The Acceptance of Cassie Ch. 01

He alternated this and shoving two hooked fingers up her ass to assault her prostate, which gave her a strong tingling sensation that she had replicated herself dozens of times in the shower. Her dick, locked away, leaked slightly.

The memories were, admittedly, making present day Cassie throb as she sucked her own dick, remembering the night and comparing the experienced to hers earlier in the present. Comparing this master to Anna. She kept replaying the memory in her mind, using the moments as motivation to cum.

The master then put his dick in a condom and tried to fuck her. He was worse at maintaining hardness when he wasn't being sucked off, and this disappointed her. He often went back to the dildo, roughly assaulting her insides, while he rubbed his half hard dick.

He made her get off the bed again and taste her ass on his condom covered dick. It tasted of lube, and nothing else, because she had cleaned herself well before she left home. The act felt kinky, but she wasn't into it, really being focused on survival.

When hard again, he slammed her ass for a while, but it was nothing compared to what he did to her with her own dildo. She was glad for the reprieve but was beginning to seriously consider her own limits. She had never done anything like this before.

"How about you go and get changed into your other outfit, sissy?" The master said.

"Peaches." Cassie said, suddenly becoming conscious, "I don't think I can take much more of this. Can you cum without me changing?"

It was as though the man was disappointed, but he accommodated her. "Can you suck me off and handle that?"

"Yes, I can. Alright, let's go back." Said Cassie.

He ripped the condom off as she knelt back by the bedside and resumed her position. He was no less rough, but after a few minutes, he came, one initial rope into her mouth, and the next all over her face.

"Clean it, sissy." He said, and Cassie licked the head disdainfully. She wasn't that into it anymore and Andy's shame was distantly encroaching.

He said nothing as he collapsed onto the bed. She crawled to the bathroom, and finally stood up, her knees incredibly sore. She caught a look of herself in the mirror, and having not cum, actually found her exhausted image incredibly hot. She had no idea how to clean her wig, but it was littered with ropes of pearly white cum. Her cage had some new precum on it. Her lingerie was surprisingly clean. She grabbed her phone from the bathroom counter and took a selfie in the mirror, smiling.

As she cleaned her makeup off and packed away her things, the door opened a bit and her toys clattered to the floor. It shut again without a word, and she wrapped them in her lingerie as she stuffed it all in her bag. She dressed again in her male clothing and having no other option but not really wanting one anyway, put on her panties again. She left the plug out though, her worries that her asshole was too loose to retain the plug overriding her horniness to walk out with it.

She exited the bathroom, a boy again, and the man said, "Thanks sissy" from the bed as he watched the TV. Cassie said a half-hearted "Thanks," and left.

The walk out of the hotel had her afraid that she would somehow be found out, but that was very unrealistic. She rode the lift down to the basement carpark where her car awaited, and she drove the whole way home, feeling the way her cage hugged her dick.

As Cassie, in the present, sucked her dick, she remembered the ungodly masturbation session she had at home following that hookup, removing her cage the moment she got in and inflating quicker than she could open her phone. Cassie remembered in the present that she had wanked to pictures of herself that she had taken in front of the mirror, focusing back constantly on the one she had snapped from just that night, as she got closer and closer to cumming after her session with that master.

Remembering that, Cassie pulled her cock away and used her hand to finish herself off. She came in her own mouth just to the memory of her past hookup and the masturbation after it. She even managed to swallow, today, feeling more accepting of herself than before.

In the clarity post-orgasm, she remembered waking up the next morning after her hookup. The man, still in Perth a few more days, messaged her "I bet that clitty is itching to get out of that cage today, sissy." Cassie never responded, and uninstalled Grindr.

That brought Andy to the present day. He installed Grindr AGAIN a week ago, for no particular reason other than that he was horny. He remembered being messaged by Anna, a faceless account, and doubting her realness. Anna sent many confirming pictures, including one with a handwritten note with Cassie's name on it, after they exchanged pics together. He even sent her that post hotel room hookup selfie with the cum in her hair. She said it was hot.

He had no intention of uninstalling again, now, in the present day. He was enraptured. He was less self-conscious than the other two hookups, but this time, he felt insecure. He felt like he wanted to see her again, but worried despite her affirmations, that she might change her mind about him. His insecurity threatened to overwhelm him with fear that he couldn't get what he wanted, and what he wanted was to be with Anna.

He was too exhausted to ruminate, though, and went to bed, a sloppy mess.

He wanked again that morning. Thinking of Anna, and Cassie, his own sissy identity. He thought of Anna all day at work and thought of messaging her. He had no idea what to say, feeling very doubtful. How would he talk to a trans woman, who knew him as a sissy? He never usually inhabited the role this long, as Cassie. But they were becoming one now.

He wanked again when he got home, in the early evening, looking occasionally at the selfie of Anna and Cassie together as he read his favourite cross-dressing hentai manga. His wig and clothes now sat in their usual box, as he was naked following the day's work. His thoughts constantly returned to her. After 20-minutes of edging, he opened the contacts app on his phone, hoping to ride the horny wave to action, because it was so easy to message Anna the first time with one hand on his dick.

He found the contact and looked at it for a solid minute. Anna Cassandra. It took him that whole minute, still stroking his dick, to click the "message" button.

He was surprised to find a message that had already sent. It just said "Anna Cassandra."

What? He thought. When did I do that?

The rational reaches of the sissy brain activated, though, and he realised Anna texted herself when she put her contact in so she would have HIS number too. That was a dominant move!

And as if on cue, he received a text. It was uncanny timing. He saw: "Hey there Cassie. I loved last night with you. I hope you still remember me. Do you remember what you left at my place? Come pick them up soon?" Appear right in the page he had opened on his phone, seconds before.

Three dots. Waiting. Cassie had stopped stroking herself.

A picture of her silicone butt plug sitting on her pink panties came through. Cassie sat wide eyed, staring at it. A moment passed, and she laughed at it, moved her other hand to her phone, and began to type with both hands.

I can't wait to spend more time with that cock. She thought, as she typed out her reply.

To be continued in Chapter 2: Friends.