The Acceptance of Cassie Ch. 07

Story Info
Cassie confronts her attachment when Anna grows distant.
4.2k words
4.66
4.6k
9

Part 8 of the 11 part series

Updated 06/14/2023
Created 01/07/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Ash_P
Ash_P
90 Followers

Ch.7 -- Attachment

It took Andy less time than he thought it would for him to adjust to his new routine. In fact, he hardly consciously recognised that a month ago this would have felt weird. Each day as he walked in and took off his ironed white shirt and tie, to reveal the bra underneath, it only felt natural. He placed his bag exactly where it always goes, becoming Cassie automatically, smiling at the sheen of his nails under translucent polish. Invisible to most but clearly a sign of his accepted femininity underneath to those who looked.

Taking his shirt off also revealed the discreet waist clincher that he now wore out every single day at Anna's request. She asked if he wanted to look more feminine, and Cassie definitely did. She looked down at it and decided to leave it in for another hour. It was good training, she thought.

Taking off her work pants and almost naked now, she looked like a smooth femboy in standing in the entryway of Anna's apartment. Cassie felt glad that all of her bare skin could at last breathe. She felt the nerves on the skin of her silky legs tingle. She felt the sensation of her cage, nestled in her panties, wrapped around her flaccid cock. And last, she felt the fullness of the plug in her ass, pleasantly filling her up.

There, comfortably in the doorway, was Cassie the sissy. Simply in the moment after a day at work as Andy, dressed only in underwear and clincher. She loved this moment.

It had been a month of this new routine. Anna never really asked Andy to become Cassie every time he came in, but he just sort of... did it. Because he wanted to. Anna really only had one request for him. After his short break, she stated, "I want you to a sissy, as often as you can be, and just let me know when you need a break, ok?" and Cassie didn't need long to respond in the affirmative. The break that Andy got was the evenings he spent at his house, but even then, whenever his housemate wasn't home or he was just in his room, he was fully Cassie. He was watching hypnos while relaxing in girly attire. Andy went out into the world to pay the bills and Cassie lived behind the closed doors.

And Anna? She loved every second of it. Anna could come home from work and expect a mouth, ass, or hand ready and waiting to please her. She was horny all the time with her hormones at the level they were right now. Such was the life of a trans woman.

"I'm like a pubescent boy, I could go any time." She told Cassie, as they laid in bed one evening, her cock already resolutely erect after the second fuck of the night.

"Amazing..." Muttered Cassie, taking the throbbing member in her hand and squeezing for dear life. That was a good night.

Cassie also loved it because she often had to work for an orgasm. Sometimes it was a challenge with Anna if she was on a certain part of her hormones cycle. It was a good thing Cassie loved to challenge herself when it came to pleasing Anna's beautiful cock.

On this particular afternoon, Anna hadn't come home yet, but Cassie was happy to get comfortable. She strolled in her underwear to Anna's room and placed her boy clothes in the drawer that now belonged to her. The drawers also contained some work clothes and an emergency set of casual shirt and shorts. These were all the boy clothes she had here. The rest of the drawer was populated with panties, tights, skirts, oversize jumpers, crop tops, and sex toys.

Cassie picked some comfortable attire, a pair of booty shorts and a baggy sweater, and sat down on the coach to watch some TV. She texted her parents, nonchalantly as Andy, as they requested a quick check in to see how Andy was doing.

Doing great, Mum. Thanks for checking in.

Glad to hear it sweety. And how is your girlfriend, Emma?

You mean Anna. She's great mum. Thanks for asking.

So glad you have a partner again after that last one.

Thanks mum xx

Giggling slightly to herself that she signed off with two xx's, so girly, she closed the window and changed to text Anna.

When are you home tonight bb?

Message: sent

Waiting. Waiting. Waiting. Cassie rubbed her tight sissy purse and clenched and unclenched her bussy. Underneath, she even felt a bit anxious, wondering at what Anna was doing. Sometimes, against his integrated sissy persona, he wondered if Anna considered much of how he was feeling.

She idly scrolled Andy's emails also, given his lease was up in a few weeks. Covertly, he had applied for a single bedroom apartment at a building right down the street from Anna. And he was hoping that by moving closer, and by being away from his old housemate, things with Anna might get more serious. He also hoped his small nagging anxiety about Anna and what she did whenever she wasn't with him might abate. And he though that at least he would live alone and not need to worry about prying eyes anymore.

Three dots. An excited throb from a cock still stubbornly trying to inflate in its cage.

Home soon! Just wrapping up now. Want me to bring home a wine?

Cassie smiled. Always xx.

Cassie decided to climb into the shower shortly after to get clean before Anna got home. As she took her panties, bra, and waist clincher off, her thoughts did drift briefly to her life only a month and a half ago. Sadly masturbating to sissy porn most nights, watching Netflix occasionally with his housemate, playing Minecraft sometimes in between messaging aloof women on tinder...

Some part of him wanted to go back because that might be what is expected of men. These things were what people at work assumed he did outside. And he acquiesced, lying to them, saying to them that he did do these things when behind closed doors he became a licentious pervert. There was an element of shame to this life, even still within Cassie's mind. But it was quieter, and she chose not to pay it heed.

So, as she showered and cleaned within her cage with the powerful jet of the shower, Cassie thought about how this was their routine now. She was always a bit of an outsider who didn't have too many friends in this Perth since she moved here from over East. It was hard to make friends in Perth. So, she didn't really need to be anyone else besides Andy during a workday, and all her other time was spent as Cassie with Anna. She didn't know it was the change her life always needed until she made it.

It was rare for her to spend more than a single night a week alone, and usually that night was spent with Edwina at The Court before she retired to a bed by herself. It was a great pastime, and Anna was happy to abide it if she was busy that night and Cassie sent pictures. Cassie loved the wild and hungry way Anna looked when she asked for the stories of the nights spent pleasing anonymous members.

Each night with Anna was spent with lusty sex. Anal wasn't always an option, because that's the reality of a pleasure hole also being functional for other bodily reasons. Regardless, they lusted over each other and found sex in other ways. They used any device they had to bring pleasure. Cassie found ecstasy in the feeling of a vibrator on her cage. Anna loved having Cassie use a fleshlight on her.

And every now and then, Anna would want something in her ass. Once, she unlocked Cassie's cage and asked Cassie to fuck her, and Cassie did... for a few minutes, until she found she was soft.

"What's wrong my dear?" Anna asked, concerned. "Are you okay?"

Cassie blushed and said "I'm too busy imagining being under you to be on top of you."

"Oh sweetie, I was worried you didn't like me anymore!" Said Anna. She may have been a pro as a top, but she got sensitive sometimes too.

Cassie leant down and kissed her hard on the lips.

"I'll never stop loving you." Cassie said. Anna appeared not to notice the L word, but Cassie noted a lack of reciprocation under her horny brain's dominance. She forgot it quickly, at least consciously.

Cassie then substituted her cock for a flowery pink dildo. She knelt by the edge of the bed, with Anna's legs spread, and used her hands to fuck Anna's ass with the dildo while she wrapped her mouth around her cock. She felt Anna's entire body shake as she came, showering her tonsils with gooey spunk. She loved to hold her lips on Anna's still spasming cock as it began to deflate just a little post orgasm.

A few days after Cassie's attempt at topping, Anna came home with a strap on. Anna then harnessed Cassie up and had Cassie fuck her with the same flowery pink dildo but in the harness. Cassie's caged cocklet had no part to play in this type of sex. It made Cassie feel gleefully girly while beautifully emasculated. Her dick wasn't important here. Cassie discovered her favourite part was when Anna came onto her own stomach, and Cassie ran her tongue all over Anna's exposed belly, and into her belly button, cleaning up every droplet of cum from her smooth skin. Anna moaned in glee the whole time.

As Cassie exited the shower in a bathrobe she thought the routine was good no matter how they fucked. She thought that even when she eventually sat down that afternoon, drinking wine after a workday and watching Netflix with Anna. They cuddled on the couch and enjoyed each other's presence, the power dynamic surely swaying toward Anna but always balanced by the choice each of them had in their strange relationship.

Sometimes, though, Anna would have requests for Cassie. Or challenges. She liked to push the boundaries every now and then and see what she was up for.

Once, she wanted to see if they could go grocery shopping while Cassie was all dressed up. But Cassie wasn't allowed to wear underwear.

Another time, she bought Cassie a VR headset and asked her to watch hypno for an hour with a buttplug in. Cassie loved every second. She took the headset off and felt more honry than she had ever felt, and when Anna graciously slid into her, she felt like her mind fully left her body.

Always the internet user, Anna often found these challenges on Reddit or in porn. She was always eager to pitch them to Cassie, and as she found, Cassie always said yes. Or at least had a try! The "try," or the only one she couldn't complete she should say, was when Anna brought home a horse cock sized dildo, and Cassie maybe needed a bit more preparation and training for that one.

"How do you feel about tattoos?" Anna asked, this one evening while they sat on the couch.

"I've never really considered it." Cassie replied.

"Nothing big or public, just something small." Anna replied, confirming what she was thinking of.

"I don't know, maybe? What do you have in mind?"

"Have you ever been on sissyology? On reddit?"

"A few time, yeah" Said Cassie, turning now to face Anna.

"How do you feel about getting their logo on you? It's like a little sissy symbol."

"I mean... wow, that's pretty permanent though."

"It's okay if you don't want to!"

"What if someone sees?"

"You are pretty concerned with what others think aren't you my dear."

"I am... I'm sorry about that, you know?"

"That alright, my dear Cassie. The symbol isn't all that recognisable anyway, and I was thinking of getting it just above your little caged cock."

"That does sound quite hot, actually. But I'm not sure about it being on my body forever."

"How about we get one of those longer lasting temporary tattoos first? And we see if you like how slutty it makes your midriff look?"

Cassie contemplated a minute, and Anna turned away from the TV to meet her gaze and smiled.

"Sure!" Smiled Cassie, and Anna ran a hand up her thigh in affirmation.

Later that night, Anna took a permanent marker and drew the marking just above Cassie's cage. It looked like two curved S' mirrored together to look like a heart. Admittedly, Cassie grew to adore it as she looked down at the patch of skin above her bouncing cage while she rode Anna. As they changed positions, Cassie kept looking back down at it, and when Anna finally came and they cuddled together in the post orgasm glow, Cassie turned to her.

"I'd love to try the temporary version. I like the little reminder on my skin of my... place, I guess?"

"Glad to hear it" Anna sighed, and kissed Cassie's cheek, exhausted.

As they lay in bed in the post sex afterglow, Cassie noticed, as she often did when she wasn't cock-addled and horny, was that Anna could seem a bit distant. It wasn't every day, so Cassie often caught herself wondering if it was any concern, but it was enough to play on her mind. Cassie may have been a newly accepted sissy, but she was still human and victim to attachments. She was very attached to Anna now. Anna, in her own mind, had far more control over Cassie than she seemed to realise. She controlled Cassie's orgasms, and sexuality, but she also had complete control over Cassie's emotions too. On a day where Anna was distant, Cassie struggled to focus on work or on anything before she saw Anna.

Tonight, she wondered this as Anna seemingly rolled away from her to play on her phone and ignore her. Cassie then got on her own phone, taking Anna's lead, but really wanted Anna's attention instead.

It seemed she was a clingy sissy. She just wanted to make Anna happy. And she was deeply fearful that Anna would get tired of her. She wondered who she even was without her, sometimes. It wasn't healthy, but she didn't know that yet. It was also just like Andy's last relationship, though he hadn't made the link in his mind yet. This still felt so new that it felt impossible that it could be anything like what life had been before.

Eventually, Anna asked if Cassie wanted to shower, so they hopped in together. After they had finished washing themselves that night, they lay in bed on their phones again. Cassie was looking at memes on reddit when Anna piped up: "I've got a new challenge for you"

"Oh?" Replied Cassie.

"This is a big one though, especially for me too."

"Tell me!" Cassie said, excitedly.

"How would you feel if we brought a man in and I had you suck him off?"

"Bring a man here?"

"Yeah, an old flame just messaged. I thought it'd be fun!"

Cassie took a moment to think. This must have been what Anna was doing on her phone, she thought. The male part of her mind was silent. The sissy side wanted a new cock to suck desperately. But the attached side worried that Anna might not want her there after all.

The slutty side won out. As it usually does. And Cassie kept her feelings to herself.

"Cool, I'll message him!" Anna confirmed, and Cassie smiled back. Though it wasn't a smile that spoke of deeper inner satisfaction.

The man who arrived at Anna's apartment the following night had not been what Cassie expected. She thought it would be some sort of young professional, but instead it was a tradesman, and he seemed more familiar with Anna than she had expected. He moved about the apartment like he had been there before, putting his high visibility jacket down on the couch like it belonged there. Cassie felt violated, and not in the good way that she was accustomed to. She felt violated because someone had come into her space.

"Is this the sissy?" He asked Anna, motioning toward Cassie, who sat on that same couch.

"She sure is. Isn't she cute?" Said Anna, moving to Cassie and kissing her on the forehead.

"Very." Said the man, smiling at Anna, then pulling her toward him and kissing her full on the mouth.

Cassie knew a moment of panic then that she hadn't expected. Her mind went into arrest watching the object of her affection being taken by someone else. Even though it was a male, and Cassie loved their masculine dominance, this felt different.

It felt just like when Andy found out his ex didn't love him anymore.

Then everything blurred for Cassie as she seemingly entered autopilot mode. When she knelt before Anna and her "old flame," she only watched herself from above taking off both their pants and getting their cocks out. She felt like she was disconnected from herself as she alternated one cock for another in her mouth. She floated above the scene, unfeeling, serving her two masters.

The scene moved to the bedroom, and Cassie/Andy's consciousness watched it like they watched porn, absently behind the eyes. Initially, Anna and Cassie served the cock of the man together. Cassie even gave him a rimjob at his request. Then they spitroasted Cassie, with the man fucking her sissy hole and Anna deep in her mouth. Cassie hardly felt the pleasure at all, instead focusing on the memory that Anna had said to her that she only wanted Cassie to suck the man off while she watched. Yet here they were now. They stopped thrusting for a moment and Cassie realised she heard the sounds of them kissing above her, before they resumed their thrusting. Her dissociation only seemed broken by that one moment where she felt a tight pain in her chest, and she fully disconnected from her body.

Her memory only holds two more things of that night. One was the memory of Anna's mouth around Cassie's cage while the man fucked her ass. The next of Cassie laying on the bed, watching as the man came inside Anna's ass. He moved around and gave Cassie a kiss on the forehead before he moved to the bathroom. Anna said something to Cassie, as they both lay in post orgasm haze, but Cassie didn't remember what she had said. The man left when Cassie went into the bathroom afterward.

Cassie was dimly aware of Anna showering with her that night and Anna laughing at "how fun that was," which Cassie dimly acquiesced to. They fell asleep together, and Cassie left the next day for work, as Andy, completely on autopilot.

He knew something was wrong all day and desperately wanted to be near Anna. But she didn't reply to his texts promptly, and it made things worse. He began to get scared, and self-conscious, and hardly accomplished a thing at work. He texted Edwina hoping to talk about it but found himself unable to speak about his discomfort. He was supposed to be a slut, right? So why would he be sad and upset about what happened?

So, her self-criticism led her to suffer in silence. The next few nights her and Anna fucked but Cassie's heart really wasn't in it. Anna seemed to notice, but never said anything, acting distracted herself. Something was off but neither of them spoke about it.

A few days later, it came to a head -- Anna asked Cassie if she was alright to stay at her own place for a few days while she went away on a business trip. Partly, Cassie felt relieved, but she also felt panicked and clingy once again. Yet she said nothing, and Anna left.

Andy then shut down. Anna had left with the key to his chastity cage, but he was uninterested in sex. His libido was gone. All he did was sleep all day. He didn't become Cassie once or play with his ass. He barely texted anyone, even Anna or Edwina, exiting his room only for food. He called in sick to work multiple times and did little besides ruminate and mope. Essentially, Cassie and Andy were depressed. They doubted their worth constantly.

But they were still together in one identity, a sissy wholly, and attached to Anna. Which made it even harder when a text came through the day Anna told Cassie that she would be back from the trip.

"Cassie, I think I need a break from us." The text said.

Cassie found it hard to remember what she did after that. She remembered an ambiguous sense of pain, and she remembers what she replied over text, and was ashamed by it later. She begged Anna to stay, and Anna rebuffed her each time. Anna may have been a sub to the man a few nights prior, but she was truly dominant over Cassie in that moment at shutting her out. Cassie felt helpless as a result, and she cried for the first time in months.

This led to some more days calling in sick from work and living in a slump. Andy let his body hair grow back, something he hadn't let slip all the way since his first hook up with Anna. He wandered disconsolately around his apartment, continually avoiding his housemate, and did nothing but sleep. He doubted whether he was worthy to even be a sissy, to even be anything more than something to be tossed away.

Ash_P
Ash_P
90 Followers
12