The Story Behind This Sissy Story

Guess what kinksters! I’ve got another erotic audio for you. This time it is a sissy story! (If you were hoping this post was going to be a continuation of our cuckold sex story from last month, don’t worry. I haven’t abandoned it. I actually have something excited planned that is going to take a little extra back end work but it is coming soon!). The cool thing about this sissy story is that the details of the story; from the genre, the scenario, the tone, to smaller ones, like our protagonist’s hair color were all voted on by the community members of Enchantrix Empire!

Enchantrix Empire is LDW’s own kink focused social networking site! It’s a fun place to kick back and hang out with Mistresses and other kinksters. It is seriously a lot of fun over there. We share music and memes. We post sexy pics and gifs! We talk both kink and vanilla interests! Ms. Rachel posted the sexiest fucking tease pic in the prejac loser humiliation group the other day that had me…questioning…things… Ms. Riley made the EE hive mind come together for some seriously hilarious kinky madlibs! For fans of horror novels, Ms. Fiona runs the scream queens book club that is worth popping into when looking for a new read. For my domestic servants, sissy housewives, and cuckies who take care of things at home while wifey is out fucking, Ms. Harper shared a texas chilli recipe a while back that was *chef’s kiss* and is sure to please the lady in your life.

I think one of my favorite things about EE is what a supportive community it is! Exploring the kinky side of life can be a bit of a roller coaster. As fun and thrilling as it can be, sometimes it is just hard to be so different. If you need a little encouragement or to get some things off your chest, there are a lot of understanding ears over there. And boobs. We post a *ton* of boob pics.

Thank You to the Enchantrix Empire Community

Before we get on with our sissy story, I would like to extend my thanks to all the members of the EE community for taking the time to vote on the polls and their contributions to this project. Truth be told, this was not the audio that I would have created without your input. Actually NONE of the options I voted for ended up winning! (RIP Randy the panty stealer). I really had fun working on this and I am looking forward to doing another round of polls for part 2!

Enough mushy ramblings. Grab some lube, put on your favorite panties and enjoy a sissy bridesmaid story! The text for our sissy story is found below, and the audio version can be listened to by clicking the media bar at the bottom of this post. Audio length is approximately 20 minutes.

The Sissy Bridesmaid – Written by Enchantrix Empire

Chris arrived home after a long day at work, eager to see his lovely girlfriend, Sarah, but upon entering their shared apartment Chris was flummoxed to hear the sounds of a woman crying. “Sarah? Is everything alright?” Chris called out as he followed the sound to the living room.

Sarah sat on the couch, her long blonde hair cascading in perfect waves around her shoulders.  Chris was relieved to see that she was not the one who was upset. Instead it was Sarah’s best friend, Amanda, who was sobbing. Sarah looked up, her eyes filled with concern as she saw Chris enter the room. “Hey babe,” she said softly, her voice filled with worry. “Amanda has a wedding crisis

Chris raised an eyebrow, curious about the situation. “What’s the problem?” he asked. Amanda, Sarah’s best friend, was getting married this upcoming weekend. Chris had been looking forward to attending the wedding, in part due to the open bar, and also because Sarah’s role as maid of honor would finally be coming to an end.  Chris loved his girlfriend more than anything, but he couldn’t wait for the second hand wedding stress to finally be over.

“Apparently,” Sarah explained, “One of the bridesmaids dropped out last minute. Mandy’s in a complete panic, and we’re trying to find a replacement.”

“Weddings can be stressful,” Chris murmured, “but I’m sure everything will work out.”

“How can you say that?” Amanda shouted, her voice echoing through the apartment. “We’ve called every woman Sarah and I know, and no one is available! I’ve spent two years planning this wedding, it was going to be perfect and now everything is ruined!”

Chris felt a pang of guilt as he watched Amanda’s face contort in anger. He knew that he needed to do something to help, but he was unsure on what it was he could do. He had never been much of a planner, and the thought of being put on the spot to come up with a solution to such a big problem made him feel uneasy.

“Well,” he began tentatively, “I don’t know many women who could step in at the last minute, but maybe I could ask around work tomorrow?”

Sarah gave him a small smile. “That’s sweet, Chris” she said “But we really need someone by tonight. The rehearsal dinner is in a couple hours and if we don’t have someone by then…”

“I’m fucked.” Amanda chimed in.

“But what if we think outside the box?” Sarah suggested to Amanda with a glimmer of hope. “What about your brother? I know he was supposed to be an usher, but I’m sure we can make do with one less. He already has a tux.”

“No, that won’t work,” Amanda replied, shaking her head. “My future in-laws are so traditional that they would flip out if there was a man in the bridal party. That’s the last thing I need to deal with.”
Amanda sighed, her frustration making her voice crack.

Chris couldn’t help but chuckle at the absurdity of the situation. “Well,” he said, trying to lighten the mood, “what if we put your brother in a dress?”

Sarah and Amanda burst into laughter at the image of Amanda’s burly brother in a frilly dress. Amanda, however, quickly composed herself and rolled her eyes at Chris. “Yeah, sure,” she retorted. “We’ll just stuff my six-foot, four-inch tall, 250lb hairier-than-bigfoot, brother into a dress. That’ll fool my in-laws!”

“Alright, alright,” he conceded, holding up his hands in surrender. “I guess that’s not the best idea. But I’m sure we can come up with something.”

Sarah’s eyes suddenly lit up with excitement. “Chris, I think you might be onto something!” she exclaimed, clutching his arm enthusiastically. She turned to Amanda and said “What if we actually pass a man off as a bridesmaid? Sure, your brother would look like sasquatch in a slip, but what if we found a shorter guy with a smaller frame?”

Amanda pondered the idea, her expression shifting from skepticism to cautious optimism. “Who do you think would be able to pull that off?” she asked, her voice betraying a hint of desperation.

“Well, what about Chris?” Sarah suggested.

Chris couldn’t believe what he was hearing. “Me?!” he exclaimed. “There’s no way I could pass as a bridesmaid!”

Sarah shook her head, her eyes shining with determination. “Nonsense,” she retorted. “You’re the perfect height, and your frame is quite small. Plus, your face is pretty feminine for a man.”

“I highly doubt that,” Chris muttered, feeling self-conscious.

“Oh, come on,” Sarah insisted. “I’ve seen guys with less feminine features than you pass as women before.”

“And where exactly did you see this?” Chris asked with a slight air of accusation.

“Tik tok” Sarah replied waving her hand. “What do you think Amanda?” Sarah asked, turning her gaze back to her best friend.

Amanda bit her lip, considering the possibility. “Well,” she started, “It certainly wouldn’t hurt to try.”

Chris hesitated, his heart pounding in his chest. He knew that he had a slender build for a man, but passing as a woman was a completely different matter. However, the thought of helping Sarah and Amanda, especially in their time of need, made him reconsider. “Alright,” he finally agreed, “Let’s give it a shot.”

Sarah clapped her hands excitedly. “Great!” she exclaimed. “I’ll go get our supplies.”

As Sarah disappeared into the bedroom, Chris couldn’t help but feel a mix of excitement and apprehension. He had never cross-dressed before, and the thought of doing so in front of Amanda and Sarah was both thrilling and terrifying. The three of them gathered around the coffee table, where Sarah began to lay out the “supplies” to transform her boyfriend into a bridesmaid.  Chris stood awkwardly, staring down at the array of makeup, clothes, and accessories spread across the surface, stuffed into bags and spilling onto the floor.  He felt a strange tension building within him, a mixture of anticipation and anxiety, as he awaited his transformation.

Sarah smiled encouragingly, her eyes sparkling with excitement. “Alright,” she said, “Our first order of business is to get you into a proper outfit.” She reached into a large bag and pulled out a pair of purple lace panties and a matching bra. Chris’s heart raced as he took the delicate lingerie in his hands, the soft fabric feeling foreign and exhilarating. “Let’s start with these,” Sarah instructed, her voice softening. “Go ahead and change in the bathroom.”

Chris hesitated briefly, his pulse quickening as he contemplated the task ahead. Gathering his courage, he silently nodded and headed towards the bathroom, leaving the door slightly ajar.
As he stepped into the bathroom, Chris felt a rush of excitement course through his veins. The prospect of donning women’s lingerie ignited a spark within him, a forbidden desire that he had never allowed himself to explore. He stripped down and took a deep breath as he stepped into panties for the first time.  As he slid the panties up his legs, he couldn’t help but glance down at his crotch, the sight of his penis nestled between the lacy fabric causing a wave of arousal to wash over him. Chris quickly pulled the panties up and secured them tightly around his waist, his heart pounding in his chest. He then gingerly reached for the matching bra, his fingers trembling as he adjusted the straps and cups to fit his smaller bust. As he fastened the bra, Chris couldn’t help but admire the way the lace hugged his chest, creating a surprisingly feminine silhouette.
Chris emerged from the bathroom, his heart pounding in his chest.

Amanda and Sarah’s eyes widened as they took in the sight of him, now adorned in women’s lingerie. Sarah could not resist teasing him, her tone laced with playful sarcasm. “Well, Chris,” she began, feigning astonishment, “I didn’t realize you had such a penchant for lingerie.”

Chris blushed furiously, his face flushing a deep shade of crimson. He attempted to deflect her teasing, his voice cracking nervously. “I… I’m just doing this to help you out,” he stammered, his gaze darting between the two women.

Sarah laughed.  “I’m sure you are,” she replied, her eyes twinkling mischievously. “But I can’t help but wonder what else you enjoy wearing.” Chris blushed even deeper, his heart pounding in his chest. He knew that he was enjoying this strange game of dress-up, but the thought of admitting it to Sarah and Amanda terrified him. As he struggled to compose himself, Sarah approached him, her eyes gleaming. She handed Chris a pair of high-heeled shoes and Chris’s heart raced as he gazed at the sleek, white stilettos.  “Now,” Sarah purred “Let’s see if you can manage to walk in these.”

Chris eyed the towering heels warily, the fear of falling and embarrassing himself threatening to consume him. He swallowed hard, his Adam’s apple bobbing nervously as he accepted the challenge. With a deep breath, he carefully slipped his foot into the shoe, wincing as he felt the cold leather wrap snugly around his ankle. He carefully placed his full weight on the heel, wobbling precariously for a moment before regaining his balance. His pulse throbbed in his throat, his breathing shallow as he steadied himself and took a lap around the room

Amanda tilted her head, appraising him critically. “Well, you seem to be doing alright so far.” Amanda’s voice held a hint of admiration, despite her initial skepticism. “Now, let’s see what you look like in this.” She said, handing Chris a layered floral print dress with a ruched bust. His heart raced with a mixture of excitement and trepidation as he slipped the dress over his head, the soft fabric brushing against his skin, causing a shiver of pleasure to ripple through him. As he adjusted the dress, the ruffles and layers creating a whimsical silhouette, Chris could feel his cock starting to stir. He shifted uncomfortably, attempting to hide his growing erection.

“Alright,” Sarah announced, her excitement palpable, “Hair and makeup time!” She held up a long red wig and her makeup kit. Chris’s heart raced at the thought of being transformed further, his cock twitching in his panties. Sarah and Amanda exchanged a knowing glance, their amusement evident in their gleaming eyes. They seemed to be savoring the situation. They began to carefully apply makeup to Chris’s face, using foundation, concealer, and powder to create a flawless complexion. Next, Sarah applied long, soft, false eyelashes and gave them a slight curl. “So, Amanda,” Sarah said, dabbing some shimmery eye shadow onto Chris’s eyelid, “What do you think of our doe eyed little bridesmaid to be?”

Amanda scrutinized Chris’s face, her eyes dancing with amusement. “She’s looking very pretty,” she replied, her voice laced with a hint of teasing. “I think she needs a bit of pink lip gloss.”

Chris’s heart fluttered at being called “she,” the term carrying a strange sense of euphoria mixed with embarrassment. Before he could protest, Sarah chimed in, “Yeah, I think you’re right. She definitely needs some shine and color on those lips.” With practiced precision, Sarah applied a thin layer of pink lip gloss to Chris’s lips, the warm sensation of her touch sending a jolt of electricity straight to his core. He could feel his cock beginning to leak into his panties. With the makeup complete, Sarah and Amanda eagerly helped Chris into the long red wig, securing it with clips and hairpins. They styled the wig in loose romantic waves, accentuating Chris’s femininity. As they admired their handiwork, Sarah and Amanda couldn’t help but tease Chris for looking so pretty. They giggled and complimented him, their words tinged with a hint of flirtation.

“Wow, Chris,” Sarah cooed, “you’re almost too pretty to be a bridesmaid.”

Amanda couldn’t resist joining in on the fun. “Seriously,” she chimed in, giving Chris a playful wink, “Don’t you know the first rule of wedding etiquette is ‘don’t show up the bride’?” Chris could only muster a weak laugh, his cheeks burning with humiliation. Despite his efforts to maintain composure, he couldn’t deny the mounting excitement he felt at being transformed into a bridesmaid. He stole a furtive glance at Amanda, his gaze lingering on her curves and graceful form, like most men, he had always admired the feminine form, but instead of lust, today he felt a twinge of jealousy.  Amanda caught his eye, offering a reassuring smile before turning her attention back to Sarah “Do you think we have time to shave her legs before we have to leave? Or should we just have her put on some hose?” Amanda questioned.

“I’m not sure,” Sarah admitted, her brow furrowing in concentration. “We’re already running late for the rehearsal dinner. We should probably just put some stockings on her. ” 

“Sounds good.” Amanda replied, grabbing a pair of white lace-topped stockings and a garter belt. “Alright,” she said, “Let’s get those stockings on.” 

“Chris,” Sarah urged, her voice softening, “we need to hurry. Can you lift up your skirt so we can help you secure the garter belt?”

Chris swallowed hard as he reluctantly hiked up the skirt of his dress. He was still rock hard and he knew that there was no hiding the ever growing wet spot in his panties. The thought of exposing himself to Amanda and Sarah made him feel incredibly vulnerable. As he revealed his panties and the bulge in his crotch, his cheeks burned with humiliation. Chris knew that Amanda and Sarah could see his erection, his body betraying his secret desires. Amanda gasped, her eyes widening in surprise. “Oh my God!” she exclaimed, her voice filled with astonishment. “Look how excited she is!”

Amanda and Sarah errupted with laughter and Chris felt a wave of embarrassment wash over him, his face flushing a deep shade of crimson. He stammered, desperately trying to deflect their attention. I’m just nervous,” he protested, his voice cracking.

 “No,” Sarah teased. “I think little Chrissy just really REALLY likes being a girl.”

“Is that what you call it?” Amanda snickered, “Chrissy isn’t a bad name though. For a bridesmaid I mean.”

“We better get your stockings on before we lose any more time.” Sarah said composing herself.” “All done!” she chimed after helping Chris with the stockings, then she and Amanda stepped back, admiring their work. 

“Well, How do I look?” Chris asked apprehensively. 

“Come see for yourself!” Sarah exclaimed as she grabbed Chris’s hand and guided him to the full length mirror in their hallway.  “Stand up straight, babygirl,” she whispered in his ear, her breath tickling his neck. “Show us what you’ve got.”

Chris’s heart raced as he gazed at his reflection, his eyes widening in disbelief. His skin glowed with a soft radiance, the makeup accentuating his femininity and creating a captivating allure. The floral print dress hugged his slender frame, the ruched top emphasizing his small bust, while the layers and ruffles created a whimsical silhouette that belied his masculine origins. High-heeled shoes completed the ensemble, adding a touch of elegance and sophistication to his appearance.  The shoes, once a source of trepidation, now felt like natural extensions of his feet, as if he had been wearing them for years. The red wig, with its long, cascading locks, framed his face perfectly softening his masculine angles.

“Well,” Amanda said, her eyes sparkling with admiration, “I think you look absolutely stunning.”

Sarah couldn’t resist teasing him further, her voice thick with affection. “You know, Chrissy,” she purred, reaching out to brush a stray lock of hair away from his face, “I think you’re looking prettier than some of the actual bridesmaids.”

Chris blushed furiously, his heart pounding in his chest. “Stop it,” he protested weakly, his voice quivering “You’re just trying to embarrass me.” Chris grumbled, still unable to tear his gaze away from the mesmerizing reflection before him.

In response, Sarah merely grinned mischievously, her eyes glittering with delight. “Maybe a little,” she confessed, wrapping an arm around Chris’s shoulder. “But seriously, you look fantastic.”

“Thank you,” Chris mumbled, his cheeks still flush with embarrassment. “I just hope I can pull this off.”

“Don’t worry,” Amanda assured him, her voice warm and comforting. “We’ll be right by your side the whole time. And besides, you’re the only one who knows you’re not a real bridesmaid. Everyone else will just think you’re one of the girls.”

“Exactly” Sarah agreed. “Just one of the girls. You’ve got this babe. But we really do need to get going.”

Chris nodded, taking comfort in their words. He took a deep breath, gathering his courage and stepped out into the world as a Chrissy for the first time.