Girl's Night

As it was evident that Billy was struggling to take the big cock in his ass Ally paused for a bit, letting him adjust to the size of it. Once he has stopped struggling against it, she pushed again and this time she didn't stop until the entire length of it was buried inside of him. Billy screamed and cried into Josephine's cunt as he felt like his ass was going to split in two as the intruding rubber cock slowly made its way deeper and deeper. Of course as his focus was in the immense pain in his ass he forgot all about licking the juicy cunt his face was buried in, which then led to Josephine tugging more and more on the clamps on his nipples.

Once the dildo was firmly buried all the way up his tight anal passage, Billy managed to focus a bit better as the extreme pain subsided, giving way to a dull aching pain that was actually quite pleasurable. He started licking the cunt in front of him with a gusto he didn't even know he possessed. He was licking, sucking, nibbling and rubbing against Josephine's big clit as she herself was grinding herself all over his face. He was so into what he was doing that when Ally started fucking him it took him a while to understand where the pain was coming from.

Ally had added some more lube to his asshole as she let him rest and adjust to the cock. Now as she was slowly pulling it back out, she did the same to the long rubber shaft. She coated it well in the lube and once she had pulled back so that only the tip was still inside of him, she gave one hard push and buried it all back in. If he didn't have his face smothered by Josephine's belly and cunt the scream would have been deafening. Now however it was barely audible at all over the sounds of her moans of pleasure as Billy's tongue and face brought her closer and closer to orgasm.

Once she had gotten started, Ally was not stopping. She started out with a slow steady rhythm and as Billy's screams subsided as he adjusted to the invader in his ass, she picked up the pace; never letting him get too used to it. Before too long she was pumping the thick black cock in and out of him at a furious pace. Beads of sweat had started forming on her brow and she was getting a little winded. But she was determined to keep it up, at least until she had made herself cum while fucking him. So she turned on the vibrator in the dildo and a jolt of pleasure shot through her. She had to bite her lip to keep from screaming out loud as the vibrations against her clit were quickly launching her towards her goal. The closer she got to orgasm the harder she fucked Billy, and the harder he got fucked the harder he worked on Josephine's pussy.

And then, just as Josephine was nearing her orgasm, and Ally was pounding him like a maniac from behind, the weirdest thing happened. Billy could feel himself starting to cum. He recognized the twitching in his aching balls, and the throbbing of his cock. He desperately tried to stop it, but he was powerless against the betrayal from his body. He tried to beg, he tried to scream at them to stop, but his mouth was firmly held in place on Josephine's cunt and the only sounds that came out were muffled and inaudible moans. As he felt himself shooting his load onto the floor both of the women abusing him exploded. They both screamed out loud as their orgasms rushed over them. They both let go of him and he didn't have the strength to hold himself up. He collapsed with his face buried in the wonderful, wet pussy of his co-worker as Ally slowly pulled the big dildo out of him. Once it was out he just collapsed into a pile on the floor, shaking and quivering as he tried to lift his head up to be able to catch his breath, but he just didn't have the strength.

Slowly and carefully Josephine made her way back to the couch. It was now her turn to lean on Allison for support, and the petite girl was more than happy to oblige. She let Josephine lay her head on her lap and stroked her hair as she was catching her breath.

As Josephine left, Billy could finally breath unobstructed again and he gasped for air, panting furiously both from exhaustion and from having had his breathing obstructed earlier. Just as he settled back into a more or less normal breathing pattern his head was lifted up by the hair and he felt the large dildo pressing against his lips. Dutifully he opened his mouth, saying a quiet thank you to the higher powers that Mistress had forced him to have an enema earlier that morning. There was nothing foul on the black rubber cock that had been deep inside his ass and that was now invading his mouth; but it did has the distinct taste of ass on it. It wasn't pleasant by any means, but the shame and degradation of it all made him shiver with shamed excitement. He tried his best to take as much of it as he could but when Ally started pushing it down his throat he struggled with the gag reflex. He had never sucked on any kind of cock before, and the act itself was exciting enough but having this giant cock that just came out of his ass shoved so violently down his throat, he was instantly rigid again.

Once Ally was satisfied that he had cleaned the entire cock with his mouth she withdrew it, gave him a small kiss on the cheek and whispered in his ear. "I am so proud of you. You did really well."

He thought to himself that he hadn't really done anything and if it had been up to him he would have stopped her just as she entered him; but he only said "Thank you." and gave her an embarrassed smile.

"That's 'Thank you, Miss Ally' for you, slut!" Ally added with a wink and gave him a light slap across the face; not hard enough to hurt but just to make a point.

As she turned and walked away from him she turned to Rose with a giant smile on her face and gave her a long, wet, passionate kiss right on the lips. Billy saw it and felt a small tingle of jealousy at the sight. He quickly pushed it away though. It was a true delight watching these two women that he loved so much being so friendly and comfortable with each other. A small part of him was wondering if maybe there was a possibility for more than just a one night thing with Ally, but he didn't dare hope for such a thing, so he pushed that thought aside as well.

"Thank you so much for this opportunity." Ally said to Rose as they broke their kiss. "I do hope I will get more chances to play with your toy."

Rose just smiled at her and nodded. "I am sure we can arrange that. The toy didn't seem to mind too much either, seeing as he just came without anyone touching his cock."

Upon hearing this all women's eyes were suddenly on Billy again as he lay there catching his breath. He looked at the floor where he had been positioned previously and sure enough there was a rather sizable pool of cum right there. He blushed again, making sure to avoid eye contact with any of the women. He still couldn't believe he had cum that hard without being touched. That had never happened before, but it was a wonderful feeling.

As Ally took her seat on the couch once again, sitting next to Allison, she took the smaller woman's head and guided it towards her tits. It was quite obvious to Ally at least that Allison was more submissive than dominant, and she thought she would take a chance. Without being prompted Allison opened her mouth and greedily started sucking on the large tits and their very prominent nipples. Ally moaned lowly as she stroked Allison's hair and pressed her head against her tits. It would seem she was correct in her assumption and judging by the eagerness with which the tiny girl sucked on her tits, she guessed that it wouldn't be too difficult to persuade her to go further than that. But for now Ally was content on just relaxing there and having her sensitive nipples tended to by this little beauty.

Now Lisa stood up, still clad in her underwear, and made her way slowly towards Billy where he was still laying on the floor. He tried desperately not to look at her as she approached, but as she placed her stiletto heeled boots just in front of his face he couldn't help himself. He had always had a thing for shoes, and especially this kind of highheeled leather boots that reached all the way up to her knee.

Tracing it with his eyes, as he reached the top of her boot he caught a glimpse of her crotch. There was a quite prominent and large wet spot right on her cunt. There was no question about if the events of the evening were to her liking or not.

As she caught him looking a smile crept across her otherwise quite stoic face. "Like what you see, do you? Well, go on and give them a proper cleaning then."

Billy didn't have to ask what she meant. It became quite evident as she lifted one of her boots up to his face. He eagerly started licking the leather, making sure not to miss a spot. She laughed down at him as she watched him intently. The little moans he made as his tongue whirled across the top of her shoes made her even more horny. Parts of her just wanted to push him down on him back and ride him until she exploded in a massive orgasm. But she was more than satisfied to use him in any other way she could imagine to bring herself pleasure.

"I can't say I haven't fantasized about this for a while." she said to his as he was just finishing one of her boots and switching to start on the other. "I don't know how many times I've played with myself in my office, imagining you down there between my legs."

"Well, you won't have to imagine it any longer." Rose said with a big grin on her face. "I'm sure that the whore wouldn't mind serving you whenever you see fit. Would you?" She looked down at him expectantly.

"No Mistress." Billy managed to get out in between licks. "It would be my pleasure, Mistress."

Lisa laughed at him and gently pushed him off her boot using the heel of the other one. As he laid there flat on his back he positioned her boot directly over his face and put it down; not hard at all, just resting there over his mouth.

"I think this needs a bit of a cleaning too, slut. I might have stepped in something on the way here."

That last sentence sent shivers all up Billy's spine. He knew the probability of her actually having stepped in anything nasty was pretty low. But there was always the possibility. He started out slowly and tentatively, but soon regained his original enthusiasm. Laying there naked on the floor with the five women he thought of as closest in the world to him looking at him licking the bottom of one of their shoes. He wasn't sure if he was in heaven or in hell; or maybe they were both the same in this case.

She let him work on her soles for a few minutes before she removed her boot from his face and stepped over to the bag with all the toys. She rummaged around in it for a while before finding what she had been looking for. She pulled out a few lengths of rope, a riding crop and a large ballgag and turned back towards him, motioning for him to stand up.

He rose slowly, not fully trusting his legs to carry him. As he finally made it into the fully standing position he let his hands rest behind his back. Lisa walked over to him and kicked lightly at his feet to get him to spread them further apart. She didn't stop until he had them spread uncomfortable wide, almost not able to maintain his balance. She produced a length of the rope and started wrapping it around his rock hard cock, making it even harder and quite painful. She pulled the rope as tight as she could, tying it around the root of both his cock and balls. Then she proceeded to wrap it tightly around his balls, once again tying it off as tightly as she could pull it. At this point his cock was so hard and throbbing it was painful. He winced and moaned every time she pulled on the ropes, and when she pulled back his foreskin and scraped a nail across the head of his cock, he let out a deep groan and had to really struggle to stay on his feet.

Lisa got a contemplating look on her face, left him for a second and went back to the toy bag. She grabbed a rather sizable anal plug, coated it with lube and returned to him. He groaned loudly as she without mercy or hesitation pushed the plug into his already sore and aching asshole. Once it was in place she took the rope that was left over after tying up his cock and pulled it tightly down between his legs, making sure it got in between his ass cheeks, pushing the plug in. She then made a knot and wrapped it tightly around his waist before bringing it down the front, wrapping it under his cock and pulling up as hard as she could. Billy groaned and cried out in pain, but before he could complain or beg for mercy, she had already tied the rope off around the base of his cock.

She took a step back and admired her handywork. His cock was so hard that the veins on it were bulging and she could see the tip turning a slightly blue colour. She smiled at him and he cast his eyes to the floor before she walked up to him again and lifted up his face.

"Open your mouth wide like a good boy." her tone clearly condescending and belittling.

He complied and she inserted the ballgag in his mouth. The size of the rubber ball had his mouth stretched as wide open as it could possibly go. He could already tell it wouldn't take long before his jaw would be feeling like it was falling off. He could already feel it starting to ache. Once the ball was in place Lisa took the strap and pulled it as tight as she could around his head, causing the gag to dig into the corners of his mouth and pressing his tongue slightly backwards in his mouth. He groaned unhappily but all he got in return was a smirk and a wink.

Looking Billy up and down Lisa nodded her approval. His cock was clearly painfully hard, sticking straight out in front and throbbing visibly. Now it was time for the fun part.

"I really do hope you like pain as much as your Mistress says you do." she whispered into his ear as she let the riding crop trace over his rigid cock. "Otherwise, this experience isn't going to be nearly as much fun for you as it will for me."

With those words she took a step back from Billy, holding the crop in her right hand. She teased him for a bit, letting the tip of it wander over the head of his throbbing cock, making him moan loudly behind the gag. Then without warning she raised the crop and brought it down right on the shaft of his cock with considerable force. He screamed into the gag, and fell down on the floor, not able to maintain his footing.

"Would you two lovely ladies mind holding the slave up for me while I work him over?" She looked over at Josephine and Ally who gladly accepted and rushed to help Billy back to his feet, and holding him tightly making sure he stayed in that position.

"And you!" Lisa looked over at Allison who was now alone on the couch. "If you don't mind, I would love to have my cunt eaten while I beat this whore."

Allison got a wide smile on her face and hurried over to the older woman, quickly dropping to her knees and slowly pulling the panties down before burying her face in the wet goodness underneath.

"There.. Now that we're all engaged, how about we get this party started?" Lisa started, then paused for a second before turning to Rose. "Unless you'd like to come join the party? I have an available spot right there at the back."

Rose laughed softly and smiled at her. "I'm good thanks. Though I might eat your ass another time. For now I'm more than happy just watching all you lovely ladies have your way with my lovely slave."

Lisa just smiled and nodded at her before turning her attention once again to the man in front of her, standing there looking at her all pathetic, pleading to her with his eyes not to hurt him. Unfortunately for him, she knew exactly what he really wanted. She had spent hours upon hours talking to Rose about every secret fantasy he had told her about. So she felt confident that she could bring him the pleasure he didn't even know he wanted.

With a quick flick of her wrist, Lisa suddenly brought the crop down right on the head of Billy's cock, causing him to scream at the top of his lungs into the gag. His knees gave out under him, but Josephine and Ally were holding him upright. Another blow of the crop, this time on the shaft, then another and another. She kept the crop striking him all along his cock. After five or six blows his screams turned into sobs. After another ten or so strikes, the sobs turned to sniffling moans.

She let him rest for a while, turning her attention to the lovely young woman between her legs. She moaned as Allison now assaulted her clit with everything she had. She lapped, bit, sucked and nibbled on it until she was rewarded with the older woman's juices flowing down all over her face as she came in a more or less silent, dignified orgasm. It was obvious that the young girl was inexperienced in the field of eating pussy, but she had a natural talent that could easily be refined. As she lapped up all the flowing juices from the lovely pussy in her face, she wondered if she was expected to stop now, or if Lisa wanted her to continue. Her question was answered as Lisa stepped off her and with a nonchalant push just shoved her aside.

"That's all for now. If you wish to stay and participate, maybe one of the other ladies want their pussies or asses eaten."

And with that she completely ignored Allison, turning her attention back to Billy. Allison for her part, crawled on her hands and knees over to Josephine, looking up at her with big, pleading puppy dog eyes. She was rewarded with a smile and a nod as Josephine pointed behind her and arched her ass out towards her. That's all the encouragement Allison needed. She scurried behind the big woman and eagerly buried her face in between her big ass cheeks, letting her tongue play with her asshole.

Lisa waited until everyone was in position before she once again started landing the crop on every available inch of flesh on Billy's very exposed, very hard and throbbing cock. Once again she was rewarded with screams turning into sobs, turning into sniffles and moans. After about thirty or so strikes Billy was moaning and screaming in equal measure with every strike. Lisa could clearly see some precum oozing out of his cock, but she also knew that as tightly as his cock was bound, there was no possible way that he could ejaculate. He could possibly still cum, but the pleasure just wouldn't be there.

She told the two ladies holding Billy up to lean him backwards a bit and secure his legs. They did as she asked and as the next blow landed they were all glad Billy was fitted with a large, tight gag. The strike landed square on his left ball. As he howled in pain, struggling against the two women holding him trying to get loose. Before there was any chance of that happening though another strike landed on the other ball, then another and another. She kept the crop landing blow after blow on his exposed, bound nutsack until his scream turned into crying. After about another ten blows he was blubbering and sobbing uncontrollably, As Lisa gestured to the other women to let him down, they gently put him down on the floor. Lisa put the crop away and kneeled down next to him, tracing a nail over his still rock hard cock.

"It really is too bad you were a bad boy tonight." She dragged her nail across the tip och his cock, eliciting a low moan from him. "I really would have loved to ride this thick piece of meat tonight. But I suppose that will have to wait until I get you alone in my office."

She climbed over him until she squatted above his face, slowly lowering her cunt down on it. As he was gagged he couldn't really participate in this bit, but that would only add to his humiliation. She slowly started to grind her cunt on his face, making sure to coat it completely in her juices. She used the gag in his mouth as a grinding post, rubbing it against her already sensitive clit until she once again came in a very quiet and dignified orgasm. Once she was done she stood up, picked her panties up from the floor and went back to the sofa to sit down.