Will and his girlfriend Ann had made plans to head up to Will’s cabin for a weekend of fun times. They had planned to leave on Friday after Ann worked a half-day. Yet little did Ann know that Will and her best friend Cassie had been talking about surprising her and Tony, Cassie’s boyfriend, that weekend with a little fun role play of master and slave. They thought it would be perfect as both Ann and Tony were a bit on the submissive side and loved to be dominated.

Before leaving work, Friday Ann got a message from Will saying that she should plan to be his little whore for the weekend. This sent a thrill through her as she loved to role play with Will. Friday went as planned and Will and Ann made it up to the cabin Friday night. They had planned to go to a little local craft show on Saturday but before leaving Will wanted to make sure his little whore was properly prepared.

Ann was already dressed and ready to leave when Will called her back into the bedroom. He was standing there holding a small slave collar, that looked more like a fancy necklace, in one hand and a vibrating anal toy in the other. He placed the collar around her neck and said, “If she was good, she could stay off-leash.” He reached in and pulled the end of a black leather leash from his pocket, showing it to her. He then instructed her to unbutton her jeans and slide them down along with her thong before having her bend over resting her hands on the bed.

Will taking the anal toy, coated it in lube. Then placed it at Ann’s tight little opening. He paused just briefly before pushing it in, causing Ann to yelp in surprise that quickly turned into a moan as he turned on the toy to make sure it worked. He could see by the moisture already forming on her pussy that it indeed worked. He couldn’t help but run his fingers through her pouty lips before telling her to straighten herself up like a good little whore. Then they left for the craft show with the anal toy snug in Ann’s ass.

Unbeknown to Ann there were more surprises waiting. Cassie had told Tony they were going up to Will’s cabin for the weekend for their own little fun getaway. She had told him that Will and Ann had decided to take a little trip and they could use the cabin if they wanted.

As they got ready to go, Saturday Cassie, had a little surprise for Tony. She had gotten him a vibrating anal toy to play with. There were times when she would use a strap on to fuck his ass until he was exploding in orgasm. Before he dressed, she had him lay on the bed where she lubed his anus up slipped the toy in. Just like Will had done, she tested it and Tony’s cock almost jumped to full attention. She playfully slapped it and said not yet boy. Later if your good for me.

Will and Ann were walking around the craft show when Ann spotted Cassie and Tony walking towards them. She leaned in closer to Will and said, “Master, I guess me pleasing you all weekend is off.”

Will turned to look at Ann and said, “You will do as I tell you when I tell you!” Slipping his hand into his pocket, he pushed the button activating the anal toy.

Ann had gotten accustomed to it filling her but when he triggered it, the jolt hit her and she stopped dead still and tensed up. He could see her eyes gloss over as each jolt passed from the vibrating toy, through her anus, up her spine, connected with her brain. He let it settle in he was in control, knowing she loved it when he was. He final clicked it off as Cassie and Tony drew closer.

The two couples greeted each other and walked around the craft show for a while looking at the different things for sale. After a while, they all head to the local tavern for dinner and some drinks. When they got there, Cassie slipped on some mud getting it on her pants. She brushed at but left a large spot on them.

After getting inside they all had a nice dinner and a few beers. Will and Cassie only had a couple of beers a piece because they were driving to the cabin. Ann and Tony each had a few more that was loosening them up nicely.

As they got ready to leave, Tony said something about driving but before he could fully articulate it, Cassie triggered Tony’s anal toy and leaned closer to him say, “I’m in charge and don’t you forget it!”

Will could tell Cassie had triggered Tony’s anal toy as he got that same glassy stare Ann had gotten and quivered just enough Will caught the motion. He just smiled and looked at Cassie who smiled in return.

It was about eight when they all decided to head back to the cabin. On the way back Will ran his hand along Ann’s inner thigh, rubbing back forth, occasionally letting the side of his fingers rub against the crotch of her jeans. He looked over at her and just winked, letting her know she was in for a fun night. His touch was making her wet with anticipation of what he was going to do to her later. Little did she know what was on the menu that night.

As they entered the cabin, Cassie announced she needed to get out of these muddy pants and take a shower. Looking over at Tony she said, “You come with me, you need a shower as well. Get the bags.” She pointed at the two little suitcases they had brought in. Tony picked them up and headed towards the spare room with Cassie following with a wicked grin.

As she passed Will, she leaned close and said, “I’ll knock when we are ready for you to join us.”

As Cassie and Tony disappeared behind their door Will took Ann’s hand and said, “We need to shower also,” leading her into their bedroom.

As they entered Will stopped in the middle of the room and said, “Strip!”

Ann didn’t hesitate. She quickly pulled her t-shirt off, tossing it aside. She undid the snap on her jeans and slid them down until they were piled at her feet. She then slid the bit of lace that was her bra off, leaving her firm breasts exposed to Will. She finished her stripping by sliding her thong down her thighs until dropped to the floor on top of her jeans. Will glanced down and saw how wet her thong was before he turned his eyes on her. He couldn’t help but reflect to himself what a lucky man he was to have her in his life.

Now she was naked except her collar and the anal toy, Will told her to undress him. She did until he was standing there in his briefs. She was on her knees now and grasped the waistband, tugging them down until they were on the floor. She was now facing his semi-hard cock. She looked up at Will with those eyes, asking if she could suck it.

Will looked down at her and said, “You may suck it!”

She immediately took it between her lips, making love to his cock in the way only she could. Will felt his approaching orgasm and ordered her to stop saying, “If you are a good slave, you will get your cream.” He offered her his hand to help her stand, then led her to the bathroom.

When they came out of the bathroom Will had Ann stand next to the bed. He went to his bag and pulled out the other toy he had bought for the weekend. It was a strapless dildo. One end would be inserted into Ann and the other hung out as a normal dildo would.  

Will taking the bottle lube applied a generous amount to the end of the dildo to be inserted into Ann. He knew she was wet with excitement but knew the dildo would be deep and he wanted her comfortable. Having her spread her legs, he then slipped her end of it between her lips, gently wiggling it and pushing until it was snug in her pussy.

After he had finished, he helped her lay on the bed. As she laid there, he activated both the anal toy and the new dildo. He thanked the inventors of Bluetooth technology since he was able to control both with one remote. He varied the speed causing her to moan and twitch as she was being stimulated from both of her holes. Her eyes where clamped shut as the sensations wracked her body.

Will was standing beside the bed watching Ann work through each sensation as he sped up the speed on one toy and slowed the other or turned both up at once. He had gotten hard watching her and was slowly stroking his cock thinking about what was still to come.

It was during this time he heard the soft knock on the door. Turning both toys off he told Ann to stay laying on the bed until he came back for her. She just obediently nodded still coming down from the sensation Will had been flooding her with.

Will went out to the living room to see Cassie but she had already gone back into her room. The door was still open and he heard her tell Tony, “You’re going to get a fantasy fulfilled if you do as I say.” Will thought to himself, what fantasy and what did she plan they hadn’t discussed?

Will went back into his and Ann’s room. She was still on the bed with her eyes closed. He couldn’t help but look her over. So sexy laying there with the dildo jutting up from her. He also noticed how wet the bed was under her. He hadn’t let her have an orgasm but she had definitely gotten very wet. He continued on over to his bag and pulled out the last of his special supplies for the weekend. He laid a pair of leather restraints on the bed, a leather strap with several snap clips attached and a silk blindfold.

He went to Ann and slipped his hand into hers and said, “I’m going to help you up but keep your eyes closed and mouth shut whore.”

He helped her up until she was standing next to the bed. Once she was standing, the first thing he did was slip the blindfold over eyes. He then picked up the restraints and secured her wrist in front of her. Then finally taking the leather strap, he clipped one end to the chain between her wrists. Then making sure she could only raise her head so far clipped it to the collar that she had been wearing all day. The rest of the strap he just left hanging for later use.

With her standing there ready for the next part he took the remote and flipped both vibrators on to full sped. The sudden jolt running through Ann’s body just about caused her to collapse but Will grabbed the strap holding her up and said, “Come with me my whore, your services are needed.”

He led her out of their room by the strap. She was having a hard time walking because he still had both vibrators going full speed. Will realizing her difficulty walking shut them off but not out of kindness, just practicality.

As they approached the door to Cassie and Tony’s room, he heard Cassie moaning and telling Tony, “He had better not make her cum.”

As they went through the door, the sight that greeted Will was one of Tony lying on the bed nude with a foam wedge under his ass and back lifting him up off the bed. His legs were spread wide and secured to the bed by a soft rope so he couldn’t close them. His hands were resting on his stomach, bound together by a leather restraint like Ann’s but Cassie had taken a piece of rope and looped it around his body and tied it off so he couldn’t lift his hands up but a few inches.

What Will didn’t see right away was the blindfold Tony was wearing because Cassie was riding his face like a cowgirl on a bucking horse. He also noticed how hard Tony was. Cassie had put a cock ring on him and it was helping to hold him rigid. Moving closer to the foot of the bed, he could also see the anal toy firmly stuffed in Tony’s ass.

Standing there watching Will was getting hard and horny. He tugged on Ann’s leather strap until she was standing in front of him. With a firm push, he had her go to her knees. She knew what he wanted and opened her mouth so Will could shove his cock in, stuffing her full quickly.

Cassie looked up at Will and smiled holding up the remote for the anal toy. With a devilish smile, she pushed the button that sent it to its highest speed. Tony’s reaction was as immediate as Ann’s had been. His ass tried to lift off the wedge as he let out a guttural moan.

Will held up his remote and smiled and pushed the high-speed button as well for Ann’s toys.

Ann had clearly heard Cassie moaning and her warning to Tony before being pushed to her knees and fed Will’s cock. He was contently letting her work it at her own pace. She had Will deep between her lips when she heard Tony’s moan and not a heartbeat later, she was jolted by both of her toys going to full speed. She tried to keep sucking Will’s cock but just couldn’t. The sensations were driving her wild and she let him fall from her mouth as she let her own deep and protracted moans escape from her.

While looking at each other smiling, as if by an unspoken agreement they both clicked off the toys. Cassie said, “He is ready if she is.” Of course, both Tony and Ann had heard this through their pleasure racked bodies. Neither knew what was coming but knew it would be something wild if things continued as they had so far.

Will, pulled up on the strap causing Ann to stand. He guided her until she was standing at the foot of the bed right in front of Tony. He took the bottle lube that Cassie had left on the bed for him and squeezed a generous amount into his hand. While standing behind Ann, he reached around ran his lube coated hand up and down her cock making sure it was well lubed for its use.

Will said, “I’m going to help you kneel on the bed in front of you. You will scoot forward until you fill flesh and stop. Then I will help you with inserting your cock.” Ann answered she understood and pictured she probably would be fucking Cassie with her cock but she was in for a surprise.

Cassie had scooted off Tony’s face until she was straddling his chest. She leaned over between his legs, flattening his throbbing cock under her breasts, to remove the anal toy from him. While pulling it out she said, “You won’t need this anymore, we have something you’ll enjoy better.” She then took the bottle lube that Will had dropped back on the bed and squirt a large glob of it directly into Tony’s still expanded anus. She slid a finger into it as well to spread the lube.

Will got her kneeling on the bed and had her scooting forward. As she scooted forward, she stopped as told when she felt the flesh of somebody’s thighs. Out of instinct, she had her hands out as far as the strap would allow and she felt Tony’s balls touch her fingertips. Now she was trying to figure out was happening and it was then Will grasped her cock and placed it against Tony’s anus.

Will said, “Move your hips forward and push.” As she did, he guided her cock into Tony’s well-lubed ass. He helped her get it all the way in until she was resting her pelvis flush against his ass. The cock in as deep as it could go.

Tony grunted and moaned the whole time the cock was slipping up his ass. He tried to wiggle but Cassie had bound him good and tight. Cassie had also stayed laying across him with her face just inches from the whole scene. She watched the cock disappear into Tony the whole way until there was no way to go further, then she scooted back until her pussy was over Tony’s face again.

Will took the leather strap and hooked it into Tony’s restraint leaving just a little room for movement for Ann but not enough for her to pull too far away from Tony. He then leaned into her and whispered into her ear, “Fuck him good, he always wanted you too.” With that, Will turned on both toys to the lowest setting and let them buzz away in her ass, pussy and Tony’s ass.

Ann didn’t need more encouragement, she started moving her hips back forth, pulling her cock out as far as her restraints would allow before plunging back into Tony’s ass. Each time she pulled back she could feel the grip his ass had on the cock, it would pull against her end as well and as she drove back into him, it would push back into her. She was literally fucking them both each time.

Will and Cassie watched Ann fuck Tony as he writhed under Cassie. Cassie didn’t think his cock could get any harder but it was swollen and straining against the cock ring now more than she had ever seen it.

Cassie looked back at Tony and said, “You like Ann fucking your ass, don’t you?”

For Tony’s part, he couldn’t begin to answer through the moans escaping his lips and Cassie’s pussy smashed against them.

Will had been stroking his cock while watching the whole scene until Cassie looked at him and tilted her head, looking back behind her. Will got the message and as he passed behind Ann, running his hand over her ass and down to her pussy before saying, “Don’t stop until I tell you.”

Will slipped onto the bed and moved up behind Cassie, who had scooted back until her pussy was firmly over Tony’s face. Will could see Tony running his tongue along her slit. He thought how nice that must feel and slid his cock into her pussy just as Tony’s tongue was covering it forcing Tony to lick the length of his cock as he entered her.

After slipping into Cassie he reached over and slid Ann’s blindfold off, tossing it aside. Wanting her to watch him fuck her best friend as she fucked her friend’s boyfriend’s ass. Knowing this would excite both of them even more.

Will started fucking her at a nice slow pace. Each time he pulled out he felt Tony’s tongue run down his length and across his balls as he went deep into Cassie. By this time Cassie was doing her own writhing and moaning but they were all surprised at the loud cry from Ann announcing she was cumming.

She had pressed up against Tony and was shaking hard enough everybody could feel her. Slowly she calmed down and was looking Will right in the face with a look questioning how much more. Will understood that look and knew she was about done for. Reluctantly he pulled his cock from Cassie’s soft snug pussy and the attention of Tony’s tongue even though he had yet cum.

Cassie let a moan of disappointment as he pulled out but she could see Ann’s face as well and knew her friend was just about done for. She knelt up still riding Tony’s mouth and unhooked the strap from Tony’s restraint as Will came around to help her to pull out of Tony and get off the bed. He had already clicked the remote for the toys turning them off.

Will helped Ann off the bed and then over to a love seat that was in the room. He sat down and she collapsed against him not moving, just panting and quivering lightly. As he held her, he watched Cassie dismount Tony’s face and go over to her bag where she picked up a regular strap on harness and slipped it on.

She walked back to the bottom of the bed and picked up the lube applying a generous amount to the cock in the harness before moving up to Tony’s already stretched asshole. As she entered him, he moaned loudly but she kept applying pressure until she was all the way in.

Leaning forward she pushed off his blindfold saying, “I want you to see who is fucking you now.” With that, she started slipping in and out in long strokes. As she did that, she had taken hold of his cock and slipped the cock ring off, freeing him. She pounded his ass and stroked his cock hard and fast. Still being restrained all he could do was endure.

Will sat back on the love seat holding Ann gently watching Cassie and Tony. Ann spoke softly and said, “I’d bet you’d like to have a cock in somebody’s ass about now?”

He looked down at her and thought she was right but wasn’t going to expect anything else from her tonight. She was staring right back at him, reading his thoughts. She finally said, “Take me, you know you want it and so do I.”

Will lifted her up off of him until she was standing in front of him. She was still restrained by her wrists and the strap to her neck. The dildo was still in her pussy and although it had started drying, she was a wet mess and then there was still the anal toy. He reached out and gently slid the dildo out of her pussy, dropping it to the floor. She moaned as it came away leaving her empty now. He then undid the leather strap from her collar and popped the latches on the restraints dropping them to the floor. He then reached for the anal toy, slipping his fingers around the top of it, he pulled it out dropping it to the floor as well.

Once she was free of all the toys she moved over to the bed above Tony and grabbed a couple of pillows and laid over them, raising her gaping asshole in the air. Will was quickly behind her spreading lube into her and on his cock. He slipped into her, pushing past her inner and outer rings with only a small grunt escaping from Ann. He knew he wasn’t going to last long but wanted to give her all he could. He started with small movements at first but was soon pounding her hard and fast.

Each time he drove into her the bed would move under them but the bed was in a continual motion with Cassie still riding Tony’s ass and he riding Ann’s. Somebody would’ve thought there was an earthquake watching it shake.

Will was almost there; he could feel his cock tightening and was doing his best to give Ann the fuck of her life. Just as he was starting to cum, Tony let out a guttural cry. Looking over at them Will saw Tony’s cock erupt, shooting cum all the way above his head. He kept pumping stream after stream until he had a trail running down his body to a small puddle collecting below his dripping cock.

That was Will’s trigger, with a loud grunt he pushed against Ann hard and empty his balls deep in her ass. He could feel his built-up load create a pool of cum in her bowels and started pushing out around his cock as he held against her tight. Then he felt Ann shaking against him and knew she had climaxed as well.

Will finally slipped from Ann’s ass and pulled her to him cuddling as they lay across the bed. Cassie had released Tony as well and they were cuddled up as well on their end of the bed. Nobody said anything, they were all too exhausted and just needed to rest before getting cleaned up.