Sissy Riley's First Gang Bang

***Writers Note***

I am sorry for any typos you may find. I have a systemic problem where my brain always autocorrects typos and fills in words I omit. I always have friends/colleagues proofread for me but I didn't exactly want them to see what goes on in my mind... so take this with a grain of salt. If you find any typos please politely message me and I will fix it. Thank you and I love you people 😘💕. Hopefully you enjoy my first stab at erotica.

❤️❤️❤️❤️❤️❤️❤️❤️❤️❤️❤️❤️❤️❤️❤️

Sissy Riley's First Gang Bang

It was a cool Friday night in October and Riley's heart was pounding. She was sitting in her car across the street from her new Master's house. He was very vague but told Riley he wanted a sissy maid for the evening. She had been searching for months on the internet for someone who could be a long term Master and they hit it off online. Riley confessed many of her darkest fantasies to him but wanted to take it slow.

She was dressed in a casual outfit. Black sweatpants, cheetah sweater, and tan Ugg boots. Riley had her E cup chest plate on and her platinum blonde hair was in a messy bun. She pulled down her visor and the mirror lit up. She looked at her reflection and saw her long, luscious eyelashes. She loved the way they looked on her. Riley grabbed her lipstick and touched up her Cupid's bow. It was always the hardest thing to get juuuust right.

"Perfect" she thought.

Riley was trying to text her Master but kept making typos. She chose her stiletto pink glittery nails and glued them firmly to her fingers. They were the perfect choice to match her wardrobe tonight, but not the best choice for typing.

"I am parked across the street Master" she finally got off.

Immediately the three dots showing active typing appeared on her phone. Riley's felt a shiver take over her body. This was the moment she had been waiting months for!

"Come to the door Sissy"

Almost at the same time the front porch light turned on. Riley took three slow, deep breathes, grabbed her purse, and opened the car door. She went to the back seat and grabbed her pink bag. Inside was her uniform and everything she would need for the night. Her Master didn't want her to be seen walking into his house in her outfit by a nosy neighbor and she didn't blame him... it definitely would have turned heads and raised some unnecessary questions.

She walked across to street and approached the porch steps. Her steps were silent due to the Ugg boots. She enjoyed how comfortable they were.

"This will be the last time my feet will be comfortable tonight" she giggled at the thought.

She walked up five steps and stopped before the door. Riley was nervous. She took one more deep breathe and was about to knock when the door swung up.

"Hello Sissy" a middle-aged man said as he opened the door. "Come in" he raised his arm in a welcoming manner.

He was well kept with pushed back, slightly greyed hair. Riley guessed he was about 6'4 and was in decent shape. She found him very attractive.

"Thank you Sir." Riley blushed and stepped past Master. She walked through the door entering a hallway.

"The guest bedroom is upstairs to the right. There is a bathroom attached to it. I want you to get changed and into uniform right away."

"Yes Sir. It will take me about 30 minutes to change and finish getting ready. I hope you don't mind."

"No no... not at all. That will actually work out. I have some stuff to set up. Do you have something for me though Sissy?"

"Oh yes! Of course Sir. My apologies."

Riley reached into her purse and pulled out a key ring with five different keys on it and handed it to her Master.

"Thank you Sissy"

Riley got goosebumps all over. It turned her on so much to hear that.

"You're welcome Sir. I will go get changed now."

Riley did a little head bow to show complete submission and turned to the stairs. She made her way to the bedroom where she started to unpack her bag. First thing out of her bag was her pink collar. It had the words "Sissy Slut" written in silver sparkling letters and a "D" rings placed in the front for a leash.

Next Riley took out here tailored sissy maid dress. It was satin pink with light blue frills decorated all over.

She started taking off her "boring" clothes to put on her outfit for the night. She heard the doorbell ring and it sounded like a couple people entered.

"Oh my..." she thought, "I didn't realize there would be company"

Riley stripped down to put on her new panties. She slide them over her chastity encaged clitty. These panties were satin pink with white frills, but the best part was the unrestricted access to her sissy pussy. Her sissy pussy was currently plugged with her largest pink jeweled butt plug. Riley took a seat on a leather ottoman at the foot of the bed. She loved the way the leather felt on her freshly shaven legs. She scrunched up her thigh highs over her pink painted toes and pulled them up her legs.

Riley stood up, put on her pink garter belt, and secured the thigh highs with the fasteners. Next came the corset. Riley loosened it and shimmied it up her body. She pulled the strings until the corset was cinched all the way. Her waist went from a 28 to a 24, which gave her a wonderful hourglass figure. Now it was time for her sissy maid dress. Riley loosely tied a piece of string to the back zipper. She stepped through the back slit and pulled the dress over her shoulders. She grabbed the string and zipped it up. Riley heard another knock on the door. It was faint but it sounded like two to three more people arrived.

"What is happening down there?" she thought.

Riley grabbed one of the fourteen tiny padlocks she brought. She looped the lock through the metal rings on the back of her dress and with an audible "click" she was locked in her dress. The keys to her dress, chastity cage, collar, mincing ribbons, and high heels were all on the key ring Riley gave Master.

Riley finished getting dressed by putting on her high heels, mincing ribbons, and collar. She placed all 13 padlocks through the loops on her clothes. She was trapped in her outfit for as long as Master wanted.

Riley walked over to the bathroom, every step she jingled because of the little bells fixed to the heels and mincing ribbons. Riley looked at herself in the mirror and blew herself a kiss. She was unsure what she had gotten herself into but she wanted to be confident.

She looked at her hair and took out the scrunchy, letting her long hair fall down to her butt. Riley loved her 30 inch long wig. It made her feel like such a sissy princess. She brushed her hair and quickly did two small braids starting at each temple and connected them at the back of her head. She held the braids in place with a large pink bow. She looked at her lips and loved the red lipstick but it wasn't going with the theme of the night. Riley removed the red lipstick and applied a pink glittery lip gloss. She finished her makeup with a pink blush and spritzed her favorite sweet, floral perfume all over. Whatever was about to happen she was ready.

Riley walked towards the bedroom door and reached for the door handle.

"Here. We. Go." she told herself.

She walked down the stairs, jingling every step. Almost as if on cue, as she reached the bottom there was a knock on the door.

Riley froze. "Was she supposed to get the door? Surely this would be the task of a sissy maid, no?"

Her Master heard the knock and was heading to the door. He walked in the hallway and saw his sissy all made up. Riley saw him break a quick smile but he quickly stifled it.

"Good. It's about time. Answer the door for my guests. Properly introduce yourself to my guests. Lead them to the kitchen and offer them some refreshments. I need finish getting ready."

"Yes Master. Right away."

Riley turned to answer the door. At the door was three men. One man was one of the largest men Riley had ever seen. He was an African American and was about 6'7, 260 lbs of solid muscle. The other two men were decently tall and well built but looked tiny compared to this man.

Riley curtsied and motioned them in.

"Good Evening gentlemen. Welcome to my Master's home. My name is Riley. If you will please follow me to the kitchen for some refreshments. My Master is just finishing things up."

Riley was just about to take a step when the black man stepped in front and cut her off. His presence was commanding. He looked her up and down, never taking his gaze off her. Riley felt intimidated and looked down to avoid eye contact. The man grabbed her dress and slowly lifted it up checking out Riley's ass.

"Riley huh? I'm going to have fun with you tonight."

He stepped out of her way and let Riley lead. She was actually unsure where to go. She led the men to the sound of casual conversation, her heels clicking on the hardwood floor along with light jingling every step.

The four of them walked in the kitchen and Riley saw her guess was right from before. There was six men in the kitchen having a conversation plus the three she just brought. One of the men recognized the tall, built black man and set his drink down.

"Jerome! How are you doing friend?!" It's great to see you."

The black man, apparently named Jerome, and the man shook hands and engaged in conversation. Just when Riley was about to offer the men drinks there was ANOTHER knock on the door.

Riley trotted to the door and repeated the process. This time there was five men who were stunned to look at such a pretty sissy maid.

"Good Evening gentlemen. Welcome to my Master's home. My name is Riley. If you will please follow me to the kitchen for some refreshments. My Master is just finishing things up."

Riley walked to the kitchen and the men followed behind her. Her perfectly tailored sissy maid dress stuck out at her waist line, like a ballerina's tutu, exposing her bubble butt.

One of the men looked back and whispered to his friend, "I cannot wait to get in that."

Riley heard the man say that and got goosebumps... she was starting to think this night had more in store for her than she originally believed. When she got to the kitchen she started making the men some drinks. As she was taking a glass out of the cupboard, one of the men pinched her butt startling her and she dropped the glass. The glass fell in slow motion. It hit the floor, shattering into a thousand pieces. The room fell silent, all the men staring at her.

Master appeared suddenly and looked very upset. "Come here sissy". He aggressively grabbed her leash and marched her downstairs. What Riley saw was one of the best looking dungeons she had ever seen. It was a large, dimly lit room with red lights. There were numerous toys, whips, flogs, and dildos in display cases mounted to the walls. There was a bondage table, a St. Andrew's Cross, a padded cage, a queening throne, everything you could want or imagine. In the center of the room was a padded pillory with ankle spreader bars at the base. The rest of the room was filled with black leather couches that formed a "C" centered around the pillory.

Master led Riley to the pillory and said, "You are already going to be spending most of the night here, what's another hour? Put your head and wrists in the notches."

Riley obeyed without hesitation. She did not want to piss off Master anymore. Once she was settled, Master lowered the upper block and grabbed two thick padlocks, one for each side. He looped each padlock through the metal loops and Riley was secured in the pillory with no chance of escape. Master took the two pillory keys and added them to the key ring she gave him before. Master moved behind her and grabbed Riley's left foot and restrained it to the spreader bar and then did the same with the right. He quickly adjusted the front of the pillory down, bringing Riley's upper body lower so her sissy pussy would be up in the air and more exposed. Master moved behind Riley; she could not see what he was doing, but she could hear him rummaging around in a drawer. She heard two very distinct noises... the snap of a latex glove being put on and a glass bottle being set on something hard. Master walked up behind Riley and pulled the butt plug out of her sissy pussy.

Master walked up to her front and said, "Good sissy keep their toys clean." and shoved the plug in her mouth. Riley sucked on it not caring for the taste. Lucky she kept herself very clean so it wasn't terrible. Master walked back and Riley heard him set the plug on the table. He walked back and Riley could feel lube being applied to her sissy pussy. Master worked in a much, much larger plug and walked back to the table. Riley heard a button click and then the plug started to vibrate randomly. Riley started to pant... it felt so good.

Master walked back up to Riley and had a damp cloth with a fastener attached to it. He placed it under her nose and tightened it around her head. Riley immediately felt the effects of the poppers and it made her sissy pussy tingle... that and the plug felt amazing.

"Don't worry. You will still be punished for embarrassing me in front of my guests. What type of maid cannot serve drinks? I did this because I still want you super horny for the event later... but... you still need your punishment."

Master pulled a blind fold from his pocket and placed it over Riley's eyes. He walked back behind Riley and she heard him grab something.

"You broke that glass in front of... how many people? 14? 15? I think 15 lashes with the cane will be fair."

Just as Riley was about to protest WHACK came the first strike. Riley screamed out. It didn't really hurt but caught her by surprise. The panties partially covered the edges of her butt cheeks where Master accidentally hit.

"Tsk tsk tsk.. I appreciate the crotchless panties but thinking about it, I don't think you will need them tonight."

Master walked over, cut the panties off, and shoved them in Riley's mouth. He took a piece of duct tape and secured the panties in her mouth.

"I better not hear another a peep."

Master proceeded to cane Riley 14 more times, and let it be known, those 14 made solid contact every time. Riley was a sobbing mess by the end of it. She had been spanked before but never caned; her ass was welted and on fire. Despite the amount of pain she was in, she was still turned on from the poppers and vibrating plug.

She heard the sound of people walking down the stairs and could feel the room fill up. She couldn't see but it felt like way more than the 15 people she thought was upstairs.

"Everyone please find a seat, I almost have her ready."

A minute passed by and Riley heard everyone take their seats. It started to quiet down but Riley could feel a bunch of eyes on her. Master walked around and did one final check, tugging on the padlocks and making sure everything was secured.

"Thank you everyone for RSVPing online and showing up on time. It looks like all 25 made it. I am glad you can join me for this wonderful evening. Welcome to Sissy Riley's first gang bang. She can't really say anything right now but I know she is excited to be here with you all!"

"Gang Bang?! 25 People?!" Riley thought. She had casually mentioned to her master she wanted to do one but didn't think he would organize one on the first night!

Master continued...

"Now you see... my time, energy, and equipment has run Riley a pretty significant debt. Lucky for her, I don't care about money and... lucky for all of you, I love to share! I was thinking about ways how Sissy Riley could pay for the services and I have come up with a fair exchange. There are 25 people here tonight. One session with a sub and I will cum at least four times. So I was thinking 100 happy endings for the group would suffice, no?"

Riley heard the crowd of guys start to chatter and could feel the energy in the room increase drastically.

"Our Sissy here was not a very good maid to start the evening. She told me she was trained but I had to answer the door for five of my own guests; she hardly served any drinks... broke a glass... so I believe a punishment is needed for her. She has already been caned for the broken glass so the remainder of her punishment will be two part. When you reach completion, I ask that you dispose your cum in one of our collection bowls. Her first punishment will be to drink the collected cum of every guy here. Who knows, maybe it won't be much of a punishment after all. Hours of getting fucked I am sure she will hungry."

Riley could not believe what she had just heard. She was both nervous and excited for the gang bang but did not agree to drink 100 loads of cum before she got there. (Even though she did love the taste of cum) She could hear the guys making jokes and heard some belts being undone.

"For those of you who were not served a drink by our Sissy tonight, you may grab a paddle and administer ten spanks on her ass if you wish. You will need to be quick with this because we will want to keep the line moving so spank her hard and spank her fast."

"Ten spanks?!" Riley never even had a chance to get drinks! Between the guests constantly arriving, Jerome asserting his dominance, her butt being pinched in the kitchen... drinks were not really an option.

"The flow of the night will go like this; we will pick numbers to determine the order. You can use her mouth to fluff and get hard. You will then use her sissy pussy until completion. Please deposit your cum in the appropriate area, administer spanks if you want, and please wait for your turn again. We will have a collection bowls placed under her mouth and sissy pussy. Do I have any questions?"

Everyone seemed to have a good understanding of the evening and started getting ready for their fun. Master approached Riley and knelt in front of her. He pulled off the duct tape and pulled her panties out of her mouth.

"Are you ready Sissy? I hope you will enjoy this night. I know I will."

As he was talking, he grabbed Riley's cheeks and scrunched her face to make her lips pop out. Master pulled out her lip gloss and bit the tube to hold it. With his free hand he unscrewed the brush and applied lip glass all over Riley's lips.

Master removed the blind fold and Riley saw a huge crowd of people. Men of all shapes and sizes were in different stages of getting undressed. The only common theme was black ski masks covering their faces.

"Oh my god..." she thought "This is about to happen!"

She looked to her left and saw a man setting up a tripod. She had not agreed to be recorded either!

"Master... I didn't know this was happening and now it's being recorded; I am not sure I am comfortable with that."

Master smiled, stood up, and looked around.

"Who has number one? Has anyone picked it yet?"

A man standing near the front in his only underwear spoke up,

"I do"

"Good. Can you do me a favor and plug this hole?" Master said pointing at her mouth. "This sissy doesn't seem to realize she has no control over anything here."

That statement turned Riley on so much but also shook her to her core. Riley learned real quick wanting to be helpless is one thing, being helpless is another.

The man walked up and jammed his cock in Riley's mouth. As the man was doing this, Master removed the poppers from Riley's nose and went back to the table behind her. Riley heard the glass bottle get picked up and put back down. Master returned to her, this time with two wet cotton balls.

"Here you go Sissy, I know sissies love their poppies. Makes there little sissy spot tingle doesn't it?"

Master chuckled as he shoved one drenched cotton ball in each nostril. The man was still thrusting his cock in and out, in and out. Riley could feel it growing in her mouth (which turned her on so much) and felt he was almost ready.

Master walked behind Riley and lubed up her sissy pussy.