Headmistress Shows Natalia Your Tiny Caged Dick

Ivy has been sent out of her hockey lesson and to Headmistress’s office. However when she arrives, still wearing her naughty little hockey kit, Headmistress is nowhere to be seen. Instead Ivy finds Headmistress’s discarded blouse and skirt on her desk. Ivy picks the items up, they feel so soft and smooth. She runs the blouse over her bare legs which feels amazing, it feels so good she wants to feel more of the satin against her and she starts to slip off her hockey kit starting with her boots and socks. Now she can feel the satin against her feet before she slips off the rest of her hockey kit while caressing the satin clothing. When she is completely naked she runs the satin all over her body including her pussy and breasts. How good it would be to wear this every day, and she slips on the blouse and skirt before sitting behind Headmistress’s desk.

Pixiee has skipped her hockey lesson and come to Headmistress’s office to look for something, but while riffling through the drawers she hears someone coming and ducks down behind the desk poking her head out to see Miss LaLay take a seat. Miss obviously has a meeting with the Head and is going to be staying. Pixiee has no choice but to stay hidden, however while Miss waits she starts to caress her stockings. As Pixiee watches her sexy teacher she can feel her pussy twitching and she rubs it gently through her shorts. Miss LaLay is really enjoying the feeling of her stockings and she starts to strip, prompting Pixiee to do the same as she grows increasingly excited. When Miss is in just her stockings Pixiee, who is completely naked, rubs her pussy faster and as she cums hard she has to cover her mouth to keep herself quiet!

Essie and Ivy are in the medical room waiting for Matron. They are both claiming to be ill so they can skip their tennis lesson and they are both wearing their cute little tennis outfits with white ankle socks. While they wait Essie plays with her soft white socks, scrunching and rolling them down while Ivy watches with amusement, she cannot understand how Essie can be so involved in how her socks look. However Essie explains how important the socks are to the overall outfit and convinces Ivy to join in and while they play around with their socks they start to slip off their tennis outfits. When they are in just their underwear they look even sexier as they pull up and then push down their socks while showing off their soft soles. Eventually they have stripped off everything apart from their white ankle socks and they look very cute indeed.

Miss LaLay has caught you in her classroom again, underneath the desk trying to peek up her skirt. She is not in a good mood and catching you again has made her very angry and she is going to teach you a proper lesson this time. She shows you her cane, swishing it through the air and flexing it. She explains how she will be caning your bare ass hard and demonstrates just how fast the cane can cut through the air, it really makes the most sinister of sounds. As she demonstrates you are beginning to wish you had not dared sneak a peek today, but when she tells you to drop your trousers and pants you know it is too late to run and you obediently bend over her desk with your bare bottom pointing up. Now you look into her eyes as she rains down the thrashes on your skin, you had better make sure you do not cry out as it will only make things worse. You can only hope she will tire quickly with such powerful strokes.

Miss Lee is reading alone in the library. At first she does not see that you are hiding and perving on her, but as you move to get a better look you sees you! She calls you out and while she tells you off she also notices just how much you are staring at her big boobs and deep cleavage. She is quite entertained by this so she decides to tease you with her big bouncy tits, and when she sees you growing in your trousers she is very clear that you will not touch your cock. She starts to slip off her outfit making sure she bounces her tits as she does, pushing them together so they look even bigger. When Miss is in just her lingerie she slowly slips off her sexy red lace bra and lets her big boobs escape grabbing them and squeezing them before slipping off her panties too, before calling you in closer to bury your face in her warm breasts.

Miss Lee is waiting for Headmistress in her office, she is wearing her very tight outfit with her low cut top, she is also wearing a pair of very sheer grey pantyhose accompanied with red high heels. While she waits she runs her hands all over her sexy nylon covered legs as she crosses and uncrossed them. They feel amazing and as her legs rub together Miss feels increasingly naughty. She slips off her skirt showing the full length of her nylon legs and the sexy red bodysuit she is wearing, and when she undoes the gusset of her bodysuit she reveals she is not wearing any panties underneath! You can see straight through the sheer pantyhose and see her spread pussy pressing against the nylon. Miss continues to strip and soon she is left in nothing but her pantyhose as she shows off her nylon covered pussy and soles of her nylon covered feet.

Pixiee has just got back from pretending to play for rival school St William’s hockey team so she can help throw the match and has come straight to Headmistress’s office. She made a point of bringing you back with her when she noticed you perving on the girls on the sidelines and now you are standing in front of them both, Pixiee still in your school’s hockey kit and Miss in her tight satin outfit. While Pixiee explains Miss looks very amused, it seems quite clear that you are a panty pervert who watches the girls’ sports hoping their little pleated skirts will blow up in the wind. So they both start to tease you, Pixiee strips showing her big gym knickers and Miss slips off her skirt showing her satin panties. They can both see your bulge in your trousers so Miss decides Pixiee can take you back to her dorm and do whatever she wants with you.

Lola is reading in the library when she is joined by Miss Tolman. They do not yet know that you are spying on them from underneath the desk but when you move they hear you and you have no choice but to skulk out of your hiding place. Lola knows you were trying to peek up her skirt and when you are caught checking out Miss Tolman’s bottom it becomes obvious you are nothing but a panty and ass pervert. They decide to have some fun with you and they pull up Lola’s skirt and make you smell her ass through her panties. They have no intention of stopping there though and they both start to strip making you come closer and smell both of their asses through their panties. When they are both completely naked they even make you smell their bare asses after you have had Lola’s panties stuffed in your mouth.

You are the Head Boy of the all boys school St Hugh’s and you have been sent to St Mackenzie’s Headmistress’s office. You are feeling very apprehensive as you stand in front of Headmistress Mackenzie who is accompanied by four of her sexiest students, all with very different looks and uniform styles, and they all look ready to pounce. Headmistress explains how she has come up with a program to take advantage of all the money floating around St Hugh’s and as their Head Boy you will be the one to make sure all of the boys at St Hugh’s sign up to this ‘very expensive’ program. This program will ensure that all St Hugh’s boys are able to concentrate fully at all times meaning their grades will improve tenfold, and this is how it will work… Groups of St Hugh’s boys will come and stay with us at St Mackenzie’s where you will undergo mass milking. That’s right, you will all be milked over and over by our sexy students making sure your balls are so drained you have no distractions whatsoever and all you concentration can go on your work. However while Headmistress explains all the intimate details of the program she expects you to show her what you’ve got so, as her girls tease you and slip off their uniforms, you will stroke yourself for her and let us hope you can manage to absorb all the information as you jerk your cock and cum hard for her!

Natalia has heard that Headmistress & Miss Taylor have punished your tiny dick. She is very curious and wants to see it; she is also a bit disappointed she didn’t get to witness it first-hand! So you drop your trousers to show her your poor little bruised & battered cock. She cannot get over how disgusting it looks and she explains how you deserve everything you get for having such a tiny worthless dick. Natalia also explains to you how she will also be punishing it if you dare get hard, so Mr Haywood, you better try and control that pin dick as she slowly slips off her tight little uniform & lingerie. However we all know you have zero control over your dick and as Natalia teases you there is an inevitable erection, and tiny as it may be it will be punished. So a naked Natalia digs her nails deep into your dick, and as it shrivels up you can tell how much it is hurting you.

Helen has snuck out of her gym lesson and has come to Headmistress’ office knowing it would be empty. She is still wearing her cute netball outfit and has brought her packet of cigarettes with her. As she takes a seat she lights a cigarette knowing that she will not be disturbed for a while, as she holds it in between her fingers & long pointy fingernails she inhales deeply, exhaling through her sexy lips. Helen gets more comfortable, holding the cigarette elegantly as she takes time sucking on its butt, enjoying how smoking relaxes her, it is much better that taking her gym class! As she makes her way through the cigarette she occasionally flicks the end with her long painted nails, dropping the ash into the glass tray, before finally stubbing it out after taking her final drags.

Amy has snuck into rival school St Paul’s to find you; she knows you are a dirty pervert teacher always sniffing around St Mackenzie’s students and has tempted you back to our school to have some fun of her own and teach you a lesson. You have followed her willingly into the medical room thinking you are going to get to fuck our gorgeous blonde Amy, but you are very wrong. She looks so sexy dressed in your school’s burgundy uniform and you can feel yourself getting hard in your trousers just looking at her. As she pulls up her skirt and pulls her panties down at the front, showing her neat little bush, you are feeling so ready, but then she laughs at you! She has no intention of letting you anywhere near her, she just wants to tease you so much you feel like you are about to burst! She bends over showing her perfect round ass in her naughty thong and runs her hands up and down her long legs and over her soft panties, pulling them down occasionally to show you exactly what you cannot have! You can feel your cheeks getting redder, you are so hard you feel like your cock may explode, but Amy is relishing in the tease you and the fact you cannot touch her just amuses her even more. She can see your frustration building as she repeatedly teases then denies you, and she cannot resist telling you how you are nothing but a desperate loser and how you will never even get to touch her, never mind fuck her!