Disclaimer: This story is a fan fiction of a free online story called The Kiss List by an author I like to follow. The author writes PG straight fiction (though she usually mixes in a gay chapter as well). This is my fiction about an encounter between two of the characters. All characters at 18+.
"So that means I win, right?" Jamal said with a smile. "I whopped you in all three of our dart games."
Payton glared at him. The chick did not like to lose.
"So, uh, what were the terms of our little bet again?" Jamal asked, prodding her.
"You know damn well what the terms were," Payton seethed. "30 minutes. Put them on the clock."
"Good to see you so eager, honey," Jamal said, knowing that the word 'honey' would irk Payton even more, "but first things first. I believe there the little matter of the tie up. You said you had some straps?"
Payton stormed off. Jamal enjoyed watching her go. She was cute when she was mad. Her long, silky smooth, tanned legs stood out sharply against her skin-tight red dress. Jamal's eyes wandered to her shapely ass. The fabric of the dress caressed it as she walked.
Of course, the view when Payton walked back wasn't bad either. The low-cut dress showed a lot of the skin. Her long dark brown hair cascaded over one shoulder and her exotic hazel eyes flashed dangerously. Jamal let his eyes follow the dress down until it reached Payton's waist. The dressed stopped at her mid thigh, as if teasing Jamal. Well it wouldn't be teasing him much longer. He was going to take that dress of and admire her pussy. Then he was going to fill it with his massive cock and make her beg for more.
"Well?" Payton said, holding the straps in one hand and planting her other hand on her hip. "Are you going to do this or do I have to?"
"It would be my great pleasure," Jamal said. "Right after you slip out of that dress. In front of me, if you please."
Payton rolled her eyes and glanced at the clock. "Fine. Your time has started," she said.
Payton reached behind her back and unzipped her dress zipper. She wiggled her ass back and forth and then slid the dress down her body. Her nipples appeared first. They were perky. Then Jamal got a look at her breasts free from the constraints of the dress. They were full and beautiful and clung to her svelte body. Her skin gleamed with a youthful and healthy glow. As the dress fell down her body Jamal saw her flat stomach, toned with a hint of ab definition. And then the pussy in all its glory. Payton was perfectly waxed and tanned down there. Her pussy looked small and tight. Well, in time Jamal would change that.
"Good," Jamal said, unable to restrain his excitement anymore. Now go to the chair, if you please. Just bend over the chair."
Payton gave Jamal one last defiant look and then did as she was told. She bent of the cushioned living-room chair so that her head rested on the seat cushion and he ass hung in the air.
Jamal picked up the straps that Payton had dropped and tightened them around her wrists. He tied the ends of the straps to tiny leg supports on the opposite end of the chair so that her arms were slightly apart and she would not be able to undo her wrists. Then he tightened the other straps around her ankles and tied them to the leg supports closet to her. He couldn't help but admire her small, muscular calves as he did. When he stood up he let his hand trail up her legs and over her backside.
Payton shivered slightly at the sensation. "Remember our deal," she warned. "You get the remainder of the time to try to use only your cock to make me say the safe words. Your little cock. You can't use any other body part and I can try to get free. It's not my fault if you haven't tied me well enough."
"And as soon as you say the safe word I will let you go," Jamal promised. "What were the words again?"
"You know what they are, you ass," Payton said. "'Jamal's got a big cock.' Enjoy that, because you won't be hearing them again. And when you are unable to make me say them - and I do mean when, not if - I get to play my own little tie up game with you. Then I will show you how to fuck someone."
"Whatever you say," Jamal said. He knew that wasn't going to happen. His enormous young cock was already straining at his pants. She was going to say the safe words as soon as she saw it. Well, better to start somewhere she couldn't see it first so he would get a bit of use out of it before she capitulated.
"I just need to lube you up a bit first, honey," Jamal said. He grabbed the lube and squirted it liberally into his palm. He rubbed it over his fingers and then softly and slowly massaged it into her ass crack with his fingers. Her beautiful ass crack. Pressed the tips of two of his fingers against her anus, more as a warning than to lube it up. He wanted her to think about what was coming.
"Come on, that's enough," Payton said. She sounded determined but Jamal thought he detected a hint of trepidation in her voice. "No more hands. Just penis."
"That's what I like to hear," Jamal said. He dropped his pants, tugged off his shirt, rubbed some more lube on his cock, and stood behind her and rested his large hands on either sides of her hips. And then he pressed his cock gently between her ass cheeks. "Do you feel that?" he said in a soft voice as she instinctively tried to pull away. "I want this to be real slow. Then you'll understand why man is always dominant."
He slowly pushed his hips forward. His penis slid through his ass crack. He pulled her cheeks apart gently and pressed the tip of his cock against her anus. He felt some resistance there. This was a virgin asshole he was dealing with.
He began moving his hips back and forth and then, with a big push, penetrated her anus. He heard Payton let out a grunt.
"Did I hear something?" Jamal asked innocently.
"No," Payton grunted through clenched teeth.
"If you're sure," Jamal said. Well, that was the green light then. He rammed his hips into Payton's ass and his massive cock exploded into her anus.
"Ahhh!" Payton screamed.
Jamal laughed. "I told you it was big," he said. He started ramming his cock in and out of her anus faster and faster. He loved the feel of it clenched tightly around his dick. He enjoyed reflecting that he was the first one there, charting new territory. Now any guy that came after him would be getting his sloppy seconds.
Jamal continued ramming his cock into Payton, waiting for her surrender. It didn't come. He frowned. Maybe the girl was tougher than he had anticipated. "Not ready to give up yet?" he asked.
"What, have you started already?" Payton said.
Jamal was stunned. He had never butt fucked a girl before but he was pretty sure it was not comfortable for her, especially with his massive tool. Furious, he redoubled his efforts, ramming his cock in and out faster and faster.
And then Payton started to laugh.
"What are you doing?" Jamal demanded.
"Just laughing," Payton replied. "Your little thing tickles a bit. Is it large enough to pleasure any girl with? Or maybe you're still flaccid because you're really into boys."
"You want pleasure?" Jamal asked. "I'll give you more than you can handle." He unstrapped her legs turned her over so that she was facing up and bent backwards over the chair, and redid the straps. Her arms were now crossed at the wrists. He let his fingers wander down towards her pussy. He massaged her clit and felt her body shudder. Then he pushed his fingers between her lips and into her pussy. It was warm and moist and oh so right. He wrapped his fingers inside and outside her pussy and pinched her lips lightly. She gasped. He felt complete power over her. Right now, she had to do whatever he told her to do.
"I told you, no fingers," she said. "I don't care if they are bigger than your dick."
"I just needed to loosen you up a bit so I could get my dick in," Jamal said confidently. He lined up his cock in front of her cunt and then eased his way in. He did it as slowly as he could so that she would feel every sensation. She shuddered again and he knew she was enjoying it despite herself.
Jamal made love to her. He drove his cock in and out of her, loving the feel of her warm pussy closed around his tool. It felt right. His cock belonged in her. Her cunt was its home, its property. As Jamal continued he heard Payton begin to grunt in rhythm with him. Her lips parted slightly and she got a look of extreme pleasure on her face. He wanted to laugh. He knew his cock would dominate her in the end.
Payton was panting now and Jamal couldn't help it any longer. He needed to feel more of her. His eyes were feasting on her body and he wanted to be able to feel more of it. He spread his hands across her stomach and then let them work their way up to her breasts. He fondled her breasts. They felt soft and plump. He liked the way that they felt against his skin.
"You... can't..." Payton panted.
Jamal reached up and slid his fingers into her mouth to stop her from talking. He knew she was going to tell him to stop using his hands. Well, now she could suck on his fingers instead. "Do you taste that?" Jamal asked. "That's the taste of your vag juice. That's right, these were the fingers that were up your pussy. And your ass. How does that taste?"
Jamal saw fury flash in Payton's eyes. Aha. So she didn't like that very much. Well then he had something for her that she really wouldn't like.
Jamal slowly pulled his penis out her. It left the warmth of its home wistfully. Jamal did not linger on the thought. His penis would be back there soon. Jamal once again undid the straps and Payton's ankles and turned her around so that she was facing down.
Payton was spitting saliva out of her mouth. "That's disgusting," she said, "I..."
"Hold that thought, honey," Jamal said as he walked around the couch and knelt on the seat cushion in front of her. His cock was now directly in front of Payton's eyes, giving her a first good look at the thing. It was still glistening with her juice.
"Open up," Jamal said.
"I'm not..." Payton began.
That was all the opening Jamal needed. He rammed his cock in between her lips. The poor girl did not have a large mouth and his cock quickly filled it. Her lips opened and closed around his cock as she hurled insults at him. None were the safe words, however, so Jamal continued fucking her face. He loved the feel of her lips around his massive cock. Her lips were so pretty and had seemed so delicate and precise when she had been so cocky before and during the game. Now those perfect lips were wrapped around his cock, pleasuring him. He enjoyed the thought immensely.
He felt his balls contract. This was it. He was going to cum. That would be the ultimate domination over Payton. The thought of cum dripping out of her pretty little mouth was endlessly amusing to Jamal. She would definitely give in as soon as she got a taste of his gu. He would still finish up before relenting, though. She had pushed him this far, she was going to receive his cum.
Then she bit down on his cock head.
Jamal jumped. "Shit!" he cried. "What the hell are you doing!?"
Now, however, Payton was doing something else. She was sucking his cock.
"Well I'll be damned," Jamal said out loud. What should he made of this? She hadn't bit his cock hard, just enough to stop him from cumming. Why was she now sucking his cock? It made no sense. Unless... it suddenly occurred to Jamal. Payton was trying to take control of the situation. He couldn't let that happen, even though the she was doing a good job of sucking his cock. A very good job. He was already getting erect again. Still, he needed to be the one in charge. He started pull his cock out of her mouth.
"Oh!" he exclaimed as Payton bit down on his cock again. He quickly went limp. "Son of a bitch!" he said.
Payton was sucking Jamal's cock again. He stared at her in frustration. She had essentially trapped his cock. He could use his hands to try to pry her mouth open or something but he wasn't entirely sure that he could manage it before she bit his cock off. The one thing that he was certain of was that Payton would accuse him of cheating in their little game. Technically, nothing she was doing was against the rules.
Jamal ground his teeth but all he could was lie back and let Payton do her work. Countless times she brought him to the edge of cumming and just to clamp down on his cock until he went soft again. Jamal yelled in annoyance as the pain of blue balls built in his loins.
He had no little idea how much time passed with him being tortured this way. Probably somewhere around 10 to 15 minutes. When Payton finally slackened her jaw and opened her mouth Jamal whipped his cock out as fast as he good.
"Damn it!" he roared, finally able to express his pent up rage without fear of reprisal. Well, all she had done was prolong the inevitable. How he had a lot of cum saved up and just ready to fill her with. He was going to going to go back to her anus and ram his cock into it as many times as he could before his time was up. "You shouldn't have done that," he said. "Now I'm warmed up. I'm going to stick my cock up through your backdoor and fill you with so much cum that it's leaking out for weeks."
"I don't think so," Payton said. "Don't have a watch? You should have been keeping better track. Your 30 minutes are up.
It was impossible. Jamal looked at the clock hanging on the wall. Damn, she was right. She had penis-trapped him into wasting the rest of his time.
And then another thought occurred to Jamal as he untied the straps. He hadn't broken Payton. And that meant...
"From the look on your face," Payton said as she stood up and rubbed her wrists where the straps had been, "I take it you have just got it through your thick head that I get to do whatever I want to you. That was our deal."
Jamal suddenly felt nervous. If another girl looking like Payton had said that to him he would have been excited and horny as hell. Something about the way Payton said it and the way she looked - like a tiger that had just cornered its prey - gave him a very bad feeling.
"But let's be honest," Payton said. "You're not going to let me tie you up. You don't have the sack for that." She stared at him disdainfully.
Jamal felt a surge of anger. Perhaps it was the blue balls doing the talking, but he was annoyed and definitely not willing to let he win now.
"I can put up with anything you can," Jamal said. Payton still looked defiant. That enraged him even more. "And more," he added boastfully.
"What do you mean by more?" Payton asked.
"I, uh, well I don't know," Jamal said. He hadn't thought his words through.
"Do you mean you are tougher than I am so you can go without a safety net?" Payton prompted.
"Uh, what do you mean?" Jamal asked.
"How about agreeing to take away the safety of the safe words rule?" Payton asked. "You decide right and here and now whether you think you can handle anything I throw at you. If you think you can man up to it, I'll find some tape or something to put over your mouth. I warn you, though, you need to make the decision now, because if you revoke consent later I won't be able to understand it. Tell me know. That's what I call going without a safety blanket. Or you can just leave your man card at the door and pussy out," Payton said.
That did it. Jamal didn't think about anything else she said. He was not about to capitulate to this bitch. "Deal," he sneered. "Where do you want me?"
"Oh, I don't know," Payton said. "I hadn't really thought about it. Gee, I guess maybe the chair? I guess I don't know what I can do to boys in that position but it's all I can think of right now."
Jamal smiled. This was going to be easy. The chick had no idea what she was doing. She looked at him for a while, realize it was useless, and untie his legs to turn him over. Then he would escape and that would be it.
He walked over to the chair and bent over it so that Payton could tie him up. He was a little disconcerted by the feel of the straps on his skin and the way Payton confidently tightened them and pulled his limbs apart so that they were spread uncomfortably far apart. "Oh," she said after she had tied the last strap, "I just remembered something. I'm going to run and get it. Why don't you test the straps and make sure they're secure?"
Jamal held in his chuckle until she was gone. It was obvious that she was too inexperienced and nervous to do anything to him. She was probably just getting a glass of water or something, too insecure to admit that she was lost. He pulled against the straps to see how well she had done tying him. They were secure. Really secure. So at least she knew how to do that. She had even done a good job of how she positioned him. His limbs were just far enough apart to be uncomfortable and to prevent him from using strength and leverage against the straps. He hoped she untied them soon so he could escape.
"I'm back," Payton said sweetly as she walked back into the room. She walked up beside him so he wasn't able to look at her. Too bad, if he couldn't see her naked this was going to be boring.
"That counts against your time," Jamal said.
"Oh but honey," Payton said. "Don't you remember? We agreed to 30 minutes but we never set a time limit for you."
And then she wrapped something around Payton's neck. He heard the distinctive sound of a click and then felt some sort of strap being pulled snug around his neck.
"Wha..." Jamal began and then screamed pain as something zapped him hard in the neck. It felt sort of like a baseball bat had hit him there and left a burning sensation behind. "Fu..." he began and then felt another zap.
"You're really not going to want to say anything," he heard Payton say through the fog of his pain. "You're wearing a rather high-voltage dog collar. It reacts to the vibration of your vocal cords. As soon as you start to make any noise it will zap you. I just wanted you to get a taste for it but that you two are acquainted I'm turning up the voltage." Jamal felt her press something on his collar. "Now I strongly recommend you don't say anything," Jamal said. "I had to special order this collar. If you make even the smallest peep or grunt it will be mind-numbingly painful. I'm not entirely sure but I also think it could do permanent damage to your vocal cords. Besides, you won't be able to get out full words anyway. As soon as you start making any noise it will zap you and the pain will numb your cords."
Jamal wanted to scream at her. He wanted to swear at her and tell her exactly what he thought of her. The problem was, he couldn't think of any way to do it. He had his powers of speech taken from him before. Worst of all, he realized that no matter what she did he would not be able to make her stop. She could do whatever she wanted and even if he got hurt somehow she could have a potentially plausible excuse in court for why she didn't think he had revoked consent. At least for now, he was completely trapped.
"Oh I like this," Payton said. "A quiet man as my playtoy. I'm going to enjoy this."
Payton jerked as he felt her finger touch his thigh.
"Shhhh..." Payton said. "Remember to not make any noise." He felt the finger slide up his inner thigh. Then it poked his low-hanging ball sack. Payton had long nails and it was not a good feeling. Jamal instinctively tried to recoil but he still couldn't move. Then Payton's finger slid between Jamal's asscheeks. Jamal violently tried to jerk away at the unfamiliar sensation. What was the bitch doing? He was a man. Why was she doing anything with his ass? She just laughed. "A bit sensitive there, J," she said. She rested her fingertip on her anus and prodded it gently as if testing it. Thankfully, though, she did not penetrate his sphincter. Jamal never wanted to have to admit that he had been finger-fucked in the ass by a chick. "Yum, oh yeah, that is a fiiiine ass," Payton said as he took her hand out and gave him a sudden slap on the cheeks. Jamal bit his lower lip to keep from yelling out in anger. The bitch was going way to far. He spanked hoes, not the other way around. She was going to pay when he got out of this situation.
And then Jamal heard one of the most terrifying sounds he had ever heard before. There was a knock on the door. "Coming!" Payton called brightly.
Jamal jerked at his straps in vain. Was she actually going to answer the door? He was in broad view in the middle of the living room. Whoever was on the other side of the door would see everything. He had not agreed to any type of three-way or show.
Jamal heard the door creak open. Then, a moment later, a female voice said, "Oh nicely done! I like this one. He's stunning."
He twisted his head as far as he could to try to make out who the newcomer was. All he saw was black high heels and slim legs in dark pantyhose.
"This is my friend," Payton said to Jamal as she patted his butt fondly. "I invited her over to help out. You don't need to know her name. You can just think of her as pain and me as pleasure. Here's how this is going to work. I am going to tell you how to pleasure me. If you do a good job, my friend won't do anything to you. If you do not do a good job... well, that's where the pain comes in."
Payton sat down in the chair and straddled Jamal's head with her legs. She folded her legs around his neck and pressed her cunt right next to Jamal's mouth. "Now," she said, "use your tongue to pleasure me."
Jamal stared at the cunt in revulsion. She expected him to use his mouth? Of course he had penetrated girls countless times with my massive cock and had often used my fingers to get them warmed up but never my tongue. He always looked down on dudes who went down on their girls. Girls gave him head, not the other way around.
"Oh J," Payton said, "you shouldn't keep me waiting. Pain dear, would you get ready please? J likes plenty of lube."
Lube? Why would the chick need lube? Jamal heard liquid squirting out of a bottle. Then, to his horror, he felt a finger slide between my ass cheeks.
Jamal's eyes widened in shock and he instantly tried to clench my cheeks to stop the fingers from going any farther. It didn't work. The girl spread lube up and down his ass crack and then pressed against his hole tentatively. "Do you want me to go inside him yet?" she asked casually.
Jamal shook my head angrily. Payton just gave him an amused smile. "Hmmm..." she said. "Yeah, I think it would help get our message across. Just your fingers for now. J likes warming up."
Two fingers suddenly shot up Jamal's chute. He felt his eyes bulge and his face strain so hard it felt like he was breaking blood vessels. It was all he could do not to yell. The girl worked her fingers around in Jamal's ass. He felt her nails scraping painfully against the soft inner walls of his anus.
"That's good for now," Payton said. "Why don't you show him your toy to give him a bit of additional inspiration?"
The fingers retreated from his ass and then two hands held out something very long, wide, and black. Jamal almost had a seizure. It was an enormous dildo. Were they actually threatening to use that on him? He was a man!
"Now let's try this again," Payton said. She petted Jamal's head. "Come on J, you'll like it. Be a good boy and do as you're told. I'm going to help you learn a couple techniques. To start with, you're going to lightly flick my clit with you're tongue. The faster you can move your tongue the better. Now begin."
"Sorry," Payton said. "Can't get at it? Here, let me help." She spread her legs as wide as they would go. Her vagina flowered open in front of Jamal.
He looked down at it but couldn't bring himself to lick it.
"Ah, I think he's shy Pain," Payton said. "Help him out."
Jamal felt something hard slide between his ass cheeks. He panicked and buried his head in Payton's crotch. He stuck out his tongue and touched it to Payton's clit. It tasted warm, wet, and salty.
Payton laughed. "Good boy J. Now lick."
Jamal reluctantly began tonguing Payton's clit.
"Faster!" Payton ordered. "Really get in there."
Jamal began flicking his tongue as fast as he could.
"Mmmm. Good," Payton said after a while. "Now go slow. Use the flat of your tongue and press hard. Lots of saliva. I really want you to taste me. Your pretty mouth is going to spend so much time inside me that you are going to remember what I taste like for the rest of my life. I want you to have to compare everything else you eat to the taste of my cunt."
Jamal struggled to control his anger. The bitch was using him like a dog. He was supposed to be in command, not the chick. With the cold, hard dildo pressed lightly between his ass cheeks, waiting, he knew he couldn't disobey now. He slowed down his licking and began to press harder against her clit with his tongue. The taste of her cunt filled his mouth and the smell filled his nostrils.
"Oh yeah," Payton said. She reached down and patted his head. That was too much. Now she was petting him like a dog. Jamal wrenched his head away.
Punishment was immediate. The dildo pressed forward into Jamal's ass slowly. He opened his mouth and began to scream in pain but the collar instantly zapped him. The pain was mind-numbing. His head swirled but he was unable to drown out the sensation of the dildo pressing inexorably forward.
Payton cackled in pleasure. "Jamal Mr. Big Shot, all-around stud and star of the college football team, being impaled on a dildo like a chick. How does that feel J?"
The dildo began to slowly slide in and out of ass. The bitch behind him was slowly ass-fucking him with the thing. Jamal grimaced in agony.
"You can stop it, baby," Payton said. "Just do what I told you to do and it will be all better."
Jamal couldn't take it anymore. He buried his head in Payton's crotch and tried to do the best job he could eating her out. He licked her clit slower and harder. After a few moments she began to moan in pleasure.
"That's it," she said. "You're a natural. Now keep going. I want the taste of me to be all you can think about. Keep licking until your tongue is raw and then keep going. Mix it up every once and a while to keep it interesting"
Jamal licked and licked and licked. He did everything he could to stay interested. He tried singing the alphabet with his tongue. He went very fast and then very slow. He circled the clit and then pressed on it. He felt Payton's sex juices flow over his tongue, into his mouth, and down his chin. All he could think about what how she tasted. At the same time, the bitch behind him kept the dildo plugged into his ass. She didn't move it but just held it there expectantly as if waiting for him to mess up.
After what seemed like an eternity, Payton removed her crotch from Jamal's face and sat up. "I'm getting bored," she said. "You did well but I shouldn't have gotten bored. That's your fault. Pain?"
Suddenly the dildo started vibrating. Jamal gasped in silent agony as the vibrating got faster and faster, raping his virgin ass.
"That's good for now," Payton said after a minute. The dildo was pulled out so quickly that it made a popping sound as it came out of Jamal's ass. He had no respite, however, as he felt Payton's hands slide between his legs and fondle his balls. Then she began stroking his cock. "I'm sorry I gave you blue balls," she said. "I had to make sure that we would have this special moment. But now it's not necessary for you to have them anymore."
She began to stroke his cock. Jamal squirmed uncomfortably as the motion irritated his sensitive balls. Soon, however, it began to feel good. Jamal sighed and relaxed as Payton continued with her work. After all that teasing, it didn't take long. A moment later Jamal felt waves of pleasure and relief surge through his as cum exploded out of his tool.
"There's a good boy," Payton said soothingly as Jamal was milked dry. "Yeah, a very good boy." Jamal finished and he slumped forward, finally satisfied. The bitch had put him through hell but at least she had finally done her job.
And then Payton said something that completely horrified Jamal. "Pain, did you get all that?'
Jamal strained to look around see what she was talking about. Out of the corner of his eye he could just make out the girl called Pain holding a bowl. He realized in horror that she had used it to collect the massive load of cum he had just shot.
"Just in case there was any doubt about who is dominant here," Payton said, "I'm going to make you drink your own cum. I feel all guys should know what cum tastes like if they're going to ask their girlfriends to drink it, don't you?"
Jamal clamped his lips shut. There was no way on earth he was going to drink his own cum. A second later, however, he felt a small hall wrap itself around his balls. Payton held the bowl in front of his face. "Pain, would you please open our friend's mouth?"
Crushing pain suddenly wracked Jamal's testicles. He opened his mouth involuntarily to shout out and Payton shoved the bowl in his mouth. Jamal's own warm sticky cum flooded his mouth. Payton cackled with pleasure as Pain squeezed Jamal's testicles and rammed the dildo in and out of Jamal's ass as hard and as fast as possible.
"This is so much fun, J," Payton said. "And the night is just getting started."