Headmaster
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Headmaster free porn video
David, my husband has an older brother, Steven who has two sons, Charlie and Miles with his wife Karen. At the time of this incident, Steven was serving in the British Army based out in Germany, both sons thanks to the Army paying some of the fees, had been educated at UK boarding schools since they were 8 years old, flying out to see their parents at full holiday times, at other times we were their legal guardian in the UK and looked after them on the half term breaks.
Charlie is 2 years old than my elder son Simon, and Simon was just 2 months older than Miles, so naturally Simon and Miles were quite together, almost like brothers. Charlie was a bit of a loner. And my youngest was too young to really play with any of them at all being even younger.
By this time, David and I had been into the new lifestyle 2+ years. I had gone through the phase of fucking everything in trousers (2009/10) and was now comfortable with a small number of lovers playing extreme kinky games and being submissive when that need arose in me.
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In the September of 2011 Charlie was due to change to his senior school; he would have turned 14 by then. My brother-in-law asked if we’d help out; The normal thing in these schools before the actual move is for the parents to meet the school etc, with the prospective pupil, although he’d already been accepted on the basis of examinations, this was for the parents to meet the staff and see the school properly. So in the middle of June, David and l took Charlie out of his prep school to go along to see the new School.
The school was a large 800 pupil boarding school for both sexes from 13 to 18 years of age, although the girls were only about 20% of the population there. It was in an enormous Tudor estate set in Somerset just outside a major town and had been a school for over 150 years at that time. The main house a huge magnificent structure at the end of a mile plus driveway; would have been at some time in the past a home for some Duke, or other wealthy individual and had some many rooms I was always getting lost, various extension had been added over the years.
However back to my story of that day, David had suggested the day before that I ought to ‘tease the old boys a bit’, (we were to meet with the Headmaster and the Housemaster of Charlie’s school, and we’d both assumed they’d be a couple of older men). I hadn’t done any exhibitionistic dares in the presence of my own husband in ages so he was due some real stuff. All of which meant letting someone, at the school openly and deliberately view my naked pussy and/or breasts and by viewing I mean not just a flash of a few seconds, but considerably longer depending on circumstances.
So that morning I had chosen an outfit of a cream blazer jacket over a very lightweight pale yellow summer dress, quite low cut, with 6 largish buttons all the way up the front. I did wear a bra , but a quarter cup one, (that is one which holds my breasts nicely but my nipples and upper breasts are bare, as I wanted my nipples to be prominent against the pale cotton material, also by wearing a light jacket I could button it up if modesty required . I was wearing light tan stockings which were lacy topped hold ups, and naturally was I pantieless. By this date of my own volition, because I’d become accustomed to the sexy sensation, I had virtually stopped wearing any panties or underwear in my normal every day. The skirt part of my dress was loose, (as opposed to being tight) and the hemline fell just above my knees by 3 or 4 inches. Final¬ly I wore a pair of nude open-toe, court shoes with slender 4” high heels and a dainty ankle strap.
When we'd first arrived, a senior boy showed the three of us into the Headmaster’s study. A very large room with a huge book alcove, an enormous oak desk and a few easy chairs to one side, the walls were covered in large photographs of previous school teams, rugby, rowing and cricket. Opposite the alcove was a huge double patio doors leading onto a small patio and looking out over the school playing fields. While we waited, Charlie and David were standing watching a boy's cricket match through the doors and I had sat in one of the easy chairs - a very deep soft leather chair. I had decided that the chair which was very deep was possibly a good place for a bit of leg crossing and uncrossing.
As I said the dress I was wearing had 6 buttons all the way up the front, I had worn this particular dress specifically as I knew what would go on show if some of the buttons were undone. For example, the first button on the top undone would reveal a lot of breast, almost to the nipples, the second one undone and the slightest movement and one or both of my breasts would pop out completely. The 3rd button was level with my navel, and the 4th level with the top of my pussy these two were rarely ever undone, if the 5th and 6th buttons were undone, standing I’d just be decent, but walking I’d be almost flashing my labia lips, with the 5th done up I’d be showing a lot of thigh above my stocking tops. I rarely did the 6th button up it was about 2” above the hem line. That day it was undone before I left the house.
As we arrived at the school and I had got out of our car, David had quickly undone the topmost button, I started to protest and realised I shouldn’t. One thing I’d never experimented with was sitting in a deep armchair in front of a mirror to view what would go on show. I was a little nervous, I knew I was going to deliberately expose myself to one or both of these men in the coming hour or so, I was wet and apprehensive, in my nervous state I didn’t realise I was continuously undoing and doing up that 5th button.
When the Headmaster (Mr Stanley), Charlie's Housemaster (Mr Grayson) came into the library together and as we introduced ourselves, they invited me to stay seated, my 5th button was undone at that moment, but I didn’t realise it. I was struck by how handsome and young (mid 30’s) these two men were, I was quite taken aback, not what I expected at all, I fancied both men straight away -- good looking, well spoken, and with athletic built bodies. Obviously to include me in the conversation they all stood around my chair with the Headmaster standing right in front of me, and the House master and David to one side, but Charlie was right next to the Headmaster.
Much later on, I found out that both the Head and Charlie could clearly see right up my skirt to the tiny puff of blonde pubic curls and when I did cross and uncross my legs, each was treated to a view of my shaven labia lips as well. I hadn’t intended that Charlie be included in my show that afternoon, but the situation that presented itself was making me very aroused, previously when Charlie had peaked at me, I had gained no sexual stimulation at all, but now I knew he was defiantly looking as was the Headmaster, but Charlie was providing most of my arousal, as I was his, of all the guys there, his erection was pushing at his pants.
We talked for about twenty minutes or so, during that time I crossed and uncrossed my legs giving them each a flash each time maybe 4 or 5 times, each time I did it slower than the previous one, what I didn’t realise at that time, was because the 5th button was undone my skirt had slid back a bit and I was flashing part of my pussy region 100% of the time. By this time, both Masters were growing obvious hardons , as Stanley told me later it wasn’t caused just by my exposure to him, but also by the fact that I was ‘showing’ my ‘son’ my parts as well, that turned him on – a lot. Then they invited us to view the school with them,
When it was time for the tour of the school, I had all four sets of male eyes were looking at one thing, in my effort to get out of the deep seated chair, David told me I gave all of them a wonderful and very full view for about 6/7 seconds of my whole cunt as my legs parted, showing my cleanly shaven cunt lips, which were slightly apart and glistening with dew, everything in fact.
It wasn’t totally unintentional on my part, but it was longer and more exposed that I had intended partly because that 5th button was undone, and it was only at that point that I realised the fact. The whole incident induced a big blush making me go quite crimson, but it was for just that sort of reason that I had enjoyed going out knickerless, (as well as being dared to) because there are times when unwillingly and unwit¬tingly, I flash, and I knew they’d all seen and that gave me a big kick and I had apparently struggled to stand up giving the opportunity to stay on view longer, part my thighs wider, to facilitate the sight of my dewy labia.
David whispered to me as we left the study, that my nipples were poking through the thin cotton like the prover¬bial organ stops – after what they all seen, I think that was fairly obvious.
As we walked around the various schoolrooms and then the grounds, I started flirting with the Headmaster like mad and this was meant to be my teasing bit. At one point passing some flower beds, I squatted down to take a better look. Mr Stanley squatted down with me, whilst the rest of them looked on, our knees were nearly touching. l could tell that from his position and his eyes that exactly what I had contrived was happening, with my 5th button still undone, he alone was now getting a good eyeful of my pussy, he must have realised that my exposure was totally voluntary, totally deliberate and much longer, maybe 3 or 4 minutes; My thighs were quite well parted, more importantly, I could tell in his eyes and manner that he knew and I knew that this time it was totally deliberate. He later said my labia was parted and wet.
When the Head stood again, his erection was totally obvious, pressing out like a rod from his grey flannel trousers. My intension was this result, I had achieved what I considered the complete dare from my husband, although, perhaps I ought to have given the other man a full look as well.
It was not long after that, when Matthew, Charlie's future Housemaster, who had spent most of his time talking with David and Charlie, said that we were going over to see the gym and stables, At that point The Headmaster suggested that I might like to return to his study for some tea. David winked at me to one side and insisted that he wished to see every¬thing and that I should return with the Head to the study and they would catch up later. My husband’s intension was clear, he knew and I think probably Matthew as well, that once back in the Head’s study I would get fucked.
When back in his study, we both needed an excuse to go to the next level, when I saw a small collection of canes in a long stand by his desk partly hidden behind an umbrella, teasingly I asked him about the rules on application of Corporal Punishment in the School. Of course at this date rules had been introduced banning such activity in schools and anywhere else. So I led him on to admitting that yes he had canned female pupils in the past that he quite liked canning the older girls especially and yes he missed those days, although even then he had to have parental consent and it was onto bums covered in jogging pants.
Teasing him some more, I asked him if he'd ever canned a girl on my bare bottom, noticing that he was becoming quite flushed by then. Stanley admitted that, yes, he had, once or twice, on “older girls”, his emphasis on ‘older’ gave me the impression that it wasn’t girl pupils. I had by then had picked up one of his canes and was lightly flexing it,
"What sort of thing would merit a girl being caned by you?" I asked. An idea had occurred to me that was causing me to become more aroused, My flashing had aroused and stimulated me, and this new idea this idea was making my arousal more so.
"Well various offenses, breaking rules, that sort of thing" He struggled for a few examples.
"Smoking?" I queried,
"Oh Yes definitely, that would be a full 6 of the best" He replied.
I smiled and winked at Stanley and passed the cane to him,
"Hold this for a moment, will you, I think you'll need it soon". Slowly I turned and reached for my handbag, opening it I extracted a packet of cigarettes and a lighter. I had almost given up but this was a good cause.
"Swearing?"
"Oh err…. yes, depending on the words"
I now had taken a cigarette out and lit it, exhaling a puff of smoke at him.
"FUCK". I said it slow and loud, looking right at him,
"Pardon", His brow was creased in shock and wonder.
"PISS, SHIT, CUNT" I said loudly and slowly as I ran my finger along the cane that he now held loosely between his two hands,
"How many for them?”
There was now a tension building up in the room that was palpable. Looking him right in the eye, I could see that he was desperately deciding whether to or not, was I winding him up or what.
"Three strokes for each word, clearly heard" He had cottoned on but was still unsure. “And of course being caught smoking is usually 6 and a detention.
"So that's eighteen strokes for me, so far" I pointed out, my fingers caressing the cane he still held.
"How many is the most you've ever given in one go? Or what is your maximum allowance?"
Joining in the game now "Six is what the authorities allow, but I don't think that there is a maximum for truly naugh¬ty girls, is there?" He stated.
“I hope not!"
"Well let us see what else you have done wrong", He was more relaxed now, walking around me, "You are wearing too much make up and lipstick, that's another six,"
"I am, improperly dressed I think" as I said that I undid the 2nd button and on cue my left breast popped out of the dress.
"Oh No My dear, Sixth form girls are allowed to wear plain dresses or School uniform and I think I'll introduce a rule that from now on they must give up their underwear, like you have". He paused "But that gives you a total of twenty-four strokes, I think you'll find that enough for any BARE backside". He laid the slim cane against my bared left breast; he slowly drew the tip over my hardened nipple.
"So Mrs. T.... Let's see if you really are as bold as you make out, shall we?"
My answer was to undo the last 2 buttons of my dress and step out of it, leaving me in only my open bra, stockings and high heels; His intake of breath was audible.
On impulse I put my arm around him and pulled his head to mine and kissed him full on the lips, my mouth opening and welcoming his tongue. He responded, by placing his arms around me. His free hand ran up and down my back, cupping my bum cheeks and squeezing one cheek, before, returning up my body and this time cupping my full left breast, feeling it's weight and the hardened nipple on the top.
When I broke the kiss, he went to say something, but I put a finger to his lips and shook my head. I walked over to a low backed arm chair; standing behind it I bent over taking hold of the arm of the chair and thrust my pert bottom at him. He needed no further encouragement.
I was totally aware since we walked in that he hadn't locked the door to his study, also it was a ground floor room with large patio doors, overlooking the sports field, where there was a school cricket match being played. But those boys were really too far away to see, but anyone could have walked past and looked in on us, which included my husband and nephew returning and that added to my excitement.
He struck me harder than I'd actually expected and slower, actually making my gasp. He laid six hard stokes of the cane very carefully on my bum cheeks, he was slow and waited for maybe 15 to 20 seconds to pass between each blow and each blow seemed to land, almost next to the previous strike, I knew straight away that he was no stranger to administering this sort of action. After the first six strokes, he had me go choose another cane and when I turned back he had freed his cock and balls from his baggy trousers and was kneeling on the chair, as I resumed my position my mouth became level with his semi erect penis and without mummer I took it into my mouth as he obviously meant me to.
I sucked upon his cock till he was rampantly hard and then he removed himself and took up his position again. The next six were really hard, almost as hard as I’d ever taken at that stage, and much harder than his first six, and these six were laid across the impact of the first six. Later when I looked at my bum cheeks in a mirror I had an even patch of red rawness about 4” wide across the fattest part of my cheeks and the welts had bled a little, so he’d broken the skin. By now my bum was really burning, but the sensation felt really sexual. When that six were over, I automatically went over and re***********ed another cane, only the third one was bound in leather.
Turning back to Stanley, I found he'd removed his trousers and underpants and was sitting in the chair, but with his legs over the arms, presenting his whole genitalia to me.
"I think you know what to do now,”
I knelt in front of him and once more took his erection into my mouth, this time I licked along the length of his penis, back to the swollen head, licking out the flap of his foreskin and tasting the smegma residing there, enjoying its pungent taste and with the tip of my tongue reaming the crevice, cleaning it all out. Then having sucked his cock to a full erec¬tion with its purple veins standing proud on the pink skin, I then moved onto licking his balls, sucking them individu¬ally, taking one at time entirely into my mouth, rolling each around inside my mouth.
Then, I licked along the crack of his arse and of my own volition I licked into his anal hole, seeing first, then tasting on the outside of his puckered anus the residue of his past excrement that had dried on the wiry hairs, but melted on contact with my saliva juice and assaulted my tongue and aroused me even more by my own wanton lewd act. Fired by the sour taste of his nether region, I thrust my tongue deep, his sphincter mussels relaxed and my tongue was inside him. His rectum was full and my taste buds were assailed by the rancid, vile taste of his shit.
I heard him cry out in pleasure, In the end his body didn’t give him a choice, he could take no more and pulled my head back onto his penis and shot his wad of spunk into my willing mouth. I sucked him till he was limp and he pulled my lips off his limp penis.
He asked me if I still wanted more, yes I did.
This time he had me kneel besides his desk and lay my breasts on the top of his desk, with my arms behind me holding hands per his instruction and my back arched away, I presented my tits for his next canning. Seeing me accept his instructions and clearly knowing his intent, he of course now realised that he wasn't dealing with a wimpish frustrated wife, but someone craving excitement and danger. He now struck across my breasts with a riding crop really hard, telling me that I was a slag and a slut etc. The pauses between strikes were even longer now, possibly half a minute, I longed to rub my burning breasts, but dare not. Watching out of the corner of my eye, I watched amazed as his penis started to erect again. I was now close to crying out with the pain and saying that was enough, but I stuck at it driven by the whole eroticism of the situation.
I wasn’t too sure how many he’d lay on me this time and was not surprised when he didn’t stop at six. He’d started as close to my chest as he dare without striking my face and had moved steadily down towards my hardened nipples as he laid the crop across my white flesh, it stung like hell, finally he laid 4 or 5 very vicious strikes right across my nipples, by which time it was impossible for me not to yelp. Telling me not to let go of my hands but to stand up he now massaged my burning breasts and nipples.
But he wasn’t finished as yet. He now told me to sit on his chair with my legs over the arms, and my bum thrust forward just over the edge of the chair, thus spreading my thighs wide apart. He made me spread my labia lips apart and as I was spreading my pussy for him. I knew what was coming next and whilst I raised no protest, I was concerned at the prospect of being stuck by that whip on my open pussy. Instead he produced from somewhere a ‘cat o’ nine’ tails whip. He slammed it down right onto my parted pussy, “one” he cried out, on the third strike I heard myself cry out ‘oh yes’ or something. At some point on about the 6th strike, still spreading my pussy open, I begged him not to stop and go faster, he complied. Now striking me at about one per 7-8 seconds, I climaxed during the 9th, 10th and 11th strikes; at about 13th I asked him to stop as my climax subsided and I let go my lips, he didn’t stop, at strike 18, I felt my second orgasm arise and it rocked me harder than the first.
On the twenty fifth and final stroke, he pulled me over to his large desk and lying me on my back and with my legs over his shoulders, he fucked my and fucked my hard, I climaxed several times on his steel hard cock, he biting and chewing on my lovely swollen and harden nipples and general¬ly squeezing my sore breasts. All the time telling me that he would love to bind my boobs up as well as the rest of my body, that I must agree to meet with him again etc. which I was agreeing to do. As he built up steam, I whispered in his ear that next time I was going to let him do me properly, he knew instantly exactly what I meant and that I meant it. I felt his cum juice spurt into my pussy as the word sank in to his brain.
Knowing that we may well is up to something and hoping it was very naughty, David had dragged out their remaining tour with Matthew, so that when Charlie and David returned with the form master we had been separated nearly 45 minutes. The Housemaster had seemed strained as the tour continued, and at one point had said “We ought to be getting back to the Head (master’s office)” to which David asked why. The explanation given to one side out of hearing of Charlie was that the Head (Master) had a bit of a reputation as a ladies’ man. David told him that I was very much a Man’s woman and winked, the guy looked positively shocked for about 10 seconds and then he smiled a knowing smile.
Back at the study, my husband could tell by my flushed look that I’d been naughty, but didn't know to what extent; Stanley looked sheepishly at Charlie and David. As he said later the room really smelt of sex and such was plainly obvious that we hadn't merely been chatting over a cup of tea, Matthew looked relieved that we hadn't caught them and that I seemed unperturbed.
We left, with the two Masters saying that they were happy that Charlie seemed to like the school so much. I had to give David a blow by blow account as soon as we were home and in the bedroom, which lead to further sex, my bum and breast marks were really vivid and stayed there for over a week. I wouldn’t say that was my hardest whipping up to that point, I think I felt it more at the time as it happened so fast, I was looking for some exposure fun and sex and suddenly I am whipped and whipped really well.
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Mikayla
- 27.07.2020
- 30
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