Sexual Roulette Ch. 06

(This was the hardest chapter to write and special thanks goes to Victoria Penndragon, AvailableSlave4u and Brightdawn for helping me.)

Melissa took her time driving home. In her mind, she started to piece together the pieces of the puzzle that George had placed before her. She began to remember the first encounter with Roger, the delivery driver. Roger, as far as she could recall, was having intimacy problems with his wife and was only at the initial party because George promised him anonymity. The fact that Roger brought her George's dinner invitation a few days afterwards was a total shock to her even though her seduction was not exactly planned.

Then there was the afternoon with Dan in his garage. Based on what she saw, Dan was the son of one of the partners at the law firm she worked for. Based on his admission, he was unwilling to follow in the family law business and instead chose to work on classic cars. Missy's encounter with him was to allow him to assert his own will on another, which explains his taking of her anal cherry during their time together. George had obviously wanted him to explore that side of him, and of her, but was he attempting to show Dan that it was the proper thing to do or was it to encourage him to further follow his own path?

'How did he guess or know I'd even accept Dan's doing that to me," she thought as she continued driving.

'And what about Frank?' This thought came fast on the heels of her thought about the encounter with Dan.

According to George, Frank had been used and abused by his previous spouses and Missy was George's way of helping Frank get over the nagging anxiety that had become the result. As she remembered the loving way Frank had grabbed the towel for her to clean off with, she saw it as a chivalrous move.

Frank had treated her like a lady even though Missy had acted more the whore instead. Missy's mind spun as she pondered the links and all her mind could turn up was George.

As Missy arrived home from her latest invitation, George was already waiting for her. As their lips met, George could smell the tell tale scent that Missy had had some fun with Frank while he was working. The lingering scent of Frank's essence around Missy's lips told him that she had taken his chocolate monster 'head on', just as he had figured she would.

It was hard for George to deny the way Missy's new openness was a turn on for him. Even after her seduction of Dan at the garage and Roger in the back of his delivery truck, he was very excited about the prospects of what was to happen the Saturday following. Just the thought of his new girlfriend on his special table covered with the seed of five guys, including his own, made the whole thing worthwhile.

Missy slowly flipped off the black ball cap she wore and began to remove the AC/DC half shirt she had worn to allow herself the chance to relax. The time spent with Frank that night had been nice, but it was not the way she had wanted to end it. As she turned towards George, she could see the bulge appearing in his shorts already as she reached her hands up to conceal her nipples a bit just to tease him.

She started licking her lips, tasting a small remnant of George's kiss as she did so. George began to walk slowly towards her before she bent down to unzip his shorts. A few breaths later, she already had George's manhood in her mouth sucking him hard as her hands began to reach below to tickle the sensitive skin underneath. George was expecting her to be aggressive.

Missy always got a little aggressive after succeeding in one of her personal challenges and this time, this blowjob, was no different. As he felt his tool slide down her mouth and throat, he surmised that she had attempted to take as much of Frank in her mouth as she could.

George had very little time to react as he felt his own essence signal its desire to rise as well. George quietly looked down and moaned softly as Missy pulled his waist towards her. The shot was quick and expected as she swallowed George's cum then looked up at him giving him her innocent puppy dog eye look. Now deflated from her assault on his member, his tool slipped out of her mouth as she began to stand up then headed to the bedroom where she went to lie down.

George took a moment to admire the view as he saw Missy laid there, spread eagle on the bed, her arms outstretched, breasts up and nipples erect, and a warming fuck me smile across her face. Her legs were folded on the bed and slightly opened revealing her naked pussy to his view. He wasted no time in kneeling down and slurping her love juice from that juicy peach. Missy's head thrashed from side to side as she placed her hands on her breasts to pinch her nipples as George continued his attention.

The taste of her fuck from earlier that night caused him to begin to lick a little lower. He wanted to lick her sensitive rosebud and see what would happen.

His attentions made Missy squeal a bit more while his middle finger played with her anus. He could tell that someone had already conquered her in that way recently. He figured it was probably Dan cause of his constant desire to be rough. His tongue found her clit yet again and stayed there until he felt her rise and fall from her own climax. Her pussy was a welcome way to finish off the busy day he had and he climbed up the bed to lie next to his beloved for the night.

The next morning, Missy awakened to the aromas of warm coffee and freshly toasted bread. She sat up and realized that she was still essentially naked except for her miniskirt. As she went over to her closet to find a suitable outfit, she could hear George singing something. She couldn't tell what because honestly George had the worst singing voice ever. But what he lacked in ability, he made up in volume.

As she quickly found a shirt and a pair of underwear; she was still trying to determine who the final participant from the party was. Missy realized she only had one more day to figure it out and invite the person before the party if she was to complete her task. Missy made it out to the kitchen where George was wearing a red "Kiss the Cook" apron over his T-shirt and shorts. As she leaned over for an innocent peck on his lips, Missy looked at the easy breakfast George made. In her mind, she started to figure he was up to something. It wasn't long until she discovered he was.

"So, Missy, Did you figure out who is our last invitation?"

Missy looked at him as she grabbed a piece of toast that he slathered it with strawberry jelly.

"Any hints this time?" Missy looked at him with her serious game face.

"I thought I gave you enough hints."

George was continuing to be playful although Missy was massively confused. It was then that George started talking more rationally.

"You first met Roger, the Fed Ex driver. You found out on your own that he and his wife had been having a less than bountiful sexual relationship. You then met Dan, the son of one of your bosses who gave up the family business to pursue his passion of classic cars.

"Then you met Frank, a nighttime DJ who had been damaged by other women who treated him as a paycheck instead of a human being. You can see why I picked those three to join in based on their histories."

"But why did they agree to it in the first place? How did you know I was going to be so compliant?"

"I didn't." Missy looked at him, wide eyed.

"What do you mean by that?"

She could feel a slight pressure rising as her wrath began to slide a bit. Was all the openness she felt just a phase, the energetic diversion in order for George to feel better about himself?

"I meant that I wasn't expecting you to drink as much as you did and strip down the way you did. I wasn't planning on you doing anything but see the table. Honest."

"Uh huh," her wrath seemed abated for that moment as she continued to eat. She could see George a little relieved that this minor argument defused so quickly. In their past, Missy had always been a very persuasive and directed competitor, especially if she spied a weakness.

"So what are you planning today besides driving me crazy?"

Even as she asked the question, Missy had a feeling that he wasn't going to spend his day with her, especially since she knew that he had to get everything for the next night.

"I have to see a friend." This made Missy jump.

Usually, George was very open about who he met, especially if it was a name he was dropping for networking purposes. The fact he referred to this person, as a friend, was already different not to mention out of the ordinary. The rest of breakfast passed with little conversation as Missy kept trying to figure out which person George was going to go see as well as who the last guest would be. Finally, George looked at her with a goofy grin on his face.

"If you let me do something different to you, I'll reveal the last name."

This offer was both inviting and scary considering what George could have her do. Still, Missy was compliant. He led her downstairs to where the table was and there she saw something she had never seen before. There on the table was a ten-inch jelly dildo among a few other things Missy only knew about from websites. She was unsure as to exactly what George was planning, but she was shocked to see such a thing down there.

"What's this, George?" she asked taking the length in her hands like it was flesh and blood.

"This is for your training," he said simply. "Although judging by your rear's gap from last night, I guess you really don't need it."

"Oh, that. Dan was being a little rough. I liked it though."

"Good, that was part of the plan although Dan was supposed to get his shot tomorrow." The grin on George's face spoke volumes as Missy thought about the favor.

"So what favor would you like me to perform?"

Missy had always been direct, especially if something or someone was in the way of getting what she needed or wanted. George admired that about her, normally.

"Patience, my pet."

He was looking around the room as if searching for something. Finally, his eyes located a long piece of black fabric. Slowly, he placed it over her eyes as she sat there, curious as to what he was going to do. A moment later, she could feel her hands being slowly pulled behind her and tied with something that felt rigid, almost like those plastic strips the police officers use in place of hand cuffs.

She could feel how snug it was against her. The confinement was both a scary thought and an opening thought as she felt George place her on the table, but not in the way as before. She realized that her rear barely touched the table before she felt her legs being pushed open. Although she felt herself comply, she still heard George quietly telling her to spread them.

She did as she was told, allowing her usual dominant personality to stay subdued while she felt a breath along her legs. Her miniskirt was being pushed up while a tongue began to run up her legs and slowly along her clit. George seemed to be taking his time as his tongue continued doing nothing but running over the bare surfaces until she could feel herself moistening.

As she continued to moisten, she could feel his tongue slowly inching towards her rosebud once again; and soon it was sliding slowly in. This sensation made Missy gasp, especially when she began to imagine that maybe it wasn't George, but Frank performing this tongue exploration on her.

She then began to imagine Roger and Dan stroking their dicks above her face while this was going on. The thoughts of this quickly started bringing her to the edge until she could hear George telling her he was flipping her over. As her chest and stomach made contact with the table, she could feel the moisture of her private area, which was still exposed to the air, begin to chill slightly as George's hand slowly grazed her left buttock.

There was a slight pause as Missy wondered what George was going to do until she began to feel the jelly dildo slowly attempt to gain entrance into her exposed rear. As a portion slowly slid past the ring, a finger slowly rubbed along Missy's pussy lips. This action alone seemed to relax Missy as she moaned contentedly before feeling more of the intruding silicon entered her.

As fast as this all started, Missy could feel herself release again before the silicone was removed and replaced by something that felt more real. Missy surmised it was George taking advantage of the situation. Missy could feel his dick inside her pulsating as his hands roughly grabbed her hips. She started breathing heavy and moaning as her man took her, treating her like the slut she felt like.

She started begging him to cum in her ass, talking like a true harlot. Before she had the chance to say more, she could feel him empty his load into her. He paused inside her for a few minutes before he slid out and slowly undid the strap around her wrists. It was then that Missy undid the blindfold and saw George with a huge smile on her face.

"Never knew you loved anal, love," he responded as he leaned in for a kiss. Missy turned away. George looked at her in alarm until she turned back and kissed him.

"Clue please," she said quietly as George reached into his front pocket of his shorts and pulled out a business card.

"Go here for lunch. When you see Jose, tell him I sent you." George smiled as he headed back up the steps.

"Will you be home by dinner?"

Missy paused for a second.

"Yes, are we going Italian again?"

George laughed. "We'll see."

Quickly, Missy ran upstairs and began to search for the proper outfit. Jose was going to get her best invite yet.