Chapter Nine #2
I fucking whimpered like a weak little boy because that was the absolute last thing I wanted to do right now.
“Imagine you’re with the woman of your dreams.”
Okay, so… picture you?
I bit down the words.
“And let’s just say it takes her a while to warm up. Maybe she’s shy. Maybe she’s worried about how she looks.”
“Why in the — fuuuck,” I groaned when Livia tightened her grip slightly, just enough to have that orgasm toying at the edges of my grasp again. I was panting my next words. “Why would she worry about that?”
“Are you kidding? So many women worry about that. Maybe it’s because of a toxic ex or watching porn or reading magazines or hearing godawful sex advice from their mothers.
Believe me, there is ample messaging about how women need to please men, and that sex is not about their own pleasure.
So, yeah — a lot of women will be self-conscious.
They’ll worry if they look fat when they’re riding you. ”
“Stop.”
“Or if their tits are bouncing in the perfect pornographic way.”
“Get the fuck out.”
“Or if they’re making the right face to make you come.”
At that, I stopped where her hand was stroking me — much to my cock’s chagrin. “You’re being for real right now?”
“Do I look like I’d waste lesson time with anything not real?
” Livia began stroking me again, and I sank farther into the couch cushions, my body on fire.
“The truth is the majority of women you bring home are going to need your time and attention and encouragement to come. And you need to not come until you get her there. So,” she said, placing the Fleshlight over my crown again. “Let’s practice holding off.”
“Jesus Christ,” I muttered, but it was cut short with a moan ripping from my throat when Livia slid the toy over me.
She moaned when she sank it down. “Oh, yes, Carter. God. You’re so big.”
“Coming—”
I muttered the word, and Livia laughed as she pulled the toy off, and I fought through another strangely pleasurable, torturous withdrawal.
“Rude,” I said, but it was with a smile of my own, because it was kind of funny.
“I’m sorry,” she said around her laughter. “I just — that was fucking hilarious.”
“I guess I do have a praise kink.”
“I think you have more kinks than you even know exist, Rook.” Livia slid the toy back onto me and I shuddered at the overwhelming sensation.
“Now, focus. Do what you have to do to last. Think about something else — running drills or losing a playoff game or whatever works. If you can’t distract your mind, then zero in on your goal.
Imagine you’re in a game and you have to score — or the team loses.
Resist with everything you have. Last for her,” she said, and then she squeezed my knee as she flexed the toy down farther. “Last for me.”
“Fuck,” I groaned, loving those words from her lips enough to tell her I was about to fucking come again, but I did what she said and fought against it.
I tried to think about whatever I could to distract me from how good the toy felt.
I thought about sand crabs and raccoons, about cooking and paddle boarding, about calm morning waves at the beach and the soft chirping of birds in the evening.
I even tried using Livia’s example of imagining the loss of a game, the shuffle of skates back into the locker room, heads hanging low.
But none of it worked.
Because Livia was fucking me with the Fleshlight, the ribbed gel of it hugging my cock perfectly as the little machine sucked and pulled.
And she wasn’t just silently fucking me, either.
She was moaning, panting, whimpering, making all the sweet little sounds I imagined she’d make if I was fucking her.
“Oh, Carter. Yes. Just like that. Oh, it feels so good. I love when you fuck me like this. Yes. Harder. Faster. Fuck me deeper.”
“Christ, Liv,” I cursed, gritting my teeth against my climax.
When she started pumping faster, granting my silent wish, I knew I was screwed.
Switch gears, you idiot.
Don’t fucking come.
Game time. Imagine it’s game time.
Livia continued on with her moans and words of encouragement, but I did my best to ignore them.
I kept pumping up into the toy but imagined I was on the ice, instead.
I channeled that energy I felt when I was exhausted, when it was overtime and the next person who scored won the whole fucking game.
I imagined it was all up to me, that my one job was to contain my climax.
It was the first time my body listened.
I found an almost Zen-like state of being, like Livia was muted under water. I felt what she was doing to me, but I willed my mind to focus on what I was doing. Every bit of my control went to holding back, to lasting just a little bit longer.
“God, yes, Carter, I’m coming. I’m coming!”
Livia started pumping the toy faster and I bit my lower lip so hard I released it with a hiss.
And then I broke.
“Fuck, I can’t—”
Once again, I didn’t finish the words before Livia removed the toy.
And this time was the worst.
I was one fucking second away from busting, but the moment she pulled off, my orgasm froze. It was like pouring soda into a glass too quickly, the foam rushing to the top — but stopping just before it toppled over the lip of the glass.
Every nerve in my body was alive, burning and tingling as I trembled and cursed and clutched the couch cushions. I was fucking the empty air like I could find relief there, but my orgasm slowly receded, like the tide drawing back out.
“Fucking hell,” I panted, shaking my head. “I can’t. I can’t do it.”
“You can.”
“I can’t.”
Livia grabbed my chin until I looked at her. “Yes,” she repeated, her gaze sincere. “You can. And you will. One more time. All you have to do is last long enough for me to come, and you can come, too. Understand?”
Something about how she referred to the toy as her had me willing to say yes to anything. I nodded, even though I was still unsure I could make it. I tried to hold onto her belief that I could as she lowered the toy back down.
I was so sensitive, so ready that just fucking the thing three more times had me groaning with the restraint not to let go.
“Carter… ooohhhh… God, yes. Yes. Yes!”
Livia dragged each little word out, moaning and making me wait, and then she pumped harder and faster like she was on top of me. She moaned the entire time, screaming out my name while I pinned my bottom lip between my teeth and pushed all my focus into holding back.
You can’t do it, can you?
You weak little fuck.
You’re going to lose it.
You’re going to disappoint her just like you—
I shook my head against the noise, eyes squeezed shut, cock begging me for release, but I refused. I held on and rode out every tantalizing pump of the toy.
And then Livia slowed, her breaths evening out, and when I chanced peeling one eye open and then the next, I was met with a satisfied smirk of her lips.
“Such a good fucking boy,” she praised. “You may come.”
“Oh, thank fuck.”
I panted the words, and then I released the restraint I’d been clinging to, but I didn’t relax. I couldn’t fucking relax. Every nerve inside me was strung tight, and the second Livia started pumping me again, I felt my orgasm rush to the surface.
And it wasn’t like a normal climax. It wasn’t slow and easy and familiar.
It was like a tsunami taking out an entire fucking city.
I barely had time to register that it was happening before my orgasm crashed into me like a wall of water, knocking my breath from my chest as it took me down.
I thought I moaned, or maybe cried out, or maybe sucked in my last breath and stayed completely silent — I couldn’t be sure.
I just gripped the couch tight and held on for dear life.
“You’re still fighting it,” Livia soothed. “Let go. Come for me, Rook.”
I panted, gripping tighter, thighs spreading, ass clenching as I reached and reached and—
“Oh, God! Oh fuck, fuck, fuuuck.” I cried out as my climax finally took me, and it was like having ten orgasms at once.
The pleasure was indescribable, like witnessing a miracle or achieving a lifelong dream.
It wasn’t just surface level. It was bone deep, soul deep, and it whipped through me like a beautiful, punishing wind.
Every muscle was painfully tight until the second I came, and then I was spasming, panting, screaming, succumbing. It was heaven. It was euphoria. It was fucking deliverance.
I couldn’t be sure how long I came for. It felt like hours, but it might have only been moments. Either way, I collapsed on the other side of it, bones going limp and muscles melting into the couch. I was suddenly so tired, I felt like I could fall asleep right then and there.
“That was so sexy,” Livia praised, slowly working the toy off me.
I hissed and convulsed a little when she slid it over my tip, and then we both moaned at the sight of my cum dripping out of the toy and all over me.
“Look at you. You filled me up.”
“Liv,” I panted her name, because fuck, that was the hottest thing I’d ever heard. I wanted to fill her up. I wanted it to be her I got to fuck next time.
“You did so well. But… we aren’t done yet.”
My eyes shot open. “We’re not?”
She shook her head, fingers crawling up my thigh until she was wrapping her hand around my softening cock. I didn’t know whether to cry or moan at the sensation, but the sight of her playing with my cum had me leaning toward the latter.
“For learning purposes, let’s pretend you didn’t last. Let’s pretend you came before she did, but she’s still turned on and ready to go. What would you do?”
I held up my index and middle finger, wiggling them in the same motion that had made her come earlier.
She shook her head. “No, no.”
I made a peace sign and wiggled my tongue between them next.
Livia sucked her teeth. “Come on, now. You will have already done that. If your line was playing in the third period and you were down by one, you wouldn’t ask coach to bench you, would you? You wouldn’t leave it to someone else to finish the job, would you?”
“Liv,” I said, shaking my head. “I can’t. I literally cannot—”
“Yes, you can,” she assured me.
And she squeezed her hand around me, just the right kind of pressure, and started pumping.
“Please,” I begged.
“If you want me to stop, you know the words to say.”
She was asking me to use the safe words if I wanted out, and God, I was tempted. I was fucking spent.
But I was also insatiable when it came to this woman, and watching her play with my cum on her knees had my cock hardening again of its own free will.
Livia smirked at the sight. “That’s it. Get hard for me again, baby. Get me off.”
I groaned, head falling back as she worked me until I was hard as stone. Then, she slid the toy back on.
It was actually easier this time, that restraint I had to hold onto. My body wasn’t wound as tight. I wasn’t quite as desperate. But it was still work as she increased the pace, as she moaned and teased and drew it out until she knew I was actively fighting against coming.
When she said the word and allowed me my second orgasm, I sounded more like I was in pain than in ecstasy. The climax ripped through me swift and sweet, like a little exclamation point on the night.
And then I really did melt into the couch.
“I can’t move,” I mumbled like I was drunk. “I’ll never move again. I live here now.”
Livia just chuckled, and then I swore she pressed a slow, soft kiss against my cheek, but I couldn’t trust my reality at the moment.
“You don’t have to move. I’m going to take care of you. Just relax. You did well.”
That praise was the final nail in the coffin, and the last thing I heard before darkness took me.