The Soft Boy Prison

it was Monday again. Jane and Casper were in the staff rest quarters for their scheduled intimacy.

Casper knew this was the time and place to tell Jane about the crisis involving David Shaw and Louise's mother, if indeed he was going to tell her at all. He figured to just forget about it for the time being and enjoy the sex, then bring it up later if he decided he should.

He had Told Holly, Louise, Mark and Erin he was going to the library today to read on his own.

God forbid they go looking for me there for whatever reason

he thought.

He was unsure how he could keep coming up with these excuses. Especially since it was the same time every week. No doubt they would get suspicious sooner or later. Alas, it was another thing to consider at a later point. Right now, all he wanted to concern himself with was his beloved Jane and her beautiful body.

Though at this moment it wasn't easy, given he was naked, kneeling on the bed with his feet and hands cuffed behind his back, blindfolded and mouth taped shut. Jane had also crossed the chains of his hand cuffs and leg irons over each other, effectively hogtying him in this uncomfortable position. The feeling of all these restraints made him feel so helpless and horny. His chastity cage was tight and bursting to get loose.

Jane stood Infront of the mirror slowly undressing looking at Casper in the reflection behind her, helpless and desperate. It was so much fun to tease him like this. She removed her clothes until she was only wearing her bra and knickers. She put on a special red laced set for today.

"Damn I look hot!" she said fondling her breasts. "Pity you can't see." Casper whimpered softly through his gag in desperation. Jane laughed playfully then turned around.

"By the way, the girls you hang around with. Louise, Holly and Erin. I don't suppose You fancy any of them, do you?"

Casper was bewildered to why she was asking him this question out of the blue. He shook his head, being unable to speak.

"Yeah," laugh Jane. "I don't think you're any of their type anyway. Obviously not to say they don't like you. They served time in solitary for your sake when you fought Grace after all. It's just strictly friendship, isn't it?".

Casper nodded.

Jane sighed, then walked over to the bed. She took a seat and looked off at the far wall.

"I suppose, I just envy them." She turned to look at him. "Because they get to hang out with you every day."

"Though, I wonder what they'd think if they saw you like this. How much of a horny little puppy you are and how turned on you get from being bound and teased."

Casper nodded making Jane raise her eyebrow at him. She leaned over and pulled off the tape over his mouth.

"How do you mean?" she asked.

"Well, they all know I'm soft and a cry-baby." He replied, "I mean this place was originally set up to house guys like me. But they don't look down on me for it! Holly and Louise both understood my past and I need to work on my confidence and stop being a pushover. They've been helping me Jane, and Mark, another guy like me. We've been doing weight training and sparring sessions in the gym regularly."

"Yeah, I remember seeing that last week when I took you away."

"So, while I've never really discussed my kinks with them, I don't think they'd be particularly bothered or even surprised about it. They're amazing friends to me Jane and I could only wish you got to know them as well as I have." Jane sighed then put her hand on Caspers cheek.

"Yeah, I wish too." Said Jane. "But they can't know we're together. Can they?" Casper shook his head.

"As I said, I think I'm just envious. I've no Ill will against them, I'm sure deep down they're all lovely. Though, Holly used to be a bit of a trouble maker when she first arrived." Casper smirked upon hearing this. Jane brought her legs up onto the bed on all fours, turned around and pushed her bum against Caspers chastity cage causing him to moan suddenly with surprise. She laughed,

"your friends can't do this for you though, can they?"

"No." moaned Casper. Jane began to rub her bottom up and down against Caspers cage, making him even more frustrated and horny.

"Give me one good reason why I should let you cum today." Said Jane playfully as she continued.

"Because-"pleaded Casper, "I'll give you an amazing orgasm first!"

"Hmmm? Just one? I don't think I can help a man only willing to give me just

one

orgasm. We're not pathetic like you, where were over and done with after only one."

"As many as you want babe! I'll make you cum as many times as you want me to! Please let me show you!" Pleaded Casper.

"Hmmm... That sounds nice. Though, that should be a given wither the cage comes off or not. I don't think I can help a man willing to do the bare minimum. I'll just keep it locked up today." Said Jane sweetly.

She began moving her bottom harder and more vigorously against Caspers locked up penis. His warm throbbing cage felt nice rubbing against the outside of her vulva through her knickers. Jane felt it to be very pleasant while it left Casper a horny frustrated mess.

"Please Jane! I love you. I'll do anything, I'll give you a foot rub! I'll write a poem about you! I'll get naked in the middle of the cellblock if you want! Just please unlock me this time! Please!"

"Fuck me, you are desperate aren't you." She laughed, still bobbing back and forth against him. She sighed playfully then spoke. "Alright, I suppose you've been a good boy." A big relieving grin appeared over Caspers face. Jane turned around then remembered the chastity key was still attached to her utility belt along with the other keys laying at the other side of the room. She giggled softly.

"Oh no!" She announced in an over exaggerated sarcastic way.

"The key is all the way over there. It's a long walk over. I don't know if I can be bothered going to retrieve it." She said grinning. Caspers smile disappeared from his face returning once more to horny anxiousness.

"Unless." Jane continued, putting her hand on Caspers cheek. "My puppy can go get it for me."

"Yes! Absolutely!" exclaimed Casper.

"But you can't take that blindfold off." Said Jane. Casper felt demoralised, how was he supposed to get to the other side off the room blindfolded and hogtied like this? He couldn't even walk, neverminded not being able to see. Then, how was he to find they keys exactly? He would need to crawl around the floor chained up like this for ages. Alas, it was his queen's demand and his lust transcended all logic and reason. He made a move, first with his knees on the bed trying to move to one side. It was difficult with his hands behind his back. He couldn't quite move forward the way he wanted to. Jane found his struggling amusing making her giggle. He kept moving his knees little by little until he felt one was over the edge of the bed. He then slowly turned himself to put one foot over the side. As he attempted to put his right foot on the ground, he moved too fast pulling the chain on his leg cuffs against the cuffs round his wrists throwing him off balance causing him to fall forward the off the bed and land on the ground face first with a thud. Jane leapt to her feet off the bed immediately springing to his side, pulling off his blindfold and putting her arm around him.

"ARE YOU OKAY?". Casper was silent then began sobbing softly. Jane wrapped her arms around him and held him tight.

"Oh, Casper. I'm so sorry! I didn't mean for you to get hurt. I just thought it'd be a little fun. I didn't think it through." She brought her head on top of his and brushed his hair lightly as he wept. She held him in silence for a while as he cried,

"You're quite a sensitive guy, aren't you?" Asked Jane softly. Casper nodded, still weeping.

"Have you always been like this?"

Casper pulled away and looked her in the eyes, sniffling.

"Mum taught me...That in heaven there's no tears. Because the bad things don't exist anymore. But on earth, we need to cry to get us through the hurt. And we shouldn't hold it in, cause then we hurt more."

Jane put her hand on his face and smiled.

"You really miss her, don't you?" Casper looked down and went quiet for a moment still sniffling.

"Of all the things that happened to me. From my dad beating me, to being homeless, to fighting for survival and being bullied by the other thieves and seeing friends getting killed. None of it, not even a fraction of it came close to the pain of when I lost mum. She was my world. She taught me everything. She's the only person who ever truly loved me."

Caspers eyes moved back up to meet Janes. A soft smile grew across his face.

"At least...Until I met you."

"Your mum did a wonderful job. Of raising such a beautiful man." Said Jane still with her hand on his cheek. "I'm sure she'd be very proud."

"Thanks." Smiled Casper. They gazed into each other's eyes for a while in silence.

"Are you still wanting to have sex then?" Asked Jane. Casper laughed.

"Of course. I just need some help getting back on the bed, being handcuffed and all."

Jane helped him back up on to the bed and walked over to the other side of the room to her utility belt. She took the keys and walked back over to him. She knelt back on the bed and shook the keys Infront of him giggling.

"How badly do you want it off?"

"So bad! "He begged. She noticed precum dripping from his cage.

"I'm not goanna lie; I'm wanting it off pretty badly too." She laughed. She moved her eyes from Caspers locked up penis to his eyes. "I want you to do me doggy style. Can you do that?" Casper nodded with excitement.

"Of course! I'll do you anyway you want!"

"You are a little doggie after all." Giggled Jane. "My wee doggie. You were born to do me like this." She leaned forward and gripped Caspers cage with one hand and held the key with the other. She unlocked the padlock and removed the head piece. His penis grew instantly hard. Jane gripped it in one hand, knelt forward and kissed it.

"Do you fancy a wee blowy first?" She asked cheekily.

"Uh-huh" replied Casper in a lustful daze.

"Okay, but no cumming! I still want you to do me from behind. If you cum now I won't unlock it for another 3 months, understand?"

"Yes Jane."

"Good boy."

She wrapped her lips around his cock and began going up and down on the shaft. She looked unbelievably hot in her red lace underwear sprawled out on the bed like this. Her lips and tongue felt so warm and magical. She brushed her tongue delicately around the head pushing back his foreskin and stimulating the more sensitive areas. Casper let out another moan of ecstasy. She was gobbling him up like an ice lolly on a hot summers day and he loved every second of it. He began not to care if he came now, even if it meant being locked for another three months, It felt too good.

It'd been a long time since Jane last had a cock in her mouth. The old familiar feeling of it being so hard and warm against her tongue and the insides of her cheeks felt comforting. She hoped she was doing a good job, until it was confirmed once again by Caspers moans. She loved hearing him moan; she was getting wetter and wetter; she really wanted it between her legs now. At this rate he'd Finnish soon. She pulled away leaving Casper in frustrated lustful anticipation, one of her favourite states for him.

She turned around, bent over presenting her bottom to him then slipped off her knickers. She moved her bum backwards towards has erect penis until it made contact making Casper moan once more.

"You ready?" She asked

"Yes." He panted.

She wriggled around until she felt his head on her labia then pushed down onto it, entering her. She let out a sharp inhale as she pressed his cock inside her.

"Hmmm, good boy" she moaned.

If felt so nice. She eased back and forth slowly and teasingly. Casper was in heaven. It was so warm and cosy inside her. Each gentle thrust against him was magical. Jane began to accelerate her thrusts. They both moaned in ecstasy as Jane went back and forth using Caspers penis as a glorified dildo while he was in his restraints, his warm cock felt marvellous massaging her insides. He began to thrust back despite the cuffs. She spoke as they continued their dance.

"Mmm, your dick holds a grudge for keeping it locked up. This thing as solid as a rock! It feels so fucking good" She whined.

"It's missed you since last time!" Joked Casper.

"Hmmm, I can tell." She giggled. "Are you close?"

"Yeah." He replied in ecstasy.

"Oh? Well, I won't stop you." She moaned. Her thrusts got even faster.

"I want you to cum for me Casper. Don't hold back, you've been such a good boy. Go in and fuck me as deep as you can and let it all out! You deserve it!"

"Yes Jane! Ah! Ah!"

"Do it! Cum for me you little slut!"

He thrusted in as deep as he could and climaxed hard inside her with a loud roar. He was in nothing but pure bliss. The whole world around him disappeared for a moment. It was as if he were floating. It felt so hot to finish in the woman he loved.

Jane moved forward causing Caspers cum soaked penis to fall out of her. She turned around and kissed him on the lips, then pushed him backwards falling gently on the bed with him. They lay for a while relaxing together in silence until Casper asked Jane to be uncuffed feeling more and more uncomfortable with his hands and legs still cuffed behind him. She granted his request and knelt over to where she left the keys on the floor then picked them up and unlocked his cuffs. When she did, he wrapped his arms around her and her arms around him then continued to lay in peaceful silence together.

After a while Casper suddenly remembered the situation regarding Louise's mother, and his peaceful bliss was put on hold. He remembered how he'd been lying to Louise telling her he'd been trying to contact his "Outside person" for the past 2 days to no avail. This was in effort to buy time until he would or would not ask Jane today.

He looked down at her as she lay in his arms. Her eyes were closed and was breathing so calmly. She looked so Beautiful and peaceful. He had to make his decision now, was he going to tell her or not?

She opened her eyes slowly and looked up at him with a smile then noticed the troubled look in his eyes. She looked back at him concerned.

"Casper. Is everything okay?" He looked back at her with a serious look.

"There's something you should know." He said.

He sighed then told her everything from the beginning. Jane listened attentively, from the bakery bombing to David Shaw and Finns ultimatum. She was shocked. She didn't expect anything like this to happen in a million years.

"So- "Casper spoke when the account was finished, "our only hope now is to try and contact someone who can go into Belfast and take Louise's mum to safety?"

"To where? Scotland?" asked Jane. Casper shook his head.

"To Donegal, Louise's grandad lives there in a cottage out in the Styx. She reckons she'd be safe there with him."

"And have you found anyone willing to go get her?"

Casper looked back at Jane earnestly.

"Wait, no, you don't mean?"

"You're the only viable option. At least from everything I can think of-"

"What!? Do they know about us!? Holly and Louise, did you tell them!?" said Jane sitting up stressed.

"No, no!" Casper assured her sitting up on his elbow waving his hand. "I only told them that I knew someone on the outside and just needed to reach out and ask."

"Okay, okay. So hypothetically if I agreed to do this, how would you tell them!? Yeah, I'll just send the guard I'm shagging Jane to go all the way down to Belfast and taxi a pensioner to the other side of Ireland while trying not to get shot and killed by a handful of well-armed terrorists who are stalking her. Should be no bother!"

Casper sighed. "I'd tell them the woman I'm sending wishes to remain anonymous for her safety. They understand the culture of no grassing, they'd respect that. But it's fine. I knew I shouldn't have asked, it's a stupid idea."

"This is madness!" Said Jane. "Is there no one else that you Holly or Louise know that could go instead?"

"No." said Casper disappointed. "All me and Holly's past associates are all either dead or in prison and Louise's old gang are the ones we're going up against"

Jane sat staring into the distance vexed. She sat in silence for a while then spoke.

"New inmates are arriving today. David Shaw will be one of them. He could be walking into the cellblock as we speak. If what you said earlier was true then we only have five days before him or Louise's mum will be killed." Jane looked down. "I'll need to head off tomorrow morning latest." Casper looked back up at her in surprise.

"Wait! so you mean? - "

"If Louise kills David" Jane interjected. "That'll be on me. It's my job to keep the inmates safe from harm and prevent bad things happening to them. I don't want his murder on my conscience. If I tell Samantha about all of this and have him and Louise isolated, they'll know you spoke up and who knows? Maybe Holly and Erin will hand you over to Grace in a ribbon for being a grass, and Louises's mum will get killed. I don't feel I've much choice here."

"I'm sorry." sighed Casper

"I'm going to need weapons, armour, and a believable excuse to leave for a few days," said Jane. "I'll need to see Samantha ASAP to get the ball rolling on it." She stood up off the bed, picked her clothes off the floor and began to get dressed.

"C'mon! Let's get going!"