Chapter 9 – Home Alone

As he drove home, Tyler was uncomfortable as he sat on the butt plug. His mind was still a bit fogged and so he had to drive very slowly, eliciting angry honks from many cars behind him.

At home, he sat quietly through the dinner his mother had prepared. His father noticed nothing, but his mother’s eyebrows rose when she noticed his thinned eyebrows and the clear polish on his nails. After dinner, she drew him aside and hugged him. She held up his fingernails and asked him if there was anything he wanted to talk about. She told him that she was very understanding, and accepting, and if he had anything he needed to tell her, it was okay. Tyler stammered, that everything was fine and then ran upstairs to his room and cried softly on his bed.

After a half hour of sobbing, he went to his computer and inserted the DVD he had been given. He removed his jeans and the pair of panties he had been wearing. As he sat in front of the computer, the butt plug finally felt comfortable inside of him. There was a password on the DVD. It took him a few tries before he guessed the password: Tylerkins! This opened a file directory labelled Limited Access. When he checked the file directory, he found that the directory was full of video files and individual picture files, as well as links to several websites. There were obviously other sections locked by more passwords.

He browsed a bit and discovered that the entire directory was full of videos and pictures of sissies and gay men, servicing large black cocks. His own internet surfing had concentrated on women and black cocks. But now Rebecca wanted him to look at sissies like himself submitting to those beautiful black dicks.

Some of the videos showed women forcing their husbands to submit to superior blacks. Some showed young men resisting, but eventually adoring the cocks. A few of the videos were how-to videos, showing sissies how to dress to accent their femininity while still being a boy – adding a bit of swish to their walk, adding a little lisp to their speech.

Tyler was fascinated and watched for two hours, all the time slowing playing with his cockette. He browsed amount of the material which he could get at. He suspected that, once given the passwords, he had many many more nights of… enjoyment… to come.

And at last he did cum. While watching two very cute sissies on their knees, sharing a large black cock between them, each in turn excitedly gobbling up the cock in their mouths, taking turns sucking on the large black nut sack! Finally as the large gorgeous cock spurted its jism over the faces of the two pretty men, Tyler’s own prickie exploded its pent up juices!

*****

Chapter 10 – Reaction

Next morning Tyler showered and got dressed for school. As he had been told to do, he pulled on a pretty pair of panties under his jeans. His first day panties were pale blue. He also put on the low heeled sandals. Lastly, he inserted the butt plug. To do this he had to scrounge around in his mother’s cabinet until he found some Vaseline which he used to lube his ass.

In the bag with the panties had also been a few feminine beauty supplies with a note from Peggy as to how to use them, and a note from Rebecca telling him he HAD to use them. He moisturized his face , and used a tiny bit of perfume. He also used a bit of gel in his hair to hold it in a more feminine style.

As he gingerly lowered himself on his chair at the breakfast table his mother, Mary, gave him a kiss on the cheek and a tender hug. Fred Roberts, his dad, had his face buried in the morning paper and never noticed anything. Tyler was very conscious of his clear coated finger nails and even more of his powder blue toenails which showed through the sandals. He just hoped no one at school would notice.

But they did, immediately. As he walked to school, Dexter jogged to catch up to him, but then gave a startled exclamation, “What the fuck, Tyler! What happened to you?” Dexter had notice the painted toenails right away. He also figured something was different with Tyler’s face, but could not pin down just what it was. Tyler blushed in embarrassment.

“I lost a bet with Jack,” he said. So I have to paint my toenails like a girl for a week, and wear these stupid shoes so that people can see!” Tyler tried to just laugh it off.

“Oh, cool! Jack IS a bit of a prick, isn’t he? But, a bet is a bet!” Dexter laughed. The two pals walked to school together. Dexter did wonder however why is friend walked with his ass wiggling though!

In classes, most of the guys smirked at Tyler’s appearance. Most of the girls came up to him and told him he looked cute today. The girls noticed his shaped eyebrows and all commented on his new cologne! Tyler repeated the “Jack bet” story and everyone thought it was a good laugh and that he was a good sport to go along with it. However the girls did giggle at the tiny diamond studs in his ears – he had gone very far in losing his bet!

When he saw Lebron or Tyrese in the halls, he managed to avoid them by walking into a classroom, or once even climbing into his locker! Rebecca seemed to not be around that day.

Just after lunch he encountered Jack, who was walking arm in arm with his latest girlfriend, the redheaded Daisy Sunshine. Tyler was with Dexter and Bull at the time and Jack good-naturedly corroborated Tyler’s story about the bet! Daisy gave Tyler a hug and whispered in his ear, “You make such a good sissy Tylerkins! Rebecca told me you would be coming out a bit more! I’m SO happy you want to be who you really are!”

Jack took Tyler aside and asked him “What the hell is going on?” But Tyler just hung his head in shame. He could not tell his rival what had happened to him!

What WAS happening to him? Why had he allowed Rebecca and the black brothers to push him this far? Yes, he had gotten obsessed with looking at all those black cocks on the internet. Yes, he was fascinated by the real cocks of the two brothers. But how had it come to him melting in the boy’s arms, and allowing them to put their cocks in his mouth?

At the end of the school day his head was surprisingly clear and he was thinking straight. He went into the school washroom and ran a comb through his hair, arranging it back to his regular masculine Tyler style. He removed the tiny stud earrings from his ears and threw them in the trash. More importantly, he went into one of the stalls and removed the ass plug. It followed the earrings. Back at his locker he removed the sandals and put on a spare pair of sneakers. The sandals ended up in another waste bin. When he got home he was going to throw out all the panties and toiletries Peggy had given him. And that DVD was going to go in the trash too!

He was also going to call up some of the girls in class and get himself a date for Saturday night! He was not going back to the Hunter mansion and the Washington gardener house!

It felt strange at first, walking home. No butt plug and no sandals with a bit of a heel – but only for a few moments. Then he was fine, and was striding purposefully. He was mad, and he was going to do something about it!

*****

Chapter 11 – Scolded

When he got home, he was surprised to find Rebecca sitting at the kitchen table, talking to his mother. And they were both smoking!

“Mom, you don’t smoke!”

“Tyler, there are a lot of things that you don’t know about me.” replied Mary Roberts. “Rebecca arrived a couple hours ago. Smithers, the Hunter butler, helped her bring a lot of packages over here for you. She has been telling me a few things about you that have helped make many things clear about your behaviour the last couple of months….”

“Mom! Whatever she has been telling you isn’t true!,” started Tyler. But he was stopped by a stinging slap to his cheek from Rebecca.

“Tyler, where are you sandals and your earrings!”

“I threw them away. I’m not wearing any damn girl stuff!” His face was slapped again, this time by his mother!

“Tyler, you will NOT raise your voice in this house! Now apologize to Rebecca, for shouting at her!

Tyler glared at both his mother and Rebecca. If they thought that he…. His mother slapped him again, this time much harder. “Apologize, now!”

Startled, Tyler hastily blurted out, “I’m sorry, Rebecca. I shouldn’t have….” Again he was viciously slapped. His mother’s face was very angry now.

“Address her properly, Tylerkins!” said his mother through gritted teeth! On no, thought Tyler, she knows!

His face bright red, both from the slapping and from shame, Tyler said, “I’m sorry, Miss Rebecca, for raising my voice to you. But I don’t want to be wearing all that girl stuff!”

Rebecca ignored Tyler’s words. Instead she looked in his eyes, closely. “Tylerkins, did you take your pill this morning?”

“No… no Miss Rebecca. I didn’t remember that I had the pills. Why do I have to…..” Rebecca cut him short. “Go get your pills and bring them here!”

Tyler hurried to his room where he noticed a number of empty boxes. He grabbed the pill vial and took it back down to the kitchen. When he entered, he was surprised to see Rebecca’s blouse open exposing her large round fake breasts. More surprising, Mary Roberts was running her hands around those breasts and tweaking the nipples as Rebecca moaned softly.

“Oh Tylerkins, aren’t Rebecca’s new breasts just lovely! You know when I was younger, I thought about having implants. But your father could not afford them!” she sighed.

Rebecca buttoned her blouse back up. She took the vial from Tyler and handed him two pills and a glass of water. “Swallow these,” she commanded him. “Normally you should take one in the morning and one at night, but you missed your morning pill, and I think you need some reinforcement!”

Reluctantly, Tyler downed the pills. Mary took the vial from Rebecca and said that she would see that Tyler took his pills regularly from then on.

Rebecca took Tyler by the hand and led him back upstairs to his bedroom. By the time they got up there, Tyler was already beginning to feel disoriented. He was finding it a bit hard to focus on any one thing in particular. It was soothing to listen to Rebecca. Rebecca opened Tyler’s dresser drawers to show him the new pairs of panties that she had bought him today, plus many packages of new stockings. His closet held new pairs of slim feminine styled pants – some jeans, some capris, even a few skirts! A variety of blouses hung on hangars.

On one of the shelves were lined up numerous female beauty products. Rebecca explained there had not been enough room in the single family bathroom, but she wanted Tyler to use the various skin softeners, hair conditioners, body lotions every day.

As Rebecca was showing these things to Tyler, and explaining to him how to use them and that he MUST use them, Tyler noticed that his mother was leaning against the doorway, observing while smoking a cigarette.

Rebecca opened a jewellery box on the top of his dresser, showing him the various earrings and bracelets. She took a couple of small hoops and threaded them through the piercings in his ears. “I had not planned on you wearing hoops yet,” she told him, “but since you threw out your shiny studs, I think you should wear these to school tomorrow!”

She then told Tyler to take off his pants which he did. “Well at least you are still wearing your panties!” she exclaimed. “Take them off too!”

Tyler looked over at his mother, not wanting to expose his penis in front of her. “Do as Rebecca says, Tylerkins. She knows what is best for you!” Mary Roberts smile turned to a frown as Tyler dropped his panties to the floor! “My, he IS small isn’t he?” she said as his two inch soft penis was exposed. Tyler tried to cover it with his hands, but Rebecca swatted his hands away.

“Thankfully Tyler’s father Fred has a nice big prick,” said Mary. “Hmm.. I wonder if penis size comes through the female side of the family, like baldness. My momma always told that my father was small dicked!

“Oh you poor boy, Tylerkins! No wonder you’ve been fascinated by the Washington boys!” said Mary as she gave her son a hug! “Oh, but you have such a nice round ass! I can see why those boys might be interested in you!”

Tyler could not put any clear thoughts together. The double dose of pills was keeping him calm and confused, but also horny. Even though it was his mother hugging him, his cockette rose to its full four inches!

“Tylerkins, I want you to lay across my knees!” commanded Rebecca. He looked at her puzzled, but his mother took him by the arm and pushed him down across Rebecca’s lap. “You were a bad little sissy today. You did not take your pills like you were told to, and so you had a fit and messed up your hair and threw out some of your things!”

“So you are getting a spanking!”

“No, Miss Rebecca! I don’t want to be spanked!”

“Oh hush up, Tylerkins,” his mother scolded him. “All sissies need to be spanked regularly!”

Rebecca started to paddle his bottom with her hand. He squirmed on her lap as she counted out ten, then twenty, then thirty spankings. When she reached fifty, his bottom was bright red, and he was sobbing softly. “Mary, would you bring me Tylerkins’ new hair brush from over there please?” asked Rebecca.

Brush in hand, Rebecca told Tyler,” I was going to stop there, Tylerkins, but I see that you also removed your butt plug! You definitely need to be punished for that!” And she began swatting his ass vigorously with the back of the brush!

“He was wearing a plug this morning?” asked Mary. “I THOUGHT he was walking with a bit of a wiggle!”

Tyler was now openly crying as Rebecca wailed on his ass heavily. Where it was previously just red, his ass was now definitely turning purple in places, bruising!

When she stopped, she commanded Tyler to lay on the bed, with his ass in the air.

“Mary, will you open that drawer for me please?” Rebecca nodded towards the bedside drawer. Tyler’s mother stubbed out the last of her cigarette and pulled open the drawer. Her eyebrows rose as she gazed upon an assortment of dildos and other sex toys. “Hand me the bottle of lubricant please and… hmmm.. I think just the smallest ass plug will be fine please?”

Tyler knew what was coming and squirmed. Even in his fuddled state he did not want a butt plug up him again. Rebecca poured some lube on his ass and tried to smear some into his asshole, but Tyler was resisting too much. “Could you give me a hand Mary?”

Mary had been holding onto a large lifelike black dildo and reminiscing. It had been a long time since…. But Rebecca’s question brought her attention back to the moment. She swatted her sissy son’s ass and then took the lube from Rebecca’s hand. “Hold still, Tylerkins. This is for your own good!” she exclaimed as she forced two of her fingers into her redheaded son’s ass!

“Oh mom! I’m not a … not a sissy! I don’t know why everyone…” Tyler sniffed! Rebecca held his ass tightly as Mary took the plug and then none too gently shoved the plug into his ass. His rectum fought the invader very briefly and then the plug settled into his ass.

Tyler sat up, tears running down his cheek.

“Of course you are a sissy!” his mother scolded him! “I know what you have been doing up here in your room at night all school year! Ever since those Washington boys moved to town, and you haven’t been able to get a date with Peggy or Rebecca, you’ve been up here wanking to pictures of big black cocks!”

“Mom, no! I haven’t been…. ”

“Yes you have! And quite frankly, after seeing your own little thingie just now, I can see why! How big is your little prickie?” she asked him.

“F… four inches when it’s hard!” he sobbed.

Mary turned to Rebecca. “You let him put that little thing inside you?”

“I took pity on him, what can I say?” replied the dark haired girl.

“How big is Jack, Tylerkins?

“I.. I don’t know! And don’t call me that name!”

“You’ve been in the showers together often enough. Guess!”

“I don’t know.. six inches maybe?”

“You never looked closely? You never touched his cock?” asked his mother.

“No! Guys don’t touch guy’s cocks!” he answered back.

“And how big are Lebron and Tyrese. How long are their cocks?” Mary asked?

“I don’t know… maybe eight or nine…”, started Tyler. “Don’t tell me… show me with your hands!” commanded his mother. Rebecca giggled.

“Um, about this big,” Tyler held his two palms about ten inches apart.

“And how do you know that, Tylerkins?”

“I see them in the shower. I see them every time we have practise!”

“Is that when their cocks are soft?” asked the older woman. “Or when they are hard?”

“Hard. When they are soft, they are large anyway. But when they are hard, they get real big!”

“And have you just looked Tylerkins? Or have you touched them? Have you touched those large black cocks”

Tyler could not look his mother in the face. “I.. I’ve touched them. They made me hold their cocks and wank them!”

“And did you like touching their cocks, Tylerkins?”

“No… no.. I did not want…”

“Oh Tylerkins, that’s not true!” chimed in Rebecca. “Mary you should have seen the look of lust on his face when he had BOTH cocks in his hands at the same time! And then he kissed Tyrese’s cock! And then he sucked both of those wonderful black cocks!”

“Is this true Tylerkins?” his mother asked. “Did you suck their cocks”

“Yes, momma” he whispered

“And did you like sucking on their cocks?”

“Yes, momma!”

“Will you suck their cocks again, when you are told to?

“Yes, momma.” Tyler was in tears again. He did not know why he was saying these things. But, it felt right to admit to his yearning.

“Are you a man, Tylerkins?”

“Yes, momma!”

“No you aren’t Tyler. Didn’t you just say that men don’t touch other men’s dicks. Much less kiss and suck on those dicks?” she asked.

“Yes momma. I mean no momma. I mean….”

“Tylerkins. You are not a man. You are a sissy. And more than that, you are a faggot, a fagboy!”

“Yes, momma, I am a sissy.” Tears came to his eyes again. His mother hugged him to her breast and patted his head as he sobbed against her chest. “Miss Rebecca saw that you are a sissy, and is doing her best to help you adjust. I think you should thank her, don’t you?”

Tyler turned to Rebecca. At her stern gaze, he realized what she wanted and he knelt in front of her. His eyes focussed on her shoes as he said “Thank you Miss Rebecca. Thank your for helping me be a good sissy!”

“You are welcome, Tylerkins! Now, your mother and I have a bit more talking to do. I want you to spend the next couple of hours in front of your computer. If you want to jerk off, you can do so. You’ve been a bad sissy today, but I think you have earned a bit of a reprieve now. Your password for today is “sissy”. Your previous password won’t work. Put on your headphones and watch the screen!”

Tyler sat in front of his computer, very aware of the plug in his ass. He typed in the password and the screen came to life. Soothing music played and he could faintly hear some words in the background.

In the doorway, Mary asked Rebecca, “Are you sure this is right for him?”

Rebecca replied, “Absolutely! As soon as Lebron and Tyrese started at school, everyone noticed that Tyler could not take his eyes off of them. It was sissy-love at first sight! All we are doing, is helping the sweet thing along!”

“You said that Fred has a Hunter meeting tonight and won’t be home until late? So why don’t you and I take this thing into your bedroom,” she said, taking the long black dildo from Mary’s hands, “and see if we can’t find a good use for it!” Rebecca leaned in and kissed Tyler’s mother hungrily on the lips.

Mary unbuttoned Rebecca’s blouse and she fondled the teen’s hard breasts. “You know, back before I met Fred, I had a black boyfriend. We were very serious about each other, but black and white couples weren’t very well thought of at the time, and so we broke up. Fred’s cock is a decent size, but nothing like Dwayne’s!”

Tyler did not notice this exchange. His attention was focussed on his computer monitor. He had at first been disappointed to find that he no longer had access to the files from the previous night, the files showing sissies sucking the cocks of superior men. Instead tonight’s files were entirely pictures and videos of sissies, individually and in groups, displaying their masculine, but feminized, beauty – their lovely made up faces, their clothing, their posture and demeanour.

There were no cocks, there was no sex. Oh yes, some of the sissies displayed their little cockettes seductively and shyly. Some thrust their delightful brown puckers at the camera. Some of the sissies were being kissed and fondled by handsome men. But there were no nice large cocks on display.

There were lots of videos with makeup tips for sissies. And howto videos showing how a sissy should walk in heels, and how he should stand to accent his femininity. Pictures and videos showed sissies choosing their clothing for the day to please their men, their mothers and their wives.

Three hours later, Mary brought a sandwich and glass of milk up to her son’s room. She was walking a bit unsteady and if she had looked in the mirror she would have realized that her lipstick was very smeared.

When she opened Tyler’s door she discovered him asleep on his bed. There was a makeup mirror set up beside the computer screen and lipsticks and eyeliner cases spread about. Looking at her sleeping son, she saw that he had been practising. His face did not look very good, but she would help him until he got the hang of it.

She also noticed that he was wearing a pair of dark stay up stockings and a pair of pink panties underneath the nightie he had put on.

Looking in the garbage bin, she found a couple of tissues which were hard and caked with cum. He had evidently jerked off to the sissies he had been watching this evening.

She gave her sissy son a kiss on the forehead, pulled the covers up over him and turned out the light.

*****

Chapter 12 – School with a New Attitude

Tyler woke the next morning to the sound of his alarm. When he looked at the time, he discovered it was an hour earlier than his usual time. He was surprised to find himself wearing a nighty and even more startled to find his legs encased in stockings! His legs DID feel very nice as he rubbed one leg up the other and his little cockette began to tent his panties.

He sat up and when he saw the computer and the make up mirror beside it, his memory of the last evening slowly returned, though it was all a fuzzy blur. He remembered spending hours watching and admiring sissified males pose and prance across his screen, and he remembered practising putting on makeup.

His face! He looked in the mirror and he saw that his face looked a mess. What had he been doing?

There was a light tap at the door and he turned in time to see his mother step inside. She had a glass of water, a pill, and a stern look on her face. Before she could say a word, he took the pill and washed it down with some water. He even opened his mouth to show her that he had swallowed it.

“Jump in the shower, Tylerkins,” said his mother. “I set your alarm early so you have plenty of time to choose the right look for the day!”

Tyler showered, using the special soaps and conditioners that his videos the previous evening had shown him.

When he dried himself off he wrapped a towel around himself and made his way to his bedroom where his mother had laid out his clothing for the day. Mary helped him pull up the sheer flesh coloured knee-high stockings. Tyler blushed as he pulled up the pink panties and nestled his little cockette inside. He was a bit disturbed by the words emblazoned on the panties; “I love boys” but he figured… he hoped… that no one else would be seeing those panties!

He pulled on a pair of light blue Capri pants which left his lower calves and ankles exposed. Mary handed him a dainty gold ankle bracelet to fasten around his right ankle, and he dimly remembered it from two days earlier at Rebecca’s. A closer look revealed that there were inscriptions on two small plates in the chain. One simply said “Tyrese” and the other said “Lebron”.

Mary sprayed a bit of perfume on Tyler’s hairless chest before helping him don a short top which left his hips and belly button exposed. “Hmm… said his mother. If you are going to wear this top very often, I think you may have to get your navel pierced! An exposed midriff demands a bit of jewelry!” Tyler blanched at the idea!

Marcy checked Tyler’s finger nails to be sure that his clear nail polish was still fine. She filed a couple of rough edges on a couple of nails. She brushed out his hair and then used some hair spray to hold it into a more feminine style.

Turning her attention to his face, Mary applied a very little bit of foundation, to mute her son’s freckles a bit. She added just a small thin bit of eyeliner and a just a hint of eyeshadow. She finished with a very very pale lipstick – barely visible, but Tyler could feel it there and it enhanced his femininity.

Lastly she had him step into a pair of sandals similar to those he had thrown away the day before, with just a small heel.

Stepping back to admire her handiwork, she exclaimed, “You look lovely Tylerkins. Clearly a boy, but with just the right amount of girl to make people start to wonder about you! As the days go by, we will start being a bit bolder about your fashion choices!”

Looking in the mirror, Tyler’s fogged mind registered what his mother was saying. He was pleased that he was as cute as many of the boys and young men he had seen in the pictures and videos last night! Downstairs at the breakfast table, Fred Roberts noticed nothing unusual, as he never lifted his head above his morning paper.

Mary handed her son a small purse filled with makeup and lipstick. He looked for a pocket to hide it in, but had to resort to disguising it amongst the pile of books he had to carry to school.

With his heart in his throat, Tyler set off on the walk to school, his bum swaying as a result of the butt plug that Mary had ensured was secure in his ass for the day!

As usual, Dexter was waiting for his friend along the way. “Still paying off that debt to Jack, Arch? How long you gotta do this, all week?”

“Yeah, at least that long, maybe longer!” replied the redhead, sulkily.

At school, once again most of the guys just avoided Tyler, whereas the girls all flocked around him, complimenting him on his appearance. In classes, sitting on the hard chairs, he was very conscious of the plug in his ass.

Just before lunch he was called out of class to go to the principal’s office. When he arrived he was told to go straight in. Sitting across the desk from him, Mr. Sutherland looked quite stern. “I’ve had several teachers comment on your appearance yesterday, Tyler. I must say I was rather upset. Even if you had lost a bet to Mr. Maris, it was not appropriate to show up looking as you did. And today, you are even more so. It is really not appropriate for a young man to be dressing in such a.. feminine manner!

“It would certainly have helped if this letter had arrived yesterday, instead of this morning!”

“Letter, sir?” inquired Tyler.

“This letter,” said Mr. Sutherland, holding up a piece of paper. “It was delivered by courier this morning. The letter from your psychologist?”

“My psychologist, sir? I don’t have a… ”

“Come, come, Tyler. There is no need to be shy. We here at Springfield High are very modern in our thinking! Dr. Hodgkins has explained about your gender dysphoria. She writes very well you know, taking a complicated subject and making it easily understandable.!’

“Sir, I don’t understand? Am I in trouble?” Tyler began to sniffle.

“No, no Tyler! Not at all. You are welcome to continue to wear what you wish at school. The letter explained that you are undergoing treatment for your desire to change your sex from male to female. Your doctor explained that it will be a long process and that you are to be treated just as you always have been, as a male, but with desires to express your femininity, sometimes modestly and sometimes overtly! “As I said, we are a progressive school and we can bend with the times! You are excused from all phys ed classes and from participation on the basketball team or other extracurricular physical activities requiring you to shower with the other boys. There are only a few months before graduation or I would ask if you wanted to join the cheerleader squad!”

“That is all Tyler, you may go back to class!” As a confused Tyler rose, Mr. Sutherland hastily came around his desk and reached to open the door for him. But before he did he stopped and said, “I must say, Tyler, this has all taken me rather by surprise! I always thought you were quite the lad! But seeing you today… well, you do look extremely cute. I do think your lipstick could be a bit brighter! You know, before I met Mrs. Sutherland, when I was just a young lad myself, I had a brief dalliance with a cute young man who called himself a sissy. I am not ashamed of that, and you should certainly not be ashamed of your own feelings and needs. Good luck to you, my boy!”

Tyler went straight to his locker and dumped his books. It was lunch break and he went to the cafeteria. He had to take his small purse along since it was the only place to carry his money. He stopped off in the washroom to look at himself in the mirror. As he looked at himself critically, it was still like looking through a layer of fog. A small part of his mind knew that this was not quite right. He stared at his face with a critical eye, then opened his purse. He touched up his foundation in places, and then took out his lipstick and applied a fresh coating to his lips. Mr. Sutherland was right, of course, tomorrow he would wear a more visible colour. He patted at his hair a bit, and was satisfied.

When he had his lunch tray, Madge Cantor urged him to join her. He set down his tray and then eased his plugged ass down on the bench. The conversation with Madge was pleasant. Madge had always been nice to him. He might have dated her more if Bull Mason hadn’t threatened to punch his lights out if he caught him anywhere near her. Madge was in fact that last girl he had had sex with and that was several months ago, after Rebecca had cut him off and Peggy had disappeared. As they talked Tyler could tell that Madge liked this new Tyler a lot.

They were interrupted by Rebecca who took Tyler outside where he joined her and a bunch of the other girls who smoked and hung around outside the No Smoking zone beyond the front of the school.

“I’m SO proud of you today, Tylerkins! You are doing so much better today!”

“Yes, Miss Rebecca. I want to please you!”

“Oh, and you are, sweet sissy boy, you are!” The other girls in ear shot giggled at her words. In a quieter voice so that the others would not hear she told him that he was to meet Tyrese in Miss Haversham’s classroom at three pm, when she did not have a class and so the room would be empty.

“Why, Miss Rebecca,” Tyler began to ask, but stopped when he saw the stern look on her face.

“You are not to question me Tyler! You are to do as you are told!” she scolded him. “But in this case I will tell you that you are to be rewarded for being such a good sweet sissy today!”

Rebecca knew Tyler’s schedule and knew that he has a free period at that time. At three pm, Tyler opened the door to Miss Haversham’s classroom and sat down nervously to wait.

He thought of taking his compact out of his purse and using the small mirror inside to check that his hair and makeup were still okay, but then he also began to question why he would do so? His head was clearing again and he began to realize how silly he truly looked!

Just then the door opened and Tyrese entered. Tyler rose and took a step toward the black youth. He opened his mouth to protest, but Tyrese pulled him into his arms and gave him a long lingering kiss. The large black lips overwhelmed Tyler’s own painted lips and Tyrese’s tongue slid easily into Tyler’s mouth.

Tyler pushed back from Tyrese. He uttered a weak, “No! This isn’t right!” before Tyrese captured his mouth again and their tongues duelled. Tyrese reached one hand down to cup Tyler’s groin and Tyler involuntarily pushed his groin into the black teen’s palm. He ground his genitals hard against the hand as he moaned his lust into Tyrese’s hungry mouth!

Tyrese pushed the sissy to his knees and began to unzip his trousers. Tyler protested, “No, I don’t want to do this! I’m not a …. ” but a stinging slap from Tyrese’s hand on his face stopped him.

“Take it out for me, Tylerkins! It’s been two days since you’ve seen any black dick. You must be panting for it by now!” Resignedly, Tyler did as he was told. He pulled down Tyrese’s pants and then his underwear. Tyrese’s wonderful long black dick was already partially hard. He knew this wasn’t right. He knew he should not be so weak. But he also knew that he wanted this.

“Mister Tyrese. May… may I please touch your cock?” he asked demurely.

“Perhaps Tylerkins. Perhaps.” said Tyrese as his own fist lightly ran up and down his dick, getting it hard. “Do guys touch other guy’s cocks, Tylerkins?”

“No, Mister Tyrese,” replied Tyler. He knew where this was leading. He needed that cock in his hand. He WANTED that black dick in his hand. So he immediately went where Tyrese wanted him… “Only sissies touch men’s cocks, sir.”

“And do guys kiss other guy’s cocks, Tylerkins?”

“No sir. Only sissies kiss men’s cocks, sir”

“No Tylerkins, not sissies! Who kiss men’s cock’s, Tylerkins?” Tyrese was now holding his firmly erect cock, just an inch away from Tyler’s mouth. Tyler’s mouth went dry. He needed that cock so badly. He needed to feel it in his hands, and in his mouth again!

“Faggots suck cocks, Mister Tyrese. fagboy, suck black cocks, sir!’

“And what are you, Tylerkins?”

Tyler’s tongue ran along his lips. His hands reached up, almost, but not quite touching that wonderful, lovely piece of black meat! “I’m a sissy, Mister Tyrese. I’m a faggot! Oh please, let me touch your cock!”

“You did that very well, faggot. And very quickly! I expected a bit more resistance from you! Yes, you may take my cock in your mouth, but you can only use your hands on my balls, and on my ass, to pull me in deeper!”

With a plaintive mew, Tyler moved his lips forward and eagerly engulfed the glans of Tyrese’s dick in his mouth. He eagerly gobbled at it, sighing in pleasure at once again having a powerful black cock in his mouth. He knelt up straighter so he could have a better angle to work the cock into his mouth.

Tyler’s hand alternated between toying with Tyrese’s large hanging balls, and holding onto the black man’s ass so that he could get better position on the large cock that he was enjoying sucking so much.

Tyler bobbed his head up and down on the hot piece of meat in his mouth. Tyrese used his own hands to guide the redhead youth’s mouth up and down his shaft, urging the sissy to try to take more and more of the dick into his mouth!

As Tyler blissfully sucked on the cock, his mind was filled with images he had been viewing on his computer screen, of sissies contentedly sucking on men’s cocks. He remembered how they sucked and tried to emulate the cute fagboy on the screen. He knew he had watched several videos on how to suck cocks, how to make his sweet wonderful black master happy. This was right, this was so right! He was in his true and proper place, kneeling at the feet of this wonderful black man, giving pleasure to his glorious dick!

Tyler was in heaven. He could not imagine any place he would rather be! And suddenly the classroom door opened, and Jack Maris and Daisy Sunshine walked in!

“Hey Tyler. I got your note to meet you here. What’s up?” said Jack before he was even fully into the room. “Sweet mother of god, what the fuck are you doing!” were the next words out of his mouth, when he caught sight of his feminized friend kneeling on the floor with Tyrese’s cock in his mouth!

Daisy didn’t say anything. She just gasped and then giggled!

Tyler’s eyes flew open and he pulled his mouth off of Tyrese’s cock. He blushed in embarrassment and tried to get to his feet, but Tyrese’s powerful hands held him to the floor. “Jack!,” cried Tyler, tears coming to his eyes, “it’s.. it’s not what you think!” “Not what I think, man? Are you kidding me?” asked Jack. “I find you wearing makeup and sucking on a black dick in a classroom! Why isn’t it what I think! You’ve turned into a fucking fag!”

“No, no… it’s not what you think!,” Tyler was in full tears now. But the string of precum that connected his chin to Tyrese’s dick said otherwise!

“You are sick, Tyler!”

“Oh Jack. We can’t judge those who are less fortunate,” Daisy told him. “Sometimes we all have to give in to our urges to be who we want to be!”

“Well, secko here can be who he wants to be, but I don’t have to stand here and watch!,” said Jack as he stormed out of the room. “Are you coming?”

“No,” said Daisy. “I think I WILL stay and watch. Is that okay Tyrese?”

“Sure thing, sugar. Tylerkins likes having an audience, don’t you, sissy?”

Daisy took a seat and watched as Tyrese tilted Tyler’s head up and then pressed his cock back into the crying youth’s mouth, commanding him to suck!. Tyler pulled back, and between his sobs, he said “Why?”

Tyrese looked the redheaded lad in the eyes and said, “You were a bad sissy yesterday, Tylerkins. You had to be punished. So we let one of your best friends know who you are…. what you are! Remember this when you want to get feisty! Now get your mouth back on my dick, I need to blow my nut before next class begins!”

Daisy grinned as she watched the chastised sissy resume his cock sucking. But this time it was not gentle. As he continued to sob, Tyrese took charge and began to fuck his cock in and out of Tyler’s mouth. Tyler seemed on the verge of protesting the roughness at times, but he remembered his place. He attacked the cock with his tongue and he sucked and relaxed at the right times. Finally, finally, Tyrese’s leg muscles tightened, and suddenly the black teen’s cock jetted thick streams of cum – the first two landed in Tyler’s mouth and he reluctantly swallowed, but then Tyrese pulled back, and the last several jets of cum landed on Tyler’s face, one landing across his left eye!

Sated, Tyrese pulled up his pants and left.

Daisy looked at the dejected sissy and took pity on Tyler. She helped him to his feet and wiped away some of the cum with a tissue. She then led him down the hallway to a girl’s washroom where she helped him to splash water on his face and wash off the remaining cum. Several girls wandered in, and quickly left again in confusion.

Tyler finally managed to compose himself. Daisy took his purse from him and helped him fix his makeup. She handed him his lipstick, and dazedly, Tyler put a thin coat of wax on his lips. He had one more class to finish before he could go home for the day, and Rebecca would be sitting right beside him. He had to look his best, or he knew she would find a way to punish him.

Daisy gave the sissy a kiss on the cheek and he went off to his final class of the day, cork heels click clacking on the linoleum floors and plugged ass swaying!

 

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