Pleasures Pawn Ch. 02

The morning sun filtered through curtains, casting a warm glow over the sparsely furnished apartment. As the light hit Gabe's eyes, they fluttered open and he slowly woke opened them up more, rubbing them gently. As he slowly regained consciousness yesterday's events rushed back into his mind. He felt so many emotions at once. He was confused, ashamed and grateful all at the same time. He sat up in his warm, albeit makeshift bed. He rubbed his eyes again as he looked around the living room. The second his eyes went over the door, almost as if on cue, it swung open. Aria stretched her arms as she walked out of her room, her hair in a beautiful mess and her eyes a bit swollen as if she didn't get much sleep. As she walked towards the kitchen area, Gabe noted she was only wearing a tight top to hold in her breasts, her massive cock hung between her legs, swaying back and forth freely. Gabe could not keep his eyes off of it, but tried his best not to focus too much on it.

"My eyes are up here you know." Giggled Aria as she crossed by him

"S-sorry" Gabe blushed as he closed his eyes and took a deep breath, sucking in the scent she left behind.

"Hahaha, it's fine! How did you sleep?" Aria asked with a tinge of care and concern.

Gabe looked up at her, still feeling a bit shy but could sense her question being genuine, "It was good. I haven't had a good night's sleep like this before in a while now." Gabe gave a slight smile as he stretched his arms as well.

"Good!" Aria smiled back as she pet his head and walked over to the kitchen. "Coffee?"

"Uh, no, I've never really had it."

"Oh, that's fine. But we should talk about how we'll be doing everything today and going forward." Aria walked back, holding the cup of coffee in her hands as she sat on the other end of the couch.

"Yes, yes, I was thinking I could help you clean up and cook, and overall help you out with everything around your house."

"Hahaha, nice try!" Aria laughed out loud. "I don't know what you're worried about. You were great last night! Your tongue is amazing, and your mouth is so warm and such a nice fit!"

"Th- thank you, I guess, but I don't feel comfortable doing it." Gabe blushed, secretly liking the compliments.

"Why is that? You did it with the worker guy, and me. Did you not like how I tasted!" Aria was clever and knew exactly what to say to control and manipulate him.

"No! No! It's not that! It just feels like I shouldn't be doing it!" Gabe panicked and raised his hands up, trying to calm down Aria.

"Really!? But you're so good at it! I don't think I've ever met anyone nearly as good as you. But I suppose you don't have to do it; you could just go back to where you were before."

"N- no no, I can do it. I don't want to go back." Gabe smiled awkwardly as he was now filled with new thoughts about how he was good at this and how even if he wasn't, he needed to do this to stay safe and get regular food and shelter.

"Okay good!" She grabbed the coffee cup with both hands and pulled up her feet on the couch. "You do still need to get better though, and don't worry, it won't be too hard, and I will help you.

"But I don't know mu-"

"I said, don't worry, I'll help. First let's get you a little more dressed up, then we can see if you can maybe get a client. Take of your clothes, I'll get some from my room." Aria quickly walked into her room.

"Okay." Gabe blushed as he slowly undressed himself. He felt embarrassed, of course, but he felt more grateful than before. The idea that Aria would be there with him, helping and guiding him through his new life. He knew he would have to deal with a lot of new things and feelings, but now he was looking forward to learning from them.

"Okay, I got a bunch of stuff, try them on one by one and we can see what we can do." Aria came out of her room, skipping as she placed a pile of clothes on the floor next to Gabe. As she leaned back up after putting them down, she got a closer look at his tiny little cock, and his plump cheeks hanging off of his body. She smiled as she enjoyed the view and quickly sit back down on the couch, enjoying her drink. "Go ahead! Try the different clothes, I'd like to see what you like first."

Gabe nodded as he bent over, unintentionally showing of his body to Aria, getting her a bit harder as she blushed herself. She sat down and took a big sip of her coffee as she watched the cute little femboy searching around for different clothes and trying them on. Gabe first tried on a tight pink top, yellow skirt and red high heels. This made Aria laugh out loud as she stared at the weird mismatch set of clothes Gabe was wearing.

"Why that combo!?"

"I- I just thought I would wear something that attracts attention." Gabe Blushed.

"Well yeah, but that doesn't mean dress like a clown!" Aria laughed as she finished her coffee and stood up. "You want to catch attention by using your natural gifts, not being a shining rainbow! Now how about you try this skirt, this shirt, and hmmm, let's see... And then some long socks and how about these for an accessory?"

Gabe keenly noted the clothes he was asked to wear. He noted all of them were neutral colors and not very eye catching at all. The shirt was a full sleeved, pale blue, crop top, tight enough to just give a little hint of his nipples sticking out. The skirt was a light brown miniskirt, surprisingly not as short as he was expecting. The socks were a near perfect fit as they ended just an inch or two below the skirt. He tried putting on the choker and hair ties but couldn't so Aria helped him and got everything on. When she was done, she took a few steps back and smiled.

"Almost perfect!" She smiled as she bit her lip. "What was your name again?"

"Gabe?"

"No, from now on, it'll be Gaby!"

"Gaby?"

"Yes, do you not like it?"

"N-no no! I like it! I like it! It's just a bit new to me."

"Don't worry, you'll get used to it. Also, lets put on the finishing touches!" Aria grabbed his hand and pulled him into her room, sitting him down on a chair in front of a mirror as she did his makeup. Once all done, she moved to the side and let him see.

"So! What do you think?"

"I- I look like a girl." Gabe stared at himself in astonishment as he examined his face from every angle.

"Good! That's the point! Do you like it?"

"Yeah, yes I do!" For once there was a tone of confidence and honesty in his voice rather than fear and confusion.

"Great! Now we just have to teach you some little tips and tricks for when you're working, but I think it's better if you learn that by yourself, I'll just give you the basics. Oh, and before I forget, keep these on, they'll be useful in attracting the right attention." Aria winked as she handed him a pair of pink panties that he quickly slid on and a pair of heels for him to wear which he also immediately tried on.

They both spent the next few hours in training Gaby to be more feminine and girly. First he was taught how to stand, how to walk, his speech all the way to seduction techniques and how to read and express body language and use it to your advantage. By the end of it, both of them were tired, Gaby however, was now far more confident, a far cry from when he first met Aria.

"Oof, that was some hard work, but you did good, much better than I expected."

"Thank you mistress" Gabe smiled as they both sat on the couch.

"How about we find you some work for tonight?"

"Are you sure I'm ready?"

"Well, you're already in your cute little outfit, I can't imagine it would be too difficult. I actually know of a place with an instant hookup and get some drinks."

Gabe smiled, while still a bit scared, he was far more confident, "Sounds like a plan, let's go?"

"Lets!"

Aria grabbed her jacket and gave one to Gaby. They both headed downstairs and were soon out and about. The town looked different to Gaby now. His perspective had changed. He no longer felt completely helpless and poor and as if he could possibly not see tomorrow. For the first time in a long time, he was smiling. Aria was very attentive today as she wanted to make sure he had learned from the training she had spent so much time on. They continued to walk for a while until Aria pointed at a bar far away. They entered the bar and instantly all eyes fell on Aria. The bartender smiled as he waved her over and some of the regulars stared at Gaby. They both walked over to the bar, Gaby now feeling a bit more awkward as she felt the eyes on her. Aria ordered them both a drink and got Gaby a little extra as she talked to the bartender for a while. Gaby was a lightweight and had never had alcohol before, he was almost instantly buzzed. Aria smiled, noticing he was a little out of it and started talking to the regular next to her, after a few minutes a deal was made and the regular stood up to go to the bathroom, Aria stood up and took Gaby with her.

"Now you just get in this bathroom, and wait for it. I'll be right outside if you need me." Aria smiled as she stood outside the bathroom stalls as she heard the man grunting in the one next Gabys.

Gaby stumbled inside the little stall, he quickly blushed as he saw the hole in the side. He knew what was about to happen. He saw the man in the stall next to him through the hole, grinning from ear to ear. He moved his head away from the hole, Gaby could hear his pants unzipping and falling to the ground. Then suddenly, the man just stuck his cock through the wall, letting out a little chuckle as he did. Gaby Stared intently at the big piece of meat sticking through the wall. It was yet again a very different kind of cock. The skin was much darker than any of the cocks he had had before. The smell was also a little different, while not as sweet as Arias, it did have a certain similarity to it but he could not put his finger on it. The pubic hair was also fairly well kept compared to the man before, perhaps that was the reason? Either way, the only difference he hadn't confirmed was the feeling and taste. He was just about to reach forward and grab it when the man smacked the wall.

"Hurry up already! I know its big but you don't have to take all day!"

"S-sorry mister!" Gaby blushed, feeling a bit embarrassed.

Gaby leaned forward, grabbing the massive member with both hands, gently rubbing it. It felt much harder than Aria's, even the skin didn't hang onto the muscle the way it did with Aria. There was also less of a curve and it wasn't as girthy. Gaby smiled as he began to enjoy it more than feel embarrassed about it. The veins were pumping in his hand as he leaned forward, his tongue touching the tip of the cock and resting there, absorbing the few drops of precum pour onto his tongue. He closed his eyes as he compared the taste of this new precum to the ones that he had already tasted, he played with the tip with his tongue, as if he was begging for more. On the other side he could hear the man heaving heavily, little gentle moans as his cock was now fully erect. Gaby slowly let the cock slide down his throat as he began to move his head back and forth, now only using his hands for support as he held the stall walls. He felt it go down his throat, and his throat tightening around it making it throb harder. He began moaning as he felt his tiny little cock precum and make his new panties all dirty. He blushed but he didn't want to stop. The scent of the cock was taking over and he started bobbing his head back and forth faster and faster. The man moaned louder, now turning to a groan. Gaby closed his eyes and wrapped his lips around his cock as tight as possible and started sucking it in deeper while bobbing his head back and forth faster and faster. It took all of two minutes of that and was quickly pumped full of cum as the man let out his final moan. Gaby was growing more and more accustomed to the taste of cum and quickly swallowed all that he could. He made sure to clean the cum left on the cock and waved goodbye to the man. As soon as he got out he saw Aria with her back towards him and counting money.

"Oh, there you are! Clean up now, I'm taking you shopping!"

"Shopping for what?"

Aria gently lifted his skirt to see his dirty panties, "I thought you might need some new ones."

Gaby blushed, but quickly it turned into a smile. He quickly cleaned up his face and clothes and came back to Aria, "let's go!"

"Yes, and before I forget, here is your cut!" Aria smiled as she handed him $20.

They headed out of the door, leaving behind the dirty bathroom and off to a new different life. They walked through the streets, only this time Gaby had a different perspective. As they walked through the city as the sun set and the street lights turned on, they finally reached a large store with a lot of lights and a tall glass front that showed of a couple of mannequins in the front wearing some slutty lingerie and in the back they could both see rows upon rows of clothes, toys, cages, machines and tools. Aria grinned as she grabbed Gaby by the arm and pulled her along inside. They went straight to the dress aisle but Gaby could not stop looking at everything else. He had never been in such a huge, well lit, and fancy looking store. As Aria was going through the dresses for Gaby she was approached by one of the shop assistants.

"Hi! Welcome to Sissy 'R' Us! I'm Angela! How can I help you today?"

"Hi Angela, this is my... friend, Gaby. She needs to get some new clothes an-" Aria was just about to continue but was interrupted by the tall, blonde young shop assistants laugh.

"Hahahaha, its okay, you don't have to make stuff up here." She covered her mouth as she laughed, showing off her newly manicured nails. "I'm guessing he's a new sissy? Or at least new to the lifestyle?"

"Y-yeah." Aria blushed, feeling a little embarrassed. "He just started yesterday, and I'm just helping him out."

"Well, lets get to the basics first then." Angela smiled as she turned around and started walking to the back. "We have a changing room here in the back with some starter kits, we should definitely start there."

"Come on Gaby!" Aria yelled as she pulled his arm. Gaby was completely lost as he was still taking in all the things around him.

Meanwhile Aria couldn't take her eyes off of Angela's firm ass tightly wrapped in her skirt, outlining her curves. They continued a somewhat long walk as the store was just massive. They finally reached the back which had multiple pod like rooms. Angela opened one of the larger ones and stepped in, signaling them to join. The inside seemed even larger than the outside. There we're a couple of chairs, a long table with a bunch of toys, multiple shelves also filled with toys and what seemed like an examination table with stirrups.

"Can I see what we're working with?" Angela smiled as she got on her knees and looked at Gaby.

"Sure!" Aria smiled as she grabbed Gaby's skirt and pulled it up, showing Angela the dirty panties.

"Hahaha, I mean, how big is he?"

"Oh, well, he's pretty small." Aria reached down and pulled down the panties revealing Gaby's tiny little cum covered dick.

"Oh my!" Angela laughed out loud, again covering her mouth, "it's pretty small!" She stood up and walked over to one of the tables with cages and started going through them. "Why don't you take a seat on the examination table and remove all your clothes.

Aria helped him take off his clothes. Gaby was still embarrassed and it finally hit him, what was he even doing here? This seemed a bit too much. But he still got onto the table, not wanting disappoint the one new friend he made. Angela grabbed a few cages and turned around, controlling her urge to laugh out loud at the tiny little dick right in front of her.

"Let's get you strapped in first." She smiled, comforting him as she and Aria both tied his hands and feet to the table. "Now which one do you like?" Angela smiled as she showed Gaby multiple cages in different colors and shapes.

"Th-that one, the light blue one." Gaby blushed as the other two giggled.

"Oh, personally my favorite is the pink one." Angela smiled

"Will, will it hurt me?" Gaby asked, a bit scared.

"Hahaha, Of course, but don't worry, you'll learn to love it! I did!" Angela smiled and backed up, lifting up her own skirt to show them both her little silver and pink flat cage. "Although it'll be easier for you since you're already pretty small."

Aria and Gaby we're a bit shocked as they both didn't realize she even had a penis. Aria almost instantly got an erection as she saw the tiny little cage between two thick thighs. Angela noticed and giggled realizing what had happened. She leaned over Gaby, gently placing the cage on the cock, locking it on and grinning.

"There we go! Now, lets see your little bussy!" Angela smiled as she lifted the stirrups and got lower to look at the hole. "Oh wow! You're a virgin! That's rare!" She gently rubbed her finger on the pink little puckered up hole.

"Yeah, like I said, he is still very new." Aria chimed in, still thinking of Angela's body.

"Well, we should definitely get a plug in there." She turned her attention to Aria, "Are you going to be the primary user?"

"Yes!" Aria blurted out, not wanting Gaby to answer who was still getting used to the cage while being tied up.

"Well, we should get one according to size then, can I see your cock?" Angela almost seemed to blush as she asked.

Aria grinned as she dropped her pants instantly, letting out her semi-erect cock. "What do you think?"

Angela got on her knees and got very very close to Aria's hung member. "Wow! You're pretty big!" She ran her finger from the tip to the base along the shaft and back, feeling the curve and girth, coincidently getting Aria harder. "Well, I can't really tell, you'll have to use it on me for me to be able to tell." Angela giggled as she stepped back.

Aria blushed, not expecting this to go this way but was more than willing to help. Angela pulled down her little panties and bent over. She reached from between her legs and pulled out a rather large plug. It made a satisfying pop sound as it came out and her hole was already nice and wet. Aria smiled as she pointed her cock towards the hole, gently rubbing her tip against the very willing hole. Aria let out a soft moan as she felt the wet little hole beckon her cock. She slowly slid in, almost half way through and took a few seconds to enjoy both the warmth of Angela's bussy and her little moans as it grabbed her cock and almost felt like massaging it. Aria pulled her hips back and gave a light thrust forward, now deeper than before, she bucked her hips again, getting even deeper and making Angela moan out even louder. She smiled as she began to thrust in a rhythm, slowly picking up speed, she grabbed tightly onto Angela's ass, letting her nails dig in and gave it a little spank. She sped up even more until she felt her hips slamming against her ass. She kept pounding away, feeling her balls smack her tiny little cage each time. Angela moaned loudly as she felt Aria's cock throbbing inside her. Aria moaned as well, knowing she was about to blow her load. Aria leaned forward and tightly hugged Angela, exploding inside her. She quickly filled her up inside, both groaning and shifting to huffing as Aria finished and slowly pulled out her cock and fell onto one of the big comfy chairs, her cock leaving a trail of cum. She huffed and smiled as her cock slowly got softer. "So, how was it?"

"Great!" Angela huffed as well as cum dripped from her bussy. "Let me just rest a bit and I'll get you some plugs.

Both of them panted as they gathered their breathe, meanwhile Gaby just looked at both of them. He hadn't really seen something like this. He was torn, while he was scared f what just happened, he was also extremely turned on. He didn't really know how to feel about the whole situation. Angela looked over to Gaby and walked over after putting her plug back in and slid on her panties. She leaned down and flicked the cage.