right? What'd you guys do this time?" She looked curious.

"She, uh...she challenged me to a bet..." Well, back on track, but this wasn't exactly how I had hoped to introduce the topic.

"Ooh...what kind of bet?" Claire leaned forward. Her cleavage was utterly captivating. I couldn't look anywhere else.

"She, uh, took me inside her...and wanted to see who came first..." Now I was blushing. And I was starting to get hard again.

Claire gave a sharp intake of breath. "Mmm." She took another sip of wine. "Actually, I think I want you to tell me about this in the bedroom, Rick." She stood up, a little unsteadily, and headed towards her room.

I followed her. She lay down on the bed, setting her wine glass down on her bedside table. I lay down next to her. She nestled up against me. "You were saying?" "She, uh...she...got on top of me and started...rubbing herself...with me inside her..." as I was talking, Claire started tracing the outline of my cock in my pants. It was getting me harder and harder.

"Mmm...so who won?" Claire sounded a little breathless.

"S...she made me cum first, but only by a little bit..." I was incredibly turned on now.

"Ooh. So she won? What was the bet about?" Claire was definitely getting off on this.

"Uh...if I won I wanted to fuck her from behind...and if she won...she wanted me to take her on a date." Well, this was not how I had imagined delivering that news.

Her hand stopped moving around my cock.

"So...she won...so you took her on a date?" Her voice was small.

"Uh...well we actually kind of called it a tie...so...we both won. But yeah, I took her on a date."

"So...you took her on a date and fucked her on the date?" Her tone hadn't changed. I looked down at her, but she wasn't making eye contact -- she was staring off into the middle distance.

"Uh...I mean, yeah...Claire, I --" but she held up a hand.

"Did you take her on the date just because of the bet, or do you actually want to date her?"

This was a very good question. "Claire, I don't know. I'm trying to figure that out myself."

"Well did you have fun on the date? Are you going to take her on another one?"

"I...I don't know, Claire. This isn't really how I wanted to tell youm but I was going to tell you. We haven't talked about being exclusive but I thought you should know anyhow."

I reached out and put my arm around her. She didn't shy away, but she didn't exactly lean into it either.

"Rick, it's just kind of hard to imagine that someone could be into both of us. We're...pretty different, you know? I mean, don't get me wrong, she's hot, I get it. I guess I just figured the massage appointments were like...you doing some specific sexual stuff with her, not that that's what you wanted a relationship to be like..." She was still not making eye contact.

I sighed. "Look, I didn't even plan for the massage appointments to be the way they are. Initially, I just went after my breakup with Emma, and Olivia just...escalated things...you've seen how she is..." I shrugged helplessly.

"Mmm, yeah, but you must like it. You've kept coming back; I mean, you could've just not showed up again after that first appointment. And you took her on a date...and it wasn't just because of the bet, or you would've said that..." she did look up at me now, eyeing me. "I think you like how she is."

"Claire, c'mon..." This wasn't how I had wanted this conversation to go.

"She's not the only one who can be teasing and dominant, you know." There was something different in her expression now.

"No, I know that, I...wait, what?” I trailed off, actually registering what she was saying.

"You know, I've been letting you take the lead. And I've liked that. You've got a nice big dick and it's fun to let you have your way with me..." She sat up and then leaned over me. Her tits were inches from my face.

"But maybe that's not what you want. I used to be a bit of a mean girl in high school, you know? Cheerleading culture...I've always felt bad about it...I was kind of a bully..." I could see her visibly psych herself up, and she made eye contact with me, her voice taking on a different shape -- a little ditzy, full of false sweetness. "But, like, a quick cummer like you probably needs to be put in his place, right? I get it."

My cock didn't just twitch, it flexed. Fuck. "Claire, I--"

She put a finger on my lips. "Nuh uh, Rick. I think this is what you like. I've wanted to get off with that big dick in me since I first saw it. But I haven't gotten to. And now I find out Olivia came all over it? Olivia, who spends all her time talking about what a quick cummer you are? I guess I've just been approaching it all wrong."

Her hand slid back down to my cock, gripping it at the base of the shaft, still with that bratty, almost valley-girl cadence to her voice. "God, you're such a big guy. Your cock is totally huge. But I think you get weak when women talk about you cumming fast, don't you?"

I moaned at the feel of her hand on my cock through my pants...and maybe at her words. God, this was embarrassing.

She pursed her lips as if pondering something. "Although, like, you've always cum so fast for me, even without teasing. Oh my god, how fast are you gonna cum if I'm actually teasing you..." She giggled, a syrupy sound.

She started unbuttoning my pants. "You know that guy I was dating before you? The one with the totally tiny dick?"

I nodded helplessly. She pulled my pants and boxers down, and my thick cock sprang out.

"God, look at this thing. He was so much smaller than you are. But you know, Olivia made you cum a lot faster in that appointment than he usually came for me...and it made me wonder...like, if I teased you, you might cum even faster than he did..."

As she spoke, she pulled her dress off. I gaped, mouth open -- she was wearing a matching set of red bra and panties. As I stared, she stripped off her panties, and climbed on top of me -- I could feel her wet pussy against the head of my cock.

I realized, embarrassed, that Claire was probably right. I was going to cum really fast if she kept doing this. I tried to get myself under control.

There must've been something in the expression on my face, because she laughed. A mocking sound -- the kind of laugh a popular girl might make while rejecting the nerd who wanted to take her to prom. "Oh yeah, I can tell, you're gonna bust even faster than that loser with the tiny cock. I thought you were like, older and experienced...what's the problem?"

She slowly sank onto me. She was tight, but wet around me, and I slid in...well, not easily, but more easily than I had been. I moaned. I could feel the orgasm already incredibly close.

She sighed. "God, your big dick feels amazing. But it's not gonna last, is it?" She giggled. "Hold still and try to hang on, stud," she said, sarcastically. "I want to tell you a story."

She leaned forward, whispering in my ear. "This all reminds me of another guy I fucked. I only lost my virginity last year, you know. There was a senior on the football team who was in one of my freshman classes -- tall, jacked, hot. Dumb as a bag of rocks, but I didn't care, I didn't want to talk to him. I could tell he had been with a lot of girls, and he talked a big game about how he'd, like, totally rock my world."

"I figured that was a good way to lose it -- he was older than me, experienced, like you, so I was sure he'd show me a good time." She rolled her eyes. "Well, we were in his dorm room, and I got my bra off and he looked like, stunned, you know? But guys have always reacted that way to my tits, so I figured, no big deal..." she smirked.

I was speechless, staring at her tits as she spoke, knowing where this story was heading but transfixed anyway.

"Boy was I wrong. I got on top of him, just like this..." She wriggled on me, gasping a little as my length shifted inside her, and I moaned, feeling my orgasm continue to build as I watched her tits shimmy with her movements. "Well, he was staring at my tits...yeah, just like you are, that's right..."

Claire bit her lip. "And my tits have always been sensitive, you know? I like it when guys play with them. I was hoping he'd squeeze them, maybe suck on them...so I pushed them into his face...and he came, like, instantly." She laughed. "Just, like, couldn't handle it. He was super embarrassed about it..."

I was trying to hold back -- but she was so tight around me, and the way she was talking...

"He kept trying to say how that never happens to him, just to wait a few minutes...but I thought it was so funny, I couldn't stop giggling, so I left." She looked at me, expectantly. "I mean, that wouldn't happen to you though, right? You're like, so much more experienced than me...there's no way you'd cum that fast...you can totally last if I shove my big tits in your face...you won't blow your load like some college boy..."

"Claire, I...wait..." I was feeling humiliated, and on the brink of cumming.

"Oh? Yeah? Do you really want me to wait, though? Or do you want me to make you cum quick with my tits in your face?"

I couldn't respond.

"Look, let's just, like, test it. A little experiment...I'll shove my tits in your face...and we'll see what happens," she giggled. "I mean, a real man wouldn't cum just from that."

Those words -- the same way Olivia had said them last night -- were too much. She didn't even get the chance to move. I couldn't hold on any longer. Moaning, I grabbed her tits and started thrusting into her.

She gasped and started moaning as well. "Oh my god, you're cumming, your big dick can't handle me..."

I could feel my cock pulsing, spraying my load into her. "Fuck, Claire..."

She started bouncing down to meet my thrusts. "Yeah, that's it, cum quick for me..."

It was a drawn-out, intense orgasm, and an enormous amount of cum, especially given the (for me, significant) quantity of sex I had been having recently. She collapsed on top of me.

"Fuck, Rick...that was...intense." She was breathing heavily.

"I...yeah..." I felt a little tentative, but like I had to say it. "Claire, that was intense. But you don't need to be Olivia. I like you the way you are."

Her voice was small again. "I...I know. And I like how we've been doing it. I just wanted to make sure you knew we could play, too, if you wanted to. I can be fun..."

I stroked her hair. "I know you can be fun. You have been fun. You are fun."

"Will you...stay the night?" She asked hesitantly.

"Sure." I continued stroking her hair, gradually feeling her grow still beside me, her breathing even, and then drifted off to sleep myself.

---

I woke up needing to piss really badly. I drowsily glanced at the clock on her bedside table -- 2AM. I gently extricated myself from her arms -- she didn't even stir -- and threw on my boxers, walking down the hallway to her shared bathroom.

I was just shaking things dry, when I heard the front door of the apartment open, followed by the sound of someone moving around the living room. Shit. I froze. Brittany.

"Claire? You up?" Claire didn't answer; given how hard she'd passed out, I doubted she was waking up any time soon. I heard Brittany settle in on the couch. Well, fuck. I thought about the layout of their apartment. To get back to Claire's room I had to walk down a hallway, past an opening into their living room, past Brittany's room, and then go into Claire's room. The couch was facing away from the hallway...and most of the lights were off...it might be doable.

I turned off the bathroom light, quietly opened the door, and crept down the hallway right up to the edge of where the living room was, listening for sounds of the couch moving the whole time. Ideally, I would get out of the hallway and into Claire's room before Brittany decided she needed to go to bed or use the bathroom; I really didn't want a confrontation with Brittany given how shitty she had been, and how delicate things seemed with Claire.

I couldn't hear Brittany moving at all, but I could hear her muttering, talking to herself. She sounded wasted, which made sense -- from what I recalled from the times Emma hung out with her, Brittany had liked to go pretty hard on the weekends. I crept as close as I could without coming into view, to try to hear what she was saying.

"Guh...can't believe she didn't even go out on a Saturday...she's kind of a loser..." God, Brittany was such a bitch, I thought.

"Though...maybe she's all worn out from taking that big cock..." Brittany giggled, a bit drunkenly. That sentence brought me lurching fully awake. Fuck. She was talking about me.

She kept talking to herself, and I heard her shifting on the couch. I risked a glance. I could see her, facing mostly away from me, but I was probably visible out the corner of her eye. She was wearing clubbing or rave attire -- full makeup, and a black mesh top with a bright green bra visible underneath. Her pale skin almost glowed in the moonlight. She was undeniably hot.

As she spoke, she reached up and caressed one of her breasts. "Emma always said he was way bigger than anyone else she'd been with..." Brittany mused. I wasn't gonna lie, this was inflating my ego...and my cock. But I had to get out of here. This was not a good situation. But I couldn't risk just darting across the opening and getting further down the hallway. I was trapped.

"Couldn't last for Emma though..." she giggled again to herself. "And she is kind of a prude...If he couldn't last for her he definitely couldn't last for anybody else..."

My face burned. She really sucked.

"I bet I could train him..." there were the sounds of movement, but not like she was getting up...a rhythmic, repetitive motion. "I'd get that big dick to last..."

Fuck. She was masturbating, thinking about me.

I was rock hard now, and torn. Did I leave or keep listening? It felt wrong to stay, but...

She kept talking, her words slurring a little bit. "Make him practice with me..." She moaned, the repetitive motions continuing.

I risked another glance out into the living room. She was angled away from me, but only just, the upper half of her body visible. She was obviously riding something, grinding into it -- maybe one of the couch pillows.

"Just keep taking him to the edge...then stopping...fuck, he'd look so desperate..." She was moaning as she spoke, and I couldn't really see if her eyes were open in the dim light with her not facing me directly. I was both terrified and turned on. I wasn't sure what to do. Just sprint across the hallway quick, and hope she didn't see me out of the corner of her eye? It felt too risky.

"Mmm, that's right Rick, you don't cum until I say..." My name out of her mouth, moaned, made my cock lurch, dribbling out more precum into my boxers. It was tempting to rub one out watching her pleasure herself.

"You have to last...be a good boy for me..." I was aware that if she spotted me now -- precum staining my boxers, massive hardon -- there would be no salvaging this situation. Did I care?

"If you do...I'll let you fuck me nice and hard with that big dick...use my hot body...I’ve seen how you stare…” she was gasping now as she talked to herself. Fuck. I couldn't keep resisting. I started fondling myself, half-stroking as I looked around the corner at Brittany grinding against a pillow. In the dim light I could see her pick up the pace, her mouth parted sensually, breathing hard.

"Yeah...that's it...no, don't cum yet...just hold on a bit longer...I knew you could do it...you're gonna make me cum Rick..." God, listening to her was hot; she was such a bitch, but she was thinking about me while she got herself off. I had already cum once tonight and that was the only thing keeping me from blowing my load right now. As it was, I was leaking all over, my boxers sticky, and I was having to actively stroke more slowly to keep from blowing my load in the hallway.

"Mmm, you're following directions so well...after I cum, I want you to...pull it out and cum all over my face..." Brittany was barely forming words now, clearly working towards a climax. I could feel my own cock twitching. I imagined cumming all over her pretty face. I needed to not cum in this hallway, to get back into Claire's room. I tried to hold back.

"Fuck...you've been such a good boy...okay...I'm...c-cumming...yeah, fucking spray it all over me, fuck, Rick..." Brittany was moaning, her back arched, eyes...almost certainly closed. I was right on the edge of cumming -- but gritting my teeth, I held back, and took the opportunity and ducked across the hallway, opening and closing Claire's door as quietly as I could.

My heart was pounding. It was quiet in the room; I couldn't really hear Brittany in the living room at all. I took a few deep, steadying breaths and then climbed back into bed next to Claire, spooning her. She let out a little moan, and pushed her ass back against my erection. Shit. I realized I was still rock hard, and pretty close to cumming.

"Mmm...having good dreams?" she sounded sleepy and still a little drunk.

"Y-yeah..." I was still distracted, half-worried Brittany was going to open the door and ask what the fuck I was doing.

She reached around to fondle my length. "Mmm, you're so big..." she said sleepily. "Give it to me."

"I...I'm pretty turned on, uh...from the dream...I'm not gonna last long..." I felt guilty and ashamed -- I was lying and I was definitely going to cum quickly for her.

"I want it...just go slow...you can last..." she whispered, still sleepy, but plaintive.

Slowly, I pulled my cock out of my boxers and adjusted my angle, sliding my thick length into her. Fuck, she was tight. We both moaned as I worked inside her. "Mmm...you didn't even get to grab my tits earlier...do it now...play with them...fuck, you feel nice..." she sighed, pushing her back against my chest. Fuck, she felt good. The mix of guilt, shame, and sheer arousal was turning me on so much.

Slowly, I reached around her and started fondling her breasts, squeezing them. She moaned, pushing her ass back to take more of my cock as I groped her breasts. They felt good in my hands, full, and soft, and her sounds...I felt myself getting even closer.

"You like how they feel...?" she moaned the words out.

"Yeah, Claire, your body is incredible..."

"You're gonna cum for me, aren't you..." her voice was still sleepy, only half-awake, but pleased. "I asked you to last but you're not gonna...you can't...again..."

Fuck. "I'm trying...Y-your tits are amazing..." I was trying to hold back, but the way those big tits felt in my hands, how tight she was...

She sounded aroused, gasping at me squeezing them, and I felt her getting wetter around me. "Mmm...S-sometimes...I can cum just from having them played with...but you're gonna cum too fast for that this time..."

Well, that idea was too much. Moaning, I orgasmed, continue to caress her tits as I pumped her full of my cum. I felt guilt and shame -- this was the second time I hadn't been able to last for her in one night, and this time it was because watching Brittany had turned me on beforehand...

"Mmm...maybe another time..." she giggled, still not fully awake, snuggling back into me, and we lay there, drifting back off to sleep again together.

---

Brittany crept away from the door to Claire's room. She was still in disbelief. She hadn't expected Rick to actually keep himself cumming when she'd noticed him in the hallway, given how turned on he had looked; it didn't seem like the guy had any self control. She'd been half-hoping that he would just walk into the living room and fuck her, for however long he lasted. But she'd been fully prepared to conveniently look away and let him save face and get back to Claire's room.

This was different, though. Instead of finishing, he had gotten turned on watching her, and gone back to Claire's room...and she had listened to him briefly fuck Claire...while Claire teased him about not lasting long enough. Between his reaction to what she had been saying and what Claire had been saying, it seemed pretty clear that he liked being teased.

Her lips curved up in a smile. This would be fun.

---

CHAPTER 19

The next morning, Claire was hungover and I was guilty, and it meant we didn't talk much. I had a cup of coffee and then we hugged and kissed as I walked out the door. I tried to take that as a good sign. Mostly, I was grateful to get out of there before Brittany was awake.

That gratitude was short-lived when I got a text from Claire a few hours later.

Claire: Hey, uh, Brittany asked me for your number so she could text you. It cool if I give it to her?

Well, fuck. Brittany already had my number, but she was asking Claire so that I'd know to unblock her.

And the only reason she'd be doing that is if she knew what happened last night. I could feel my face flush crimson. She had seen me.

I didn't want her to tell Claire that. I replied. I thought she already had it, to be honest? But yeah, it's cool.

And then I unblocked Brittany, and braced myself.

She texted me a minute or two later.

Brittany: You have a good time last night?

Yeah, that was pretty much what I expected. But I decided to play dumb, make her say it. Yeah, Claire and I had a great date night. Don't think I saw you, though.

Brittany: Oh, I think you did...you probably remember this outfit...

She sent a pic from what must've been her earlier in the evening, dancing at a rave, wearing the mesh top and green bra. She looked good. She always did.

My face flushed, and then my phone pinged again.

Brittany: I was a little surprised by what you were wearing though. Did you have other clothes on for the date with Claire or were you in boxers the whole time you were at our place? ;)

I decided I was going to keep playing dumb. Uh, what? We had dinner and then I was in Claire's room the whole time.

Brittany: Rick. I saw you. For someone who doesn't seem to like me much, you seemed to enjoy the show. And then after watching me got you all hot and bothered, you went into Claire's room and blew your load in her in 30 seconds. Like a loser.

Well, there it was. I had been expecting it. I didn't know what to say in response. I wasn't sure what to do about the situation. After a few minutes, my phone pinged again.

Brittany: So look, here's the deal. I want to talk about it. In person. Tonight, at 8pm, come by my place. Claire won't be home; she's getting dinner with friends and then going straight to some study session. I think you know the address. If not, maybe I'll find someone else to talk to about how much you enjoyed my little show...like Claire. Or Emma.

I sighed. I guess I was headed to Brittany and Claire's tonight.

Claire texted me as well.

Claire: hey...sorry if I made things weird last night. I think I'm just feeling insecure about you dating Olivia.

This, in a surprising turn of events, felt a lot easier to navigate than Brittany blackmailing and bullying me. I replied. Hey, I get it. I am trying to figure out what I want, and I know that's hard. But I had a great time last night. It wasn't weird. Dinner was awesome. So was everything else.

Claire: I had a good time too! Can I...sit in your next massage session?

This felt like it was a little risky, given how she was feeling, but she had already sat in on one...I'll talk to Olivia about it, but I don't see why not.

Claire: Great! I'll see you later this week. xo

I texted Olivia: Hey. I had a great time on Friday. Claire wants to sit in on our next session. I told her I was cool with it.

My phone pinged, twice.

The first ping was a photo from Claire -- A shot of her breasts, neck to navel in frame as she lay on her back, topless. Her big, creamy tits were on full display, one arm wrapped around and underneath them, the other one tweaking one of her nipples. She looked amazing.

The second ping was a text.

Olivia: I mean, if you want her to see how you're gonna use those 40 seconds, it's fine by me...maybe she'll want to play, too.

Fuck. I had forgotten about the stakes from our last bet. I thought about backing out with Claire, telling her she couldn't sit in...but I realized that would probably just make it even worse. Especially if that was how I replied to the photo she just sent. And Claire already knew what the stakes were...maybe that was why she wanted to sit in, I thought glumly.

My phone pinged again. It was a photo from Olivia this time. It was a gym selfie -- the trashy kind of gym selfie. Taken in a gym bathroom mirror in front of some lockers, sticking her tongue out and lifting up her shirt, waist twisted to show off both her ass in workout leggings as well as her abs.

She looked fucking great.

I was rock hard. Having both of them sending me photos was way beyond anything that had happened in my romantic life before now; I had no idea how to handle this. But it was a nice feeling to have both of them so clearly...into me. And it beat thinking about this conversation with Brittany. Fuck it.

I found some decent lighting and snapped a shot of the thick length of my hard cock, outlined in grey sweats -- and sent it to Claire and Olivia, one after the other, with the same message: See you later this week.

Then I went to jerk off. Friday's appointment was likely to get...messy, but for now, I was going to ride the high, I decided.

---

That emotional high faded and was replaced by anxiety well in advance of the conversation I was supposed to have with Brittany. How the fuck was this going to go?

I realized I needed some advice. Brittany was one problem, Claire and Olivia another. My love life -- if that was the right word for whatever this was -- was a fucking mess. I thought about who might give me good advice. It needed to be someone who'd understand the situation, but not someone who was in the situation...

Only one option stood out. I pulled out my phone and sent an email.

That helped me feel better, but by the time 8pm rolled around I was a bundle of nerves again as I showed up to Claire and Brittany's apartment building. Brittany was waiting in the lobby…like Claire had been, the first time I had visited. She gave me a cheery wave as I walked in, and headed towards the elevators to go up to their floor.

Emma had always called Brittany her "hot friend", and that was on full display tonight. Dark hair up in a ponytail, makeup done in a way that looked natural, but somehow made her green eyes luminous. She was wearing athleisure -- white leggings, a matching crop top hoodie on, unzipped enough to reveal a strappy sports bra showing off cleavage. She looked like her job was literally to stand around in a gym and look hot, and she had just come from doing that for a few hours. Hell, she was a personal trainer at some high-end gym -- for all I knew, that was her job.

"Hey, Rick." She grinned, teasingly, as the elevator doors closed behind us. "Or maybe I should say hey again, because we keep seeing each other...or at least hearing each other..."

I blushed. Fuck. "Brittany..."

She waved a hand at me. "Relax, I'm just teasing you. Jeez, always so uptight...I wonder if that's why you, y'know..." her smile deepened, "...pop so easily." The elevator doors opened and we walked down the hallway to her and Claire's apartment.

Her tone was turning me on. It was very reminiscent of my sessions with Olivia, and I felt almost conditioned to respond to it. I tried to ignore the feeling of my cock getting hard as I closed the door behind me. "What do you want, Brittany?"

"Well...let's cut to the chase...I heard you with Claire last night again," she said, smirking. "It sounds to me like someone cums pretty quick routinely..."

It was hot, hearing her say it, but God, I fucking hated her in that moment. Olivia and Claire had always made the teasing playful, fun. With her it was just...mean. I felt a sinking feeling, but tried to put her on the back foot. "So you're just getting your rocks off listening to me and Claire, huh? Weird..."

She laughed. "Oh, believe me, I need someone who can last a lot longer than you can to get my rocks off..."

I spluttered. I was completely off balance, and worse, I felt...very...exposed, sitting in their living room. Claire could walk in at any moment.

Brittany seemed to take in my discomfort, and giggled. "Aw, worried Claire will show up? I told you, she's in a study group. Or maybe the couch just reminds you of...y'know..." She grabbed one of the cushions, and in exaggerated fashion, started riding it, making eye contact with me, and saying "oh, fuck yeah, Rick..."

Well, fuck. She was really hot. I was hard now. I felt both ashamed and angry at how easily she had me reacting to her. And I didn't want to stand in the living room where Claire could walk in at any moment.

"Ugh, yeah, let's go into your room if you want to keep talking. I can't believe I’m even here..." I muttered.

She gave a winning smile. "Well, if that's what you really want, Rick...it's right this way..."

She led me into her room. Not nearly as girly as Claire's. She shut the door behind me and locked it.

Now I didn't feel exposed...I felt trapped instead. She gave me a predatory grin. "So...you seemed to really enjoy what you saw last night." It wasn't a question.

"I-I was already turned on when I woke up. No way I'd be into anything you were doing." I tried to protest, and I was angry enough -- at her, at the situation, at myself -- that it sounded at least plausible.

"Yeah?" Her tone was blunt. "It looked to me like that big dick was leaking precum in your boxers and you stopped in the hallway to touch yourself while you watched me." She crossed her arms under her tits, which only accentuated her cleavage.

I tried not to notice, scoffed, and ran a hand through my hair. I was feeling angrier by the moment. "Whatever. You're hot, but I don't find you attractive, Brittany. I think you're a terrible person. I'm only here because you were threatening to tell Claire or someone else about..." I trailed off and gestured expansively.

She smiled, knowingly. "...about how you were jacking off watching me masturbate? How you thought it was hot listening to me talk about training you to last longer? And then you went right back into Claire's room and fucked her? I mean, Rick, c'mon. If you were serious you would've gone back to her room and had a good laugh with her about how I was fantasizing about you. But you didn't." She giggled. "By the way, by the sounds of it, you could really use that training."

I blushed. She was obviously right. But I tried to maintain my anger. "Whatever, you can talk all the shit you want, Brittany. I wasn't the one masturbating thinking of you last night, it was the other way around. Are you just mad I didn't want to hook up with you after that night at Muse? Maybe you were hoping I'd give you a call after Emma and I broke up?"

She was unfazed. "After Emma dumped you, you mean. For being a two pump chump. Fantasizing about you getting me off is the only way it'd ever happen."

I snorted, anger winning out over my embarrassment again. "If you were actually Emma's friend you wouldn't have been all over me the second you found out how big I was and Emma went to the bathroom. Don't pretend like you care that she dumped me. And last night it certainly seemed like you liked the idea of...what was it? Me spraying a load all over your face?" I put as much sneer in my voice as I could, given how turned on I was, and tried not to think about what that would actually be like.

She had the decency to blush at that. "Hey, we've all got our foibles. Mine is big guys...losing it all over my face..." She glanced down at my crotch, and I felt my cock twitch. I was hard, given the conversation, and it was all too easy for me to imagine. But then she looked back up at me. "Just like yours is pretty girls teasing you until you fucking blow your load in seconds like a loser."

I sighed, the fight going out of me. This was just exhausting. "Brittany, why am I here? So I can be your verbal punching bag? If you're going to blackmail me just get on with it."

She laughed. "Aw, tired of being made fun of for cumming so quick? Look. Admit that you were fucking turned on by seeing me, that it was so hot, I had your dick leaking. Admit the only reason you didn't stay and rub one out while you watched me cum is that you didn't want me or Claire to catch you. And you were so turned on that when you got back into bed with Claire, you busted in like, thirty seconds. If you admit all that, I'll let it go, and I won't tell Claire."

I reddened. "Th-that's not true..."

I'm sure she could see the arousal and anger warring on my face, because she giggled. She stepped closer, reached out, and gave my thick cock a squeeze. "Then why are you so hard right now?"

Something in me snapped when she touched me. Maybe it was the look in her eye -- I could tell she liked how big I was, a lot. Maybe it was that I was just so angry -- the feeling of powerlessness, the way she was blackmailing and bullying me, how hot she was...regardless, she must've seen something shift in my expression because she stepped back, and opened her mouth to say something, but I cut her off.

"So you like guys with big dicks cumming on your face, huh?" Slowly, almost threateningly, I unzipped my pants. I wasn't sure exactly what I was doing, but I had had enough.

"I, uh, yeah..." she was staring now, biting her lip and watching as I slowly pulled my thick length out of my pants.

"Well if that's what you want, Brittany, I'll fucking give it to you." Slowly, but firmly, I reached out with one hand and put it on her shoulder, pushing her down. She sank to her knees, silently looking at my cock openmouthed.

I started pumping myself. This was hot -- she was uncharacteristically submissive, quiet, just kneeling in front of me. The situation was turning me on, and I wasn't going to last long looking down at her, but I didn't care. "If I do this for you, you can't tell Claire. About any of this."

"I won't...I'll do whatever you want..." she trailed off, watching as I pumped my cock inches from her face.

She reached out like she wanted to caress it, but I pushed her hand away, trying to keep control of the situation. "Nuh uh. No touching. Be a...good girl."

She made a needy sound, but didn't move her hands again. "Fuck, you look really turned on..." she practically moaned the words at my dick.

"Yeah..." I grunted. I wasn't really sure how I had turned the tables on her, but her, on her knees, submissively staring at my cock, waiting for me to blow my load on her face, was incredibly hot. I was pumping faster now. I wasn't going to last long.

She looked up at me. "You're gonna cum quick..." she whispered.

"Is that what you want? Me to blow my load quick all over your face?" I could feel my orgasm approaching.

"Yes...Fuck, Rick, give it to me..." she said breathlessly.

Fuck it. "It's gonna get all over you, Brittany...it's gonna be such a big load..." I decided as long as I was gonna do this, I might as well play it up. And the idea of spraying a load across Brittany's face -- Brittany, who had done nothing but mock and disrespect me almost as long as I had known her -- was intoxicating.

"I-I know..." she was the one who was stammering, now, staring. It was obvious this was something of a fetish for her; her demeanor had totally changed.

"Mmm...but you were pretty rude earlier...maybe I shouldn't..." I could feel my orgasm getting closer and closer, but slowed down my stroking. I decided I'd toy with her a bit. It was nice to be in control for a change, especially with Brittany. I figured I'd take my time.

But she looked at my cock, and then made eye contact with me. "You...you have to. I want it." There was obsession, desperation in her voice.

And with a moan, in one smooth motion, she lowered her mouth onto my cock, and started bobbing her head up and down enthusiastically. I was caught off guard, and the sensation was overwhelming -- I didn't do anything to stop her.

She couldn't actually take that much of me into her mouth, but she immediately wrapped her hands around my length as well, stroking and sucking simultaneously. And her eyes -- looking up at me, full of need -- were unbelievably hot.

I felt the orgasm rising in me. She was such a fucking bully, but she was servicing my cock.

I think she could tell what I was thinking, or maybe she just realized how desperate she had been, and wanted some pride back. She pulled her mouth off my cock, but kept pumping me with both hands, and looked up at me, a wicked smile on her face. "You're gonna fucking blow your load right now, Rick. You can't last. You're a two-pump chump."

I didn't respond, but I tried to hold back. I wanted this, didn't want her to stop. But I also wanted to stay in control, to prove her wrong. It was just a losing battle.

She kept talking, a teasing note in her voice. "If you couldn't handle Emma, you're definitely going to be a quick cummer for me. I mean, if you don't want to cum, then just don't. But I want you to spray it all over my fucking face, and I bet you're going to..."

She was just wrapping up the last sentence when the sensation of her hands pumping me with wanton abandon, how turned on she looked, and the words combined to bring me over the edge. I moaned and started cumming, thrusting into her hands. She gasped as my cock jerked and twitched, pulsing rope after rope across her face.

Fuck.

We stared at each other, both of us panting. She looked euphoric, and like a complete mess. A mess I had made. Yeah, I had cum quick, again, but she...wanted it.

It didn't take long for the guilt to set in, though. I decided to speak first. "We're settled. Squared up. You don't say anything to Claire and neither do I."

She nodded.

I grabbed a box of tissues off her desk and handed them to her. "Nothing to Emma either."

She nodded again, starting to wipe herself clean.

I zipped up and got ready to go. The post-nut clarity was now setting in: I had no idea what time it was. I still didn't like Brittany. I still wanted to see if things could work with Claire, who could come home at any moment. The guilt hit me hard, and alongside it, the realization that this was, to put it mildly, a fucking terrible situation. I already had my hand on the doorknob to open Brittany's room when she finally spoke.

"We should do that again sometime." She sounded turned on, but there was a certain amount of knowing mischief in her voice as well.

I didn't look back. "We'll see, Brittany." Hot as it had been, I didn't want to do it again -- but I wanted to make sure she didn't say anything to anyone, and I figured dangling the possibility was better than cutting her off right away.

I pulled her door close behind me and got out of there as quickly as I could. I didn't feel safe until I was in my car a few blocks away without having seen Claire.

Natasha didn't respond to the email I had sent until late that night. I saw it when I woke up.

Always happy to give some good advice. Why don't you stop by the parlor after closing; there's a new product feature I'd like to test anyway.

I sighed. The testing had been hot, but I was beginning to feel...tired. She was whipsmart -- I hoped her advice would help simplify what felt like an increasingly complicated situation.

---

CHAPTER 20

I woke up on Monday and tried to put aside everything in my personal life and focus on work. I was still on a performance improvement plan -- I had been phoning it in for weeks.

Unfortunately, today wasn't the day for maximum focus. My phone was constantly pinging. The first was a text from Brittany, which made my heart sink.

Brittany: still thinking about last night.

Alongside the message was a photo of herself, sucking on a dildo. The camera was above her -- the same view I'd had last night -- and she was making eye contact with it.

Jesus. I got a bit hard looking at it in spite of myself. I was still feeling guilty for what had happened with Brittany. It had been really hot. But I didn't like her. I just hoped she wouldn't say anything to Claire or Emma. Did I reply? Did I ignore it? What if that antagonized her?

I decided not to reply. Encouraging her felt riskier than antagonizing her.

My phone pinged again a few minutes later, and my heart jumped when I saw it was from Claire.

Claire: Guess who I got lunch with today?

It was a photo of her and Olivia sitting at a bar together. They were sitting next to each other, wearing their typical work attire -- jeans and t-shirts -- but Olivia was biting her lip and looking down at Claire's tits, and Claire was craning her neck around to one side, as if she were trying to check out Olivia's ass.

The idea that they were talking to each other, presumably about me, was...kind of troubling, to be honest. I was glad Claire seemed to have gotten past the jealousy or insecurity or whatever it was about me going on a date with Olivia, but the alternative where they were ganging up on me was...yeah, troubling was the right word.

Olivia texted a few minutes later. Looking forward to our appointment Friday, big guy. I know Claire is too, we were just talking about it. Curious to see how long this appointment will last with both of us so excited to see you... ;)

Fuck. I texted them both the same thing. If you're trying to get a rise out of me, it's working.

I didn't know what we were going to do on Friday but I spent most of the day fantasizing about the possibilities.

When I showed up at the massage parlor late on Monday night, Natasha greeted me at the door herself. As opposed to her usual tight-fitting, low-cut dress, she was wearing...a robe of some kind?

She ushered me inside and into one of the rooms. As I had expected, there was a harness lying there.

She looked at me levelly. "I have a new feature I'd like to test. Do you want to do that first, or would you prefer to talk me through your situation and get my advice first?"

I considered. Probably best to get the advice first -- who knew what kind of weird shit was involved in this new feature. "Uh, advice first if you don't mind...it'll probably take longer..." I blushed as I realized the self-burn I had just inflicted. Natasha smirked, but just said "Okay. So what's going on?"

I spent twenty minutes walking her through the whole situation. I didn't leave anything out -- Emma, Brittany, the appointments with Olivia, Claire, the works. Around minute ten, she held up her hand for me to pause, left briefly, and came back with a fifth of vodka and two glasses, setting them down on the table and pouring us both drinks.

But otherwise, she let me lay it all out in front of her. When I finished -- wrapping up with what had happened with Brittany last night -- she let out a long, slow breath.

"You're a real fucking idiot, you know that?"

I blinked. "Uh...how so?"

She started ticking off points on her fingers. "You loved Emma, I'm assuming, but you let Olivia -- who you barely knew, at the time! -- compose and send text messages to her on your behalf humiliating you. Claire is young and relatively inexperienced with relationships, and you're...well, I'm not going to say you're leading her on, but it's not like you're setting especially clear boundaries with her; the fact that she has already watched you and Olivia is incredibly ill-advised, and it's hard to put that boundary back in place now without making her feel hurt. Brittany is blackmailing you, and you're playing into her hands...we haven't even gotten to the part where you just told me how two of my employees are behaving totally inappropriately at work..."

She trailed off, shaking her head. "Young men are so stupid."

I spluttered. "I'm not young, I'm almost 30!"

She outright laughed. "Rick. You are basically a child, and you're certainly behaving like one. You're thinking with this," she gestured towards my cock. I blushed again.

"And you need to be thinking with this." She gestured towards my head.

"Or at least with this." She jabbed a finger at my heart.

This felt like a little too much poetic license. "Uh, okay? Can you...give more specific advice?"

She downed the rest of her glass of vodka, slamming it on the table a little more forcefully than was necessary, in my opinion. "I can't, actually."

"...Uh..why not?" I was a little disappointed.

She massaged her temples. "It is remarkable to me that I signed you on as an advisor. You talked for like twenty minutes without once telling me what you want. What do you want?"

"Oh...uh..." I considered this. "I want Brittany to stop blackmailing me."

She waved her hand. "This is the most incidental of your problems. Secondary, really."

I blinked again. This conversation wasn't really going the way I had hoped. "Uh, what? I'm being blackmailed, Natasha!"

"Blackmail works because the blackmailing party has information that, were it to reach the hands of someone else -- in this case, let's say Claire, or maybe Emma -- it would prove damaging to the blackmailed individual." She had adopted a professorial tone.

"R..right..." I didn't see the point she was making, but I was beginning to feel like the dumbest kid in the classroom.

"So. Let's start with the easier one. Do you care what Emma thinks?"

I considered this. "I-I guess not very much, at this point..."

"Right. So, information going to her isn't effective blackmail. Maybe Brittany tells her about what you've been doing, and she and Brittany have -- I don't even know what kind of conversation they'd have, but it doesn't seem like it matters very much. Who cares. Now, do you care what Claire thinks?"

I answered immediately. "Yeah, of course..."

"Okay. Why? Because you like having sex with her or because you want your relationship to develop into something more?" She steepled her fingers, staring at me directly.

"Uh, I don't know..." I was starting to see her point.

"And what about Olivia? I don't think she'd care about what you did with Brittany. She might help you burn Brittany's house down or destroy her car when she found out Brittany was trying to use it against you. I've always thought Olivia had that kind of energy about her. What do you want your relationship with her to look like?"

"Uh..." Now I definitely saw her point.

"I can't tell you what to do because your goals aren't clear." She said the words kindly, this time. "Or maybe it'd be better to say that my advice is this: do whatever you need to do in order to figure out what you actually want. That's why this all feels so complicated. You don't know what you want right now. Once you know, I suspect you won't even need to ask for advice."

"I...huh. Thanks Natasha. Glad I emailed you."

She clapped her hands and made a wiping-clean motion, as if shooing away the topic. "I bill $880 an hour for consulting time. This took twenty six minutes. I'll give you the good friends and family discount, so instead of $350 I'll only invoice you for $225."

I was taken aback. $225? She had helped quite a lot..."Um, I guess that's fair?"

She laughed. "Relax, I'm just kidding. Happy to help. And I'm going to overlook Claire and Olivia's indiscretions as employees, although..." she leveled her gaze at me, again. "As an advisor to the business, if this escalates in any way that presents a material risk to the company, I expect you to tell me."

I swallowed hard and nodded.

She stood up. "Now, onto the product feature test. I've finally got a second harness prototype and there's something I've been wanting to try since I originally got the input/output interfaces working at an acceptable degree of fidelity..." She slipped the robe off her shoulders and let it fall to the floor. She was wearing one of the harnesses herself. It looked sexier than I would've expected on her, her tits and nipples prominent through the mesh, the wires and diodes giving the impression of some kind of hot science fiction porn.

I was staring, and realized it. I forced myself to make eye contact with her.

She was smiling. "Now, we have to get a harness on you..." she moved over to me, and gestured for me to strip. I did so, and she started helping me slip into the mesh, attaching sensors, and so on.

"So, uh, what's the new feature?" I was curious.

"Well, two harnesses open up a new world of potential possibilities." She said the words with enthusiasm. "But for this test, I've got the software configured to read outputs from you and feed inputs to me. Your harness will gather arousal data, and my harness will approximate it on my end. So, when you're at, say, a 9.7 on arousal, my harness will do the best to match it. It won't be perfect -- this is very much a first try -- but it'll be interesting."

She stepped away from me, studying the setup of the harness on me, confirming all the connections, and then moved over to the laptop.

I was processing what she had said. "So...as I get more turned on...you'll get more turned on?"

She nodded. "If the software works as planned, yes. I'm curious to see what it's like to experience the levels of arousal you were showing last time."

"...And...when I climax...you'll..."

She grinned. "We'll see if it works, but yes, you've captured the basic logic of it. Lots of interesting applications if it works." "Now..." she clicked a few things on the laptop. "I've turned on the program...so as you get turned on, I should experience it as well."

She looked over at me. I was staring at her body. She glanced at her laptop and pursed her lips. "Interesting."

"Is it working?" I was still staring, and as I watched, she ran her hands over her body. I followed them with my eyes, taking in the sight of her nipples against the mesh, the way the straps hugged her curves...

She inhaled sharply. "It is. Mmm, it's very gratifying to feel how aroused you get just from looking at me. Now, let's start testing..."

She stepped closer to me, so that the swell of her breasts was almost brushing against my chest, and leaned in to whisper in my ear. "I liked how quickly you got excited for me last time, Rick."

I blushed. I was getting harder. "Y-you felt amazing... you really know what you're doing..."

She made a pleased mmm sound in the back of her throat. "Mmm, it's working even for things I say that arouse you. Very good. And yes, I do know what I'm doing...but I liked how you couldn't control that big dick...you had to cum so bad we couldn't even get all the data we needed..."

She reached out and fondled my balls, gentled. I let out a guttural moan -- her touch was assured and exactly right, and my cock throbbed. Almost simultaneously, she gasped.

"That...wow, you ramp up quickly...fuck...that felt very nice..." Trailing off, she leaned in and kissed my neck.

Fuck. Her mouth felt amazing, and the teasing was turning me on. I moaned, and as I did so, her kiss turned into a moan as well. I was rock hard.

I could feel her panting. "It's definitely working...I'm...really getting into this..." she was breathing quick against my neck.

"Y-you might want to slow down..." I said it worriedly, trying to tamp down the arousal I was feeling, but it was impossible. She was grinding against me, now. It was so out of character for her, and that only made it hotter. I could feel my cock twitching, leaking precum on her thighs.

"I don't think I can..." she moaned, and took my hand and put it between her thighs. I could feel how wet she had gotten, which was only making me harder...which, I realized, was only making her wetter.

We were stuck in a reinforcing cycle, and it wasn't going to take that many cycles before I came, I knew.

The idea that Natasha was losing control just like me was building the orgasm in me more quickly than I had expected. I made eye contact with her. "I, uh, don't think this is going to take very--" but my words dissolved into a gasp when she pushed me down, putting my back against the table.

"I need you, now." Her voice was desperate. She grabbed my thick length and, moaning, impaled herself on me in one swift motion.

"Oh, fuck Rick. It's amazing you can even function during the day...that big dick just gets riled up so easily...and now I'm so fucking turned on...God..." she moaned, starting to rock herself on my cock, trying to get warmed up to my girth.

Seeing her losing control was just making me more aroused, and she felt amazing around me. I fought to try to keep in control.

"Fuck...this feels so good...it's almost overwhelming...no wonder you cum so quick..." she was now riding me, vigorously, bouncing and repeatedly driving my cock deep inside her.

I could feel my orgasm building. This was all happening fast. I didn't know how many pumps I was going to last inside her, but it wasn't going to be many.

I tried again to warn her in case she wanted to slow down. "I-I'm not going to last long, Natasha..."

Something of her previous irritated-professor demeanor came out, and she paused. "I know that, you idiot. I'm experiencing the same level of arousal as you are. Shut up and enjoy it."

Oh, right. I blushed, the embarrassment momentarily recentering me.

But only momentarily. She was fucking herself relentlessly on my thick cock in earnest now, leaning over me so her tits were in my face. She wasn't forming sentences, any more, just saying fuck, fuck, fuck, fuck each time she drove down on my cock.

There was none of the skill from last time, no sensation of being milked by her -- she was obviously too overcome with arousal for anything like that. But the sensation of her just fucking me with abandon felt amazing. It took about five whole seconds of that treatment before I knew I was about to cross the point of no return. I met her eyes, and saw that she knew it too -- because she was as well.

Simultaneously, we both arched our backs as I lost control. I came into her, a long, protracted convulsion. I felt her trembling atop me. She managed a few more bounces, but eventually was just spasming atop my length, moaning in ecstasy.

It was, to put it bluntly, incredibly intense. She collapsed atop me, face against my chest, and we both lay there panting for a moment.

"I...wow..." I was speechless. As I came down from my orgasm, it occurred to me that this might have been a big mistake. That had been a really powerful experience, and I wasn't the one getting inputs from the harness. What if...what if she was going to be chasing after me like Brittany was? And I had just told her everything about my other relationships...I felt worried.

Natasha pulled herself up, a bit unsteadily. She look deep in my eyes and let out a little, helpless, giddy, laugh, and then kissed me on the mouth.

That look her in eyes was a little too close to infatuation. Not good, I thought.

I opened my mouth to say something, but she spoke first. "I'm going to make so much fucking money, Rick."

I felt a wave of relief. At least there was one woman in my life that wasn't complicating things.

And then another thought occurred.

"So...how do I get in on the ground floor with this one, Natasha?" I tried to say it confidently, but it was somewhat spoiled when she pulled herself off of me with a gasp halfway through the sentence.

She giggled. "Let's talk."

I might not stand to make as much fucking money as she did off this idea, but after experiencing that...I figured this was a pretty solid investment bet.