First Time Stoned Sex with Brother

Author's note: This story features incest, crossdressing, infidelity, anal sex, and various other taboos. If you find any of this overly disconcerting, there's plenty of vanilla sex stories on Literotica you can read instead.

No sex involving vanilla ice cream here, though. One has to draw the line somewhere.

Still with us? Good on ya, mate!

***

How did a married straight man like me wind up wearing lacy pink lingerie, with my brother spanking me and pulling on my hair, and roughly slamming his cock deep into my ass?

Earlier, my best friend and brother, Robert, a tall handsome surfer-looking dude with sunbleached light brown hair and a wicked sense of humor, was smoking weed with me on his couch after his all-too-recent divorce, playing Truth or Dare. Then he accidentally saw the top of my lacy pink panties showing above the waistline of my jeans when I bent over to pet his Corgi, Buddy:

"Truth -- when did you become a sissy?"

"The fuck?"

"I saw those pink panties."

"Christmas gift. I gave Carina a 'gift card' to try one judgement free kink. She bought me some panties and bras, and a strap-on."

Robert raised an eyebrow. "Your wife fucked you with a strap-on while you crossdressed for her?"

"When you put it that way it sounds kinda perverted. But, hey, not gonna renege on a gift."

"Is the dildo big and black and veiny? Like the gayest dildo since Gay Came to Gaytown?"

"How'd you guess?"

My brother rolled his handsome green eyes. "Please. I've heard Carina call you Pervert Boy, for fuck's sake. Can only imagine her pet names for a commendably depraved guy like you in private." His eyes narrowed. "Waaaaiiiit a minute. Do you wear panties AND a bra for her? Every day?"

I shrugged. "Turns her on. Gets me laid. Enough with the intrusive follow up questions - my turn. Truth: why'd you and Alexis split up? Thought you made a great couple."

"Caught me cheating. Alexis didn't like giving BJs. I'd only get two or three reluctant blowjobs a year - like, Christmas and my birthday, and maybe after a big pay raise. So I found a gay guy who looovved giving straight married guys amazing, mindblowing, finger-in-the-butt-while-deepthroating blowjobs."

"How'd she find out? You confess because you felt guilty?'

"As if I'd make a rookie unforced error like that, knowing Alexis was a one-strike-and-you're-out kinda gal. But, sooner or later, no matter how careful you think you are, when you're married to a woman smarter than you... you're gonna slip up and get caught."

I took a deep toke off my brother's weed pipe, a grey skull shaped thing with the bowl in the skull's head. Held the strong hit of killer bud as long as I could, then coughed up a thin cloud of used smoke. Passed the pipe. "Sooo...?"

Robert knocked the ashes out of the pipe, then repacked it with more ganja. Took a leisurely toke, the kind you take when you're already buzzing and mellow and too laid back to rush getting higher. He ruefully shook his head, belatedly answering my follow up Truth question. "I forgot to delete one gotdamn text exchange lining up a 'date' with my BJ guy. Aaaand... soo busted." He shook his head ruefully. "Probably shouldn't have password 'protected' my phone with the dog's name."

"You still getting blowjobs from him?"

"Nah. I told him about how Alexis and I were fighting over the divorce. Called me a drama queen, and bailed. Said there was an endless supply of other..." Robert put finger air quotes around the next ironically drawled word, "...'straight'... married guys he could enjoy servicing. Sooo... now I'm horny as fuck all the time."

I nodded sympathetically. I kinda missed Alexis. She was a cool person, and she * had * gotten along great with my brother, until his testosterone-poisoning-induced BJ dalliances fucked it all up.

"My turn," Robert said. "Dare: undress and show me your lingerie."

I coughed in surprise, wasting the hit of chronic I'd just sucked out of the pipe. "Seriously? You going there?"

"You wanna forfeit the game? Like you always do when shite gets real?"

Fuck it, I thought. Wanna beat my brother at Truth or Dare for once.

I stood up and undressed down to panties and bra, feeling a bit shy.

Robert took another hit of his dank pakalolo, his eyelids sleepily lowered, looking super fucked-up. Blew a series of perfect smoke rings. "Fuuuck, you're way hotter as a chick."

"Uh... fuck you?"

He stood up. "I'll take that Dare."

Whaaat? "Umm, that wasn't a D--"

"No takebacks. Now, turn around. Show me that booty."

No way I'm gonna do that, I slowly thought, the weed making my thoughts seriously lag what my body was doing on autopilot. Meanwhile, my traitorous body slowly turned around for my brother and wriggled my butt enticingly.

"Niiice ass." He stood behind me. Squeezed my buns.

"The fuck? Stop it."

"Dude - you Dared me." He reached around and squeezed my A-cup pecs through the thin pink fabric. "Look at me."

I turned. Gazed into his sexy green eyes.

I felt blood rush to my head. My cock twitched and stiffened.

The fuck's happening?

"You're blushing," Robert said, his voice slipping into a seductive deep bedroom rumble that made my cock tent my panties. "Wanna get on your knees? Suck cock like a good girl?"

I stared. He's kidding, right?

My brother was gently twisting my hard little nipples, sending electric jolts into my brain from the delicious mix of smooth pleasure leavened with sharp pain. Then his hands squeezed and his fingernails scratched down my firm belly and sides. Eventually one hand gently brushed his fingernails over the silky fabric barely covering my erection, while the other hand caressed my balls. He kissed my earlobe and whispered, "I can feel how horny you are."

Robert grasped my shoulders and turned me.

So to speak.

"Aaaahhhhmyyfuuuucknnnngod," I explained, as his hands did magical things to my aching naughty bits, as the Brits might say.

"I'm so horny too. Be a good girl for me and go down on me. You're certainly dressed for the occasion."

"Please. I'm not gay. And you're my fucking brother!" I belatedly realized that the tone of my voice made it sound like a faux reluctant 'yes'.

While my slow motion thoughts tried to formulate a coherent 'no', Robert's strong arms pressed down. I sunk to my knees, surprised at my submissive surrender.

"I blew up my marriage. I need backup pussy. Speaking of blowing..." He tugged his jeans and underwear to mid-thigh. His semi-erect cock popped free.

"No... I shouldn't... if Carina found out..." Ooops. Still not a 'no'.

"I won't tell." My brother put a hand on the back of my neck and pushed my lips close to his pre-cum leaking cockhead. "Just a lick. You're dressed in pink silk, and you let your wife peg you. Accept it -- you're pussy. You wanna be my bitch."

Joking, right?

I laughed nervously. Playing along with the jest: "Not if you call me 'bitch'. Maybe if you called me 'your sexy girlfriend', nicely..."

In a husky voice: "I'll take that Dare. Would my sexy girlfriend like to suck my cock and please her man?"

Robert put his hands on my blushing cheeks. He caressed them, the warmth and gentleness of the gesture turning me on. "I know you want to do it, please your boyfriend." His hardening cock touched my lips.

So horny from weed, I heard myself whisper, "OK."

My brother gently put a hand on the back of my head and pushed his cockhead between my lips. It was smooth and rubbery in texture, but hard beneath the surface softness, and radiating heat onto my lips and tongue. The drop of precum I tasted was salty and a bit sweet and yeasty, and surprisingly tasty. I sucked harder, trying to get more cum, and his cock rewarded my greedy suction.

It felt surreal. Was I really sucking my brother's dick? I'm not gay. And incest to boot? But the warmth of his cockhead, the naughtiness of breaking numerous taboos, and the submissiveness felt so good. I ran my tongue along the sensitive underside, then rapidly flicked the tip of my tongue there.

Robert moaned and bucked his hips and pushed my head about halfway down his shaft, before I wrapped a hand around his thick cylinder to stop him from deepthroating me. "Fuuuuck. Don't stop. You're reeeally good at this. Keep licking me sweetie, all the way down the shaft."

I cupped his furry balls, gently kneading them while I licked and gently slid my tongue from side to side.

"Look up at me. Do you love to suck your brother's cock?"

I looked up at his wide-open pupils. Listened to his heavy breathing. Took my hand off his shaft and slid my lips a little further down his cock, not quite gagging as the tip touched the entrance to my throat. My tongue caressed the thick shaft's underside, the same way Carina worshiped my cock.

Robert held my cheeks and tried to fuck my mouth, bucking and pressing, trying to get inside my throat. "Relax, baby. Let me in. Be a good girl." Finally my throat relaxed enough, and his dick pushed in balls deep.

It felt weird, having my sore throat full of my brother's cock. And surprisingly hot. Tears welled in my eyes from the strange fullness and the mild asphyxiation and, yes, perhaps a bit of humiliation at so readily consenting to act like a slutty girl and get shamefully used like a fucktoy with someone I grew up with.

But... it felt good, too, hot and sexy to share this intimacy, to please my best friend and brother, and smell the gorgeously musky scent wafting from his pubic hair.

"Uhhh. UNNHHH. Oh god. So close to cumming in my sexy girlfriend's mouth. Stop. Don't move. Don't make me cum yet."

I gazed into his green eyes while I pulled my panties down. I started rubbing my rock hard dick.

Disobediently, I sloooowly slid my mouth up his shaft, teasing him with my tongue as he struggled to not cum. I looked up, just his helmet inside me now. Our eyes met.

"Dare," he whispered, then roughly shoved his cock all the way inside my mouth. "Can I fuck my girlfriend's ass?"

I shouldn't, I thought. A quick blowjob to help out your horny brother is arguably just good manners, but... anal? Naw.

"You're gonna loooove having my dick buried deep inside you," Robert coaxed in that rumbly-lemme-fuck-you-so-good-baby voice, turning me on. "Did you enjoy it when Carina dressed you all girly looking, in frilly pink lingerie, and banged you with that veiny black strap-on cock?"

Yeah, I thought. That was so hot.

Robert saw the 'yes' on my face. "Gonna feel so much better with a real dick."

Meanwhile, to my surprise, I found myself nodding 'yes', a few tears running down my cheeks from gagging and having my throat stretched wide open, swallowing his invading cock.

My brother reluctantly slid his cock out of my hot wet mouth. He tugged me to my feet and moved behind me, pulling my lacy pink panties down my butt to where it formed a crease with my thighs. His prick poked the cleft of my butt cheeks, exploring. He started kissing my neck while kneading my hard pecs covered by the matching oh-so-feminine bra.

I started panting heavily, turned on despite myself.

"Mmmm," Robert said. "Like that hard dick rubbing between your cheeks?"

He nibbled on my earlobes, sending electric flashes up my spine, while his cock dry humped me. He whispered in my ear, "Bend over the couch."

Was I really going to let my brother assfuck me? It seemed like a weed-smoke-induced dream.

Robert pushed gently on the small of my back.

My big head said 'no, don't fuck up your marriage. And for fuck's sake, with your brother too?'

My little head was rock hard by now and not listening to that cockblocking killjoy. I bent over.

Robert eased off my panties and removed his jeans and underwear, then got his legs between mine. He pushed against my inner thighs with his knees, spreading my legs further apart, then suddenly lifted my left leg up so my knee was resting on the arm of the couch, my other leg on the floor. Opening me up as wide as possible, my leg on the floor wobbling a bit, off balance. I felt helpless and vulnerable in this position, legs sluttily splayed apart, awaiting penetration.

"Good girl," Robert said, as he got lube from a drawer below the ottoman. "Oh, you look so sexy bent over, waiting for your man to fuck you." I watched in a large floor to ceiling mirror on the wall to the left of me as he as he squeezed a huge squirt of lube onto his right palm and fingers.

My brother lubed up his cock and moved behind me, leaning over. His warm chest rested on my back, his cock prodding between my cheeks. He kissed my neck again, sending a thrill through me, then planted kisses down my spine and on my buttocks.

Our eyes met in the mirror. I felt a shock as a lubed finger slid down my asscrack, rubbing my opening. I gasped and moaned with pleasure, as his finger circled my hole, rubbing slick fuckgel around my tingling asshole.

Robert whispered, "Rub more lube on my dick. Get your boyfriend ready to fuck his hot, beautiful girl." He put a generous glob on my hand. I reached behind me, grasped his hard, hot cock, and coated the shaft with slickness, then stroked his stiffness. Getting him even hornier, and ready to fuck me. He moaned softly when I kneaded and expertly twisted my hand around his cockhead, paying special attention to sensitive underside of the head.

He suddenly slid a finger inside me, all the way to the knuckle.

"Ow! Unnnh... oooohhhh. Yeesss. Fuuuck!"

It hurt, but also it felt good. He fingerfucked me a while. Started bumping my prostate.

"Aaaaah," I said. "Ohmygod, do THAT again."

Electric jolts shot into my brain every time he prodded or rubbed the spot.

"Join me. Slide one of your fingers inside me. Help me stretch you out."

I reached behind and carefully eased one of my fingers inside, sliding and stroking against his finger. Fingerfucking myself. It felt odd, one finger sending sensations into my head, plus the deliciously Other feeling of another person penetrating me. Feeling like such a dirty slut having the finger version of being DP'd, like two thin cocks doing an internal ballet, each finger up my butt probing independently, mine predictable, his slyly jolting my prostate at unexpected moments and causing me to shudder and beg for more.

"Are you ready for my cock, baby?"

"It's too big," I said, unconvincingly. Teasing. Not wanting to compare his normal sized prick to the freakishly long black dildo Carina had slammed into me. Asserting her dominance in a relationship where outside the bedroom she was more submissive. Obtaining balance in the relationship via a strap-on.

"It'll fit. Be a good gurl and take it." He took his finger out, then tugged mine out too, leaving me feeling empty and wanting.

I looked over my shoulder at him, as he guided his cock to my waiting hole, and lined it up. "Gonna fuck my girlfriend. I want my hard dick deep inside you."

I looked in the mirror again, watching his face tighten as his cockhead pressed harder, the pressure building. "Nnngh," I grunted in pain. "I don't think I can take it," I lied. Flattering him.

Robert grabbed my hips for leverage and leaned slowly forward. "I'll take that Dare. Ooooohhhh, your hole feels so good against my cock."

"Aaaaah," I said, and then his cockhead popped in. I grunted and breathed hard, watching in the mirror as my brother's face scrunched up with pleasure.

"Gonna fuck your tight ass."

"Please. Go slow."

"Ohmygod. Sooo good. I love fucking you."

I groaned with pain and, yes, building pleasure at the naughtiness, the taboo acts. Watched Robert's knuckles whiten as he grasped my hips harder and slowly forced his cock deeper into my ass, until he was buried to the hilt.

Suddenly, he playfully spanked my butt.

"Ow! The f--"

He slapped the other cheek, perhaps harder than warranted, considering. "Take it, bitch." His other hand grabbed a handful of my hair, yanking back hard enough that I almost lost balance with the one leg I had anchored to the floor. "Gonna spank your naughty ass and pull your hair. Make you my woman. Make you my slut."

I felt I should object to this rough treatment, except for the thrill and excitement, and, yes, joy, I felt getting so thoroughly dominated. It felt even hotter than when Carina took me the same way, spanking and yanking my hair and calling me 'my sexy slutty little bitch,' in her normally sweet and demure voice that I could listen to for hours, a voice like an angel.

While I went down that mental rabbit hole, Robert was pumping and jackhammering my ass, while roughly slapping my cheeks and tugging my head back. I surrendered to thrilling danger, pain melting into pleasure, giving my ass to my brother's hard shaft.

Meanwhile, a cold, ruthlessly realistic part of my head was wondering how I was going to hide or explain my abused reddened butt to Carina -- while the momentarily more dominant, sensually reckless part of my brain reveled in this crazy fucked-up NOW, future be damned.

It seemed surreal -- how did a married straight man like me wind up getting so roughly dominated by both my wife and my brother?

Am I that much of a submissive bottom slut?

I grabbed more lube and stroked my cock, almost ready to spurt my cum from the magnificent abuse.

Robert shifted the hand that had been spanking me to my shoulder, getting more leverage, bucking for dangerous penetration. "Clench your assring around my shaft, then release. Oh. Yeah. Keep doing that. Squeeze my cock with your hole."

"Fuck," I said. Redundantly.

"Does my hot, sexy girlfriend want me to cum in her sweet ass?"

"No," I said in a high pitched girly voice, teasing. "Oh, please don't cum in my butt!"

"Yeah? Too bad. You're gonna take my cum deep inside your slutty hole." I saw Robert grimacing, trying to hold off. "Can I fuck you again? Tomorrow?" He plunged repeatedly into me, his upper thighs slapping against my ass with each thrust, his balls teasing my taint.

I moaned as I felt my own orgasm build from the dual pleasure of my hand stroking my cock, and his dick rubbing and sliding and filling my ass. "Maybe."

"Maybe? Fuck that. You're mine." He pounded my ass, not caring if it hurt. But the initial pain was morphing into an uncomfortable but exciting fullness which I was beginning to crave, with periodic jolting ecstasy when he banged my prostate.

Not that he'd been particularly gentle before, but now he was ensconced in the utter selfishness of a man whose sperm were raging in his balls, urging him to obey the primal need to let those tiny soldiers rampage free to procreate. Futilely, in this case.

My brother ripped me out of this latest mental rabbit hole as he shouted, "Aaaaah. Ohmygod, I'm cumming. Feels so good. Take my cock." He bucked against me, riding waves of pleasure, shooting ropes of cum inside.

He emptied himself deep inside in my butt, hot spurt after spurt, gasping for air, his hot and sweaty chest heaving against my back. He reached around and grabbed my dick, pumping it.

"Ohhhh. Unnnhhhh." My sperm spurted on the couch, cumming harder than I'd ever cum in my life.

Afterward, Robert lay on me, his heart pounding against my back, while his cock softened and slid out of my butt. He stroked my hair, kissed my shoulder blade, and whispered, "So exciting. I love fucking you. Glad you're my girlfriend."

I lay there, post-orgasm sleepiness seeping in, wondering if the dreaded post-nut clarity was gonna kick in. Make me feel bad for cheating on my wife... for breaking one of the biggest taboos ever...

... in the pink lingerie she'd picked out for me to wear that morning. Was this partly her fault?

I felt Robert's cum dribbling out of my ass. It felt really sexy, having part of my best friend and brother deep inside me.

I thought, should I tell Carina about this, risk getting divorced?