The Acceptance of Cassie Ch. 05

Chapter 5 -- Expansion

Eddie and Andy sat at a high table in the Court pub area, a pink cocktail and a pint of beer on the table in front of them. To any onlooker, they might look like two friends sharing a drink. Only they knew each other for their sissy nightlife. Only they knew the other was wearing panties under their male clothes, plugs in their asses, and not a strand of body hair existed under their eyebrows.

"Oh my god, you're so perverted! I love it!" exclaimed Eddie. Andy blushed in response and chuckled as he sipped his cocktail in response.

It was now the day after Cassie's foray with Anna, and Edwina (currently as Eddie) had invited Cassie (as Andy) out for a drink at The Court. Edwina promised a trip to the gloryholes afterward too if Cassie was game. And of course, she was. She cleaned herself out thoroughly and shaved around her cage in excited anticipation for the night ahead the moment she arrived home from work.

"Is that the mask there?" Eddie asked, and Andy instinctively looked over at his medical mask, sitting on the table next to his wallet and drink.

"It sure is" Andy replied, picking it up off the table. The mask, discreet from a look, was soaked in dried semen.

"I'd ask to smell it, but I'm not super into that sort of thing. But I think it's hot that you are." Eddie said.

"Thanks," said Andy with a smile, "I'm sure there's loads that you're into that I'm not into!"

"Spoken like a true paragon of sexual health" replied Eddie, taking a sip from his beer.

They sat at a high table inside The Court, sipping away at their drinks. They had been there for around 10-minutes now, sufficient time for Andy to update Eddie on his previous evening with Anna. He proudly wore the mask that Anna had provided him with as a badge of honour, wearing it whenever he left the house that day, including to work. He realised with certainty he had a strong fetish for odours, given his horniness all day, and his tendency to throb against the cage that only Anna could open now.

"I don't think I'm into chastity as much as you either, at least not on myself. I definitely like it on my partners though... at least the sissy ones," Edwina said, with a wink, "but definitely not on the cocks I'm gonna have fun with tonight."

Andy gave a cursory glance around to ensure they hadn't been overheard for the tenth time that night. Eddie scoffed and said, "You don't have to worry here honey."

"Sorry," said Andy, "I'm not used to being this open with this stuff."

"That's fine! How long have you been doing this now, anyway? Being a sissy?"

"Um... about a week I guess, this time around, after the purges I've had and stuff. I've been off and on with it the last few months, and only really bought clothes and makeup recently. But really it's only been serious after my first two experiences this last week." replied Andy.

"Oh my god, you're new and already in so many peoples' dream situation! I can't believe it. Were you fully straight before this?"

"I guess I was, but I always into trans porn and hentai. I guess I only really acted on it when my long-term relationship ended. Then I really considered this stuff as an option. I never really considered myself attracted to men before that. I'm still not so sure I am. It's something else about them."

"You definitely look like you're enjoying it too much to purge right now," Eddie said.

"Not going to lie Eddie, but all the chaos and newness of it is making me a bit scared. But I am loving it, so I'm pushing myself not to run away from a good thing."

Andy was unsure where that statement came from. It seemed to come from deep within him, from within Cassie, and really acknowledged the chaos of the last few days. This was all still very new and freaky. It wasn't how he was used to existing. But it was like moving to a new city, he supposed. It was unfamiliar and scary until you got used to it.

"I'm glad you're sticking with it," Said Eddie, "Though it's always good to have breaks."

"For sure." Said Andy.

"It seems like you're enjoying being a more submissive little femboy underneath old straight Andy," Eddie said, taking a sip of his drink, "And there's nothing wrong with that! I mean look at the girly cocktail you ordered, while here I am with my beer."

Andy hadn't even considered it. The pink cocktail he had ordered on the menu didn't even register to him as out of character. Perhaps his sense of self, and comfort in his existence, was indeed expanding.

"Have you thought much about how you identify, gender wise, now that you've had some experience?" Asked Eddie.

"Honestly it hadn't crossed my mind," said Andy, "I haven't really thought of a label at all."

"Fair enough! I just really like the gender identity side of things, especially when it comes to this fetish we both love. I identify of non-binary and genderfluid, in case you were wondering"

"Oh cool. So not trans? You like being a bit of whatever you want?" Andy asked.

"It took me a while to figure out how much of this was a fetish and how much belonged to the person that I felt I was. A lot came from porn addiction, as I'm sure you're familiar with, so it was hard to unpack if I felt like a woman or not. I settled on just deciding to be me, and the me I get to be in different situations changes. What I do know though is that I just love guys and their dicks. I'm not a fan of vaginas. They gross me out!" Said Eddie.

Andy laughed, "Fair enough! I think I still like vaginas, personally. And, well, this won't surprise you, but I kind of like the smell."

"You perv!" Laughed Eddie, as he sipped his beer.

They changed into their sissy personas together not long after. All the talk of sex and sissy life seemed to have made Eddie hot and heavy, his eyes taking on a distant and longing look that Cassie could easily see was growing. They took their bags from the table and wandered through the paths at the back of the bar to the secret entryway. As they walked past the attractive receptionist, she raised her eyes and greeted them.

"Back again, I see?" She said, looking directly at Cassie.

Cassie hesitated a moment before she replied, remembering that last time she entered looking like a girl. After a moment she did remember that she left looking like a boy, however.

"Sure am! It was a lot of fun last time." Said Andy. Stating the truth of his enjoyment was a challenge against anxiety, and he felt he channelled Cassie from within to say it out loud.

"I'm glad you enjoyed, darling." The receptionist replied.

"Make sure you send some of them Eddie's way this time too though" Andy said, with a giggle.

The receptionist laughed, "I most definitely will, if that's alright with you, Edwina dear?"

"Of course!" Replied Eddie, as he continued down the hallway.

The pair went up the stairs to the bathroom. Edwina adopted her usual goth girl aesthetic, the same clothing items as before, and Cassie adopted the underwear clad blonde-haired persona of her affection. They did their makeup together in front of the mirror like real girlfriends. Today, Cassie added her dirty medical mask over her made up face, adding to the mystery of Cassie's visage underneath, and exposing her to the smell of spunk constantly. Her cage bulged against her panties, causing Edwina's gaze to linger there for a moment, before she diverted her eyes to Cassie's and smiled. Edwina then continued to apply her eyeshadow.

Before they left the room, Edwina grabbed Cassie's arm, and turned her so that they were face to face. Cassie saw Edwina's black lipstick up close and marvelled at her plush lips and totally hairless face.

"Can I kiss you, before we go in?" Edwina asked.

Cassie was surprised. She hadn't considered this, but was feeling very open this evening, and decided that there was no harm in it.

"Sure," she said as she removed her mask.

Cassie relaxedly accepted Edwina's supple peck against her lips. It was a delicate, gentle moment, that left them both sighing.

"You smell like cum" Edwina said, with a smirk, as Cassie replaced her mask.

"I've got one more rule to tell you tonight, by the way," continued Edwina, "You can actually fuck here. But if you want to, you have to exit and go all the way down the hallway. Then, if you go into the "Fuck" section where the men are, you can enter another room on the other side of their hallway. They've got a bed in each. Only catch is that you have to walk past all the dudes before you can go into a room. But the men can't come get you -- you have to choose to go there yourself. I've only done it once. Feels a bit depraved, and you're on show for everyone you go past. But if that's your thing, go for it."

"Thanks for letting me know," Cassie replied, smelling her alcohol-tinged breath mingled with cum under the mask as she spoke.

The thought of fucking in the rooms intimidated Cassie, but she was glad of the knowledge. Her thought went back to the man whose eye she had caught through the hole last time, who told her he was looking forward to seeing her again. She tried to remember exactly what his cock was like as she followed Edwina to the "Suck" door, and they entered a room each.

"See you soon!" Said Edwina, as she took room 2, and Cassie took room 1 again.

Cassie felt an odd sense of nostalgia as she knelt in Room 1 and awaited a cock to enter through the hole she faced. She longed to touch herself in anticipation and was met with only the hard resin material of her pink, off-brand holy trainer. She tried to settle for only the flexing of her kegel muscles against the plug in her ass and found some entertainment there. She was satisfied to find herself leaking precum out of her cage after a few minutes of clinching the muscles around her prostate so that the plug rubbed against it. All the while sounds of shuffling feet and moans echoed through the gloryholes, and Cassie wondered when a cock would come to greet her.

She heard someone enter into Edwina's room next door followed by intense moaning. Cassie rubbed her plug imagining Edwina sucking someone off, pushing it as deep into herself as she could get it. Not long had passed, between the moans of Edwina and an anonymous man next door, when shuffling feet sounded next to Cassie's gloryhole.

That first dick of the night lasted a while. It was at least 6.5 inches in length and had an initial musk to it, but nothing confronting. It smelled like a dick, and that was exactly what Cassie wanted. Cassie wanted to savour it and enjoyed every moment of her time with the erect member, and she did so, licking it like a lollipop and fondling its balls. She swallowed most of the cum it provided her with, though there wasn't much that came from that cock.

The rest of the dicks came to Cassie's gloryhole intermittently for the next hour. As she licked, caressed, kissed, and suckled on the dicks, she felt her sissy clit respond in turn and strain against the cage that housed it. Eventually, she reached a dull throb of what felt like an erection that went inside her crotch, rather than lengthening outside her. She had never felt this way before, and the urge to touch herself grew maddeningly strong. When she felt herself coming close to succumbing, she would remember she was powerless, and her frustrated energy would be redirected into renewed energy in pleasing the cock in front of her, often to a responsive moan from behind the wall. Chastity was powerful, Cassie could tell. But she held the opposing thought in her mind too. She found it incredibly hot but would do anything to have it taken off her. She wanted it but didn't want it. She was driven wild with lust.

This wild nature of her lust led her to disappointment also. In the hour, she had served four cocks and counting. One had only lasted for a minute. She was on her phone more often than she was serving dick, and she longed to edge her cock, but couldn't. She took some selfies next to the hole but didn't feel overly compelled to send them anywhere, except to send one to Anna. She did so, then idly looked at previous messages from Anna, because hadn't gotten back to her last message. They had just been discussing the hentai made by the artist "Aian" and Anna hadn't replied since Cassie got to drinks with Eddie. Cassie had last sent her: "Have a look at the manga called 'Collateral.' It's great sissy literature, trust me! Just going to the Court now xx." The photo that was just sent only said "delivered," just like her message about hentai.

Cassie was staring at that message, longing for the three dots of Anna typing to appear, when she heard someone enter the other side of her room. She didn't hear any pants coming off, and when she turned to face the hole properly, she saw eyes gazing back at her. These were eyes she recognised. They were blue and attached to a surprisingly youthful face.

"Want to fuck?" He asked.

Cassie took a moment to collect herself. She knew she was lusty. She was wild with it. Her more rational mind, though quiet, was telling her to be careful. But the mind of a sissy in chastity is a powerful thing. A licentious thing that will do anything for a fix. And it spoke for her.

"Fuck yes." The sissy voice said.

Cassie was right to be intimidated about walking into the "fuck" side of the hallway. There was no one on the way there, but when she entered, her mask back on and underwear scantly covering her nudity, she was greeted by the sight of three or four men down the hallway waiting at various doors or lingering about. They all fixed their eyes on her, hungrily, and she knew that they wondered who she was here for. There was only one reason a sissy came to this side. And that was to serve. She clutched her bag in fear in one hand.

She hadn't noticed the man who had asked her here, waiting directly to her left as she entered. He looked down at her, given he was at least a few inches taller, and took her arm immediately.

"Thanks for coming sissy." He said and guided her to a room on the right side of the hallway. He had strong hands with skin that was course and rough. Cassie thought they were the hands of a tradesmen and wondered if perhaps this man spent his days on a work site, laying bricks or working on carpentry, messaging sissies on grindr and spending nights at the gloryholes behind the court.

As she entered the room that he guided her to, she stopped wondering at the man's background and noted the features of the room she was about to be voluntarily violated in. The room was narrow, not much bigger than the gloryhole rooms. It had a single bed with a mattress only covered in a fitted sheet. There were no pillows. The floor was tiled, giving the room an "easy to clean" aesthetic. There was a massive bottle of lube on a side table, the only feature adorning it was the label "WATER BASED." Under the table was a small plastic bin with a plastic bag in it. The light overhead was dimmed, clearly not fluorescent, but still bright enough to see all the debauchery that occurs within the room.

Cassie froze as she entered, like a deer in headlights, but the man was at ease. He guided Cassie forward with a hand gently on her back, removing it only when he shut the door behind them and began to unbuckle his belt.

"I like your mask. The mystery is so hot, even if I have seen your face before through the gloryhole. The choker is also a nice touch. You look ready for cock, like a good little sissy."

"Thank you" said Cassie, surprised by the ease with which she said it. Her freeze response seemed to be calming. She placed her bag on the floor next to the door.

"That's thank you Daddy, please." The man said.

Cassie wasn't super into the whole daddy thing, but she complied nonetheless, even if it made her feel a little weird.

"Thank you, Daddy." She said.

"That's better" he said, as he leant down to slide his shoes off, enabling him to remove his pants. Cassie watched him do it, vigilant for the sight of his cock to appear out of them. She was not disappointed. It was just as girthy and long as she had last seen it, though notably a little more flaccid. He bent back down to his pants, piled on the floor, and removed some things from one of the pockets. The first was his phone. The second, two condoms, which he placed on the bed.

"Would you like me to take some pictures and videos while we go at it? I won't without your permission. And I can send them to you after if you like."

Cassie stared at the phone and didn't meet his gaze. She knew what her horny mind wanted. It wanted masturbation material for later and hot videos to show Anna and Edwina after this was done. Her rational mind knew it could be bad. Hell, it could be blackmail. And yet, she knew she wouldn't be recognisable. She looked dolled up and nothing like Andy. Someone would have to be really looking for him in the visage of Cassie to find him, and this man had no idea who Andy was. So, what did he have to lose? What did Cassie have to gain?

Cassie won over.

"Yes Daddy." She said, eyes downcast.

He grinned broadly and opened his phone, readying the camera. He let the arm drop and looked at her expectantly.

"Warm me up, would you love?" He asked, as he moved toward Cassie, delicately removing her mask with both his hands, placing it on the edge of the bed, next to the condoms. He then turned back and pushed her shoulders down so that she knelt in front of him.

Cassie was happy to be back on her knees. She took him in her mouth, slowly and supply, as she tongued the flaccid skin and ran her tongue over the tip of his penis. She loved the feeling of him slowly getting hard in her mouth over the next minute. She experienced a moment of hesitation for using her hands, remembering the way the previous "master" she had served as her second cock and the way he had abused her. But she tried, and the man she now served moaned in response. He seemed to like to have his balls fondled. She also took a few breaks to put her mouth of his balls too, and run her hand along his meaty shaft, now fully erect. She marvelled at the smoothness of his cock and balls, and she loved the handle dicks beside her own, taking breaks to taste and to caress.

"Nothing better than a blowjob from a sissy. Good god you just know what you're doing don't you?" He said, as the 'click' sounds of a phone camera sounded intermittently.

"Mmm" moaned Cassie, her mouth suckling on the tip of his dick as her tongue undulated on the underside of his head. Embracing the moment, she realised she was enjoying putting on a show for his camera.

Some more minutes passed with the mam moaning and the camera clicking. The clicks began to stop, and the man began to moan more, and Cassie wondered if he was taking a video.

"That'll do for now sissy," he laughed, and pushed her head back with one hand, "I brought you here for more than this. Get on the bed into doggy."

Cassie complied, rising to her feet and getting on the bed. She did so with her eyes down and did not look at him. Even despite all the time she had embraced her sissyhood, she still felt a bit afraid to face him. When she was on the bed, she lifted her ass and placed her face against the bed, doing her best to arch her back.

"Wish you had heels." The man said, pinching one of Cassie's toes. He then went to the side table and grabbed the gargantuan bottle of lube.

Cassie made a mental note for a shopping trip online soon. Heels might be a nice touch. Her feet were just bare tonight.

As the man came back around to the bed, he drew her panties down enough to see her ass, letting out a brief scoff noise when he saw the plug, before wiggling the plug out of her ass with a "plop." He placed it on the side of the bed with her mask and ran his hands down her panties again to pull them low enough to see her sissy purse and clit.