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"Feel free to get comfortable, Nick," I said as Nick Brandt walked into the guest room I had set up for clients. I had on only a pair of baseball shorts with nothing underneath. I had a few real massage clients, but I was paying my way through B school with the large shank of meat that was flopping commando beneath the fabric.

Coach Brandt took a quick look and flashed a smile. But he was mostly businesslike as he removed his shoes and hoodie, and along with it, the T shirt beneath. Brandt was coach of a top college football program and was my new best client. Tipped well, and with him the sex didn't feel remotely like work. I almost felt bad taking money from him, but Coach had the salary for it.

The shameless showoff sext had a simple caption: "Come split me open again". We both really relished slowly opening him up, methodically, appreciating every new sensation and reaction. All of the new favorites discovered were remembered to receive further care later.

Alright, bro…

If you’re really turned on after that, you can fuck me and cum inside, but when we see each other next week, I’ll fuck you too.

It’s clear, bro… A deal’s a deal!

“Jesus Christ,” I gasped, taking in the sight of him. “You scared the shit out of me. It’s after 2 am. I’m eighteen now—you don’t have to wait up for me.”

“I know,” he assured me. “I just came downstairs for a glass of water. I was thirsty after your mother and I—uh—after we—”

“Spare me the details,” I cringed, noticing his mussed up hair and the sweaty, post-coital sheen on his body.

“Got it,” Mark laughed. “So—what did you and Brent do tonight?”

“Umm—not much,” I shrugged. Brent, my first boyfriend, and I had been together for only a few weeks. And though I was glad my mom and stepdad were supportive, I still wasn’t comfortable sharing details. “We went to a party and then drove up to lookout point.”

“Lookout point?” Mark smiled knowingly. “I couldn’t begin to tell you how many babes I bagged in the back of my car up there when I was your age. I remember this one slutty bitch who had the biggest set of—”

“Please stop,” I implored, well aware that he had been a pussy hound in his younger days.

“Alright,” Mark acquiesced. “But lookout point is a big step for you and Brent. I take it you two are fucking now?”

“NO,” I dismissed a bit too quickly. “I mean—we’ve, like, done other stuff. But we haven’t fucked yet.”

“That’s—that’s good,” Mark nodded. “So I’m guessing oral or maybe—”

“Jesus,” I groaned. “You ever think that maybe I don’t wanna talk about this shit with you?”

“My bad,” Mark apologized, dejected. “I just want you to know that you can talk to me about this shit. My dad was always there for me when I was your age—shit, he bought me my first box of condoms—and I just want to be there for you, too.”

“I know—I’m sorry,” I offered, realizing that I was lucky to have Mark, and that he was only trying to help. “I—uh—I sucked off Brent tonight, up at lookout point.”

“That’s awesome,” Mark beamed, giving me a high-five. “Was this your first time—you know—going down on him?”

“God no,” I laughed. “I actually sucked him off on our first date—in the movie theater.”

“Damn,” Mark gasped. “You dirty boy. So, I’ve gotta ask—spit or swallow?”

“Swallow,” I answered bashfully.

“Good answer,” Mark high-fived me again. “For me—it’s not a true blow job unless my load gets swallowed. But I get that some people don’t like the taste of jizz.”

“I actually love the taste,” I admitted boldly. “And I think it’s hot to look up into Brent’s eyes as he’s cumming down my throat.”

“I wish your mom felt the same,” Mark rolled his eyes.

“Too much information,” I pleaded, covering my ears in mock offense.

“My bad again,” Mark laughed. “So you and Brent—have you talked about fucking? Him fucking you or you fucking him—or however the hell it works with two guys?”

“Yeah—um—Brent wants to fuck me,” I admitted candidly. “But I—I haven’t let him yet.”

“Why not?” Mark ventured. “I mean it’s probably the same as with women. It’ll kinda hurt the first time, but then you’ll get used to it and will love it.”

“Yeah,” I nodded. “I mean, I know that.”

“Then what’s holding you back?”

“It’s—it’s stupid,” I shrugged.

“Nothing’s stupid. You can tell me.”

“It’s just—it’s just that I’m still a virgin, and Brent has a lot more experience than me,” I shared. “He’s been with, like, eight guys. And I’m afraid I’ll disappoint him—that I won’t know what to do.”

“Brent seems like a nice guy,” Mark countered. “I’m sure he’ll be patient and gentle with you, knowing it’s your first time.”

“That’s the problem,” I admitted. “He doesn’t know it’ll be my first time. I was embarrassed to tell him I’m a virgin, so I lied and said I’d been fucked before.”

“Christ,” Mark whistled. “Then you gotta tell him the truth.”

“I can’t,” I refused. “It’s embarrassing that I lied to him.”

“What about giving up your cherry first to some other guy—a buddy, perhaps?” Mark thought out loud. “The first time is overrated anyhow. Just get it over with. Brent wouldn’t have to know.”

“I don’t—I don’t know anyone—” I began to reply, until I noticed Mark was hard from all this talk about sex. His big cock was straining against the flimsy fabric of his white briefs, the purple tip nearly peeking out the top of his waistband.

“YOU could fuck me,” I suggested boldly.

“Oh no—absolutely not. No fucking way,” Mark spat. “First, I’m straight—I don’t fuck guys. And second, your mom would cut off my balls if she found out I fucked her son.”

“Mom would never know,” I insisted. “Please, Mark. I need this. You gotta—”

“I said NO,” he barked.

“Do you fuck mom in the ass?”

“What?! I’m not gonna—”

“Oh, so you can ask me about my sex life,” I spat, “but I’m not allowed to ask you.”

“Okay, fine,” Mark agreed. “Your mother won’t let me near her back door. She thinks it’s nasty.”

“So that means you’ve tried—that you want to fuck her ass?”

“Well—duh—most straight guys want to at least try anal.”

“So you’ve never tried it?”

“No,” he shrugged.

“Not even once—with all those bitches you used to bag up at lookout point?”

“No,” he admitted. “The truth is—with the exception of pornstars—most women don’t like the idea of anal.”

“Then try it with me,” I pleaded, eyeing his rock hard cock, precum bleeding through the front of his briefs. “You know I’m gonna be super tight. And you can cum up my ass—dump your load in me.”

“That’s enough,” he scolded, turning toward the stairs. “I’m not gonna fuck my own stepson. I’m going to bed, and I don’t want to hear about this again. Discussion over.”

I nodded my head, crestfallen. The truth was that I had been attracted to Mark ever since he came into my mom’s life. And once they married, and he moved in with us, my attraction only grew stronger.

It didn’t help that Mark often walked around the house in his briefs—the outline of a thick cock with a fat head tormenting me daily. And the nights when he fucked my mom—the bed springs squeaking, my mom’s soft moans under his weight, and his grunts when he dumped his load in her—well, it drove me mad with envy.

Resigned to not losing my virginity to Mark, I went upstairs, brushed my teeth, and climbed into bed. I was just dozing off when my bedroom door creaked open, the silhouette of Mark in the doorway.

“This never leaves this room,” he announced, pulling off his briefs, his big cock springing free at full rigidity in the moonlight flooding through my window. His dick was even bigger than I expected. I had to have it.

Kicking off the covers, and sliding off my briefs, I reached for my jacking lube in my bedside table. Flat on my back, I opened my legs and began to finger some lube into my hole as Mark climbed onto the bed.

“Flip over,” he ordered. “I’m gonna fuck you from behind.”

Obediently, I got on my stomach, my ass raised slightly for him. Mark’s hands went to my hips, gripping me as his mushroom head found my hole.

“I’m just gonna rip off the bandaid and get it over with,” he announced, pressing into me. “It’ll hurt less this way.” And then—WHAM—Mark’s big dick was inside me. Cherry popped. A virgin no more.

“FUCK,” I screamed, feeling like I had just been split in two.

“Shut the fuck up,” he scolded. “You wanna wake up your mother?”

“I’m sorry,” I winced. “It hurts like fuck.”

“Just relax,” Mark stroked my back, keeping still inside me. “You’re tight as fuck, and I’m thick. You just gotta adjust to it. It’s the same with women. Give it a minute.”

I took a deep breath, Mark’s hands moving to either side of the bed as he planked above me. I knew it would hurt the first time but, fuck, it felt like his arm was in me.

“You’re doing good,” Mark encouraged. “I can feel you relaxing your grip on me.”

And he was right. My hole was accepting him, my sphincter giving up the fight and relaxing. I had to remind myself that men have been doing this for ages—and I could too.

“I’m gonna start slow,” Mark announced, giving me a few tentative strokes, followed by a deep thrust.

“FUCK,” I wailed, his balls mashed against my cunt.

“Too much?”

“No—it feels good,” I purred, licking my lips as he proceeded to deliver some more deep thrusts into my bowels. “Does it feel good for you?”

“Christ, it’s good,” he admitted readily. “The tightest hole I’ve ever fucked. I’m warning you—it’s gonna be a quick ride. I’m already trying to hold back.”

“Then fuck me—fuck me hard,” I begged, relishing the fullness inside me, his big cock exploring my depths.

“Be careful what you wish for,” he teased, picking up his pace. He was giving it to me hard, destroying my virgin cunt, making it his own.

“Fuck me,” I cried. “Harder.”

“Yeah? You like this big cock in you?”

“Yes,” I exclaimed, gripping the pillow.

“You want me to cum in you—shoot my load in your tight, little cunt?”

“Yes,” I begged. “Fucking breed me.”

“Good—‘cause here it comes,” he bellowed, his balls slapping my ass at a frenetic pace. I could feel his cock swelling inside me, increasing in girth. And then it began—a deep throbbing inside me, like a heartbeat in my depths.

“FUCK,” Mark grunted, his cock releasing into my void. “Yeah, take this fuckin’ nut.”

He collapsed on top of me, a sweaty mess as his balls continued to empty within my virgin domain. I relished the feeling of him cumming inside me. Never had I felt closer to Mark, a deep sense of belonging.

“Christ, that was good,” he growled in my ear. “You’ve got a cunt made for cock.”

And then he pulled out of me abruptly, his load spilling out of my gaping hole. Panting, he retrieved his briefs from the floor, using them to clean off his wet cock.

“Your boyfriend is a lucky man—he just doesn’t know it yet,” Mark laughed to himself as he staggered out of my room, closing the door behind him.

I was worried things could be weird between us, but Mark was his same old self the next day. At dinner that night with my mom, he was completely normal. It was like nothing had happened.

“You have plans with Brent tonight?” Mom asked, passing me the mashed potatoes.

“Yeah,” I replied. “Brent is picking me up later after his shift at the restaurant. We’re just gonna drive around—hang out some.”

Mark gave me a wink, knowing I would be giving up my hole to Brent that night. I was happy to no longer be a virgin, and for Mark’s part in that. But, secretly, I wished Mark would fuck me again. But it was foolish. I knew our clandestine fuck was just a one-and-done.

It was after 2 am when Brent dropped me back at the house, his load swimming in my depths after fucking me twice at lookout point. I was disappointed Mark wasn’t waiting up to greet me, as I wanted to tell him all about it—how I took Brent’s cock like a champ, thanks to Mark.

As I dozed off to sleep, my door creaked open like the night before. Wordlessly, Mark climbed on top of me, pulled down my briefs, and slid his big cock into my wet hole, slicked with Brent’s load. With his hot breath at my ear, Mark whispered, “I hope you enjoyed Brent’s cock tonight, because I’ve spent all day thinking about fucking your used, cummy cunt.”

Stories are fiction and intended for readers 18 and up. All characters are assumed to be legal, consenting adults.