What Are You Doing With Those Knickers In Your Pocket, Boy?

[blueunderpants]

I have a role play fantasy. You are in a schoolboy role; I am the headmaster. I ask you to turn out your pockets. You have some stolen knickers in your pocket!

Right, bend over, trousers down for a hard 12 of the strap and 12 of the cane across your underpants. Then it is underpants down for a repeat.........however this does not teach you a lesson!

Next time I find you wanking off into the knickers...............what spanking punishment must I give NOW? How many strokes?

[caned1983]

Got caned recently while wearing girlfriends' v.short lycra 'hot pants' but
the master did not really notice them ! they are more comfortable than
what I would wear, as they have no seam - stretchy and naughty, shame
then that the guy I went to did not realise I put them on for the session !

[Leigh6]

I was punished in knickers recently by a Headmaster from this site.
I had to report to the Headmaster's study because I had been caught looking up a teacher's skirt when she was getting a book from a high shelf in the library, and was then found to have pictures of girls being spanked and caned in my possession, which I had to confess I found exciting.
To cure me of this unhealthy interest, Sir decided that I should be punished as a schoolgirl so I had to go and change into knickers and stockings and report back to the study for punishement. In this way I was spanked and had to bend over the sofa arm for the strap and cane, then I was sent to the bedroom to reflect on my punishment. Unfortunately Sir then found that I still had not learnt my lesson, so I had to kneel on the bed and have my knickers pulled down for a further caning across my bare bottom.
It was the first time I had been punished in that kind of scenario, and it was quite powerful.

[caned1983]

Many 'tops', in roleplay or not, may choose to disregard what you are wearing, as they have intention of removing them as quickly as possible,
my pre-Christmas CP was satisfactory, although the Master thought it could have been more enjoyable for both if the roleplay was more realistic,
but that was at his disrection - spent more time over his lap getting slipper
when I was hoping to get to the vaulting horse for a dozen with a cane !

Getting the tip of the cane stroking inner thigh from knees up added to his
build-up, got very aroused but trapped underneath me, so he didn't notice
that until I stood up. I wore the lycra pants more for comfort on the day
but they came off after 10 minutes and stayed off for over an hour.
I perfer the element of surpirse, rather than get the penance in writing
ahead of the visit - then I know the master will spend some time ahead
of my arrival thinking of what to try ! Any thoughts

[kram]

i like the sound of your fantasy blueunderpants,pity your so far away,it would have to be lads underpants in my pocket.

[mondeo]

I am in my aunties bedroom trying one of her skimpy nylon panties when she walks in and sees my bulge through them, what do you think you are doing? she quickly sits down and pulls me over knee and gives me a dam good slippering.As she delivers every stroke saying the next time i catch you in my panties iwill make you dress up as a girl in frilly pants and stockings this made me cum all in her panties i was wearing, she then calls me a disgusting boy and tells me to get out.

[samantha_tv]

I was punished in knickers recently by a Headmaster from this site.
I had to report to the Headmaster's study because I had been caught looking up a teacher's skirt when she was getting a book from a high shelf in the library, and was then found to have pictures of girls being spanked and caned in my possession, which I had to confess I found exciting.
To cure me of this unhealthy interest, Sir decided that I should be punished as a schoolgirl so I had to go and change into knickers and stockings and report back to the study for punishement. In this way I was spanked and had to bend over the sofa arm for the strap and cane, then I was sent to the bedroom to reflect on my punishment. Unfortunately Sir then found that I still had not learnt my lesson, so I had to kneel on the bed and have my knickers pulled down for a further caning across my bare bottom.
It was the first time I had been punished in that kind of scenario, and it was quite powerful.

Great story Leigh, although I prefer to wear the full school uniform, rather than just stockings and panties

[Nickysdown]

I regularly use this school knickers fantasy as part of my punishment play sessions. In my case the theft of school knickers, for use as wanking aids, has a basis in reality. As a schoolboy there were numerous occasions when an observant master or, more preferably, an observant and strict mistress could very easily have caught me in possession of stolen navy blue or white school knickers. I used to take two or three pairs each year from the school’s lost property cupboard and often kept them in my blazer pocket as school bags could be searched if anything had gone missing. The pocket was more secure unless you were also a smoker or were suspected of being one! Some knickers though were thicker than others and if I came across a pair of heavy cotton knickers that were a bit big for the pocket then I’d sneak off to the bogs and put them on instead of my underpants, which were then placed in my school bag. I can’t help but wonder what might have happened if I’d been caught wearing stolen knickies!!

As a schoolboy I was fascinated by school knickers and enjoyed nothing more than looking up girls' skirts at every opportunity in the hope of getting a good view. At grammar school all the girls wore navy blue knicks with their winter uniform and white, ones with the summer uniform, which was candy stripe dresses in green, blue and pink. These were of a thin poly-cotton material and it was often possible to see a girl’s white knickers if you were following her with the sun behind you. I soon became an expert at knicker viewing and kept a diary of what I’d seen by way of up-skirts and through skirts. Recalling these events at a later date provided a certain amount of stimulation and if I wore a pair of stolen knickers at the same time the pleasure was multiplied.

By the time I was about 14 I had amassed a collection of about seven pairs of school knickers and I also had a few pairs of nylon panties – they would be called full briefs today, but then they were quite daring. These had mostly been found while out walking, usually close to car parks and must have been the result of late night fumblings. A few pairs had been liberated from a neighbour’s washing line and belonged to the daughter of the house who was a year younger than myself. They were mostly nylon briefs in pastel pinks and blues with cotton gusset and little lace bows at the front. These all provided excellent stimulation and most were worn regularly for wanking sessions. I kept my collection in various places around the house and in late 1968 my parents must have discovered my stash of nylon knickers, for they disappeared. They’d been secreted at the bottom of my bicycle’s saddlebag under a cycle cape and leggings. At least one pair was heavily stained from several good wanking sessions but nothing was ever said. This was the closest I ever came to being discovered with stolen knickers, or in possession of knickers that had stains proving their use for wanking, which would have been much worse.

I used to fantasise about what would happen if I had been caught stealing or wearing knickers at school. The cane was in regular use at that time and I’d had it a couple of times, though only four strokes over my trousers. I’m sure knicker theft would have resulted in a trip to the headmaster and maybe six or eight strokes over sports shorts without underpants. It was always rumoured that the senior mistress, a Scottish lady, punished the girls with a leather tawse. I liked to imagine that in view of my penchant for wearing school knickers that I’d be sent to her for a series of punishments each relating to individual pairs of knickers.

In these fantasies she’d supervise my punishment, having me undress completely and then instructing me to pull on one pair of knickers she’d selected from my collection. I’d be interrogated as to whose knickers they were, where I’d found them, and worse still what I’d used them for. Inevitably I’d end up confessing to masturbating while wearing them and at that point the senior mistress would sentenced me to an appropriate punishment for that pair of knickers. Standing to attention I would be lectured on my masturbatory habits and would be asked which hand I use to pleasure myself. “My right hand Miss,” I’d reply at which point I’d be told to hold it out with my left beneath so that my wanking hand could be given six strokes of the tawse.

Once the hand tawsing was completed I’d be allowed a few minutes to compose myself, before bending over a stool to receive twelve strokes of the tawse over the tightly stretched knickers. In my fantasies I’d try to picture what twelve strokes of the strap, well laid on over cotton school knickers, would feel like and I’d also add a twist to the fantasy by having the mistress discover that I’ve developed an erection during the tawsing. This would result in my having to take the knickers off and face her with a very stiff cock pointing towards her. “I can see that we’re not making an impression here,” she’d say. “Pick up those knickers, give them to me and then kneel on the stool facing me.”

Having given her the knickers I’d mount the stool to await my fate. “Well Michael,” she’s say, “I think you are enjoying this too much. I think we need to let a bit of steam out that penis of yours. Start masturbating very slowly until you are as hard as possible and then I’ll deal with you.” I’d wank myself a little half-heartedly until told to stop. Then the mistress would stand to my right and, using her left hand to grip my penis, she’d pull my foreskin back down my shaft until it became really painful. Despite the pain I’d get a strong feeling that I was about to spunk and would feel my cock starting to spasm. At this point she would place the knickers over the end of my penis to absorb the full impact of my ejaculation. She’d then inspect the sticky mass and declare, “Well that’s best out of you I think; there’s nothing worse than a boy enjoying his punishment session. I think another twelve strokes over your bare bottom may impress on you the seriousness of your offence.”

I’d go over the stool again this time with a bare bum and a softer cock. Twelve well laid on strokes would have me yelling at the top of my voice and hoping that no-one in the corridor outside could hear me. When the leathering was over I’d be invited to don, once again, the damp knickers I’d spunked just minutes earlier and then dress in my school uniform. “You may go now,” she’d say, “But don’t forget that we have another six pairs of knickers here and you’ll have to be disciplined for each pair. Make sure you are here at 3.35 tomorrow afternoon – I’ll give you two strokes extra for each minute you are late. Do you understand?” I’d respond that I did and would leave the punishment room with a throbbing bum and a sore knob in my damp knickers.

Of course this never happened at school but as an adult I’ve managed to play out the fantasy on several occasions with male and female CP enthusiast. There really is nothing quite like a school knicker punishment session especially when enforced masturbation forms part of the punishment.

Do other readers use similar fantasies for masturbation sessions and has anyone else played out the scenario with CP / BDSM friends or professional mistresses?

[nickybrum]

blueunderpants, when i was younger i often wore knickers unders my trousers. if you as my headmaster caught me with a stolen pair in my pocket and asked me to lower my trousers for punishment, what do you think would happen when you saw what i was wearing?

[Simon138]

I have used this scenario of being caught with stolen knickers many times with professional mistresses -school boy and headmistress, lodger and landlady, sailor and senior female officer, stableboy and lady of the manor.

Typically the session would involve being questioned about previous thefts of knickers, punishment for the theft -hands strapped then bottom beaten with various implements and then some humilition from mistress. Spanking usually takes place in knickers - "as you are so fond of womens' knickers you had better put these on". Recently I was made to masturbate into a pair of knickers and thn put them on.