Sissy Riley Has an Unexpected Guest

Part 2 of Riley's Sissy Journey! Please read part 1 so the story makes sense. This is a world building chapter, setting up tough choices for Riley down the road. Same deal as the first one... 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 am a finance person, not an author or anything of that nature. I write these for fun. With that being said, please enjoy part two of Riley's sissy journey!

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It was Saturday morning and Riley's mom, Shannon Rhinethaler, was out to brunch with her girlfriends. She was a very attractive woman, keeping up her appearances, trying to make sense of dating as a middle aged widow. Her first and only husband, also Riley's father, died in a car accident shortly after Riley was born. She raised Riley all by herself and they were extremely close.

Shannon and her girlfriends paid the bill and were talking about plans after. "What are you doing after this Shannon?" her best friend Rachel asked. Rachel was a 35 year old yoga instructor, eight years younger than Shannon. All the girls at the table were attractive, but Rachel was a goddess. She had perfect DD breasts and an ass worth dying for. Her body was in absolute peak shape from her active lifestyle. She had long black hair, always had her nails, eyebrows, and hair done professionally. Somehow she had always remained single throughout her life. Shannon never understood how it was possible. She dated more guys than Rachel did in the time they knew each other.

"It's Riley's birthday tomorrow and I want to drop off his birthday present. I got him a new money clip from Tiffany & Co. I have to go pick it up and then I was going to drop it off at his house." Shannon said.

"Aweee... that's so sweet. How is Riley doing?" Rachel asked. "I haven't seen him since he stopped coming to yoga with you."

"He is doing good! Really good actually. He got a new job at JP Morgan and has been working a lot." Shannon was beaming with pride over her son.

"If you don't mind, Tiffanys is right next to Louis Vuitton. I wanted to pick up some new shoes for my next date night. Do you mind if I come with you?"

"I don't mind at all. After we can swing by Riley's, say hi, and drop off his gift." Shannon was very polite but always wondered how her friend could afford such fancy things. She held her tongue though. She didn't feel like it was her place to say such things.

The girls said their goodbyes and Shannon and Rachel hopped in Shannon's car to drive to Tiffanys. Shannon pre-ordered and already paid for the money clip. She got it specially engraved, "For Mr. Monopoly. Love Mom." It was a little inside joke between them. Riley and his mom used to play monopoly when he was younger and she used to let Riley win. As Riley got older, he would beat his mom on his own... most of the time. She still got a win here and there. Shannon walked in the store, gave the sales clerk her name, and walked out with her son's gift.

Shannon walked over to Louis Vuitton and saw Rachel trying on some boots. She had two pairs of the Donna High boots, one black and one brown. "Help me Shannon, I can't decide which color to get."

"WOW Rachel... those both look amazing. Black goes better with your outfit now but I can definitely see you wearing the brown with some of your fall outfits."

"I know! I can't decide." Rachel got up and did a little runway walk checking herself out in the mirrors. She sat down, took off the black boots, put on the brown, and repeated the process. "I just can't decide! I think I will just get both."

If Shannon had water in her mouth she would have spit it out. "Rachel! Those are $2500 a pair... I am sorry babe... but can you afford those? I am not trying to be mean."

"Don't worry. I can afford them. I ummm, have other sources of income besides my instructing job."

Shannon was relieved to hear this but was left curious. She decided to not pursue. "I am sorry Rachel. I didn't want to be weird with money or anything."

"Girlfriend it's totally fine. Seriously. Don't feel bad at all. You don't have to worry about me." Rachel changed back into the black boots, asked the salesman to box up the brown boots, paid for both, and left.

As they were walking back to Shannon's car, Rachel made fun of Shannon. "You know, if you could have given me a decisive answer I would only have one pair right now."

Shannon laughed, "They both looked amazing on you! I think your next date will be very happy to see you in them."

The girls got back to Shannon's car and drove to Riley's. They pulled into his driveway but did not see his car anywhere.

"Hmmm I guess he isn't home. I am just going to run his gift inside and I will be right out." Shannon said.


"Do you think Riley would mind if I used his bathroom? I may have had one too many mimosas."

"No. He won't mind. Come on." Both girls got out of the car and walked towards Riley's front door.

Shannon let herself in with the key Riley had given her. Riley could be gone for long periods of time for work so she had a key to check in on things when he was gone. Shannon walked into the kitchen and sat down at the table and started writing her son a card. Rachel peeled off and went down the hallway towards the bedroom. She walked in the bedroom and what she saw startled her. There was a woman passed out face down on Riley's bed dressed in all pink. Like literally everything was pink! Rachel wasn't sure what to do. She looked closely and saw the high heels on the girls feet... they appeared to be locked to her feet. The more looked the more confused she got. She walked up to the girl and touched her shoulder gently, "Are you okay sweetie?"

The girl jolted awake and stood up. If Rachel thought she was in disbelief before, she had no idea what she was in now. The girl was terrified and Rachel realized it was no girl... IT WAS RILEY.

"Riley?!", she asked, still in disbelief. Here was her best friend's son, dressed in a complete sissy outfit, (which she was apparently locked in), face covered with what looked like cum, and a big "33" written in red lipstick on her forehead. "I am going to get your mom..."

"No Miss Rachel please." Riley whispered. "She can't see me like this."

Rachel's disbelief was subsiding and she was starting to think clearly again. "What happened? You have one minute to explain."

Riley had no idea what to do. Her life had gotten so out of control the last 24 hours.

"Please Miss Rachel. Do not tell my mom." Riley's voice was raspy from her event last night. Tears started to well up in her eyes.

Miss Rachel stood there and was losing patience. She pulled out her phone and turned on her camera. "Talk or I record you right now." Although she framed it as a threat, little did Riley know, Miss Rachel hit record right after she said it.

"Miss Rachel, please... I went to a kink event last night and I ummm... lost control of the situation."

"Riley..." Rachel walked forward to get an even closer look. She did a small circle inspecting Riley all over. Something about this turned Rachel on immensely. "This does not look like losing control. I have been to kinky events and no one just 'loses control' and ends up like this. Were you kidnapped or drugged?"

"Nooo ummm" Riley struggled to get the words out, "I attended an event last night and I was the maid for the party."

"Honey... your collar says 'Sissy' on it. Let's go get your mom."

"No!" Riley reached out to grab Miss Rachel's arm but forgot she was wearing high heels and fell over. Riley was doing a quiet cry now. Rachel walked up and zoomed in on Riley's face, recording the entire thing.

"I won't tell your mom... IF you listen... Get on your knees and look into the camera"

Riley slightly regained her composure and followed the instructions. Rachel continued, "Tell me your name, who your mom is, where you work, and what you are"

Riley gulped and was trying to think of a way out of this. Rachel was annoyed and opened her mouth, just about to scream out for Shannon.

"My name is Riley Rhinethaler, my mom is Shannon Rhinethaler, I work JP Morgan, and I am a huge sissy slut."

"What did you do last night sissy slut?"

"I was the main attraction at a gang bang. I had to satisfy 25 men with my mouth and sissy pussy."

Rachel smiled and turned off her camera. She stuck her right foot forward and pointed at her boot. "I will keep your secret, but I will have some follow up questions later. If you don't answer or respond to me, that confession goes to your mom. Kiss my boot if you understand."

Riley bowed down and kissed the tip of Rachel's boot.

"Good sissy. I will be in touch."

Rachel walked out of the room in disbelief what she just discovered. What an opportunity she thought. She got back to the kitchen and saw Shannon snooping through Riley's fridge. Shannon turned around and slightly blushed. "I just wanted to make sure my boy was getting enough fruits and veggies."

"I think you boy is getting plenty of nutrients." Rachel grinned at the double entendra.

"I hope so." Shannon said. "He was always such a skinny boy."

Shannon and Rachel left. Riley waited by the bedroom door listening, not making a sound. She heard the front door close and moved to her bedroom window. She watched her mom and Miss Rachel walk to her mom's car and drive away. She breathed a sigh of relief but was struggling to process what happened. First last night got way out of hand and now Miss Rachel knew her biggest secret.

"How did I even get home last night?" She thought. She didn't see her car in the driveway. Riley walked to her bathroom and looked in the mirror. "Oh no" she said out loud to herself, her reflection surprising even her. Cum was caked to her face, black stained tear trails came from her eyes, and there was the number "33" written on her forehead with lipstick. She was unsure what that meant.

The night was so foggy to her. The last thing she remember was the crowd cheering when she finished the last shot glass of cum her. "Was that what the 33 meant?" She thought. "Did I drink 33 shots of cum?" Honestly she thought she did more but it was all blending together.

She reached behind to unzip her dress but felt the padlock on her collar. "Where are the keys?" She got up to look around. Her purse and pink bag sitting on the living room couch. She rifled through her purse and found her phone and car keys, but no wallet or key ring for her clothes. Riley tapped her phone screen but it was dead. Riley trotted back to the bedroom and plugged her phone in.

Riley knew it needed a couple minutes to charge so she went to the bathroom to wash her face. She turned the water as hot as possible and on full blast. Riley let it run for a minute and just stared at her reflection in the mirror. She couldn't explain what she was feeling. Her life was so uncertain and she felt powerless... but something in her felt good. She splashed the hot water on her face and started scrubbing with her cleanser. It took seven rounds of cleansing for her skin to feel normal. Riley shaved and dermaplaned to give her face a reset. She finished with a vitamin C serum and moisturizer to her skin.

Riley sat on the bed, unpinning her wig and taking it off. She reached over and grabbed her phone. There was over 100 different notifications but she focused on the 27 unread messages. Most of them were from her Master. The first message was a picture of her locked in the pillory in her sissy maid uniform. She kept scrolling down, the pictures getting progressively worse. There was a picture of her sucking a cock, one of her from the side taking two cocks at once, another with her eyes closed taking a load of cum to the face... next was a cropped video where she begged for Jerome to fuck her in her sissy pussy. The more and more she scrolled the worse it got. Next was a cropped video of her drinking the 100th shot of cum. The crowd went wild when she gulped it down. She looked right in the camera, licked her lips, smiled, and thanked her Master. It looked like she was having a great time.

"100 shots of cum?!" she thought. "What the hell does this 33 mean then?" She continued to scroll.

Everything she saw so far was bad, IF people knew who she was. Luckily for her, her make up skills where really, really good and she was pretty much unrecognizable as a girl. The Miss Rachel thing was something she would have to deal with later. Riley was still trying to rationalize how she could make it out of this with no problems... but then she saw it. The next video she saw was going to sink her. The cover photo of the video revealed enough already. It was a picture of her in the pillory holding her driver's license in her left hand and her work ID in her right hand. She clicked on the video to play.

The camera was centered on her face, zoomed in. You could clearly make out what each ID said. Her Master was asking questions...

"Tell us who you are."

"My name is Riley Rhinethaler and I am a sissy, Master"

"What did you just do sissy?"

"I just pleased 25 men with my mouth and sissy pussy at my first gang bang Master."

"What do you love sissy?"

"I love being a sissy and I love pleasing other men. I love and crave their cum Master"

The video kept going with her revealing more and more personal information about her life.

"Why did I do this!" she thought. So much for remaining anonymous. Riley started to panic and threw her head in the pillow. She let out a small frustrated scream. She went back to her phone and kept scrolling. At the end was a long paragraph from her Master.

"Good Morning Sissy! I hope you enjoyed your night last night. I know we all did! I am sure you looked at all the pictures and videos I have. I think you realize the power I have over you now. I am sure your friends, family, and coworkers would love to see how you spend your free time! 😏 Lucky for you, I don't want to ruin your life, I just want you to fulfill your debt to me. You only provided 67 happy endings last night, leaving a debt of 33 to me. Until that is fulfilled, you will be in service to me. I am sure you have looked for the keys to your outfit... I still have them. Clean up as best you can and be back to my house at 600 tonight. I will unlock you from your clothes and give you your IDs back."

Riley sat back and felt somewhat relieved. Master could ruin her life but was not going to. The only question was how was she going to get back to Master's dressed as she was. She looked at the clock and saw it was 1:45. She had a little bit of time. Her stomach started the rumble. Riley always fasted 24 hours before any kinky event so she had not eaten anything in 36 hours... nothing except for 100 ounces of cum. She walked to the kitchen and grabbed a parfait. She stood in front of the fridge, quickly ate it, and grabbed a water. She wasn't sure what she was going to be doing later so she wanted to keep her stomach empty.

Riley started to walk back towards her bedroom when she noticed a gift on the kitchen table. Riley used her pink glittery stiletto nails as a letter opener and opened the card. Her mom wrote a heartfelt note and how proud of Riley she was. This made Riley happy and nervous. She was unsure how this Miss Rachel situation was going to resolve itself. "Hopefully she doesn't call or text when I am with Master!" Riley thought. "Now I know why her and my mom where in my house though..." Riley finished opening the gift and saw the money clip. She loved it! She laughed when she read the inscription... her mom always knew what to say.

In the bedroom, Riley made plans for the evening. Lucky for her it was close to Halloween. She decided to order an Uber and if any comment was made she was act like she was going to a Halloween party. Riley spent the next four hours reapplying her makeup, styling her hair, and giving herself enemas until she was clean inside. It was getting close to 6:00 pm so she ordered her Uber. There was an Uber 5 minutes away so Riley quickly grabbed her purse and put on a large, long tan jacket and a scarf. The jacket and scarf covered most of her outfit; only the heels and part of the mincing ribbons were uncovered.

Riley got the one minute warning from the app. She walked outside and locked her front door. Her Uber was down the street and she started walking towards the road waving at it. The car slowed down and Riley saw the driver making a puzzled face at her. The driver looked at his phone and looked back at Riley. He rolled to a stop and rolled down the window.

"Ummmm are you Riley?"

"Yes Sir. Sorry for the confusion. I am headed to a Halloween party."

"Oh... um no problem. I just thought I was driving a guy from your Uber picture."

Riley did a fake laugh and said, "Haha. Yeah sorry. Girlfriend wanted me to wear this for her party tonight."

The driver looked skeptical but unlocked the car and let Riley in. Riley kept her head down and was on her phone. She texted her Master letting him know she was on the way. A quick car ride later and Riley arrived at her Master's house. She thanked the driver and got out of the car and walked to her Master's front door. Riley reached the front door and knocked. There was no answer. Riley knocked again and waited. Still nothing. Her phone vibrating in her hand.

"Put down your purse, take off your outer clothes, and kneel in front of the door." Riley looked around and did as she was instructed. Master opened the door grinning, holding the leash in his hand.

"Sissy!! I am so glad you decided to come back! I knew you had a good time last night." He reached down and attached the leash to her collar. "Follow me sissy."

Master grabbed Riley's things and took her inside. He led to the living room and took a seat on the couch. Master pointed to the floor and Riley knelt in front of him.

"I bet you're wondering exactly what I have in mind for you... tonight nothing special. Just you and me tonight. I thought we could sit here and watch the tape from your gang bang. I sent you some of the highlights. Did you enjoy them?"

"Yes Master. Honestly... I am scared and did not like that it was recorded. BUT... I will admit a part of me absolutely loved it."

"Sissy, I have been a Master for a long time. I can tell what girls are meant for this life and what girls will regret it. You are absolutely made for this life. You are made to please and serve men. You were a natural last night. Thanking each person for their loads, taking 10, 11, 12 inch cocks with ease, drinking 100 ounces of cum... this is my 22nd year in the kink life and I have never seen someone perform at that level their first time. Every single man last night asked me if they could see you again. Every. Single. One."

Riley blushed at what her Master was saying. Was what he was saying true? Was she made for this? She definitely enjoyed it. How could she make a living doing this? What exactly would she be? A professional sissy? She was deep in thought trying to make it work in her mind.

"Earth to Sissy. Helloooo." Master interrupted her thought.

"I am sorry Master. I was thinking about what you said. I cannot deny I love being a sissy. I don't know about my future though. What about my mom, my friends... what would they think?"

"We can talk about it later. You are still mine for awhile and if you don't please me you won't have a choice." Master started to unzip his pants. "Come here and suck this dick while I watch your gang bang again. The sooner you make me cum, the faster you can watch. Until then, I want you to listen to how sexy you sound."

Riley crawled forward and positioned herself between Master's legs. She leaned forward and took his soft cock into her mouth. Master reached for the remote and hit play. Riley started by swirling her tongue all around his cock. She bobbed her head up and down, going from only the tip in her mouth to her nose pressed against his abdomen. Master's cock grew quickly making Riley deep throat his cock. Riley was so focused on Master's cock she didn't hear her phone vibrate in her purse next to Master. It vibrated softly for 30 seconds and stopped. A minute passed and it went off one more time. Master heard this and reached into her purse and pulled out her phone.