Sissy Riley Is Helped But...

Note from the Writer!

*** I am so sorry this took half a year to write. I had this story done around CHRISTMAS but somehow accidentally deleted the entire thing. :/ That took a lot of the wind out of my sails to be honest. That and I had a minor surgery I am recovering from... but all is good with me now! I have mapped out 10 chapters for Sissy Riley's adventures and I am eagerly working on them now.

I KNOW Riley does not always act rationally... and will not always act rationally. Try to put yourself into the shoes of a chastity locked, sexually frustrated, gender confused person. Not a guilt trip but the power of the chastity cage is real... I am speaking from first hand experience.

Last thing! I jump back and forth between names, titles, and pronouns for individual people. With Riley for example, when Riley is dressed and actively being a sissy, all pronouns are feminine. When Riley is getting ready for work, a male front is presented so male pronouns are used. I hope its not confusing.

Otherwise enjoy the story! Being honest, this is another filler story to bridge until the next chapter where Riley is in big big trouble.

***

"SHANNON!" Mistress moved to the front door to intercept her. Before she turned the corner, she gave Riley a head nod motioning towards the couch. Riley was unsure what Mistress meant but crawled behind the couch staying out of sight. The other three ladies froze, Monica wearing only her bra, Emiley's panties sitting on the couch, and Lindsey still coming down from her orgasm. Her dress was hiked up around her waist exposing her clean shaven pussy.

Mistress was one step too late as Shannon rounded the corner seeing the three ladies. Riley was out of sight behind the couch. Shannon stopped dead in her tracks at the scene before her, never imaging this is the type of evening Rachel was having. Shannon's face went red with embarrassed realizing she just barged in on her friend's evening.

"Shannon, I ummm, didn't expect you to come over for a little bit yet..." Mistress said. There was some tension in the room. Monica, apparently having no shame, stood up and walked over to Shannon, wearing only her bra. She reached out to shake Shannon's hand.

"Hello... um Shannon is it? I am Monica! Nice to meet you! You must be a friend of Raven's!"

Shannon shook her hand, raised an eyebrow over at "Raven", and made a questioning face. Mistress just rolled with it and introduced her last two friends.

"Shannon, that is Emiley and that is Lindsey." she said motioning to each of the girls. "We were... uhhhh... just doing each others nails."

Shannon did a gentle wave and smile and looked around the room. Her gaze fell on a dildo, which unbeknownst to her, Monica had just used to fuck her son. She made a little face but did not say anything. She remained polite.

"It is very nice to meet you ladies... I am very sorry I dropped in unexpectedly. I just really needed to talk with Rachel... I mean Raven."

The other girls picked up on the vibes of the room and slowly collected their things to leave. Riley did not move a muscle. She was on her hands and knees not moving an inch since finding refuge behind the couch. Shannon watched the ladies pack up which made her feel worse.

"I am so sorry ladies. You don't have to go. I can come back. I did not mean to ruin the night."

Monica was sliding her panties up her body.

"Seriously do NOT worry about it. The night was ending. We were just having some fun waiting for our nails to dry... which they are now!"

Mistress rolled her eyes but smiled and reassured Shannon. "Monica is telling the truth. The party would have been in over in 15 minutes."

Shannon felt a little better she did not completely ruin the night. As shocking as this was, it was a nice distraction from the worry she had for Riley. Mistress walked her to the kitchen and poured two glasses of wine, handing one to Shannon. Shannon stood near the island and sipped as she watched the ladies pack up their things.

Once the three ladies were fully dressed and collected all of their belongings, they made their way out of the house. They thanked Mistress for a wonderful evening and asked about next weekend, which Mistress said she would let them know. After one last final goodbye and a round of hugs, it was just Shannon and Mistress remaining... and Riley hiding behind the couch.

Shannon walked back to the living room and did a little head shake and laugh. Mistress caught up with her after locking the front door. No more surprise visitors tonight. They both sat on the couch and Shannon started the conversations,

"I know I came here to tell you my problems but I would be bereft if I did not ask you about what I just stumbled upon... Raven!" Mocking her friends newly discovered name.

Mistress laughed and dropped her face into her hands. She was not sure why she was embarrassed. Shannon was her best friend but this was something they just never talked about.

"You walked into one of my Sunday night pedicure parties. I am... kind of involved in the local kink community. Raven is the name I go by when I am with kink friends."

This was quite a reveal but only the second most shocking thing Shannon found out tonight.

"Wow... today has been something. The two people I care about most in the world apparently are both very active in the kink life."

Riley could hear everything and her heart dropped. "What did her mom mean by that?" She continued to listen.

After a slight pause Shannon continued... "I got this email today... it was from some anonymous person. It had pictures and videos of Riley." Shannon trailed off. Her chest got very tight.

Mistress reached out and took Shannon's hand.

"What do you mean? Videos of Riley?"

Mistress had to feign ignorance but based her best friends reaction she knew what the email entailed. Riley was shell shocked at what she just heard.

"There was pictures of Riley at some sort of event... I am pretty naive to this sort of stuff but I know it was some sort of group sex thing. Riley looked like he was the center of it all."

"How did you know it was Riley?"

"At first I didn't! I thought it was a mistake. The person in the video looked like a girl... hell I thought it was a girl until one of the videos had a different angle. I saw a penis dangling between their legs. The last picture told it all though. It was a picture of Riley holding his ID... he was smiling in it!"

This was it. Riley's life was over. Master sent the video to her mom and probably her boss too. Riley did everything in her power to not openly sob. She could feel tears start to well up in her eyes.

Riley held strong but Shannon was the one who actually broke out into tears. Mistress put her arms around her and gave her a hug.

"It's okay honey. Look I don't the whole story but it doesn't seem that bad. Have you talked to Riley yet? This could be some sick joke or something."

"I thought of that and a part of me still thinks that... but the more I thought about it, the more sense it makes."

"What do you mean babe?" Mistress asked.

"I don't know where to start... lately he has been distant... I just feel like something is different."

Shannon choked up, took a deep breathe, and exhaled. She continued.

"Growing up he was always super interested in anything feminine... like... his whole life. I cannot explain it but somehow this makes sense. I mean I raised him as a single mom. He never had any male role models. I feel like I remember my clothes going missing. I don't know... it just makes sense. And you haven't even seen the video yet! He 100% looks like a girl."

Mistress wondered what Riley had to be thinking. She knew Riley could hear every word they were saying. She had a thought to just rip the bandaid off and out Riley right there. Mistress sat there and held Shannon for a little bit longer. She now understand why she just rushed over. Mistress needed to figure out the best way to diffuse the situation.

"Look honey, I know this is a shock to you. Hell it's a shock to me! You found out a lot of new information in the last hour... but look at us. We are best friends and live normal lives together. I... maybe... also have a little bit of a kinky side as well. It doesn't hurt our friendship at all. Maybe you and Riley can separate this and still go on like normal. It doesn't have to ruin your relationship, does it?"

Shannon stopped breathing so hard and started to think about what Mistress said.

"If anything, maybe this can enhance your relationship! I know you said you wanted a daughter." Mistress laughed as she gave Shannon a little nudge. "I don't know what you know but if he is that convincing of a girl, maybe you can go get your nails done together or help him in some way! Leave the kinky sex stuff out of it and maybe you can just do normal girly things with him. You'd love that!"

The mental image of going shoe shopping or getting pedicures with her son made Shannon laugh. She started to calm and pulled away from Mistress and gave her a smile.

"You think so?"

"I mean I don't know for sure but it is a possibilty. All I know is you need to talk to Riley. Maybe try to elicit a response or lay some breadcrumbs. I would not ambush him with it. Get him to open up."

Riley could not have been more thankful for Mistress right now. She would die for her. Riley's worst fear was turning into an opportunity thanks to Mistress.

Shannon was 100% more calm than she was five minutes ago. She grabbed her wine glass and finished the rest.

"Maybe you're right. Even though he looked happy in the videos... the person who sent it to me seemed like he was trying to... I don't know... get back at Riley for something though. That still has me worried."

Mistress was slowly realizing this may have been her fault. It must have been the man who FaceTimed her yesterday. "I guess I would be mad too if someone stole a sub out from under me" Mistress thought. She could picture his face but did not know who he was. She was pretty involved in the local kink community but her path rarely crosses with male dominants. Even if it would, she had no interest or need for them.

"Look Shannon, I will be honest with you. I am a Mistress. What you came across tonight was the other part of my life. These three ladies were other Mistresses in the area and we get together and have our fun and talk about potential subs and clients. That's what I do. I have a dungeon here in town where men, and some women, pay me to dominate them."

Mistress paused to let Shannon absorb the information she just unloaded on her.

"My guess is Riley could have a blackmail or humilation fetish. It is semi common with crossdressing men. They let dominates take embarrassing pictures and then have to do tasks so they don't send them to loved one or friends. If Riley did not do the task, he may have been forced to send the pictures. It is possible it may not have been vindictive or hurtful."

Mistress was grasping at straws but was trying to make her friend feel better. Riley was not sure if she liked the direction this was heading but there was nothing she could do. Shannon did not necessarily like the sound of that but at this point she was in over her head. She took a deep breathe and asked...

"Can you teach me more about this Rachel? If I can understand this kink lifestyle better maybe it help Riley and I's relationship."

Riley heard this and wanted to cry for a different reason now. Her mom knew one of her deepest, darkest secrets. Something other parents would be ashamed of and all she wanted to do was support her.

"Of course I can teach you! I have to say... I am surprised by the way you are taking everything. I am happy... but surprised."

"Oh this will DEFINITELY take me a bit to get used to. I am going to go to the bathroom, refill this glass of wine for a total of five glasses tonight, and I want you to tell me about these men who pay you to dominate them."

"That sounds like a wonderful plan!"

Shannon got up and headed towards the bathroom. As soon as she was around the corner Mistress planted her knees on the couch and twisted to look over the side of the couch. She smiled at her cowering sissy behind the couch.

"If I was you I would take this opportunity to escape unseen."

"Is that okay with you Mistress?! I cannot believe what you just did for me!"

"Yea yea yeah... you owe me. BIG TIME! You have no idea. I also was the only person who didn't orgasm tonight, which will never happen again. We will talk... I will send instructions for our next session."

Riley got up, walked over to Mistress, bent down to kiss her feet, and trotted out the back door before her mother got back. Riley escaped thanks to the graces of Mistress. As happy as she was to be out of that house, she was curious what her mom and Mistress were going to talk about.

Mistress and Shannon were back on the couch with their wine glasses refilled, sipping and chatting. Shannon started,

"Sooo tell me... RAVEN" Shannon said making lite of her friend's new nickname, "where does this play a role when giving a pedicure?" she asked picking up the dildo.

Mistress laughed and snatched it from her friend, their faces inches apart. "Let me show you..." she said all flirty. She wasn't sure if it was the wine talking or all her friends getting off without her, but Mistress was feeling very kinky and mischievous. She stared right into Shannon's eyes and held it. She waited to see what Shannon would do.

Shannon could feel the sexual tension in the room. She had never thought of her friend in a sexual way before nor had she kissed or done any sort of sexual thing with a woman, but at the moment it's all she wanted to do.

Time stopped as the two ladies stared into each other's eyes. Mistress was testing Shannon, wanting to see if she would make the first move. She didn't have to wait long because Shannon went for it. She leaned for forward and their lips locked, leading to a long deep passionate kiss. The two ladies made out on the couch for a good 15 minutes, exploring each others body's with their hands.

Mistress was the one who finally broke off.

"Look... I know you have been through a lot tonight. I want to make sure this doesn't lead to something we will regret when the wine wears off."

"Rachel, I've been a good girl all my life. My best friend and my son appear to know something I don't. Show me what I have been missing."

Mistress did not hold back anymore. She took Shannon by the hand and led her to her bedroom where they made love all night. They took turns fingering each other, eating each other out, and Mistress even pulled out a strap on to fuck Shannon. Shannon was bent over with Mistress fucking her doggy style. This went on for awhile and they switched to cow girl. Shannon was bouncing up and down on Mistress. During their fun, Shannon looked down to see the key dangling around Mistress's neck.

"What is that key for?" Shannon asked.

She leaned forward and nibbled on the key, not realizing she was holding the key to her son's cock in her mouth. Mistress was told Shannon it was a necklace a sub gave her and flipped Shannon over positioning herself on top. She took charge and thrusted hard into Shannon bringing her waves of pleasure. After an evening well spent and many orgasmed achieved by both ladies, they passed out in each other's arms.

It was Monday morning and Mistress woke up to her 6:00 am alarm. Her head was pounding as she cursed herself for drinking that sixth glass of wine. She looked over to her best friend still sleeping peacefully next to her. Last night was becoming more clear... from her party to her saving Riley from an embarrassing night to her and Shannon's promiscuity. Mistress thought about how she was going to navigate this new path Shannon, Riley and her were on.

Mistress got out of bed letting Shannon sleep some more. Downstairs, Mistress started grinding coffee beans for her morning latte. She began thinking about ways she could remain friends with Shannon and keep her son as her personal sissy. She needed to talk to Riley and see what she wanted to do. Riley apparently wanted very much to serve her but wondered what the service was in her mind. Mistress didn't want someone who serve her part time after work or on the weekends. She wanted a full time live in sissy who would be at her service all day everyday.

That's when a twisted idea crossed her mind. Riley knew her old master had sent the email to her mom... who says he also didn't send it to her boss? Riley was afraid of that and already thought it was a possibility. Mistress had the full video and could easily figure out Riley's boss's email. There was already a chance he did anyways. Mistress could send it anyways and if he already had a copy what would a second one matter? It would be game over for Riley. That would definitely push Riley towards her.

Mistress pulled out her laptop and started Google searching Riley's place of employment. She was not sure exactly what division or who Riley's boss was, but she found the contact information for HR and then switched over to LinkedIn and found a bunch of higher ups and peers of Riley's. She could easily upload the link and pictures and one of these people would definitely know Riley. The nail in the coffin for her was the picture of her holding her work ID.

Leaning back in her chair, she contemplated this course of action. Mistress felt pretty confident Riley would not suspect her. She had been extremely supportive of Riley, saving her from being discovered by her mother, and then an ally in the conversation that Riley heard. Her old Master had already outed Riley to at least her mother and seemed intent on hurting Riley. An email to her colleagues seemed par for the course.

Mistress thought about the next series of events. She *ensures* Riley's boss gets the email and Riley is ruined professionally. Word gets out Riley is a sissy and it would be near impossible to be respected in a professional job. Mistress could then come in supporting Riley and turn her into a full-time live in sissy. Mistress wondered if Riley ever considered transitioning into a woman. Start with hormones, then lip injections, and even a boob job. She was already super convincing and had a nice, girlish figure.

If she was going to do something she better do it quick. It was almost 7:00 am and Riley would be heading to work soon. A quick creation of a fake email and Mistress was ready. She kept the same subject, message, videos and pictures. The email was going to a company vice president, a couple intermediate managers (one was Riley's boss; Mistress did not know that but got lucky), and four entry level people who worked at the company recommended by LinkedIn.

"Annnndddd send!" With a woosh it was gone. Mistress felt a twinge of guilt but that was overcome by thoughts of having her own personal sissy and 24/7 service. Part one of this nefarious plan was over; now she had to be ready to mend and mold. She needed to prepare Shannon. She was going to get some blow back too. It may be 2023 but someone's son dressing as a sissy and staring in a gangbang was still out of the ordinary.

Mistress prepared an extra latte, walked back to her bedroom, and found Shannon awake laying in bed on her phone.

"Here. I made you a latte."

"Mmmm. Thank you 'Raven'". She still said it in a mocking tone but was smiling as she said it. "Things are good between us right?"

"Absolutely Shannon. It was just kinky fun. AND for the record... Raven is just what I go by in the kink scene. A lot of us like to remain anonymous and work other jobs. You would be surprised at how many people are in the community!"

It was not Mistress's intent, but that made Shannon frown. Mistress quickly added on.

"Look, the stuff with Riley... it's who he is. He isn't hurting anyone, it is not illegal. He is exploring and having some fun. I know it sucks he was keeping a secret from you, butttt so was I. You aren't mad at me! I hope..."