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.