Sissy College Ch. 03

Standard disclaimers apply. I'm indebted to Puzziboi for writing the first half of this chapter: Thank you! I really do enjoy your feedback, so please keep it cumming! Lastly, I encourage you to read the previous chapters before you delve into this one.

Mr. Blackwood slapped his large veiny cock against Lenni's smooth lily white face with an audible smack. The former standout athlete studied the soon-to-be sissy carefully as he stuffed his giant member back into his silk boxers. The Black Adonis pulled up his pants to Lenni's dismay.

"Why the long face, Lenni?" Mr. Blackwood inquired.

"I just thought..."

"You thought I was going to let you suck this big black cock, didn't you?"

"Well...well...yes sir," Lenni confessed.

"Trust me, I want to. Very badly. But you are not ready. Take this to Miss Arabella's office," the principal said handing Lenni a slip of folded pink paper.

Lenni accepted the note in bewilderment.

"Now," the aroused educator commanded.

~~~~~

Lenni hustled out of Mr. Blackwood's office and down the hallowed halls of Chester College. He reached the domain of Miss Arabella who was the Headmistress of the Sissy Boi Program. She reported to directly to Mr. Blackwood and it was widely suspected, if not known, that she was his pet.

"Yes," lisped the receptionist, Sarah, who was a small waifish sissy boi.

"I have this note for Miss Arabella from Mr. Blackwood," Lenni remarked handing her the paper.

Sarah studied it and replied, trying very hard to stifle a giggle, "Have a seat, Lenni. Miss Arabella will be right with you."

A few minutes passed and the door to Miss Arabella's office opened.

"Have a good day, Sophie! You're progressing nicely."

"Thank you, ma'am," replied the tall, lanky blonde sissy boi wearing the standard issue pink booty shorts and white halter top.

Lenni admired the exiting head sissy that was doing quite well on her hormone replacement regimen.

"Who do we have here, Sarah," quizzed Miss Arabella.

"Lenni Taylor. Mr. Blackwood has requested a transfer from Men's to Sissy Boi," the smiling experienced faggot explained.

"Stand up," Miss Arabella said looking at Lenni. She sized him up and offered, "Come inside."

Lenni sat on the plush leather chair in front of the large mahogany desk. He studied Miss Arabella. She was a graduate of Chester - Class of 1999. Her father was Scottish of noble birth and her mother a Taiwanese immigrant. The short, pale skinned sissy had long flowing dark hair, wide-set eyes, a cute bubble ass, and perky pubescent tits. She dressed similarly to the sissies, but her booty shorts were lavender and her halter top was canary. She wore a white flower in her hair today along with a lavender rose pennant.

"A transfer," the head sissy in charge mused. "Are you ready?"

"Yes ma'am," Lenni stuttered.

"I'm sensing some apprehension," she protested.

"No ma'am. I'm ready."

"Ready for what?"

"I'm ready to become a sissy faggot."

"Do you wish to worship cock?" she pressed further. Images of Mr. Blackwood's fat fuck stick flashed through the faggot's mind.

"More than anything," Lenni exhaled.

"Very well," Miss Arabella relented. "You will be expected to progress quickly as we are already into the school year. Give me a moment," the attractive biracial sissy said as she stood from her desk.

She returned several minutes later with a medium height pale-skinned sissy. Lenni admired the beautiful form of her slender and subtly curvaceous body. She was a 'Daffodil' which meant she was in the highest rank of not-yet-graduated sissies.

"Lenni, this is Cricket. She will be your mentor. Listen to her carefully and use her as your guide," Miss Arabella warned him.

"Yes ma'am," Lenni beamed. "It's nice to meet you , Cricket."

"Likewise," the attractive ginger-haired fairy replied.

"There are a few rules I need to cover before I issue your new uniform," Miss Arabella began. "First, you must stay completely smooth at all times – even your pubic area. Body hair is to never be seen on a Chester Sissy. Secondly, you will wear the standard issue sissy boi uniform at all times while you are on Chester grounds – no exceptions. Until you are advanced from Blossom, which is where all our sissies start, to Daisy, you must wear this badge, identifying you as a Blossom. Finally, you will need to sign our Sissy Credo," she said handing him a contract.

Lenni read the paragraph.

AS A CHESTER COLLEGE SISSY, I WILL UPHOLD THE FINE NAME OF OUR BELOVED INSTITUTION AND BECOME THE PENULTIMATE EXPRESSION OF FEMININITY. I UNDERSTAND THAT I AM TO BE A COCK LOVING AMBASSADOR AT ALL TIMES. I HEREBY FORSAKE MY CLAIM TO MANHOOD AND PROMISE TO ESPOUSE FEMININITY IN ALL THAT I DO. I PLEDGE TO WORSHIP THE COCKS OF REAL MEN AND TREAT THEIR CUM AS A SACRED GIFT. IT IS MY SISSY DUTY TO HONOUR COCK IN ALL THAT I UNDERTAKE.

Lenni's clitty jumped in excitement as he signed on the dotted line.

"You are officially a Blossom – our lowest ranking sissy. The next level is Daisy which I expect you to achieve within the next 45 days. Cricket will teach you all that you need to know. After that, comes Orchid and then Daffodil. Upon graduation, you will reach the level of White Rose. If you are an excellent alumna, you can move up the ladder to Yellow Rose, then Red Rose, and ultimately Lavender Rose which you can see that I have achieved," Miss Arabella stated tapping her broach with her well-manicured forefinger. "There are only 17 of us at this level."

"Here is your uniform," the Headmistress said handing over the pink booty shorts and white halter top that matched Cricket's.

"Take him to the dispensary and give the nurse this," Miss Arabella instructed Cricket. "And ensure that this Blossom is ready for Dean Crawford's bedchamber within the fortnight."

"Welcome to the Sissy Boi Program," the sultry effeminate goddess beamed

Cricket and Lenni left the office quickly. Upon handing the orders to the school nurse, Lenni was given a pill bottle and two round tablets along with a cup of water.

"Take these two by mouth now. Then take two daily after breakfast," the elderly lady informed Lenni.

"What are they?" Lenni inquired.

"Testosterone blockers," Cricket replied. "All of us sissies at Chester take them. Hurry up. We have lots to talk about."

~~~~~

On the walk home, Lenni was torn. Despite being thrilled with the prospect of being a Chester Sissy, the idea of explaining what had happened today to his mother filled him with dread. How would he explain that he didn't want to be a real man? That he would rather suck dick than fuck pussy? That he wanted to be on his knees for big, strong black men?

These questions persisted in his mind all through his long walk home. When he reached home it was already 4 o clock which meant that his mother would be home in another 2 hours.

After the momentous events of the day (and being denied Mr. Blackwood's cock) Lenni was especially horny. He decided he would spend an hour delving into his black cock porn stash and then the remaining hour deciding how he would give the news to his mother.

Lenni opened the front door and quickly rushed to his room, eager to get his fill of dark meat. Now that he had had a taste of it, he knew there was no going back. He wanted a real cock filling his mouth but until he was ready, his porn stash would have to suffice.

Lenni was already panting with lust when he reached his room and to his utter shock, he found his mother at his computer!

"MOM! What are... ,"

His question was cut short when he saw what his mother was looking at: it was the porn! Black men fucking white women, black men masturbating, black men fucking shemales, black cock close-ups! It was all there, and his mother knew about it.

"Mom, I can explain!"

"Shhhhh," exhaled his mother, turning around and looking Lenni dead in the eye, "Explain what Lenni? That I raised a faggot? I always knew you were different, darling. Never the same as the other boys: a bit too feminine, a bit too weak but I had no idea you would turn out to be a cock loving faggot. I was out working two jobs, breaking my back to put food on the table for the two of us, while you were busy in your room, jerking off to other men!"

Lenni had never heard his mother talk like this, her voice dripping with anger.

"I got a call from Mr. Blackwood, telling me that they had approved a transfer for you to the Sissy Boi Program after your antics in the locker room. How disgusting! Touching yourself like that! At first I didn't believe him, but he suggested that I check out your PC and sure enough, it's full of black cock! Is this what you like? Big black dick? Is this what gets my sissy son off?"

Lenni gulped, as his mother returned to the computer screen, scrolling through more images for Lenni's benefit. Tears welled up in his eyes, the humiliation stinging deep. He tried to hold them back, but soon he was sobbing uncontrollably. His pale white cheeks filled with blood and his mouth contorted into a pout. He didn't know what to do.

"Shhhhh, baby. Don't cry." It was his mother. Her entire demeanor had changed: where she was bitter and condescending, her voice was now soothing and reassuring. She came over to Lenni and gave him a motherly hug. Lenni felt protected and safe, his sobbing beginning to die down.

"I'm sorry, darling. I shouldn't have taken it out on you like that. I was just so shocked about this whole thing. Why didn't you tell me you wanted to be part of the Sissy Boi Program? I've waited so long for you to come out of your shell. I was just so disappointed that I had to hear it from Mr. Blackwood first. If you want to blossom into a sultry little sissy, then you have my blessing sweetheart. Just no more secrets, okay?"

Lenni nodded his head in the affirmative, still locked in his mother's embrace.

"And truth be told," continued his mother, "I've always wanted a daughter around the house." She beamed, her smile so infectious that Lenni couldn't help but managed a giggle - the last of his sobs finally coming to an end.

"I also see you like them big and black, you little vixen," commented his mother, giving Lenni a knowing wink. The blood ran straight back to Lenni's face, this time from embarrassment. He gasped and brought his hands to his cheeks, trying his best to hide his blushes. She was beginning to enjoy this.

"How cute. You'll make a fine young sissy, sweety!"

"Mom, you're embarrassing me," managed Lenni. Despite his words, he too was beginning to enjoy this.

"Oh nonsense! If my son, wants to be a sissy boi, then I'll make sure you turn into the cutest, girliest sissy in the entire school," she said with pride. She paused for a moment, before looking at Lenni quizzically, "When you burst into your room, you were planning to get your little rocks off weren't you, baby?"

Her use of the word "little" did not escape Lenni's notice. He nodded, embarrassed at his own whorishness.

"Well don't let me stop you! Seems like you have quite the cock temple over here," exclaimed his mother, pointing to the screen. At the moment, there was a close up of a dark black cock peeking through a pair of blue jeans on the screen.

"How can you not want to suck that?" thought Lenni to himself. His mother, seemingly reading his mind, chuckled and walked out of the room.

"Have fun princess!" she called out from the doorway.

Lenni had never been more sexually frustrated than he was at this moment. The events of the day: Mr Blackwood's cock, Miss Arabella's office, meeting Cricket and the thought of wearing those cute pink booty shorts had all left Lenni hyper-aroused. He need to cum. Badly.

As soon as his mother was out of the room, a deliciously naughty idea came into Lenni's mind. He rushed to his backpack and whisked out the Sissy Credo that he signed earlier. He quickly stripped off his clothes before placing the contract on his desk and settling into this chair. He set up a quick slide show of all his favorite cocks on his computer. The slideshow began to play, cock after cock sliding across his screen.

With one eye on his screen and his hand furiously jerking his tiny clitty, Lenni began reading his Sissy Credo out loud,

"As a Chester College sissy, I promise to...."

Large virile cocks. Strong black men.

"I understand I am to be a cock loving ambassador...."

Delicious chocolate fuck meat. Big bloated balls.

"I hereby forsake my claim to manhood..."

Not a real man. Just a sissy faggot for black dick.

"...treat their cum as a sacred gift..."

Need to be around black men's cum. Thick, creamy and potent.

"It is my sissy duty to honor cock in all that I undertake."

Lenni exploded: rope after rope of hot sissy syrup splashed on to his slim white chest, some of it even hitting his creamy cheeks. It was the most intense orgasm of his life. Lenni sighed contentedly and closed his eyes.

~~~~~

His revelry was interrupted by a noise. He swiveled around on his chair to see his mother smiling wickedly at the door, his own cum still dripping off his body.

"My, my Lenni dear," she commented as she walked towards him, "you really ARE quite the faggot."

She reached down with a single manicured finger and scooped some of Lenni's cum off his cheek. Her finger glistened as Lenni's clear cum ran down it.

"Don't let it go to waste, princess."

She presented her sticky finger to Lenni, almost touching his lips. Lenni knew what was expected: he opened his mouth and let the finger slide in, sucking on it while holding his mother's gaze, moaning around it like the sissy slut he was born to be.