Introduction

The Dare

One rainy afternoon, with revision books strewn about and with very little actual studying happening, Freddie looked at Carl with a sly grin. “Go on, Carl, I dare you—go to the Prom wearing a dress. Actually-you would look more stunning in a dress than most of the girls at the Prom.” Said Freddie with a grin on his face, as he turned to face Carl while he and carl were both sat across a table from each other, with books strewn across it.

Carl nearly choked on his crisps. 

“Not a chance, mate! I’d rather turn up in my birthday suit, than do that.” Remarked Carl, almost half choking. But Freddie wasn’t one to let a dare die quietly. He cackled, “Where’s your spirit of adventure?” Said Freddie, sounding quite serious now. Carl simply could not believe what Freddie was suggesting. “I simply don’t have any.” Replied Carl, rather bluntly. “I’m serious man, you should so totally do it. Wear a dress to the Prom I mean.” Remarked Freddie in an even more serious tone of voice. “No freaking way and No means no. Got it?” Remarked Carl sounding quite furious with Freddie. 

“Okay, okay. Don’t get your panties in a twist.” Said Freddie as he burst out laughing.“Ha, ha, very funny. I am not wearing any.” Remarked Carl in annoyance. “That’s a shame. I bet you would look cute in a pair. Panties I mean.” Said Freddie, laughing his head off. “Are you out of your God damn mind?” Snapped Carl. “Hey! Lighten up buddy, I am just messing around with you.” Said Freddie, shocked at Carl’s reaction to his sense of humour. “Yeah, well don’t.” Carl retorted sounding the most annoyed that Freddie had ever seen him be. “Okay, I’m sorry.” Said Freddie, trying to defuse the situation, but sadly Carl was not having any of it. “Get lost. In fact, get out of my house.” Remarked Carl in anger. Freddie simply got up from behind the table and quickly left, not saying another word, as he did not want to get into a fight with his best friend, trusting that Carl will come around eventually.

Freddie’s Plan

Unbeknownst to Carl, Freddie had a mischievous plan brewing. That evening, he paid a visit to Carl’s Mom, Lisa, who was folding laundry and humming to the radio. With a conspiratorial tone, Freddie announced, “Lisa, I think Carl’s got something he wants to tell you. He fancies wearing a pretty-pink dress to prom, but he’s too shy to ask and not only that, but he also told me in confidence that he secretly wants to be a girl. But he’s too afraid of what you would think of him.” Said Freddie, sounding perfectly serious.

Lisa’s eyes lit up. “Really? Oh, bless him. He’s never been one for following the crowd.” Said Lisa who was touched by Freddie’s news. She made up her mind there and then. She was going to go out and get for carl the most-prettiest pink Prom Dress that she could find and was glad of the fact that her husband, Carl’s father was not alive, as he definitely-would not agree to her buying a Prom Dress for Carl.

Carl is going to be in for a real shock.

The Prom

Two days later, Carl returned home to find a shimmering pink dress draped across his bed, sequins glimmered in the afternoon sun, there was also a pair of pretty pink satin panties to go with the dress and a modest pair of pink 5in high heel shoes, with a note, which read: “I am so proud of you! I can’t wait to see what you will look out in your new beautiful clothes. You are just going to simply dazzle at the Prom Tonight. Love, Mom.”

Carl stared at the note in horror. “Mom! What’s all of this?” Carl asked, as Lisa got back home and went immediately up to his bedroom, expecting Carl to be in the Prom Dress and everything by now. Lisa, beaming, replied, “Don’t be shy, love. Just be yourself! You’ll look fabulous tonight.” Carl looked at her in annoyance. 

“Did Freddie put you up to this?” Remarked Carl angrily. “Come now Carl, don’t get angry. You are such a lucky boy to have a friend like Freddie. He told me about your wish to go to the Prom in a pretty-pink Prom Dress and that you also wanted to be a girl.” Said Lisa in a happy tone of voice.

“What?” Remarked Carl, real angry now. “That is a fat-based lie Mom. You really didn’t believe him, did you?” Asked Carl, sounding utterly furious. “I would not see why Freddie would lie to me. He’s almost like having a second son. There is no shame in you wanting to be a girl sweetie.” Said Lisa, calmly. 

“Mom. I seriously and truly have no wish to be a girl, and Freddie is going to get it when I next see him.” Lisa took hold of Carl and shook him. Now, now young lady. It is un-lady like to be violent. You may have convinced your self that you do not want to be a girl. But tonight, you are going to the Prom as one and that is final. Maybe After spending a night as a girl, you will change that mixed up mind of yours.” Replied Lisa in a deadly serious tone of voice.

“But Mom.” No buts, or you will end up getting a smacked one, butt, that is, if you do not do as you are told. Now do I have to dress you or are you going to dress yourself?” Lisa asked, getting cross with Carl. Carl gave a heavy sigh, as he took the items that were on his bed, and he left his bedroom to go and change in the bathroom. He later came out. “Satisfied!” Exclaimed Carl sounding annoyed and unhappy to be in a pink Prom Dress and high heel shoes. Just then, Lisa suddenly pulled up the skirt of the dress. “You will go and change out of those boxers right now young madam, girl’s do not wear boxers.” Said Lisa firmly, disappointed to see that Carl was wearing his blue boxers underneath the pink Prom Dress

Carl let out another heavy sigh, then he went back out of his bedroom, back into the bathroom and then he returned-back to his bedroom. Lisa lifted up the dress and was happy to see that Carl was now wearing the pink panties. “There, that’s better now and you look very beautiful my dear.” Said Lisa “I look and feel ridiculous.” Replied Carl in an unhappy tone of voice. “Nonsense my dear and I won’t have you say to the contrary.” Lisa warned. Carl simply lowered his head, but Lisa lifted it up. Keep your head strait sweetie. Don’t slouch, girls don’t slouch. Okay now, give me a little walk.” Said Lisa. Carl simply could not believe his ears. “What?” He said in complete and utter shock.

“Come now, don’t be shy sweetie. Give me a little walk across the carpet here.” Said Lisa with enthusiasm. Carl heaved yet another sigh, but he complied with his mother’s wishes and so he began to walk across the carpeted floor of his bedroom. “Oh dear, no, no, no. Not like that. You are doing it all wrong, never mind, I am sure you will learn all in good time, but there’s no time for me to teach you how to walk in heals. Or even put make up on you. I took the liberty to book a car to come and fetch you and take you to the Prom.” Said Lisa in sheer delight, but inwardly, Carl was hating every moment of this.

Soon, a black car, not a limo, but it was a posh car at least, that came to pick up Carl. 

The driver was a lady driver, as Lisa knew that a male driver would not simply understand seeing a boy in a dress, a pink one at that. The lady driver could not help but smile and tried very hard not to burst into a fit of giggles, the moment she got out of the car and saw Carl looking pretty in pink, she opened the side door open for him to get into the car. Carl did so, awkwardly at that. “You look real pretty tonight miss.” Said the Lady driver. Carl wanted to correct the lady driver, but he did not want to cause a scene, all the while thinking inside of his head. ‘I’m going to kill Freddie the moment I see him.’

“Thank you.” Replied Carl in a somewhat delayed and awkward tone of voice. It was not what he really wanted to say, but there was nothing else that he could say. The lady driver said nothing else, she just simply drove the car. 

It arrived at the location of where the Prom was being held, which was a dance hall that held weekly dancers there. It had been hired out by the organisers of the Prom night, just for that night. Carl awkwardly got out of the car, as soon as the lady driver had gotten out of the car and came to open the side door for him. “You’re going to knock them dead in that killer dress.” Said the lady driver with a smile. But this time, Carl did not reply, he felt a little cold as the dress was a backless dress with two thin straps.

Carl really hated it, but most of all, he really hated having to wear the pink satin panties, as they were unexpectedly, giving him a hard on. “Dam these panties, they are effecting me in ways that just isn’t natural.” Said Carl underneath his breath, as he walked into the dance hall, if a little bit wobbly on his feet. The shoes were a struggle to walk in with just being 5in. The moment he accidently stumbled onto the dance floor, everyone all suddenly stopped and looked at him and then they all suddenly burst into fits of laughter. “Hey Carl. Nice dress.” A girl suddenly remarked in-between fits of giggles. “You’re looking really sexy tonight, Carl.” Laughed a boy, but he obviously didn’t mean it. But the line got everyone all laughing again and that was the point. 

Everyone could not stop laughing. Carl did not know what to do. Just then Freddie came up to him. “Wow! You look really-pretty.” He said and oddly he meant it. He actually-could not believe his eyes, even without make up, Carl looked quite stunning in the pink Prom Dress. Carl was at least grateful of the fact that his mother did not insist on putting make up on him. “Shut up, this is your fault.” Carl growled at Freddie, indicating the dress that he was wearing and everything else. He wanted to punch Freddie in the face, but his arousal was annoying him beyond mention, and he was trying so very hard to ignore it.

“I had to get you in a Prom Dress somehow. Besides, you really do look better than most of the girls here in that dress.” Replied Freddie, again, meaning every word of it. He actually-could not help himself, he really did like Carl in that Prom Dress, which even surprised him. Everyone had all stopped laughing now and the music resumed playing. Freddie suddenly took hold of Carl’s hand. “Would you care to dance with me?” Freddie asked, Carl gave him a glaring look. “What? Are you out of your God dam mind?” Roared Carl in anger. “Now, now, temper, temper. Do you really want everyone here to start staring at you and laughing at you again?” Remarked Freddie and then he suddenly added. “You’re the only girl anyway that does not have a partner to dance with.”

Carl did not know what to say. He wanted to correct Freddie on saying that he was a girl. He was just simply a boy in a dress, panties and heels. “Fine, I’ll dance with you.” Remarked Carl, somewhat begrudgingly. He desperately needed to take his mind off his arousal, if that meant having to dance with his best friend, now worst enemy, so be it. Everyone at the Prom had a really good time, to some extent, as Carl had danced with Freddie, it helped a little bit to take his mind off, of his aroused state. He was glad for the whole Prom to be over, as everyone began to make their way home. But before Carl left, Freddie suddenly grabbed him by his hand.

“Before you go. I would like for you to go out on a date with me.” Said Freddie sounding deadly serious. “Would you go out on a date with me?” He asked, expecting Carl to say flat out loud no. But he didn’t. “Yes, okay I’ll go out on a date with you.” Said Carl, not knowing why he just agreed to that, he was too focused on his arousal more than anything else. Freddie looked genuinely surprised but smiled. “Thank you, it’s a date then. I will come and pick you up tomorrow at say seven O’clock?” Said Freddie, still smiling. “Yeah, sure.” Replied Carl, he just simply wanted to get back home and get the dam dress off, but more than that, the dam panties too. The same lady driver that had brought him to the Prom had come to take him home, for which Carl was grateful for, not wanting to have to walk it back home in those heels, but also not wanting to be seen and get laughed at again.

The Date

Carl was finally glad to get back home. He was so tired, that he actually-did not bother to take off the dress, or the panties for that matter, he just simply went straight up to bed. He woke up the next morning, only to find that he had fallen to sleep in the dress, not only that, the panties too, which were now oddly stained. Carl nearly almost freaked out the moment he saw them, but he simply decided to calmly take off the dress and those panties, he had at least somehow in his tired state, managed to kick off the heals, as they lay strewn across the carpeted floor.

Carl dumped the panties and the dress onto the floor; he went and took a bath. When he came back, when he came back, the dress and the panties were gone, so were the shoes. His mother must have come in and took them away, but he was glad of that fact, as he actually-did not want to see those things ever again. He got dressed into his usual own clothes and he felt good about that. He came-downstairs, to the smell of a cooked breakfast. “Good morning, Mom.” Said Carl sounding quite happy. “Good morning sweetie.” Said Lisa in a happy sing-song tone of voice. “Would you please not call me that.” Said Carl with a groan. “Why not, you’re my daughter now.” Replied Lisa.

“No, please, not that argument again Mom. I already told you last night, I have no desire to be a girl.” Carl moaned. “I know that you feel that way right now sweetie. But in time, you’ll soon come around. Oh, by-the-way, I got a phone call this morning from Freddie, he told me the good news, that he’s taking you out on a date and that you agreed to go out with him.” Said Lisa sounding dead happy about that fact. Carl lowered his head with shame. “I wasn’t in my right frame of mind when I agreed to that. Mom, please do me a favour, ring Freddie back and tell him to council that date.” Replied Carl, not at all sounding so happy. He was in a good mood until his mother had mentioned the whole date thing.

“I will do no such thing. You are not going to break an agreement, regardless of your state of mind. I am washing your dress and panties as I speak, so that they will be ready for your date tonight.” Said Lisa, dead firmly. “What? No not the dress and panties again. Mom, I can’t wear those again, besides, they were just for the Prom night.” Remarked Carl in complete dismay. “I know sweetie, but the Prom dress and those panties are the only girl’s clothes that you have right now, so you must wear that dress and those panties again for your date tonight. Though don’t you worry sweetie, I will go out later on today to buy you a whole row of dresses and panties, and other girl’s clothes, etc.” Replied Lisa sounding happy again.

“But Mom I don’t want or need any other girl’s clothing, etc.” Remarked Carl, sounding quite unhappy. “Nonsense. I won’t have any arguments from you; do you hear me? And you will go out on that date tonight.” Remarked Lisa in a dead serious tone of voice. Carl simply could not believe what was happening. Why did Freddie have to go and lie about him wanting to be a girl? It looked like he could not get himself out of the situation that Freddie had put him in. “That’s it, if I am going to go out on a date with Freddie, I am going to tell him that we are no longer friends.” Remarked Carl to himself, sounding real-unhappy. He and Freddie had been friends since childhood and now all because of a lie as well as running his life completely, that friendship would simply end.

Lisa went out shopping, as she said she would do so. Carl simply stayed up in his bedroom all day, playing video games. He was not particularly looking forward to having to wear the Prom Dress again for his date, but more than that, those dam panties. If he did not wear them, his mother would be sure to check that he was wearing them, which she did, when the time came for him to go out again. Carl simply groaned at the fact of his mother lifting-up the skirt of the dress to check and see if he was wearing those dam panties and he was. Tonight, will be the night that he would end his long-time friendship with Freddie.

Freddie arrived on time, and he was happy to see Carl wearing the same dress again. “You look positively beautiful my dear.” Said Freddie and he meant it, Carl did not say anything, until his mother cut in. “Carl or should I say Carla. Don’t be rude, thank him for the compliment that he just paid you.” Said Lisa, who was disappointed in her newfound daughter. “Thank you.” Said Carl to Freddie, but he did not really mean it, but he did not want to cause a scene, he simply wanted this whole date thing to be over and done with.

Freddie took Carl by the hand and led him to his car. Carl was at least grateful for the fact that he would not have to walk anywhere. Freddie opened the passenger door for Carl to get into, he did so, some what reluctantly though, as Freddie then got into the driver’s seat and began to drive off. Having to sit next to the guy that he hated the most was hard for Carl, but, Carl did his best to grin and bear it. Freddie pulled outside of a fancy restaurant, which was called Loue’s Restaurant. Freddie held Carl’s hand all the way into the restaurant, Freddie even pulled out a chair for Carl. Carl sat down to the table that was now in front of him.

This was it; this was his chance to end his friendship with Freddie and thus end this ridiculous date. But the way in which Freddie kept looking at him, was putting him off. “I am so glad that you agreed to this date Carl. I mean Carla. I know that I could have any girl that I want. But I do not want any other girl. I want you.” Said Freddie, Carl said nothing, as he simply could not believe what Freddie had just said to him. Freddie however, continued. “I should say more to the point, I want a girl boy like you. I am surprised myself, but that said. I really do not want a real girl. You are the perfect Sissy, that I never realised that I needed my whole life, until now.” Said Freddie.

Freddie waited for a response, like for Carl to say something, anything, even walk out on him. But Carl simply sat there dumb founded and not knowing what to say. So, Freddie continued to speak. “I do not want you to become a real girl, as you are more than girl enough for me.” Freddie suddenly stopped talking, he leaned in close to Carl and then he kissed him, right on the lips. At first, Carl sat rigid, not really wanting to be kissed, but the longer that Freddie kissed him, something in Carl suddenly changed, he started to kiss him back, not knowing how or why, but he was somehow falling in love with Freddie. 

Freddie stopped kissing Carl, who suddenly spoke. “Since I am going to be your Sissy girlfriend, do not call me Carla, instead, please call me Cassey.” Said Carl in a sweet girl-like voice. Freddie simply smiled, though he was surprised by the sudden change in Carl, but he welcomed it. “Cassey it is then. Did you mean it, about you being my Sissy girlfriend?” Asked Freddie, worried that Carl might be playing a prank on him. Cassey looked Freddie in his eyes. She leaned in and kissed him for a moment, then broke the kiss and replied. “I honestly do not understand it myself, but yes. I really do mean it.” Said Cassey with genuine honesty. Freddie leaned into kiss Cassey back. The date had gone far better than Freddie could have possibly have ever imagined to how it would go. The date ended on a high note and Freddie was more than happy to return Cassey home.

Cassey had news to tell her mother, who surprisingly took the news better than she thought she would. “So, you’re a Sissy. That’s even better.” Said Lisa with a smile and then she gave Cassey a great big hug. “Really?” Asked Cassey in complete surprise. “Yes Cassey, really.” Said Lisa sounding quite happy. The time that Cassey had spent with Freddie was the moment Cassey had found quite latterly, love in the most completely unexpected way.

The End

Freddy convinced Carl’s mom he wants to be a girl and go to the prom as one. She applied force to make him go in spite of Carl’s denying he wants to be a girl. Carl is caught wearing boxers with his dress instead of panties. Mom provided a chauffeur to drive him to the prom. Carl is enjoying wearing those pink panties. It turns out Freddy really likes Carl and becomes his dance partner. Big surprise is they are going on a date. Great update to your sissy story. The image is perfect too. Hugs Baby Butch