C3Verse: Alex's Convention Storyline PREQUEL
[CROSSDRESSING/CROSSPLAY TG STORY]
{11,400+ Words}
Disclaimer/Spoiler Alert: Contains Crossdressing and Sexual Themes. This story is Explicit.
From the Author: "Hello, I'm Xarek.
Welcome to the Prequel of the first story I ever wrote on DeviantArt, The Warrior Queen.
This story takes place four years before the rest of the storyline I will now be referring to as C3Verse: Alex's Convention Storyline or AC followed by the number where the story takes place with a decimal point before the part in that story (AC#0.1 means Alex's Convention #0 "Prequel" Part 1)
The C3Verse represents an alternate reality to our own where I have written and have plans to write Three Separate Storylines: Convention, Community, and The ?????(not revealed yet). I have several stories in two of the storylines that you can check out on my page or find down below in the description where I will always post the next story in the Storyline (if it is out).
As this is technically the first story chronologically in the C3Verse, I need to explain some things.
The C3Verse takes place in a fictional alternate reality to our own where in this world there are only about Three Billion people in the year 2013 due to a disease that wiped out half the population of Earth in the early 1900's.
Technology, science, and medicine have come far since the epidemic in this peaceful world. However, fictional entertainment in all its various forms has only become popularized in the last few decades.
There has never been a major event of a Costume, Comic, Movie/TV, Anime or any other variation of a multicultural and multinational Nerd/Fan/Geek Convention or huge gathering. Several small scale events were held, but mostly in tight knit groups and followers of single fandoms. Nothing like the grand conventions that have spread across our own world today.
That is until a man by the name of Maxwell Traven decided to change that and started work in preparation for the first one of its kind, to take place in 2013 in his home city of Seattle.
Before the Seattle Costume and Comic Convention became a huge event in the C3Verse, where a near-hundred thousand gathered from around the globe to share their interest in fictional worlds and characters, a few thousand people came to a half open convention center for the first Event of its kind for the single day it was going to take place.
One of their number was about to experience his first time Crossdressing at the said event.
Welcome to the C3Verse.
(Sorry for the long intro, but I thought it was necessary. I promise I will be cutting back after this. Be sure to read to the end and the description to get to part two)"
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Wednesday, July 3rd, 2013, Time: 19:01
Three Days Before the First Costume and Comic Convention (or C3)
The Johnson Residence in Maple Leaf, Washington
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Alexander John Johnson glanced from his sister April to his sister's best friend Whitney Fourie.
"You're kidding right?" He said with a sarcastic smile on his face.
April brushed back her naturally ginger hair from her pale and freckled face and was completely serious as she told him, "Nope."
"We aren't." Whitney agreed. Her also natural and curly red hair bounced on her Almond colored face as she nodded firmly.
Alex turned his attention back to the hand he currently held from his personally built deck for Wizards and Warlords. His deck Hero was already in play, and the swift combo sword-ring-sword he could pull out on his next turn would guarantee his victory over a novice like Whitney. Most likely on his next turn.
He had just barely taught her how to play almost an hour ago after all.
Glancing back up at the two women, Alex saw April quickly drop the devious smile she had flashed at her friend, while Whitney held a complete stone face expression.
Even more suspicious now, Alex decided to make sure he heard his sister correctly. "So, if I win, you agree to buy me a ticket to that new Costume and Comic Convention coming to Seattle, and you will both buy and wear whatever I want you to wear?"
Just barely out of high school, Alex didn't have a job yet, but April did at a hospital call center and just received a large bonus for being employee of the month last month. She loved spoiling her little brother as they were also really good friends.
In fact, Alex considered April to be his best friend with Whitney being his friend by association. At least he considered himself and Whitney to be friends. He was never sure about what Whitney thought of him as he just always tagged along on some of the things Whitney and April did and it had never seemed to bother the two girls.
April corrected him with a finger pointed upward for emphasis, "We will wear what you want us to wear 'within reason'. I don't want to go as a Joygirl Kitty or some other slutty costume you think I should wear."
Whitney thought aloud. "I wouldn't mind wearing Sultana's Belly dancer costume from The Warrior Queen Returns. I think I'd even dye my hair to go a brighter red for that. We could even put a blonde wig on you April and have you dress as that English Handmaiden from the same game."
As Whitney turned to April with a smirk, April glared at her while Alex's heart fluttered at the thought of his secret crush looking like his favorite video game character in the series' most sexual costume Sultana wore. Not that all of The Red-haired Arabian Queen's costumes weren't sexy, he just thought the almond skinned and curvy Whitney would look great in any of them despite her being a couple inches shorter than he was and far from the muscular physique needed to properly pose as the six-foot-three Warrior Queen.
Though the fact his crush had just used her secret nerdy knowledge also made him feel warm too.
April, Alex's senior by four years, went back to the subject at hand. "And if Whitney wins. You wear whatever we want you to, without complaint. Though I will still buy everything because I'm nice like that."
Alex tried to add, "Within Reason?"
Whitney shook her head again, "Nope. Sorry dude, but because it's me and your sister in the deal, you don't get that choice. Do you agree or not?"
Alex swallowed. He knew his sister could be downright diabolical when she wanted to be, but she was also often overconfident. Though he trusted his sister with his life and knew she wouldn't try and publicly humiliate him outright or out of carelessness.
And he had just taught Whitney how to play Wizards and Warlords after all.
He knew his secondary deck that Whitney was using pretty well with its deck hero Revlen the Elf Lord. There were only two possible combos Whitney could use to stop Alex's inevitable victory with the cards in play. And one of them required a crazy combo that played a card that was currently in 'his' hand, after playing a specific card he only had one of in the deck she was using. Whitney wouldn't even know what those cards were.
He stared into Whitney's Beautiful Brown eyes to see if he could read how she thought she would win this, and felt his cheeks blush as she smiled kindly and winked at him without giving him any indication what her plans were.
Trying and failing to keep his emotions in check, he told them, "I agree to your terms."
Now it was April's turn to look at him suspiciously, making him squirm under her gaze.
Finally, she spoke in a fake British accent. "Swear it. Swear it on the great sword Excalibur."
April knew her brother too well.
Alex loved The Knights of Camelot TV show too much and April knew if Alex Swore by Excalibur, he would endeavor to keep his promise even though he was eighteen and stuff like that may have seemed childish to anyone that didn't know how nerdy he was.
Rolling his eyes and taking a deep breath, Alex recited in his own English accent he always developed every time he watched the show, "I swear by King Arthur's blade, Excalibur, that I will keep this oath."
Satisfied, his sister finally smiled at him excitedly and turned to Whitney who told him, "Your turn."
Considering the stakes of the game now, Alex knew he had to defeat Whitney at all costs. He wouldn't be able to do it this turn with how protected her own deck Hero was, but he could lay the grounds for a final victory on his next turn by preparing two spells that would eliminate her defenses, let him draw four cards on his next turn, and hopefully be able to kill Revlen whose health had already been damaged.
When Alex had his plan set, he told Whitney with a grin, "Your turn."
Whitney continued to remain expressionless and played a card from her hand without even glancing at it. "I activate the agent, Tower Thief."
Alex's heart immediately sank.
He slowly handed Whitney the cards in his hand. He watched and knew exactly what card she selected to play immediately.
Alex knew he had just lost.
"I use the spell: Sword Prison." Whitney told him and finally broke into a wide grin. "Did you know I was 'Wiz&War Club' champion for a whole year straight in high school?"
Alex looked at her horrified, "But... But... I taught you how to play."
She shook her red mane of curly hair. "No, you just assumed I didn't know how. Never once did I say I didn't know how to play. You know you shouldn't make rash judgments about people. I do have to say, you were a great teacher. Much better than the guy that taught me forever ago. And you do make a couple of pretty decent decks. I'm rather impressed. I could even tell you were holding back on me."
Alex's mouth was open in shock as she removed his swords that were currently the only defense for his hero Slara the Battle Sorceress.
Whitney mercilessly attacked his favorite card, killing his Hero, and winning the game.
The girls high fived and Whitney started putting away his deck.
Alex had lost.
He hadn't lost a game to anyone in well over a year. He had even gone way easier than he would have because he thought Whitney was a newbie. But she was probably way better than him, actually brave and social enough to be in the Wiz&War Club. And also, be its champion. Whitney had played him, and he couldn't be more impressed and excited that the beautiful and unassuming girl with African Heritage was even nerdier than he had previously thought.
And more devastated that he had lost the bet and was at his sister's and her friend's mercy.
April patted him on the shoulder. "Well, it looks like you get to wear whatever we want Al. Don't worry, I will be sure to pick someone you really like. And to be a good sport, Whitney and I will match you."
Alex stared down at his slain favorite card who was smirking up at him. "Can I at least play again? I was taking it easy on you."
Whitney froze. "Only if the outcome of this one doesn't change. This is just to redeem your game, not to give you a way out of your promise."
"Fine." He started prepping his deck for the next battle and asked, "So what will I be wearing?"
April exchanged glances with Whitney while they both remained expressionless. Alex hated how good they were at acting and angrily thought to himself, 'Stupid Drama Club People.'
April turned to him and said, "Since mom and dad will be going out of town for the weekend, I think we should work on your costume all day Friday to make sure everything is perfect for Saturday. But you won't get to find out until then, so don't ask. Whitney and I will buy everything tomorrow."
Alex sighed in defeat and got ready for his rematch.
Unfortunately, he destroyed Whitney in their second game. Though he was partially convinced she let him win.
____
Two Days Later
Friday, July 5th, 2013, Time: 08:00
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"WAKE UP ALEX!"
Alex jolted awake as both April and Whitney shouted at him and giggled. He glared at them and checked the clock. "Eight?!"
Last night had been a late-night watching fireworks from his porch and playing video games with April and Whitney while his mom and dad had gone away for the weekend. He still felt groggy from going to bed at 01:50 late last night.
Alex had been happily sleeping in every morning since he and April got back from his Graduation Cruise last week. His parents couldn't go, so his grandparents agreed to take him and one friend. As Alex considered his sister to be his Best Friend, and didn't feel like inviting anyone else, he had happily let her come with him.
He was really regretting that decision right now as he rubbed the sleep from his eyes while yawning.
April smiled brightly at him. "Do you remember our agreement? Or do I need to go grab your broken sword?"
All three of them glanced towards the wall mount that Alex's broken plastic Excalibur was on.
He had destroyed his prized possession after he had used it too aggressively during a mock sword fight. He was really devastated by its loss, especially because in the show it was supposed to be indestructible.
He growled, "No I remember. Who am I going as?"
April smiled and turned to Whitney, "Could you give us a minute Whit?"
"Of course. I'll be downstairs. I bought breakfast for you Alex, so you better not hate me." She winked at him and left them alone, shutting his door behind her.
April turned back, suddenly looking very serious. "What we say in the next little bit will stay between us, got it? I promise to never tell Whitney or our parents."
Alex was starting to be filled trepidation as he agreed. "Okay."
She bent forward and whispered, "I know about the swimsuit."
Alex's heart stopped.
His mind went blank, and fear instantly filled his body.
He had tried to be so careful while he wondered, 'How did she know?'
While he sat panicking, April went on. "I found out about it around two months ago. I know you've had a tough couple of months with Fria dumping you for that college guy. And I bet you know our parents are trying to split."
Having known about the divorce for a long time, he also knew that their parents had been trying to keep it from both him and his sister for some unknown reason. Though the signs were all there. He had guessed April knew as well, but this was the first they had ever talked about it to each other, opting to pretend to remain in blissful ignorance.
April went on, "I probably figured it out the same time you did. I saw the way you started treating Dad last year, and I feel the same way. I knew you were struggling and I let a couple of Swimsuit snatches go unnoticed. I even hid the evidence from mom one time when it came back a little... soiled."
When he was still with Fria, she had gotten Alex to try on a pair of her panties for fun the only time they had almost had sex. It had awoken something in him, and he couldn't stop thinking about the silky and amazing way they felt on him. After the breakup, he was doing laundry and found a one-piece green swimsuit April didn't wear too often anymore. One thing led to another, and he couldn't stop thinking about it, so he tried it on, and it became an addiction with how amazing it felt on him as it caressed his body. Which had led him to doing things in it that he definitely didn't want his sister to know like she knew now.
April kept going. "I know how much you like Whitney, and how you stare at me and other girls when you think no one is looking, so I don't think you are gay. You just probably like women's clothes, right?"
He didn't move as he stared fearfully at his bed, unable to meet her eyes. Alex felt very exposed as his sister continued to reveal she knew all his deepest darkest secrets.
She must have seen his affirmation because she continued, smiling kindly at him as she gently grabbed his shoulder. "I get it. I like women's clothes too. You should see my secret stash of lingerie." After a moment's thought she reconsidered, "But you won't, so stay out of it, or you'll regret it."
Knowing that she had him in a corner and could really get him into all kinds of trouble, he finally nodded as quickly as possible.
"Good. So anyway... Alex, you aren't in trouble. And I'm really not mad at you. It's not really a big deal to me, and I don't want you to get in trouble with our parents who have their own problems to deal with. I thought I would help you out today and tomorrow, and dress you up as a girl for the Con. Because you are my brother, and I care about you a lot, we are just going to pretend that this was entirely my idea and it hasn't happened before, so no one will know you enjoy it. You can even pretend to hate it. You're my brother and I love you, so I want to do this for you. No one will ever know about this."
She stood up and took down Excalibur from his wall. She knelt on the ground and offered it up to him. "I swear on the sword Excalibur."
He finally choked out, "You don't believe in that stuff."
"I don't. But I was trying to get you to see how serious I was. I really won't tell anybody."
He swallowed, believing her, but still scared. "I can't do this. I don't look like a girl."
"I believe I can make you look entirely like one. I even looked up some stuff on ShortVids about how to make up your face to do it. No one would know it was you. If you don't look like a girl after your makeover, then we won't do this. But if you believe you do, and don't recognize yourself, I want to take you with us to C3 tomorrow as one of the girls. Whitney and I will never tell anyone who you are and will never speak about this again. What do you think?"
What Alex thought was that he was still panicking with his sister finding out that he had been wearing her clothes and had masturbated in them. Apparently having known about it for a long time.
Though the way April sincerely looked at him without any hint of anger or deviousness made him think that she really did want to just help him try it. And he really did want to try this. He had never worn more than a swimsuit and only wore it a few times over the last few months, but the thought of being able to really dress up as a girl, and having no one be the wiser, really excited him.
Alex wanted to do it. Just this once. To experience what it was like to feel like a girl.
"You really won't tell anyone?" He finally asked.
His Sister stood from the ground and sat next to him on the bed, his broken sword going next to her. "Of course not. Why would I need to? I thought we were close enough to keep each other's secrets. Do you not want to do this?"
He sighed. "I kind of do. I really do like wearing your swimsuit. I'm really sorry for borrowing it. I have just always been curious."
"Well then, let's try it. You seem so depressed lately that I want to cheer you up. And I love hanging out with you. I was so happy you let me come on the cruise with you. I wanted to also return that favor and let you do something you really want too that would normally get you in trouble or people asking uncomfortable questions. I spent probably too much money to have this anyway, so I was hoping you wouldn't back out. I think this is extremely exciting. So do you want to go with it?"
He tried not to look too eager to fully dress up as a girl with his sister's help as he said, "Fine. We'll try it."
"Promise me that you will try everything and honestly try to be like a girl. The more you can act like one and the more confident you are, the more people will believe you are one."
"Fine. I promise to try, but I better look good."
April broke into a smile and hugged him tightly. "I will not just make you look good; I'll try and make you look hot... I always wanted a sister."
He pushed her away and said firmly, "Just for two days, then we're done."
"Of course. Unless you really want to do this again. Just promise me one more thing."
"What?"
She became serious again and glared at him. "Don't you dare go looking for my lingerie and stay out of my underwear."
He rolled his eyes. "I promise April."
Alex did notice that she didn't say stay completely out of her clothes, but he didn't bring it up.
____
Alex followed his sister downstairs to see Whitney playing on her phone with a half-eaten breakfast burrito in front of her. She was sitting next to half a dozen shopping bags from various places and a box from the online retailer JoyShip.
Whitney looked up and asked, "Is he going to keep his promise and dress like The Acrobat?"
April smacked Whitney's shoulder as she walked by and sat down. "I wasn't going to tell him who we were going to be yet, just that he had to dress as a girl. Way to spoil the surprise, Whitney."
Trying to look upset, Alex's heart raced. If April could make him look like the Acrobat, that would be so awesome and exciting.
He sat down and quietly opened the burrito Whitney slid over to him with a smirk.
The Acrobat, or Maggie Mclain, was a comic book character that was very sexy and immensely popular. She was originally from the Comic Series 'The Guardian of Detroit' but was loved by fans so much she got her own comic series. Then she made it to Animated TV, then the big screen in the Live Action Movie 'The Guardian' and into various video games.
The Acrobat normally wore an orange and dark blue bodysuit that helped show her lithe and curvy form and a generous amount of cleavage wearing a mask and blonde wig to hide her features.
Her story was that she was a real Acrobat in the circus that turned to a life of diamond thieving after her circus family died in what was originally thought to be an accident. After getting caught by The Guardian then helping him fight the villain, The Mobster, she started to do more good things and used her skills to become a crime fighter, occasionally teaming up with The Guardian who became her love interest.
Alex also had a childhood crush on the comic heroine and had read quite a few of her comics.
Whitney smiled apologetically to April. "Sorry for spoiling the surprise. So, is he doing it or is he going back on his promise?"
April looked at him and gave him a wink that Whitney couldn't see, before saying, "He'll keep his promise, but he doesn't like the idea of dressing like a girl. We made a deal that he would only do it if we made him look completely unrecognizable."
Alex gave a slow nod in agreement. Then he remembered something April had said the other day. "Does this mean you two will dress up as other women in the Acrobat?"
Whitney gave him a knowing smirk. "Why? Do you think I'd look hot as the Temptress?"
The Temptress was a Jamaican Voodoo Witch that enticed men into doing stuff for her. The very revealing outfit she wore would look really good on Whitney.
Alex must have blushed above the burrito he took a bite of because Whitney said, "I see you like that idea."
April interrupted after taking a bite of her own burrito. "I'll be going as Dr. Kristy Gill before she turns into a sea monster."
Dr. Gill was pretty hot too in her business attire and lab coat and April's red hair was perfect for her. Whitney would need to wear a white wig to hide her own hair, and Alex would need a blonde one or a brown one depending on which costume he was wearing.
The girls sat talking about the show and who else they could dress as, or who they could dress Alex as in increasingly revealing costumes, while they finished their breakfast.
Whitney hopped off the chair excitedly. "Well, shall we get going?"
April turned to Alex, "Ready to be a girl for the next couple of days?"
Honestly more nervous now than excited, Alex told them shyly, "I guess so."
April smiled. "Perfect. The first step is a shower. You need to use all of my women's body and hair stuff, so you smell like a girl. Then I need you to put this on." Under some of the bags, she produced and handed him a familiar green swimsuit. "I don't wear it anymore, so you don't need to worry about girl cooties or anything like that."
To hide his nervousness and excitement about wearing the suit with permission, he said, "Really? I'm not a little kid."
"No but you are my 'little' Brother." April said with a smirk, knowing perfectly well Alex was actually a couple inches taller than her.
He asked, "Why do I have to wear this?"
"Because I need to shave your legs and arms."
Alex's eyes widened. "What?!"
Giving him a devious smile as she threw away their breakfast trash and Whitney started collecting all the boxes, April told him, "If you want to look like a proper girl, you can't have a hairy body. It'll all grow back. I even bought some lotion to help with itching and keeping your skin blemish free. You're lucky you have a mostly hairless chest."
"But why do 'you' have to do it?"
"Do you know how to shave your legs?"
Alex shook his head, knowing it'd be better if someone more experienced did it for him. He had only barely started shaving his face.
He and April left Whitney and went to April's bathroom that was attached to her bedroom. April showed him how and where to use everything he would need to shower. She also gave him a new women's deodorant for after he was hairless.
Before she left, she looked at him with a happy smile. "I'm surprised you didn't complain about having to clean yourself using a bunch of girls' stuff."
"If I'm going to do this, I need to be a girl as much as possible, right? Even smelling like a girl."
"You aren't worried about smelling like me?"
Alex felt his face warm at the thought.
April gave him a knowing smile. "Do you think I smell nice?"
Alex sheepishly nodded.
"Well good. However, you really smell like a guy, so I'd wash everything extra well. We'll be just outside the door so call if you need help."
She shut the door, and he locked it behind her.
____
Alex took a deep breath, smelling April around him, then exhaled through his nose.
He heard his sister through the bathroom door. "Alex, are you done yet? The water shut off five minutes ago. Put on the suit and open the door."
"I can't."
"Why not?"
"The suit is on, but... I have a problem."
"What kind of- oh. I didn't think about that."
His problem was the outline of his erect penis in the green swimsuit.
The smell surrounding him; the perverse excitement of being discovered; his imagination at what he, Whitney, and his sister would be wearing; and the feeling of the tight swimsuit on his body all had a strong effect on him. He didn't exactly want to do what he knew would take care of it with two girls just outside the door.
He heard the girls whispering but couldn't hear what was being said until April told him. "You'll have to tuck it in."
He hesitated, then awkwardly said, "I can't right now."
The whispering began again, his cheeks blushing in the mirror as he realized his own sister and a girl he really liked were talking about his manhood just outside the door.
Whitney finally spoke through the door. "Hey Alex, I was thinking about our game the other night. If you added the spell, Sagrur's Thunderclap to your deck, and could get it prepared, it might help you prevent someone from beating you the way I did."
Alex stared at the door. "Why are we talking about this now?"
"I'm giving you a distraction to help you calm down. Just play along."
Knowing it was for the best, he said. "Okay. What else should I add?"
They talked back and forth for a while as Whitney gave him some good pointers and they even talked about trading some cards later.
April must have been a little bored because she interrupted, "Do you feel better yet?"
The casual talking had helped with Alex's swelling, so he replied, "Yes."
"Good. Now I know this'll be embarrassing, but you need to do this, and I'll talk you through it. Pull down and roll the swimsuit until it's resting on your thighs."
He followed her instructions. "Now what?"
There was a moment's hesitation before April spoke in an awkward voice. "You need to shove both of your testicles into the cavity in your abdomen."
"What?!"
"It's how crossdressers hide their manhood. It's perfectly safe and they will pop back out naturally. I know this is awkward, but you know how tight or small the Acrobat's costumes are. If you don't do this, a... bulge might give you away."
Alex heard in April's voice how much she didn't want to be talking about this with her own brother. He also felt the blood rush towards his penis, so he quickly tried to do what she asked.
It was surprising how easy it was to shove them into himself, with slightly any pain that disappeared immediately. When he released them, they popped back out again, so he slid them back and held it.
"Now what?" He asked.
He heard April take a deep breath. "Take the length and point it towards your back, tucking it between your legs. Pull it back there as tight as you can and keep your legs together to keep it in place."
"How do you know about this?"
"I looked it up, now hurry please. This is embarrassing."
"You aren't the one doing this." He mumbled to himself and followed her directions. To his surprise, it all stayed put.
"Now pull up the swimsuit and make sure it looks smooth. Then I'll come shave you."
Doing so, Alex took a quick check in the bathroom mirror.
He had always been very slim for a guy, never being able to put on much muscle no matter how much he exercised. If you didn't look at his head or hairy legs and less hairy arms, his flat crotch gave him the appearance of a girl that desperately needed some curves.
The thought made a rush of blood head back down to his groin, but with how tight the swimsuit was, it didn't give him an erection. It just made him a little uncomfortable down there.
He quickly opened the door to see Whitney and April sitting on the floor while on their phones.
Whitney took one look at him and wolf whistle, which made April smack her knee and say, "Down girl. Why don't you go prep the next part while I shave him."
Whitney happily agreed while April came into the bathroom and shut and locked the door.
They stood there awkwardly looking at the ground for a minute until April set the shopping bag in her hand on the counter. Then she quickly grabbed him and smelled his body and head.
His sister gave him an awkward smile and said, "Just checking. Now turn the water back on but leave the shower curtain open. Point the head to only cover half the shower and re-wet your body. Just ignore the swimsuit. It's fine if it gets wet obviously."
Doing what she asked made him extremely embarrassed. He was practically getting in the shower with his sister watching. And the wet swimsuit on him felt very erotic, so he tried to think of something else.
Alex asked his sister, "Do you even want to see dad after this?"
April sighed before, to Alex's utter shock, she began removing her own clothes. He was about to protest when he noticed his sister was wearing another one-piece swimsuit underneath the shirt and shorts. He figured it was a one piece for his benefit, because he knew she preferred bikinis lately.
"Sorry," She explained, folding her arms over her chest. "It'll just be easier if I do this in the shower with you. I know how awkward this is, but let's just get through this as quickly as possible and forget it ever happened. Got it?"
The stern look she gave him made him nod quickly. He doubted he could ever forget this, and he believed she wouldn't either.
She grabbed a new razor and shaving cream before stepping into the shower with him, which suddenly became a lot smaller with the two adults inside it.
As she began applying women's shaving cream to his face to remove his slight facial hair, she asked, "What do you know about the reason why they're getting divorced?"
He tried to speak without moving his mouth too much while trying not to look at his wet sister. "I know he has a serious drinking problem. You see how he gets sometimes."
His sister paused their conversation so she could shave his face. She was very gentle and careful when taking the hair off. It was taking all of his self-control to not be aroused by the feeling of someone else shaving him. And if this was just his face, this was going to be the longest shower he had ever had. Literally and figuratively.
She grabbed his arm and raised it to get rid of the arm pit hair, asking, "Is that really all you know? Please just tell me everything."
He shook his head in frustration at what his dad was doing to their Family. "I know they haven't had sex in over five years."
April froze. "Five? I didn't know it was that long."
"One night when we were both friends, Fria's dad had an accident, and she had to take him to the hospital, so I came home early. Our parents were supposed to be on a date or something, but they weren't, and they didn't hear me come in. They were arguing about it, saying it had been since our last family vacation with the four of us to the Cascade Studios Theme Park since they had sex last. I remember that being around my 13th birthday."
April shook her head in frustration as well, glaring at Alex's arms and their father. Sighing, she barely whispered above the sound of the shower. "Do you know about the other thing?"
Alex closed his eyes, sighed heavily, and nodded.
Their dad had been having an affair with another married woman.
Then April asked a question Alex had not dared think about until this moment. "How many affairs do you know about?"
Alex balked at her question. "There's more than one?"
April nodded. "I think there were three. The first one happened four years ago. I caught him with her. That's how mom found out. When Mom found out about the affair last year from a friend she hadn't seen in a while, she confronted him about it. But it was so long ago that he was having another one and he let slip about the one he was currently having. You remember when Mom took us to live with her parents for three days?"
Alex nodded. "I also know dad has been sleeping on the camping cot in the bedroom to keep up appearances. They never used to lock their bedroom at night until the past month."
"I wondered how she let him sleep with her. I have a feeling this is the last weekend that we will be together as a full family."
Alex grabbed her hand from shaving his other arm. "April, we will always be family no matter what. I love you and I love Mom. To be honest, I have begun to hate dad since he didn't show up to my birthday dinner last year because he was busy doing who-knows-what. But you, me, and mom will still have each other. And we also have our grandparents. We'll be fine. I don't think I want to see our dad after this is done. He doesn't deserve us."
April nodded to him in a sorrowful look and continued to shave him. His distraction had been working up to the point she first applied the shaving cream to his legs, causing him to shiver.
"Sorry, is it cold?"
"No. Just hurry."
She looked up at him in confusion until her eyes widened. Then she rapidly spread the cream over his legs. She changed to a new subject, asking, "Have you noticed anything strange about our grandparents?"
"Like what?"
"Like how they never talk about any jobs they have had, and how they seem to have retired well before 60."
"That is a little weird. I did ask grandpa what he did once when we went fishing, and he said he worked as a realtor for major businesses. Helping sell and buy all kinds of buildings and houses across the country. I think he mentioned some of his clients were rich. Maybe the job paid well. He still does go on some business trips. Maybe he just keeps selling for millionaires or celebrities or something like that. He just can't really talk about it."
"That makes sense. And I heard Grandma mention she worked at a medical science lab once. It's just odd they don't talk about it."
"I agree."
April paused her leg shaving in thought. She was currently kneeling on the floor of the shower, which put her awfully close to Alex's trapped manhood. The look of her like that with the water running around her wasn't helping things.
"What's wrong?" He asked while turning to look at a mistake in the tiled wall to avoid her.
"I'm just trying to come up with another topic to keep you busy." She smirked up at him. "Do you have a crush on Whitney?"
He turned back to her startled, "What?!"
April smiled brightly. "Your face tells me you do. She told me once that she thinks you aren't a very attractive guy. She has no interest in you."
Alex felt his heart sink to the bottom of the shower with the water that dripped off of him. "She really said that?"
April smiled apologetically, shrugging. "I think you look fine, but she wants a bigger, stronger guy. No offense, but that isn't you. You are tall and handsome, but you are way too skinny and also way too kind to be the guy she'd be interested in. She likes bad boys. Whitney is nerdy enough for the relationship she wants and doesn't think you and her would be a good fit."
Alex felt like he had been slapped in the face by his own sister and what she was telling him. His voice was even quieter as he croaked, "Really?"
April continued to shave him as she continued. "Yep. Plus, do you really think she would want to be with you when she sees how feminine you look after this? Crossdressing in front of her probably guarantees she will never be attracted to you."
Alex hadn't truly regretted agreeing to do this until this point. Right now, he didn't really want to do anything with either of them. He felt really hurt by what his sister had told him and confused as to why she was breaking his heart like this.
She could have let him down easily, but she kept kicking him while he was already defeated.
His sister was finishing up his other leg when she looked up and saw how sad he was. "Hey, it's okay. I'm sure there is a girl out there that would love to see you crossdress. Whitney is just not that person." After a moment, she asked, "So did you and Fria ever do it?"
"Do what?" Alex snapped at her.
He was really angry at his sister right now. She had just dropped the bomb that he didn't have a chance with her friend and his crush and now she was bringing up his horrible ex-girlfriend.
Then he realized what April had asked. "No. I think we were going to go once, but not really."
"I'm sorry. Have you ever..."
He grunted angrily before he shook his head.
She nodded slowly and tried to reassure him. "Well, I'm sure someone will. Just be patient."
They were silent for a few moments until Alex could calm down, realizing it wasn't really his sister's fault Whitney didn't like him and that it was best he knew now before he did something to make a fool of himself.
Out of curiosity, he asked, "Have you?"
As April finished shaving him, she stood up to glare at him. "Did you just ask your own sister if I had sex? Really?!"
He backed away, his anger turning to fear as he nearly slipped in the shower. "I'm sorry, you asked me so-"
To his surprise, April started laughing. "I'm just teasing you. I don't really care. I have, but I won't ever tell you who."
"It was Tommy Bernard wasn't it."
The look on her face told him everything.
She grabbed the shower sprayer and hosed him down as he watched all of his hair go down the drain.
Staring at his swimsuit covered chest, she frowned before she grabbed the straps of the swimsuit on his shoulders.
"Hey! What gives!"
"I need to make sure your chest is hairless too. I don't need to see you naked, just calm down."
She slid the swimsuit to his waist and began applying shaving cream to his chest. It took all his self-control not to shiver as she rubbed near his nipples.
Then she gently shaved what hair he had on his chest and abdomen.
"There." April said finally.
He was now mostly hairless from the neck down, except for his pubic hair hidden in the swimsuit.
She smiled awkwardly again. "Just one more thing."
April grabbed a bottle then quickly rubbed it over every area she just shaved. She tried to hurry, but the feeling of her hands sliding across his body was starting to arouse him.
When she froze once he looked down to see her staring at the mound his tucked manhood was making while trying to go erect. With the straps off, the swimsuit wasn't as tight down there, so there wasn't much keeping his firm manhood in place.
Then Alex noticed that April's nipples were clearly poking through the wet swimsuit.
She caught him staring and their eyes met in equal shame with both of their faces turning red. Alex quickly stared at the ceiling while April moved faster to smear the lotion on him.
Both silently agreed to never speak of this to anyone.
____
Alex was using her spare towel to dry off, while she did the same. Both of their backs were to each other with the swimsuits still on.
Trying to get their minds off the awkwardness in the shower, he asked her, "Am I really dressing as a girl all day?"
"Yes, you are, for the next two days. Just don't overthink it and try to enjoy it. This may be the only chance you have to do this. Unless you start crossdressing more often."
"I don't know about that."
"Well, we'll see. I need to go grab two things real quick. Don't move."
He rolled his eyes and continued to dry off as she opened the door so they could hear Whitney singing with earbuds in. April came back with a pair of packaged green panties and a pair of blue workout shorts.
He stared at them as she handed them to him. "Really?"
"Yes. For now. Just until we feminize your body a bit. Just tuck yourself in again and these tight clothes should be fine. Also, come out in my robe."
He glanced at the pink bathrobe with a look of disgust as April grabbed her towel and hair dryer. She was shutting the door when she said. "Alex, I wanted you to know I'm happy you are doing this with me. This is going to be a lot of fun, and I can't help but notice how excited you are."
He replied in a whisper so Whitney wouldn't hear, "Thanks for doing this for me April. And not telling anyone about this."
"Of course, little bro." She was about to close the door when she stopped. "Oh, one more thing."
He stared at her expectantly.
She whispered to him with a devious look on her face. "Don't you dare mention this, but I lied about Whitney. She thinks you are really cute and told me that the thought of turning you into a girl was turning her on."
April closed the door in time to block the towel Alex threw at her head.
____
Alex tried not to think about the way Whitney kept smirking at him with April's admission as the girls made him up.
It felt weird to be wearing makeup on his face, and his eyelashes felt very heavy from the mascara they had applied to them.
He was sitting with one knee crossed over the other and his hand on his lap on April's vanity swivel chair. He had been reprimanded for sitting like a guy in the robe he wore, and was forced to sit like a girl, which partially squeezed his tucked manhood.
He had his back to April's vanity mirror that was in her room, so he couldn't see what he looked like. The girls were gossiping about one of their friends named Ruby as they made him look like a girl.
Whitney shook her head. "I thought she wanted to go to some college in California."
"She did, but then she met a guy."
"Is it Nick?"
"No, that was the guy she was with last month. This guy was named Elliot."
Alex asked, "Elliot Lynch?"
Both girls froze to look at him with a strange look on their faces.
He shrank under their gazes. "I know his little brother. I heard Elliot mention a girl he liked named Ruby."
Their expressions didn't change.
"What?" He asked nervously, realizing he had just participated in girl gossip for the first time in his life.
April said, "I think it is that guy, but that's not important now."
"We really need to work on your voice." Whitney informed him.
"Oh." He said shyly. Then he cleared his throat and tried a higher voice. "Is this better?"
Shaking her head, April said, "No you are forcing it too much."
He tried again, lowering it slightly but still keeping it high. "Is this better?"
April shook her head again then said, "Here I have an idea."
She grabbed her phone and turned on her speaker. Cerys Brookes started to play.
Alex spoke in disgust, "Really? You know I don't like her pop music."
Smiling brightly, April said, "Yep. But the music is so popular that I bet you know these songs by heart. I want you to sing along and try to raise your voice to sound like her. We'll give you tips until you sound better."
He glanced over to Whitney who was mouthing the words and bobbing her head. He tried to complain. "But-"
"No buts Little brother... Or should I say little sister." April's smile widened more. "If you want to be convincing, you need to sound like a girl as much as possible. I read somewhere that trans people do this to help their voice. You promised to try your best, so the only thing that should be coming from your mouth is a girl's voice singing 'There's a guy out there for every girl'."
He sighed angrily and said, "Fine. But please not this song."
April glared at him until he started mumbling along, trying to match Cerys's voice.
"Louder." His sister demanded. "Really go for it. You were in choir once so you should know how to sing, now do it."
He rolled his eyes before he really tried to sing. Whitney and April continued giving him pointers as he did so, while they finished making him up. The only break he got was when they needed to put lipstick on him.
After they were done, April had him close his eyes and keep singing while she applied and styled a wig on his head.
His voice was coming along after the fifth song when April paused the music.
April still wanted his eyes closed when she said, "Now we just need a new name."
Whitney suggested, "How about Alexis? She looks like an Alexis."
"I like that, but I think I prefer Lexi. How about its little sister?"
He knew they wanted him to use his girl voice, so he said, "That actually sounds nice."
"Wow, I'm impressed." Whitney commented, patting Alex on the shoulder.
He felt two sets of hands help him out of the chair and he was turned around to face the mirror.
April spoke from his left, "Alright Lexi. Meet the new you. Open your eyes."
Alex opened them, then gasped at the girl between Whitney and April.
Instead of the blonde girl that looked a lot like him that he was expecting, he saw an unbelievably cute red-haired girl standing in his sister's pink bathrobe.
She had thin dark red eyebrows from where April had glued Alex's down, hid them with makeup, and used an eyebrow pen to put new ones on him. The girl in the mirror's eyes were done with cute wing tips, and her lashes looked really cute over her grey-blue eyes. Her lips were a subtle red, and her cheeks were blushing twice over. Once from the light blush his sister had applied, and once from his embarrassment at how attractive he found the girl.
April's thick robe covered her chest, so it was hard to tell she didn't have a chest, but her long legs that came from the mid-thigh length robe looked very smooth and feminine in the mirror.
Alex really did look like a girl. Maybe even April's twin when she wore heavier make up like this.
April couldn't stop smiling. "Well, what do you think?" She leaned in to quietly add, "Remember to use your girl voice."
Alex cleared his throat and gave it his best. "I look like a girl."
Whitney teased. "You are a girl Lexi, what are you talking about? Don't you think you look hot? I definitely do. Girl, you could get any man you want looking like this."
The girl's face in the mirror flushed and developed a look of disgust. Alex saw April give Whitney a glare.
Speaking sarcastically, Whitney said, "Oh, you must not be into guys then. I guess that makes you a lesbian."
April's glare deepened into near fury, as Alex thought about the girl in the mirror kissing Whitney.
April brought him out of the daydream by saying, "Let's keep going. We have big plans today."
Alex looked at her and dropped his voice in startlement. "What plans?"
Whitney punched him lightly in the shoulder. "Lexi, why are you trying to sound like a guy?" She lowered her voice to mock him, "'What plans?' Come on, I thought you agreed to a girl's weekend with us. That means shopping, trying on cute clothes, and looking for hot guys. Or in your case cute girls."
So, he wouldn't get punched again, he complained in his girl voice. "I have to go out like this?"
Whitney and April looked at each other and smiled before turning to him and spoke at the same time, "Duh!"
"But-"
April interrupted his complaint, "Do you think you look like a girl?"
He glanced at the cute girl in the mirror again and slowly nodded.
"Well, you said you would only go out if you looked like one, and I agree with Whitney. I think you look ridiculously hot. Since we already look like twins now, we could play it like that. You are my younger twin sister by four minutes instead of four years. No one will recognize you as Alex, and we won't say anything to anyone to give you away. Right Whit?"
"Nope. We will treat you like a girl the whole time. This just stays between us girls. We are all just BFFs."
Both of them hugged him like they would group hug a friend.
April gave him a smirk as they released him. "Wow, Lexi. I see I got all the boobs. We need to fix that."
She undid the robe on Alex and slid it from his body. He stood there awkwardly while they began prepping what looked like some kind of raw chicken breasts.
"What-" he stopped and cleared his throat after Whitney glanced at him suspiciously as he had used his normal voice. He tried again with his feminine one, speaking softly and shyly. "What are those?"
Appeased, Whitney smiled and said, "They help girls with small chests push them up. Or for women who want to wear a bra with a more revealing dress. They normally have adhesive on one side and are made from silicone. These will be a little different because we ordered them without the adhesive. We are going to glue them to your small breasts to give them a lift."
Remembering to use the girl's voice he exclaimed, "Glue?!"
As she cleaned his chest with an alcohol wipe, April explained, "It's medical adhesive. It'll come right off with the solvent. The adhesive is waterproof and sweatproof."
"Why does it need that kind of adhesive?" Alex asked as he watched a second pair come out with weird tabs on the ends.
Waving a hand over his chest to try and dry the alcohol faster, April asked, "Do you want to lose a boob when we are out in public?"
"No."
"Then there you go. You put on that new deodorant, right?"
He had almost forgotten earlier but had done it right before putting the robe on. "Yes, I did."
"Good. Let's apply the first set."
"Why do I need two sets?" He asked as he watched April apply glue to the first one and press it over his nipple, holding it there.
"Well honey, you are very flat for a girl. I'm just trying to help you out. And we are actually doing three sets." April gave him a big grin. "I want you a little bigger than me."
It took all his self-control not to look at her chest in the tight t-shirt she had put on again after changing out of her swimsuit.
He instead focused on her hands on his chest as she released him. One side of his chest now felt like something was hanging from it. Another one was attached to the other side, then the next larger set with the tab was applied directly over them, completely hiding them.
When the girls went to grab something, he placed his hands over the new enhancers, cupping them and feeling their weight while he enjoyed the sensation of how they pulled on his chest.
Alex released them very quickly as Whitney asked, "Having fun?"
Both girls giggled at him as he felt embarrassed.
April attached the tabs together which lifted up his skin to give him a slight cleavage, making him look more like a girl as he stared at his own chest. Then she showed him how women do their Bras, wrapping it around their body, and doing the hooks in front before turning it around and slipping his arms in the straps.
She added the last set of breast enhancers without the glue, pushing his chest up even further, and situated the bra around his new boobs.
Alex looked in the mirror. He now looked completely like a girl. The wide bra perfectly covered the enhancers, and his cleavage looked pretty realistic. He was a slim girl, and he was definitely more endowed than April was. Though he was not as endowed as Whitney who had a pleasingly curvy figure.
He kind of wished his hips and butt were bigger and his waist was narrower to complete the perfect female image.
As if reading his mind, his sister slid a corset around him.
"Hold on!" He tried to object, filled with trepidation.
April continued to put it around him and did up the hooks in the front of the mesh and skin colored corset that sat below his new breasts. "We need to get you the best possible figure if you want to do this properly. The Acrobat is a very curvy girl. It'll be fine. It's from when I was in 'My Fair Lady' and I needed to be in such a tight dress. Now breathe in and hold it."
"Shouldn't I breathe out?"
"It's a trick I used when they tied it on me. If you breathe out, it gets tighter. We will have to do that tomorrow. But for today, I thought you could just get used to it."
"Fine." He took a deep breath, and April pulled the ties of the corset around him tightly.
Surprisingly, it didn't hurt to breathe as much as he thought it would. He turned and looked at the much narrower waist he now had.
April put her hands over his waist to check how thin he was. "We'll keep going tighter as the day progresses so you can be ready for tomorrow."
He used his new girl voice to sarcastically say, "Great. Something to look forward to."
April smiled devilishly. "I bet Whitney, and I could get it really tight working together right now if you want."
Alex backed away from her. "No, this is fine. What's next?"
"A little eager, aren't we?" Whitney raised her eyebrows as she handed him a pair of heavy black boy shorts.
He felt that they had something similar inside of them to what was put on his chest. "What are these for?"
Whitney frowned at him. "Don't you like girls with big butt's and hips?"
Alex swallowed and nodded.
"Good, then put them on girlfriend."
'I wish I was your girlfriend' Alex thought as he was about to slide them over his legs.
Then he realized where his mind had gone. The thought of him pretending to be a girlfriend to Whitney was actually a very pleasing one.
April sighed. "No, they can't go on over your shorts. Here."
She handed him a lime green tank top, a weird skin colored piece and a pair of really short black Jean shorts. "Put these on in your own bedroom. The beige piece is to go over- 'carefully' over your head to hide the corset under the top. Don't you dare ruin your hair and makeup. Whitney and I need to get changed anyway, then we'll go out for some lunch."
"I really have to go out?"
"Yep. And if you do a good job and act like a girl the whole time without complaining, I'll take you to that decent Italian place for dinner."
"The Vineyard Road, Italian Restaurant?"
"That's the one."
Alex was excited until he realized two things. One was that he had no idea how to act like a girl. Two was that he would probably go to the restaurant as a girl.
He decided that the first problem was more urgent as he said, "I don't know how to act like a girl. I barely look like one and sound like one."
"We'll teach you how, now go." April practically pushed him out of her room and shut the door behind him, locking it.
Before he left, he shouted through her door, "I have to use the bathroom too."
"Fine. Just don't ruin our hard work. Maybe practice acting like a girl in the mirror a bit too. I expect a cute girly sister when you come back. Take your time, I need to do my makeup."
Alex sighed and went to his bathroom. He locked the door and stared at the cute redhead in the mirror.
He watched as the girl smiled at him brightly and sexily slid down the workout shorts, shaking her narrow hips in a semi-strip tease. He watched her grab the black padded boy shorts and slid them up, pulling them to her corset covered waist. She carefully pulled the beige tube waist trainer over her red hair and pulled it over her corset. Then she put the tank top over her large breasts and slid it until it sat tightly on her feminine figure. She adjusted the thin straps of her bra, lifting her cleavage that showed, before adjusting the spaghetti straps of the top. Finally, she slid the black jean shorts up her waist and did them up over her mound, admiring how tight they were on her and lifted her enhanced butt.
The girl in the mirror frowned in thought, an unbelievably cute look on her, then she brushed her hair back and gave Alex a sexy smile with her red lips, blowing him a kiss with her hand on her hip.
Then she giggled.
There was no way that was him.
She looked way hotter than he did and had such a pleasing and feminine figure and features. She was perfect. No one would ever think it was him unless they knew his sister and knew she didn't have a twin.
Lexi was way too cute.
She stared at him for a long moment, their minds, and expressions equal in strong arousal before she swallowed and quickly knelt to the ground.
Alex went under the sink cabinet and reached up to pull a comic book hidden in a corner from under the sink. The Title said it was 'The Acrobat and The Temptress', but the fan made comic book cover was a different art style from the original design.
It was definitely not like the normal comic series as both of the normally straight women were kissing each other passionately and both were showing their underwear in their partially removed costumes.
Alex had gotten this fake sex comic from one of his friends in high school who had a cousin that made these. Alex hadn't pulled it out in a couple months, but the thought of looking like the girl on the cover renewed his interest in the two women.
As he flipped through it, for the first time ever he didn't think he was watching the sexual encounter unfold. Instead, he imagined himself as The Acrobat and he imagined that the things the dark-skinned Temptress was doing were things that she was doing to him as a woman. Things like playing with the nipples on his very own breasts.
Then thoughts of Whitney came to him, and he imagined his crush dressed up like The Temptress.
His triple layer covered groin became very tight, having already strained itself greatly by the arousal Alex had been feeling for the past few hours.
It had been a while since he had masturbated, and he knew if he didn't have release, he would be in trouble for the rest of the day from the intense pleasure he received by having finally turned into the closest proximity to a woman he could imagine.
He opened the toilet seat and undid the shorts, sliding everything down so his semi-erection broke free. It didn't take long for it to go to its six-and-a-half inches. A length Alex was quite proud of, having read online that that was slightly above average.
He went back under the sink and stood to watch the girl apply some petroleum jelly with one hand to her slightly hairy dick.
The sight of it confused him. He was somehow aroused at thinking about the girl having a dick but wasn't excited just by looking at the penis. The more he imagined it was actually a strap-on that was meant for him, the more aroused he became, his dick now painfully erect and throbbing.
He had never desired to be penetrated before.
Never once did he think he would want a girl to peg him in his put with a strap on. Or even with some kind of dildo as she pressed her bare chest in his back and whispered things of pleasure in his ear. Maybe she had even forced him into her clothes and wanted to play with his fake breasts while she sounded a dildo into him.
Alex surprised himself by letting out his first sexual moan.
He had never felt this aroused in his entire life as a girl openly stared at him with a suggestive grin on her face.
On his own, made-up, and unbelievably beautiful face.
Taking the comic in his clean hand, Alex set it on the counter next to him as he sat on the toilet, stroking himself softly.
He picked up speed and strength as he flipped through the pages, continuing to imagine himself as Maggie McCain, The Acrobat in the comic. It took him no time at all to get to the scene of her scissoring Vea Chandice, The Temptress, both their sexy costumes forgotten.
Alex thought of his dick hidden between their folds while he was The Acrobat and Whitney was The Temptress, causing him to climax hard into the toilet with a heavy gasp.
After he recovered, he realized that was probably the fastest he had ever come to an orgasm and one of the best he had ever had.
And if that was the case, he knew that he would have to do this again more often, just so he could feel the rush of wearing women's clothes again and the pleasure of masturbating in them.
Alex also wondered just how he was going to control himself for the next two days as a girl, while feeling extremely excited at what was to come and what his sister and his Crush had planned for him tomorrow.
Tomorrow was going to be amazing, though he still had a long day ahead of him today.
____
____
"Dear Reader,
Thanks for reading Alex's first time crossdressing. I hope you enjoy it as much as I enjoyed making it. I put a lot of thought into all my work, and hope you find this one special.
My next story (if it's out) will always be posted in the description.
If you did like this one, I would really appreciate it if you could Star or Comment below, even if it's just a simple ❤ ️ or 👍. If you have suggestions, or something I missed, tell me that too. I read all my comments and appreciate the tips as a new writer.
Until next time,
-Xarek"