The Acceptance of Cassie Ch. 01

The Acceptance of Cassie

Chapter 1 -- Memory

Andy didn't sleep well the night after he met Anna. He drove home in a daze, as if dissociated, unable to believe the life he now inhabited. Yet it was real, he accepted, as he sat at the final red traffic light before home. He glanced over to see his backpack in the passenger seat, holding Cassie's clothes, and he became sordidly aware that the skin in between his ass cheeks was still slick and moist with lube. He drove for 15-minutes before parking at his apartment, every movement of his ass causing his hairless butt cheeks to slide against each other. Some part of his mind thought that if he could get inside home, he could integrate the almost unreal feeling evening he just had into what he thought his life was before. That life could somehow be normal again.

While exiting the car and riding the lift to his apartment, he wondered for perhaps a few moments what would happen if anyone in his personal life ever found out what he had done. Those thoughts didn't last long.

Horniness already had a vice grip on Andy before he was in the door. Thoughts of normality had fled to be replaced with hot, licentious musings of dick. His roommate was definitely asleep in the other room across their living room -- it was past 1am. Andy practically flew into his own open bedroom doorway, quietly shutting the door behind him. He flicked on his bedside lamp. He was opening his bag, pulling out the wig, getting naked, and putting it back on his head. He didn't even bother with the wig cap to full cover his boy hair.

Before a minute had elapsed, a naked, blonde girl called Cassie was on the floor, legs over her head, her cock hanging over her own face, erect and dripping. It smelt of fresh cum pushed under foreskin. It took her a moment of stretching to have the head in her mouth, tasting the salty tang of her own dried cum. Her mind lingered on another cock though.

She brought her cock out of her mouth, stretched back out, and scrambled to find her phone. It lay on Andy's bed, next to the open backpack, low on battery and unlocked in an instant.

Cassie's legs were back over her head a moment later. She took a position with her arms flat on the floor, so she could raise one hand to push her butt cheeks so that her groin would come down into her mouth, with her other hand holding her phone, displaying a picture just in front of her eyes as she sucked at the head of her own cock. The phone in front of her displayed the picture of her and Anna.

She suckled her cock as she studied to picture, noticing parts of Anna's features that she hadn't recognised before. She had some freckles under her eyes. Her lashes were natural, and her brows were delicately trimmed. Cassie envied her look but marvelled at her own too. She knew she looked shocked, more shamed than excited, but she enjoyed the way her boyish face gleamed. She looked fresh from sex and hotter for it. She loved it. There were masculine bits here and there that needed work -- something about Anna's eyeliner, and her makeup, just made her so much more strikingly feminine than Cassie. She needed to learn how to attain at least some of those goals, she thought.

Having just cum so powerfully within the hour, Cassie wasn't quite ready just yet to cum again. She was hard as ever but needed some time. She directed her thoughts back to the events of the night, turned on. But then, without her control, her mind wandered to the first two times she had tasted strangers' dicks before.

She remembered the first time. She remembered messaging the guy on Grindr a few weeks after Andy broke up with his girlfriend. It was a rough breakup and it hurt Andy badly. They were together for around a year. It was Andy's first serious relationship, too. But Andy knew that the relationship was eating away him, toxically, and it wasn't good for him. During their relationship, he still happily masturbated often, even occasionally seeking sissy porn. His girlfriend also pegged him once, but she didn't like it. He was also a bit uncomfortable, but he wasn't sure if it was her discomfort, or his, that caused it. The experience felt jarring, like his girlfriend didn't want it, and they never tried again. He still had the strap on somewhere in his wardrobe.

Andy had sought out all kinds of porn before that relationship began. He had come to porn from such a young age that the vanilla stuff got old when he was already just a late teenager. He was onto hentai before he was 16, and from there, he came to futanari, having seen it advertised on a hentai website as a mysterious category. After falling in love with girls that had penises, he became curious for the pleasures of anal. He then branched out to shemale porn, then shemale and male, and stayed there for years. He would sometimes explore his ass in the shower and came easily to the feeling. But it wasn't just the feeling he liked -- it was the uniqueness, and the underlying covert sneakiness that came from breaking the masculine mould. He liked the idea of being the one who was fucked, not always the one doing the fucking. He loved seeing the boys in bliss as they were fucked silly by futanari beauties, or by shemales in the real porn.

The logical progression then took its course. Hentai, to futanari, to shemale, and finally, to sissy. He was in his early twenties when he first encountered the intoxication of sissy porn. He had moved out of home the first time in that period of his life and ordered his first set of toys with little hesitation. He explored his ass with renewed vigour and frequency. It had ushered him into a new age of wondering about not just what a shemale's cock would feel like, but perhaps a man's. The progression took a few years, with his internalised shame and homophobia often taking hold, but the allure of pleasure always overrode it, and brought him skulking back to wondering what another cock might feel like.

And how he might feel as a sissy.

When he first experimented with online shops for lingerie and wigs, he met his ex-girlfriend, and he stopped wanting to be the girl and enjoyed being with the girl. Such was the course of his sexuality. He stayed this way for a year, while in the throes of a positive straight relationship, with underlying toxicity that eventually was its downfall.

Around the time of the breakup, Andy had been off sissy porn for a while, seeing it as shameful, and was looking at shemale porn almost exclusively when he did masturbate. He hardly ever looked at straight porn. A few days after the breakup, though, he drifted back to sissy porn. In a matter of days, he had taken a leap and ordered a wig and his first set of lingerie -- the same pink set he wore to Anna's place. All he needed was the extra motivation of having no one to accidentally discover his fetish. The loneliness caused by his breakup aided his growing motivation to be validated outside his old role in his broken relationship.

He trialled Grindr, and the attention as lovely. The validation was good when he felt low. But he felt awakened -- there was something intoxicating about sending men the photos of him dressing and have them respond so affirmingly. And often degradingly. He slowly grew accustomed to the constantly horny vibe of hairy men and refreshed his phone often for their notifications. He never realised he could be so turned on by dicks that were hard for him.

When they asked for face pics, he usually ghosted them, and continued leading a masturbatory existence. But soon, he ordered makeup from Kmart online. He trialled it, and that was the moment he settled on a name. He used just "A" on Grindr before. And now he would use Cassie, the 23-year-old non-binary sissy seeking men and women. Cassie's horny cycle continued for some weeks, with Andy playing dress up, buying more clothes, and experimenting on weekends with makeup when his roommate left for the day. He would spend his hours taking photoshoots in the bathroom and sending them to horny men.

After a month with Grindr, with Andy masturbating nearly three times daily and constantly checking for unsolicited but welcomed dick pics and propositions from men while he was at work, he took the leap. He finally found a man who could host and offered openly and quickly. He promised to meet him that night. The man gave him an address in West Perth. Andy fretted about someone he knew seeing him but challenged the thought as unlikely. He really wanted to experiment with a man. He did an enema when he got home, making sure to be thorough, and shook nervously as he emptied it each time. He remembered leaving home in a baggy jumper, shorts, and a plain hat.

The arrival was awkward. The man told him to change. His apartment smelled filthy, and it stunk of cigarettes. If Cassie expected an alpha, she found a beta. Or so the sissy content would agree. Cassie remembered shaking nervously in the smelly bathroom as she changed. It wasn't filthy -- it just smelled like nobody had opened a window in a long time. Her cock softened as she remembered the odour, still sucking herself off in the present, remembering her past.

When she emerged from the beta man's bathroom, dressed in her wig, a silky nighty, and knee-high socks, the man leapt from his bed, and motioned to his hard cock.

"You can suck it if you like." He spoke.

Cassie and Andy were half and half in the mind at that moment. Doubtful, but still curious to try to experience. Having masturbated to sissy porn for so long, there was no going back now. So, she knelt, and took the half-hard dick in her mouth.

It tasted like nothing, ironically, compared to his apartment that was full of all the wrong kinds of smells. His moderately sized penis was perfectly washed, which was, she supposed, nice, but she hoped for some sort of taste. One part she did like, though, was feeling it fully harden in her mouth as she bobbed upon it.

The man had her on the bed quickly, asking her to get up there. She nodded and hummed "Mmm," afraid to speak. He unwrapped a condom as she sat there, ass up, waiting for him.

He took ages to find her actual butthole, strangely. It was like he wasn't even looking, pressing his condomed cock into the skin above her anus. He fumbled around like an inexperienced virgin, though he was definitely older than Cassie. When he slid fully in, she found a moment that she adored in the otherwise lame experience. It was the positive she often looked back on. The sensation of him entering her felt like pooping, but in reverse, and when she relaxed, and let him thrust deep, it felt like he pushed against the base of her spine. It felt unbearable, but in a good way. His thrusts replicated the sharp, spinal feeling, and she enjoyed it. He touched her cock once during the sex but pulled his hand away. She expected because it was soft the entire time.

He didn't last long at all. He groaned and finished in her, but she only felt one or two clenches. She expected he had masturbated before that day and had little left in his balls. She didn't know what to say, as he stumbled away, ripping off the condom and fleeing to the bathroom. She wouldn't meet his gaze when he returned and mumbled a "Thanks." Before he said, "You can use the bathroom now."

When Andy re-emerged, dressed in male attire, they said a quick thank you to each other, and Andy left. He remembered going home and wanking to the memory while watching sissy hypno, having never gotten hard the whole time, but instantly erect when home. He wondered if it were the hypno, or if he weren't into it. Either way, he uninstalled Grindr, but kept wanking to sissy porn.

Life went on. He usually missed his girlfriend and felt lonely. He saw friends, went to work, hung with his housemate, and played videogames. It was mundane, and it was his life, as Andy. He told friends he would stay away from Tinder for a while, never saying that he was going home every night to wank to hentai, sissy porn, shemales, and gender bending literotica.

It was three months later when he had his second experience. All those months saw him expand his collection of many clothes, a douche, and one modest butt plug to three dildos, two more plugs, a prostate massager, and three chastity cages. He had no more girlfriend to spend money on, so he justified the spends, and messed up the size of his first chastity cage. It was too big, he discovered, after spending an hour trying to get it on while getting erect all the time. He didn't cum for seven days, trying for the elusive sissygasm, in that oversized cage. He eventually caved and came all over himself, pulling out of his mouth during autofellatio at the last second.

The second cage was too easy to get out of, and the last was a perfectly fitting pink resin one. It looked so perfect that Cassie felt compelled to show it off, and not just to five upvotes on reddit that she initially received. So, she returned to Grindr.

Her new wardrobe and makeup skills shone through, and she had more male attention than ever before. She settled on a man staying in Perth for a business trip -- he was only in his late twenties; unlike the older man in his thirties, whom she had seen before. She ran no risk of her hookup knowing anyone that Andy knew, because he was in a hotel, and only briefly in Perth.

They met up at 9pm on a Thursday night. He told her to bring some of her favourite toys, wear her cage, be plugged and wearing panties from the start, and gave her some specific instructions.

"Wait in the lobby. I will come down and collect you. Look at the ground, do not make eye contact with me. Walk in front of me, and I will tell you when to enter the door. The bathroom is where you will get changed. When you exit, crawl out. You may not stand unless told to. If it gets intense and you say the safeword, 'Peaches,' I'll stop. Say yes master if you understand."

"Yes, master." Cassie replied.

In the present, Cassie sucked her cock with one hand on the shaft as she was enveloped by the memory of standing in the hotel lobby, waiting for him to come out of the lift. She had put her phone down and was no longer looking at the picture of Anna, instead focused on pleasuring herself while remembering her second cock.

The hotel where she was to meet the man was surprisingly busy, which made her more nervous. After 5-minutes or so of waiting, he came out of the lift, wearing a thick Kathmandu jacket and jeans. He looked young, with some facial hair, and seemed to be Asian, though she avoided looking at his face as instructed. He was as tall as Cassie. He nodded to her, and she followed him into the lift, along with an elderly couple. Cassie stood in front of the man, with the couple nearest the doors. The elderly couple got off 2 floors before them, never the wiser. As the couple walked out of the lift, her hookup put his hand down the back of her pants and felt the plug and panties.

"Good." He whispered in her ear. She felt excited and nervous at the words, but also somewhat worried about whether this was what she wanted. They walked down the ninth-floor hallway, him guiding her with an Australian accent and a gruff tone. He opened the door for her and bade her enter the bathroom that was on the immediate right as she walked in the door. He shut the bathroom door immediately behind her, saying, "Come out only when you're ready. Don't forget to crawl."

She got dressed in the pristine hotel bathroom and unpacked her toys. She withdrew her favourite dildo, her vibrating plug, a container of lube, and a condom for him. She dressed in a black set of lingerie that he chose from her pictures of her collection. She also had a second set of lingerie, because he told her to bring two, in case she wanted to change halfway through. She made sure her plug and cage were secure -- her cage glistened with some precum on the resin exterior but her dick itself didn't appear to be actively leaking anymore.

She opened the door and crawled out. He was still fully clothed, and she avoided his gaze.

He stood in front of her, still fully clothed, and said:

"Kneel, sissy, you know what to do."

She knelt, but before she could raise her hands, he thrust her face into the crotch of his jeans, rubbing her nose all over it. The jeans felt rough, and she felt her makeup smudge. He told her to sniff, which she did, and his pants smelt hot and manly. Not a smell she really expected, though she didn't know what to expect.

"Undo my belt" he said, which Cassie obliged. She felt somewhat afraid of him, and handily reminded herself of the safe word, reminding herself he had been accommodating there. She slid his pants down, and he stepped out of them, revealing grey Bonds underwear.

He pressed her face the same way into his underwear, the sweaty and manly odour stronger now. She felt his dick bulge there, noting a strong curve in it. She had seen that in the pictures, too.

"Remove my underwear, but you are not to use your hands, sissy. Not unless I allow it."

She did so, using her teeth, cringing slightly at the smell that came through her nostrils as she pulled the underpants down with her mouth and his cock slapped her face.

The underwear dropped and the man thrust Cassie's face straight into the underside of his shaft with his hand on the back of her head, her nose plunging into the flesh of his balls. She was feeling used and abused, but she thought that maybe this what being a sissy meant. The skin was fleshy and sweaty, with small prickly hairs all over it. Where her first cock had little to no smell and no hair, this had too much smell and hair for her.

"Alright sissy, you know what to do now." He said again.

She moved a hand up to stroke his shaft as she prepared to take him in her mouth, and he smacked it lightly away.

"Sissy, I told you not to use your hands. You'll be punished for disobeying"

He grabbed her head and thrust his cock right into her open mouth, triggering her gag reflex, and causing her eyes to water. He held her there for a moment, and she thought she would vomit. She grasped at his hairy leg, and he released her.

"No more hands, sissy. Now suck."

She swallowed, made so uncomfortable so suddenly. She felt out of her element before and now felt fully under his control. She considered for a moment "Peaches", but something neither Andy nor Cassie said that now they were here, they may as well commit. Maybe it was both of their tendency to follow through with everything they committed to. It was why they were here in the first place.

She then received the roughest tutorial of a blowjob she had ever received. She didn't expect to gag or come so close to vomiting so many times that night. She expected to not experience that once. But she kept going, determined to win somehow. To survive this humiliation.

Partway through the blowjob, he ordered an inspection of her plug and cage. He fondled her balls and told her she had a cute sissy purse. He pulled out the plug roughly, making Cassie gasp, and replaced it. Then he did it again a few more times. He removed it one more time and ordered her to fetch her toys.

"Don't forget to crawl, sissy." He spoke.

Andy and Cassie seemed to work in tandem that night, surviving together. He made her sit on her favourite dildo almost to the hilt as she continued to suck him off, being made to go deeper and deeper, finally to the balls, watery eyed. She dreaded each new order to go deeper but held it at his orders.

Relief flooded her when he told her to get on the bed, and the dildo left her ass. He told her to lay on her back, her ass near the edge of the bed. He put a pillow under her hips, and then fucked her ass with her own dildo roughly and deeply. She wasn't sure what had been more painful. Yet some morbid part of her enjoyed some of it, even still.