A First Date With An Emo Cutie : Part – 2

James couldn’t believe this was happening. Waves of intense pleasure and a rising orgasm penetrated his thoughts. The idea of being a captive to a woman he’s been on one date with and her strange boyfriend should have sounded horrible. But Vicki was just so goddamn hot! And she really knew how to drive him wild!


He could feel an orgasm coming, and just as he reached the moment before climax, she stopped and took her hands off his cock. “MMM!? Mmm?”

“Aww.” Vicki made a pouting face to mock James. “Little bitch wanted to cum, huh? Not yet. You’ll have to wait for Charlie and whatever he wants to do with you.”

Vicki let a large glob of saliva drip from her mouth onto a finger. Using her improvised lubricant, she slipped the finger into James’ ass. James was no stranger to anal play, so it went in quite easy. “Mmmmm…”

James’ whimpers and moans would only become more constant as Vicki continued to tease his cock and slipped a second finger into his ass, finding all the spots that drove him crazy. Her skill was unmistakable. This girl was going to continue tormenting him like this, and James didn’t know for how long. He pressed his eyes shut and tried to simply live in pleasure.

It worked a treat, as he soon found himself on the brink of orgasm once more. When he was just on the edge, she stopped. James whined into the panty and tape gag as his body came just close enough to orgasm to push a small glob of cum out of the head of his cock, which dribbled onto his stomach.

“Aww, poor baby. I’m making your pretty little cock cry.”

Vicki’s taunts and laughs made him feel even more helpless and aroused. He opened his eyes again and looked at her with a pleading expression. Vicki scooped up the large drop of cum with one gloved finger and put it in her mouth, sucking the cum off and swallowing it. “Pretty good.”

A lot more time passed with Vicki teasing James until he could hardly think. Being as helpless as he was, he really didn’t have a lot of options except to try and enjoy the torture. James’ balls ached and his cock felt like it was as stiff as a marble statue. Every nerve in his body was alight with painful ecstasy. Every little movement Vicki made on his body pushed him further into a trancelike state.

Something finally did snap him out of his trance when the bedroom door opened and another person stepped inside. Being driven as insane with pleasure as he was, James couldn’t get the greatest look at the newcomer, but he assumed that this was Charlie. He certainly looked like he could be Vicki’s boyfriend, with piercings, tattoos, and dyed and teased hair.

Sure enough, Vicki greeted him accordingly when she noticed him enter. “Hey, sweetie!”

“Whoa. He looks so much cuter than the pictures you showed me.” James could barely understand what was happening around him, but he still felt himself blush at the compliment.

Vicki laughed. “It’s probably the duct tape and the helpless look he’s got on, plus the fact that I’ve got my fingers up his ass.”

Charlie leaned in to get a closer look at James. The two made eye contact, with James giving him what must have been the most pathetic pleading facial expression ever. He certainly acted like he’d seen the most pathetic thing ever, the way he chuckled slightly before planting a small kiss on the tape on James’ lips. “Mmmm…”

Charlie laughed again. “You got him all worked up, Vicki. That’s so mean! He cum yet?”

“Nope! I wasn’t planning on letting him tonight. But he looks so pathetic, maybe I should let him cum after all.”

James felt hopeful that she wasn’t just teasing him with that, but after he let out an excited moan in response to it, she laughed sharply. “I’m fucking with you, bitch. Tonight’s about my pleasure and Charlie’s pleasure. Yours…” Vicki squeezed James’ swollen balls a bit too hard, causing him to yelp in pain, “is nothing to me.”

“Speaking of which, did you cum yet?”

“Once. Bitch boy here has great tongue technique. Not even close to satisfied, though.”

She extracted her fingers from his ass and let go of his cock. James felt like a heavy weight had been lifted off him. He was still so horny he couldn’t process anything properly, however. He took a few seconds to gather himself back together mentally. By the time he did, he noticed that Vicki had her arms wrapped around Charlie, and the two were making out.

He let out another long whimper. Although he couldn’t speak, he knew it was obvious to them that he was jealous of Charlie. He’d gotten a taste of Vicki’s kiss and was in love. But now, instead of a tongue, he had panties, and instead of her soft lips, he had a strip of duct tape.

Vicki pulled Charlie’s shirt off him and started undoing his belt and pants, all the while keeping in contact with his lips. Once she’d undone his pants, she dropped to her knees, pulling them down with her and revealing Charlie’s hard cock. It was longer than James’, but not by a whole lot. Still, it was a noticeable enough size difference to spark another wave of jealousy.

Her lips wrapped around the head of his cock, with her left hand stroking the base. Charlie glanced at James and smiled at how intently he was watching the blowjob. James wished so badly that Vicki would blow him like that.

Her slurps and moans increased with her speed, slowly growing over time. Her head bobbed up and down. Her left hand dropped away from his cock as she started taking it further and further down her throat with each bob. Charlie’s moans and thrusts confirmed how good the blowjob was. James whimpered again when Vicki gave a seductive look up to Charlie and let out a little moan.

“Oh, fuck, you’re really fucking… oh, shit…” Charlie’s pleasure was undeniable as Vicki’s speed reached its fastest point. It didn’t take more than a few more seconds before Charlie’s moans hit their maximum. He grabbed Vicki’s head and pushed it down his cock as far as it would go. She gagged and choked on his length before he released her and she returned to her bobbing motion.

“Oh, that’s the one, baby, oh shit!” Charlie’s whole body tensed up in orgasm. Vicki moaned in delight as her mouth was filled with his cum. “God, Vicki, you give better head than anyone on the planet, I swear it.”

Vicki swallowed the load and stood back up, her lips meeting Charlie’s once more in a passionate kiss. Charlie didn’t seem to mind the taste of cum on her breath. He kissed her back with the same fury he always had. He even started rubbing her pussy with one of his hands. These two were clearly in love and having a great time. The kiss James had gotten from Vicki had been great, but nowhere near as intense as what she did with her boyfriend.

The kiss was so intense that Charlie even pushed Vicki onto the bed right next to James. The two landed on the bed with a thud that bounced James around a little. Somehow they kept their kiss going perfectly.

“You ready, babe?” Charlie’s whispering voice was so sensual and smooth that James could only wish that he would get treated that way too. He didn’t know whether he wanted to be Charlie or Vicki more at that moment. Either sounded really good, because he was too horny to care.

“Yes!” James got even more turned on by Vicki’s horny voice. He would get to hear a lot more of it, too, as Charlie slid his cock right into Vicki’s pussy. She moaned and wrapped her arms around Charlie’s back, pulling him into her.

He pumped into her, slowly at first. James moaned and complained into his gag as the sounds of flesh on flesh filled the room. It took Charlie quite a while to get worked up to the point of orgasm due to the fact that he just came in Vicki’s mouth a few minutes earlier.

James just watched helplessly as the emo queen of his dreams got railed by a guy who, by his estimation, was cuter than himself. Vicki was having the time of her life, casting looks over at James while getting pounded. James could swear she must have been exaggerating her moans and grunts just to make him even more jealous.

As Vicki came, she screamed out loud and long in a way that made James’ tortured cock throb. “Fuck, fuck, fuck, Charlie, oh my god, yes!”

Her noises were clearly having an effect on Charlie too, as he had an orgasm soon after too. His noises were more grunting and panting than Vicki’s moaning and screaming. When he pulled out, Vicki ran a finger along her pussy, gathering a finger full of cum and putting it in her mouth, just like she’d done with James’ cum earlier. “Charlie’s tastes better than yours, bitch.” Her laughter was loud enough to echo in the room as she sat back up.

“Are you done already?”

“I just came twice in a row, Vicki. I’ll sit it out for a little while if it’s alright with you.”

“Fuckin’ A, man. I guess bitch boy gets some loving now.”

James’ heart fluttered and he perked up at this. “Oh, yes, bitch, I can see you wanna get fucked, right? Watching Charlie pound me like that got you all jealous, right?”

James nodded furiously and pleaded into his gag. “Well, alright then. I can fuck you like that too.”

Vicki produced a large strap-on dildo from a dresser drawer. She quickly put it on and walked over to James. She slapped the thick purple rubber cock against James’ gagged face a few times and smiled at him. “Trust me, bitch, you’re going to love it.”

Feeling himself blush again, all he could do was whimper. He was so horny that he didn’t even think to try and object to Vicki fucking his ass. Instead, he let out a whine of resignation as he watched her pour lube onto her implement.

“Oh, this should be fun.” Charlie sat down in a chair by Vicki’s dressing table, cock in hand. He stroked it lightly as he watched. It slowly grew to half of its normal stiffness in his hand.

James moaned when the head of the dildo touched his rim. His toes curled and his breath quickened. Making eye contact with Vicki, he saw a look of lust and pleasure. “Don’t worry, bitch. I promise it’ll feel really good.”

Vicki pressed forward into his ass, eliciting much louder moans than before. It didn’t take her very long to fully push her length into him. She grabbed one of his legs and lifted it up over her shoulder, using it to hold him in place as she thrusted at a medium pace. His eyes rolled back as he felt the incredible stimulation take over his body and mind.

Her pace quickening made James even more painfully desperate. He could feel his orgasm building up again, and he could only hope that Vicki would finally allow him release. His stimulation increased further when she wrapped one of her gloved hands around his cock and began jerking him quite quickly as well.

“It’s okay to cum, bitch. I’ll make sure to get every last drop out of you.”

James’ heart pounded at those words. He hoped that she wasn’t lying and that he’d really get to cum. He was so close now, and so stimulated that he couldn’t even stop moaning, or even quiet himself down a bit.

When his orgasm finally tore through his body, he screamed into the gag as his whole body convulsed. The contractions of orgasm shot rope after rope of cum from his cock all over his body, some of it dribbling down Vicki’s glove. He felt a pain in his balls as they tightened and released all that they had built up over the past hour.

However, James’ screams of ecstasy and satisfaction quickly turned to whimpers and grunts of pain as it was clear that Vicki wasn’t slowing down. Neither the speed of her strap-on in his ass nor the intensity of her play with his cock let up. James felt painfully overstimulated.

Vicki took notice of this quickly and laughed. “Our little bitch seems to think we’ll be satisfied with making him cum just that once, but I don’t think so!” Her sing-songy mocking tone made James feel even more at her mercy.

He vainly looked over to Charlie for some hint of support, but instead noticed that he was holding his phone in one hand, obviously recording what was happening, while stroking his almost fully erect cock with the other. Charlie smiled and tilted his head playfully at James’ gaze. “That first cumshot came out so good on camera. I think if we put this online, we’d get a few million views at least.”

After several more minutes of rough fucking, James approaced another orgasm. Once again, Vicki let him finish, still not slowing her pace by any amount. The second orgasm was even more painful than the first, and it seemed to last quite a bit longer too. Instead of a proper cumshot, his cum simply dribbled slowly out of his cock. His throat was starting to hurt from how hard he was screaming and moaning into his gag.

A few minutes after that, James had his third orgasm. This time, the pain somehow felt even more pleasurable than the actual pleasure. He felt like he was floating, like Vicki had somehow transported him into a realm of pure painful bliss. Another small dribble of cum trickled out of his cock, which was now completely unable to stay hard.

Giving up on stroking the limp dick, Vicki licked all of his cum off her glove. “I think bitch boy is almost out of cum. Isn’t that right, bitch?”

James couldn’t even hope to respond in the state he was in. He knew he didn’t really need to; Vicki was going to have her way with him no matter what, a thought that aroused him even further.

When his fourth orgasm came, he didn’t ejaculate. He merely groaned and arched his back while his body pulsed a few times. If it weren’t for the tape, James would have been smiling.

Vicki laughed and gave James’ balls a few playful flicks, making him whimper. “Yeah, I think bitch boy is spent. I got every last drop out, didn’t I?”

Dropping his leg, she leaned forward into him, burying her cock deep inside him while she grabbed his chin and licked the tape over his mouth.

“Mhm. Mmmmm.”

Vicki giggled and sat back up, pulling out of his ass. She admired the way it gaped for a few seconds before shrinking a bit. It was still very open, however. She pulled the gloves off her hands and tossed them aside before running a hand through her hair and chuckling.

Charlie put his phone away and brushed his hair out of his face before approaching Vicki. The two kissed for a few seconds before he whispered something in her ear. Her face lit up and she laughed. “Shit, I would’ve forgotten, babe. Thanks for the reminder!” She quickly ran out of the room.

Turning back to James, Charlie practically pounced on him. James was clearly tired from the intense fucking he’d just been on the receiving end of, so seeing Charlie this active frightened him a bit. He might actually pass out if he had to keep going.

“Don’t worry, bitch. I’m not coming for that ass tonight. I’m pretty much spent myself, although I must say, you’re probably a lot more used up than I am.” Charlie gently grabbed James’ chin with one hand and stared deep into his eyes. “God, you’re cute. You’re pretty much the perfect bitch.”

He quickly ripped the duct tape off of James’ mouth, making him cry out. By the time he regained focus from the sharp jolt of pain of the tape being ripped off, Charlie had pulled Vicki’s panties from his mouth and was now running his fingers along his lips and tongue. “Such a soft mouth, too.” Charlie bit his bottom lip. “She really knows how to pick them, huh?”

Vicki re-entered the room, but with Charlie in his face, James couldn’t see what she was doing. He could feel her grab onto his limp cock and begin to do something with it, but he couldn’t tell what. He moved his head to try and look behind Charlie and see what she was doing, but he grabbed James’ head with his hand and pressed him into a kiss.

Charlie’s lips were just as soft and delicate as Vicki’s had been, which surprised James quite a bit. He was so surprised that he forgot about whatever Vicki was doing with his dick, and instead just focused on kissing Charlie back.

“All done!” Vicki’s voice sounded excited. Charlie pulled back from the kiss and smiled wickedly, which scared James a bit. Rolling off of James and laying next to him, Charlie put one arm around James. With the other, he traced little invisible circles around James’ body, occasionally playing with or squeezing one of the boy’s nipples.

James could now see what Vicki had been doing. His cock was now seemingly imprisoned in some small metal container with a little padlock hanging off it. The way Vicki smiled at it and the way Charlie giggled about it made him very worried.

He struggled to find his ability to speak again after having it denied for so long. “Wh-wha, what is-“

“It’s a chastity cage, bitch.” Vicki jumped onto the bed on the other side of James from where Charlie was. James just responded to her with a bewildered look.

“It means your cock belongs to us now.” Charlie emphasized his words by pinching one of James’ nipples very tightly for a few seconds.

Vicki grabbed James and rolled him towards her a bit, planting another kiss on his lips. “Your poor little cock is only ever going to get hard if one of us says so.”

“She’ll probably only ever unlock you to tease you, because she’s a cruel little cunt like that.”

Vicki laughed. “Yeah, but you love me for it.”

“Of course.” Charlie started poking his fingers at James’ ass, which still hadn’t returned to its normal size from the pounding VIcki gave it. “I’ve actually got a gift of my own to give you, bitch.” He went and looked through one of Vicki’s dresser drawers.

Using the same strategy as Charlie, Vicki kissed James to keep his attention from whatever Charlie was doing. It worked rather well, as James was too focused on the taste of Vicki’s lips to notice that Charlie had already returned and was now poking at his ass again.

He certainly did take notice when Charlie plunged a large butt plug into his ass. James grunted and broke away from Vicki’s mouth. “H-hey!”

Charlie laughed at his reaction and gave his ass a light slap. “Well, I might want this ass in the morning, and it’s already delightfully broken in. No reason to let it go back to normal just yet.”

Vicki grabbed James’ cock in its cage and gently played with it a bit. She seemed very pleased by it. Charlie kept gently touching James all over while kissing his neck. It felt rather good, in fact, to be between these two. He could get used to being their bitch if it felt like this.

James kissed Vicki one more time as he closed his eyes. Drifting off to sleep, he wondered how he could have been so lucky as to end up like this.



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