Sissy Riley Makes Her Choice

Part 3 of Riley's Sissy Journey! Please read part 1 and 2 so the story makes sense. Riley makes a tough decision but feels it is best for her. Same deal as the first two... I re read this story 10 times to try and find any typos but my brain always auto corrects it for me. If you find any typos, please message me politely and I will fix it. I write these for fun. With that being said, please enjoy part three of Riley's sissy journey!

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"Soooo... you want to tell me who Miss Rachel is?"

Riley sat in front of her Master, stunned at the question. She was so focused on sucking his cock she never realized what happened. Cum was dripping down her face, falling on her lap. "Master, I don't even know where to begin... I don't even know what she wants with me."

"Well it looks to me like she is trying to blackmail you. What is she threatening you with?"

Riley told Master the story about how Miss Rachel stopped by Riley's house with her mom to drop off a birthday present. Miss Rachel found Riley in her bedroom used and abused from the prior night's gang bang. Miss Rachel pulled out her phone, recorded Riley, and threatened to call her mom over if Riley didn't comply.

Master heard the retelling and couldn't help but laugh at her predicament. This sissy went from her small bubble to be blackmailed by two people in less than 24 hours.

"Well... it sounds like you are in a pickle, sissy. What would be worse for you? Your mom seeing dressed as a sissy with cum dried to your face, or everyone at your work seeing your gang bang for free?"

Riley just wanted to sink into the floor... she felt trapped with no way out. Riley dropped her head and said, "Master, I will not let Miss Rachel interfere with serving you."

Master smiled at his Sissy and reached out towards her. He gently put his hand under her chin and tilted it up, locking eyes with her. Master held his gaze for about 10 seconds until Riley looked away. He had some plans for his Sissy but wanted her complete devotion. He was worried about Miss Rachel. Master unclipped Riley's leash and stood up. "You've had a rough couple of days. Let's get you out of these clothes."

Master grabbed the key ring from his pocket and unlocked all the padlocks. Riley was standing in just her bra and thigh highs in the living room. Of all the things removed, she was most happy about the high heels.

"Go upstairs and shower in the spare bathroom. I will lay an outfit out on the bed and you will spend the night here. Go now."

Riley did a little bow for Master and went to the bathroom. She turned the shower on high and as hot as possible. Riley unhooked her bra and then took off her chest plate. She filled the sink with hot water and placed it in the water to soak.

The mirror fogged up as Riley was looking at her reflection. There was a battle ragging on inside her. She always dreamed about being a "professional sissy". Living life as a girl, serving many different Masters and Mistresses, performing on camera... it all appeared to be possible. She worked so hard for her job though and never wanted her mom or friends to know.

Riley sat down on the side of the tub and pulled off her thigh highs. She bunched them up and tossed them in the corner with her bra. She unpinned her wig and gently removed it with her wig cap. She walked over to the bed and set them down. Riley walked back to the shower and stepped in. The hot water put her at ease, standing under the stream, enjoying the warmth radiate all over her tired body. Riley started replaying the last 24 hours in her head, from dropping the glass to kissing Miss Rachel's boot, she replayed it all.

The bedroom door opened and Riley heard some one walking towards her. The footsteps stopped for a moment and continued going again. Master poked his head in the bathroom, "I put your outfit on the bed for the night. Put everything on and come into my bedroom."

"Yes Master"

Riley thoroughly washed her hair and body. She enjoyed the water for a couple more minutes and got out. Riley padded her body dry and wrapped her hair in a towel. It was long but no where near her lovely 30 inch platinum blonde wig. It would be at least a year before she could get her hair that long.

Her chest plate was still soaking in the sink. Riley walked over and hand cleaned it with a mild hand soap and dried it. She found some baby powder under the sink and applied a thin layer to her chest plate and upper body. Riley removed the towel and put on her chest plate. It felt good to have weight on her chest again.

Her hair was still damp so she grabbed the blowdryer and finished drying it. She pushed her hair back and tight and reapplied the wig cap. Riley applied hair glue and positioned the wig on her head. It flowed down and tickled her butt. She loved that princess feeling so much. Riley applied very light makeup and walked to the bed. Master laid out a pink teddy with little hearts on it, crotchless pink panties, and fuzzy pink slippers for her to wear.

In her nighttime outfit, Riley walked into Master's bedroom. It was very nicely furnished. There was a black framed king sized bed with burnt orange comforter and navy blue sheets, matching black nightstands and dressers, one long and one tall. At the foot of the bed lay a long ottoman with a blanket hanging over it. There was a large tv mounted on the wall directly across from the bed.

Master was in the attached bathroom; Riley heard the sound of an electronic tooth brush. She decided to kneel and wait in front of the ottoman. About five minutes later Master walked out of the bedroom and saw his sissy. "Good girl. You cleaned up well." Master laid on top of his bed. "Come drain my balls one more time before bed."

Riley crawled to Master and blew him one more time for the day. She kept him in her mouth as he exploded and swallowed every drop. Master pattered her on the head, "Good sissy. Only 31 more happy endings to go."

Master got out of bed and walked to the ottoman. He grabbed the blanket and revealed it was not an ottoman at all, but a long, padded cage. Riley looked at him in surprise.

"Surely you didn't think sissies would sleep in bed with their Masters?"

Riley didn't need to be ordered into the cage. She immediately got off the bed and crawled in. The cage was narrow making it difficult for Riley to get comfortable. She laid on her side with her back against the wall. There was a small pink pillow and a pink fuzzy blanket. Riley looked up at her Master who was pressing buttons on a electronic padlock.

"I wake up at 7 am every morning. This padlock will beep and release you at 6:55. I enjoy waking up and my morning wood taken care of. Place my cock in your mouth at exactly 7 am or there will be consequences."

Master placed the padlock through the metal loops and with a "click" locked Riley in for the night. He replaced the blanket blocking out all light for Riley. Master hit the lights and went to bed.

Riley laid in her cage cramped. Her body was exhausted but her mind was racing. She thought about her future some more. What was the point of college, the internships, the networking, HER BRAND NEW JOB! Was she happy there? For the first time in her life she felt something... like she wasn't on autopilot. She wasn't sure if it was purpose and clarity or regret and shame. Did she even want to be an investment banker? She chose that career because that's what her father did before he passed. Riley envisioned her life waking up everyday in femme... no... scratch that... not dressed in femme but as an actual trans female, and going about her daily routine. Fantasies of her getting a boob job, lip injections, and starting HRT danced in her imagination. Riley was smiling as she finally drifted off to sleep.

Riley was woken up at 655 by a light beeping. It felt like she slept for 10 minutes The electronic padlock made a "click" sound and unlocked. It was still dark in the cage but Riley poked her fingers through the slits in the door. She felt for the lock and found it, unlooping it and swinging the door open. Riley crawled out and tried to stand; her legs were dead from being cramped all night. Master was gently snoring away. Riley saw the clock on his night stand... 659! She quickly crawled over and laid next to Master. She pulled the covers down below his waist and shimmied his underwear down to his mid thigh. Master began to stir. She laid her head gently on his stomach and gave the top of his cock a little kiss. The clock said 7:00 and a gentle melody began to play, slowly increasing in volume. Riley engulfed Master's morning wood and let it sit in her mouth. A minute passed and the alarm was loud enough to wake Master. He looked down and saw the blonde head laying at his waist and loved how his cock was feeling.

"Ahhhh the best way to wake up!" he thought.

He reached over with his left arm and turned off the alarm. Riley could tell Master was awake and started to bob up and down and swirling with her tongue. Master's morning wood turned into a full raging hard on. Riley continued, up and down, up and down, swirling her tongue. She pulled her head off and licked from the balls to the tip three times. She put Master's head back in her mouth and slowly swirled her tongue around the tip, simultaneously jerking and twisting with her hands. Riley could tell Master was close. She repositioned and knelt between Master's legs. Both of her hands were behind her back as she bobbed up and down as fast as she could. Riley felt Master's cock twitch as he grabbed the back of her head forcing it down. Master came hard down Riley's throat. After a couple of streams he started to ease off and let Riley come up for air. Riley gently sucked any remaining cum from his cock and gave the tip one last lick. Kneeling on the bed, Riley cocked her head back and opened her mouth holding Master's cum on tongue. Master chuckled and said, "You can swallow" which Riley promptly did.

Master went to the bathroom while Riley made Master's bed. She finished and then tidied up her cage. She folded the blankets and set them on top of the cage. Master walked out of the bathroom and told Riley to follow him downstairs. Master sat on the couch and flipped on the TV and opened his laptop.

"Make me a cup of coffee. I will take it how you like your dick, and make some toast. After that you'll be good until tonight."

"How I like my dick Master?" Riley was confused.

"Yes sissy. Black and large. Use one of my tall Yetis."

Riley blushed and said "Yes Master" and made everything how he wanted. SportsCenter was on the TV and Riley could hear her gang bang playing softly on the laptop. She handed Master the coffee and placed the toast on the table in front of him. She knelt and waited.

Master worked for about 15 minutes, taking the occasional sip, and eating his toast. He did some final typing and said "All done!" He closed the laptop and looked at his sissy.

"Your car keys, IDs, and a bag of your clothes are on the kitchen table. Don't forget your stuff upstairs. I will send you instructions how to dress tonight. I have some friends coming over for the football game. I also sent you a copy of your gang bang. Feel free to try and capitalize off that. I think you'll love the feedback you get."

Riley didn't expect Master to send her a copy of her gang bang. She wasn't sure if she was going to post it. Where would she even post it? Riley thanked Master for the honor of serving him last night, grabbed her things, and left. As she exited the front door, she realized she should have changed. It was too late now so she quickly trotted across the street in her pink outfit and quickly hopped in her car. Nothing like one more quick little adrenaline boost leaving Master's house.

Riley sat in her car for a minute. She really enjoyed last night. It looked like dinner tonight with her mom wasn't going to happen though. Riley pulled out her phone and looked at all the notifications. There was a bunch of Happy Birthday messages... an email from Master (how did he even get my email?)... and then Riley saw it. There was five messages from Miss Rachel,

6:05 "Who was that man?!"

6:06 "Answer me!"

*Missed FaceTime*

7:38 "Look who I am with!"

7:38 *One picture of Miss Rachel and Shannon drinking wine at a restaurant*

7:39 I warned you 😈

Then at 7:40 there was a missed call from her mom. Riley started to panic. Did Miss Rachel really show her mom the video?

There was a text at 7:41 from Riley's mom. "Call me please"

Riley couldn't stand to face her mom with her sissy secret. Driving home went by in a flash. She thought about every way their next conversation could go and couldn't think of anyway out of it. Riley backed into her garage and closed the garage door. She grabbed all her stuff and sauntered into her house. She felt defeated.

Riley walked into her living room and plopped down on the couch. She closed her eyes and laid there lifeless. A couple minutes passed and Riley thought she was dozing off becuase she heard the sound of high heels clicking on her hardwood floor. The sound was getting louder until in was in the room with her. Riley realized it wasn't a dream and jolted up. There was Miss Rachel, standing over the couch dressed in black latex bodysuit, a corset (giving her a ridiculous hourglass figure), and black leather high heels. Her hair was in a tight pony tail and her makeup was done to perfection, smokey eyes and red lipstick.

"Oh good. You're home!" Miss Rachel said.

Riley was shocked. "Miss Rachel?! How did you get in? HOW COULD YOU SHOW MY MOM THE VIDEO?!"

"Oh Riley. You don't need to worry. I haven't shown her... yet. I am giving you one more chance. Serve me or Shannon knows your deepest, darkest secret."

"Why did she call me? She sent me a text. I thought she knew. You said 'I warned you!'!!!"

"Oh sweetie. I just wanted you to call me. I told your mom I left something in your house... she was calling you to see if you were home. When you didn't answer, I asked to borrow the key so I could run in and grab my 'left item'. I spent the night here waiting for you. You have a really comfortable bed by the way."

Riley started to calm down. Relief swept through her body upon the revelation her mom didn't know about her sissy side. Riley could feel Miss Rachel's gaze on her. Riley collected herself.

"What do you want Miss Rachel?"

"I already told you! Serve me. I need a sissy maid to help me in my daily life and also in my dungeon. A good sissy is hard to find. I have been through so many in the last couple of years."

There was a lot to unpack there for Riley. First, Riley never knew anything about this side of Miss Rachel. Riley went to a lot of kinky events and participated in a lot of local online groups with Masters and Mistresses. Riley always thought Miss Rachel was a Goddess and had secret fantasies about her. There was a reason Riley went to Miss Rachel's yoga classes and it wasn't just to spend time with her mom.

"Miss Rachel, I would be lying if I said the thought of serving you didn't excite me... but I have a debt to a Master. I cannot stop serving him.... at least right away."

Miss Rachel walked towards Riley and sat on the couch next to her. She crossed her legs and brought her foot inches from Riley. Riley started to shift uncomfortably, her clitty was trying to break out of its cage. Miss Rachel started to unzip her shoe. She slowly pulled it off and held it between her big and second toe, dangling it in front of Riley. Riley could see all of her toes except for the big toe, which were all shaped perfectly and painted cherry red. Miss Rachel let the shoe drop. She slowly moved her foot towards Riley's clitty, sliding it under her teddy. Miss Rachel's foot rested on Riley's pre-cum soaked panties.

"I always new you had a foot fetish Riley. All those years of yoga staring at my feet."

Riley's face lit up bright red. "Was I that obvious about it?" she thought.

Miss Rachel pulled her foot off Riley's panties and moved it to her chest. Riley grabbed Miss Rachel's ankle and tried to kiss her foot. She moved deliberately and guided Riley off the couch and on her knees. Miss Rachel moved her foot up and placed her big toe on Riley's lower lip.

"Commit to serving me and only me and I will give you the honor of worshipping my feet."

Riley was lost in lust. Nothing else in the world mattered to her. Miss Rachel had her in the palm of her hand and she knew it.

"Yes Miss Rachel yes. I will serve you and only you." Riley cried out.

"Good sissy! You can start right now by worshipping my feet!" Miss Rachel stuck her big toe in Riley's mouth and Riley start sucking, kissing, and licking all over. It tasted divine. "You can also call me Mistress now. In the kink scene I go by Mistress Raven so you will call me that."

Riley started moving down to her new Mistress's other toes. She popped a new toe in her mouth and gave it a quick suck. "Yes", moved to the next toe, "Mistress", and the next toe, "Raven."Riley was in heaven.

Mistress let Riley worship her foot for about five minutes. She slide off her other heel and taped Riley on the head with her other foot. "Don't forget about this one sissy."

Riley switched feet and repeated her worshipping process on it. Mistress sat back and recorded the entire thing. Riley didn't have her full make up so she was decently recognizable. Just more footage to show Shannon if she doesn't listen. Mistress pulled her foot away and started putting on her shoes.

"That is enough for now. Serve me well and there will be more where that came from. I am having a Mistress party tonight and I want you there. Do you have a French maid outfit?"


"Yes Mistress."

"Good. I will text you instructions. I have to run some errands for tonight. Ta ta Sissy. I will see you soon."

Mistress put one foot forward and pointed. Riley gave it a kiss and Mistress went to the bedroom, grabbed a bag, and then left out the front door.

Riley had no idea Miss Rachel... or Mistress Raven now... was a Mistress. It kind of made sense now that she thought about it. She never seemed to have a boyfriend, worked very little, and spent money like it was nothing.

Now, Riley had a different problem though. She was supposed to be in two places at once. Master gave her one of the best nights of her life and gave her a wonderful opportunity with the video. He was very nice to Riley and treated her well. On the flip side though, Mistress was everything Riley ever wanted. Riley always enjoyed serving women more than men, and a he had an opportunity to continually Mistress Raven in her personal life and her dungeon. This could open up a bunch of new kinky experiences for her as well.

Also... Mistress and Master both had potential blackmail material on Riley. Neither seemed to want to ruin her life... but if she had to pick one to be unhappy it would have to be Master. At the end of the day, it would suck if all her coworkers knew, but all Riley cared about was her mom remaining ignorant of her secret.

It was still early so Riley wanted to give her Master as much heads up as possible. She sent the following text...

"Master, I feel absolutely terrible messaging you this but I have to tell you I cannot serve you anymore and will not make it your house tonight. I have a commitment I cannot get out of. I hope you understand and I wanted to thank you for everything you did for me. You gave me one of the best nights of my life and I will never forget it."

Riley watched the text send and immediately felt nervous. She did not want to end things this way with Master but did not see another way. He still had a chastity key but there was the spare. Mistress could remove it and buy a new one with two keys. "It is time for me to get a smaller cage too." she thought.