Sissy Riley's First Pedicure Night

*One Hour Earlier*

Shannon was washing dishes in the kitchen. There was a cake sitting on the counter that she had just finished baking Riley for his birthday. She hand dried the bigger mixing bowls and put them away. After she finished cleaning up, she poured herself a glass of red wine, grabbed her laptop, and sat down on the couch in the living room.

It was weird not seeing Riley on his birthday. He felt distant lately. Shannon hoped he was seeing a new girlfriend and wasn't quite yet ready to introduce her. New Girl was playing softly on the TV as Shannon wanted to get some work done.

She logged into her Mac and saw she had seven new emails. The most recent was a bill from Apple. $2.99 for iCloud Storage. Delete. The next one was from Amazon. Her package has shipped. "Cool" Delete. She went through until she saw an email address she didn't recognize.

Sissy Riley's First Gangbang

"What?" She was very confused. Her mouse hovered over the email and a little preview popped up.

*I thought you might want to know what Riley does on his Friday nights*

Those words haunted her and made her stomach drop.

"What is this? Why was I sent this!"

Shannon saw there was media attachments... she didn't want to look at them but felt compelled to do so. She clicked on one of the pictures. Her initial reaction was shock then confusion. There was a picture of a blonde woman wearing a pink dress locked in a stockade with cum all over her face. Shannon exited back to the email and clicked on one of the videos.

The video played and there was the same women locked in the stockade. From this angle she could see the women surrounded by a large crowd of men cheerily and acting with excitement. A man knelt in front of her holding a shot glass, collecting milk fluid from a collection bowl beneath this poor girl. He raises the glass to the girls mouth and she slurped it down as the men cheered and chanting "100!"

The man kneeling got up, did a bow, and motioned towards the girl.

"Sissy Riley's 100th shot of cum!" he announced loudly. The crowd went ballistic and camera zoomed in on the girls face showing her licking her lips and smiling at the camera.

The man said Riley again but Shannon was so confused. "Did someone mix up Riley's? Why did she get this video?" she thought.

Shannon clicked on the next video and was even more surprised than the last. Front and center was the poor girl bent over and largest cock she has even seen. The large black man had one hand firmly gripping her hips and the other was about to guide his cock into her ass. The girl was begging for his cock but the voice didn't match what she would have expected it to sound like. It almost sounded slightly familiar to Shannon.

She didn't want to admit it but felt slightly turned on... She regained her sense and started to look at the surroundings some more. "What was that between the girls legs?" Shannon zoomed in and saw that was no girl... that was a cock. This was a man! The man's cock looked different though, like there was something enclosing it.

That's when it hit her... this woman was actually a man... a man named Riley...

"No... that can't be my son" Shannon thought.

She clicked on the last piece of media and any hope it was a coincidence or prank vanished. There was her son locked in the stockade, smiling at the camera, cum dried to his face, holding his drivers license and work ID.

Shannon's chest got really tight and she started to tear up.

"Was Riley kidnapped? Forced to do this? Blackmailed?" Those types of thoughts raced through her head... but then she remembered the videos... Riley sure did look happy to do it. He was smiling and begging for it!

Shannon stated to rationalize what she saw. Okay... so her son was... let's say, into some unique stuff. She looked back at the first picture of the "girl" she saw. IF this was Riley, Shannon had to admit he looked pretty convincing as a girl. It wasn't until he talked where she even got an inclination that wasn't a girl. Then seeing the cock between the legs. "What was on it though?" she thought. It was pink and made it look tiny.

Shannon was always pretty vanilla in her dating and sex life. Whatever this was was way over her head. She thought back about raising Riley. He did have a fascination with all things feminine. He loved going shopping, helping her pick out new high heels, getting pedicures with her, keeping his legs shaved... Shannon always attributed it to Riley being raised by a single mother though. He never really had a male role model in his life after his father passed.

The more Shannon thought the more the pieces of the puzzle started to fit together. The initial disbelief was over but now other questions popped in her head.... "Who sent her this? Why send her this? What was her knowing supposed to accomplish?" She always imagined Riley meeting a nice girl, settling down, and having a family. She hit the reply button and typed out one question.

*Why show me this?*

Shannon hit send, grabbed her phone, and called her friend Rachel. As fas as Shannon thought, Rachel was just as vanilla as she was so she didn't think she would have answers, but that didn't matter. Shannon needed someone to talk to. She called two more times and then sent the text. Rachel replied immediately that she needed an hour. Ugh! Shannon wasn't sure she could wait that long.

She walked to the kitchen and poured herself a heavy refill of wine. Back at her laptop, she decided to investigate this lifestyle. The word that stuck out to her was 'sissy". Google provided the definition.

A person regarded as effeminate or cowardly.

Effeminate definitely described what she saw but felt there was more. She found a wikipedia page that led her to multiple pages about the kinky and fetish version of the word. She was reading when an email arrived in her inbox. It was from her mystery person and only had a one sentence response.

*To show Riley there are consequences to her actions.*

"What the hell does that mean?!" That answer scared Shannon. This email was meant to hurt Riley. Yes, it hurt Shannon and deeply shocked her to know there was this side of her son... but she still loved him. Shannon figured Riley probably didn't want her to know about this side of him... maybe that is why he was so distant lately. She needed someone to talk to.

"I am going to Rachel's house. She will understand." Shannon thought. She grabbed her coat, put on her shoes, and started the drive to her friend's house.

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Riley finished all the lady's pedicures. Monica and Lindsey both chose white polish, Emiley a red polish, and Mistress a dark purple. Mistress used Riley as a foot stool while the other ladies used the provided foot stools.

About 15 minutes of casual conversation passed when Monica asked, "Raven, how is your sissy at pussy worship? She's been wonderful so far, but how about we end this evening with some pleasure?!"

"Good idea Monica! Hold on one second."

Mistress pulled out the keys and removed Riley's posture collar. Riley was so thankful for that... she would rather have spent 36 hours in the high heels again before another hour in the posture collar. Riley crawled on her hands and knees to Monica and knelt before her. Monica stood and pulled down her body suit. She reached down and carefully pulled her feet through the leg holes, making sure the fabric did not touch her freshly painted toes. Then she pulled down her panties and sat back down on the couch in just her bra.

Riley crawled forward and started worshiping her pussy. She started with slow long licks on her labia tasting her sweet juices. Monica was already wet and turned on. Riley took her tongue and lightly licked her clit making Monica squirm with pleasure. A minute passed and Riley took her index finger and slide it inside Monica. Very slowly and deliberately she did the cum hither motion, ever so gently scrapping her black French tipped nail on the inner wall of her vagina, all while simultaneously licking the clit. Monica's breathing was increasing rapidly, the other three ladies enjoying the sexy scene unfolding before them. As Monica's breathing increased, Riley matched the swirling of her tongue on the clit and the motion of her finger. Faster and faster and faster Riley went until Monica screamed out and wrapped her legs around Riley, squeezing hard as she came even harder.

Monica's legs shook around Riley as she slowly eased the hold on Riley's head. Her heavy breathing subsided and looked at Rachel. "That was amazing Raven... I can't believe I came that hard."

"That looked amazing." Emiley said. She was already standing pulling off her panties.

Riley finally got released from Monica's leg hold and crawled over to Emiley. Riley used her same technique on Emiley and within minutes Emiley was screaming out in pleasure. Riley lapped up all the juices and gave her a gentle kiss right above her pussy. Lindsey was up next. She already had her panties off and her dress pulled above her hips, her clean shaven pussy front and center ready for Riley. Riley crawled over and starting worshipping Lindsey's pussy just like the first two ladies.

As Riley was working to bring Lindsey to orgasm, Monica walked over to the cart and grabbed a dildo and some lube. She lubed up the dildo and took advantage of Riley's bent over position and started inserting it in Riley's sissy pussy. She slid it in and out angling towards Riley's prostate. Riley did her best to focus on Lindsey but Monica knew exactly what angle and rhythm to thrust and was hitting Riley's prostate with precision. She started panting into Lindsey's pussy licking between moans of pleasure.

Monica pressed a button on the dildo and it came to life, vibrating with a strong intensity. It felt amazing before but the vibrating was pushing Riley over the top. Riley stopped worshipping Lindsey and was doing everything to not scream out. Emiley saw Riley was close and grabbed a little bowl off the pedicure cart. She placed it under Riley's caged clitty and waited. Monica saw Emiley was in position, clicked the dildo again to increase the vibrations even more and increased the speed she was thrusting.

Riley pulled herself into Lindsey's abdomen and smashed her face into it to muffle her scream. Waves of pleasure coursed through her body as she came from the intense dildo fucking Monica just gave her. Spurt after spurt of Riley's sissy cummies poured in the bowl. Monica keep thrusting in and out milking Riley for all she had. The cummies eventually stopped and Emiley held up the bowl for all the ladies to see.

"Oh my god! I can't believe how much she came!" Lindsey exclaimed.

Riley recovered her composure and started working on Lindsey again. It didn't take long for her to build up to that orgasmic feeling again and very quickly she came from Riley's expert pussy worshipping. Riley cleaned her up and was about to move on to her Mistress when Monica stopped her.

"Come her sissy. You have a mess to clean up first."

Riley looked at her Mistress who nodded approvingly towards Monica. Monica took her finger and lightly tapped her toes to make sure the polish was dry. Emiley took the bowl and placed it on the floor where Monica dipped her freshly painted white toes into the cum and soaked up as much as she could. Riley crawled over and licked the cum from Monica's foot. All over and between the toes Riley licked loving the taste and humiliation she felt. Out of the corner of her eye she saw Emiley recording it. At this point she didn't care, she was in so deep what was another video like this.

Monica repeated the process until she was scrapping the bowl like a spatula scrapping the last bit of cake batter out of the mixing bowl. Riley was going in for one last cleaning when there was a loud knock on the door. The four ladies and Riley all looked up, wondering who it could be. There was another loud lock and suddenly the sound of the door opening was heard. Mistress jumped up to see who it was but a voice called out.

"Rachel! It's Shannon. I am sorry to drop by like. I REALLY need to talk."

The door closed and Riley heard the footsteps start towards the living room.

"No!" Riley thought as sheer panic set in...