Sissy And The Headmaster

I had been corresponding with Mick for a few months and he had suggested I visit him in his flat in Montagne Street. Our correspondence had been very candid and Mick knew all about my "special desires." Indeed he told me he was very much looking forward to seeing me in my spanking uniform (stockings, suspender belt, lace cami and French Knickers). He didn't tell me much about himself but he did make it clear that he was not especilly interested in any sexual activity. I had been given 10 days notice of our meeting so I had not de-spunked myself for about 14 days prior to our meeting, consequently I was very randy and my balls were heavy with semen. The day prior to our meeting had been spent preparing myself. I spent some time shaving my unwanted pubic hair and my cock and balls were now as smooth as a baby's bottom. My cock especially was much more obvious and stood out more than before. I had also spent some time moisturising my shaved area as well as my bottom. I washed and ironed my uniform and folded it neatly. Finally I packed a small bag filled with the essentials, my uniform.

The day of our meeting arrived and I drove to his flat, managing to park just up the road. I had a small bag with me for my uniform and Mick had told me to arrive promptly at 8pm. I was to ring his bell and when he buzzed me in I was to go to his flat on the top floor. I had arrived early so had a few minutes to compose myself and take stock of our imminent meeting. I was about to have my fantasy of 30+ years fulfilled for the second time; I was minutes away from having my bottom spanked again after a wait of 10+ years. I had written to Mick and told him in some detail my thoughts about an ideal first meeting for me and he agreed that he would use my scenario, plus some role play, for our first meeting. I was hugely excited and as I sat in my car I was physically trembling from my adrenaline rush. I was a 35 year old male in peak physical condition; I was committed to submitting myself to a man I had never met in person and who would soon be putting me over his knee for a spanking. I could not be more excited!

It was rapidly approaching my allotted time so I took my bag, locked the car and went across to Micks front door. I could see his name on one of the bells "M Stern." I checked my watch and at exactly 8pm I pressed the bell. I had to wait for several seconds until I heard the buzz of the door release. I opened the front door and went up the three flights of stairs to the top flat. The door was ajar as Mick had told me it would be. Mick had been clear on what I had to do. I was to close the door and go straight into the spare bedroom where the door had been left open. I quickly did as I had been instructed. I stood in front of the bed in the spare room and collected my thoughts. Mick had told me that at 8.10pm I was to knock on the door to his study (as I entered the flat I noticed that there was a "Knock and Wait" sign on the door immediately to the left of the front door). He had also instructed me to wash myself thoroughly and to dress in my preferred manner. I took a few deep breaths to calm myself before beginning.

I stripped naked and went into the bathroom. There was a clean guest towel and flannel laid out on the sink. I used the soap that was there, a bar of Pears soap. I had never used Pears soap before and I really liked the distinctive scent and plentiful lather. I rinsed my face and thoroughly washed my cock, balls and anus. Having dried myself I returned to the bedroom and put on a black satin suspender belt, a pair of 20den black stockings and a pair of black see-thru French Knickers. I had bought this wardrobe from Axfords, famous for outfitting cross dressers, a few days earlier. The French Knickers were a great find as they were 'full' fitting over my hips but were made of a very light, almost diaphanous, fabric that really was totally see-through. I finished my outfit with a black satin cami with lace trim and spaghetti straps. I had bought this from M&S as it was perfect for my needs; it was extremely short, just reaching the waistband of my suspender belt, as well as being flared at the bottom so it was sort of 'flouncy' when I moved. It was very dainty and feminine. It covered my torso but without panties it offered NO protection to my bottom nor my cock and balls. I quickly checked my appearance and noticed that I only had a couple of seconds remaining to my time-out. I literally ran to Mick's door and knocked...and waited.

My heart was pumping in my chest and my legs were actually trembling. I had my ear pressed tightly against the door so that I wouldn't miss any commands. I heard no sound from the other side of the door and...I waited. All the while I was stood in front of the door my trepidation increased. I had no idea what fate awaited me but I was committed to it and could not back out or change it. The butterflies in my stomach were doing overtime and still...I waited. I was very excited and could not stop myself rubbing and massaging my cock and balls. My cock was semi-flaccid, definitely not erect, and was dribbling pre-cum; there was a distinct damp patch that was clearly visible on the front of my black knickers. As the damp patch increased in size...I waited. I had been outside the door for several minutes and then...

"Enter" I heard the command.

My heart jumped into my mouth and I went into auto mode. I fumbled with the door knob, eventually managing to open the door I went into Mick's study.

"Close the door. Face me. Put your hands on your head." Mick commanded.

I did as I had been ordered and stood in front of the door with my hands on my head facing Mick. I had a short respite and was able to take in the details of my situation. The room was large, about 9m long and 6m wide. Mick was standing at the far end. He was wearing a teachers gown and mortar board which I presumed was part of his role play. Just off to his left side was a substantial armless chair. This was our first meeting; I had no idea of what he looked like as he had not sent me any photos or details about himself. My first impressions were very positive -- he was taller than me with a slim and wiry build. He had 'salt and pepper' hair and sported a 3-day stubble. He was attractive and had a no-nonsense vibe. I placed him in his mid-40s. He certainly met my expectations. He stood in front of me and just looked at me and for the first time I noticed that in his right hand he held a rattan punishment cane which he proceeded to flex in front of himself.

"Turn around" he ordered.

I swiftly did as instructed and stood facing the door with my nose only a couple of centimetres from it. I heard Mick walk across the room and sensed him standing immediately behind me. This was only the second time I had been dressed in my 'spanking uniform' in front of another man. I had toyed with the idea of going without any knickers but decided it would be more humiliating, and therefore more enjoyable, if I started with wearing some and then had to remove them for Mick. I found it extremely exciting to expose myself to Mick and to dress in sexy women's underwear in such a humiliating fashion. I knew he was the dominant Alpha; he knew I was the submissive Beta; I knew I had to do everything he oredered me to do; I knew I had NO choice; I knew I had to obey his every order; I knew that he would soon be spanking me.

"Who sent you to the headmaster's study?" Mick demanded.

This was new to me. Impromptu role play was something I had not done before but I could put two and two together, his dress and the school cane, and surmised that Mick fancied a school scenario. I decided it could be fun.

"Mrs Lambert sent me, Sir" I replied.

"You will address me as 'Mr Stern, Sir'. Is that understood?" asked Mick.

"Yes Mr Stern, Sir I understand." I replied.

"Why did she send you to me? What have you done wrong?" demanded Mick.

"Mr Stern, Sir - Mrs Lambert said that I had forgotten my homework on one too many occasions and that I needed to be punished. She said that only the headmaster could dispense the correct level of discipline and that my bottom should be on the receiving end of a good hard spanking." I replied.

"Very well, I see. In that case we mustn't disappoint Mrs Lambert so I must agree to her request. You will go over my knees for a good hard spanking." Mick said.

"Yes Mr Stern, Sir." I replied.

I heard him walk away. I stood facing the door and knew that my fate was sealed 'a good hard spanking over Mick's knees'. This would be my first spanking at the hands of another person for some considerable time - more than 10 years! I regularly self-spank but it is definitely NOT the same although I am very robust when I spank myself and try to make it sting. I was still facing the door and...waited.

"Come here gurl." Mick commanded.

With my hands still on my head I hurried across the room to where Mick was sat, in what was obviously his spanking chair. He indicated I should stand on his right side. As I stood there I could tell he was looking at the damp patch on my knickers. Mick put his hand on the back of my left knee and moved it slowly up my stocking-clad thigh, past my stocking top until he slid his hand up inside my knickers to squeeze my left cheek. He rubbed, jiggled and pinched my cheek, managing to slide his fingers into and along my crack. I bent my knees slightly to give him easier access to my boi pussy and he immediately pushed a finger tip into my anus. I found this very stimulating and with all the excitement and adrenaline of my pending punishment I was extremely aroused; my balls were literally aching. I was hoping that Mick would speed things up and put me over his knees for my spanking - I was getting desperate!

"Remind me why you are here." said Mick.

"Mr Stern, Sir - Mrs Lambert sent me to you for punishment because I didn't hand in my homework." I replied.

"What punishment did she request?" asked Mick.

"Mr Stern, Sir - she requested that you give me a good hard spanking." I replied.

"We must support Mrs Lambert and I agree to her request. I am going to punish you. You will go over my knees for a 'good hard spanking' on your bottom. You need to know that I am going to video your punishment so that Mrs Lambert can see that you have been disciplined as she requested." Mick explained

"Mr Stern, Sir - yes Sir. Mrs Lambert will be pleased to watch my bottom being spanked." I replied.

Without further ado Mick pushed me forward and guided me over his knees. At last some action! I put my hands on Mick's left thigh, as I did I managed to nudge against his cock and noticed his erection, this was a very good indicator. I lowered myself down so that my hands were flat on the floor and my toes were still on the carpet. My legs were straight. Mick adjusted my position so that my cock was pushing tightly against his right thigh. He did not start my spanking straightaway but decided to enjoy himself by rubbing, pinching, squeezing and slapping my bottom. He soon tired of his caresses and began my spanking.

At first the spanks weren't too hard; firm and regular but not stinging. Mick spanked evenly all over my bottom. My bottom was glowing rather than hurting. The warm sensation and the percussion of the spanks was spreading to between my legs and making me even more aroused. My pre-cum was gushing out of me. Mick gave me only a couple of dozen or so spanks before ordering me up. I was a bit confused as my spanking had been anything but 'a good hard spanking' and more of a very light warm up. Mick stood up and pulled me over to his chair, bending me over the back. My hands were on the seat and my legs were straight and spread. He gave me a dozen spanks before changing my position on the chair, this time my legs straddled the seat and I bent over the back for another dozen spanks. Position change to across seat..position change to kneeling on seat...each position warranted a dozen spanks.

"Get into the corner with your hands on your head." Mick ordered.

I hurried back across the room and went into the corner. I was on display for Mick and found it incredibly sexy to be stood in such a humiliating position. I still wore my knickers but knew they were all but see-through and I was sure Mick would be able to see the results of his efforts. My bottom felt pleasantly warm and I reckon it must have been a light pink colour. It wasn't stinging or burning but the effects of the spanking had spread to my groin! He left me in the corner for a couple of minutes and I wondered what was in store for me. I would be very disappointed if I wasn't spanked again, and a lot harder! In the meantime I...waited.

"Come here gurl." Mick ordered.

I hurried over to him and he immediately grabbed me and guided me down over his knees. I made a big deal of getting in position so that I could get an opportunity to touch his penis. I managed to achieve my goal and I was really pleased to discover that Mick's cock was very hard and very large! My experience of cock is not extensive but as I 'accidentally' put my hand on his cock, on the pretext of steadying myself as I went over his knees, I was able to grab a good feel and was amazed at how big his cock felt. A quantum leap from my package.

He again adjusted my position, this time over his left thigh. He used his right leg to clamp my legs in position. He jammed my left arm tight against his body and he grabbed my right wrist, pulling it up behind my back and locking it in position against the small of my back. My position was not comfortable as I couldn't support my upper torso so my head was dangling unsupported just clear of the carpet. I was bent quite sharply at the waist and my cock was jammed tight against his left thigh. My knees were bent and firmly held in position by his right leg.

He started spanking me again, but this time much harder. His large hand was crashing down with stinging slaps that sent ripples down between my legs. The spanks on my lower cheeks and the tops of my legs were more painful. I writhed around but Mick was holding me securely and despite my struggles there was no escape. The heat in my bottom was quickly rising and it wasn't just my bottom that was getting hotter and hotter, either. Mick's regular spanks had the effect of bouncing my hips up and down and this combined with my squirming and wriggling meant that my cock was rubbing continuously against his left thigh. I found this extraordinarily sexy and ground my cock hard against his leg as much as I was able. I could feel my pre-cum squirting out. This was no warm-up spanking but more of the 'good hard spanking' I had envisaged. I knew that the rosy pink hue of my bottom was changing into more of an angry fire-engine red colour, with a burning feeling to match. The severity and percussion of his spanks was changing the heat in my bottom from a warm glow to a hot stinging sensation and radiating into my groin. I was getting desperate; my balls were aching and I was very near to cumming. My humiliating predicament and the constant stimulation of my cock we're both a BIG turn-on for me and I was seconds away from shooting my spunk all over Mick's trousers.

"Mr Stern, Sir - please stop I am about to cum. PLEASE STOP!" I shouted.

Mick stopped spanking me immediately and pushed me abruptly, and roughly off his lap. I ended up on my knees on the floor but the stimulation on my cock had done its job and although Mick had pushed me away the train of events had taken effect and I felt my clitty shooting my semen onto the floor. I involuntarily squeezed out a couple of ropes of spunk onto the floor. I felt Mick grab me by the ear and drag me to my feet. He marched me back to the corner, pushing me into it; I put my hands on my head and leaned against the wall. Mick put his thumbs into the waistband of my French Knickers and yanked them down to my ankles. My bare well-spanked bottom was now on full display in all its multi-coloured glory - numerous shades of deep reds, purples and many very angry marks.

"How dare you get aroused by your punishment. You are a very naughty gurl. You will lick up your spunk off the floor before I continue your spanking. I have not finished with you yet. I still have to administer your 'good hard spanking'. Now stand in the corner and just think about your imminent punishment." Mick said.

"Mr St..st..stern - Sir. Y..y..yes Sir." I stammered.

I was in a real state. Mick had edged me since my arrival and had just administered a ruined orgasm. I had unloaded some of my stored semen but there was lots more still to cum. My bottom had been well spanked, my most comprehensive spanking to date, and Mick had just informed me that there was more to come. I stood in the corner with my hands on my head, my kickers around my ankles and my well-spanked bare bottom on full display. I found my humiliating situation very arousing and despite my recent 'cumming' my pre-cum was again leaking profusely out of my flaccid cock.

I had thoroughly enjoyed all aspects of my punishment to this point. I had no idea of what to expect at the outset and although the reality was far removed from my fantasy it was much better - the constant humiliation, the spanking, the role play, the uniforms and of course Mr Stern! As I stood in the corner I was getting anxious about my approaching spanking but in an erotic way. I guessed it would be painful but knew I would be forced to submit to it and I found this incredibly sexy!! Also I found Mick very sexy - a strong dominant Alpha male. I am very turned-on by strong Alpha male types and the fact that I felt his cock was erect, and big, was extremely arousing to me. The first, and last, time I had sucked a man's cock was about 10 years previously on the occasion of my spanking from a Master. I was very hopeful that I might be able to suck Mick's cock at some stage.

Although I had a life-long interest in spanking I had only had 4 previous experiences. All of them involved me being spanked with varying degrees of enjoyment, one of them involved me performing oral sex but not to him ejaculating in my mouth. Only one of those meetings had come any where near Mick and I recall being bent over a bench and getting spanked long and hard with a plastic ruler. I had always regretted not finishing my one and only blowjob by getting a mouthful of fresh semen. I wondered if I could persuade Mick to let me suck his cock despite his warning to me that there would be no sexual activity. I thought about how his cock would feel as it expanded in my mouth. I had been practicing on my 'lifelike' dildo for some considerable time. I was confident that I would be able to deep-throat Mick, unless he was huge! In any event I was confident that I could bring him to a very satisfying orgasm. How to achieve and satisfy this craving was the difficult question.

As it was I was still in the corner and still I...waited. My spanking was minutes away but still I...waited. I heard Mick approach me from behind and felt him again grab me by my left ear with his right forefinger and thumb, dragging me back to his spanking chair, I had to shuffle awkwardly to get there with my ankles hobbled by my knickers, and forcing me to my knees. He pushed my head forward and I saw the two ropes of spunk I had ejaculated earlier. They were clearly visible on the wooden floor. He pushed my head down until my nose was on the floor.

"Lick up your spunk gurl. Make sure you get all of it and make sure you clean my floor properly." Mick commanded.

This was not the first time I had tasted my spunk. I regularly drain my semen from a condom after ejaculating. This was the first time I have had to lick up cold spunk but I nevertheless got to work and began lapping the cold semen off the floor. I noticed it was much thinner than usual and wondered if that was because it was only a 'part load' or because it had been on the floor for several minutes. It was academic as I got to work anyway and quickly licked up the cold gooey mess, spending a few minutes licking the floor clean. Mick grabbed my ear and jerked me up. He checked the floor to see if I had licked up all my spunk and cleaned it properly. He seemed satisfied and marched me back to the corner. Again I was stood, in the corner, knickers round my ankles, well-spanked and very red bottom on full display, hands on head...waiting.