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 in his car to compose himself. He got out of his car, went into the building, and sat down at his desk. Over the past week, he had been slowly moving his things from work to home. He only needed to take a few more things. John waited at his desk patiently. He finished off a few loose ends and made sure there were detailed instructions for the person who was going to take on his work on what to do and what needed to be done. As John finished up he got a notification on his phone and he knew now was the time. His delivery had arrived at his home.

John printed off his resignation letter and walked into his boss’s office with the letter in hand.

John cleared his voice, “Mr. Johnson, I need a few minutes of your time.”

Mr. Johnson looked up at John and saw the resignation letter in his hand. “John, I hope that isn’t a resignation letter in your hand. You are a fantastic employee and would hate to see you leave.” Mr. Johnson said it was like it was an auto-recording.

“Mr. Johnson, this is my resignation letter and it is effective immediately. I appreciate the opportunities you have given me, but I am going on a different path. I have left instructions for whoever will take over my work and things that still need to be accomplished.”

John was trying not to sound excited and remain professional, but it was coming through. Mr. Johnson reached out his hand to John. They shook hands, Mr. Johnson notified HR to send his last check, and just like that John left.

John got back to his car, took off his jacket, and put it into the backside along with his tie. He sat down behind the wheel and screamed in excitement.

John looked at himself in the rear-view mirror and happily exclaimed “It’s Riley time now!” Riley started the car and made her way to the dispensary.

Riley bought a new vape, edibles she had read online that would make her even more horny than she already was, a THC drink, and a bath kit that had THC bath bombs, salts, an edible, and a joint. She had everything she needed for a nice slutty night. Her cock, had started to leak and it was going between soft and hard.

Riley drove back home with a fury of lust and slutness. She parked the car in the driveway and saw the packages on her doorstep. She got out of the car, with her score from the dispensary and headed inside. She got the packages open and slowly placed everything out for her to see and look at.

Her outfit for the evening was a dark blue wig, mascara, blue and black lipstick, black on the bottom, blue on the top lip, a dark blue bra, with a black fishnet top, black stockings, a dark blue skirt, and dark blue girly shoes. While Riley was looking at the outfit, she could feel her cock press against the cage. She reached down to the tip of the cage and felt precum on her finger. She brought it up to her lips and rubbed it in. She felt a shiver go down her spine.

Up next she pulled out four dildos, each of various sizes. One was a flesh cock about six inches in insertable length. Next was a similar-looking cock about seven inches in length with a bit of girth. The last two were two huge big black cocks, both at least nine inches and thick. Looking at those two made her cock strain in the cage even more. Her body wanted it but she had to tease herself. She had to wait. The last items she pulled out of the box were black and blue nail polish.

Riley stripped down to her thong and put the suit away. She laid her outfit for the evening on her bed, grabbed a silky nightgown, and sat on the couch to search for the perfect porn for the evening. Before sitting down she took a small edible, something to relax her before the night got going. She would wait until it became a night to get the party started. That wouldn’t be for a few more hours so she had plenty of time to do what she needed to do. Tonight she would go all out and tomorrow she planned on recovering from her evening and doing research to get her to her ultimate goal. The Vegas Bonanza she called it.

Riley sat down and started going through porn sites and the porn she had saved. Over the last six months, she had built herself a goon cave. Multiple TVs spread in such a way that when she turned she would always see porn if she stayed in a certain area. She had a TV up in her room as well and a computer that she could throw videos to on certain TVs. She would have so much sissy porn, blowjob porn, hypno, and other things going on this evening she would make her mind melt. She spent the next several hours finding what porn she wanted and got them into the spots of her place she wanted them in. She wanted a club-type of atmosphere. Her next task was to get the music playlist built. The small high from the edible kicked it. At this time she started to take hits from her vape pen enjoying the high she was starting to create.

She had decided that once the playlist was done she would start to get ready. She had her mushroom dose picked out, her bath kit ready and she was ready to go. All the while she was leaking through her cage. In the last few weeks, she started the “Holy Cum Grail ‘’ regiment. She wanted to leak all she could while she was caged. She wanted to be a unicorn sissy slut. The playlist was completed and now it was time to start the night.

The sun went down and it had been dark for about an hour. Riley went into the bathroom and started the bath. The bath would take some time to fill up. She took the edible that came with the bath kit and went outside to smoke the joint that went along with it. She stood out there in her silky nightgown and things. The bulge of the cage moved as her cock grew hard and the cold air hit her as she smoked her joint. 

The new level of high was starting to set in. That level of high where you need something in your ass to grind on. 

Riley finished the joint and walked back inside the house. Along with setting up a goon cave theme over the past few weeks she also set some lighting up that would be like a club. She had strobe lights, black lights, and other things set up to accomplish this. It was going to be like going to a dark club, with good music and most importantly good cock. Riley stripped down to just her cage and walked into the bathroom. She put the bath bomb into the water along with the bath salts and started to rub the bath salts onto her body. She had been looking forward to this moment. The high from the joint was kicking everything up a notch and the edible would kick it up a notch in thirty minutes.

She put one foot into the bath and a moan left her lips. The water was perfect. She turned out the lights and let the candles light up the bathroom. She slipped into her shoulders and just laid there enjoying herself. Listening and feeling her body. It wanted cock, it wanted its holes pounded, but it isn’t time yet. It was time to clean and let the senses build. She could hear the porn and music circulating through the house. It was perfect. It sounded like a sex club. She could feel her cock getting hard again in the cage. It made Riley hornier knowing that she couldn’t touch her cock. 

The high from the edible began to kick in. Her senses became more heightened and more than ever she wanted to get dressed and start the fun. Riley got out of the bath and dried herself off from head to toe. She grabbed the nail polish and sat in the bedroom as she watched the dick-sucking porn on the TV as she painted her nails black and blue.

She took her time soaking everything in. She walked out of her bedroom and took her low dose of magic mushrooms. It was just the right amount to send her into a new horny dimension of slut dome. They would take an hour to kick in so she could take her time getting ready. She went ahead and poured herself a drink with a few shots of Fireball and mixed it with the fruity THC drink she had gotten at the dispensary earlier. Her ass wanted something inside of it.

She went back to the bedroom and opened up her chore where she kept her toys. She was eyeing a plug that would be perfect. It was a medium plug about two to three inches long with a diameter of just over two inches. The base of the plug said “Cumslut” on the bottom. She grabbed a towel from the bathroom, and some lube and laid down on the bed. She put some lube on her finger and slowly teased her hole. She could feel her cock getting hard in the cage. Her hole wanted to swallow her finger and finally, she let it happen.

She lay on the bed and slowly fingered herself. She didn’t want to get carried away, so she took her finger out and lubed up the plug. Like the good little slut she was, her hole swallowed the plug with ease. She could feel her prostate start rubbing up against it. Her cock throbbing inside the cage, she was in heaven.

She got up from the bed and took a drink. It tasted good with the hint of cinnamon from the fireball. She grabbed the blue bra from the bed and put it on. She followed that with her black mesh top. She grabbed the blue wig from the bed and walked into the bathroom. It took her a few minutes to get the wig to sit the way she wanted it on her head. She kept catching a glimpse of herself in the mirror and it was continuing to make her hornier. She was jumping out of her skin to have something in her mouth, but she remained disciplined. She grabbed the black lipstick and applied it to her bottom lip. She then applied the blue lipstick to her top lip. She finished off with the black mascara on her eyes.

Riley walked out of the bathroom and turned up the music. It was close to go time. The mushrooms were starting to mix nicely with the edibles, music and porn. Riley put on her black stockings, followed by her blue skirt, and then she finished off with the blue shoes. She grabbed her phone and took a self and an overhead picture. She thought she looked so fucking hot. The last thing she needed to do was place the dildos where she wanted them to go. The first flesh-looking six-inch dildo would was placed on a closet door in the main room with the music and porn.

The slightly bigger seven-inch dildo would be put on the toilet seat. Lastly, the two big black dildos would be placed together on a door in the main room where the music and most of the porn were playing. The lights were already dim in these rooms and she adjusted the bathroom lighting to match. It was time. The final thing Riley did was put a condom over her cage. 

Every time she would cum or start leaking she wanted it to be caught by the condom. At the end of the night she would take the condom off and like a good slut, dump it on her face.

She stepped out of her bathroom and imagined herself at a club. With her drink in hand, she started dancing. She was feeling the music and was in awe when she looked up to see the porn videos, the cock, the naked woman everything was coming together. With the magic mushrooms starting to do her things, the colors become wonderfully brilliant. She could feel her plug rubbing up against her prostate. She wanted more as she took another gulp of her drink and put it down. Three songs in she wanted to suck the first dildo on the closet door.

She made up a scenario in her head that for a hit of the person’s vape pen, she would suck his cock. She grinded up against the door and dildo, pretending someone was groping her as she placed one hand on the dildo and slowly started to stroke it while still dancing. As she stroked it she took a hit from the vape, she exhaled and smoke went everywhere. She was in awe of how brilliant it looked against the lights and colors coming off from the TV. 

Her cock was hard in the cage. Riley got on her knees and looked up imagining as if someone was looking down at her. She took another hit from the vape pen and proceeded to put the dildo in her mouth. She started slowly but soon was taking as much as she could into her mouth. She could feel the spit start to drip down her face and onto her body. She was getting more turned on and more into it. She moaned as she took the cock deeper and deeper. She wanted the cock down her throat, she wanted it balls deep. She could feel herself getting close to cumming. She looked up and imagined a guy’s face in pure ecstasy as she deepthroated this dildo. 

She took the dildo out of her mouth, looked up, and said “Give me one more hit of the vape, and I’ll take your cock down my throat when you’re ready to cum hold my head down.”

She took one more long hit from the vape and held it in as she took the dildo as deep as she could. She took one of her hands and pushed the back of her head balls deep onto the dildo. She exhaled the smoke, went cross-eyed, and came. She took the dildo out of her mouth, covered with spit, and put some traces of it onto her face and imagined it was cum. She stood back up, smiled, and headed to the bathroom to fix her makeup.

Riley got to the bathroom and shut the door. She grabbed her phone and took a few pictures. She wanted to see how messy her face was and pulled up her skirt to see her first load in the evening in the condom. After seeing that her dick grew hard in the cage and her asshole started to grind on the plug again. She hadn’t gotten off in a few days and with the “Holy Cum Grail” regime in full effect, it was a massive first load. She caught a glimpse of herself in the mirror again and saw that her mascara was running, her lipstick was messed up, and the spit and drool from the blowjob earlier was still lurking.

As she reached over to grab more makeup, she saw out of the corner of her eye the second dildo. A little longer than the one she just swallowed and a little thicker.

As she got done fixing herself she looked into the mirror and said, “Hey big boy, are you a little horny over there?” She imagined a horny clubgoer in the bathroom jerking his nice cock off.

Riley stood over the cock and bent over exposing her cage and butt plug to her imaginary thoughts. She stood back up and turned her head around.

“Like what you see,” she said in a flirtatious voice.

She started to go down to her knees and started to lightly take the dildo into her hands.

“I just got done sucking someone off. I like the way your cock looks. Do you want me to gag on it?” Riley said in a slutty voice. She imagined getting a nod. Her lips hit the tip of the dildo and she worked it into her mouth.

The plug started to grind up against her already swollen prostate, her cock growing hard in the cage. She sucked then deepthroated a few times causing her to gag and create spit.

She took the wet dildo out of her mouth and slapped it on her face, “You like it when I choke on your cock, don’t you?”

Riley took the cock as deep as it would go until she gaged again and continued to do that over and over again. Her eyes started to water. Her hole grinding against the plug. She reached back and spanked her ass. She tried to take the cock further into her throat and she gagged and came up for air. She let out a moan and once again slapped and rubbed the dildo across her face spreading the spit around. She was all in now, she wanted to take it down her throat.

She felt another orgasm coming. “Make me gag on your cock and cum down my throat,” Riley said as she went back to sucking the dildo.

Her head bobbed and she gagged for the next few minutes as she could feel herself building to another orgasm. She wanted to take the entire cock down her throat and cum. With tears coming down her eyes she forced the rest of the dildo down her throat and her nose touched the balls. The second her nose touched the balls she came again. She felt her whole body relax as she slowly started to come up for air. Halfway up, she went back down on the dildo balls deep and gagged on it again as she rode out the orgasm.

She came up for air and made the dildo hit her on the face and smear more spit over her face. At this point, she wasn’t going to redo her makeup. She looked at the dildo one more time and took her phone out. She went balls deep again and took a picture of herself. She came up for air again and admired the picture she had just taken. She sat there and looked at the spit-covered dildo and said, “You have a nice cock. Thanks for the cum and the fun time.”

Riley got up off the ground and staggered her way to the kitchen. She found her vape took a hit and made herself another drink. She sat on the couch for a while admiring the porn and the music.

As she sat there, she started to scroll through the pictures she had been taking through the evening and started to get horny again. She loved seeing herself look like a complete whorish cock slut. She could feel her cock getting hard again. The mushrooms had started to come back on and the vape hits were getting Riley back into the groove again. 

Riley got up with her drink and started dancing again. She was slowly dancing her way to the big black dildos on the door. She was nearly finished with her drink when her favorite song came on. She downed it and danced her way to the big black dildos on the door. Her imagination started to run wild as she got to the door. She started to grind on one of the cocks and took another hit of her vape. The high was kicking in again. She started to straddle the big cock and could feel her balls rubbing up against it.

Her prostate started to swell and push against the butt plug as she reached down and grabbed the other dildo. She could feel how big they both were. She was so excited, she wanted it so bad, but she teased herself further. She imagined guys groping her and feeling her up as their cocks got hard. 

“You want to make me a good slut?” She stepped forward, bent over, and pulled up her skirt as if there were two guys there looking at her.

As she looked down between her legs she saw for the first time how much cum was in the condom, it turned her on so much. As she looked at it she could see her cock get a little harder. She clenched her ass hole and she felt the plug go a little deeper. 

“Be a good slut and get on your knees,” Riley imagined.

She walked over and got down on her knees. She wanted to get rough with these huge black dildos. She took one as deep as she could and gagged. She spit the juices on the other dildo and went back and forth gagging on each cock. Whatever cock wasn’t in her mouth she was stroking it. Riley noticed a lot of spit was getting on her chest and the floor. She got up moved one of the dildos underneath the other and grabbed a bowl. As she gagged on one cock the spit would fall to the next one and into the bowl. 

Riley gagged and spit on the cocks for a while. When she switched to the big black dildo on the bottom, her spit from the cock above came down onto her face. Every minute of letting these large black dildo's face fuck her was thoroughly enjoyed by her. Spit covered her body. She was slapping the dildos against her face and smearing it all over.

Riley could feel her prostate swelling again. She took out her phone and snapped a small video of one of the cocks hitting her in the face. As she took a hit from her vape, she attempted to deep-throat the bottom cock while the spit from the top dripped onto her face. She gagged and came back up for air. Once she set her phone aside, she proceeded to make the dildos even.

She was switching between sucking one and stroking and hitting herself in the face with the other. She was on the verge of coming again. She deep-throated one of the large black dildos and experienced another orgasm. This was the hardest orgasm she had of the night. She took the dildo out of her mouth and got on all fours to catch her breath.

She looked down at the bowl for the first time. She didn’t realize how much spit had drooled into it.

"We aren't done with you yet," she believed she heard.

She grabbed her phone, the two dildos, and the bowl and went to her bedroom. She put the dildo on a door while across from her drawer. She got onto her bed and laid her head off of it. She took one of the big black dildos and face fucked herself for a while. She could feel the spit coming out of her mouth and across her face. She felt like such a whore. Riley thought it was time to finally get fucked. She got up from the bed and took her plug out of her ass. She licked the plug clean and took the bowl of spit and dildo to the drawer where the other dildo was. She was going to have one of these big dildo’s in her ass as the other was fucking her throat. She was going to spit-roast herself.

She used her spit to put around her hole that was begging for a big cock to slide into it. She put some of the spit on her dildo, took another hit from the vape, and slid the big black dildo into her ass. She thought she was going to cum again right there but she held herself together. She poured some of the spit onto her face and placed the bowl back under the dildo she would be sucking. She put the big black dildo in her mouth and began going back and forth. 

She was bouncing back on one dildo as the other was going down her throat. She was airtight taking the dildo in her ass balls deep. When she bounced back she would take as much cock down her throat as she could which caused her to gag and spit to fall into the bowl. 

She was moaning like a good whore when the first orgasm took her by surprise. She was so wrapped up in being pounded she didn’t realize it. As she was cumming she just kept going. Her eyes crossed like a mindless slut, she just rode the waves of orgasms as another orgasm quickly took her over.

She came twice in a matter of three minutes.

She took the cock out of her mouth and made it slap her face as she smeared the spit on her face. She sat back on the cock and took it all the way down to the balls. She sat like this for a minute to compose herself. She took a deep breath and slowly took the big black dildo out of her ass and collapsed onto the ground.

She was breathing heavily. She was still wanting more and her hard cock was still entrapped in the cage. She got herself to sit up on the bed with her legs shaking. She took her phone and pulled up her skirt. There was a ton of cum in the condom. Five loads worth. She took a selfie so she could show off her slut face with the condom rolled out on the cage to show how much cum was in it. She wanted to cum one more time, but she wanted the cum on her face.

She put another towel down on the bed and grabbed one of the big black dildos. She wanted to ride this cock. She used some of the spit from her bowl to lube her asshole and cock. She slipped the dildo into her aching asshole. When she had the cock in she slowly started to ride it. 

She postured herself straight up and dumped the rest of the spit in the bowl on her face and let it work its way down her body. She loved being such a filthy whore. She spread it out on her face and rubbed it down her body as she felt herself up. She could barely open her eyes but she reached down and took the condom filled with cum off the catch.

She started to bounce on the cock faster and decided it was time to get her reward. She could feel her prostate swelling and that’s when she started to dump the condom all over her face. The hot cum hit her face and some went into her mouth and down her body. She was enjoying being such a whore that she took one last picture of her cum covered as she rode the cock. She put her phone down after a few pictures and rode the big black dildo until she came for the final time that evening. She collapsed on the bed and let the big cock slip out of her asshole. The music had stopped playing.

She could still hear some of the porn playing, but she was in an orgasmic bliss. It took her about fifteen minutes to let her body have the ability to let her stand. She grabbed her phone and her legs shaked as she walked into the bathroom. She looked in the mirror at herself admiring how much of a sissy whore she looked and the night she had just had. She smiled at herself, took a few more pictures, took her wig off, and washed her face. She got back to the living room and turned off the porn. She would wait until tomorrow to clean everything up. She kicked her shoes off and collapsed in her bed. She could still taste her cum in her mouth as she fell into an orgasm sleep coma.

Riley awoke the next morning still in an orgasmic bliss. Her mouth and ass felt sore, but other than that, she felt great. She stared at the ceiling and thought about the night before. It took her a few moments to realize she was still wearing her clothes, still had her cage on, and could still feel the dried-up spit and cum from the evening. She smiled and got up. She stripped naked and walked into the bathroom. She turned on the shower, put a shower steamer in, and looked at herself in the mirror. She thought about her ultimate fantasy of Las Vegas and how last night was the first step. She needed to continue to plan to make it perfect.

She stepped into the shower and let the hot water fall over her. She soaped herself up, made sure she cleaned around the cage, and just enjoyed the nice hot shower. She stepped out and dried herself off. She walked back into the bedroom, put her previous night’s outfit in the hamper, and grabbed a silky robe. She sat down on the couch with her computer and took a small edible. She started to look up diets and workouts she could start doing, along with meditations and other ways to keep her mind in the sissy realm and to overall improve herself.

She settled on a stretching, yoga, jump rope, and body weight routine. She started to write down her plan on paper. What days to work out, for how long, when to take breaks. She also needed to incorporate her practice for sucking cock, keeping herself caged, and stretching her ass. She gradually wanted to work her way up in size with her butt plugs. She loved the feeling of being stretched and wanted to gradually find out where her limit was. She wanted to get to a point where she could have two cocks inside her ass at once. That would take time.

Riley would now keep her cage on 24/7. She would take it off for cleaning, but once that was done, it would go right back on. She would have ass stretching three times a week. She would also put down in her routine that on days she had a lot of errands, she would have to walk around with a plug in her ass. She also had decided that she would have nights like she just had one to two times a month. She would set the dates and prepare for them. 

Riley also set up a Reddit account and an Instagram account. She was debating whether to set up OnlyFans or not. She thought the idea of posting her pictures was hot, but was still hesitant because she didn’t want people she knew stumbling across it and finding out. She would talk about everything she did on Reddit, write stories, and get insight on what to possibly do next.

Her next big hurdle was to suck a real cock. She was cock and cum hungry but still hadn’t worked up the courage to do the real thing. She had gotten close but bailed out. She would use Reddit, Grindr, and Fetlife to find what she wanted. If she was going to suck her first cock, it was going to be exactly what she wanted. She was not attracted to men, but loved looking at cocks, wanted to taste it, wanted it down her throat. She got the idea of doing a glory hole to suck her first cock through. 

She started to ponder how she would do it. What she would need, where she would want to, how to be safe and what to wear!