[Fiction] The Competition

[KittenRose]

It was Saturday morning. Jack woke up early, excited. Today was the Sissy Competition! "Sissy Competition!", he had read the headline last Tuesday. "Come and compete with other sissies. Winner will be rewarded! Everyone will have fun. Except the loser!" He had applied to participate and was told to go to so-and-so place on Saturday if he wanted to compete.

Jack always secretly had sissy fantasies. This was a perfect chance for him to play them out. He had waited impatiently for Saturday, getting more and more horny as the days passed by, unable to think of anything else. What would the competition be like? What would the reward be? What if he lost? The ad did not say and Jack's imagination had run wild.

Jack got dressed and drove to the competition. When he got there he saw a pretty girl waiting in the yard outside a large mansion. He nervously approached her.

"Hi, boy! You must be Jack", she said, smiling. "Welcome to the Sissy Competition! I hope you know what you are in for today?"

"Ahh ... ", Jack replied, nervously, "I am here for the competition. Is this is the right place?"

"Yes! I am Miss Amanda. I will supervise you through the tests. Are you ready to have some fun?"

"Yes, Miss Amanda", Jack stammered, not knowing what was in store for him. He felt really nervous. Amanda was beautiful and the thought of being tested by such a beautiful girl made him excited.

"Good boy!", said Miss Amanda. "First, I want you meet your fellow sissy who will compete with you".

Jack followed Miss Amanda into the mansion and they went into a small, well lit room.

"Meet Daniel", said Miss Amanda. "He will be competing with you today. The two of you will do tasks I set out for you and the winner will be rewarded. Oh", she smiled wickedly, "the loser will be severely punished!"

"Are you ready, boys?". Jack and Daniel nodded.

"Well, I really want to make sure you are ready. Stand straight, the two of you, legs spread a little, eyes closed and hands covering your face. I will take a picture for my records. Ok? Then say loudly 10 times 'I am READY Miss Amanda!' Go on, boys!"

The two boys stood as ordered, hands covering their faces, each saying loudly "I am ready Miss Amanda".

When Jack opened his eyes he gasped. Miss Amanda had stripped down to her corset and panties. "You like what you see, boys?" she smiled.

"Well, the winner will see a lot of me as they go along. Ok, time to start stripping! Don't be shy, boys", she ordered Jack and Daniel, "strip down to your underwear! Lets see what you got. Don't be shy!"

The two boys stripped down nervously, putting aside their clothes in a basket.

"Good boys!" said Miss Amanda, seeing Jack and Daniel in their underwear. "Now, boys, cover your face with one hand and grab your crotch!", she ordered.

"Let me take a picture for my records", she said. "Oh, you can squeeze your cock and balls and get yourself hard! And, I want to hear the two of you moan. Imagine I am squeezing your cock and moan in pleasure as you feel my hands on your cock!"

Jack's heart was thumping. He felt very exposed and vulnerable, standing in his underwear next to another man, in front of a beautiful girl. He and Daniel started moaning, quietly at first, and then louder as each wanted to please Miss Amanda.

"Now boys, you know what comes next, don't you?". Amanda laughed. "Yes, you guessed right! Off with your underwear! Let me see those little sissy boi clits! Awww. don't feel shy, take 'em off. Quckly!"

Jack glanced at Daniel, hesitating. He knew he had to obey promptly. Even though he felt nervous, he quickly pulled down his underwear, tossing it into the basket. Daniel did the same. Both of them were now naked, faces red in shame as Miss Amanda smiled wickedly, looking at them.

"Ha, ha ha", she laughed. "Look at you two! Naked and exposed in front of me!"

"Come on, let me see who is bigger! The baby dick boy will have to leave!"

Two two naked and shamed boys stood in front of Miss Amanda as she looked at them. Both were hard and erect. Jack glanced over and saw that his cock was bigger than Daniel's. He felt excited and glad that he would get to stay while Daniel must leave the competition. He would have Miss Amanda all to himself!

"Ok, boys, stand with one hand covering your face and one holding your boy-clit. I need another picture for my records!", ordered Miss Amanda. "And, as you stand say loudly, 'I LOVE being naked in front of you Miss Amanda' ten times. Make me believe you"

Standing as ordered both boys repeated that loudly. When Jack opened his eyes he saw that the basket of clothes had disappeared.

"Oh Daniel!", said Miss Amanda, "You are so ... tiny! Time for you to go for your punishments. My friend Miss Julia will take you now". A tall and beautiful girl came in and took Daniel away. Jack was now alone with Miss Amanda.
[To be continued if there is interest]

[KittenRose]

Jack, naked and exposed was getting very nervous.

"You are all mine now, boy!", Miss Amanda smiled, teasing Jack. She was touching herself and had a naughty smile on her face. "Daniel did not make the cut. Poor boy, he was too small for my taste!"

"Now your real sissy training will begin. Are you ready?", asked Miss Amanda.

"Yes, Miss Amanda", Jack replied, not sure what to expect.

"Well, you know what a sissy really loves? A cock! Well, you will come to love cock by the time I am done with you! Come on, show me how you love a cock", she said, handing Jack a dildo, "look into my eyes as you lick and kiss the cock. Put yourself into it, make me believe you really love cock!"

Jack took the dildo and start kissing and licking it, getting it wet. He always thought himself straight, but this was getting him really hard and he started to stroke his own cock as he licked and kissed the dildo, moaning and slurping as he got more and more into the task.

"Good boy! I see you will make a perfect little cock-hungry sissy", laughed Amanda, "but you have a lot to learn and a long way to go!"

"Now, you know that the best place for a cock ... oh, I mean the second best!", she smiled wickedly. "is a sissy's mouth! Take that cock and suck on it, push it deep into your throat, lick and suck like a sissy desperate for hot cum in its mouth!"

Jack, desperate to please Amanda started to suck the dildo, pushing it deep into his mouth, gagging on it. As Amanda encouraged her he pushed it deeper, sucking it harder, licking the dildo desperately. Drool was dribbling down his chin and on his face, but he kept going, thinking of nothing else but pleasing his tormenter.

"Well done my little cock sucking sissy slut!". Amanda took off her corset, revealing her amazing boobs.

"Now you know that a sissy's mouth is the second best place for a cock, right?", she laughed as she played with herself, teasing him. "What is the best place for cock, boy?"

Jack did not know what to say, and hesitated a little. "The best place for a cock is my ass, Miss Amanda"

"Good boy! What a smart sissy. I think you will be perfect! Well, I want you to put the wet and slick cock into the best place, ok?", she teased in a silky voice. "Do it slowly and lovingly and push it deep inside!! Oh ... and as you do it say loudly 'The best place for a cock is my sissy ass, Miss Amanda!'"

Poor Jack! He felt pathetic and desperate. He had never fucked his ass with a dildo, and normally he would have been disgusted by the idea. But Amanda seemed to have hypnotized him and he would do anything to please her. He took the dildo and slow pushed it into his ass. Slowly, teasing his ass and pushing it in a little, pulling it out, pushing it deeper, till it was fully inside. He was moaning loudly "The best place for a cock is my sissy ass, Miss Amanda!" in a desperate and loud voice, again and again.

"Good boy! What a nice sissy to have a hard cock stuffed up your ass!", laughed Miss Amanda, as she took of her panties and got down on the floor, spreading her legs a little. She was now completely naked, and Jack could hardly take his eyes off her.

"Oh, you can stare at my wet pussy, sissy boy. Sadly, you will never get to touch!"

"Ok, now you will pull the dildo out of your ass completely, and then shove it quickly back deep into your ass. Fast! Do this till your ass is raw and gaping! And, oh, I want to hear you enjoying the fucking!"

Jack could not believe he was doing just as ordered. He pulled the dildo out and shoved it back in his ass again, moaning loudly as he did so, really getting into this as he did it faster and faster.

"Awww. such a sweet sissy fucking yourself with the dildo! Didn't I tell you that you will come to love cock?"

"Yes, Miss Amanda", Jack said to his own disbelief, "I have come to love cock"

"Good boy! But, now it is time to take care of your other bits! Get as hard as you can, boy", she ordered. "Stare at my pussy and imagine how wet and warm it is. Wouldn't you love to bury your face into it?"

Amanda got up and walked over to Jack. She had a pair of shoe laces in her hands. Holding his cock in her hand she tied the laces to his cock and balls, making it tight. She then took a small dumbbell, tying it to the other end.

Poor Jack! his cock and balls were stretched out, pulled down by the weight.

"Good boy! Now, I want you to do a short jog. Jog in place. Let the weight swing from your cock and balls! I want you to feel the pain!"

Jack started to jog in place, the weight swinging, making him cry in pain. "Oh fuck it hurts, Miss!". But he kept going, knowing that he had no choice and must do as he was told, despite the pain.

"Awww. Does that hurt your little cock, sissy?", asked Miss Amanda as she got on all fours, teasing Jack. "Well, at least you get to see my boobs! Poor 'little' Daniel is being punished even harder!"

"Thank you, Miss Amanda", Jack moaned, staring at her boobs.

"Oooh, it's ok. You can stare at me", she winked. "Now, take the weight off. We don't want your cock to fall off!", she laughed.

She got up and fetched a large box of clothespins, and put a couple on each of Jack's nipples. Cupping his balls she put a few on them. Jack felt desperate from the pain but loved the feeling of Amanda's warm hands on his cock.

"Now, lets do some exercise, ok, sissy?", ordered Miss Amanda. "Give me twenty jumping jacks followed by 10 crunches!"

Jack, desperate to please and despite the pain, obeyed like a puppy. The clothespins bit deep into his nipples and balls, driving him into deeper and deeper pain.

"Well done, sissy boy!", laughed Miss Amanda, seeing poor Jack in pain. "I hope that did not hurt too much!"

"Now, lets continue with your training in loving cock, ok? This time, you will show love to two cocks!", she laughed, handing Jack two large dildos.

"Well, shove one cock deep into the best place and the other into the second best place!", she ordered Jack. "You will lick and suck on one cock while fucking yourself with the other. Go on, show me how a real sissy sucks and fucks at the same time! And moan, bitch!"

Jack, desperate to plead pushed one dildo into his ass and started licking and sucking the other. In his desperation he was making moaning and squealing noises. He was now fucking himself in the ass slowly and at the same time his head was bobbing on the second dildo. Faster and faster, moaning louder and louder he kept going, a part of him not believing what he was doing, but the rest of him desperate to please this beautiful young woman and obey her every command.

"What a good sissy! Sucking and fucking like a pro. But you still have a long way to go boy!", laughed Miss Amanda.

"Now, you know what humiliates and shames a sissy the most?"

"I ... I don't know, Miss Amanda", Jack said, hesitating.

"Well", she smiled wickedly. "When a cock goes from a sissy's ass to his mouth!", she laughed.

"Now, lets practice that, shall we?", she asked. "Shove the dildo into your ass, deep and tight. Now, pull it out and quickly shove it into your mouth! Then, out of your mouth and back into your ass. Keep doing this again, and again. Till your ass hurts from the pounding and your mouth is filled with the taste of your ass!!"

Poor Jack! He could not believe what he had to do. Desperate to please, however, he pushed the dildo deep into his ass and pulled it out, quickly shoving it into his mouth. His mind filled with disgust but his body was so horny he kept doing it, getting hard and erect.

"Ha, ha ha", laughed Amanda as she got on all fours, teasing Jack with a view of her ass. "Nice job. I hope you like the taste! As a sissy you better get used to it!"

"Now, lets do something else, ok?", she said. "Put the dildo on the floor, pointing up. Squat, getting your ass just above the head of the cock. You know what comes next! Sissy will ride the dildo cow-sissy style! Oh, and make sure the clothespins on your balls and nipples are nice and tight"

Jack put the dildo on the floor and slowly pushed it deep into his ass. Desperate to please he started to ride it, slowly at first but then faster and faster. He could not believe how good it felt, to be fucking himself like this in front of Amanda. The clothespins on his nipples and balls hurt, and he felt shame at being turned into such a submissive sissy, but he did not want to stop.

While Jack were riding the dildo Amanda changed into a new outfit. "Good job, my sissy cow-girl! You rode the cock soooo well. Awww", she teased him.

"Ok, now, back to your little boi-clit. Now, I know you must be getting desperate. So, let me give you some relief ... or not!" Amanda laughed.

"Ok, shove the dildo deep into your ass. Close your eyes and imagine a real stud fucking your sissy ass and stroke your cock slowly as you imagine him reaming you. Stroke slowly at first and then faster and faster. Edge but then stop! No cumming yet!! Then, edge again. And again. And again!!"

"Oh, and when you are close to an edge, shout out 'Oh fuck, I am so close'", she ordered.

Erect and hard, Jack closed his eyes and started to stroke himself. He could feel his ass throb from the dildo as he stroked. He was so desperate that he edge very quickly and moaning shouted "Oh fuck, I am so close". So close to blowing his load! But he knew he would be in a lot of trouble if he came without Amanda's permission.

"Good boy! Does your little sissy cock want to blow its load? Awww", she teased Jack.

"Yes, Miss Amanda. My sissy cock is throbbing to cum. Please may I cum?" Jack begged, desperate for relief, not sure how long he could last. "Please, Miss, please let me cum!"

"Not yet, my sissy pet", laughed Miss Amanda.

"First, we need you to get use the taste of cock! Take all the precum and rub it on the dildo. Rub the dildo on your cock. You know what comes next! Shove it in your mouth and suck and lick your juices off the dildo! And tell me how much you love the taste of cock"

Jack, desperate and out of his mind with lust, did as he was told. "I love the taste of cock, Miss Amanda", he moaned, "Please let me cum now!"

Miss Amanda got back on all fours, ass facing Jack. "Don't you want my ass so bad?", she smiled. "Not today, sissy boy!", she laughed.

"Now, get down on the floor and lay on your side. Lift one leg up and fuck your ass with the dildo. And hold the other one in your mouth! Show me how a sissy will get his ass fucked as he gets his mouth stuffed!"

Jack had though he would get to cum. He was going insane with desperation and frustration, but knew he had to obey. He got on his side and with his legs spread he used one hand to fuck his ass with a dildo, shoving the other into this mouth. He was moaning now, drooling all over himself and the floor as he desperately sucked on the dildo.

"What a good boy! Your training is coming along so well". Amanda smiled wickedly. "But, lets have some more fun with your sissy boi-clit now!"

"Ok, so this time, I want you to edge with your left hand! And, use the right hand to fuck your sissy ass!", she ordered. "Oh, and edge and stop. Edge and stop. Edge and stop!"

It took Jack only a few seconds to get to the edge, and he was now breathing heavily, desperate to control himself from blowing. "Please, Miss, I need to cum now!" he begged.

"Awww my sissy slut, I don't think you can hold it any longer!", Miss Amanda laughed, as she got on her back, raising her legs and giving Jack a view of her pussy and ass.

"I think it is time for your reward. But first, beg me to let you cum!"

"Please, Miss Amanda", Jack begged, desperate to cum, and the sight of Amanda on her back driving him insane with lust. "Please may I cum, please please Miss Amanda, I am a pathetic sissy who can't hold his load any longer"

Hearing Jack beg so desperately, Miss Amanda got up and opened the door. "Well. Yes, you may but", she smiled, "you must do it while staring at Daniel's ass!"

She laughed as she brought in Daniel, naked and shamed. "Present your ass to Jack, Daniel", she ordered. Daniel obeyed, getting on all fours his ass facing Jack. Poor Jack, his face was red from shame and desperation. He could not believe he would be jacking off while staring at another guy's ass. He always thought himself straight, but Amanda had turned him into a desperate little sissy slut, not caring for anything except obeying her and desperately wanting to cum.

"Now, you will put the dildo on the floor and ride it like the champion sissy cow-girl you have become", Amanda ordered Jack, "and you will use your hand to stroke and push yourself over the edge and squirt all over Daniel's ass as you ride the dildo!", she laughed. "Start at his ass. A sissy must crave another man all the time!"

Insane with desire and desperation, Jack started to ride the dildo, stroking himself faster and faster, staring at poor Daniel's ass. As he got closer he started to moan and grunt. He closed his eyes as he got to the edge and all of a sudden, in a flash of electricity that ran down his body he blew his load. Desperate, he squirted all over Daniel's ass, covering it with hot and sticky cum. Poor Daniel, he felt so ashamed and humiliated as Jack came on him, getting his ass and legs dripping with cum.

"Well done, my sissy boy, I hoped you enjoyed your reward!"

"Yes, Miss Amanda", Jack said in a hoarse voice, "Thank you so much for training and testing me".

"Well, we are not quite done boys!" Amanda laughed. "True sissies who love cock and cum while craving another sissy's ass must only wear panties. And, if you are good boys and want Miss Amanda and her friends to play with you again, you will always wear panties, ok? A real sissy has no need for men's underwear."

"Yes, Miss Amanda, I will do as you say", said Jack.

Amanda handed a pair of panties to both Daniel and Jack, and they slowly put them on. Jack's panties was pink and frilly and the poor boy felt so ashamed to be wearing them.

"Awww ... you two sissies look so cute, all comfy with your little boi clits tucked away in girly panties!"

"Oh, as Daniel lost to you he gets to wear super-cute little-girl panties. He is a funny bunny after all, with such a small boi-clit that it fits snugly even in these tight little panties!"

"You can get dressed, Jack, into your boy clothes", said Miss Amanda, "Daniel, as you lost, your clothes have been destroyed and you must dress up in the nice dress we have for you. I guess it is time for you to be a public sissy!"

As Jack get dressed into this clothes, Miss Amanda helped Daniel into a brown low-cut dress. She made him put on black tights and then completed his outfit with a cute scarf.

"Aww. You look so cute, Daniel". Amanda laughed. "I hope no one recognizes you as you go home!"

Miss Amanda turned to Jack and said, "Good job, boy. You win. If you are a good boy and practice your sissy skills, you may even get to play with my friend Miss Rose. Do you want to meet her?"

"Yes, Miss Amanda", Jack said, "I will be a good sissy and I would like to meet Miss Rose"

A beautiful and completely naked girl walked in and laid down on the bed. "Hi, I am Rose. I hope you enjoyed your competition and training with Miss Amanda!"

"Yes, Miss Rose", Jack said, staring at her beautiful body, "I did"

"Well, if you remain a good sissy, you will get to train with me next time!", she smiled. "Bye. See you next time!"

[If you want to know what happened to Daniel while Jack was being used by Amanda, let me know!]

[MisterDare]

I would like to know what happened to Daniel.

[TheForeverEater]

Same^^^^ what happened to daniel