This is a new idea, not something I have much experience with, so I am writing from a relatively novice point of view. Constructive feedback would be appreciated.
They had talked long and hard about this particular decision, whether or not it would be a good idea, whether the theory would match the reality and so on. It wasn't an easy decision to make. They had decided on a trial period of a month to see how things would go.
Marcus smiled at his partner nervously, he loved her very much, and was excited by what they were about to attempt. However the crux of the matter was simply that he couldn't or rather soon wouldn't be able to become excited without express permission after this day, for 30 days at the very least, and possibly much much much longer, if things went according to plan.
Jennie smiled back, holding tightly to the piece of plastic that would soon change their lives, and dynamic forever.
"Are you ready for this then honey?" She asked a nervous smile on her lips.
"Um, well, I guess," he replied nervously.
"You know what you have to do now then don't you?"
He nodded, not able to reply the butterfly's fluttering dangerously in his stomach, as he stripped down to his birthday suit. He stood, thankful for the cool air, keeping his excitement to a dull minimum, as he knew the consequences he'd have had to suffer had it risen to attention.
They both looked at each other nervously, a slight smile gracing Jennies lips as she slipped her warm hand around his manhood, making him jump. He tried to control his thoughts as she slipped the ring around the base behind his balls, the tightness making him groan. Then she slipped the sheath on and locked the whole thing in place, quickly pocketing the key.
The whole thing took less than a minute, which made him all the more aware of his lack of control, making him grumble slightly under his breath.
Jennie simply raised an eyebrow and gave him one of her most evil grins to date, before telling him to get dressed, it wasn't like he was getting any action any time soon.
Marcus quickly obeyed not sure that he wanted to disappoint her or make her angry knowing that his little man would soon be feeling the consequences of all his actions.
Several days after the event Marcus was starting to feel the effects of not being able to raise the mast. He was getting very frustrated and his balls were starting to ache. He had never really been aware of the effects the things Jennie did day to day that turned him on. However he had kept himself on her good side, knowing that soon she would milk him, or if he was lucky she would just let him masturbate.
Of course he was hoping for the latter but then he didn't know for sure what really was expected as this was all new for the both of them. He was sitting watching television, trying hard not to think anything remotely erotic as this would only lead to bad places.
"Marcus, go upstairs and get naked, kneel on the floor and wait for me!" Jennie called the command from the kitchen where she was currently preparing dinner. Marcus sat for a moment longer, nervousness causing his inaction before realising that stalling would likely lead to more problems than it would solve. "Yes Mistress," he replied quickly as he started up the stairs to their bedroom.
In the kitchen Jennie smiled, knowing that he was nervous and knowing also that he had no idea what she had planned or what he was letting himself in for. She gave him 5 minutes to complete what she had asked him to do before preparing herself to go to him.
She had read on the internet of cunning and evil ways to milk a male who'd been in chastity, firstly that it was a good idea, good for overall prostate health, and also could be a wicked and evil experience for the person being milked.
As such, and after much reading, while he'd been distracted with his cock, she'd created an ice cock ring which he would have to wear while being milked, making the process so much less enjoyable for him, but also keeping him healthy and flaccid so that she could quickly lock him up once more. Then her truly evil plans would come to fruition.
Quietly she climbed the stairs, stopping outside the door to hear Marcus muttering to himself, almost like a prayer that she'd let him masturbate or even better have sex. Slowly she opened the door, the item hidden in her hand, and smiled down at him, in all his vulnerability.
"Hello slut," she said, a wicked grin on her lips, "What were you just saying to yourself there my pet?"
"Um," he blushed profusely, "Nothing of importance Mistress. Honestly I just ... was wondering what you are going to do with me Mistress." He dropped his head, his cheeks burning with embarrassment at being caught talking to himself.
"Are you ready to be milked my darling?" She asked her voice all sweetness and light.
"Um," he looked totally despondent, "I guess I am Mistress."
He looked up with saucer filled eyes as she placed the ice cock ring on the bedside table, followed by opening a drawer and pulling out a prostate massager, and some lube too. His eyes went wide at the sight of these things, gulping convulsively.
"Stand up boy," Jennie said without pre-emption, she was as nervous as he but refused to show it. "Now spread your legs nice and wide."
He did as he was told as quickly as he could, trying to forget what was about to happen. Although they were both into BDSM, he'd never really had anything up his ass, it wasn't something either of them had been inclined to try until now. He hadn't really thought she'd do that but obviously she was about to, and he was more than a little nervous.
She picked up the cock ring and after unlocking his cock quickly slipped it onto him, which made him gasp at the icey coldness on his cock. Even if he had been excited, it was unlikely he'd get hard and he knew it.
"Now slut bend over the end of the bed and put your hands down on the mattress flat and don't move unless I tell you to."
He moved into position, spreading his legs for balance, feeling very vulnerable and on show suddenly, especially when Jennie stepped up close behind him, with the lube and massager in hand. He also noticed that there was a cup on the floor below him, which he hadn't even noticed before.
He jumped when she poured the lube on his virgin ass rubbing slowly pushing her finger inside, stretching him a little, preparing him for what was about to come. Once she felt he'd started to relax she began forcing the massager into his anus, which at first resisted but soon had it snugly inside him.
She lifted the cup from the floor, holding it under the end of his penis, while she began to use the massager as the instructions had told her to, stimulating his prostate, making him moan and whimper simultaneously.
She kept up the constant stimulation for about 8 minutes before he started to beg her to stop, that it was too intense and he couldn't take it. She simply shushed him telling him that if he wasn't quiet then she'd just gag him, and that anyway this could take up to forty minutes. The tone of her voice warned that if he didn't behave then he would be punished severely.
As it happened it took much less than the 40 minutes advised, only about 25 till he had given his all, the liquid accumulating nicely in the glass. Once it was done, she removed the massager, and the now nearly melted cock ring and replaced his chastity before allowing him to stand up on weak legs.
"Now for my fun," she said sliding onto the bed in front of him.