A Glass Of Red Wine And A Red Bottom Too: Part One free porn video

My regular meetings with Mrs. Taylor continued into the following year when I was in Sixth Form. Although I hadn’t chosen to do French, I had kept in contact with Wendy and we managed to see one another outside school every four to six weeks, depending whether or not her husband was home. I was spanked each time, having confessed to Auntie Wendy what I had failed to do over the previous few weeks or for admitting having misbehaved or for simply making things up. Generally, this was my admission how many times I had masturbated at the thought of Wendy or some of her female colleagues at my school.

The spankings had been real punishment spankings and had hurt, just as my first ever trip over her sturdy lap had. We had then gone up to Mrs. Taylor’s bedroom, where we had spent hours pleasuring one another. During one such time in her lovely king-sized double bed, she had asked me which other female members of staff I fantasized about or had been punished by, and I had answered her honestly, knowing that she probably already knew the answer. There were five, including Mrs. Taylor, and she smiled at me as she slowly masturbated my throbbing cock in her right hand for the second time that night.

“I’ll see what I can arrange – maybe I can get them all to come over here one night and they can take turns in smacking your naughty little bottom, young man,” she had replied.

And so, here I was. Standing in Wendy Taylor’s impressive living room, totally naked, facing the wall with my hands on my head. My nose was touching the cold wall in front of me and I awaited my latest punishment with Wendy. As I stood there, I heard two cars pull up outside within five minutes of one another and the doorbell rang twice as the guests arrived. Mrs. Taylor came from her kitchen and answered the door, greeting the women before they went into her large kitchen where Wendy was obviously inviting them to have a glass of wine and to help themselves to the snacks that she had prepared.

I had no idea how many women were in Wendy’s kitchen, and strained to hear the ladies chatting to see if I could recognise their voices. It took me a while, but I guessed that my History Mistress, Miss Manson; Mrs. Wardell, the Food Technology teacher, who I had upset several months previously; Miss Walton, my old Maths Mistress, who had smacked my hands with her ruler, and Rachel Lindley, the lesbian PE Mistress were the women who had turned up. My cock began to swell at the thought of maybe being slippered by the muscular and athletic semi-professional hockey player.

After approximately thirty minutes’ corner time, I heard the ladies walking from the kitchen and within moments, they were standing behind me. I remained silent and closed my eyes, resisting the temptation to turn around and look to see who was there. They said nothing and Wendy walked up to me and stood to my right-hand side. She deliberately brushed against my bare skin, her azure blue long-sleeved blouse making me gasp as it touched my bare skin. Mrs. Taylor’s perfume was strong, and her cool breath blew against my chest as she reached down with her left hand. Initially, she began stroking my inner thighs before taking hold of my cock, which began to swell at the thought of what Mrs. Taylor was doing to me with her hand.

The other women in the room watched in silence as my French Mistress continued to slowly masturbate me with her left hand, before reaching over with her right, with which she began stroking my balls. Miss smiled to herself as she ran the index finger on her right hand up the length of my bum crack and to my anus, repeating this several times as she listened to my breathing becoming heavier and heavier as I became more and more aroused. Wendy continued touching my cock and balls for several minutes before she stopped and removed her hands, turning her attention back to the ladies who were standing watching her.

“So glad you could make it tonight, ladies. Peter made it very clear to me which of his teachers he wouldn’t mind a spanking from and thankfully most of you could make it to teach this naughty little boy a lesson that he won’t be forgetting in a hurry,” Mrs. Taylor spoke softly.

“Such a shame that Jessica and Sylvia couldn’t make it tonight,” she added as she walked over to where the others were standing.

“I know how much they were both looking forward to joining in tonight.” She picked up her glass of wine from the table and took a sip from the glass.

“Sylvia had to babysit her new baby niece and Jessica said that she was going out for a meal with her family, but otherwise they would have come – Sylvia especially wanted to punish this one seen as she has a long unresolved issue with him from when he was in the lower school,” a voice answered.

I recognised it immediately as Mrs. Wardell.

“Perhaps we should ask this one here about what that issue is?” Miss Manson chipped in.

My cock was fully hard by this point and was proudly pointing at Wendy’s wall in her large living room.

“Please sit down, ladies, and we can decide how we’ll punish this naughty young man and who will spank him with what,” my French Mistress laughed.

My female teachers chatted about my previous punishments from them at school and what they would like to use on me that evening as if I weren’t there. I remained silent, facing the wall with my hands on my head as they continued to chat. After a while, their plan had been worked out and my punishment was drawing near. The ladies continued to chat amongst themselves whilst Wendy left the room, returning a few minutes later with her collection of implements. She placed these on her dining room table and moved one of her padded, high-backed dining room chairs into a space in the living room.

“So, ladies. I think that it is time to begin,” she laughed as she walked back over to where I was facing the wall.

She began by stroking my back with her left hand, which she ran slowly up and down the length of my back several times.

“Now, seen as we’re at home and not in school, you shall refer to your disciplinarians as “Auntie.” Am I making myself clear, Peter?” Wendy asked, still stroking my back softly with the fingernails on her left hand.

“Yes. Auntie Wendy,” I replied almost in a whisper.

“Right, young man. You’re going to be punished by all of us tonight – first by Auntie Jane, then Auntie Pauline, Auntie Louise, Auntie Rachel and then by me.” Mrs. Taylor brushed her blue satin blouse against my bare back.

“And to conclude your punishment, and because you have been so naughty, you will be given six of the best with the cane from each of us – that will be thirty strokes of the cane in total, and if you don’t behave yourself while being caned, then we’ll give you extra. Do you understand me, you bad, bad boy!” she hissed in my ear.

“Yes, Auntie Wendy,” I replied quietly, aware that I was close to shooting my load as the sensation of feeling her satin blouse touching me was sending me into ecstasy.

Mrs. Taylor looked over at the ladies who were sat on her sofa and her two armchairs, continuing to stroke my back gently with her left hand as she did so. She looked down at my erect cock and smiled at her friends.

“Auntie Jane. Would you like to warm his bottom up for what is to come tonight, seen as according to our naughty nephew here, you hand spank the hardest?” Wendy asked.

The dark-haired Food Technology teacher smiled and got up from the armchair. She walked across to Wendy’s dining room chair that had been placed in a space between the living room and dining room and ironed the creases from her long, three-quarter length white pleated skirt before sitting down on the black leather padded chair. Jane Wardell continued to adjust the sleeves on her long-sleeved silky magenta blouse, rolling both sleeves up until she was satisfied. She then sat back in the chair and placed her hands in her lap and waited for me to walk over to her.

“Don’t worry, Auntie Wendy. The mood I’m in with this young man will ensure that his bottom and the backs of his legs will be thoroughly warmed by the time I’m finished with him,” Jane answered sternly.

Wendy Taylor laughed and took hold of my right arm with her left and began leading me towards Mrs. Wardell, who stared at me, a thoroughly angry look on her face.

“Would any of you ladies like a closer look at this naughty young man’s cock, before we begin?” Wendy laughed as she asked as she pulled me towards Jane.

The women all laughed and within a second I was standing in front of Louise Walton, my former Maths teacher, cock pointing proudly out in front of me. It stood there within inches of her face as she sat on the armchair. I tried to avoid looking at her in her short-sleeved white cotton blouse and navy three-quarter-length skirt. I closed my eyes and hoped that I wouldn’t go off on her clothes and gasped as I felt her large powerful hands touching my cock and balls softly. Auntie Wendy allowed her to continue touching me for a few moments before leading me across to her sofa, where Pauline and Rachel sat.

Again, I was held in position by my French Mistress as first, Pauline touched and stroked my cock and balls before being led the short distance to Rachel, who took great delight in touching and fondling my private parts.

“Ooh, it’s just like a lollipop, isn’t it, ladies – crying out for a nice long lick and suck!” she exclaimed, bursting out into a fit of laughter.

The other women joined her, and Wendy began stroking my bare bottom with her left hand.

“Well, Auntie Rachel. I never thought I’d hear those words coming out of your mouth, but if you wanted to give the lollipop a little lick, then I’m sure our naughty boy wouldn’t mind,” she said as she pushed me closer to Rachel, who was leaning over so that my cock was almost touching her face.

After a moment’s hesitation, I opened my eyes, just as Miss Lindley licked the tip of my cock with her tongue before opening her mouth and taking it inside until about half of its eight-inch length was inside her warm mouth.

“Rachel!” Louise Walton screamed, a mixture of surprise and disgust in her tone.

“Mmmmmmmm!” Rachel Lindley kept me in her mouth for a few moments before she pulled back and my hard cock came out of her mouth.

I stood there, looking down at Miss Lindley in sheer shock. It was well known at school that she was a lesbian who spanked any misbehaving girls with the plimsoll. So, having my cock taken inside her mouth totally blew me away. She continued to stare at my fully hard cock as I stood facing her, looking down at her long-sleeved jade green cotton blouse and white trousers.

“Maybe if you’re a good boy and take your punishment like a good boy, then Auntie Rachel may soothe you if you ask her nicely,” Wendy whispered in my right ear as she led me over to where Jane was sitting.

The other three women had all picked up their wine glasses as I stood at Mrs. Wardell’s right-hand side. Wendy had stepped back, standing there with her arms folded across her chest.

“Auntie Jane. Over to you,” she spoke softly and watched as Mrs. Wardell shuffled around on the chair.

“Right. You know the routine, young man. Over my knee, hands flat on the floor in front of you and feet touching the floor behind you,” Jane instructed coldly and removed her hands from her lap and invited me to position myself over her lap.

I carefully tried to avoid looking at the lady with the shoulder-length dark brown hair as I stepped over to her and reached over her white pleated skirt until I felt my crotch touching the material of her long skirt. I placed my hands flat on the floor and gently pushed my feet down until they touched the carpeted floor behind me. The next sensation I felt was Jane Wardell’s hand being placed flat on my lower back.

“Open those legs slightly, young man,” she instructed firmly, and I immediately complied.

Out of my sight, Wendy walked away, picked her wine glass up and sat down on one of her armchairs. The other ladies leaned forward in their seats and settled in for what they were about to witness.

Mrs. Wardell, the forty-two-year-old Food Technology Mistress, smiled at her friends as she lifted her right hand from my back and began rubbing my bare bottom and the backs of my legs gently. Upon feeling her warm hand touching my skin, I pushed my crotch down into her lap, my bottom rising a little further into the air.

“Now, you, naughty, naughty boy. Auntie Jane is going to warm that bottom of yours and she will not stop until she is satisfied, no matter how much you cry, scream, shout or plead. Do you understand me, Peter?” she spoke softly as she continued rubbing my bottom and thighs.

I nodded and then turned my head to the left to look up at her.

“Yes, Miss – I mean, Auntie Jane.” I returned my face to looking down at the carpet and awaited my spanking to begin.

“I’m going to tan your bottom so severely this evening so that you never, ever behave like that again, young man!” she snapped.

She raised her small right hand in the air and paused, looking across at her friends. Wendy Taylor nodded at her. It was time to begin.

“Let me make one thing clear to you, young man. If you dribble or have an accident on my lovely skirt, then I will take Rachel’s plimsoll and beat you black and blue with it. Am I making myself clear?” she hissed before looking across at the PE Mistress.

“Yes, Miss. I mean, Auntie Jane,” I gasped, unintentionally pushing my cock further against the older woman’s pleated skirt.

Jane Wardell felt my cock prodding against her right leg and smiled. The thought of having me lying over her lap was really turning her on and she could feel her juices flowing between her legs.

“Very well, young man. We shall begin. Take your spanking like a good little boy. You deserve each and every smack I am going to give you this evening.” She licked her lips and took a deep breath.

A moment later, Mrs. Wardell’s small, but deceptively hard, right hand connected across the fleshy centre of my muscular bottom. The sound it made echoed loudly around Wendy’s large living room.

“Slap!”

My buttocks wobbled as Jane’s hand connected across the centre of my right buttock, but I managed to stay in position, avoiding squirming and wriggling around too much as the pain registered in my brain. The forty-two-year-old teacher smiled at her friends as she slipped her left arm under my stomach and around my waist, pulling me tightly into her silky blouse and pleated white skirt. The cold buttons on her magenta blouse rubbed against my skin and I inhaled her sweet perfume as she readied herself to punish.

“Tan his arse, Jane!” Miss Walton instructed sternly.

Mrs. Wardell didn’t make me wait long until the onslaught began.

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

The older woman slowly and methodically laid out two dozen full-force slaps across the centre of my bottom, not saying a word as she did so. The only thing I heard or felt was the teacher tightening her grip around my waist before administering a second dose with her very hard hand.

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

This second visit built upon her first, and the heat began to grow in my backside, but I was going nowhere. The slightly-built teacher simply held me into her skirt and blouse and continued her work.

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

Another slow and painful visit began to turn my pale bottom a shade of pink, but Jane was far from satisfied, or finished, with me. The heat continued to build in my bottom as the Food Technology Mistress concentrated upon spanking every single inch of my muscular bottom.

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

By this point, Jane’s hand had started to hit the spot and I had tears in my eyes. My backside was a deep shade of pink, every inch having received a visit from the teacher’s hard right hand. I pushed myself deeper against Mrs. Wardell’s skirt, prodding her covered right leg with my erect cock.

“Woe betide you if you squirt on my skirt, young man!” she hissed, before bringing her hand down once again.

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

This time, Jane Wardell aimed for the creases in between my bum cheeks and thighs, each stinging slap bringing more tears to my eyes. As I squirmed around on her lap, trying to avoid her hand, I dribbled some pre-cum on her pleated skirt and it did not take her long to realise what I had done. She paused and used her right hand to reach under me and touch her skirt. She was indeed damp. Partially from me, but also from her sweat and juices building from her exertions, but I was going to pay for it most severely.

“Can one of you ladies come over here and help for a few moments?” she asked calmly.

It was Auntie Rachel who got up from the sofa and walked over to where I was lying over Jane’s lap. I looked up through teary eyes and saw Miss Lindley standing in front of me in her white trousers and green blouse.

“Can you straddle his shoulders, Miss, so that he won’t move around while I finish his spanking?” Mrs. Wardell replaced her right hand on my burning bottom and adjusted the grip she had with her left arm around my waist to hold me securely.

The PE Mistress with the short brown hair carefully straddled me, ensuring that she pushed her weight down on my shoulders. She closed her muscular thighs gently around my shoulders until I groaned. I was going nowhere, and, out of my view, Jane Wardell took aim for the finale to her part of my punishment.

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

Mrs. Wardell wrapped out a rapid-fire hand spanking across my bottom which covered absolutely every inch of it.

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

The frantic spanking continued for about two minutes, by which time, I was crying and pleading for Miss to stop. Those pleas fell on deaf ears as Auntie Jane dished out another quick-fire dose.

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

Once Jane had decided that enough was enough, she placed her right hand against the creases in between my right bum cheek and thigh.

“Right. Just to teach you a lesson, young man, Auntie Jane is going to give you twenty-four smacks on the backs of your legs. And you can cry and sniff and sob and plead all you want, because I’m going to spank you until I’m happy,” she whispered and waited as Rachel adjusted her stance, squeezing me even tighter between her powerful thighs, her large bottom resting heavily on my shoulders.

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

Twenty-four slow and full-force slaps landed alternately across my thighs and backs of my legs, quickly turning them a dark shade of red.

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

“Slap!” “Slap!” “Slap!” “Slap!” “Slap!” “Slap!”

Auntie Jane concluded her part of the punishment, and my warm-up, with an identical, unexpected and additional dose, which had ignited a fire across my lower bottom and thighs.

The forty-two-year-old removed her left arm from around my waist and placed both hands flat on my bare back. She laughed softly as she listened to me sniffing and sobbing before looking over at the other ladies in the living room. After a few moments, Rachel opened her legs and released the grip that she had had around my shoulders with her powerful thighs. She carefully stepped off me but not before playfully pushing her covered bottom against my face. All I could do was drip more tears against her white cotton trousers.

Mrs. Wardell sat looking at the other ladies as I lay across her lap. After a few minutes, when I had sniffed, sobbed and dripped more tears onto Mrs. Taylor’s carpet, Auntie Jane began gently rubbing my hot and sore bottom and thighs with her right hand. She didn’t say a word as her hand wandered over every inch of my tender bum cheeks and the backs of my legs, which had received their painful share of the dark-haired teacher’s hand. Once she had decided that I had been soothed enough, Jane slipped her right hand under my waist and immediately searched for my cock, finding it in no time at all. The forty-two-year-old smiled at her friends as she felt the wet tip of my cock.

“He’s dribbled on my skirt, ladies,” she said, shaking her head as she removed her right hand, replacing it on my back.

“Oh dear, Auntie Jane,” Miss Walton laughed.

Jane Wardell flicked her dark hair behind her left ear with her left hand.

“Just you wait until we get to the caning, young man. I’m going to really make you suffer for dribbling on my skirt,” she leaned forward and whispered in my ear before replacing her right hand on my bottom to give it one last soothing rub.

“Up!” she hissed and sat back in the chair, moving her arms from my back to allow me to get to my feet.

I lay over her pleated-skirt-covered knees for a few moments before struggling to my feet. I stood looking down at Jane, who looked up at me with a totally pissed off look across her face. She looked at me, then down at her damp skirt, before back to me. Mrs. Wardell carefully got to her feet and brushed past me before walking across to the sofa, where both Pauline and Rachel had stood up.

“Perhaps you’d like to clean him up, Auntie Rachel before he goes over Auntie Pauline’s knees for the clothes brush,” Wendy laughed from her armchair.

Pauline Manson walked past me and headed into the dining room, where she picked up her small, ebony-backed clothes brush. She turned around and watched as Rachel Lindley got on her knees in front of me and began licking my cock once more. Again, she took my throbbing cock inside her warm mouth before pulling it out slowly, licking it while touching my balls. She continued doing this for a few minutes, during which time, my History Mistress had adjusted her skirt and blouse and replaced Mrs. Wardell on the high-backed dining room chair, the clothes brush held proudly in her right hand.

“Are you quite finished, Rachel? Is the naughty boy clean?” Miss Manson laughed as she watched the muscular girls’ PE Mistress kissing and touching my cock and balls across from where she was seated.

Miss Lindley smiled as she got to her feet and adjusted her jade green blouse, before retaking her seat on the sofa.

“Sorry. It seems that I get easily carried away with his cock – it’s so much better than sucking on my girlfriend’s rubber strap on. It tastes nicer too!” she laughed.

The other ladies joined in.

Pauline Manson turned her full attention to me as I stood next to where she sat on the chair. She began tapping the clothes brush gently against the palm of her right hand, staring at me as she did so.

“I’m sure you’re aware of what is coming your way now, young man, seen as I’ve done this to you before, so we shall waste no more time. Come and get over my knee and, like Auntie Jane, no little accidents on my lovely skirt, or like Auntie Jane promised – your naughty little bottom will suffer for it. Am I making myself clear?” She raised her voice to emphasize those last five words.

I nodded and began moving across until I was standing to her right-hand side.

“Yes, Auntie Pauline. I’m sorry, Auntie – I’ll try not to go off on you, Auntie Pauline,” I spoke in gasps.

The other women laughed at my last comment.

“Go off? What a filthy little beast!” Louise Walton snapped.

Pauline looked up at me, a stern, no-nonsense look on her face.

“Over you go. Hands flat on the floor, legs open slightly and toes touching the floor.” She stopped tapping the brush against the palm of her right hand and sat back in the chair.

“Over!” She raised her voice.

I looked over at Rachel, who was sitting on the sofa, sipping her glass of wine. She smiled at me before I turned my full attention back to my History Mistress. She looked at me, emotionless, as I reached over her and lowered myself down until my bare crotch touched Pauline’s camel-coloured knee-length skirt. I rested my hard cock against her right leg and reached over until my hands were flat on the floor in front of me. My toes touched the carpet behind me, and I shuffled around until my legs were open, closing my eyes in anticipation of what was coming my way. I had been spanked once before by Pauline with her wicked little brush and knew how much it hurt.

Pauline Manson took a few deep breaths and moved around on the padded chair until she was comfortable with the position I was in over her knees. Her short skirt had risen up and my cock touched her silky smooth right thigh. Once again, it did not take long before my pre-cum had started and began to dribble on her right leg. I tried to prepare myself for what was coming my way as I felt Pauline’s left arm reaching under my stomach and pulling me gently into her skirt and blouse until I was held securely in place. My History Mistress smiled at the other ladies in the room as she ran the small, oval-headed, ebony-backed clothes brush over every inch of my already sore and red bottom.

“How many smacks, Auntie Wendy?” she asked.

Mrs. Taylor took a few moments to answer as she was busy unbuttoning the top three buttons on her long-sleeved azure blue satin blouse, and also because she wasn’t paying full attention to what the woman with the short brown hair was doing.

“Oh, erm. I hadn’t thought of a number, Auntie Pauline. Perhaps just spank his naughty bottom until you are satisfied that he has learned his lesson. Perhaps spank him for all those times you’ve “had” to give him a detention for his bad behaviour?” Wendy emphasized the word had, as she knew the detentions had all been set up by Pauline and that I had not done anything wrong at all to deserve them.

Miss Manson laughed softly and stopped rubbing her brush against my buttocks, lifting it in the air with her small right hand.

“Very well, Auntie Wendy. I feel like spanking him into next week after his constant bad behaviour. Plus the fact that he obviously seems to enjoy being spanked,” she hissed, looking over at Jane and then down at me, just as I prodded my throbbing cock hard against Pauline’s bare thigh.

Miss Manson tightened the grip that she had on me with her left arm before tapping the brush softly against my already red and sore bottom.

“Now, young man. I’m going to spank you with the clothes brush and you’re going to take each and every smack with as little fuss as possible,” she spoke sternly.

“If you move, or cause me any issues, then I’ll leg lock you and start all over again and beat you until you can’t sit down. Do you understand, Peter?” she continued.

I nodded my head at the carpet in front of me, dreading the brush. I knew exactly how much it hurt when used by my History Mistress.

“Yes, Auntie Pauline. I’ll be good. I promise.” I spoke almost in a whisper.

I had hardly got my words out before Pauline’s first smack with her evil little clothes brush landed hard across the fleshy centre of my bottom.

“Smack!”

The pain immediately hit home, and I was reminded of my most recent, and most painful detention in Pauline’s classroom, where she had smacked my bottom frantically and as hard as she physically could with her brush. I wriggled around on her knee as the pain registered in my brain, but the disciplinarian skilfully used all her strength in her left arm to hold me in position.

“Oh, no you don’t, you, naughty, naughty boy! You’re not going anywhere until Auntie Pauline has shown you how displeased she is with your behaviour and how she’ll deal with you if your behaviour doesn’t improve in future,” she purred, obviously enjoying what she was about to do.

After a few moments, I settled across her lap and the ebony-backed clothes brush began to do its painful work across my bottom and backs of my legs.

“Smack!” “Smack!” “Smack!” “Smack!” “Smack!” “Smack!”

My History Mistress expertly laid out half a dozen slow, and extremely hard, swipes with her nasty little ebony-backed brush across the lower part of my bum cheeks. She paused each time I struggled and squirmed as her small, oval-headed brush ignited a fire across my bottom. Once I had settled, Pauline resumed the task in hand, calmly laying out twelve more slaps with her brush, landing them alternately across my left and right buttocks.

“Smack!” “Smack!” “Smack!” “Smack!” “Smack!” “Smack!”

“Smack!” “Smack!” “Smack!” “Smack!” “Smack!” “Smack!”

My tears had started falling onto the carpet below once again and I found that the more I wriggled and squirmed on Pauline’s knees, the more that the forty-four-year-old teacher tightened the grip she had with her left arm around my waist, pulling me into her dark, Prussian blue, cotton blouse with its cold buttons.

“You bad, bad, boy!” she hissed before smacking my burning backside another dozen times, again, using her clothes brush to tan both bum cheeks alternately.

“Smack!” “Smack!” “Smack!” “Smack!” “Smack!” “Smack!”

“Smack!” “Smack!” “Smack!” “Smack!” “Smack!” “Smack!”

“I’ll teach you a lesson that you won’t be forgetting in a hurry, my boy!” Pauline announced sternly as she allowed me to calm myself.

“Smack!” “Smack!” “Smack!” “Smack!” “Smack!” “Smack!”

“Smack!” “Smack!” “Smack!” “Smack!” “Smack!” “Smack!”

Another slow and painful dose of Auntie Pauline’s clothes brush began to bruise my already red and sore bottom, the shades of red becoming deeper the more the mature woman beat me with her brush. She ignored my cries and sniffs, becoming more and more aroused as she felt my cock being pushed against her bare right thigh as I moved about to try and escape the punishment. The dark-haired lady paused as she felt herself becoming hot from her exertions and also from the fact that she knew she was damp between her legs from having my cock brushing her leg.

“Dirty beast! Don’t you dare squirt on me like you did on poor Tina!” She raised her voice and looked across at her audience.

“That’s right, young man. Everyone here knows about you and poor Tina and how you squirted all over her when she touched that thing.” Auntie Pauline shuffled around on the padded dining room chair and once comfortable, she began tapping my battered bum cheeks with her small clothes brush.

I have no idea why I did what I did next, but it was swiftly, and efficiently, dealt with by Pauline Manson. I began to shout and plead with my History Mistress. How I’d be good in future. How I would behave myself if only she’d stop spanking me. Miss Manson ignored me and took aim with the brush but stopped suddenly when I threw my right arm up from the floor and placed it across my bottom to stop her beating me. The forty-four-year-old took this in her stride and simply brought her left arm out from around my waist and grabbed my right arm in her left hand and pinned it painfully against my back.

“Oh no, Peter. We’re not finished yet and I’m going to spank your botty with my brush until I know that you won’t be misbehaving for me in future.” The ebony-backed clothes brush was tapped against my swollen bum cheeks once more.

“So, go on, young man. Have a little cry and a sniff because Auntie Pauline doesn’t care. All she is going to do is teach you a lesson that you won’t forget in a hurry!” she snapped, bringing the brush down against the centre of my muscular bottom a moment later.

“Smack!”

My tears began flowing freely onto the carpet below and I began to cry. Pauline simply smiled at the other ladies in the living room and concluded her part of my punishment, laying out a further two dozen slow and painful smacks with her nasty wooden brush, despite me struggling and wriggling around on her knee. The more I struggled, the tighter she gripped my right hand with her left, forcing it higher up my back until I was forced to stop moving due to the pain it was causing.

“Smack!” “Smack!” “Smack!” “Smack!” “Smack!” “Smack!”

“Smack!” “Smack!” “Smack!” “Smack!” “Smack!” “Smack!”

She paused briefly after the first dozen smacks to inspect my bottom and to adjust her position on the dining room chair before she prepared to administer her final twelve smacks with her brush.

“You won’t be sitting for a week once I’m through with you, young man!” Miss Manson took aim against the lower part of my buttocks and the tops of my thighs.

“These are for dribbling on my thigh,” she spoke in her strict, teacherly tone.

Moments later, she laid out those final twelve smacks with her clothes brush, hard and fast, deliberately catching my lower buttocks and the creases in between my bum cheeks and the tops of my thighs.

“Smack!” “Smack!” “Smack!” “Smack!” “Smack!” “Smack!”

“Smack!” “Smack!” “Smack!” “Smack!” “Smack!” “Smack!”

Once she had completed her part of my punishment, Auntie Pauline sat there, continuing to hold me securely in place over her knee until I had settled down. I sniffed and sobbed loudly, not caring that the ladies could hear me. After a few minutes, Pauline Manson released the grip that she had on my right arm and once she had let go, it fell back down to the floor. My cock was still almost solid and continuing to drip pre-cum on Miss Manson’s silky smooth right leg.

“Up!” Pauline instructed.

I took a few moments to comply before struggling to my feet and standing before her. I wiped my nose and my eyes with both hands, not looking at any of the ladies who were watching this spectacle. Miss Manson got up from her chair and walked into the dining room, where she laid her ebony-backed clothes brush down on the dining table before returning to the living room and picking up her glass of wine from the coffee table. She smiled as Wendy got to her feet and walked up to me.

As Pauline sat in the seat vacated by Auntie Wendy, Mrs. Taylor got on her knees before me and placed her hands on my hips, the silky material of her satin, azure blue blouse brushing against my bare skin. The older woman then moved her head slightly and opened her mouth, taking my almost hard cock inside her warm mouth. She began moving her head backwards and forwards, licking and sucking on my cock until she had me on the point of climax.

“Auntie Wendy,” I gasped.

Mrs. Taylor ignored me and simply grabbed onto my hips even tighter, continuing to work away at my cock with her mouth. After a few more seconds, I gasped and shuddered, sending a squirt of spunk deep inside my French teacher’s mouth. This was almost instantly followed by a second squirt, which Wendy gratefully accepted. She swallowed and kept my cock in her warm mouth for a while. She removed her hands from my hips and slowly slipped my cock out of her mouth. Once it was out, she took it in her left hand and spent a few minutes licking it clean, not stopping until she was absolutely sure that every inch of it had felt her tongue.

Wendy remained kneeling on the floor, holding my by now flaccid cock in her hand. Jane had got up from her seat and taken Louise and Rachel’s empty wine glasses into the kitchen, returning a few minutes later with the glasses filled once more. She placed them down on the coffee table and smiled as Wendy got to her feet and led me into the dining room, where I stood facing the large dining room table with the remaining implements laid out on the far side. After a few moments, I could sense that the ladies were all standing behind me, eager to get a closer look at the next part of my punishment. These were going to be administered by Louise and Rachel, and I knew that they were going to hurt.

“Now, young man. You asked for Auntie Louise tonight because she smacked your hands with her wooden ruler when you were in the lower school. Is that correct?” Mrs. Taylor asked softly.

I simply nodded, giving the occasional sniff and sob as I tried desperately to calm myself from what had happened earlier.

“And you received the ruler because you asked to move seats, thereby messing up Auntie Louise’s alphabetical seating plan,” Wendy continued.

Again, I nodded in response.

“And, when I asked about which teachers you fantasized about, Auntie Louise was one of them. In fact, ladies, Peter said that he wanted to see her breasts and feel her hand on his cock. Well, at least you’ve already achieved one of those ambitions tonight, you dirty little boy!” She raised her voice slightly.

From behind me, Louise Walton walked past Wendy and myself and stood at the opposite end of the dining table, surveying the collection of spanking implements that had been laid out. She smiled at me angelically as she picked up the large, wooden American-style spanking paddle with the eight round holes running down its length in two sets of four.

“Will he see your breasts tonight, Auntie Louise?” Wendy Taylor laughed as she gently stroked my warm bottom with her right hand.

Miss Walton walked the short distance until she was standing to Wendy’s left-hand side and shook her head.

“All this little pervert is going to feel is how displeased I am with him and his grubby little fantasy,” she replied angrily.

“Oh, dear. So no breasts then, Miss?” Mrs. Taylor joked.

Louise began tapping the heavy piece of wood against the palm of her large left hand.

“I can’t believe that during the year I taught him, that all he was doing was thinking about me dressed in my blouse and skirt and what he’d like me to do to him. He probably even got off on having the ruler put across the palms of his hands in front of the class,” Louise spoke with a stern tone of voice.

I truly was in for a whacking of biblical proportions. She was not going to simply give me a play spanking. I began to regret telling Wendy that she was one of the ladies who I wanted to be punished by.

“So, what are you going to give him, Miss Walton?” Wendy said as she continued to stroke my bottom with her hand.

The young Maths teacher looked at her and then focused on me. She was either thoroughly pissed off or just a damned good actress. I was terrified.

“Well, I’m going to wallop his bare bottom with the spanking paddle – twenty-four swats, I think, and I’m going to give them as hard as I physically can, so that if he ever thinks about me again, then all he’ll be reminded of is how sore his backside was once I had paddled him,” she explained whilst tapping the paddle against the palm of her left hand and continuing to stare at me.

“Over the table?” my French Mistress asked quietly.

Louise nodded at her and took a step to the side.

“Very well, young man. Bend yourself over the table – right over, spread those legs wide. Jane. Pauline. Would you mind standing at the far end of the table and holding him down?” she said, smiling as she looked back at Mrs. Wardell and Miss Manson.

Pauline Manson and Jane Wardell took a sip of wine from their glasses before placing them down and joining Wendy, Louise and me in the dining room. Auntie Wendy gently and carefully led me to her large dining table and carefully helped me bend over until my arms reached over the table almost reaching the far side. Behind me, she softly tapped my inner thighs with her right hand, instructing me to spread my legs, only stopping the gentle slaps with her hand when she was satisfied that my legs were open wide enough. In front of me, Jane stood at my left side and Pauline to my right, each grabbing an outstretched arm in one hand and placing their other on my lower back. I was going nowhere.

And I was going to get the walloping of my life from Louise.

Auntie Wendy stepped to one side and watched carefully as my ex-Maths teacher took up her position to my left-hand side. She kicked off her navy high-heeled shoes and placed her left hand on her left hip. She smiled across at Pauline and Jane, who were watching her, before she bent her left knee slightly and laid the heavy and large wooden paddle flat against my already red and swollen buttocks.

“Now, young man. I want you to think about every whack I give you this evening. Why you are being whacked and what will happen to you in the future if you continue to be a bad, bad boy. Do you understand me?” She lifted the paddle from my bottom and waited.

I closed my eyes, awaiting that first painful swat with the seriously hard piece of wood. Eventually, after a few moments, I answered, although this was muffled due to being held down into the table by Jane and Pauline.

“Yes, Auntie Louise. Please don’t paddle me!” I pleaded.

She laughed as she looked across at Miss Manson and Mrs. Wardell. Next, she looked at Rachel Lindley and then finally at Wendy, who smiled sympathetically.

“Fat chance, you filthy little beast!” Miss Walton snapped.

Seconds later, her first swat landed across the already sore and warm centre of my bottom.

“Whack!”

My screams were muffled by Jane and Pauline pushing me down into the table. The pain burned across my bottom, but there was no time to dwell on it, as behind me, Louise took aim once more and delivered her next painful smack.

“Whack!”

Once again, I wriggled and squirmed as the pain registered in my brain, but it was no good. I was going nowhere thanks to the combined efforts of Auntie Pauline and Auntie Jane, who used all of their strength to hold me relatively securely in place over the table, allowing my ex-Maths Mistress to administer her part of my punishment without interruption. This was a task that Louise Walton relished, and she laid each swat across the fleshy centre of my bottom with gusto.

“Whack!” “Whack!” “Whack!” “Whack!” “Whack!” “Whack!”

“Whack!” “Whack!” “Whack!” “Whack!”

After her first dozen painful swats, Miss Walton paused and leaned in close to inspect her work. The thirty-six-year-old was powerfully built and each smack with her paddle had been extremely painful, causing my already red and bruised bottom to become an even deeper shade of red. Louise smiled as she listened to me sniffing and crying into the table, but it received no sympathy from her.

“I’m going to teach you a lesson that you won’t be forgetting in a hurry, you filthy little pervert,” she scolded in her best teacherly tone.

A few moments later, Louise Walton was back in position at my left-hand side and she began tapping the heavy piece of wood against my bottom once again. Within four minutes, she had administered her second, and final, set of twelve swats with her paddle, not saying a word as she did so.

“Whack!” “Whack!” “Whack!” “Whack!” “Whack!” “Whack!”

“Whack!” “Whack!” “Whack!” “Whack!” “Whack!” “Whack!”

Auntie Jane and Auntie Pauline continued to hold me down into the table until I calmed myself. I was crying, sniffing and sobbing uncontrollably from the paddling and they waited until my breathing had returned to almost normal before releasing some of the weight they were pressing down on my shoulders. Miss Walton calmly walked past where I was lying face down and replaced her paddle on the table before walking back to the living room and picking up her glass of wine, from which she took a mouthful. The young lady with the short dark brown curly hair was warm and used her left hand to unbutton three of the buttons on her short-sleeved white blouse.

Mrs. Taylor allowed me a few minutes to regather my composure before she introduced the next part of my punishment. It was Aunt Rachel. I had been both excited and anxious about a punishment from Miss Lindley. Excited as I wanted to find out what a walloping with her nasty canvas plimsoll felt like and also anxious, as I had heard the tales, and seen my friend Nicola’s bottom after she had been made to bend over Miss Lindley’s desk in the PE Office and receive a dozen, nasty, full-force smacks with the lesbian PE Mistress’ black, size eleven, rubber-soled shoe.

Rachel Lindley smiled at Wendy, then at Pauline and Jane, who were still holding onto me. The young PE Mistress walked past me and picked up her large, black canvas plimsoll. She looked down at the back of my shaven head as she returned to her position, tapping the heavy shoe against the palm of her right hand. She said nothing as she thought about how she was going to administer the whacking with her gym shoe, eventually placing her left hand on my lower back and pushing down, which raised my bottom slightly. As she did this, she began tapping the size eleven plimsoll across the lower part of my sore bottom.

Miss Lindley smiled at Auntie Jane and Auntie Pauline and they took hold of my arms once more, pushing down with their free hands on my back. Rachel Lindley licked her lips and adjusted her stance, placing her left foot slightly in front of her right. The young PE Mistress stopped tapping the gym shoe against my sore bottom and held it against my warm backside.

“So, Auntie Rachel. Are you going to give this naughty young man the taste of a real walloping with your plimsoll, just like you give your naughty young ladies in your classes?” Auntie Wendy stood watching her, hands on her hips.

Miss Lindley pushed down harder with her left hand on my lower back.

“I’m not really sure about this, to be honest, Wendy. I mean, I give my naughty girls twelve smacks with my plimsoll if they really have misbehaved for me or not done as they have been told. I can’t believe that he’s asked for this?” she replied quietly.

It was Louise Walton, standing in the living room and watching from behind, who helped her colleague out.

“Just imagine that he’s Nicola in your Form class and slipper that arse hard, Rachel!” she answered sternly.

Mrs. Taylor moved up to Rachel Lindley’s left-hand side and smiled at the younger woman.

“Give his bottom a dozen smacks, dear, like you would one of your girls. He did ask for this especially, so it would be a little disappointing for him not to receive a walloping with your gym shoe, Rachel,” Wendy spoke quietly to reassure the PE Mistress.

“Okay. I’ll just imagine that it’s Nicola then and give her a dozen,” she replied as she turned her attention back to my bare bottom, which was sticking out in front of her, awaiting her attention.

She tapped the gym shoe across the lower part of my bottom before drawing it back in her right hand.

“Now, Nicola. You have left me no option but to wallop your bottom for your behaviour today, so you’ll be receiving twelve smacks with my plimsoll and these will be given hard – and I mean, very hard so that you learn your lesson today. No fuss, or I’ll start over. Just lie there and take them, girl!” The muscular PE Mistress with the short brown hair took a deep breath before bringing her plimsoll down hard against my lower right buttock a moment later.

“Thump!”

The sound echoed around Wendy’s large dining room and I squirmed and wriggled as the shoe burned into my already sore bottom. However, my attempts to move and stand up were futile as Auntie Pauline and Auntie Jane pushed me down into the table. Miss Lindley allowed me a while to calm down before she raised the plimsoll once more, this time landing her next smack across my left bum cheek.

“Thump!”

Again, I struggled and squirmed about as much as was physically possible with Pauline and Jane using their weight to keep me in position over the dining room table. The thirty-four-year-old PE Mistress began to relax, and as she paused to allow me to settle once more, she adjusted the sleeves on her long-sleeved jade green blouse. She smiled across at Wendy, who was watching in awe at how hard the young woman could land her gym shoe across my bottom and at the sound each full-force whack with it made as it kissed my bottom.

“Thump!” “Thump!” “Thump!” “Thump!” “Thump!”

“Thump!” “Thump!” “Thump!” “Thump!” “Thump!”

Once she had administered her dozen, painful smacks with the large gym shoe, Miss Lindley placed it down on the table and began looking at my bare bottom, which by this time, was a mixture of shades of dark red and it was swollen in places, thanks to Rachel’s walloping. As Pauline and Jane held me as I sniffed and sobbed, the PE Mistress ran her right hand over every part of my sore and burning bottom and thighs. As Mrs. Taylor walked over and picked up her thick leather belt, Rachel Lindley pushed her hands between my legs and began touching and stroking my cock.

The other ladies noticed this and smiled at the young woman, who continued touching me as Mrs. Taylor began to take up her position to my left-hand side. She wrapped her thick leather belt around her right hand and smiled as she waited for Rachel to finish with me.

“Is that how you 'soothe' your girls after they have been spanked, Auntie Rachel?” Miss Manson asked before breaking out in a fit of laughter.

Miss Lindley moved back and smiled with embarrassment. She joined Louise Walton just inside the living room and picked up her glass of wine as she prepared to watch Auntie Wendy in action.

“I have touched some of the girls afterwards – those who are generally nice girls who have just experienced my plimsoll for the first and probably the only time,” Rachel answered quietly.

“I’d like to soothe him afterwards, if I’m allowed, Wendy,” she added.

Mrs. Taylor nodded at the younger woman as she kicked off her black high-heeled shoes and took up her position at my left-hand side. She carefully adjusted the belt in her right hand, ensuring that the metal buckle was flat in her palm, and wrapped it several times around her hand to shorten its length, making it easier for her to control and also safer for me as she wouldn’t wrap it around my thighs by accident. Auntie Wendy smiled as she listened to my sniffs and sobs continuing, despite Auntie Pauline trying to soothe me.

“Right, young man. It’s my turn to tan your backside for your bad behaviour,” Wendy Taylor spoke softly as she laid the thick black leather belt across my already sore bottom.

“I’m spanking you because you got excited while you were over Auntie Jane and Auntie Pauline’s laps and made a mess on their lovely skirts,” she continued.

“You will take twelve swipes with my belt and you will take them with very little fuss, my boy because if you don’t, I’ll start all over again,” she scolded.

I felt Jane and Pauline tightening the grip they had on my arms before they began to push down on my shoulders, forcing my bottom to rise. Once they were satisfied that I couldn’t move, they both nodded across at Wendy, who took her belt back over her right shoulder. She paused for a few moments before taking a deep breath. Once she was happy where the belt would land, she brought the belt hurtling through the air, its journey broken a moment later when it connected at full-force across the centre of my swollen bottom. The sound it made echoed around the dining room.

“Whap!”

The pain burned across my backside, but there was no real time for the pain to register in my brain. Mrs. Taylor immediately returned the thick, black leather belt to her shoulder, only waiting to check that Jane and Pauline had a secure hold on me. Once she was happy, the belt was sent on its way once again.

“Whap!”

My screams, cries and promises to be good from now on were muffled by being pushed down into the dining table and over the next ten minutes or so, Wendy Taylor administered a dozen full-force and unfeeling swipes with her heavy belt. My bottom felt like it was on fire and, no matter how much I cried and tried to move, it was no good. Auntie Wendy simply ignored the noise and concentrated upon landing her dozen, nasty slaps.

Whap!” “Whap!” “Whap!” “Whap!” “Whap!”

Whap!” “Whap!” “Whap!” “Whap!” “Whap!”

Once the final smack with the belt had landed, Auntie Wendy walked to where Jane and Pauline were holding onto me tightly and placed the belt down on the dining table. The two female teachers continued to hold me down, pushing down on my shoulders with all their weight, as Mrs. Taylor walked back to my left-hand side and she smiled as she inspected my well-punished bottom. Over the next few minutes, and ignoring my sniffs and sobs, Wendy touched my burning buttocks and backs of my legs with her right hand, running her fingernails over every inch, careful not to apply too much pressure to my delicate bum cheeks.

The French Mistress looked across at Pauline and Jane, who slowly began to relax the hold they had on me before she turned and looked over her shoulder at Rachel and Louise, who were stood behind her with their wine glasses in their hands.

“I think that’s a wonderful team effort, ladies, and that is one well-punished bottom.” Mrs. Taylor carefully pulled her azure blue, long-sleeved blouse from her charcoal black knee-length skirt.

“However, this young man needs to truly have the message driven home to him that we won’t tolerate bad behaviour or that we won’t put up with him being a little pervert who thinks about being spanked and perving over us!” she laughed.

“So, I think that we had better adjourn to my bedroom, where we shall each give him six of the best with my canes,” she purred and licked her lips.