Miss Jessica's archive clip content

The caretaker has had a rather drastic transformation! The head girl and her friends thought it would be rather amusing as an additional punishment to make him dress up in their sportswear for perving on them. They have even given him a wig and make-up! They have requested he be like this every day for work for the next 7 days so says the letter the Headmistress reads out to him. They have also requested further punishments from the Headmistress: over the knee punishment with knickers on and the same with knickers down. Then a tawse applied to his hands and to be finished off with a good caning. The headmistress chooses to use her hand a slipper to spank him over the knee with, a good 6 tawse strokes on each hand and a final 6 of the best with a thick cane. The humiliation and further punishments should ensure he doesn't have a wandering eye ever again.

The headmistress has sent the caretaker to see Head Girl Miss Jessica. He's been paying a bit too much attention to the girls playing netball, swimming etc standing there staring at them like a right little pervert. Some of his work has been falling behind due to his perving. So Jessica has been allowed to do whatever she wants to him on the Headmistress' command. Brandishing her gym plimsol in her hand, Jessica tells him he's going to get a good spanking. Down his trousers come and over her knee he goes. Jessica starts off with a good hand spanking but soon moves onto the rubber-soled plimsol for a very harsh solid spanking whilst he gets a good telling off. He has a very red sore bottom by the end of his spanking. Jessica then tells him she wants him to come back later as she'll have something else he has to do... continued next week!

After 50 cane strokes earlier, Miss Jessica comes back to check her sub who is chained to her cross. She inspects his bottom but the cane strokes seem to have faded a little too much for her liking so Miss Jessica decides it's time for more punishment. Firstly with her Jeffires riding crop, a firm powerful crop, that soon reddens up his bottom with each vicious stroke. Next, it's onto a swishy dressage whip which makes a lovely noise through the air before landing harshly on his bottom. It's nasty little tail really cutting into his bottom. Miss Jessica then leaves him there to come back and punish him some more later.

In walks Dan with the files Miss Jessica wanted but then she says what was that with the way he greeted her? Not very respectful was it? It has also been noted he's not very respectful to the other women in the office. After putting on her leather gloves, Miss Jessica gets him to stand in front of her and slaps him around the face whilst telling him off. Next, he's over her knee for a good solid leather glove hand spanking. Miss Jessica then orders him to the floor to start kissing her shoes and feet. He will learn his respect for women. This also includes kissing Miss Jessica's leather skirt and her bottom for extra humiliation. He is then back over Miss Jessica's knee for a long hard leather paddle spanking and he gets a very sore bottom. Miss Jessica finally orders him onto his knees to then kiss her leather gloves making sure he understands how he needs to behave from now on.

Miss Jessica walks in on her sub, who is handcuffed and trapped in the smotherbox on the floor. Walking around him she tells him how he's going to get smothered with her lovely bottom. Dressed in red stilettos, black fishnet tights and a PVC bodysuit, Miss Jessica hovers over him before sitting down and stopping him from breathing. Moving around the box, forwards, reverse, laying down and resting her legs on him, Miss Jessica lets him breathe occasionally. Very rapid breathing from being trapped in the box are the only noises from him when Miss Jessica kindly lets him gasp for air. She tells him before she leaves, that he's going to be locked in her room until after dinner when she'll come back for more facesitting.

Miss Jessica gets a knock at the door. Substitute teacher Steve is not playing by the rules by letting pupils go home early as he wants to go to football! He's also slating the pupils saying they're not very clever. Miss Jessica decides he needs an attitude change to fit in at her school, in the form of a good spanking. Pulling down his trousers, Miss Jessica pulls him over her knee. She starts hand spanking his bottom getting it nice and red. Due to his cheekiness, Miss Jessica then uses a black rubber soled slipper to spank him with. Miss Jessica hopefully knocks some sense into him with a very red, sore, truly spanked and slippered bottom.

Miss Jessica has a very interesting game for her sub. He has to pick 6 cards from one pack and 6 from another and put them on the table. Miss Jessica also has 6 different implements: 2 riding crops, a wooden paddle, a leather paddle and 2 canes. He then has to turn over the card from the 1st pack, then roll the maths dice which has + - x / on it. He then turns over the 2nd card to reveal his total punishment by combining the numbers with the maths dice result. His fate is therefore in his hands!

Jessica comes into the lounge to find her naughty boy Dan. She asks him if he wants to talk about anything she might have found in his room whilst tidying up... He thinks it's his magazines but then from her hand she reveals a pair of pink silk panties. Jessica can't believe he'd stolen her knickers so tells him he deserves a good spanking for his naughty behaviour. Pulling down his trousers, Jessica gets another shock, as she pulls down his jeans, she discovers he's wearing another pair of her panties! He starts off by getting a good handspanking whilst getting a good telling off. Then Jessica spys a paddle hairbrush on the side and gets that over to spank his bottom nice and hard. A bit more handspanking and back to the brush, he's gets a thoroughly deserved punishment.

Miss Jessica asks her slave if he knows what's behind him... a cock and ball pillory. Miss Jessica gets him to turn round and straps his ankles in then pulls his cock and balls into the device and clamps them down tight. She then meanly plays with his balls, crushing them in her hands with him gasping. She then sits down and gets out a pinwheel to start rolling all over his trapped area. Next out comes a mini leather paddle so Miss Jessica can slap him painfully. After that a mini whip for further abuse. She then moves the C&B pillory up to stretch his balls up higher and punishes him with the pinwheel and her hands again, flicking and squeezing everything. Miss Jessica has had fun with her toys.

Nurse Jessica is sorting through a box when a patient sneaks up behind her and gives her a hefty slap on the bottom! He then starts complaining about an injury and rubbing his groin. Jessica had heard about his behaviour from other nurses and had just experienced it first hand. Jessica then pretends to go along with him and look at his "injury" whilst getting out a wooden paddle from her cupboard. To get a better view she moves him to bend over, then grabs his waist and starts spanking him with the paddle. His bottom gets very red, very quickly from the harsh spanking implement. Jessica agrees to let him go if he takes the rest of his punishment. He then bends over leaning against the radiator and Jessica gets another wooden paddle out - a thin long one - for lots more spanking with it. Finally, a large thick heavy wooden paddle is revealed and Jessica tells him he's going to get 12 of the best and makes sure he understands her nurses are to be respected.