Title: Delia Ketchum – Arrested Roleplay!
Fandom/X-Over: Pokémon
Character(s)/Pairing: Detective Looker x Delia Ketchum
Bondage Level: Medium
Equipment Used: Handcuffs, ankle cuffs, ballgag, rope, short-sleeved orange prison jumpsuit, basin of water
Extra Actions: Fingering, Blowjob, Groping, Spanking, Cop-Criminal roleplay, water play
Sex type: Vaginal
Sex Position: Face-Off
Plot:

A slow day at the International Police headquarters allows Looker to have a visit from his secret lover, Delia. The two decide to use the cells for their own kinky roleplay.

It was a slow day at the International Police Headquarters. Many known criminals were either in hiding or in prison, no legendary Pokémon going on a rampage...It was rather quiet with nothing to do but simple paperwork.

Something that the only occupant in the office was not enjoying one bit.

The occupant was a man in his early 40s, with short black hair and stern brown eyes. He had a moderately lean and muscular build, akin to that of a tack runner. He was dressed in a basic white dress shirt with a light, purple tie on it, black slacks and dress shoes. On his chair was a brown trench coat.

This was detective Looker, one of the top agents of the agency and right now, he was hunched over his desk finishing the last bit of paperwork.

"And that is the last of the reports done. Detective Ketchum has been doing well with putting these criminals behind bars."

It had been a harrowing few months for the police. Ever since the Inter-Region Criminal Trainer Laws were enacted, there was a lot of female trainers out there that had a lot of skeletons in their closets from known co-coordinators to top battlers. As such, they were arrested and sent to prison to pay for their crimes.

Luckily, they had a lot of capable officers on the job to help them with that. Especially, since he's in a relationship with the mother of one of his top officers.

"Hey, honey"

And speak of the devil, she has arrived.

Standing a few feet shorter than Looker, she was a beautiful 39-year-old woman with cream coloured skin, reddish brown hair done in a ponytail via a green headband. She was very beautiful with nice motherly curves all over her body, a pair of wide hips that shown she gave birth but still retained that youthful bounce, while she also had a pair of large D-cup sized breasts.

This lovely woman is Delia Ketchum, the mother of one of his officers.

"Delia!" He said with a smile as he stood up from his desk and gave her deep kiss.

When they separated, he got a good look at the outfit she had on. A red, curve hugging dress that seemed to look like it was made from latex with thin shoulder straps that revealed her cleavage, black stockings and red heels. Her face was touched up with a bit of make-up with light lip gloss, making her lips more pronounced and a bit of blush on her cheeks, giving a healthy blush.

Around her neck was a golden heart shaped locket and a visitor ID badge around her neck, the badge hanging below her large breasts.

"What are you doing here?" He asked.

"Well, I had some spare time. Ash is busy doing his duties and I got bored, so I decided to drop by for a visit. And judging by the paperwork, I say you are busy." She said with a smile.

"Yep. Had to process a lot of prisoners lately. Ever since those laws came up, you will not believe how many skeletons there are in these ladies' closets as well as the numerous crimes they have committed in the present. Head office is killing me with those reports." He said with a sigh, running his fingers through his head.

"Just glad that we have officers like your son on hand to help ease the load." He said.

"YEah. I'm just glad that he approves of our relationship." Delia said with a smile.

Ash had been a bit shocked that his mother was dating his superior. Apparently, when they met they only interacted a few times and chatted over coffee. Soon, there was a spark between them until Looker asked her out.

Ash was a bit shocked but after his dad left them and he got his job, he was worried that his mom would be lonely, so he was glad that she found someone.

"MAybe you need to take a break." Delia suggested.

"Maybe. You have any ideas?" Looker asked but he blushed a bit at Delia's naughty smile.

"Open up! This is the international police!" Looker screamed, startling Delia from her desk as she walked over to the door.

"Yes, may I help you?" She asked, getting into the roll of a 'clueless' secretary'.

Looker presented his badge. "I'm detective Looker of the International Police, we are recently conducting an investigation about data being stolen from this company. And we have a good lead on who the leak is." He said in a professional tone.

"Oh? Who is it?" Delia questioned.

Looker looked at her with a glare.

"You, Miss." He said.

"What?" Delia looked shocked.

Looker then took out a recorder as he then played it.

"Don't worry, Boss. I managed to get the data needed. Soon, we will be able to further our plans along for the big finish. Kanto won't know what hit them. Agent Delia out."

Delia began to pale at the sound of the recording.

"I...I have a good explanation for that." She said with a nervous smile.

Looker didn't seem to listen to her as he suddenly grabbed her left wrist and then slammed her against the wall, pinning it behind her back.

"OW! You're so rough!" She squealed, face turning red in arousal.

"I don't care. I want answers from you, you whore! You're under arrest!" He said as he took out a pair of steel handcuffs and locked it around her wrist before taking her other wrist and locking the cuff on it as well, pinning them behind her back.

"No! Please! I had no-MMMPH!"

Her mouth was suddenly stuffed with a bright red ball gag, which was buckled behind her head.

"I don't want to hear anything from you, right now!" He said as he then began to run his hands all over her curvy body.

Delia moaned at the touch, drool covering her gag. Soon she was forced to lay her upper body on the desk, her large breasts squished against the counter.

Looker then stretched his fingers and brought his hands on her ass, squeezing it like dough, making the MILF moan in bliss as he then started to smack it, the smacks causing ripples on her ass.

"WEll, looks like there is nothing down there." He said as he then attached the ankle cuffs to her ass.

He then hoisted her up, just as she tried to regain her bearings.

"Time for you to come with me to the station." He said with a grin, making the woman whimper behind her gag as he led her out of the office.

Soon, she was forced into the back seat of the police car, seatbelt through her chest as Looker got in and drove to the nearest station.

Delia was marched into the interrogation room, her wrists were cuffed in front of her as they were secured to the table.

Looker sat in front of the nervous woman as he removed the gag.

"Now then. I want some straight answers. What information did you give your superiors?" He demanded.

Delia looked at him with a defiant glare.

"I don't know." She replied.

Looker narrowed his eyes.

"OK. Since you won't respond the traditional way, I'm afraid I will have to get sadistic." He declared as he stood up and left.

Delia, meanwhile, smiled. Looks like the routine is going to plan. She just hoped that Looker wouldn't be too into the next part.

Looker returned with a basin of cold water on a trolley and a length of rope plus a towel. He then undid her cuffs and forced her to her feet.

"You letting me go?"

"No. I know you have information. So, I have to resort to desperate measures." He said as he turned her around.

Unwinding the rope, he took hold of her arms and forced them behind her back horizontally, making her gasp in pain as he then wrapped the rope around them, before tying it off in a tight position. Next, he flipped the rope over her shoulders, crossing it through her breasts, tying it below and above, making it seem like her breasts were bigger as he did one final knot to secure the rope into position.

"What is with the rope?" She asked, face flushed as she struggled to loosen her bonds, making her chest sway a bit.

Looker smiled at the sight, before he kicked her inner knee, making her kneel above the basin.

"To prevent you from running. Now, what did your boss wanted with the data?" He questioned.

"I don't know!" She said but Looker's eyes narrowed.

"Wrong answer." HE said as he grabbed the rope and forced her head into the basin, drowning her as her ass shook before he let her up, the woman coughing as she did.

"Will you tell me now?" He asked as she blinked the water out of her eyes.

"No!" She said.

"Bad answer." He said as he then pushed her head under the water again, bubbles forming as she struggled. She then was let up to catch her breath.

"Now will you tell me?" He asked.

"Never!"

She was shoved under the water again for a few seconds longer.

"Will you tell me now?" HE asked.

"OK! It was only a favour for my old boss! He called it in as he wanted some data from the company I was at!" She confessed.

"What was it?" Looker asked.

"I don't know!" She cried, but she was forced under water again.

"I'm not playing games! Tell me or I will keep under the water longer!" He said with a glare.

"He never told me!" She cried but was rewarded with her head under the water for her trouble. When she was let up, her tongue was out as she coughed and gasped.

"Are you willing to talk now?" He asked.

"It was for some robotics project! I didn't get the full details!" She said, scared she was about to be drowned again (even though she was turned on by the rough play.)

"Hmm...' Looker thought to himself 'There is tales of a new capture system being developed...Thank you for your hospitality, Mrs. Ketchum." He said.

"Can I go now?" She begged as Looker began to undo the rope. When they came off, red marks were all over her arms.

"Sorry, but for leaking data, I'm afraid you will be sent to the Trainer High-Security Penitentiary. If you sign a plea bargain, you may have a reduction in your sentence." He said as he presented a piece of paper and a pen, while Delia dried herself off.

"So, I sign this and I won't serve too much time?" She asked.

"If the court agrees." Looker said.

Delia read it over as she thought to herself.

"OK." She spoke in a resigned tone, signing it.

"Good.' Looker said as he took the paper back and took out the handcuffs. 'Please, turn around for your mugshot." He said as Delia did just that.

She held her breath as she felt her wrists cuffed behind her back.

"You have the right to remain silent, anything you say may be used against you, you have the right to an attorney, if you don't have an attorney, one will be appointed to you by the court of law."

He then took a pad of ink and pressed her index finger on it before sticking it onto a sheet of paper, confirming her fingerprints, before she was marched to where a measuring chart and a camera were. She was then marched in front of the height chart, where she stood directly in front of the camera lens. She then saw Looker holding a small, rectangular black plaque on a thin chain that showed the details of her: - Ketchum, Delia. Age: 39, Height: 5ft 9inch, Cup Size: D, #01133192.

Delia bowed her head as Looker placed it around her neck, the plaque hanging from her chest. Standing straight, arms behind her back, she let a motherly smile show on her face as Looker primed the camera for her mugshot.

The camera flashed as it took the first picture.

"Now face your right shoulder." HE said as Delia did just that, the next photo taken.

"Turn to the left". Delia then did just that as the camera took her form.

"Now that is settled. Time to take you to the courtroom for your sentence." He said, marching Delia off to a truck, where she was placed in the back of. Looker got into the driver's seat and drove it to her next location.

"The court finds you guilty of espionage and data fraud. As you signed a plea bargain, you shall be sentenced to seven years in prison with four years for good behaviour as per your parole. Bailiff, take this slut away!" The robe wearing Looker said as he then took off his robe to manhandle Delia out of the makeshift courtroom.

She was then sent to the final place of their roleplaying: A prison that was used as a sex dungeon.

As soon as Looker pushed her through the cell changing room, he undid her cuffs.

"Now then, strip yourself and get cleaned up." He demanded as he then showed her where the showers were.

Delia took off her clothes and placed them in the cubicles, leaving her as naked as a new born baby. She then got into the showers and started to clean herself, lathering her body with the soap and water, pouring the basin over her body. She sighed in relief as the warm water covered her rope burns.

"Now it's for the final part." She mused to herself as she finished her shower.

Once she was all dried up, she then went out to find the standard uniform for the prison.

A collar with a tag to show her crimes

A short-sleeved orange prison jumpsuit that seemed to be a size too small for her with a starch collar

And a pair of knee high black leather heeled boots.

Delia attached the collar around her neck, with the details shown on the tag.

Name: Delia Ketchum
Crime: Espionage and Data Fraud
Sentence: 7 years, 4 years for parole

Next she put on the jumpsuit, the material clinging to her curves as she zipped it up, leaving some of her cleavage to show.

Finally, she put on the boots to finish off the look.

"I see you are dressed for the occasion.' Looker said as he looked at her, rope in hand. 'Now to properly break you in." He said with a lustful grin.

"Of course." Delia said with a lustful smirk as she turned around and crossed her wrists behind her back as Looker cuffed her before leading her into the next room.

Once they were inside, Looker got to work and began to secure her arms in the same manner as before, securing them with a tight knot. He then forced her to her knees as he stood in front of her, lowering his pants to reveal his 7-inch long, 3-inch wide cock. Delia seemed to get the message as she closed her eyes and opened her mouth, allowing the meat to enter her lips, sucking it as she did. As she bobbed her head, Looker patted it, sighing in relief.

A guy like him needed this.

Soon, Delia began moving her head forward, taking in a lot more of the cock as she then began to suck even harder, essentially deepthroating him before she went back to just take in the head of the penis. She then licked the underside of his cock, even nipping and sucking at his ballsack before she went back to suck his cock.

"Yes...take it. Take it all, like the slut you are." He said with a grin as he began to thrust his cock into her mouth. Delia choked a bit, but she managed to hold it in, sucking it even harder. Delia looked at him with a lustful look and a flushed complexation on her cheeks.

Looker then took his cock out of her mouth and forced her to stand up.

"Now then, time for the final part." He said, unzipping the area where her vagina was. He then slipped his index finger into her clit, slowly pumping it as she did. Delia moaned as Looker fingered her as she felt her clit loosen up.

Keeping a good hold of her thighs, Looker then slammed her into the wall, inserting his cock into her clit and began to pump and thrust like a piston. With each thrust, the Ketchum MILF's breasts bounced each time.

"Oh, yes Detective! Fuck this criminal slut! Fuck me!" She howled in pleasure.

"You don't get to say like you enjoy it!" Looker declared as he blew steam from his nose, thrusting even harder. With each thrust, Looker and Delia began to make out, their tongues dancing with each other as Looker groped her ass, squeezing it as he did, making her moan.

Looker thrusted even faster, his cock going deeper as he continued to fuck Delia. Her breasts bounced more in her jumpsuit, wet sounds ringing in the cell.

Soon, Delia felt something in her as her inner walls clenched around the cock. Looker also felt something build up as well his cock felt pressure build in him.

"I AM CUMMING!" Looker bellowed as he then began to squirt cum into her like a fire hose, cum began to leak and drip from her clit as she yelled in lustful bliss.

With the last bits of cum done shooting into her, Looker took out his cock out of her allowing her to catch her breath.

"Wow...that was..." LOoker gasped out in exhaustion.

"You really were pent up, weren't you?" Delia asked, still shaking as she tried to maintain her balance.

"Yep. Lots of work means I don't get chances to relax often." He said, adding his shirt.

"Well, luckily I was here to give you some relief." She said with a loving smile.

"I thank you for that." The detective said with a smile.

The two shared a gentle kiss, before Delia sported a naughty expression.

"Well, I can give you more." She said and Looker smirked.

"Oh, I know. But first...' He said as he placed the prison plaque from before around her neck, the plaque hanging below her large chest 'Just to make sure you know you're my prisoner."

Delia giggled as she went to her knees and began to suck his cock again.

Looker sighed in bliss as he rubbed her head.

He definitely needed this.