The Sissy Suck Chair
It was one o'clock on Friday, and Jeremy Sweeting reported as usual to the Headmistress's study. His heartbeats raced while his groin ached with anticipation. What would she dress him in today? Would she have that lovely green and white gingham dress again which she had put him in two weeks ago? And those silky white panties that went with it? He had dreamt of that wonderful afternoon every night since... far more than the white pleated skirt she had him in last week, with a girls' mackintosh worn over it. He had felt lovely, but...
The door opened and the large figure of Mrs Breastwell, swathed in a shiny green dress, loomed above him.
"Come inside boy," she said, and Jeremy scrambled to his feet and followed. Funny how in all his years at Sandford High, he had never been inside her office until a month ago. Since the time she challenged him to put on a girls' dress to see if he reacted in the right way.
Apparently he had, for she was not furious with him, nor disgusted. She had simply ordered him to return each Friday for the continuation of 'his lessons'. And now his penis was rising uncontrollably as the same perfumed smell assaulted his nostrils. As the door closed behind him with a turn of the key, the furniture, window and walls passed into insignificance: all he could see was today's dress: a shiny girls' frock in pale blue silk on a stand in front of him, and on the floor beneath was a pair of pale blue high heeled shoes.
"Turn round, Jeremy. You must be got ready for your lesson."
He was within six months of leaving High School, but he stood and allowed himself to be undressed, as if he was a toddler.
"You will have noticed that you will be wearing girls' shoes today, Jeremy. And that means I will be putting you into a pair of nylon stockings."
He stiffened and blushed at the same time as she unhooked his briefs from his upright penis.
"Today, you are going to learn what it is to be a sissy girl and I have an assistant who will help me."
Oh my goodness. How degraded he will feel if another woman sees him when he is being put into that shockingly pretty dress with petticoats and panties. He just knew he would give himself away by erecting in his panties. There was pretty organza at the yoke and neck ruff. It was so obviously a dress for a little girl... and he was going to wear it himself and delicious little-girl feelings would overwhelm him. He felt such a glow in his whole groin. What was becoming of him? His legs felt so bare and vulnerable, even though they were now dressed, or sort of dressed, in sheer nylon stockings which pulled at the garters from the belt round his waist. Mrs Breastwell slid the dress upwards off its stand, revealing white petticoats beneath, and laid it across her desk. The petticoats sizzled girlishly as she lifted them into the air, then presented them for him to put his head through.
Jeremy's knees weakened close to collapsing as the familiar feminine sweetness flooded through him. The petticoat silk hung from ribbons across his shoulders and floated prettily round his waist and hips, caressing his rigid erection. He knew he was being a good boy for her. She gathered up the dress and opened it out.
"Turn round, Jeremy. I am going to put you into your dress for the afternoon. It will soon become your first little-girl sissy dress."
What did she mean, 'his little-girl sissy dress'? He may attend dressing lessons with the Headmistress, but he had no intention of being a sissy, let alone a 'little girl'. But ohhhhhhh, the fabulous sweetness of having a little-girl's dress on, the sweet little buttons fastened down from his throat to his waist and over his very stiff penis. He caught a glimpse of Mrs Breastwell's crimson lips, pursed in authority and concentrating on fussing and tucking his dress so that it hung correctly over his petticoats.
"Come with me," she said, and took his hand to lead him into the Chair Room where she taught him his feminine lessons in his girls' clothes. But this time the usual chairs for himself and Mrs Breastwell weren't there. Instead there was a single chair... a funny chair... pink, with straps. She made him turn round and sit in it, and fed each of his hands into the straps alongside his shoulders. Next she spread one of his legs wide and strapped it at his knee, then at the ankle. He was fastened the same way on the other side, so that he sat opened out, feeling as though he was presented for her to examine his penis, as she often did. Then she pulled each strap in turn from behind the chair, tightening him in.
"I'll be back in a minute boy," she said, leaving him alone in his sweetened state, loving his private lesson with Mrs Breastwell more than ever but dreading that this 'other woman' might spill the news of his girly dressing. No-one else must find out what he did on Friday afternoons.
He heard her returning, talking to someone, then the door opened with a swishy sound of silk. He saw her companion with a burst of fright and his penis seemed to jerk with horror. It wasn't another woman: she had returned with a sissy boy in a fearfully young and girlish pink dress and... oh my gosh!... it was Clive Pettinix from Leavers class 2.
The boy looked so pretty... terrifyingly like a girl, with lipstick shaping his lips, and his large eyes lined perfectly with make-up. He showed an uncomfortable interest in Jeremy, standing in front of him, his glossy lips almost smiling as he looked down at his defenceless erect penis in the middle of his chair. Those lips and those eyes made Jeremy's penis stiffen uncontrollably. Mrs Breastwell fussed Clive's pink dress for him from behind, speaking into his ear.
"Clive, remember yesterday at my house, how you learnt to suck my sissy son's clittie?"
"Yes, Mrs Breastwell." he answered in a soft girlish voice.
"Well now you are going to suck Jeremy for me."
Jeremy nearly fainted. His hands and feet stretched instinctively in their straps and a wail escaped his lungs.
"No - I don't want her to suck me!"
Ohhhh, why had he said 'her'? It was because Clive Pettinix looked more like a girl than a boy in his lovely dress, and now he sank to his knees in a waft of wide white petticoats, his face barely inches from Jeremy's stretching penis. Ohhh, it was horrifying and... and yet it was arousing him so unbelievably.
"Noooooooooo!" cried the panicking occupant of the chair, and his legs tried to close while his hands reached to intercept the sissy's face. "I don't want it! Please stop him. I..."
The Headmistress was behind him, and reached over him to insert a ball into his mouth as he spluttered, pulling it round his cheeks and fastening it together at the back of his neck.
"Now Clive," she said calmly, ignoring the panic between them, "what is the most important thing to remember about sucking a sissy's cock?"
The boy on his knees looked up at her. looming above Jeremy Sweeting's head, his face bright with information. "To suck him like a girl." he said proudly.
"That's right. Tell me and Jeremy, how do you feel like a girl?" "I spread out my lovely dress and feel girlish in my panties." His hands pulled his dress out at the sides, holding a pinch of petticoat frills too which made him look so pretty. "Good girl. Jeremy is going to become a lot more girlish, like you, in the sissy suck chair."
The chair-bound boy wriggled and "Hmmmmphed" in resistance, but was unable to move his bottom in the slightest, with the result that his stiff penis was a sitting target.
"Can I start sucking him, Miss Breastwell?" said Clive enthusiastically.
"Yes, my dear. Remember, soft, feminine touches with your lips. Hold Jeremy's little clittie in one hand while you hold out your dress and petticoat with the other. That's right."
Jeremy went white as Clive's soft, red lips dabbed little kisses on the tip of his helmet, parting his lips ever so slightly so that his kisses became more open, and moist, with soft kissing sounds.
"Goo-o-o-ood Clive dear. Now you should start to lick a little bit lower down his girly clittie... softly, reaching down and pulling up. Wet your lips, pet. Oh, that's good licking, darling. Now close your wet lips around Jeremy's clittie. Push a bit lower, keeping hold with your lips. Now, suck ever so gently...just as a girl would, licking him inside your mouth. Slide your pretty lips up and down ever such a little bit... up and down, up and down. Mmmmmmm, isn't that lovely, Clive darling. Now...rising then sinking, with your lips clasped round your sissy friend. Spread your lipstick up and down his lovely clittie. Good girl, that's beautiful cock sucking, Clive darling."
The sissy unclasped his lips for a moment, just long enough to say: "Oh Mrs Breastwell, Sissy Jeremy has such a pretty, girly clittie!" He resumed his sucking and tonguing, as his sweetheart's struggles became more of a girlish wriggle as waves of pleasure flooded through him.
"Yes, darling, he's becoming a lot more sissy, isn't he?... or should I say 'she'?" There was a choking little cough in Clive's throat, and he sucked and sucked while humming with pleasure, and the Headmistress saw dribbles of sissy cum seeping from the sides of his mouth and dribbling down his chin. Clive hung on and kept up his licking and sucking to bring out spurt after spurt of Jeremy's creamy cum.
"Well done, darling. You've made him lovely and sissy. Now this time, we're going to suck far more deeply, to make Jeremy feel even more girlish in his lovely stiff clittie. Later we'll go to my house and Jeremy can meet my son and I'll put you all in babydolls for sissy, bedroom fun."