An Unexpected Gangbang

All characters in this story are 18 or older, and the author does not in any way condone non-consensual sex. This story is fiction and contains: rough anal, pain, humiliation and degradation, oral and nonconsent/reluctance; if you don't like these themes, please do not read or rate it. This work is purely fantasy, and any resemblance to actual persons, living or dead, or actual events is purely coincidental.

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Introduction:

Megan and Kylie, best friends and the biggest Lookout fans are hanging around the hotel they know the band is staying at after an amazing performance. Hoping to catch a glimpse of the band or even find the afterparty, they are approached by a man claiming to be their manager. After chatting with them and checking to make sure they are eighteen, he gives them a penthouse room key and says they're invited to meet Robbie.

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The elevator doors opened, and a scantily clothed girl shuffled out of our path. Her tiny maroon dress had a tear in the side that one hand was trying to hold together. Faint mascara lines ran down her cheeks, her lipstick was smeared in parts and missing in others, but the empty, tired look in her eyes was most noticeable. We brazenly stared at her as we stepped past her and then watched her wobble into the elevator. As the doors closed behind her, I swore I saw something glistening on her thigh and calf.

"That girl totally didn't have any panties," Kylie smirked as the elevator left.

"That, is like, the epitome of a walk of shame," I snickered back. Looks like other people were having fun tonight! We had arrived at the penthouse level of the hotel, with only four entries to rooms visible from the elevators. I quickly found the correct room and slid the key into the lock apprehensively. Was this too good to be true?

"Holy shit!" I exclaimed as I entered the hotel room. It was less like a hotel room and more like a huge luxury condo, including a huge city view and sunken living room.

"This can't be real!" Kylie squealed as she twirled around in the vestibule.

No one was there, but there was evidence: pillows and clothes strewn around the floor and faint music from upstairs. Did I mention there was an upstairs? Two hallways branched from the vestibule to more rooms, and a stairway with balcony overlooked the main room.

Kylie plopped down on a white couch, giggling.

"Wow! This is insane, I can't wait to meet him!!!" I joined her on the couch, adjusting my skirt to cover the top of my stockings and ensuring my top was appropriately covering my chest. I was wearing a black, draped, deep V-neck top tucked into a short, pleated black skirt to contrast my long blonde hair. Tonight, I was feeling surprisingly confident about my B-cups to go braless in such a revealing top. The black g-string that matched my thigh highs and 2-inch heels made me feel particularly slutty and definitely was contributing to my confidence tonight. Catching the band's eye was our goal tonight, at any cost.

Kylie was dressed similarly slutty in very low-rise wet look pants atop 3-inch stilettos. Her tanned midriff was bare, only a tiny black leather tube top covered her C-cups. Like myself, she was a blonde, but recently had cut it shorter and bleached it towards a silver.

"Oh my god, Kylie, I can see your thong!" I blurted out as I noticed her white thong peeking out from her low-rise black pants.

"Tell me something I don't know," Kylie responded smugly, slipping her fingers through the waistband and snapping them even higher on her hips. I couldn't believe she was trying to look even sluttier than she already did!

"You have a boyfriend!" I exclaimed, realizing her intentions might be a bit different than I had originally anticipated. I was a little worried that Robbie might be enthralled by her instead of me; she never had trouble enticing men.

"That doesn't mean shit right now," she retorted, gesturing towards the suite, "We're in the hotel room of Robbie-fucking-Jameson!"

A brief hint of anger shot through my mind as I watched her displaying her body, willing to cheat on her boyfriend if it meant sleeping with Robbie. I thought she'd be thrilled enough to meet him and keep me company, but the evening was taking a turn I didn't like.

"Hello, girls."

I jumped as I realized that Robbie was already halfway down the stairs. I could see his chest and abs glistening as he descended towards us topless, and my heart skipped a few beats. This is totally happening!

"Oh!!" we both exclaimed as he stepped off the stairs and his full body came into view. He was completely naked, and his shining cock was standing straight up against his belly. He had to be at least 8 inches, I speculated as I crossed my legs nervously.

He sauntered over to us and dropped his chiseled frame between us without ceremony, as if this was normal. I kept my gaze locked to his beautiful blue eyes for fear I wouldn't be able to stop staring at his cock if I started.

"I'm Robbie, but I'm guessing you knew that..." he grinned the most beautiful smile and extended his hand. I felt my crotch melting as I shook his hand, trying my best to ignore the meat spike between us. He introduced himself to Kylie next, who made no effort to conceal her staring at his cock.

"I'm Megan," I stammered out, "We're like, your biggest fans! Ever since you dropped Bittersweet, it was sooo good!"

"I'm glad you like my music," he responded with another disarming smile and lightly rubbed my shoulder, causing me to again shift my legs. I'm pretty sure I'm making a pool of juices on this nice couch and he's going to see it if I have to stand up, I flinched.

"So, do you girls like to party? You're both very cute!" he chatted idly while continuing to stroke my bare shoulder.

"Thanks," I murmured again before hastily adding, "We're both in college!"

Fuck, at least pretend like you can play hard to get I agonized in my head. I was putting myself out there way too quick and I knew that wasn't how you get to be the girlfriend of the lead singer of Lookout.

"Oh, that's very cool," he chatted, but my eyes grew and heart stopped as I watched Kylie lean over his lap to take his cockhead in her open mouth.

I froze as I watched her lips wrap around the gorgeous tip and slowly start sucking it. Robbie didn't even break eye contact with me as he continued, "Adelaide?"

"Yu--yes!" I spat out, not believing my friend would do such a thing in front of me. That fucking whore is in a relationship I fumed. My eyes must have belied my anger, because he gripped my arm and pulled me towards him.

"Don't worry, there's plenty to go around," he said coolly before kissing me deeply on the mouth. I sat up on my knees and kissed him deeply back, my friend still slobbering below me in his lap. It felt magical, his tongue dancing around my lips and into my mouth, and I forgot to breath for a few seconds. When he finally broke it off, I inhaled deeply and gazed into his crystalline eyes.

"Wow," he gasped, "You're really good at that."

I couldn't believe he was saying that; I didn't have much experience and clearly was no master of kissing like he was.

"You know, I've been thinking about getting back into the dating scene," he trailed off, before pulling up Kylie by her hair to kiss her fully on the mouth. She looked so hot, her lipstick already smeared a bit as she wrapped her arms around Robbie's neck to kiss him back. I didn't need to be told twice.

You've got one shot at this you slut, I chastised myself as I dove into his lap and attempted to spear my head on his veiny member. His cock tasted like Kylie's lip gloss as it filled my mouth, and I quickly gagged as it hit my tonsils. I slid up and bounced right back down, eager to please him and show I could pleasure him better than Kylie. That fucking whore had a lot more sexual experience than I did, so I was already on the back foot.

"Oh, yeah!" I heard him groan above me and felt a hand settle into my long, blonde hair. Gently wiping my hair out of my way, he wrapped it into his fist so I could blow him uninterrupted. God, he's sweet I thought as I continued to try to push my face deeper into his lap. I bottomed out about halfway, but as I did, I felt him apply pressure to the back of my head. Ok maybe not the sweetest I mused as I tried to soldier further down the shaft with his "assistance". My gag reflex kicked in and I came up gasping for air.

"You got this, babe," he encouraged before lowering my mouth back down onto the waiting pole. I felt my body temperature rise even more from his words of encouragement and tried to gag myself harder. I started to feel cool air on my butt and realized that he must have lifted up my skirt. I hope he likes what he sees, I thought as I continued to inch his cock deeper into my throat. I vaguely felt him play with my g-string, running a gentle hand up and down my asscrack. I felt goosebumps on my arms and back as he slowly crept his hand towards my exposed pussy. An involuntary moan emanated from my occupied mouth as I felt fingers penetrate me.

I couldn't tell what was happening between Kylie and Robbie but I could feel him start to fingerfuck me from behind in an effort to push my head deeper into his lap. I was starting to reach my limit and still had at least 4 inches to go. I came back up for air and found myself face to face with Kylie's defiant face. Robbie had a fist in her hair as well and coaxed us both by our 'handles' to sandwich his large girth between our mouths. This seemed a bit degrading, but I wasn't about to be outdone by Kylie, so I opened wide, pressed my tongue to his cock, and half-kissed Kylie as Robbie groaned and slid his cock in and out of the newly devised orifice.

"God, you two are so hot!" Our lips finally came together as I felt more pressure on the back of my head from Robbie that increased with the speed of his thrusts. I closed my eyes so I could pretend Kylie wouldn't see me in such a compromised position. What the fuck? I checked myself mentally, she's the slut who got us here!

"I think we should take this to the bedroom," Robbie groaned above us after a few minutes, not letting us respond as his cock continued to bridge Kylie and I.

When his grip finally released us from his constructed orifice, I nodded enthusiastically, saliva and precum dripping from my mouth. Kylie also nodded, and we rose to follow him up the stairs. As I flattened my skirt down over my thighs, I noticed Kylie's top had disappeared altogether, her breasts bouncing freely as we walked. Robbie motioned for us to walk ahead of him when we reached the stairs.

"Ladies first," he grinned and waved us by with his glistening cock. His member was truly glorious, the large purple head standing at attention against his chiseled abs. I dragged my fingernails along it gently as I walked by, trying to be seductive but also dying to feel it inside me. As I took my first step up the stairs, I felt his hand penetrate me again from behind. Ladies first indeed, I smiled as I adjusted to the intruder while continuing up.

As we reached the top of the stairs, his grip pulled me back into his chest and I found myself with Kylie wrapped in his arms. One hand was down the front of Kylie's pants and she was moaning into his embrace while I wriggled on his other. His gentle fingers were deep in my pussy and it was making me a little light-headed.

"Hey, why don't you little sexpots make yourselves comfortable in that bedroom there?" he breathed into our ears while motioning towards a door, "Let me freshen up really quick and I'll join you."

After giving us a push down the hall, he went down another, I presume to a bathroom. Some faint music and party noises accompanied us as we entered a well-furnished bedroom. Large mirrors surrounded a king-sized bed with a daybed at the foot of it.

"Megan, did you see his cock? Oh my god it is so beautiful and huuuge!" Kylie said while removing her black leather pants and readjusting her y-back thong. I could see a large wet spot on her crotch, and I knew mine looked similar underneath my skirt. I was still perturbed by her involvement in the evening so far, but that was slowly succumbing to my desire to just be penetrated by his cock. If Kylie was around when it happened, so be it; no one else seemed fazed so far.

"Alright, ladies," Robbie announced grandiosely as he slid into the room, "Who's first?"

My heart skipped a beat again as I watched Kylie collapse to her knees in front of him and start sucking his cock again. Fuck she is such a whore! I judged as I felt my crotch get wetter still. I couldn't deny she looked hot as hell, impaling her face on his crotch with reckless abandon, naked except for the white thong splitting her tanned asscheeks.

"Oh god yes," Robbie entwined his hands in her short hair and gazed towards the ceiling while meeting her mouth with thrusts from his hips. Pushing her onto her butt, he walked her to the bed and pinned her to it while continuing to fuck her mouth. I knelt next to her and tried to join in, only to have him lift me up and bend me over the bed. My legs felt weak in anticipation of finally receiving his cock. I had never had a cock close to 8 inches inside me.

Gagging and choking sounds emanated from behind me and I turned to see Robbie drag his entire length out of Kylie's throat. Whoa, she can deepthroat that monster? I have a lot to learn tonight...

My wandering thoughts snapped back to the electrifying sensation in my body as my skirt was lifted and I felt his wet meat glide up and down my pussy.

"Oh god, yes!" I moaned loudly, "Fuck me, Robbie..."

"Anytime, baby," Robbie hooted and suddenly I recognized sharp pain as he penetrated me.

"Oh, FUCK!" I screamed and my hands flew back to block his hips from going further in me. The sharp pain in my vagina was quickly overpowered by the sensation and knowledge that Robbie was fucking me. He ignored my hands and drove deeper with each slow thrust, my body agonizing through the pain but quickly mounting an orgasm. How my body was about to cum through the sharp stabbing in my crotch, I had no idea, but I wasn't going to question it. Rarely cumming from vaginal penetration, I couldn't believe I was 1. about to cum with a few seconds of penetration and 2. fucking Robbie Jameson!

"I--I'm about to cum," I whimpered quietly, a little embarrassed by how much control he seemed to have over my loins as I felt the tidal wave start to rise before the crash. I only felt fire in my pussy but knew he was starting to pick up speed behind me as his hips slapped my butt. As my first orgasm crashed through my clouded mind, I twisted off his cock onto the bed and lay there twitching.

"Attagirl!" I heard Robbie laugh as he dragged my twitching legs back off the bed and returned me to my bent position. My top was pulled off while he slapped my ass a few times, eliciting sensitive yelps from myself. I grabbed a few moments of respite to enjoy the orgasm as it permeated every inch of my body, listening to Robbie fuck Kylie's head right next to me. This guy is a stallion, I muttered as I heard Kylie gagging again.

A few moments later I felt my pussy spread and the full sensation returned as he bent over my body. The pain this time was significantly less, and I sensed my next orgasm was arriving shortly. Bent over my body, he clamped a hand over my mouth and used it to lever his cock into my waiting body harder. Was I moaning? I didn't have a chance to think about it as his persistent thrusts lit the fire again for a freight train of an orgasm to appear on the horizon.

"Huh?" I whimpered as I felt my crotch suddenly devoid of his cock. Turning around, I disappointingly watched him again use Kylie like a fleshlight while my freight train slowed down.

"Please fuck me, daddy," I whimpered loudly while wiggling my ass at him.

Laughing derisively, he gave Kylie's face a few more rough thrusts and held her there until she struggled and tears gushed down her cheeks.

"Good job!" he stated warmly as he vacated her mouth, but not before slapping her across the face. That's kinky and kinda hot I thought as I noticed my body respond to this new kind of sex. The fire in my body turned into an inferno as I felt my pussy stretched to the familiar size again. I don't know how much time or thrusts passed, but very quickly I felt the freight train come barreling through my body and my legs quivered around his cock, trying to escape the pressure on my sensitive parts. I lay there at the mercy of his cock, twitching and crying as the orgasm descended on my body again and again.

When I could coherently think and perceive the world again, I saw Kylie on her back beside me getting railed by Robbie. One hand was around her throat and she was drooling and gasping while her body bounced into the bed with each forceful thrust.

"Fucking fuuuuuck!" she gasped into the air as I saw her hips start twitching.

"There you go you little slut," Robbie growled as he leaned over her quivering body, still choking her, "Cum all over that fucking dick."

"Aggghhhhh!!!" I watched in a fascinated daze as she continued to spasm at the end of his cock until he finally let her breath, leaving her a gasping and choking mess. This didn't stop him from continuing to ravage her body, as he flipped her over and spanked her a few times before slamming back into her. After a few thrusts, he turned to me and beckoned to lay my head over the side of the bed. Unsure of the intent but eager to please, I complied. Kylie looks like she needs a break anyway.

I found Robbie's cock laying across my face from brow to chin. I could smell the scent of sex on his member as he pulled me further off the bed and pushed his cock into my mouth. Not the most comfortable blowjob position. He quickly filled my mouth with the first few inches and I gagged. The shaft and balls draped on my face didn't make it any easier, but I slavishly tried to gobble more down. He pushed deeper into my throat and I struggled to deal with the lack of air and my own gag reflex. Every deep thrust resulted in my body involuntarily trying to wriggle free, and Robbie trying to pin my body with his hands and cock.

"You almost got it, baby," I heard him grunt as tried to shovel his cock down my throat. So that's what this position is for, I frowned. My mind wanted to please him so bad but my body was just not willing to suffocate itself for him yet. I couldn't imagine what my face was starting to look like with the tears and saliva running down my cheeks that resulted from my gagging noises. A forceful thrust from him finally set his balls on my nostrils and the accomplished feeling I had faded as my breath and vision did.

"You did great!" Robbie exclaimed when he extricated his snake from my throat and left me a sobbing and coughing mess. Sensing my limit, he roughly pulled me off the bed by my neck and knelt me on the floor next to Kylie's legs. I was rewarded with quick stabs to the back of my throat, which I gladly endured over my previous arrangement. His grip on my head and hair placed my face next to Kylie's ass, and he began to alternate fucking her pussy and my mouth. My brain winced at the new post, but my pussy reawakened from the previous smothering. We're just fuckholes to him, my brain tried to caution, but the humiliation and regret just made me wetter.

I barely heard the door open behind us as Kylie howled through another orgasm and I spun around embarrassingly. Laughter and banter accompanied the bassist, drummer and another guy I didn't recognize as they walked in, all naked. They gawked at the two of us, Kylie bent over the bed quivering and myself, sitting defensively on the floor tits out, skirt a mess, and stockings somehow still on me.