Never Have I Ever: Wanted my Brother’s Rival

“Hi, Suzanna, hi Stripes. Hi, Jayjay.” I smiled at the camera as some of my regulars greeted me in the chat.

jayjay4: what’s the big announcement?

SuZaNnA sent you a tip!

SuZaNna: what’s your announcement?

“Thank you, Suzanna. You’ll find out soon enough. But it’s a fun one, I promise.”

The chat lit up with greetings and people asking about my announcement. The odd comment demanding to see my dick, ass, or feet also popped up, but I ignored them. I’d learned long ago that feeding the trolls only made them louder.

I’d turned on the feature that allowed me to see the handle of every person who came into my room. It made the chat fly by as the names flashed between messages, but I didn’t have any trouble following both.

NotEast5 has joined your room!

My greeting died on my lips. My mystery tipper was going to watch my show?

A line of messages shook me out of my stupor, and I focused on making small talk and not on the weird flutters in my chest.

stripes: tell us a story while we wait for the good stuff

“A story?” I smiled and tapped my chin like I was thinking. “Okay. Once upon a time, in a land far, far away.”

My chat went crazy with protests.

stripes sent you a tip!

stripes: not that kind of story;)

“Okay then, what kind of story do you want, Stripes?”

stripes: tell us more about your roommates

“My roommates, huh?”

stripes: something hot

“Something hot about my roommates. Okay.” I looked around like I was making sure no one was in the room with me and we were exchanging secrets. “The one who lives in the room beneath mine still hasn’t closed the vent I told him about months ago. I get a front-row seat to their dirty talk every time he and our other roommate get it on.”

SuZaNnA: do you think he did it on purpose?

coldbreww: thats so hot

assssman6969: are they hot?

“I’m not sure if it’s on purpose. He might have forgotten.” I leaned back on my hands. “But I’ve heard them talking about all the times they’ve fucked in the library, so maybe they like knowing I can hear them. I’m certainly not complaining.” I ran my hand over my chest. “And yes, they’re hot.”

I chatted about my roommates for a few minutes, making sure not to say anything that could even remotely identify them. When I hit my viewer goal, I got to business.

“Time to start.” I picked up the notebook and pen I’d set out earlier. “I was thinking it would be a fun night to play a game. I don’t know about you, but it’s been a long, hard week, and I could use a little fun. How about we play a few rounds of Never Have I Ever?”

I’d gotten the idea at the beginning of the year when my roommates had played before going out one night. I’d heard them in the living room, and after listening to a few rounds, I’d been convinced everyone in the house other than Finn were empty-headed party kids and I needed to stay away from them.

What I hadn’t known was the game was supposed to be outlandish and crazy and shock the people you were playing with. That the things they’d revealed were the exception, not the rule when it came to their experiences.

“Since I can’t drink, I thought I’d add my own twist to things. Strip Never Have I Ever.”

The chat lit up. They liked the idea.

“Rules are simple. If you have a ‘never have I’ question you want me to answer, put it in a tip. I’ll write down the ones that come in, then randomly choose one to answer. If I have done it, you get nothing. If I haven’t, then I take off an article of clothing.”

SuZaNnA: isn’t it supposed to be the opposite? You drink if you have, so wouldn’t you strip if you have?

I smiled sweetly at the camera. “We could do it that way, but we’d be here forever. I mean, I’m not exactly the most experienced guy.”

That made the chat go crazy, and tips poured in. People loved innocence.

By the time the tips stopped, I’d written down an entire page of statements. Most of them were innocent enough, but a few made my skin crawl. I wouldn’t be reading those, tips or no tips.

“Now for the fun part. You’re welcome to strip along with me. Being naked with friends is always more fun than being naked alone.” I winked. “Don’t you agree?”

“Once I’m down to nothing, the real show will start.” I set a show goal on my computer. “Hit that, and the Hush comes out. The tip menu is active, and for the new people, I don’t put up with abusive language or bullying of any kind. My room rules are in my bio, and I have no problem kicking people out if they break them.”

I made a show of waving my pen around and dropping it on the page like I was randomly choosing a question. I’d already decided which ones I was going to answer, but people loved theatrics. Might as well give them a good show.

“Never have I ever hooked up with an older woman.” I ran my hand down the front of my hoodie. “The first girl I kissed was a year older than me. Does that count?”

I paused to give people a chance to answer, then yanked the hoodie off and tossed it aside. “I guess not. Next one. Never have I ever taken eight inches.” I pretended to look thoughtful. “I supposed this one would depend on what you mean by eight inches. Eight inches of what?”

Dozens of messages with varying words and phrases for “dick” scrolled through my chat.

“You think they meant have I taken an eight-inch dick? If that’s the case, then I’d best lose this.”

I pulled off my T-shirt, subtly shifting so the light showed off my abs. “Ready for the next one?”

I spent the next ten minutes answering various statements and taking my time teasing my viewers as I slowly stripped and played up my innocence. I made it a point not to lie on cam, but I did sometimes stretch the truth. For this game, I didn’t have to. My total lack of experience worked in my favor.

“Uh-oh.” I grinned and tossed my briefs onto the floor. “Looks like I’m naked. Whatever will I do with myself now?”

Tips and suggestions rolled through the chat. This was the easy part of the show. I didn’t have to be charming or cute. All I had to do was focus on the tips and deliver what people paid for.

queenie sent you a tip!

My screen flashed, the sign my goal was surpassed.

“Thanks, Queenie.” I got up on my knees to show off my semi. “Looks like the Hush is coming out to play tonight.”

Ignoring my computer for a moment, I pulled the vibrating butt plug and my lube out from under my pillow. I kept my phone off-screen, connected the toy, then used the app to connect both to my laptop.

The toy was a crowd-pleaser and a good money-maker. The more they tipped, the harder and longer it vibrated. I’d prepped in anticipation of hitting my goal but still made production of spreading my legs and working the toy in. I thanked the people who tipped, and kept an eye on the chat for anyone breaking my rules or being an asshole.

Most cammers had moderators to help them, but I did it on my own, same as everything else in my life.

When the toy was in, I leaned back and slowly stroked myself. Keeping one eye on the chat and being cognizant of my poses and how I looked on cam helped distract me from the pleasure spreading out from my ass as the toy buzzed and vibrated. I did my best to interact with my viewers and keep from getting too close as I edged myself, the toy amplifying every stroke.

After nearly half an hour, the buzzing in my ass shifted to pain. My prostate was oversensitive, and my dick ached from the friction of stroking for so long.

“I don’t know how much longer I can hold out,” I said, my voice low and broken. “I’m so close. I need to come.”

The chat lit up, and the tips came pouring in. The toy switched to the highest setting, and a shock of pleasure tore through me.

buckeye: come on your face!

I chuckled, struggling to focus on the chat and not on my impending orgasm. I rocked my hips to move the toy off my prostate so I didn’t come before I hit my goal. “On my own face? Not sure how that would work.”

buckeye: I saw a guy lie back and put his ass up on the wall. Then he came all over his face. Sooooooo hot

The toy hit just right, and I moaned. “Maybe next time. Not sure I’m coordinated enough for that.”

NotEast5 sent you a tip!

The toy went haywire inside me. My mystery tipper had tipped the highest amount the toy could recognize. It pulsed and buzzed, switching from high to low in a random pattern that rocked me all the way to my core.

“Holy shit,” I panted. “Holy shit.”

I’d had people tip this much before, and it never failed to send me flying over the edge. Pleasure coiled deep inside me, my mind going blank as tendrils of need snaked through me.

“Oh god!” I threw my head back as the pressure snapped, like an elastic pulled beyond its tensile strength.

Waves of pleasure rocked me, and I came hard, writhing and squirming on the bed, the toy lighting me up from the inside.

Groaning, I grabbed my phone so I could turn the toy off when the haze of my orgasm faded. The app had a line of tips still in cue and would continue to go off if I didn’t, and I couldn’t handle any more tonight.

Getting up on my knees, I gave the camera a crooked smile. “Be right back. Then it’s pillow talk time.”

Shakily I climbed off my bed, moved out of frame, and gently tugged out the toy. Using my T-shirt, I wiped off my chest, then got back on my bed and lay in front of my laptop.

stripes: that looked like a good one

SuZaNnA: what were you thinking about?

babygirl702: show feet

toolguy: cum again!

I chuckled at the screen. “It was a good one. And I was thinking about my announcement and how much fun it’s going to be.”

The chat went wild.

muscles21: pillow talk time!

“It is.” I rested my chin on my folded hands.

I called the postorgasm portion of my shows “pillow talk time.” I tended to lose about half my viewers once I came, but most of those were lurkers or nontippers. My regulars loved it, and truthfully, I did too.

Being able to chat without having to worry about trying to make money was a nice way to come down after a show. Sometimes I had to log off right away, and I hated the emptiness that filled me after going from interacting with people to being alone with my thoughts.

jayjay: whats your announcement????

I smiled and pulled in a deep breath. My body tingled from my orgasm.

sitonmyface222: what’s on your arm?

I was used to this question. “It’s a glucose sensor.”

bendmeover99: why?

sweetiepie444: what does it do?

“It’s part of my CGM, or continuous glucose monitoring, system. I use it to check my blood sugar.”

sitonmyface98: you have diabetes???

“I do. Type 1.”

I didn’t particularly like sharing my medical information with hundreds of strangers on cam, but the white disc attached to the back of my triceps wasn’t something I could hide. I’d learned it was better to just put the truth out and not make a big deal out of it.

“Do you want to hear my announcement?” I changed the subject, then waited as the chat went crazy. “Well, I’ve decided I’m tired of being a twenty-year-old virgin.”

The chat went nuts again. My regulars knew I was a virgin, and I’d said as much during Never Have I Ever, but not everyone in the chat believed me. I ignored the rude remarks and ones accusing me of lying.

“And since I’m tired of waiting for my Prince or Princess Charming to come along, I’ve decided it’s time to do something about it.”

kwiky579: partner show!

daddy4u: I’ll pop your cherry

hiball7: fuck me

farmerbobby: I volunteer as tribute!!!!

papabear352: I’ll rail you so hard you wont be able to walk for a week

I chuckled as the messages scrolled by. “I’m glad you’re all so enthusiastic about this. I thought about making some content with another model but figured I might as well fuck one of you instead of a stranger.”

The chat went so quiet I checked to see if I’d lost my internet connection. Then, it went insane as messages flew past. I didn’t bother reading them and scanned them to make sure people were reacting positively.

“You like that idea?” I grinned and popped my ass. “You want to be the first to fuck me?”

I waited for the chat to quiet down a bit. “I’m going to hold a live auction. It’ll be a private show, so if you want to bid, you’ll have to buy a ticket. If you only want to watch, that’s fine too. Once the show starts, I’ll keep tabs on the tips that come in, and whoever tips the most by the end wins.”

A flurry of messages flew past. A few questions caught my eye, and I did my best to answer them.

“I’ll release the rules of the auction before the show, but winning is only the first step. My safety comes first, so there’s a list of conditions the winner will have to meet before anything happens. If you can’t fulfill the terms, then you don’t get my ass or a refund.”

SuZaNnA: what about women? Is the auction open to us too?

“Of course. I’m equal opportunity.”

daddysbabygirl18: have you fucked a girl before?

“Nope. I’m a true virgin. Only kissed one guy and one girl. Never done anything else.” I winked at the cam. “The winner will get the same options regardless of gender identity. You can fuck me, or I can fuck you.”

Chat messages flew by, but I ignored them. “I’ve got to sign off. Lots to do. The auction is happening tomorrow at eight p.m. Eastern. Anyone who’s interested will get a chance to go over the rules before the show starts. Entering the private show will be considered an acknowledgment of the terms.”

I went through my closing spiel and logged out of my room. I’d made more in tips than I’d anticipated, and that big tip right at the end was the reason why.

My thoughts strayed to NotEast5. Had it turned them on to know their tip was the reason I’d come?

The hell? Why was I wondering about them at all?

Moving on autopilot, I shut down my laptop and put away my ring lights. At least the hot water was fixed. Taking a cold shower in February wasn’t my idea of a good time.

West had kept his word and contacted Beck about coming by to replace the element. Unfortunately, none of my roommates had planned to be home during the window he’d given, and I’d had to let him in again.

This time I’d stayed in the living room while he and someone I assumed was a plumber changed the element. Then they’d left, and I’d been trying to think about anything other than him since.

Seeing him again had brought back everything from the past six years—hurt, betrayal, anger, and sadness.

The worst part was he still felt like the guy I’d known all those years ago. His quick smile, the way we fell into easy conversation, and how he made me forget to overthink everything that came out of my mouth.

He even walked the same: tall and confident like he owned the world. Which he kind of did.

“Stop thinking about him,” I chastised myself and grabbed a towel. “He’s nothing to you. Just a guy you used to know and your current landlord.”