A Room Full of Regret

As he first entered her, Malik wanted to just drive his cock into Ruth, but he lay still, allowing her to push herself down on him. She began slowly rising and falling, going in a little deeper each time, spreading her thick juices out onto his shaft until she was all the way in. The feeling was different than he was used to. When she pushed down, the condom felt like it was closing around his cock head, squeezing it a bit and trying to push him back out. It didn't slide naturally the way Deirdre's pussy did. Still, it did feel good. Ruth was tight, even tighter than Deirdre. He loved the feeling of her strong legs around him. Even her tiny tits were fun. He could hold the whole thing in his hand. He could feel her juices running out onto his balls. After a little while, he didn't even notice the restrictive feeling around his cock head any more. It just felt better and better.

Deirdre admired Ruth's ass. It's so hard, she thought, it doesn't jiggle at all. She's not like a normal girl. As she watched, she realized that the condom had broken. There was a section of Malik's cock near that head that was visibly uncovered each time he pulled out, and with each stroke, the condom pushed further down until it was just a ring around the base of his cock. It looked so much better without it, she thought. His dark shaft was beautiful and dangerous.

Oh my god, though Deirdre, he could cum in her. He could knock her up. Neither of them would be any the wiser until it was too late. Deirdre didn't want that, of course, but she was transfixed, too turned on to speak. Instead, she started playing with her own pussy.

"Stop," said Mary, "The condom's broken!" Malik stopped immediately, but he had to hold Ruth still to pull out of her.

"Did you use an oil-based lube?" asked Judy, "Oils just melt condoms."

Deirdre was embarrassed. "I used lotion," she said.

"Here, use this," Judy pulled some lube out of her purse and handed it to Deirdre, along with the last condom.

"I'm so sorry," said Deirdre to Malik or Ruth or maybe the whole room as she pulled off the useless rubber. She squirted a generous glop of lube on Malik's cock, rolled a new condom on, and aimed it back at Ruth's waiting hole.

While everyone was watching the action, Kathy quietly turned over the hourglass, which had been almost empty. It seemed fair, she thought. They had started over. Besides, it was so sexy watching the supposedly pure Ruth getter reamed by her new dark lover. She was only sorry he hadn't cum in her while that condom was broken. It would have been hilarious for her to get pregnant by him.

This time, the new lovers started quickly. Within a few strokes Ruth was bouncing up and down on Malik and he was driving into her forcefully. Ruth had never dreamed it would feel so good. She was kissing Malik's soft full lips while her hand reached between them and began playing with her clit. She wanted to cum now. It would make the whole thing complete.

"I'm going to cum soon," Malik warned.

Ruth let out a gasp. She was so close. She just wanted him to last a few more minutes. But it was too late. Malik grabbed her by the hips and pulled her down onto him, holding her there while his cock throbbed. It felt very good to her, but she was still craving her own release. She rolled off of him onto her back and continued playing with her clit.

Deirdre slid her hand up Malik's cock, stripping off the condom. A river of his juices spilled out onto her hand and down into his pubic hair. She leaned down and took his head into her mouth, gently -- she knew he was sensitive after he came.

"Oh dear, dear Deirdre," said Kathy smugly, thinking she had just said something clever, "You're going down on the wrong one. I dare you to give Ruth the orgasam she really needs."

Without hesitation, Deirdre slid down between Ruth legs. She had never gone down on another woman before, but it seemed like the most natural thinh to do after sharing her man with her. Ruth's vagina was gaping open lewdly after her mad fucking. Deirdre licked all around her hole and up to her clitoris, pushing Ruth's hand aside with her nose. Then she began to lap at it quickly.

Ruth was overjoyed. This was even better than her fingers. The tongue was fast and had just the right amount of roughness to it. She just wanted to be filled at the same time.

"Use your fingers," she begged.

Deirdre rubbed the outside of Ruth's hole, up and down. She had completely forgotten that her fingers were covered with Malik's sperm. Even Mary had failed to notice this time. Only Kathy saw Ruth's danger as Deirdre's fingers circled the outside and then slowly began going in. First one finger, then two, and finally three started jamming into Ruth's hole, pushing more and more semen right into her fertile pussy. That, combined with the relentless licking brought Ruth to a higher and higher level.

Suddenly, she went tense. She had been building to this for a long time, and now she finally got her release. Every muscle in her body tightened and then shook. In a moment it was more than she could stand. She had to grab Deirdre by the hair and pull her face off of her mound.

"Oh my god," was all she could say, "oh my god. Oh my god. Oh my god."

She lay there for a minute or so. Deirdre crawled up the bed so that Ruth was sandwiched between Malik and herself. Then she hugged both of them, kissing Malik, letting him taste Ruth juices. A feeling of pure love filled her. She thought about Judy and Chris keeping a woman as a pet. Maybe she and Malik should do that with Ruth.

"Isn't that sweet," mocked Kathy. She seemed to have decided that she was completely in charge now and was drunkenly giving out orders. "Charlie" she said, "it's your turn. I bet Mary would love to fuck that big cock of yours."

Charlie felt awkward. It was be really weird to have sex with his friend's girlfriend, but he also didn't want to offend Mary or Josh by rejecting her. Besides that, he was horny as hell from everything that had happened already. Ruth had taken the edge off of him, but he was already hard and ready to go again.

Josh saw his friend's hesitation, and understood it. He wasn't exactly happy about this latest turn of events. Charlie was his close friend. They were going to see a lot of each other, and this could get awkward going forward. On the other hand, he knew that Mary had let him try to have sex with Judy. As humiliating as that had been, he didn't feel like he could fairly deny Mary this chance.

"If you want to, Mary," he said, feeling galant, "just wear protection."

Mary was shocked. This whole evening was more than she could really handle, and Josh agreeing to let her have sex with another man seemed unreal. Still, she had to admit she wanted to know what Charlie's enormous cock would feel like. If she didn't act now, she probably never would.

"OK," said Mary blandly. She didn't want to give away how eager she was. Mary had always had a bit of a crush on Charlie. She loved his sense of humor, and anyone could see that he was much more handsome than her boyfriend. Now, having seen the monster tool he had to work with, she was naturally curious. She loved Josh, but he HAD just fucked Judy, after all...

"How do you want to do this, Mary?" asked Charlie, after first looking Josh in the eye to make sure it was really OK with him.

Mary crouched down on the bed, with her knees below her chest and her ass sticking out just past the edge of the mattress. She liked this position with Josh because she could really take advantage of the whole length of his cock. It also held her pussy tight, and she wanted to feel Charlie's huge cock really stretching her out.

Charlie went to his pants and pulled a gold-colored condom out of his wallet. He tore it open and rolled it down onto his shaft. The extra large rubber was big enough for even his long thick penis.

He leaned over Mary's back and ran the head of his cock over her slit and on into her pubic hair. He slid it back and forth, smearing her wetness around. Then he whispered in her ear, "You've always wanted this, haven't you?"

Mary nodded. Charlie bit her on the side of the neck, working his way down to the top of her shoulder and then back to her ear. Mary realized she had been desperately wanting Charlie to bite her neck again. She felt her skin tighten up, and Charlie must have felt it too. He reached down and started pinching her nipples. "Do you want me to fuck you right in front of your boyfriend?" he asked.

She nodded again, a little more vigorously this time, and grabbed his cock, aiming it toward her dripping gash. He was still sliding back and forth to tease her, but she managed to line it up with her pussy.

"You slut," he whispered. She shuddered, and then she felt him pressing into her. God, she FELT like a slut. She was completely out of control, letting her boyfriend's best friend fuck her right in front on him and all these other people. Some of them were really complete strangers. She would never have believed it of herself, but now she didn't think she could stop.

She pushed back onto him as much as she could. The position she had chosen didn't give her a lot of freedom of movement. She mostly had to just lie there and take it. I'm really just a fuck doll, she thought, and she loved it.

Charlie took full advantage of her helplessness. He began pressing deeper and deeper into her. Mary had never felt so full before, and it was driving her crazy. She reached one hand between her legs and began playing with her clit. She could feel a climax coming. She wanted more.

"Fuck me," she thought, "Fuck me harder. Harder. Harder! I'm going to cum." She realized that she wasn't just thinking it. She was screaming it. Someone could probably hear it in the hallway. She didn't care. She was finally cuming. She had wanted to do that since she had sat on Chris's lap.

She froze. Charlie pushed deep into her and held there. Was he coming too? She was sure that he was. He just held deep inside her as her body clenched and shook. Then, as she was starting to come down, he began fucking her again. He hadn't cum after all. He just held there so she could enjoy her own climax. Now, even though she stopped touching her sensitive clitoris, she was building up to another. Again, Charlie pushed deep into her and held there. Was he cuming now?

"Sorry, that's time," said Judy.

Mary, continued to shake for some seconds. Then slowly Charlie pulled out of her. She looked back at his cock. Clearly, he had not cum. Mary idly wished that Josh could last more than five minutes. Maybe she would need to try Charlie again, she thought.

"Did you cum, Charlie?" asked Kathy, sounding Kind.

"Not this time," said Charlie, "I mean I already came once with..."

Kathy cut in as if he wasn't even talking, "You know who else hasn't cum yet? Chris. Josh, suppose you give him a little blow job to help with that?"

The humiliation just never ends, thought Josh. He was too drunk to even consider not doing what he was told. Instead he just knelt in front of Chris and got ready to do his duty.

Chris was annoyed with Kathy. He was starting to hate the whole game, and how it seemed that everyone wanted to make him do something homosexual. He was even a little irritated that Judy didn't take a drink to get him out of it. After all, she never needed to drink for herself any more. She seemed to enjoy watching him being humiliated. Of course it was a point of pride that he never backed down from a dare, so he never even considered taking the drink for himself.

Instead he sat there and passively let Josh put his cock into his mouth.

Josh remembered everything Judy had said about the best way to give head. He did a sort of halfhearted attempt to follow her directions, but really he wasn't interested in learning to do it right. He had no plans of going down on another man in the future and really didn't want Chris cuming in his mouth.

Josh's mouth felt good on Chris's cock, of course, but he was used to getting head from Judy, and she was an absolute expert. When Judy called time again, he was still not all that close to cumming.

Judy piped up, "Let's see, after Josh... I did a little blow job... Chris just did his with Josh, sorry baby... Ruth did hers with Malik and Deirdre. Kathy, your turn."

"Kathy, I dare you to fuck Chris," said Clara. Her lips curled up into a cruel smile.

"OK," said Kathy. She was really looking forward to this. There was something that drew her to Chris like a moth to a flame. It was really unfair of him to be so attractive. Something about it bothered her, but in her drunken state, she couldn't remember what. "Can I get a condom?" she asked.

There was a moment of confusion as everyone realized that they had used up the ones Clara had brought. "Do you have any more, Charlie?" asked Judy finally.

"No, I just carry around the one, in case of emergency."

"Well, I guess I can't do it then," said Kathy, unable to hide her disappointment.

"Oh sure you can," simpered Judy, "Chris can pull out on time, can't you, Honey?"

"I..."

"Of course you can," she reassured Kathy, "We never use condoms, and he's never knocked me up." She neglected to mention her cervical cap and spermicide.

"Yes, but.. " said Chris.

"It will be fine," she gave Chris that look that said not to argue.

"OK," agreed Kathy. She knew this wasn't a good idea, but she was only human. She wanted to have sex with Chris. More than that, she wanted to steal him away from that animal of a girlfriend. He deserved better. He deserved someone like Kathy, and this was her chance.

"This really isn't a good idea," said Chris suddenly.

"I thought you always did your dares," Judy said, a hint of playful taunting in her voice.

He looked directly into her eyes. Why was she forcing this, he wondered. Finally he said, rather lamely, "Anyway, it's not really my dare. It's Kathy's. Besides, I just did a dare."

While he and Judy locked eyes, Clara got up and walked over to him. She whispered in his ear. Chris looked down with a hint of resignation and shrugged his shoulders a bit.

"OK," he said, "I'll do it." Judy made a mental note to ask Clara what she had said. It would be a good thing to know if Chris ever stood up to her again.

Normally, Chris wouldn't have been so foolish, but everything seemed aligned against him. Judy often pushed him into sexual situations with other women. She seemed to get off on it, and as long as he was doing it for her, he was OK with it. But Kathy was something different. She was the most attractive woman he had ever seen.

Kathy was a siren. Men would destroy themselves for her, and she would laugh gleefully. He wanted to resist her but he couldn't. It was too much. It was more than just Kathy, drawing him forward. Judy had demanded it of him, not knowing why he was so filled with conflict. She didn't, couldn't understand. And, with Clara's words still ringing in his ears, he was rushing blindly toward Kathy, ready to break himself on her.

A tiny bit of Kathy's drunken brain was telling her that this was a terrible idea. For some reason she wasn't supposed to be doing this. She told that little voice to shut up. Chris was the man she had always deserved. He was her prince charming, a man too perfect to exist, and now she was going to get him. There was nothing that a little voice could say that would turn her from her path.

Chris and Kathy met with a passion that neither of them had ever experienced before. Their bodies seemed to mesh together perfectly. He cradled her in his powerful arms and crushed her against him. She wrapped her arms around his back, her big firm breasts flattening out against his powerful chest. Her legs wrapped around his hips and ass, trapping his cock between them. Her full pouty lips pressed against his, and their mouths opened. Their tongues entwined and played together.

Chris began sawing his cock back and forth on her soaking pussy, while Kathy writhed like a mink in heat. He began to slide his body down, the helmet of his cock getting closer and closer to its mark. At last, without any help, it found its way into her.

Kathy gasped. Nothing could possibly compare to how she felt. Chris was magical. As he drove his cock deeper into her, she had never felt anything like it before. It seemed like he fit her perfectly in a way that no other man ever had or could. She was complete for the first time in her life. Her mind closed down and she gave in to her feelings. This was more than a physical ecstasy. It was a religious experience. Time ceased to pass. She would be like this forever. All of her memories vanished out of her mind. She lived for this. She had always been here, fucking Chris, and always would be.

"That's time," said Judy. It was just as well, she thought. She had never seen Chris react like this, and she had seen him with more than a handful of women. Why wasn't he stopping?

"That's five minutes," said Josh, "Time's up. That's the rules."

Chris ignored him. He was driving into Kathy harder now. He seemed determined not to stop.

"Hey, I said stop. Stop it!" said Judy. Her voice had just a hint of hysteria now. What was he doing? "Your time's up," she added feebly.

All they could do was watch as Chris and Kathy moved together. He didn't seem to be pulling out very far. With her arms and legs wrapped around him, she wouldn't let him. But he was clearly thrusting into her hard each time he pressed forward. Now he was doing it faster and faster. Neither was saying a word. They were just panting, and Kathy would occasionally let out a slight squeak.

Suddenly Chris stopped, his body thrust deeply into her and holding there unmoving. His face turned red. His body was perfectly still except for his cock, which throbbed, and his balls which seemed to jump with each pulse of his cock. At long last, Kathy and Chris released their death grips on each other.

"Why didn't you stop?" demanded Judy suddenly. Chris slowly rolled off of Kathy. "You were supposed to stop when I called time," Judy said, her voice now shrill, "Why didn't you pull out."

Kathy was confused. She felt a dribble of semen leaking out. The little voice in her head was back, telling her that this was bad. "Did you cum in me?" she asked, "Why did you cum in me?"

Clara smiled like a Cheshire Cat. "I dared him to fill you with sperm," she said.

"And I always do my dares."