Sissy Riley's First Gang Bang

"She's all ready for you."

Man #1 pulled his cock out and walked behind Riley. She felt Man #1 step up behind her. He lined his cock with her sissy pussy and pushed in. Riley gasped, it felt sooo good to have something besides a plug in her. The man grabbed her hips and started thrusting in and out, in and out.

Man #2 took advantage of Riley's gasp and slid his cock in her mouth. Man #1 must have been pretty turned on because after 30 seconds Riley could feel his cock start to twitch inside her. He grunted loud and slammed into Riley, slowing after he blew his load in the condom. He pulled out of Riley and slid the condom off his cock. He fully unrolled the condom and kneeled next to Riley smiling. Instead of dumping the cum into the collection bowl, he took the condom and tied it to Riley's garter strap.

In the mean time, Man #2 was fully fluffed and walked around to pick up where Man #1 left off. Man #3 started to walk up but Man #1 asked him a question,

"Hey dude, do you mind if she cleans off my cock real quick?"

"Yeah man, no problem"

Man #1 quickly stepped in front and stuck his cock in Riley's mouth. Riley swirled her tongue around his cock and could taste cum and her sissy pussy. She was indifferent about the taste of her ass but she loved and craved the taste of cum.

Man #1 pulled out and said, "Good Sissy. I'll be back up soon."

"Thank you Sir. It was an honor to please you."

Man #3 walked up and without hesitation slid his cock in Riley's mouth. Man #2 was going strong. His cock was slightly bigger than Man #1 and he was hitting Riley's sissy spot hard and fast, making her feel extreme pleasure. Riley's moans picked up causing her to moan right into Man #3's cock. Man #3 was ready too soon because he accidentally came right into Riley's mouth. Although it would be one less cock in Riley's sissy pussy, she was happy to taste and get a big load of cum right in her mouth. The man was slightly embarrassed and shuffled to the back of the line.

Riley started to savor the taste of only cum in her mouth but Man #2 was nearing completion and pick up the pace. The slapping sound picked up and Riley started to feel the urge to sissygasm.

"Just a little bit longer pleaseeeee!" Riley thought. Her breathing picked up.

Man #4 stepped up and followed suit, jamming his cock into her open mouth.

Riley was so close but she felt Man #2's cock start to twitch and he exploded in her. His grunts and stride slowed and then stopped. Man #4 was luckily already hard but he kept his cock in Riley's mouth for a bit more fluffing. Man #2 pulled out his cock and slid the condom off his cock. He went to Riley's left side and proceeded to tie his condom to Riley's left hoop earring. He then took his cock and quickly had Riley clean it.

"Thank you for using me Sir."

Man #2 chuckled, patted Riley on the head, and walked behind her to grab the paddle. Whack Whack Whack He struck her ten times rapidly and promptly returned to the seating area. Man #4 positioned himself behind Riley and inserted his cock. She was secretly frustrated because she was so close to having a sissygasm. She could feel a damp area in her panties building. Man #5 was a little slow stepping up so Riley took advantage of not having something in her mouth for once.

"Master..." she called out.

He walked up and knelt in front of her.

"Yes, sissy?"

"I am dripping my precious cummies in my panties and would hate to waste it. Can you place a little collection bowl down there too please?"

"Aweeee. What a good sissy! Of course I will do that."

Master grabbed a small box and positioned it below Riley's caged clitty. He grabbed another bowl and positioned it below her caged clitty. A bead of Riley's cummies dripped from her caged clitty into the bowl.

As this was happening, Man #4 was going to town on Riley. He wasn't hitting her sissy spot but it felt good. Riley closed her eyes and put her head down for a moment. She was trying to focus on all the different feelings she felt. The poppers she breathed in were doing their magic and Man #4 lasted a long time. She was lost in lust and did not realize Man #5 walked up to her. He grabbed her head and tilted it up.

"Open up" he said.

Riley instantly recognized that voice... it was Jerome. Riley opened up as wide as she could and stuck her tongue out. Jerome was gentle as he inserted his massive BBC in her mouth. It completely blocked all air from coming in Riley's mouth, forcing her to breath through her popper filled nose. The popper filled air was making Riley squirm with pleasure. She was going crazy. She angled her back so Man #4 could hit her sissy spot and bucked back against him.

Man #4 must have felt the change and began panting hard immediately. Riley was so close. If this man could just last a little bit longer! Jerome pulled his cock out of Riley's mouth and started to walk around her. As he was, Riley's sissygasm was building and building fast... but Man #4 let out one loud grunt and Riley felt his cock twitch inside her. Within seconds her sissygasm subsided. Riley was so frustrated she screamed out "Noooooo" and jerked hard against her restraints. Obviously they did not give way.

Jerome saw this and knew what had happened. He had been with many sissies before and knew when they were close. Sometimes he liked to get them to the edge and back off to torment them, but he was in a good mood. He was going to give this sissy what she wanted. He approached and lined up his massive cock. Riley could feel his presence behind her and knew pleasure was imminent. This was not her first BBC but honestly it might have been the biggest. Master looked at Riley's collection bowl and saw it was already halfway full. He emptied it into the a larger bowl and put it back.

Jerome took two hand fulls of Riley's ass and gently squeezed.

"Beg."

Jerome was a man of few words. Riley immediately started to beg.

"Please Sir please. I am begging you. Make me your sissy bitch. I want your cock so bad. I will do anything. Breed my sissy pussy please Sir pleaseeee. Fill me with your sperm. I want to worship your cock 24/7."

Tears rolled down her face. She had never been so worked up in her life. Jerome decided to make her wish come true and slowly slid his BBC into her sissy pussy. Jerome put inch after inch in her and it felt like it would never stop. Riley gasped for air and her mouth was immediately filled with another cock. She couldn't believe. Jerome was pushing more cock into her. Her eyes rolled into the back of head.

Jerome finally bottomed out and Master quickly held up his hand signaling "stop". He walked over and refreshed her poppers. Master gave Jerome a thumbs up and he began to thrust. The feeling was indescribable. If it was possible to die from too much pleasure this might have been it. Jerome was sliding almost all the way out and then all the way back in. Long power strokes over and over. Immediately Riley felt the sissygasm building. She could feel her prostate buzzing and waves of pleasure radiating to the tip of her clitty. Her sissygam never stopped building. The tip of her clitty was on pins and needles when it happened. Ounce after ounce of her sissy cummies poured out of her confined clitty. Completely limp, secured tightly in a nano chastity cage, she had just had the strongest orgasm of her life. She would have shrieked but she lost her breath (and there was another large cock in her mouth).

But Jerome was only about half way done. He just kept at it. Riley came down from on high but she was building again and she was building fast. She was about to have two earth shattering sissygams back to back... within minutes of each other. Waves of pleasure radiated all over her body. She shuddered from the pleasure. She felt her ears and pink painted toes tingle. Man #6 was close because he had his cock in her mouth for so long. He pulled it out and Riley put all her focus in bucking back against Jerome. She was panting non stop trying to stifle a scream. Jerome was real close now and grunted hard.

"TAKE. THIS. BIG. BLACK. COCK. YOU. SISSY. BITCH."

Jerome did four more pumps and his cock started shooting stream after stream of hot sticky cum. The condom broke during the fucking so when Jerome pulled his BBC out a waterfall of cum came pouring out into a well positioned collection bowl. Between Jerome's cum and Riley's sissy cummies, there was already a pint of cum and she was only five loads through the night.

The night carried on for almost four more hours. Most people left after two loads so Riley was unable to fulfill her debt to her Master. All in all, Riley brought 25 men to 67 orgasms. She had 7 condoms full of cum tied to her, 50 loads went in the collection bowl, 4 loads came in her mouth, and the last 6 she took to the face. Those who stayed watched Master feed Riley every drop of cum, one shot glass full at a time. Riley had to finish every drop if she wanted to be released from the pillory. She lost count of how many cum shots she did but she guessed it was about 100. Master told her he would go back and watch the video to count.

Most of the people had left. It was only Master and a couple of people. Riley had passed out in the pillory, cum dried to her face and hair. Master unlocked the pillory and carried the sissy upstairs. She still had a debt of 33 happy endings and Master wanted her to know it. He went into her purse and took out her lipstick and wrote a big "33" on her forehead. He took a picture and sent to her. He then carried Riley out to his car, laid her in the trunk, and drove her home. Master used her keys to unlock her front door and dragged her passed out body inside. He placed her on her bed and looked down at her cum covered, locked-in-sissy-maid dress body. He pulled the key ring out his pocket, smiled, shook his head, and put them back. This girl had a debt, and he had to make sure she would be back. Master walked out of the house grinning at the thought of her getting back to her car dressed as she was.

The End...?