1. Sissy Riley: The Dream Of Las Vegas. PT 1. Gooning, Sucking And Cumming


    Date: 9/17/2023, Categories: Cross-dressing, Author: tattooguy112

    John had finally done it. He had started an online self-sustaining store that would help him quit his 9-5 job. He was only a few weeks away. This store would help John focus on something he had always wanted to give time and effort to, becoming a Sissy. John, for the better part of five years, had two lives. The one where we got up in the morning, put on a suit, and worked a stressful job and his nightlife, where he would become Riley, put a chastity cage on his cock, put a thong and a girly nightgown on, get high, suck on dildos and goon her mind out.
    
    John had been focusing his evenings the last six months on creating a self-sustaining online store so he could quit his daytime job and focus on being a full-time sissy. It was something he had wanted to pursue more intensely for a long time, and now that time had come. To celebrate, John got started ordering his new sissy wardrobe, some new toys, makeup, his edible order from the dispensary down the street, and most notably, his magic mushrooms were ready to be picked.
    
    John had decided he would resign on Monday morning. He would wake up, cage himself, put on a thong, and throw his suit over. That evening, he would start referring to himself as Riley and start working on his next goal of being a sissy. Riley’s dream was to fly to Las Vegas, get a room for four or five days, and set up a glory hole where she could dress up, suck cock, have men cum on her face, and have her ass pounded and filled like a good little sissy ...
    ... slut. It was her ultimate fantasy and now it was time to make it a reality. She wasn’t ready yet, but now she could start focusing on this reality.
    
    Monday morning was here, and it was time to quit the day job. Just the night before, the online business made ten thousand dollars. Knowing it was the right time, John took action. John awoke, turned on the coffee and shower, and went into the closet to pick out his suit. John picked out the suit, put it onto the bed, then went into the shower. It would be his last one as John for the day. John stepped out of the shower and dried off. He went to his chore and took out his chastity cage and thong. John’s cock grew hard in excitement, but knew he needed to gather himself to get the cage on. After a few minutes, the cage was on and locked. John slid the thong on and put his suit on.
    
    He grabbed his coffee, sat on the couch, and opened his phone to see where his orders were. He was very pleased to find out that his new toys, clothes, and makeup would all arrive today. Tonight, Riley would celebrate by being a filthy slut.
    
    John finished his coffee and made his way to work. His cock was hard and starting to leak. The cage and thong were making him excited to get back home and indulge in becoming Riley. He thought about the evening she was going to have, the sissy porn and music that would be on, the outfit, the dildos, the drugs, the orgasms, it was going to be a fun filthy night.
    
    John arrived at his work and took a few minutes ...
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