I was 23 at the time. There were 4 of us young boys in the class. We all signed up for it and I paid my tuition fees. It practically wiped out my savings account. It was a course I found online, in the next state over from me, but room and board were included, and I just failed out of college and lost my dorm. It said all clothes, class materials and textbooks will be provided. I was failing miserably at life and wanted this new start. I couldn’t deny it or lie to myself any longer. It was a sissy school. I also felt that maybe I was gay, but never wanted to act on it. The school offered a different approach than being gay. I had often played with my sister’s clothes at home anyway, so I liked the idea. As a sissy I felt I would be able to express my repressed feelings in a different way, with real men, not gay men. I needed this course. It could take up to 2 years to complete it. The website said those who apply themselves could finish in 18 months.
Our Headmaster and owner of the school was Mr. Winston, and we were told to address him as Headmaster Winston, Mr. Winston, or Sir.
Before we entered our classroom for our first day of orientation and class, we were given little schoolgirl outfits to wear. White, short sleeve tops, with little, short neckties, short pleated, red and black plaid skirts that flared out, white cotton panties, and black and white saddle shoes with white ankle socks.
We took our seats at our assigned desks, somewhat uncomfortably, looking around at each other. The room was very clean, but there was an air of stale cum lingering about in the room. Headmaster Winston introduced himself and then began with our orientation. He never even said a word about our schoolgirl outfits. I guess it was part of the program and he had probably seen many of us dressed like this in his classroom before. I wondered how many sissies he’s had in this classroom before us.
“You’re all here because you finally want to admit to and affirm your true identities. You’ve registered for our sissy school because you’ve always felt out of place, bullied in school, rejected by women, small penises, been wearing female clothes, looking at sissy porn. Your 4 personal instructors and tutors are all ladyboy’s or shemales. That’s not why you are here. You are here to become sissies. Sissies are different and serve a different purpose. Ladyboy’s and shemales like to be pleasured and have their cocks sucked. They also like to fuck. Something you will never do. You’ll receive no such pleasure. Your pleasure as a sissy comes from pleasuring your men, sucking their cocks, and making your asses available to them, whenever they want. You’ll be trained by your tutors by sucking their cocks. If a tutor is naked, you will not touch their tits, since a woman’s tits will never be an option available to you in your new life. Your classmates are your sisters and should be addressed as Sister.”
He asked, “How many of you have a sucked a cock?”
Two boys raised their hands. I did not.
“How many of you have taken a cock anally?”
One hand raised. Not mine.
“Later today you’ll be taken and given showers and have all your body hair removed from your eyebrows down. After today, you will only wear panties, nylons with a garter belt, and a bra during class. You’ll wear dresses in the dining room. Slips are worn with dresses. Thong day is every Friday. You’ll be fitted with the appropriate sizes by your instructors. Four pairs of nylons in four different colors will be issued to each of you. One black, one nude, one suntan and one charcoal. You may select your own color to wear each day for class. Never attend a class with runs in your stockings. If you need more hosiery, they can be purchased at the Commissary. You’ll also be issued 4 matching bra and panty sets. Your feet will be measured for high heels, and it will be difficult at first, but you’ll be expected to wear them at all times. You will sleep in nighties, teddies and nightgowns, always with panties and a plug inserted in your bottoms. You’ll be given estrogen and progesterone at bedtime to increase your female hormones. Most sissies see some breast growth from taking the hormone pills. Make-up and hair will be done by our cosmetologists, and they will teach you to do you own. They will also do your fingernails and toenails until you learn. Pink is this week’s color. There is a color changing chart in your rooms. You will change your polish every two weeks.”
I was feeling nervous but yet a tingling sensation ran through my body.
“After your graduation, we offer placements for some of you in good standing, who have met our rigid requirements, with several of our most discreet clients. Sometimes some of our new sissies are hired on as private secretaries, or household maids. You can also find work in the sex industry making porn films or performing in gay strip clubs or with drag revues. We hire mostly ladyboys and shemales here as tutors, but we have hired a few sissies here as examples to the new girls. Sissies bursa merkez escort can also work as waitresses here, in the laundry room and as housekeepers. Most of you will live here at the dorms and will be “on call” for private functions, or personal calls as escorts and dates for wealthy, discreet male clients. Generally, our clients are all married straight men. They want a sissy twink on the side to do for them what their wives won’t do. That’s where you come in.”
It was a bit overwhelming, but pleasing a man; I thought to myself, this is what I wanted.
Mr. Winston continued, “I’m sure all of you have heard of cock cages or chastity devices. Our school does not teach that although you will be given one week’s training wearing a cage. We find most of our clients like to either see the sissy flaccid or erect to show how much they are enjoying pleasuring the man. They often like to see your little dollies flopping when they fuck you. We also train you for light bondage and spanking sessions. We don’t allow any of our sissies to be subjected to any hard-core bondage.”
I looked at the textbook in front of me. It was written by Dr. Elizabth Holton, apparently a well-known Phycologist and Sex Orientation Therapist. “The Complete Guide for Sissies.” I thumbed through it and there were very intimidating, yet exciting chapters that were titled, “Cock Worship,” “Anal Acceptance,” “How to Give a Blowjob,” “Rimming,” “Swallowing,” “Handies,” “Walking in Heels,” “Maid Training,” “Washing your Dainties,” “BDSM” “Sitting in Daddy’s Lap,” “Car Sex,” “Dressing for your Man,” “Toy Play,” among others.
Our headmaster told us, “You all have your textbooks. Bring them to class every day. There are illustrations and quizzes in them that you will helpful, and you can take notes in them too. Any questions so far?”
We all looked around at each other, probably all had questions, but no one raised their hand.
Mr. Winston said, “Ok, then. Let’s get started today. I start off each morning with a blowjob from one of my student sissies. Let’s see…let’s have Sister Jilly come forward.”
That was me. We were all given name tags when we arrived. Mine was Jilly. Joanna was next to me. Katie next to her and Kimberly was on the end. Joanna was a short, red-headed boy about my height. Katie and Kimberly were both taller, but maybe by only an inch or two. Everyone looked a bit effeminate, including me, facial features and body types. It’s probably why we all signed up for this course.
I went to front of the class with all the other students and tutors watching. I was nervous and embarrassed, but I didn’t want to fail my first test.
Mr. Winston brought out his chair from around the back of his desk and placed it where everyone could see it. He sat down and said, “Jilly, get undressed.”
I wasn’t expecting him to say that but, I wanted to show that I wanted to be here and didn’t want to disrespect the headmaster. I took off my little schoolgirl outfit, getting undressed quickly, taking everything off, laying my clothes on his desk, and stood before Headmaster Winston naked, with an erection.
“Jilly, it looks like your excited to suck my cock.”
“Sir, yes Sir. I am, Sir.”
“Small, like most sissies. Very little pubic hair. You haven’t grown into much of a man have you, Jilly?”
“No, Sir. Not at all, Sir. I believe that’s why I’m here, Headmaster Winston.”
“No worries. You won’t have any use for your little dolly anymore anyway and your pubic hair will all be shaved off.”
“Yes, Sir, I understand, Sir. Thank you.” I responded.
After ridiculing me, he pinched the skin on the bottom of my ball sack between his thumb and index finger and pulled down sharply and forcefully on my ball sack. It caught me off-guard. It made me wince and stand up on my tiptoes. I squealed, “Ahhhh!”
He laughed and said, “Up, up on those toes, sissy!”
I tiptoed from side to side in front of him while he pulled on me harder. My classmate “Sisters” giggled. He lectured the class while he held me in suspense by my balls. “These little appendages between your legs are never to be referred to as a cock! Real men have cocks! You sissies have little dollies. Understood?”
“Yes, yes, my little dolly…please, Sir, please!” I was begging him to release my ball sack.
Finally, he released me and said, “Kneel down in front of me, little, naked, humiliated, sissy Jilly, and unbuckle my pants. Use one hand to pull upwards at the top of my pants and pull my zipper down with your other hand. Open the fastener at the top of my pants.”
I got his pants opened. He asked the others, “Girls are you all watching?”
They responded in unison, “Yes, Mr. Winston.”
“Now you ask me politely to stand up so you can lower my pants and underpants.”
“Headmaster Winston, will you please stand up for me so I can lower your pants and underpants for you?”
Mr. Winston stood up and I lowered his trousers and boxers. bursa escort bayan He had a huge erection, probably 7″ or more and a very hairy bush surrounding his cock and balls! He was definitely all man! He sat back down.
He said, “Now put your hand around the back of my shaft and bring it slightly towards you. Take a good smell of my cock. Kiss my head. Lick the underside of my shaft from my cockhead down to my balls. Up and down my shaft, Jilly!”
I moaned as I licked his masterful cock, something I’ve never done before. I was as hard as could be.
“Good, Jilly. Now my balls. Lick them.”
I licked Mr. Winston’s big hairy balls.
“Suck on my balls Jilly! Don’t be shy. I want my balls feeling really good.”
I mouthed his balls as I wrapped my hand around his thick cock shaft.
“Good Jilly. Now pull my cock down towards your mouth. Open your mouth and lock your lips around my cockhead. Stroke my shaft up and down while you hold me in your mouth.”
The other girls and instructors were all watching me suck our headmaster’s cock. At first, I felt ashamed of my behavior, but I realized this is what I signed up for. As Mr. Winston instructed me, I felt more relaxed and wanted to do this for him. I had to open my mouth wide to accept his huge bulbous head.
“That’s it. That’s it. That’s what I want my sissies to do for me.”
I mumbled, “Yes, sir.”
“Ah, that’s better. Flick your tongue on my cockhead. Are you beginning to understand your role as a sissy, Jilly?”
I held his cock and answered him, before putting him back in my mouth. “Yes, Mr. Winston. I hope it feels good for you.”
“Very nice. Soft lips and hands just like a girl. Deeper now. Deeper in your mouth, Jilly. Suck my cock, sissy.”
I took him deeper. I knew I could never take him all, at least not this soon in my training. He hit the back of my throat a few times. I gagged a little.
“Gagging is normal at this point in your training, Jilly.”
I garbled back, “Yes, Sir.”
“That’s it, Jilly. Lick the underside of my cock with your tongue.”
I felt Mr. Winston’s cock swelling and thought he was going to cum.
He said, “Jilly, I’m going to cum. Stroke my cock and hold it out, pointed at your open mouth.”
Mr. Winston barely let out a little grunt. He was apparently very used to getting these blowjobs. I was just the next one to give him his. He liked to humiliate his sissies by having me hold my mouth open for him, while I stroked him, aiming for my wide-open mouth. His cum shot out into my open mouth, about 6 spurts, as his receptacle for his sperm.
He said, “Good girl, Jilly. Swallow it and lick my cock clean.”
I did as he told me to do. He stood up and told me, “Get under and lick my ball sack, then pull up my pants and zip me back up.”
I got underneath Mr. Winston and licked his big hairy balls again and sucked each one gently between my lips. After I zipped him up, I thought I should be polite and said, “Thank you, Mr. Winston.”
“You’re welcome, Jilly. Was that your first time giving a blowjob?”
“Yes, sir, it was.”
“I’m sure you enjoyed it?”
“Yes, sir, I did, very much so.”
“Good. You’ll do well here. Lick my cum off your lips. Get dressed and take your seat.”
“Yes, Sir.”
Even though I still had a hard-on, Mr. Winston made me get dressed, tucking my erection back into my little, soft, cotton panties and putting my schoolgirl outfit back on and taking my seat. I knew what I did was for his pleasure, not mine, even though I was so hard the whole time. It made me feel proud to do it for him and be the first one in our class to take his member in my mouth, even ejaculating in my mouth and swallowing his load.
He spoke to the class and said, “As you all can see, Jilly enjoyed it and you all will too. That was a very good effort for your first time, Jilly. After some practice with your tutors, I’ll have you taking me more deeply until you can deep throat me. You won’t be able to graduate until you can engulf me fully, down to my base. Sissies are expected to do that. You’ll all have the opportunity to blow me while I’m sitting down, standing and laying down. Always give me your best effort. Your grades will be recorded and go towards your final exam and class rating. You’ll all have plenty of practice sucking your tutors’ cocks. You’re required to suck them anytime they tell you to, even while we’re all in class together. It’s for your own benefit. Your male clients may want it anytime too. In the car, their office, in the shower, in the men’s room. You must show them you want it too and that you’re always eager to please them. Later on, in your class studies, you’ll learn more about deep-throating and swallowing cum.”
When I got back to my seat, I looked down at Joanna’s crotch and the front of her skirt was soaked! I thought she had an orgasm just from watching me suck Mr. Winston. One of the tutors spoke up, “Mr. Winston, Joanna was masturbating under her bursa ucuz escort skirt while watching Jilly suck you off.”
“Is that true, Joanna? Stand up!”
He could easily see how wet her skirt was.
“Come up here, Joanna.” She went to the front of the room trying to cover her front with her hands.
“Joanna, lift your skirt!”
She pulled up her skirt to show him her wet panties.
He scolded her, “Joanna, you don’t ever masturbate without permission, and especially during class time during a demonstration. Bend over my desk.”
Joanna sheepishly bent over Mr. Winston’s desk. He lifted her skirt laying it over her back. Then he pulled her panties down around her ankles. “Spread your legs. Your Sisters will now come up and each will apply 10 smacks to your bare bottom, Joanna.”
We could see her balls dangling between her legs. By the time Kimberly had finished swatting Joanna’s bottom, we could see Joanna was hard, but already crying. Katie went next. Her bottom was red by the time it was my turn. I felt sorry for her and tried to go easy on her. We all returned to our seats. Joanna pulled up her wet panties and returned with us. Nothing more was said about Joanna. Nothing needed to be said. We got the message and so did she.
Mr. Winston told us, “I believe your instructors have one more task for you today before your showers.”
The four shemales came forward and sat in chairs in front of us. One of the girl’s, whose name was Tina, told us, “We want all of you to undress now and kneel in front of us. Show us how much you like and want cock by masturbating while looking at ours.”
The girls took off their skirts. Tina, a shemale and Jasmine, one of the Asian ladyboys, were wearing nylons and garter belts and no panties. The other two, Jade, the other Asian ladyboy, and Sabina, the other shemale, were bare from the waist down. All four were hairless, except for Tina who had a little patch above her huge cock, not as big as Mr. Winston, but a healthy 6 or 6 1/2 incher. All had hard-ons, the two Asian ladyboys, Jade and Jasmine, having the smaller cocks but looking simply amazing. What a beautiful sight for four sissies to look at!
We all stripped down. Tina told us, “Everything. Shoes and socks too.”
Small bowls were placed on the floor in front of each of us. Tina told us, “All of you sissies lick your lips while you look at us. Your training begins now. Cross hands and jack-off the sissy next to you. You’ll all get your first chance to suck us tonight before bed.”
We were all on our knees, naked and erect, looking at the “girls,” and what hung between their legs. It was our first time all being naked together, but I was sure it wouldn’t be our last. We were also all probably under 5″. I knew I was only about 4 1/2. I reached over for Joanna’s dolly with my right hand, and she felt about the same size as me. She apparently already had taken to shaving and her dolly felt smooth in my hand. Even though I had never done this before with anyone, touching her dolly felt natural to me and I was enjoying it. Kimberly was the biggest and Katie was the smallest. We were given no lubrication to use and were “dry-jacking” our fellow classmates, our “Sisters.”
Mr. Watson informed us while we were masturbating each other that masturbation is not permitted at the school with the exception of tonight with our “Sisters.” He told us, “The only way you’ll be able to orgasm is when you’re being fucked, so if you want to avoid blue balls, get used to your ass being penetrated and learn to enjoy it quickly, so you can cum. I’ll be taking each of you sissy girls a few times myself over the course of your schooling with us here. For your sake, you should hope my member up your behind will bring you off. Your instructors will be doing the same for you. Work with your tutors. They are here to help you. If they are naked, concentrate on their cocks and not their bodies. Keep yourselves clean. Take an enema every other day. And never touch your dolly without permission.”
Tina was right in front of me. She was the big shemale, almost Amazonian-like, with the big cock and towered over me at nearly 6′ tall against my small 5’6 frame. Raven black hair and black public hair on her little patch above her cock. It looked like she had big breasts under her top. She was strikingly desirable! Especially her cock. I hoped she would be my trainer. Her cock looked amazing, and I was already lusting over her. All of my “Sisters” eyes moved back and forth over the pretty ladies’ cocks.
Joanna also seemed to enjoy masturbating me. Kimberly and I, both on opposite ends, came at nearly the same time into our bowls. It took me a little longer to bring Joanna off and Katie was the last to cum, but only a few seconds behind the rest of us. They gave us wet wipes and instructed us to wipe each other’s cocks. Afterwards we returned to our desks while still naked. The tutors picked up the bowls, switching them around on our desks and Tina said, “Lunch is served, sissies!” They all laughed at our indignation. It was just all part of sissy school, and I was learning quickly.
We were made to lick the bowls clean. Tina told us, “Tomorrow’s breakfast will be oatmeal. One of us will have each made a deposit into each of your bowls. Eat hearty, sissies!”