The Soft Boy Prison

Chapter 10

It was Monday after work and Casper, Holly, Mark and Louise were in the gym. Holly was hosting another sparring session, this time with Mark as well as Casper.

Mark took an interest in taking part with them after Holly mentioned her and Caspers sessions while chatting in Louise's cell two days previous. Mark hadn't done any martial arts since he attended Taekwondo lessons with his brother as a child. He knew there was a lot to learn but felt motivated by Caspers encouragement.

Holly wasn't gentle on the boys. She ordered both Casper and Mark to fight her at the same time to their reluctance. They tried their best to attack and hold their ground against her but to no avail. Holly had a seemingly unlimited well of stamina coupled by several years' experience under her belt being coached by a former pro boxer she worked with at the docks before her arrest. Not to mentioned the experience she also obtained in the numerous street fights she found herself in during that time.

She pummelled Casper and Mark mercilessly on the sparring mat, none of them could land a single hit on her and often both found themselves sitting on the mat catching their breaths, violently exhausted after a round of her clobbering them. This was one such moment. Holly looked down at Casper and Mark in disapproval. She barked at them as if she were a drill instructor to cadets at a boot camp.

"C'mon! You are supposed to be men! Get up and fight! Who cares if you're out of breath! Someone trying to batter you certainly wouldn't!"

Casper looked up at her in desperation still catching his breath, sweat dripped off of his face. "Please Holly, can we call it a day yet? I'm tired of getting my arse kicked, Mark is as well. I don't think we've got any fight left in us."

"Hmph!" Pouted Holly with her boxing gloved hands on her hips. "Gimme fifty more push ups and we'll call it even."

Both the boys sighed, got into position, and started doing push ups despite their exhaustion. Louise walked over to them as Holly stood counting their reps.

"Bloody hell." Said Louise. "You're turning Soft Boy Prison into Hard Boy Prison! Even with the Provos we never got pushed like this in training. Is it not a bit much?"

"Mark and Casper have been timid and shy their whole lives." Replied Holly not taking her eyes of them.

"People walk all over them. They need confidence and a sense of self-worth so they respect themselves enough to tell someone messing with them to fuck off. Casper did with grace but it was just the tip of the iceberg. He's got a long way to go. As does Mark. If I don't push their limits, they'll never know what their truly capable of and they'll keep getting pushed about." Holly turned to face Louise.

"Is that what you want? They're our friends after all."

"I suppose, just maybe be a bit easy on the punches. There was one I saw you landed on Mark's tummy earlier that looked really sore." commented Louise.

"Well, he's gonna remember to defend it now, isn't he?"

"Heh, you're ruthless."

Louise noticed a guard walking towards them, it was Jane.

Uh oh,

she thought. She carried the neutral expression all officers had as a default.

"Good afternoon, ladies." She said.

"Hey." Replied Holly. "There a problem?"

Jane turned her gaze to the boys still doing their push ups. Mark and Casper hadn't noticed her approach, being too focused on their exercise. Casper wasn't wearing a top and sweat was dripping off his arms and hairy chest causing Jane to get slightly aroused.

"No problem, I just need to take Casper to Jannet to get his medication." Replied Jane fixated. Holly turned to look at her.

"Oh, he never mentioned he took meds." She replied. "What for?" Jane was caught off guard, the alibi didn't go that deep.

"Errm, I don't know actually. I've never asked him. I just take him to Jannet to get them and back." Jane turned back to look at him. "What is it yous are doing now?"

"A wee bit of one-on-one training, or one on two in this case. We did some weights then sparring, now finishing off with some push ups."

"I hope you're not training to fight anyone again." Said Jane.

"Nah." Smirked Holly. "Just for fitness." Casper noticed Janes boots Infront of his eyes as he pushed up to do another rep. He looked up, saw her then smiled.

"Jane!" He exclaimed with joy.

"He seems happy to see you." Laughed Louise. Jane maintained her neutral expression trying not to express her disapproval of his excitement towards her Infront of company.

"Time for your meds." Said Jane.

"Hold on, how many reps have you done?" asked Holly.

"Thirty-three" He replied, strained.

"Well, you're not leaving until you do your fifty." Said Holly. Casper looked over to Jane. she looked back at him still with her neutral expression.

"You heard the woman." She said. "Finnish your reps."

Casper was disappointed. He was completely exhausted and his arms felt like jelly with every subsequent push up he did. He was hoping Janes arrival would relieve him from the torment of Hollys gruelling training but instead she was an active participant. He reluctantly got into position once more and slowly resumed his reps.

Jane loved it. Watching Casper work out allowed her to witness more of his masculine features in action. It was a whole new side of him she'd never seen before and couldn't get enough. Mark was taking a break from his reps, his arms appeared to have given out. Knowing Holly, she wouldn't except this as an excuse and he was still far from done. However, the focus was solely on Casper. Louise began to count aloud his reps and the other women chimed in.

"Forty-three. Forty-four. Forty-five" They called in unison. Jane laughed lightly as they counted. Caspers arms were burning, his face was twisted in pain. Holly took notice and tried to encourage him.

"C'mon Casper! I bet your mums watching from heaven right now! Don't let her down. Show her the man you've become!" Casper mustered all his strength with the last five reps. He felt on the verge of buckling but held knowing he was one closer each time.

"Forty-nine.................................FIFTY!!!!!!" Casper collapsed to the floor in exhaustion. Louise, Holly and Jane all clapped and cheered for him. Even mark sitting next to him patted his back congratulating him.

"That was awesome man! Well done!" He exclaimed.

"Thanks." Replied Casper, deflated catching his breath.

"Anyhoo..." said Jane picking him off the ground. "push up boy needs his meds."

"Sound. Catch you back at Louise's mate!" said Holly as Jane and Casper walked away together pulling his uniform top back on.

Casper was excited. The best part of him and Janes meetings were how spontaneous they were, due to the circumstances. It elevated his day from typical to brilliant instantly. He tried to contain his excitement to play the part.

Jane cuffed him accordingly with his hands behind his back and feet together at the cell block entrance. She explained to him previously an inmate was only required to wear a waist chain if being escorted as part of a larger group. Solo inmates needed only to be cuffed behind their back and be in leg irons. She took him through the cellblock doors to the lift. They went down and got off at the second floor then headed to the right. It was where cellblock A was located. Casper hadn't been on this floor and didn't know his way around, though it looked the same as the corridors in the other parts of the prison. Dull, concrete, and lifeless.

They walked along a corridor for a while then went to the left round a corner then through a set of double doors. While his legs were cuffed Casper couldn't walk at a normal pace, the journey felt like it was taking forever. The silence was deafening but Casper knew it was protocol. They approached another set of double doors, this time with a big sign on the front that read: NO INMATES BEYOND THIS POINT. Jane looked behind them as they approached it then looked back ahead.

"Don't worry. No one's here right now." She said quietly.

Past the double doors was a short corridor with one door at the very end, one to the right and one to the left. Jane turned the handle to the one on the right opening it then turned on the light inside. It was a small room with a single bed, a wardrobe and a bedside table with lamp and mirror on the wall. Jane closed the door behind them, locked it then sighed in relief.

"What do you think? A bit nicer than the store cupboard."

"It's a room alright. How did you know it would be empty?" Asked Casper.

"I requested it. The use of it for me only. I arranged it on a Monday to have it just for me since it's the only shift I've a break during the day and the only time I could take you here since you wouldn't be at work. I sold it to Samantha as a place for me to rest properly before the evening shift and she granted it." Casper looked at her with hope in his eyes.

"So, are we safe here? From getting caught." Asked Casper. Jane smiled back at him.

"Completely. No one's going to bother us here."

she walked over to him, put her arms around him and looked him in the eyes. She brought her face towards his and they kissed. She reached for his buttocks and squeezed each cheek with both hands. Casper moaned sweetly closing his eyes. Jane laughed seductively.

"Hmm? What's wrong. Wasn't this the big strong man I just watched complete 50 push ups? Why is he withered into a soft boy that moans like a little slut when I squeeze his bum cheeks?"

"I can't help it." Laughed Casper playfully. "Since I've had my willy locked up, I've gotten a bit more sensitive. It's like every time your hands are on me I'm in heaven. "Jane moved one hand down his front until she rested it on his caged penis over his uniform bottoms. Casper closed his eyes again and sharply inhaled.

"Sensitive indeed." Said Jane. She moved her other hand to the back of his head and pulled it into her, pressing him against her breasts and resting her head on top of his.

"I wonder though." She continued. "If I unlocked that dick, would the sensitivity go away."

"I'm not sure." Moaned Casper.

"That wouldn't be fun. I like it when you're locked up. You're all pent up, cute and desperate. Just a toy for my enjoyment, hehe" She stroked his hair. "Maybe I'll keep you locked up today."

Caspers heart sank. He felt like he was going to cry. He wanted to cum so badly and was so relieved initially when Jane had come to take him away. He went quiet then his breaths began to quiver. He looked up at her with desperation. His voice trembling,

"Please Jane! Please let me cum! I'll do anything!" Jane felt the surge of adrenaline in her. To have him so helpless in the palm of her hand like this made her feel unbelievably powerful. A big sadistic grin widened across her face.

"Anything?" She asked.

"Anything!" Casper pleaded.

"Hmm.... Maybe if you're a good boy I'll let you cum. Men need to know their orgasms are a conditional gift his partner gifts him. My pleasure comes first understood?"

"Yes! Of course!" Exclaimed Casper! "I'll do anything for you Jane."

"Good boy." She said ruffling his hair. She stepped back from him then pulled a key from her waist belt. "Let's get those cuffs off then, or more importantly your clothes. No talking or you'll be punished."

"Yes Jane!" He said with a big grin on his face. Jane unlocked his cuffs slowly, building the tension within him further. He couldn't wait to feel her on his bare body once more. He was ready to obey her every command, whatever it may be.

Once the cuffs were off, she stepped back from him, placed the cuffs on the floor and stared at him coldly. Casper was worried. Was there something wrong? Was she annoyed with him? The last thing he wanted was his dear Jane to be upset. However, the command to be silent proved stronger than his curiosity and he could only stare back at her with a worried expression.

"Strip." She commanded suddenly.

Casper immediately and carefully took off his rubber shoes, then uniform top, bottoms, socks and finally his underwear. His naked body and caged penis were now fully visible to her. He stood with his hands at his side, her gaze still piercing him. It made him feel so worthless. In that moment he was reminded of who he was, a pathetic little thief now prisoner with no living relatives and nothing but time. A nobody. He began to feel sad.

"On your knees." The next command came from her lips coldly. Still looking at her with his lowered gaze he knelt down onto the floor and placed his hands behind his back.

"Good boy!" She said smiling back at him. She stepped towards him looking down towering over him while he looked back up at her with fear and wonder. His big blue eyes staring into hers begging for mercy. She reached into a pouch attached to her belt and pulled out a long blue strip of leather. It was a collar.

She knelt down and brought it around his neck then fastened it. The tight leather felt so good around his neck, he got a little turned on while she fastened it. When she was done, she put her fingers on his chin and tilted it up slightly, she beckoned him to look to his right. When he did, he saw himself in the mirror on the wall wearing the collar. he always fantasised about being collared by a beautiful woman. He blushed and a big grin appeared over his face, he was horny and happy.

"You like it? I took it from the canine shed. It fits you perfectly".

"I love it, how it looks and how it feels." He turned back to look at her grinning innocently. "I feel so cute."

She moved her hand up to his cheek and brushed it.

"Awww, you are. You're my wee puppy now and if you're good I'll give you an orgasm for a treat."

Casper grinned back at her with his eyes shut in delight and obedience. However, his playful daze was interrupted by Janes high heel boot abruptly pressing against his chastity cage and balls. He stiffened in shock and let out a moan of discomfort as well as pleasure. Her expression had changed from playful to sadistic instantly.

"However, if you disobey me, you'll be punished painfully and there'll be no orgasm for the little puppy. Understand?"

"Yes Jane!" He exclaimed in obedience.

"Good boy." She began to move her boot slowly in a circular motion, lightly tossing his caged penis and balls. The sight and feeling of her sexy leather boots on his cage drove him mad. Immediately the cage was tight around his dick again. He wanted it off, yet at the same time loved the torment and tightness of it. She suddenly stopped then took a step back, her heel clack echoing as she stopped, looking menacingly into his eyes from above. Casper looked back at her with love and adoration. He listened attentively to what his queen and dearest was going to ask of him now.

"Go over to the bed for me." She said. Casper turned his head towards it then began to stand up. She put her heel on his chest firmly placing him back down into the kneeling position.

"Ap ap ap! Doggies don't walk on their hind legs. They crawl."

Casper looked down and put out his hands onto the floor Infront of him. He slowly turned around and crawled over to the bed, then climbed onto it. Jane stood standing in place watching him. She laughed softly.

"Very good, now lay face up." He slumped down on the bed then rolled over facing up.

"Very Good boy." She said sweetly.

She knelt down and picked up the cuffs up off the floor then walked over to the bed. She got on top of him with one knee on either side then grabbing his wrist cuffed it to the bedpost at one corner then cuffed the other wrist to the other corner with a second pair of cuffs. She turned around, then with the leg irons, cuffed one of his ankles then passed the other end of the cuffs around a post in the middle at the end of the bed then cuffed the other ankle.

She turned around again so she was positioned directly above him and looked into his eyes with love. She moved her hands to his and interlocked their fingers together. she smiled seductively and Casper smiled back at her. He wished this moment would last forever; she looked so powerful yet sweet arching herself above him like this. There were no words to be said, the look in each other's eyes was enough. Ever since he was eleven, he'd always wanted to be handcuffed to the bed by a woman he loved. He felt so horny and helpless all cuffed up and collared like this. She knelt down and kissed him, mingling their lips and tongues together lustfully. Casper was in heaven. Jane was too. They had longed to be together again since their last encounter and now they were.

Jane pulled her mouth away from his, splitting a strain of saliva between them.

"Hold on." She insisted.

Jane removed her waist belt and threw it onto the floor. She then slumped onto her side next to him then began to unzip her boots.

"Aw, you look hot in them." Casper told her grinning. Jane laughed and put her hand on his bare chest.

"Relax. I'm gonna look hotter when I'm naked and riding you." Caspers heart jumped and he blushed bright red with excitement.

"We're gonna have sex!?" Exclaimed Casper. Jane laughed again.

"Of course! Why else do you think I brought you here. Do you not want it?"

"No! No! No! I do! I really want to, it's just I wasn't expecting it but it's a lovely surprise!" Jane looked him in the eyes sweetly.

"Have you had sex before Casper?" She asked. Casper looked down slightly embarrassed and shook his head. Janes eyebrows lifted.

"Really? What age are you?" Casper looked back up into her eyes still seemingly embarrassed.

"Twenty-six"

"Oh, you're a bit older than I thought. But it's nothing to be embarrassed about."

"How old are you Jane?" He asked.

"Twenty-nine."

"I take it you're not a virgin too?" Asked Casper.

Jane put her hand on his cheek and brushed it gently.

"Nah. But I don't care that you are. You won't be for much longer anyway." She smiled.

Casper smiled back at her excited. She moved her hand down and gently gripped his chastity cage. Casper let out a soft moan.

"However, before I unlock this willy, you'll need to make me cum."

Jane slowly removed her boots, then pencil skirt then shirt until she was only wearing her knickers and bra. His cage felt like it was going to burst open. She looked so hot towering over him almost naked. Her skin looked so smooth and soft. So elegant. Her hair hung so freely and beautifully on her bare shoulders. It was if she was a completely different person.

She pressed her crotch against his cage and began grinding against it slowly, he let out a loud moan. The teasing was driving him crazy. She began to enjoy the feeling too. She grinded her crotch carefully against his cage, she felt its warmth and how eager it was to get out. She got into a rhythm that started to feel really nice, she closed her eyes and began to moan too. Casper was in a trance watching her pleasure herself with his useless imprisoned dick. His precum oozed over her knickers and down her thighs. It was like they were having sex but not really having sex. It felt amazing, he reckoned if she kept this up he'd cum with the cage on.

He was desperate. It didn't matter to him if the cage was on or off, he wanted to cum so badly. He honed in on the sight of her sexy body and the feeling of her crotch rubbing against the cage in all its little contours. He could feel it, he was going to cum! Jane pulled away suddenly. She sat back up on the bed and smiled at him in silence. Casper's heart sank. He was so fixated on the approaching orgasm now fading away. He was a sweaty blushing horny mess. He looked back at her in distress. What happened? Why did she stop?

"Remember what I said." Said Jane breaking the silence. "If you want that cage off you'll need to make me cum."