Blackmailing Benjamin

Some of the best plans happen on the fly. This was probably one of my more genius ideas. At least it seemed that way. I was generally horny but the average college man just wasn’t going to cut it to satisfy me. This entire plan was just a diversion I could masturbate to later. The fact that it would humiliate and traumatize my golden stepbrother in the process was just icing on the cake.

He was a prop as far as I was concerned. I hoped that the looks Andre had given me were indication enough of what he’d like to do later. The man had definitely given me some looks that made my panties wet. So I’d watch Ben take it in the ass, then when he passed out from exhaustion, maybe Andre and I could have a private moment. Yet another bit of ammo I could hold over Ben’s head afterward.

Andre drove us to a swanky apartment in a nicer part of town. I almost wondered if he was a drug dealer until I saw the football trophies and memorabilia everywhere and it finally clicked who he was. My stupid stepbrother had actually managed to fall in bed with a pro? That boggled my mind. I’d probably be even more impressed if I followed sports. Either way, the guy was clearly slumming it, going to a frat party with Ben.

“Kitty Kat, want a drink?”

I turned to the sound of Andre’s deep voice. He held a carton of half and half in his hand and shook it with a wicked grin.

“Fuck you,” I said.

He poured anyway, mixing the milk with Kahlua and vodka. I wasn’t particularly a fan of sweet drinks, but I appreciated the gesture.

Ben tossed his own back fast and had another two in quick succession.

“Would it be easier if I just called mommy now?” I asked in my sweetest, most condescending tone.

“No. You wanted this, you got it. Come on, Andre, it’s time.”

Andre laughed. “If you’re ready, I am.”

I followed them into Andre’s bedroom. Andre glanced at me a few times while he lit candles, his gaze curious. I kept giving him the same sly smile even though I was suddenly nervous.

The reality of it all was starting to sink in. I was about to blackmail my own stepbrother into letting this guy nail him in front of me. I knew he wanted it, and I really, really wanted to see it. Yet it sat wrong somehow. Sure, my stepbrother was a jerk and probably deserved it on some level, but this was the same guy I’d grown up with—the same guy I’d reluctantly spent the last ten Christmases with, both of us trying to one-up the other on the worst gift ever.

Ben glared at me the entire time. Finally Andre whispered something to him and he calmed. The looming shape of Andre approached with a chair. “Sit here, Kat,” he said. “And if you’re gonna watch us get naked, I think it’s only fair if you’re naked, too. What d’you say?”

He lifted the hem of his t-shirt right in front of me and smiled as he pulled it over his head and peeled the fabric down his thick arms. I eyed his pecs and licked my lips. He had the letters of one of the Black fraternities on campus literally branded into his left pec. I knew tattoos hurt. I had a few of my own in strategic spots my dad would never see, but I couldn’t imagine actually being branded like that. The idea that he was tough enough to withstand it made me all the more eager to watch him nail Ben.

Then he unfastened his jeans and I stood mesmerized, waiting for the reveal. He paused with his zipper half down and raised his hand, making a little “get on with it” gesture at me.

“Jesus, Andre, can we just get this over with?” Ben shot from behind Andre. He was standing by the bed with his arms crossed over his chest looking even more anxious than before.

“Hold tight, baby,” he said without removing his gaze from me. “I just want to make sure the experience is worth it for her. Less likelihood of her reneging, right?” His smile widened at me. “Now, if you want to see more of us, we need to see more of you,” he said in an even deeper voice that somehow managed to vibrate from my eardrums all the way to my clit.

Without a word, I nodded and unbuttoned my shirt. My face heated under Andre’s gaze and I was grateful for the dim candlelight in the room to cover up my embarrassment. I wasn’t exactly an exhibitionist and having two pairs of male eyes observe the proceedings was completely alien to me. Particularly when one was Ben.

When I got my shirt off and went for the button of my jeans, Andre resumed his own disrobing.

“Wait,” I said, before he could continue. “It’s not quite fair for him to still have his clothes on.”

Andre gave me a sly smile, then moved to my stepbrother’s side and began undressing him. He tugged Ben’s shirt over his head, sliding his hands over Ben’s tight stomach in the process. Ben was apparently no slouch when it came to working out. He looked nicer than I imagined with his clothes off. Much nicer when Andre pushed his pants down and I got an eyeful of Ben’s already hard cock.

The sight made my mouth water and I swallowed. I should not be attracted to the sight of my stepbrother’s hard dick. I forced my eyes back to Andre, suddenly uncertain about my entire plan.

“He’s got a nice one, doesn’t he?” Andre said. “Tastes as good as it looks.”

“Jesus, man,” Ben shot at Andre. “She’s my stepsister. Don’t talk about my dick, all right?”

Andre chuckled. “It isn’t a lie. And I think she likes it anyway. Isn’t that true, Kitty Kat?”

I scrambled for a coherent response. Finally I chose to affect vague interest. I raised an eyebrow, looked pointedly at Ben’s hard dick that I kind of really wanted to rub my tongue on, and said, “It’ll do, I guess.”

“Will it do enough to entertain you while I fuck him?”

I tore my eyes away from Ben’s cock and stared at Andre. “What?”

“You want to watch me fuck him in the ass, right? But I want to watch you jerk him off while I do it. Or let him fuck you. Your choice.”

Ben and I both made sounds of intense displeasure. “Fuck that last part. Fuck all of it,” Ben said. “She wants to watch…that’s all she’s doing.”

Andre made a soft “tsk tsk” with is tongue. “Baby, if you want to keep getting my cock I really need to see this.”

The absolute depravity of the idea shocked me, but at the same time my pussy ached for it to actually happen. I was close to saying yes, but I wasn’t sure Ben was yet.

“Fine. I’ll…” I had a hard time saying it. Mostly because I was conflicted about the options I was given. It wasn’t about Ben…but that cock. He had a really beautiful cock. I think I might’ve been in love. It was thick where the base nestled in the coarse gold curls, and curved in a perfect arc. I’d had no idea he wasn’t circumcised, but that made it all the more beautiful. His foreskin wrapped around the head, with just enough of his tip showing that I could see the bead of moisture clinging to him. I imagined myself licking him until he begged me to let him shove his cock into me.

“I want him to fuck me.” My entire torso heated with the confession, but I kept my eyes on Ben just to see how he reacted.

“What the fuck?”

“What? Are you afraid of me?” I asked, point blank. Ben and I locked eyes. His pretty blues looked terrified, but the rest of his body told a different story when I gave it a slow once-over. His cock was hard, a rivulet of moisture dripping from his tip and creeping down the underside. His nipples were as hard as mine were, too. I wanted to suck on all of him. Goddamn him for being my stepbrother. If he hadn’t been, I’d probably already have had him.

“No…” he said. He sounded uncertain.

“He’s scared he’ll like it,” Andre interjected.

“All the better if he does,” I said. Blackmail was blackmail and suddenly the idea held even more weight than before. Ben’s uncertainty spurred me on, but it worried me a little that Andre was so enthusiastic about the whole thing. Still, I got into the game of torturing Ben. It helped that Andre’s voice was the thing spurring me on. Every time he spoke, the low cadence of it made my nipples tingle.

“Take off your bra, Kat,” Andre said.

His voice had me too enthralled not to follow his command.

My full breasts sprang free with a twitch of my fingers at my back and I let the bra slip off my arms. When I looked up, Ben was eyeing me like he might eat me. Christ, did the sight of my body actually turn him on? Should I be disturbed by that? I didn’t even care if he’d tell my dad about the tattoo of a dragon I had that swirled darkly around one breast. It was too big to deny, yet he didn’t say a word or react in any way aside from a twitch of his cock.

It took a nudge from Andre for Ben to tear his eyes off me. As strange as the entire moment had felt, I was a little sad he stopped looking. It seemed like the first time he’d ever actually seen me since we’d met a decade ago when our parents started dating.

“You’re hard for her, huh? Your stepsister’s pretty tits do it for you more than I do?” Andre asked with mock offense. He looked back at me with a grin. “Why don’t you finish getting undressed, then come over here and get a feel of him?” Andre said. As if in illustration, he cupped Ben’s balls and then gave his cock a long, languid stroke.

I kicked off my boots and shimmied out of my jeans and panties. I’d started this demented little game, and damn if seeing Ben squirm didn’t get me hot.

Ben’s mouth fell open and his eyes widened in surprise as I approached. I’d seen him do the same thing when we watched movies together as kids. I always found it adorable that such a total hottie like him was affected the way he was by those moments. This was a little different, though.

“You’re not actually going to…” he backed up but Andre was behind him preventing his escape.

“Oh, you bet I am,” I said.

Andre removed his hand from Ben’s cock and I reached out. Ben’s hips twitched backward, but Andre grabbed him tightly and held him, whispering in his ear. “You want this as much as you wanted me. Just admit it.”

I had the strangest urge to make gentle cooing sounds to calm him, then remembered that was the last thing I wanted. The more agitated he became, the more fun it would be for me. So I shifted even closer until my nipples brushed his chest and I could gaze up into his eyes while I continued the sweet torture. My nipples tingled deliciously at the contact and my hands itched to touch him even more. The loud thrum of my pulse in my ears made it harder to focus now, but this was absolutely already happening. I was about to touch my stepbrother’s cock and I loved it.

“Oh, God, Kat,” he practically moaned the words when I cupped his balls with my hand. I followed the same slow stroke that Andre had done, except I drew it out, squeezed a little tighter, and then let my thumb swirl around his tip, spreading the moisture.

He made a little strangled noise in his throat and gazed down at me like I might be the most incredible thing he’d ever seen. He looked at me like he’d looked at the image of a constellation magnified through the observatory telescope to see the utmost detail. The love of astronomy was one of the few things we had in common. I almost wanted to tell him I wasn’t Andromeda, so he could close his mouth. The sight of his tongue slipping over his lips when his gaze drifted to my pussy made me shiver.

Cool air from a draft tickled across the bare skin that I’d religiously waxed ever since it started growing. I hated having hair there. But the thing I knew Ben fixated on was the tattoo that I had in place of a bush.

That had been a fun day, followed by an incredibly satisfying fuck with the tattoo artist. He’d nailed me from behind, ‘to avoid irritating the area’. I didn’t give a shit. He was a hot guy, but anonymous sex is anonymous sex. Not having to look in his eyes when he came was preferable considering I barely knew his name.

Watching Ben’s reaction while he stared at my pussy was mesmerizing.

“Do you want to lick her?” Andre asked.

Ben seemed to think a moment. Thankfully… I didn’t know the answer either. Not anymore.

Then he licked his lips and nodded his head very slowly. “Like you wouldn’t fucking believe,” he said.

“What?” I blurted it out without thinking. “You want to…?”

Ben’s face twisted in an irritated grimace. “Jesus, Kat. Will you let me love you for once?”

His words left me numb. I couldn’t not think about what they meant. I just stood there, stunned, while my stepbrother knelt between my thighs. He didn’t just drop to his knees, though. He raised his hands and cupped my breasts first, then kind of ~melted~ down my body with his mouth kissing and licking the entire way and his hands sliding down my sides until they reached around and squeezed my ass.

Each bit of warm contact made it painfully clear to me that somehow my plan was going to hell. I had no idea how to rein it back in, or even if I wanted to.