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Author's Note: Two switches fall in love and this is the first of hopefully many stories about their double-the-fun sex life
She knew what she was getting into, but he was such a good guy, did it really matter? She didn't think so. Just because he was a bit kinkier than she realized, didn't mean it would be a bad thing for them. It would definitely keep their sex life interesting for a very long time. Their relationship was new, but solid and she was excited to have another avenue to play. At first it was fairly harmless, a pair of cuffs here, a panty gag there. It was fun and new and exciting and harmless.
At least until he brought out his bag of tricks. She wasn't quite prepared for the floggers and whips, lengths of chain, leather cuffs, giant ball gag. There were things she had no idea what they were; a cuff to go around balls with a chain hanging from them!? There was an enema bag and small plugs and spreader bars and a mess of leather and chains that apparently was a full head harness. It was a lot to take in and a lot she didn't know about. She'd always considered herself adventurous and open minded in her mind and group of friends (she liked anal, how scandalous), but after seeing all the new toys in front of her, there was so much more that she had never experienced, had never considered and had only vaguely understood what went into them.
Slowly, they began to try them out, he was on the more submissive end of the spectrum and she was a bit more dominant, but neither wanted a full life of servitude as Mistress/Master and slave. They wanted a relationship, with a lot of spice and some vanilla to keep both parties happy. He might have been ok with more spice and less nice, but she wanted freedom for both of them and since she was so new to it, it was still pretty scary, especially at the extreme end of things.
As their relationship progressed, so did their experimentation with his toys. They started with the cuffs, and tied each other down for whippings and spankings. Initially he was just showing her how to do it, but as he spanked her ass and watched it turn from a lovely pink to a solid red, he realized he enjoyed being the one in control as well. He had her ass across his lap for easy access. It was sore and as he dragged his flogger across it, he could feel her quiver beneath him in pain and pleasure. He tied her to the bed and whipped her with the flogger until her nipples ached and she left a wet spot on the bed. He had her change positions so she was on her knees and her red ass in the air. He dragged his fingers lightly across her ass, leaving little white trails that faded away, then slipped a finger inside her soaking pussy. She squirmed in pleasure and the lingering pain from her sore bottom. She'd never experienced anything like this and even before he'd started fingering her, she had been so much wetter than she expected it would make her. She felt him slipping first one, then two, then three fingers inside her pussy and fucking her harder, and faster. Then he'd slow down again and wiggle his fingers inside her. When she was close to her orgasm he stopped.
Finally, he let her go and have a turn at dominating him. As much as she had enjoyed the torment of being captive while he spanked and whipped her, and had his way with her, she enjoyed dominating him too. It was fun to feel him squirm when she dragged the whip across his flesh and smacked his cock with it. She would tickle and tease him with the leather ends until she saw his cock twitch. For extra fun she blindfolded him too. She would walk around the bed and smack him with it when he least expected it. Between the sharp, painful lashes of the flogger, she would stroke his throbbing cock, or tease his nipples until they hardened under her touch. He ached from her assault, but didn't know where to expect her as she stalked around the bed, delivering both pleasure and pain. His cock twitched and betrayed his pleasure from the whole experience. He loved knowing that she was there, just out of reach, out of sight. He knew that her soft touches and loving caresses were highlighted and more amazing because of the pain of a pinched nipple or a tap to his ball sack or lashes with the whip. When he didn't think he could take anymore, she had him flip over and spanked his ass until it glowed as red as hers After they both had had their fun, they kissed and fucked each other until they were both spent.
It didn't take long for the fun to intensify after that. On one particularly good evening, a few months into their relationship, they had agreed that she would be the full dominant for the night. They had safety words at the ready and had agreed to go for 4 hours, until midnight when it would be midnight and time for bed, since they both worked early the next day. Before he got home from work, she prepared for the evening. She gathered all of the tools she would need for her few hours of fun with him. They'd agreed to a number of strict rules (no blood, no watersports, no burns or piercings. Basically, nothing permanently damaging to either of them), but otherwise everything else was fair game and encouraged on his part since she hadn't independently tried much on him. She even went out to buy a few new toys that she had secretly considered when they browsed the site of their favorite bondage vendor.
When he got home, she met him at the car and they went to dinner until it was time to head home to play. She lingered at the car and when he walked to the house, he found a note with the rules and trail from the door to the bedroom strewn with different toys. The rules stated that as he walked in, he had to choose if he was going to pick something or pass it up. If he passed it up, he couldn't change his mind and go back. First was a bottle of vanilla and a quick explanatory note, which meant it would just be a plain vanilla night of fun but no bondage sex. She knew he wouldn't take it, but wanted to offer it and let him know that she had given him an out at the beginning. If he left that one, he couldn't come back to it and had to decide whether to take it or leave it in hopes of something better. Next came a pair of cuffs and some whipped cream, body paint and other fun food type toys. Much more interesting but not exactly what he'd been promised or was expecting.
He quickly moved on, following the connecting chain around the corner. Finally, something a lot more interesting, a collar and a note saying that he could pick the collar for the night and they would have some fun puppy play, or he could move on to the next toy around another corner. He considered staying with this one as it was one of his favorites, but he couldn't resist knowing what was next. It was just a bit farther until the bedroom. He had to know what the grand prize was. A gag and blindfold came next in line and as much fun as the sensory dep night would be, he'd already set his mind on going to the end of the line. Finally, he came to the bedroom and piled on the bed was pretty much every other toy they owned. His mouth dropped a bit when he saw the brand new strap-on that she'd bought for this special occasion. They'd talked about pegging but hadn't really ever done it. He'd had a couple small plugs and used the enema but still hadn't dared to try fully penetrating his ass. Next to it was another new toy she'd found which would be perfect for their evening of Mistress and slave. She had discovered something called a humbler and since they both played the dominant at times, there was no better way to remind him of his submission to her than having his balls stretched behind him and forced on all fours to keep the pressure and pain manageable.
Now that he had chosen his fate, she came into the room and helped him get stripped and strapped into everything for the night. She decided to start with the humbler and a thick leather collar and leash. Just because he didn't choose the item on his way down the path, didn't mean she wasn't going to use it anyway, at least for a little bit. She added a bit gag as well, to ensure there was no complaining about his role for the evening. She paraded him around the house and showed him off to their cat who was thoroughly confused. She took him by the windows and although they had excellent privacy, it was just another reminder that she was in control. After establishing this important fact, she sat in front of the tv for a little while and used him as a footrest while they watched one of their favorite shows together. During the commercials, she'd talk to him as if nothing was wrong. He loved this in particular whenever he was tied up. It turned him on whenever she pretended everything was fine, that he wasn't on his knees at her command. He liked having her treat everything normally while knowing that anyone walking by would probably call the police in concern. It made him so horny. His cock bulged and ached but any time he would reach for it, the riding crop left a bright red mark on his ass. He smiled through the bit.
After their show was over, she asked her slave if he wanted the bit gag gone. He nodded and she agreed to take it off. After she did, she replaced it with a ring gag. She smiled at the switch and told him that he needed to lick her pussy for so generously removing the bit. As she was still on the couch, he needed to kneel to get to her pussy and it pulled his throbbing cock and balls as he strained against the humbler. He lapped at her pussy juices and toyed with her clit and pussy lips. He knew exactly what she liked and slid his tongue slowly and then more quickly in and out of her pussy. He pushed his face against her mound, adding pressure to her clit, feeling her and her clit pulse beneath him. He played with her until she was ready to cum. He decided to deny her the orgasm she was so close to and stopped just short. It earned him a sharp slap and she pushed his face into her pussy again. She was not amused and promised to prove it once he'd had her orgasm at least twice and licked up all of her juices.
By the time he finished, she was very satisfied but still had a long time with him and needed to punish him properly. She dragged him to the bedroom and had him stand, as tall as he could while his balls were stretched and locked behind him, against the bed to receive his paddling for misbehaving. She decide to paddle him 30 times as it'd been about 30 minutes into their arrangement when he denied her. His ass was a very bright red and terribly tender by the end. She gave his red ass a quick kiss before removing the humbler and securing him to the bed spread eagle. She added a blindfold and left him alone for a little bit to prepare an enema for him. When she came back, she teased his cock, mounting him and rubbing her wet pussy along his shaft, and sliding just the tip inside before taking it back out. She slid up until she was positioned above his face and had him lick her pussy. She lowered herself onto his face and he licked and nibbled on her clit and tongue fucked her until she came again. Before she untied him, she gave his balls a sharp flick. His hardon immediately softened and she slipped his cock into a newly acquired chastity device. He was then sent on his way to the bathroom for his enema. She let him take care of business and waited patiently while she tried to decide what she had time for. She was already at about halftime by the time his enema finished.
When he came back all clean and fresh, she decided she would leave on the chastity and slip in one of the vibrating plugs into his tight ass. She tied him to the bed in doggy style, hands spread eagle and his ass in the air with the humbler around his balls and the vibrating plug in his ass. After everything was secure, she put on their sensory deprivation hood onto him and secured it. She left him like that for what seemed like forever. His cock throbbed and he was horny as hell. He felt her leave the bed, but otherwise didn't hear or feel or see anything. He didn't know what was going on, how long it had been, where she was or what she was doing. He enjoyed the feeling and wondered what she had planned next. Occasionally he thought he felt a feather light touch or could smell her through the small breathing holes. But his world was dark and quiet. He didn't feel the bed move, or any other hints of her being there with him. He couldn't stop thinking of her, there was so much he wanted to do to her. And she still hadn't let him fuck her!
She finally returned to him but before taking of the hood, she fucked him gently with the plug. It definitely wasn't comfortable but it was smaller than the strap-on she'd purchased and she wanted his ass to be ready to take it. She was nervous about the strap-on as she'd never used one and it was single sided with just a small slot for a vibrator on her side. The whole thing vibrated too, just in case she wanted to tease him more. She decided to leave him in the cage for this, but took off the hood, just in case there were issues, and left him without a gag. She didn't tell him this, but she wanted to try milking him. Although not entirely sure how it worked, it sounded like fun and would deny him an orgasm for most of the rest of the night.
She took out the plug and unlocked the humbler, then added more lube to her new cock and his asshole and slipped the tip inside him. He grunted in pain as the large cock penetrated him, but he didn't say anything. Taking that as a good sign, she slid her cock all the way inside him and back out slowly. It took her a while to figure out the rhythm and it was much harder than she imagined. Once she figured it out, she turned on her little vibrator and hammered away at his ass as fast and as hard as she could. She gripped his hips and he grunted in pleasure and a bit of pain as she fucked his ass. She spanked his pink ass and asked him if he liked his Mistress fucking him. He told her what she wanted to hear, what the truth was, that his ass was hers for the taking and he loved having her pounding away inside him. He had never felt anything like it, and even though it was new and uncomfortable, it made his cock hard (as it could be) and sent tingles up his spine. She slipped her new cock in and out of his tight asshole until she finally collapsed with a shuddering orgasm. It was so much better than she had anticipated!
She asked if he was alright, and after assuring her he was fine, but horny, she proceeded to go again slowly and carefully, trying to find just the right spot to try this milking thing. She played with his ass a bit, pulling all the way out to a sweet popping sound and then thrusting back inside him. She did this several times and loved the power and the control and the soft moans he made as she fucked him so slowly. She slipped her cock in and out of him at a steady pace and finally she found just the right place for her cock to milk him of his cum. She continued like this for a few more minutes and after a bit, grunting and moaning throughout, he realized that he'd cum. He looked between his legs in shock that it had seeped out of him without being able to control it and without any pleasure. She was thrilled and he was disappointed. He realized that his likelihood of orgasm was significantly diminished for the rest of the evening.
With another accomplishment for the night under her strap-on belt, she decided to give his ass a break. She only had about an hour left before they had to go to bed. She let him up to get himself clean and decided what she would do for the rest of the evening.
When he came back, she had him on his knees with his head between her legs. As good as fucking him had felt, his tongue always provided the most incredible orgasms. When she finished and was dripping wet, she released him from the cage and took him in her mouth. He groaned in pleasure, but as soon as he was hard, she stood back up and told him to fuck her. Even though he had spilled his seed, he was hard as a rock without any of the normal recovery time. He pounded away at her and despite it feeling amazing, he was nowhere near an orgasm by the time she had her second one.
She asked what he thought of it all and upon hearing that he wasn't able to orgasm still, went at it another round, this time with her on top. By the time she was getting close, he was too. She had been asking if he was close yet and he told her he was. She asked him to tell her when he was about to cum and when he told her, she immediately moved away from his cock and as he groaned in frustration, she had him finish her orgasm with his tongue. He was so incredibly frustrated that by the time he finally was close to a real orgasm of his own, she denied him.
After he had cooled off a bit, she laid next to him and toyed with his nipples, finally clamping down on them with their always too tight nipple clamps. He moaned in pleasure and pain as she mounted him again and pulled lightly on the chain between his nipples. She rode him to another climax and when she collapsed on top of him, she released his nipples and licked them and played with them as the blood returned. She rolled off of him and laid next to him while toying with his cock and his slightly blue tinted balls and his bruised nipples. He laid there frustrated and horny and hard as they watched the clock hit midnight.
When he looked at her at 12:01, she was fast asleep.