Room 220 Ch. 02: Fantasy Request

The first time Sandy and Tyler met, he was expected to be the dominant one of the couple. That was the manner he portrayed while they chatted online for years. When they first met however, he was no where near the dominant she. She ended up being the dominant one, and she humiliated him for it.

After that first meeting, she never expected to hear from him ever again. That was until the very next afternoon when he logged into his computer and immediately contacted her.

"I'm sorry."

"I know you are."

"I understand if you never want to talk to me again."

"I haven't decided yet."

"Ok."

This is exactly how Sandy left him for over two weeks. Alone, missing the first woman he's ever loved, humiliated that she considers him pathetic.

He continued to log into the chatroom they previously spoke in everyday, in hopes that she would return. It took a while, but one day she did return. She immediately sent him a private message.

"You know you can no longer call yourself a dominant right."

"I know."

"From now on, it's Yes Mistress."

"Yes Mistress." Smiling when he typed that out because he thought it meant she still loved him.

"I own you now."

"Yes Mistress."

"Are you sure you understand?"

There was a long pause before Tyler answered her. She sat there while is avatar simply blinked, the only way she knew he was still there and typing.

"Sandy, I will do anything you ask me to. If you tell me to jump I'll jump. If you tell me to shut up, I'll shut up. I'd rather be your submissive than to lose you because I suck at being a dominant. These past two week have been hell, I've missed you so much. You were part of my daily world, we talked about everything, and then after one night, you were gone."

"No Tyler, it's not going to be that simple."

"What do you mean?"

"I mean, that you've ruined everything, and now I have to be the one making the decisions!!!"

"I'm sorry, I'll try harder if you want."

"No you're done. I own you."

"I want to be with you."

"Then say it. Tell me I own you."

"You own me."

"No! It's Mistress You Own Me!"

"Mistress You Own Me." Smiling because he thinks she trying to scare him.

"And you're going to do anything I tell you to."

"Yes Mistress."

"Anything!"

"Yes Mistress."

The two of them spent over an hour chatting, redefining who they were to each other, how they would behave, before they started talking more about life like they usually did.

The last two weeks were a lot more interesting for Sandy than they were for Tyler.

She ended up telling him how after she told a few of her friends about him, how pathetic he ended up being, and how she had to be the dominant one, they challenged her to the same.

She spoke of a night with her and her friends in that same hotel room, and how one girl was left on the floor crying. She had used a strap-on dildo on her and before she was finished, the girl was crying out in pain. No one cared either.

Sandy didn't know or intend to, but this story was a huge turn on for Tyler. A room full of dominant women sounded like fun.

The last time he saw Sandy, before she threw his naked ass out of that hotel room, he had his first sexual experience ever. She and their friend beat on him, stripped him, made him fuck a girls feet just to have a ruined orgasm, and then lick his own cum off the floor, and yet he still remembers it as a good night.

"Would you be surprised to find out that would be a turn on?"

"Of course not."

"Really?" Actually a little shocked at her answer.

"I've already told them how pathetic you are, of course they'd want to watch me humiliate you again."

"Oh."

"What did you expect, a room full of woman that want to have sex with you? No, most of them are gay. They just want to watch me beat your ass again and help humiliate you some more."

"It still sounds like fun." Honestly worried about how much more humiliation she could give him.

"Ok then, on Friday, I'll pick you up early and take you shopping with me, and later that day, we'll meet up with them."

"Sounds like a date."

"We don't date Tyler, I only date real men, you are not even a man. A dick in your mouth is the closest you'll ever be to a real man."

"I understand." Completely in shock that she's envisioning him sucking another mans dick.

"It's Yes Mistress Tyler, if I have to tell you again I'm going to make you regret it."

"Yes Mistress."

Sandy immediately logged of for the night. She had enough him for the night. So he logged off too. There was no reason to wait on someone who wouldn't be back.

It was Friday before Tyler heard from Sandy again. It wasn't on the computer either, she was outside of his place to pick him up. It was only eleven in the morning and he wasn't expecting her. Luckily he had already showered and was dressed but still not expecting her so soon.

She took him out for breakfast at a regional southern cooking restaurant. A small chain known for their home cooked meals. The two of them simply ate and enjoyed a normal conversation. Nothing about dominants or submissive or anything sexual at all, just life. It felt like a date to Tyler. Sandy even paid for him.

Next she took him to Macy's, a clothing stored that he's been too but never shopped at. Their prices are a little high for him. She took him straight to the mens underwear section. The first thing she picked up was a pair of black silk boxers.

"This is what you're going to wear today."

"Ok." Reaching to take them from her hands.

She smacked him across the face, before he even touched them.

"It's Yes Mistress!"

"Yes Mistress." Holding his hand to his cheek trying to soothe the ache.

"Now every time I tell you to wear these, know that I'm going to hurt you."

"Yes Mistress."

"Good now follow me." As she threw the boxers towards him to catch.

She walked towards the mens sections, picking up a bag of black socks and tossing them back towards him to catch. She went straight towards a rack with Levi 357 blue jeans hanging on them.

"What's you size?" Already looking through the rack.

"Thirty six thirty."

She back handed him across the same cheek. Never looking up from the rack.

"Thirty six thirty Mistress." Knowing exactly why she hit him.

"Skinny little fuck. You need to eat more." As she pulled a pair of jeans from the rack and placed them into his arms.

She then walked over towards another rack with button up shirts on it.

"What's your size?"

"Medium Mistress."

"You're learning." Smiling while still tossing through the different shirts.

"Yes Mistress."

She pulled a black button up shirt from the rack and placed it in his arms. It was nicer than any shirt he owned, it looked like a shirt you'd see with a tux, not a pair of jeans. She then led him to the shoe department.

"What's your shoe size?"

"Eleven Mistress." Quietly as to not be heard by the sales women.

"Louder!"

"Eleven Mistress." Knowing the sale women has to be able to hear everything their saying as she walked up.

Sandy simply picked up a dress shoe from the wall and handed it to her.

"Can I see this in a size eleven please?"

"You sure can, I'll just get them from the back."

"Thank You." Smiling as the women ran off to get the shoes.

"Sit Down." Pushing him down on a bench next to him by the shoulder.

"Yes Mistress." His hands still full from everything she has him carrying.

The two of them didn't talk until the sale women returned. She immediately saw Tyler sitting and pulled up a stool in front of him. She began to untie his tennis shoes and put on the new black dress shoes.

Sandy smiled when she was done. "We'll take them."

"Great, would you like me to ring you out back here?"

"Can you ring out everything?"

"Yes Ma'am, and there's no wait."

"That will be great thank you."

Tyler didn't say a word while the women rang up all of his new stuff. He just stood there in shock when the number popped up as the total. Sandy was spending over three hundred dollars on him, on one outfit. That's more than he spends on a years worth. She simply pulled a credit card from her purse and paid for it like it was nothing.

When the sales woman presented Sandy with a large bag full of his new clothes and shoes, simply passed it back to Tyler.

"Get changed." Pointing towards the dressing room off to their right.

"Yes Mistress." Loud enough for the sale woman to again hear as he scrambled off.

Sandy simply smiled and took a seat on the bench until he returned.

It took close to ten minutes for him to come out of the dressing room. Wearing everything she had just bought him. Carrying the same bag with his clothes now in it. Sandy immediately got up and untucked his shirt roughly.

"You don't tuck a shirt into your Levi's"

"Yes Mistress."

"Are your clothes in here?" Looking inside the bag.
 "Yes Mistress."

She immediately opened the bag and removed the receipt for her purchase and the opened bags of socks and placed them on the sales woman's counter.

"Do you have a smaller bag for these?"

"I sure do." With a smile as she reached under the counter and pulled out a smaller bag and began placing the items inside of it. "Here you go."

"Thank you." Taking the smaller bag from her. She then placed the larger bag with Tyler's belongings in it on the counter. "And do you have a trash can you can throw these in?"

"Sure right here." As she pulled a trash can out from behind the counter and placed the bag in it for her.

"Thank you, you've been so helpful today."

"You Welcome. Thanks for shopping with us today." Smiling as she has repeated that very line for the millionth time.

Sandy simply turned to leave, seeing a blank look on Tyler's face. He didn't say a thing, even though she just threw away his clothes and his only pair of tennis shoes.

"This is how you dress now."

"Yes Mistress." Following behind her as she headed out.

Sandy had one more stop in mind before meeting with her friends. She took him to a store called Hustler Hollywood. It's the largest sex store in the area. Literally visible from the interstate. If there's a sex toy you want, they've got it. When they got there she forced him to wait in the car while she went in alone.

Tyler spent close to half an hour out there while she was shopping inside. He was completely curious as to what she was buying.

He got bored quickly and decided to stand outside of her car, smoking a cigarette, watching customers come and go. He even had the time to notice something he found humor in. All the customers that went into the store had their head up as they entered, however when they left, a majority of them had their heads down, as if ashamed of what they had just purchased. He found it funny.

When he saw Sandy coming out, her head held high with a snarky little smile and carrying the largest bag he had seen anyone exit with, he put his cigarette out and got back in the car. She placed the bag in the trunk of her car and got back in the drivers seat.

"Are you ready for this?" Grabbing his crouch tightly, causing him to jump, his hands grabbing on to the sides of his seat.

"Yes Mistress." A squeal of an answer.

Sandy simply smiled and released him. "Good. Then lets go." Starting the car and heading to the hotel. The same hotel where she humiliated only weeks ago.

The bag from Hustler was left in the trunk when she took him to the exact same room, number 220. As she opened the door, he could see three other women already inside. When he entered and she closed the door, she immediately began his humiliation.

"Kneel." Pointing at a space on the floor against the wall near the door.

"Yes Mistress." Taking his place against the wall, looking at everyone in the room, whom he'd never met before.

"Do you have one of those for me?" Pointing at a glass of Mimosa sitting on the bed side table.

"Of course we do." The soft voice from the girl sitting in the chair off to the side, as she got up and pulled the ingredients out of the small fridge next to the tv. Quickly making Sandy a mimosa, served in a champagne flute.

"Perfect. Thank You." Taking a fresh glass from her hands. "Are you ladies ready to have some fun?" Smiling looking back at Tyler.

Two of the girls began to laugh at him.

"Well let's have some introductions then." Walking back towards Tyler. "Now you all know Tyler now. How do you like his outfit? I picked it out myself."

The women all seemed to like it even though not saying a word, simply nodding their heads with approval.

"Now Tyler, this is Becca." Pointing at the smallest and youngest girl in the room sitting in the chair next to the bed. She's a beautiful chunky women, wearing a black dress, black boots, and black hair. She's wearing a lot of gothic jewelry. She's young enough that if they lived in the same town they might have attended high school together. She simply nodded at him when she heard her name.

"That's Trica." Pointing at a larger woman sitting furthest from them on the bed, also wearing a black dress but barefoot, and with blonde hair.

"And thats Brandy." Pointing at another big women on the bed, whose also wearing a black dress, black panty hose, and her hair is also died black.

"It's nice to meet you guys."

Sandy immediately smacked him with the back of her fingers as he knelt there. "Did I tell you to talk?"

"No Mistress."

"Then shut up!"

"Yes Mistress."

Brandy chimed in, "Did you get the toys?"

"Would I be here if I didn't?"

"Well I don't see them."

"They're in the trunk of my car." Taking a sip of her mimosa while reaching into her purse for her car keys. "Becca will you be a doll and go get the bag out of the trunk of my car?"

"Sure" Quickly jumping up and grabbing her car keys as she went out the door, leaving the secondary lock open so the door wouldn't completely shut and lock her out.

"Thank You." Watching as Becca walked out the door. "I didn't really want to be seen carrying a huge bag from Hustler." Chuckling with the Trica and Brandy.

It wasn't long before she returned, carrying a Hustler bag, almost half her height in size.

"Thank you little one." As she grabbed the bag from her hands and placed a soft peck on her forehead. Becca simply smiled and headed back to her seat.

"Ok ladies, Tyler did make one request for today. He's requested to be blindfolded for most this adventure, and since he has no idea what's inside of this bag, I think now is as good a time as ever." Placing the bag down on the bed and pulling out a new black leather padded blindfold. She broke off the sales tag with her hands and placed it over Tyler's eyes, tying it tightly behind his head.

She took a step back and kicked towards his face, leaving about a foot between her boot and his face. He didn't budge.

"Good, he can't see us." Smiling back to the other women. Now let me show you guys what I got us to play with."

She first pulled out a black leather cat-of-nine, with a large handmade handle.

"Oh I want that!" Trica let out as she was reaching for it out of her hands.

Next she pulled out a black leather riding crop, about two feet in length. "I got this for you Becca, I think its just fits you."

"Thank you." Softly as she accepted it as a gift.

"You're welcome." Again kissing her forehead before returning back to the bag on the bed.

"This had your name written all over it Brandy." Pulling out a purple and black nylon strap-on dildo. Tossing it into her lap.

"On yes it does." Laughing while picking up the box and opening it up. "How's your bottom feeling Trica?"

Trica hit Brandy softly on the thigh. "Shut up, that's not funny, it really hurt."

Brandy just sat there giggling, pulling her new toy out of the box.

Sandy then dumped the remaining items onto the bed. There was a matching purple and black collar, wrist restraints, and ankle cuffs. A large container of lube, a silver leash with a black leather handle, and a box with restraint chains and locks in it. The last thing out of the bag was a black leather open mouth gag with a large stainless steal ring towards the middle of it. "I think we can guess who this is for." Giggling with the other girls.

She handed the collar over to Becca, the ankle cuffs to Trica, and the wrist restraints to Brandy.

"Bitch! Stand Up." Looking over towards Tyler.

"Yes Mistress." Immediately getting up. Not knowing what to expect.

Sandy grabbed him by the front of his shirt and led him to stand closer to the bed but far enough away, that there was room to walk freely around him.

"Strip!"

"Yes Mistress." As he reached down and began removing his new shoes. Standing back up and removing his new button up shirt, allowing it to fall to the floor beside him. Unbuttoning his jeans and allowing them to fall to the floor as he stepped out of them, again placing to his side with the shirt.

"Stop!"

"Yes Mistress." He froze in place.

"What did I tell you about wearing your black silk boxers."

Tyler paused in thought for a moment before he answered. "That's I should expect you to hurt me Mistress."

"Good answer, you do have a memory." Still smiling back at the girls, proud that he remembered even though it was meant to humiliate him. "Take your socks off."

"Yes Mistress." Quickly removing his socks and placing them on the same pile.

Sandy smiled and looked over at the other women. "Ladies, do you want to leather him up?" Softly laughing at the end. She picked up his clothes and began to fold them and place then on top of the television so they didn't get wrinkled or messy.

Brandy and Trica immediately started to place their ankle cuffs and wrist restraints on him without saying a word. Becca waited until they were finished and placed the collar on around his neck.

"Now for the Pièce De Résistance." As Sandy picked up the the open mouth gag from the bed. The others simply giggling. Tyler has no idea what she's talking about but he can feel its going to be humiliating by their laughs.

"Open your mouth!"

Tyler immediately opens his mouth.

"Wider!"

Lost in what to expect Tyler slowly opened his mouth as far as he could.

Sandy inserted the stainless steal section of the gag into his mouth. Causing his mouth to stretch as far open as he could. She then belted it behind his head as tight as she could.

She stuck her finger in his mouth and quickly tapped on his tongue. "No I can shove anything I want in here." Giggling in his face. "Are you ready for this?"

"Ys Msstrss." He gurgled out unable to talk properly.

"No more talking until I tell you otherwise."

"Ys Msstrss." Again gurgling and starting to drool.

"Place your hands behind your head."

Tyler immediately complied, placing his arms behind his head.

"Brandy and Trica, grab his arms and keep his legs spread open. Becca put this on him and make sure he doesn't try to pull away." As she handed her the leash.

Trica and Brandy both grabbed his wrist behind his head and applied pressure to keep him from being able to pull them away. They then placed their legs in between his, forcing him to stand there with his legs spread as far as he could while still standing. Becca quickly put the leash on and held it taut from behind.

Sandy walked up to Tyler and grabbed him firmly by the balls. "These are mine and I'm about to show you what I like to do with my balls." As she laughed and let them go.

She took a step back and kicked him squarely in the crotch, still wearing her Dr. Martens. Tyler jumped and moaned in pain. All of the women in the room laughed, aside from Becca, she just silently held tight on his leash.

Sandy kicked him again, causing him to jump again.

Again, she kicked him, harder than before. He's no longer holding himself up, Brandy and Trica are supporting his entire weight.