Guildmates Ch. 02

(What is this, a crossover episode? Sorry for the delay and any lacking quality, been super busy. Thanks everyone for reading <3)

After the compelling argument Damon had made the night prior, Asa decided to indulge him and give things a shot. At the very least, the sizeable sum he had been provided was enough to keep him going for a while. He called into work, apologizing profusely for quitting last minute. His supervisor was pissed, going off on a tangent about how unreliable and lazy he was. He hung up the phone mid rant, not eager to subject himself to the barrage of insults and shouting. Instead, he took this time to look to the future. Damon had insisted that he spend some of the money on himself, specifically noting that he should find a cute outfit.

While Asa certainly had no issues wearing women's clothing in the privacy of his own home, he had never even considered buying them in person or wearing them out in public. He found himself in a rather confusing place. He enjoy feeling feminine, and all the things that came with it, but it was not easy to think of himself as a girl even when he wanted to. Even after being treated as a girl for so long, it wasn't so easy as flipping a switch and becoming one. This created a massive disconnect between his external image, his desires, and his self-image. The effects were nauseating, causing his head to pulse unpleasantly.

A quick Google search of his condition to be similar to that of something call Dysphoria. Apparently, it was something transgender individuals experienced due to the difference in sex identity and gender. Though he had never remotely considered himself to be transgender, the information he found online had him down to a T. Asa rubbed his temples in frustration. He should be happy, right? Why wasn't he happy? If anything, he felt even more lost than before he had started questioning his identity. It was so much easier just burying it down deep and living as he was. Either way, there was no going back.

Asa collected his belongings, summoned whatever remnants of courage he possessed, and headed out the door. He found his way to a small clothing outlet a few blocks down. It was a local establishment, and not particularly popular by the looks of it. He peeked in the window curiously. It would have to do. Maybe he could get in and out quickly without any issues. He could just say it was for his girlfriend or something. His girlfriend who just happened to be his size. Asa sighed deeply, collecting his thoughts. He was going to make this work.

Stepping inside, Asa immediately found himself face to face with a salesclerk. "Welcome!" The middle aged woman chirped excitedly, surprised to see him enter. "How can I help you today?"

"I need... Clothes," he murmured timidly, wringing his hands together. Smooth.

The woman arched a brow, regarding him curiously. "Well, this is the place to be then. Are you looking for anything in particular?"

Asa blanched. Though he had a few undergarments in his collection, he knew next to nothing about women's clothing. He had no idea where to start. "D-dress, o-or something?" He croaked nervously.

The clerk looked down at him with a note of pity in her expression. "Sure thing sweetheart. What's your size?"

Asa pursed his lips, panic rising within him. "I-It's for my girlfriend... She's my size, b-but I don't know exactly." His cheeks burned with an intense heat. There was no way the lady was buying any of this.

"Of course, dear," she responded with a soft smile. "I'm sure we can find something. Do you mind if I take your measurements?" The woman paused, before hastily adding, "to get your girlfriend's size of course."

Asa nodded in defeat, too mortified to respond. The woman took his measurements with a tender touch. "Does your girlfriend need underwear as well?"

Asa nodded again; his gaze glued to the floor. The woman placed her hand comfortingly on his shoulder before heading off to procure a pile of clothes for him. He picked through the articles, though he still had no clue what would look good on him. Instead, he decided to just get everything. God knows he had enough disposable income at the moment, and he didn't think Damon would be too upset. They arrive at the counter and the woman began ringing him up. His eyes went wide as he watched the number on the screen climb higher and higher.

"You can take these home and you... She can try them on and return anything that doesn't work." Asa glanced down at a sign on the counter which prohibitively stated no refunds. "I own the place, don't worry about it."

She handed him his card back, placing the receipt in the bag. "T-thank you," he stammered, grateful for her understanding nature.

"Of course. I hope we'll see you back in here again."

All but sprinting from the shop, Asa headed home with his bag of garments. He felt incredibly self-conscious carrying them around, as if someone might recognize the bag and call him out. The idea was outlandish, but he could not help but feel as though prying eyes watched his every move. He arrived back at his apartment safely and began unpacking the contents of his shopping excursion. Asa was glad that woman who helped him find the clothes had a good sense in taste, as he didn't have much himself. Before this afternoon his closet was dominated by monochromatic articles and nondescript denim pants.

Asa began trying on the new clothes. The articles were of a much brighter shade than he was used to, though admiring his image in the mirror he felt that the new look suited him. In those moments dressing up, the crawling creeping dread known as Dysphoria had slowly receded, if only for a while. It was a weight off his shoulders. Looking at himself now, it was much easier to imagine a world where he could accept himself as a girl. As he admired his figure in a short blue floral summer dress, his phone chimed from the table. He scrambled over, scooping it up. As he suspected it was Damon, after all no one else ever called or texted.

'Hey sweetness. You quit that dead-end job yet?'

'My manager wasn't happy.'

'Does that mean I should expect you by today?'

'I suppose so. What is the address? I'll take an Uber over later.'

'Fuck that. I'll pick you up.'

Asa was amenable enough to the idea. He wasn't eager to get in a stranger's car, let alone while crossdressing. Was it even crossdressing anymore?

'Sounds good. I just have to figure out what to wear, but I'm ready whenever.'

'Whatever you're comfortable in. I can't imagine you'll be in it long.'

Blood rushed to his cheeks as Asa read the text. Damon sure had an insatiable appetite, not that he minded. It felt nice to be wanted for once.

'Did you happen to go shopping yet?'

'Yeah... I think I got too much though. I'll have to return some.

'Good girl. We can do that on the way over to mine.'

Asa nervously collected the clothing, separating what fit and what didn't. He tucked away what he decided to keep, though his meager closet could hardly handle the extra contents. For a moment he briefly entertained the idea of living with Damon. It sounded like he was rather well off, and though Asa had never cared much about luxuries or cash, the idea was suddenly appealing. It wasn't long before he heard a knock at the door. He rushed to the peep hole and peered out to find Damon waiting for him. Nervously smoothing the lines of his dress, he opened the door.

Damon's face lit up as he admired Asa, his gaze running up and down his body in an approving manner. He shocked the smaller boy by rushing forwards and pulling him into an embrace. His hand slid down the small of Asa's back and across his rear, giving it a tight squeeze. Damon's hand then deftly slipped beneath the hem of the dress, groping his ass through his new panties with a wide grin. Asa stared up at him with hazy blue eyes, his cheeks burning with embarrassment as he did his best to stifle a small moan

The old man who owned the beaten up little apartment complex passed the couple that stood in the doorway. Asa bit back a yelp of surprise as his sharp eyes settled on him. He withered beneath the man's sneering gaze, turning away in chagrin. Damon noticed the sudden change in behavior and turned to face the landlord. "Fuck off you old creep, this isn't a show," he growled, pulling Asa's waist tight against himself in a protective manner.

"Then why is it happening in my hallway?" The old man jeered in return. "Besides, if I knew the boy was some kind of pervert, I wouldn't have rented him the place."

A fire lit in Damon's eyes as he whipped around, placing himself between the old man and Asa. "Call her a boy again and see what happens crypt keeper," he hissed violently, his hands tightening into fists.

Asa appreciated Damon sticking up for him, no one had ever done that before, but he was already on the verge of tears and didn't want a confrontation. He tugged at Damon's sleeve, drawing his attention away from the furious staring contest. "L-let's just go," he suggested in a desperate tone.

Damon's gaze softened as he realized Asa's emotional state. "Sorry, you're right."

The old man skittered off the moments Damon turned away, but not before shooting Asa a hateful look. The whole experience was a painful reminder of what it would be like to be within the eye of the public. Damon's continued hold on him helped alleviate some of his worries, at the very least. Asa locked up being him and the two headed out. He fidgeted nervously as they walked. He had barely worn so much as a dress in the past, and now he was doing it out in public. He clutched at the hem of the garment anxiously. Damon, sensing his turmoil, slipped an arm around his waist, giving it a small squeeze.

As they arrived outside Asa regarded the vehicle waiting for them with a measure of slack-jawed awe. It was a flashy coupe that Asa suspected cost more than he would've made in even ten years at the bookstore. Just how rich was he? Damon opened the door, escorting him inside before taking his place at the wheel. The two headed off in the direction of the store. On the rather short drive, Asa came to a sudden realization. Namely that after his exaggerated and awkward farce he would be returning to the very clothing store he just left only hours ago, except crossdressing. Of course, the owner almost certainly saw through him, but he was still filled with shame.

Asa hesitated outside the establishment, clutching the bag with shaking hands. Damon crouched down to his eye level, giving him a worried look. "You alright princess? I can do this for you if you'd be more comfortable in the car."

His face flushed bright red at the pet name. Though he most certainly would feel more comfortable avoiding the situation, he felt strangely determined to see things through. He shook his head adamantly and the couple headed inside. The owner was busy with another customer at the counter, so the two took a moment to look around. As they perused the aisles, they heard a voice from behind them. "Can I help you find anything?"

Asa jumped a little in surprise, nervously turning to face the woman. He could hardly maintain eye-contact. Out of his peripheral vision he saw the woman's face light up excitedly as she realized who he was. He could've sworn she seemed almost proud. "R-return..." He stammered helplessly.

Damon pulled him in close. "She's just a little nervous. We've got some stuff to return is all."

"Of course!" The woman chirped with delight. "You look stunning sweetheart," she cooed in an assuring manner, "and such a handsome boyfriend."

Asa averted his gaze, intently studying the floor. Of course, his bright red face and neck gave him away as usual. "Thank you," he responded in little more than a whisper as the woman lead them to the counter.

Asa and Damon stood in waiting as the owner rang up the items for return. Damon looked down at him with a mischievous grin, clearly taking pleasure in his chagrin. To make matters worse, his hand had found its way to Asa's backside once more. He kneaded the flesh, gripping it tightly through the dress. He did his best to muffle a whimper as Damon's fingers teased towards the center. Apparently, his efforts were insufficient, as the woman on the other side of the counter looked up curiously. She blushed heavily as she realized what was going on.

Asa hid his face in his hands with a carnal shame. The owner of the shop, almost as flustered now as he was, quickly refunded the amount and bade them farewell with a nervous stammer. The couple left the shop, Damon continuing to grope his ass the entire way out. He gave Asa a swat to the rear as they exited the doors. Asa, struggling to contain his excitement, squirmed restlessly as he adjusted the front of his dress. He was grateful to return to the privacy of the car, as the evidence of his sexual arousal was becoming rather evident.

Damon returned to the driver's seat, flashing him a wicked smile. He leaned over, kissing at Asa's neck as his hand wandered up the length of his leg. "You sure do like that huh?" He inquired, his fingertips reaching the bulge beneath Asa's dress. "You like it when other people watch."

Asa quivered at his touch. "N-no," he objected weakly.

"You don't do a great job at hiding it," Damon teased, caressing the damp tip of Asa's cock through his panties.

Damon bit down lightly at his neck, eliciting a surprised gasp. Asa's member pulsed in response. "M-maybe a little," he admitted in a meek tone.

Damon rolled down the window down and began unfastening his belt buckle. Asa glanced nervously out of the window. He grasped the implications quickly but was slightly hesitant of a stranger catching him in the act. After Damon's manhood sprang free, however, Asa needed little encouragement. He eyed the slab of meat hungrily and immediately climbed over and got to work. Asa eagerly began running his tongue along the length of the sizeable appendage.

Asa had almost forgotten just how imposing that part of Damon was. The massive member was hot and pulsing in his grasp. Asa stared up at him with hazy doe eyes as he pumped his hands along the length. Damon glanced away briefly, looking out the window. "Can we?" A female voice chimed from behind him excitedly.

Damon gave a nod, and that's when Asa felt a man's hand grip his rear. He jumped slightly in surprise, squirming responsively as he was fondled. Damon ran a finger along Asa's chin, returning his attention to the task at hand.

Asa put his mouth back to work pleasing Damon, taking the tip of him against his tongue. He eased it further into him inch by inch as the stranger felt him up from behind. The backside of his dress was pulled up over his hips as the mysterious individual revealed his panties. The large firm hands worked over his backside exploratively, spreading and squeezing his cheeks as Asa's head bobbed up and down on Damon's cock. His panties were then tugged down, exposing him entirely. The hands receded for a moment, and Asa felt a flash of disappointment as the molestation was interrupted.

The respite was brief, however, as the stranger had only retracted his hand to lubricate a finger with his spit. The man's finger then began to prod at the entrance of him, working its way inside his asshole and sending a shiver up Asa's spine. He let out a lewd moan as the large digit pressed further inside him. He wriggled his backside in delight as the tip of the strangers finger hit that wonderful button inside him and caused his cock to drip with excitement. To his surprise, another hand brushed against the curvature of his rear.

This hand was softer and more delicate, likely belonging to a woman. She toyed with him in tandem with the other stranger as he pleasured Damon. Her hand swiftly struck his rear, causing him to yelp and nearly choke on the member in front of him. He heard a giggle as the woman behind him basked in his humiliation. All of this only served to excited Asa more. His cheeks stung red as she continued to spank his ass, occasionally take a break to give him a squeeze. Her hand then slid further down.

Asa felt disappointment and fear as the woman's hand reflexively retreated as she came in contact with the small and dripping bulge tucked away between his legs. To his surprise, the touch soon returned. The woman giggled ecstatically, clearly excited by her discovery as she grasped his satin clad cock tightly in her grip. Asa let out a high pitched mewl as she flicked her thumb across the tip. His mind was lost in a deep fog at the intense level of stimulation. The feeling of being exposed and assailed while sucking on Damon was beyond his wildest fantasies. Damon's hand went to the back of his head, easing him down further.

Without warning Damon's manhood erupted, sending thick splashes of salty bitter liquid down the length of Asa's throat. He choked it back, his eyes watering at the exertion. He pulled back with a cough, unable to contain the tide of sticky white liquid. Cum dribbled down his lips and chin in long strings. He felt his legs quiver beneath him, threatening to give way as the two strangers behind him continued their molestation. No longer able to hold back his pleasure, nor his voice, Asa cried out as he filled his panties with cum. He shook violently, dousing the strange woman's hand in his ejaculate.

From behind, he heard the man grunt as his companion used Asa's own cum as a lubricant to pleasure him. His finger slipped out from Asa's rear, and he soon felt a wet and warm sensation against his backside as his rear was painted with the stranger's semen. Asa finally collapsed, staring up at Damon with a drained expression. Despite his exhaustion he began to lap up the remaining cum from Damon's lap. "Good girl, but you better take care of our guests first."

Asa turned around, too drunk on endorphins and oxytocin to feel ashamed. The couple stared down at him with broad grins, the man tucking away his member, as he began licking the sticky white fluid the stranger left on the window's ledge. The man was a handsome gentleman somewhere in his mid-forties, with a grey speckled beard and hair. He reached forward, gripping Asa's chin and easing his mouth open gently as he stared groggily up at them. The woman, a much younger individual with short platinum blonde hair, worked her drenched fingers into his mouth. "She's cute," the younger girl remarked with a giggle.

"Yes, she is," the older man agreed with a deep chuckle, tucking a small black business card into the gap of the window.

Asa gladly cleaned her long and slender fingers, which had been drenched in a mixture of the man's and his own cum. He worked his tongue between the digits to get every last drop. He was once again shocked by the woman's surprising initiative as she bent down and locked her lips with his. Her tongue, which he dazedly noticed was split down the middle, prodded into his mouth and swirled against his own in an impressive display of intimate prowess. Asa was left gasping as the woman pulled back, a string of saliva dripping from between their mouths.

The couple departed, the woman flashing Asa a quick wink as they scampered off. Damon reached over and plucked the card from the window as he rolled it up. "Looks like you made some friends Rinko," he noted with an impish expression.

Asa buried his head in his hands as the high of the situation slowly began to wear off. He was flooded with embarrassment and horror, though he had to admit he enjoyed himself. The anonymous couple who participated seemed to enjoy themselves as well. They were an attractive pair. The man was a bit old for his own tastes, but the girl had a certain sultry appeal. He shifted nervously in his seat as he realized how thoroughly stained and sullied, he was. Damon reached out and reassuringly patted his head. "Let's get you back to mine and we can clean you up," he noted softly, leaning forward and kissing his cheek tenderly.