The Acceptance of Cassie Ch. 00 - Prologue

The Acceptance of Cassie

Prologue - Anna

As Andy, or was it Cassie, felt the third penis he had felt in his lifetime enter his mouth, a startling moment of clarity bloomed in his mind. Maybe it was the fleshy, warm head pulsing against his tongue that brought on the clarity of his existential question. Or the idle imagery of the cock, hopefully soon, pushing up against his brainstem, blocking all thoughts. Making him hopelessly drunk on the pleasure of it, though he still shuddered at the shame of the thought. The sensation of that pulsing, thick, and tangy dick entering his mouth that made him wonder: how on Earth did I end up here?

As if in answer, a rebound in his mind occurred. I am Cassie. I'm going do what I've been wanking to for so long. I'm going to own it, this time. This is nothing like the other times.

Acceptance bloomed in her mind as Andy became Cassie, as they became one, and he assumed the submissive role fully for the first time with someone else. Now, fully Cassie, and not just by himself in his room, watching porn.

After that split second of hesitation, Cassie created a vacuum with her lips, and began to suck on the tense head. A moan from above her sounded to reinforce her choice. A hand stroked her exposed boy hair from behind and pushed her deeper, but not forcefully. Cassie continued to suckle on the head, savouring the faint salty tang. The tang told her the dick had been washed perhaps before its owner had left the house in the morning, but it had now become salty inside its foreskin all day, inhabiting the red panties that now sat discarded on the floor.

She knew the taste of a dick made unclean by a day on the town solely because her talent, that nobody else knew, was to suck her own dick. She could just get the head in, but it was enough. She could suckle on that head for only a few minutes and unload hot cum right into her own waiting mouth. It was usually in those moments where she became Andy again, spitting the fluid out in a moment of shame, wondering why he keeps doing this. Those were all thoughts for another time, though. She was here now, and she was sucking a new cock, though it tasted not unlike her own after a day at work.

This new dick belonged to Anna, the stunning trans woman that had opened her door moments before to Andy's startled eyes. She had flowing brunette hair and hazel brown eyes. When she opened the door into the quiet apartment building, minutes ago, Andy wasn't even dressed as Cassie yet, and he felt like an insecure boy staring at a beautiful woman. Anna had taken one look at him in the doorway, smirked, and beckoned him inside. As he took a step in, he took in the odour of her apartment, smelling a hint of incense. She looked like she had been out that night, wearing an olive clubbing dress that highlighted her slim figure. She was thin, with only a faint hint of curves. She was taller than him, perhaps by two inches. He was shocked, mostly that she was real, and secondly that he was here, meeting a real trans girl on Grindr. It was like everything that led to this moment had been a dream. He snapped to reality as she gently clasped his hanging hand and pulled him into the apartment's small entryway with no ounce of hesitation.

"So, Cassie," she had said, as Andy had the sudden realisation that he was indeed Cassie on Grindr and needed to get his head into it and stop being anxious, "the bathroom is your safe place here."

Andy was lost for words, feeling too unsure to even speak. He worried that his voice would be too obtrusive, too manly, too fake even, for the dream that was staring him in the face. So he remained silent and nodded.

"You can go in the bathroom any time and know I won't bother you. Take all the time you need there." Anna said, as Andy heard the front door shut behind him, and he took in her apartment around him. The blinds were shut, barring view from the neighbouring building. To his right, immediately through the door, was a dark, clean kitchen. A wine glass sat in the sink, and an empty white wine bottle sat on the countertop. A few paces in front of him was a small living area, lit by a small lamp on a bookshelf. A pink rug was thrown over an ikea couch with an incense burner smoking on a coffee table in front of it. A TV faced the couch with porn paused on it -- it appeared to be a pegging video. It had paused with a shemale lying on her back, one leg raised, as she was pegged by a tattooed woman wearing a harness sporting a reasonably sized purple dildo. The dildo was frozen halfway inside the ass of the shemale.

"Fuck, I'm glad I got you to come here tonight. Do you need to dress right away? The bathroom is just there, through the sliding door," Anna continued, motioning to a closed sliding door adjacent her open bedroom door, as she led him into her bedroom. She had a warm yellow light on her bedside table, illuminating a baby blue bedspread with some patterned pillows against the headboard. There was a dildo sitting on a bedside table, with a box of condoms and a bottle of lube alongside it.

"I'm already hard. You're such a cute boy." She said, shutting the blinds of her bedroom window. He briefly saw the lights of the building parallel's balconies and windows before the only light remaining was her lamp, and all he saw was her back, in her olive dress, as she turned back to face him.

Andy stumbled for words again, looking awestruck at her as she pulled her olive dress up and revealed some red cotton panties. She shimmied them down to the floor, and he saw they were patched with gooey translucent liquid that could only be precum. His eyes lingered a little too long on the panties, knowing in his mind that a cock now waited for him to look at. He shifted his gaze slowly upward toward it, Anna's hand already there, nursing the half erect penis to full stiffness. It looked to be of average girth, somewhat thicker than his own, and around as long as his. Maybe his imagination told him it was longer than his, but he couldn't be sure. Anna's penis reminded him of Aubrey Kate's dick. She was always one of his favourite pornstars.

Anna reached out to him, grasped his dangling hand with her fingers, and guided his hand forward to touch her dick, too. He followed along, a little stiff and nervous in his arms, and touched the gelatinous, fleshy mass of her hardening dick. Feeling another penis always felt so strange to him, he thought, as he ran his hands along its warm length. It always felt so much spongier than his own, though he knew his to be the same. Only it seemed he forgot what other dick felt like when he spent so much of his time just playing with his own. Anna's was uncircumcised, like his, and unlike the last two men's dicks he had had before. It was warm in his hand, and her hand was reassuring, guiding him along her shaft.

"How many dicks have you had before, Cassie?" Anna asked, curiously, helping him stroke.

"Um, two." Andy said, stiffly.

"Not bad, are you ready to make it three?"

Andy, scared and excited out of his mind, though noticeably less so than his first two times, slid off the backpack holding his clothes and wig for Cassie's outfit. He placed it against the wall of Anna's bedroom, next to her mirror, and returned to her standing resolutely, cock pointing outward, ready for him.

He knew what to do from the porn. He knew how the men acted that he watched with trans girls in the countless videos he had seen. He had dropped to his knees, her cock in front of her face.

And that brought us to the present moment. How did I get here? A cock in his mouth, becoming Cassie, and not even dressed as her yet. He had just begun to suck, and Anna's hand grasped the back of his head, kneading his scalp.

Cassie, now fully in the moment, continued to suckle on the head, before raising her hand to fondle the balls.

"Mmm, Cassie, you know more about this than I thought you would!"

Overwhelmed at the praise, Cassie redoubled her efforts, dancing her tongue along the frenulum of Anna's dick. She always loved doing that to herself when she sucked herself off.

"Oh my God, Cassie I thought you'd only had a few!" Anna laughed, as Cassie continued her work.

Cassie, now overjoyed at the praise, bobbed her head up and down on Anna's tasty cock. Cassie brought a hand into the mix, gripping the base of Anna's shaft, working the head with her lips, and flicking her tongue on Anna's frenulum. Anna groaned in response, and Cassie attempted to take her as deep as she could. She surprised herself at being able to hold her deep in her throat, not quite all the way to the balls, for just as long as she practiced with a dildo.

She receded and continued her hand work, before Anna chuckled, "Stop, stop, you'll make me cum! Let's just edge this one and I'll let you go dress! I want to see you transform."

Cassie pulled her head back and looked up at her, smiling, before Andy kicked back in and stopped the smile. Anna reached a hand down and ran her nails along Andy's cheek.

"Go dress nice and quick, I'll wait. But don't be too long!"

Andy scrambled to his backpack, turning his back on her without a thought, and hustled to the sliding door. Some thought deeper in him wanted her to see less of him as a boy, as if there were protection and solace in the guise of Cassie. The bathroom was dark as he fumbled around looking for a light switch.

"Light switch is just outside!" Anna shouted, glee on her tone.

Andy found the switch and flicked it on. Inside, there was a douche standing by a white sink surrounded by feminine beauty products. They were all surprisingly organised. A butt plug, metal and bejewelled with a faux emerald at the end, was on the other side of the sink on a towel.

He snuck a glance at himself in the mirror. He felt some shame, as before, but it was more numb now. He smiled at himself in the mirror, and it hit him. He felt excited over the nerves. I've been wanking to porn like this for so long. Now I'm really here.

So, he set about his work. He opened his backpack and took out his blonde wig and wig cap sitting on top and set it aside. Next, his pink lingerie set, set aside next to the wig on the countertop. Last, his makeup bag, which he set front and centre.

He took off his boy clothes and packed them back into the empty bag. He took off his girly pink panties that he wore underneath and set them aside. He opened the front zip pocket of his bag, removed a silicone black butt plug with a bottle of lube. He lubed it up and gingerly inserted it into his pre-washed anus, Cassie chanting in the back of his mind, plugged sissy! He scoffed to himself, embracing the moment, all those sissy hypno videos playing their message back in his mind. He loved the practiced way the plug had entered him, filling him up. The plug used to be his solitary companion for his closeted masturbation sessions. But not tonight. Tonight, he'd show someone else his toy. He flexed his sphincter muscles a few times, wrapping his awareness in that ephemeral discomfort, yet pleasure, caused by the stretching of his bussy by the plug. He loved being filled.

As he slid the panties back on and began putting on his white stockings, he felt the plug shift in his butthole, and his watch beep, meaning it was now 12am. He realised now that Anna must have been out clubbing when she messaged him. It was lucky he wasn't asleep, that he was awake idly watching Netflix. He completed his outfit as he contemplated where she could have been, out on the town in Perth. Such a boring city.

Where could she have been?

That just left makeup and wig. He did his makeup first. It didn't take long -- he could do it fast when he was washed over with a wave of horniness at home with a night to himself. Foundation, then toner, then eyeliner, then eyeshadow. That was how he did it. It was basic, but as he looked in the mirror, he thought to himself, damn, I'm happy with that.

Then, as he fixed the wig cap over his boy hair, and settled the blonde wig on top of it, he thought: Hello Cassie.

Cassie slid open the door to the bathroom, light spilling out behind her. Anna looked up, porn sounds coming from her phone, as she stroked her thick cock. She was naked on her bed. She had barely any boobs, maybe an A cup. Her nipples were perky, surrounded by soft looking areolas. She was slim and fit of build, and her brunette hair cascaded down her slim shoulders, showing her collarbones. She reminded Cassie of Domino Presley, without the curves, and taller.

"Hello Cassie, don't you look like a honey," Anna said, salaciously, locking her phone, "I actually prefer it seeing the boys first. I love seeing the difference as you embrace this beautiful side of yourself. And you are beautiful."

Something tingled inside Cassie. Something deep, primordial, and warm. She felt validated and seen. No man had given her this. Or woman. She felt compelled to kiss Anna, to be taken by her, to be cared for. To pleasure her.

Anna saw the longing in Cassie's eyes and thrust her tongue right into her mouth. She tasted like white wine and sweet lollies. Anna hands were around Cassie's ass, caressing her, tracing her spine, grasping the back of her neck. Cassie's own dick throbbed against her pink panties, out of mind.

Anna pulled away. "Can I ask you to suck me a little more, Cassie? Just a little warmup, nice and gentle please."

Cassie said nothing, just obliging, as she knelt.

"Cassie, you can speak honey. I want to hear your voice."

"Oh," Cassie started, not being used to this, "I'd love to suck you again."

Cassie noticed a feeling blooming in her chest. She wasn't used to this role -- she was used to either taking the lead with girls, in her boy role, or being told exactly what to do, with men. And used to being told to shut up, or press her face here, or degrade herself like this. She wasn't used to being checked in on, or being desired like this, even submissively. She liked it. A lot.

Anna pushed her cock right up to the tip of Cassie's nose. Cassie took a deep pull of her musk, the eye of the penis just touching her nose, and came away, a rope of precum stuck to the tip of her nose. Cassie then lifted her chin, and she licked the tip of Anna's cock. She alternated between slow licks and some loving, slow, bobbing sucks. She licked Anna's smooth balls often too. Anna moaned softly along for the next few minutes as Cassie lovingly worked her magic. Her sissy magic.

Suddenly, before Cassie even got to work with vigour, Anna stopped her moaning, pulling her cock away and motioning Cassie to stand with her. She kissed Cassie deeply, passionately, the alcoholic taste of her intoxicating.

Then SHE knelt in front of Cassie! Cassie was shocked, so much so that she didn't make a sound as Anna lowered Cassie panties to reveal a decent sized penis, perhaps 5.5 inches, in a throbbing erection. Cassie stepped out of her panties, and Anna tossed them aside.

"You have a lovely cock, Cassie. Would you let me suck it a while?"

"Um, if you'd like to!"

"Of course, honey." Anna said, taking Cassie slowly in her mouth.

Cassie moaned in as girly a way as she could as Anna took her. Anna tickled her balls, licking her frenulum just as Cassie had done to her before. Cassie squealed in a tone that surprised her in the moment. Anna continued in her gentle way for a few minutes, until she ran her hand along her gooch and encountered a plug there.

Anna removed her mouth from Cassie's cock. "Oh! I didn't know we were expecting anal. Is that what you wanted? I was just going to finger you a bit, I didn't expect you to be plugged!"

Cassie was shocked again, for what felt like the hundredth time. She thought anal was expected.

"I, uh... I'd love you to fuck me." Cassie loved her own tone. Deep down, she wanted this. A fucking lot.

"Then I would love to fuck you," Anna said, looking up at Cassie's tantalising eyes, "Let me just get a condom ready."

Anna stood again, and walked to her bedside table, taking a condom, throwing it onto the bed with the bottle of lube. She stood and stroked her cock, looking at Cassie doing the same.

"You know, I thought we'd just suck each other off and that'd be that. But you're full of surprises Cassie. Care to join me on the bed?" Said Anna, motioning Cassie over.

"Sure!" Said Cassie, nervously excited.

Cassie crawled onto the bed, unsure of what position to take. Anna watched her curiously as she slid a condom on her dick, then lubed it, all the while watching Cassie uncomfortably sit, then kneel, then look disconsolately at Anna.

"Before we start," Emma said, "Can I ask what you other two dicks were like? Were they Grindr as well?"

Cassie started. She wasn't expecting this. Some negative flashbacks came to her, and the expression on her face seemed to paint enough of a picture for Anna.

Anna continued looking curiously at Cassie. "Yeah, they were Grindr. And they weren't great." Cassie said, the boy in her showing through in the words.

Anna seemed as though her suspicions were confirmed, as she smiled like a person who was proved right. She held out a hand to Cassie, which Cassie took, and Anna pulled her in close.

Anna kissed Cassie, that deep, tongue infused way, and pulled away.

"Oh Cassie, you haven't been getting enough love honey."

There it was in Cassie again, that primordial warm feeling. It meant being cared for, validated, and appreciated. She felt worth something, to this beautiful woman with a cock. Worthy in both her forms.

"I'll give you some loving now, if you still want it. It'll be easiest if we go doggy to start, okay? Just kneel in front of me."

Cassie eagerly moved to place her ass in front of Anna's body. She looked behind her to watch Anna assume a kneeling position and slide her hands up Cassie's back. It felt electric to Cassie. Anna shifted Cassie's lingerie up her back and moved a hand to Cassie's plug.

She slowly wiggled it, by the hilt, and began to tease it out. Cassie let out an involuntary groan, and Emma breathed out on satisfaction. She then wiggled the plug a few more tantalising times, before PLOP, it left Cassie's boy hole.

"Beautiful," Anna said, before kissing the plug, and putting it in a tissue on her table. She grabbed the bottle of lube and put some on her fingers.

"Cassie, I'm going to fuck you now. Are you ready?"

Cassie broached a little, and arched her back, just like she'd seen in all the porn videos. Just like all the sissies and trans women she idolised. It was time.

I have been here before, but this is so different. She thought.

"I was born ready." She said, summoning all the seduction she had into her voice.

"Fuck, you are so hot" Anna said. She pressed her fingers into Cassie's hole, feeling cold. Cassie made no noise as she removed them and heard the crinkling sound of Anna massaging the lube onto he condom covered dick. Anna then pressed the head of her beautiful dick against Cassie's open butthole.

Cassie's mind entered a new plane of existence then. It anchored itself in true pleasure, and time lost all meaning. This woman was everything. And Cassie was where she always wanted to be. Shame seemed to leave her body entirely as Anna began gentle thrusts when her cock effortlessly slid past the initially tight gateway made loose by Cassie's favourite plug.

Anna was slow and caring. Nothing like the other two cocks. She hit all the right spots with ease. Cassie's mind was utterly gone, lost in pleasure and positive validation. This is how it is supposed to feel, she thought.

Only a few gentle minutes of easy thrusting passed, with Anna and Cassie's moans mingled in the room, before Anna's voice broke the ecstasy: "Oh no, Cassie, I'm sorry, I've had a bit to drink and I am so close. Can I cum?"