History 3 : trapped

Part 1

Jack was wearing nothing but boxers and a pair of grey sweats as he lifted up off the floor with a grunt; coming up from a push-up "wait for me a bit longer." The gangster said with a smile.
Zhao Zi clutched his comforter against him with a nod "okay." He said nervously.
Jack repeated the action, looking to Zhao Zi again "Are you ready?"
"Yeah.." Zhao Zi said nervously once more.
Another push up, "Almost ready!"
Zhao Zi held his blanket even tighter before nodding tentatively "okay." 
After one last push-up, jack jumped to his feet "come on," his hand grabbed the comforter Zhao Zi had a hold of and tossed it off the young officer. Zhao Zi was still completely dressed and had a manga book opened and resting on his lap. Jack looked at it curiously, picking it up and then smirking "you've been researching this?" He asked, amused when he realized his boyfriend had been reading Yaoi.
Zhao Zi's face flushed red as he scrambled to grab the book "N-Not really!" He took the book and shoved it under the pillow he was sitting against - as if trying to hide it.
"Reading That won't help you," jack's voice lowered slightly "I'm more of use." The older said seductively as he straddled Zhao Zi's lap and used his hands to grasp the man's shoulders. Jack pulled the younger against him roughly, pressing his lips against Zhao Zi's.
The officer responded immediately, wrapping his arms around Jack and moving his lips in time with the gangster underling. Jack tried to go slow, wanting to savor the moment and also help his Shorty get comfortable. He let Zhao Zi's arms wrap around him as he deepened the kiss and then began to slowly lift the long sleeved green shirt keeping him from touching every inch of his boyfriend's chest.
Zhao Zi suddenly pulled back "wait!" He exclaimed, pulling his shirt back down and sitting on the edge of his bed, a startled jack kneeling behind him. "I think...we didn't close the blinds!" He said quickly, attempting to stand and run to the window.
Jack grabbed the man's left arm with both hands when he tried to escape and threw him back onto the bed, Back pressing into the mattress as Jack hovered over him with a grin. "What're you doing?!"
Jack grabbed the comforter and threw it over the two of them "this way no one can see."
Zhao Zi let out a giggle as jack began to undress him under the covers "what do you want to do?"
"I'm going to devour you!"
"No!" Zhao Zi let out another giggle.
"Don't move so much!" Jack scolded as he pulled the younger's shirt up and over Zhao Zi's head.
"That tickles!" He wiggled furiously underneath his new boyfriend.
"That's not what it said in the book just now!" Jack teased as Zhao Zi's shirt was thrown out from under the covers and onto the floor.
"Slow down!" Zhao Zi tried to protest but he let out another giggle as Jack started to kiss his bare chest. "Don't be so hasty!" His head popped out from under the covers as he squirmed around.
"You're really that ticklish?" Jack teased again before lifting up and holding the comforter over his own head, grinning "..here I come!" With that he dived back down and covered them both with the blanket again.
"J-Jack!" Zhao Zi squealed loudly, still giggling but now it was mixed with a soft moan.
Jack had turned from being playful to much more serious as he started to kiss Zhao Zi's chest and use his left hand to pinch his boyfriend's nipple. "Hmm? Didn't you want this? Shorty?"
Zhao Zi gasped when the hand that had been pinching his now erect nipple moved to cup his half hardened length. "No! I mean-."
"Don't worry. I'll be gentle. For now," with that his hand slipped into the waistband of Zhao Zi's boxers and he started to pump the man's ever hardening length. Zhao Zi was starting to loose his train of thought, unable to giggle anymore or prolong the inevitable. His head tilted up and his back arched slightly as his body subconsciously pressed into Jack's touches. "There we go," jack muttered to himself as he watched Zhao Zi crumble in his touch.
"Ah!" Zhao Zi bit his lip bashfully after he let out the loud moan. He'd masturbated thousands of times but having someone else touch him? It was a whole new sensation he didn't think was possible.
"Tch. Don't do that," Jack used his free hand to grab at Zhao Zi's chin and lower lip, forcing his mouth open so he had no choice but to let out every heavy sigh and low moan. The mobster was so bold, so unashamed of anything! Zhao Zi envied him for that, he flirted a lot but was really shy and innocent. It took him weeks to realize Jack was trying to woo him for God's sake!
"Jack," Zhao Zi said the name breathily, making said man's own bulge jump with excitement. The look on his boyfriend's face! His eyes were hooded, his cheeks were flush and he was panting jack's name - jack's!
"Yes baby?"
"It feels good." Jack had explicitly told Zhao Zi to communicate with him. He wanted to know what Zhao Zi was thinking and if he needed anything at all - wanting the young officer's first time to be special and Enjoyable.
"Good. You want me prep you?"
Prep him, Jack had gleefully explained to him what that meant earlier in the evening. "Yes. W-what do I do?"
"I'll take care of it. Turn over on your hands and knees." Jack felt a slow burn in the pit of his stomach, enjoying the sight of Zhao Zi obey his instructions. Oh he defiantly had dozens of ideas in his head for future evenings, but tonight was special. Tonight he would make sweet and sensual love to his shorty and show him just how good he could make the man feel.
Zhao Zi turned onto his hands and knees like Jack had said - grateful the man didn't mind taking the time to show him what to do and explain things to him.
"It may be cold at first, and if it hurts let me know. I'll try to be easy." Zhao Zi heard a cap open - lube - Jack said lube was the most important item to keep on hand for sex between two men. "I'll start with one finger."
"Ah!"
"Did it hurt?" Jack asked with concerned after a single slick finger was pressed into Zhao Zi.
"N-no. It just surprised me."
Jack chuckled, leaning his body to drape over Zhao Zi's as he moved his finger inside the smaller's hole. Jack started to kiss the back of Zhao Zi's neck and leaving little nips that made him shiver. "Ow!" Zhao Zi winced when Jack slipped a second finger in him. The unexpected stretching taking him by surprise.
"Sorry. Does it hurt to bad? Should I stop?"
"No! I'll be okay. It just hurts a little."
"It'll stop soon. It takes a minute. Let me know when it doesn't hurt at all." Jack was being so sweet, he always was with Zhao Zi. But tonight felt different, almost like Jack had to try to be as gentle as possible.
Which he did - Jack wasn't used to easy going sex. He was used to the rough nights he'd have with whatever fling was available. Biting, ropes, impact play, sometimes little to no prep for whoever his bottom happened to be. He didn't take his time and he was never gentle. But he couldn't be like that with his shorty - not yet at least. "Fuck -" jack looked down in surprise. He had never heard Zhao Zi curse before, and he felt a little bit of pride swell inside him knowing that, that moaned out curse was caused by him.
"Feel good now?"
"Yes, you can do it now." Zhao Zi buried his head down to bite at the bed. The burn he felt when Jack inserted a third finger was a bit more intense than the burn of two fingers.
"Don't bite down. I need you to keep talking to me shorty." Communication.
"Hurts." Zhao Zi whined softly. "It feels tight. Ah!"
"Sorry," jack Apologized, he had moved his fingers too much and it caused Zhao Zi's hole to stretch too quickly for the younger. "That's normal. I'll make you feel good again soon." Jack coaxed his fingers inside of Zhao Zi gently as he tried to push the thought of finger fucking the man with his rings on, out of his head. Another time, Jack reminded himself again.
Zhao Zi let out another whimper, but Jack could tell this one was different from the pained whimper he heard only moments ago. Now it was a whimper filled with longing, and an attempt to hold back a moan. If He'd been with anyone else, Jack would've smacked the ass he was prepping to get another whimper just like that and then order his partner to moan for him.
"You ready?" Jack asked the question again, he was trying his best to go slow but fuck was it difficult. His erection was throbbing and he desperately wanted to be buried inside his boyfriend's ass.
"I think so."
"No. Are you ready?"
"C-can you do this for a little longer?"
"As long as you want."
Jack smiled fondly, Zhao Zi had unconsciously pushed back against his fingers and hit his prostate which made him cuss loudly. "FUCK!"
"You've got quite a mouth on you tonight." Jack started to tease.
"S-stop teasing. Ah!" Zhao Zi was getting quite vocal as Jack moved his fingers at a faster pace with expertise. Jack leaned against Zhao Zi's back again so he could nuzzle his face into the man's neck and suck at the base of it. He was able to use one hand to squirt more lube into and start to jerk himself off.
"Hmm. Shit." Jack let out a breathy moan into Zhao Zi's ear, making the man's spine shiver.
"I'm ready Jack." Zhao Zi said with certainty this time, and Jack pulled his fingers from his boyfriend and sat up straight on his knees.
"Yeah?" He still wanted confirmation.
"Yes." That was all Jack needed to grab Zhao Zi's hips and pull him back.
Zhao Zi gasped, taken by surprise as his hands slipped out from under him and his face landed against the mattress. "Hey!" Zhao Zi wanted to pout but he suddenly felt the tip of Jack's erection pushing at his opened entrance. It didn't hurt at all at first, he was preped well and so the head of Jack's length slipped inside him easily. Maybe this wasn't as bad as Zhao Zi had been worried - "ow! Jack!" Zhao Zi tried to move away quickly but Jack had him held firmly in place.
"Don't move it'll hurt worse!" Jack reprimanded, pushing slowly inside the man.
"S-Stop!" Jack paused, half way inside his boyfriend when he was asked to stop. "It hurts jack..." Zhao Zi was whining again.
Fuck. Jack couldn't help it when his cock twitched, making Zhao Zi gasp at the feeling. Zhao Zi had a few tears in his eyes and the look on his face combined with the declaration of pain turned Jack on despite himself. Again he had to keep himself from playing out his fantasy of grabbing Zhao Zi by the hair and slamming into him and asking him "how about now? How bad does it hurt now?" And then fucking him roughly until Zhao Zi cam and cried out his name.
"I have to keep going sooner or later shorty. I can't make it feel good standing still as a stone."
"I know that!" That cute pout, oh how he wanted that pout around wrapped his cock. Zhao Zi already knew all of Jack's fantasies and he was intrigued by a lot of them, but he wasn't ready for them yet.
"Can I keep going?"
"Yeah...but go slow." Jack finished pushing himself into Zhao Zi, and Zhao Zi was able to take the length with only a few more whimpers of newfound pain.
"It'll feel good soon I promise. It gets easier with practice too."
Jack let out a shaky breath, damn was this hard. He couldn't wait until he could really fuck his cute and innocent boyfriend. His cock twitched again thinking about it. "Oh." Zhao zi let out the sound when he felt Jack's erection jump inside him again. "What are you thinking about?" Maybe if Jack talked to him he could move past the pain he was feeling and hurry into pure pleasure.
"I was thinking about fuxking you."
"Aren't you now?" Zhao Zi moaned quietly, biting his lip. Jack had shifted on his knees and the movement elicited a response from the younger.
"Not like this..." Jack paused. Wondering if he should tell Zhao Zi.
"Tell me. Please?"
"I was thinking about how great it would be to slam you on my cock. Watch your cute little ass bouncing off me. Fuck."
Zhao Zi's hands gripped the bed sheets, his cock twitched too at the thought. He wanted to be Jack's forever, he wanted Jack to show him everything - make him feel good in ways he couldn't even imagine. "W-what else?"
"I want to wrap my hand around you throat and shove my fingers in your mouth. Have you moan around them like a little slut." Jack started to massage his fingers against Zhao Zi's hips, trying to stay sane and not grip to tightly as he pressed against Zhao's body in order to hit the man's prostate. "Dammit Shorty. You're so cute. I want to fuck you on your back and watch your face. Your eyes hooded and your mouth open like when I was jerking you off. I want to hear you screaming. Screaming for me. I'll steal your handcuffs and cuff you to the bed so you can't move and I'll eat you up." Jack let himself slip momentarily, long enough to smack Zhao Zi's bottom and leave a pulsing red handprint.
Zhao Zi cried softly from the pain, but he was surprised when his cock dripped with pre-cum."w-what."
"Did you like that?" Jack asked with curiosity lacing his voice.
"Stung. B-but it made me..."
"Sometimes pain is nice." Jack interjected. "Want me to do it again?"
"Yes - AH." His cock twitched and a string of pre-cum shot out this time when another spank was landed. Zhao Zi was starting to shake, his knees were getting weak as he thought about what Jack had said. It scared him but it also excited him. He was to shy to admit that he'd jerked off thinking about some of the same things. He'd cuffed dozens of criminals but he wondered what it would feel like to be handcuffed himself? He'd fantasized about jack cuffing him in a cell and then having his way with the cop. His boyfriend was always so sweet to him, but he was still a mobster and had a dark side Jack didn't show him.
"Tell me what you're thinking?"
"I can't it's -" zhao Zi was going to say embarrassing - but that would sound silly coming from a man currently being fucked on his knees and about to orgasm.
"It's your turn. It's only fair. What are you thinking about me doing to you?" He whispered the question in Zhao Zi's ear. "Tell me and I'll make you cum in five seconds."
"H-handcuffs."
"What about them?" Jack straightens jack up and started to thrust in and out of Zhao Zi slowly, gingerly.
"You...for you to handcuff me in a jail cell."
"That's sounds kinky. What do I do after that?"
"T-take advantage of me."
"Like I am now?"
"N-no. Different. Ah!"
"Not yet. You have to tell me about this little fantasy my sweet little shorty has." Jack reminded as he slowed to a halt, not giving Zhao Zi the satisfaction of getting to an orgasm just yet. He needed to hear this.
"Handcuff me so I'm facing you inside the cell. A-and you hold me up in your arms and fuck Me like that. Holding me up."
"Fucking hell Shorty that sounds hot." Jack started to  move again, rewarding Zhao Zi. "You want me to fuck you standing up? Bounce you on my cock? Play cops and robbers? You into that?" Jack was goading his boyfriend, expanding on the little fantasy.
"Y-yeah. And spank me?" Zhao Zi was really trying to talk dirty like Jack could.
"Spank you? Am I the cop in this game?"
"Ah jack!" Zhao Zi moaned when he felt a thrust against his prostate. Jack knew how to edge him, make him come inches from cumming and then slow or move just enough to keep him away from the orgasm. It was almost torture, but Jack wanted to play with him and make him reveal his dirtiest secret.
"Well?"
"Yes! You're the cop and..and you have to teach me a lesson for being a criminal!"
"By spanking you?"
"Yeah, yes! I need to be spanked to learn to follow the law!"
"Hmm. What else?"
"Jack please."
"What else baby?"
Zhao Zi could melt whenever Jack called him baby. "I-" jack peered his head to see Zhao Zi's whole face was red with a blush, meaning whatever else he had to say was something the innocent little cop was too embarrassed to admit, even to his boyfriend. "I'm still handcuffed but you let me off the bars of the cell...."
"Mhmmm." Jack massaged Zhao Zi's hips again, coaxing him to continue.
"I have to take care of you...so you'll Let me go."
"How do you do that?"
"I have to suck you off. And you make me take all of your er...cock. And make me gag. But then you let me go when you finish.  Except now I don't want to go. That's when you handcuff me back to the cell to fuck me in your arms. " Zhao Zi got caught up in the moment now, spilling his entire dirty fantasy to jack. "Fuck me against the cold bars of the cell even after I cum. Remind me I'm a lowly criminal and I'm lucky to have such a caring officer like you. Whose going to set me straight and not throw me in jail. So you'll fuck me until I start to cry cause it starts to hurts. You wipe away my tears and cum inside me - telling me i look pretty like that. And then you just stand there, inside me until I start to pass out."
"S-shit." Jack didn't think Zhao Zi was going to say all that! His innocent shorty! His cute little boyfriend! Jack had no idea he was such a pervert!
"JACK!" Zhao Zi cried out, coming back to reality as he felt the gangster thrusting against his g-spot repeatedly this time. His eyes rolled back as he felt himself tip closer to an orgasm than Jack had allowed him all night.
"Louder. Please I want you screaming my name while I cum." Oh! Jack! I think I'm -" Zhao Zi collapsed onto the bed as he screamed his boyfriend's name out, no longer to shy and self conscious about the neighbors as his body shook with an orgasm. He never knew he could climax that hard. And then when he felt the warm cum that belonged to Jack fill him up his cock twitched with excitement. How could that make him feel any excitement? Just the act of being cam inside of?
Zhao Zi was panting, out of breath as he laid - collapsed against his bed as jack started to move around. How did he have any energy after that? Zhao Zi couldn't even move!
"You have to get up shorty. I need to clean us up."
"Can't. Hey!" Jack lifted him up and pressed against the elder's back. "Oh!"
Jack chuckled when Zhao Zi jumped, his ass sore when it pressed against the bed. "That's gonna hurt for a day or two. But I'll help you get used to that too." Zhao Zi smacked Jack's thigh playfully, earning him another chuckle. "Here," jack had brought out a pack of baby wipes from seemingly ruin air and stared to wipe Zhao Zi up gently.
"Huh?"
"Aftercare."
"But it wasn't rough...like that other stuff you were telling me about."
"Yeah but you still deserve to be taken care of. It was your first time after all. And even after vanilla sex you deserve to be pampered."
"You always pamper me..."
"Always will." Jack smiled, kissing Zhao Zi's neck as he continued to clean them both up. "Want a bath?"
"How do you have the energy to even move?"
"Lots of practice."
"Lots?"
Jack laughed and threw the comforter back over them. "I'm guessing you're ready to cuddle and sleep then?"
"Cuddles sound nice." Zhao Zi snuggled against Jack's toned chest.
"Who would've thought."
"Thought what?" Zhao Zi asked in a mumble, starting to fall asleep.
"My incident, pure, sweet shorty. Would be hiding such a lustful fantasy!"
"Like you don't!"Jack laughed and kissed the pout Zhao Zi gave him. "...Jack?"
"Yeah?"
"I love you."
"I love you shorty."