Bob 4

* * * * *
This work is intended for ADULTS ONLY. It may contain depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.
* * * * *

Part 6

During the week Bob was allotted two girls each day to supervise him, a job they all enjoyed especially when he needed to go pee. Naturally they took him into the girl’s toilets where, in several cases, girl’s got their first look at a penis.

Bob himself was gradually realising that his immediate future was going to be ruled by girls and there was very little he could do about it. Every day after school he would be collected by Mary, taken home, stripped just inside the front door, then made to do housework. Floors were scrubbed or vacuumed, he learnt how to do laundry, fold clothes properly, even iron when necessary, and of course hand wash delicate items like his mum’s knickers. After the allotted housework was completed Bob was fed then toileted and naturally given his special night time drink which he would pay for by licking Mary to orgasm. Bob was then put to bed, tied in the normal manner after which Mary gave him a dozen good hard spanks with her hairbrush just to remind him he had to behave himself, and of course for the pure fun of it.

Bob’s mum was absolutely delighted with the way the house had been cleaned up, the fact that after her long hours at work she didn’t need to do a thing at home, not even make herself something to eat with the delicious meals Mary was leaving for her. Even better was the fact that she didn’t even see or hear Bob at all, coming home was almost like a little holiday compared to the stress she had been going through before. Added to that was the fact that, at Mary’s instigation, she was going to spend the whole weekend at Mary’s house relaxing and doing whatever she wanted. She would sleep in Mary’s room while Mary would have her room and spend the weekend looking after Bob.

Mary was also delighted, naturally. All of her plans had fallen into place and she would have from Friday after school until Monday morning to torture Bob to her heart’s content, and she was certainly going to have him screaming and begging for mercy for much of that time.

Mary had received the parcel she’d ordered containing two pairs of handcuffs and a lovely swishy cane. She had also received some coaching from Bob’s headmistress on the most effective way to cane a boy, and had been practising with it on a pillow until she had become quite proficient with her accuracy.

In the manufacturing line, Mary had taken some lightweight canvas, drawing pins and a snap fastener to make something to fit snugly around Bob’s flaccid cock. The pins, pushed through the canvas, were held in place by another strip of the material sewn behind them. They were then snipped down to the length Mary required and smoothed off so they were not too sharp. When put on Bob’s cock the pins would press into the skin all the way round but should be reasonably bearable unless of course he started to get an erection. There was also material sewn to it so his cock could be forced back and padlocked around his balls. In future he would be sitting down to pee at school, and she was sure she could find some way of encouraging the girls at his school to do what they could to get him hard as often as possible.

Mary’s dad had a good workshop set up in the garage which Mary made use of to produce her own ball crusher out of some plywood and screws with wing nuts. A lot of the things she’d seen and liked that were for sale on line, she was sure with time and care she could make at home, thus saving a lot of money. She had visions of turning Bob’s bedroom into her own little dungeon, something she really hoped to achieve before the next school holidays. She had made a good start, as well as the items already mentioned she had a multi-strand whip made from some of her father’s old leather bootlaces and a file handle. Everything would be well tested over the weekend.

Part 7

Finally Friday arrived. Bob thought he would be taking things easy over the weekend with his mother home to look after him, and Mary did nothing to hint that would not be the case. After his normal routine of housework, dinner and toileting, being made to drink Mary’s pee and of course licking her to a nice climax, Bob found himself tied down in bed face up this time.

“I’ll see you later little boy” Mary said as she left the room, leaving the door wide open.

Mary took her time relaxing and eating her own dinner, knowing that Bob would be expecting his mum home from work later, and fully expecting Bob to revert to his previous demanding form. He didn’t disappoint her. Opening then closing the front door as if his mother had just come home got an immediate demand from Bob for his mother to “Come here right NOW!!!”

Mary was more than happy to oblige.

“Well, well, that didn’t take you long to forget everything I’ve been trying to teach you all week” Mary said as she walked into his room.

Bob turned quite pale as he realised the trouble he was now in. Mary quickly fixed her homemade cock ring just below the head of Bob’s cock, told him not to run away while she got changed into something more comfortable. Mary then went into his mum’s bedroom, stripped off her school uniform and put on a dressing gown, then picked up her bag of toys and returned for some fun with Bob.

Mary was not the biggest girl in her class but she did feel she had a nice pair of titties and was proud of her enticing nipples which became so firm and sensitive when she got excited, like they were right at that moment. In fact, Mary was a very beautiful girl and not ashamed at all for other girls or her mother to see her naked. She now extended that view to boys who were tied up by kneeling on the bed between Bob’s legs and slowly slipping off her dressing gown. The expected result was evident as Bob’s cock started to harden.

“Agggggggh it hurts, take it off, take it off” Bob begged, as the pins sunk ever deeper into his cock shaft.

Mary’s reply was simply to lightly tickle his balls which naturally made it even worse. She wanted a close look at the results so she quickly ran downstairs and came back with a container of ice which she used to cause Bob’s cock and balls to shrink. A close inspection of Bob’s cock showed nice red indentations where the pins had sunk into the shaft, but they had not drawn blood which was ideal. Mary decided she would make a couple more of these rings so she could have up to three on him at a time. In the meantime, Mary replaced the cock ring but this time at the base of his shaft just in front of his balls. She wanted to find out if once he got hard it would help to keep him like that. Product testing was certainly fun.

Mary couldn’t resist any longer, she scooted up Bob’s body until she straddled his head then lowered her fanny onto his mouth.

“Lick” she commanded.

And Bob licked as if his life depended on it.

The combination of his tongue and loud moans as his cock once again got hard, very quickly sent Mary over the top into a wonderful orgasm. Mary remained where she was for a few minutes giving herself a chance to calm down. Bob’s loud moans were sending very pleasant vibrations through her fanny. Finally Mary got off the bed and inspected Bob’s cock. It was really hard, just right for another test.

Using some string, Mary tied it around Bob’s cock just behind his circumcised head, then pulling his cock horizontal facing his feet she tied the string off to the base of the bed. Now to test both her skill and the effectiveness of the cock ring. Damn! This could get very noisy, she thought, and quickly ran to the other bedroom to return with the knickers she’d worn all day. These she stuffed into Bob’s mouth as a gag. Picking up her cane she took a couple of practise strokes using each of Bob’s nipples. His eyes almost bulged out as he screamed each time. The knickers were ideal allowing Mary to hear his agonised screams but at the same time reducing them to a reasonable level. She was very pleased with the results both of her accuracy and the effect they’d had. Now for the big test.

Starting at the base of his cock, Mary bought the cane down with a wicked cut. Bob’s body leapt up as far as his restraints would allow and the loudest of screams sent a shiver of satisfaction through Mary. She watched as a ridge formed on his cock, then took another stroke just above the first. Her aim was perfect, there was hardly a gap between the two ridges that those strokes had produced. Even better was the fact that the cock ring seemed to be doing its job and Bob’s cock hadn’t softened at all. Taking her time, Mary laid down stroke after stroke as she worked her way up Bob’s cock. His now constant screaming, bucking and tears was almost enough to make her cum without even touching herself. One final stroke to the shaft. Perfect. The cane cut into the very joint between the shaft and head of his cock. Judging by Bob’s reaction this was a very sensitive area. His whole body shuddered as Bob passed out from the pain.

Mary slapped Bob’s face back to consciousness.

“Don’t pass out yet, Bob, we’re just getting to the best bit,” Mary teased.

She meant of course the best bit for her, and very likely the worst bit for Bob.

And it was. Mary managed to fit three strokes in on his cock head then untied his cock for the cruellest stroke of all, directly on the end of his cock front to back and dissecting his pee slit, causing Bob to pass out for the second time.

(The End)