A Questioning Man – BDSM – Sex Story


It had taken some planning, but Lady Bex finally had both subs at the same time. Usually their sessions were separate, but Lady Bex had wanted to try combining it. She had plans for both of them.

Zach was bisexual, which was what had given Lady Bex the idea to involve both of them. He was 22 years old with dark hair and eyes. He was very handsome, and his submission all the time made her wet.

Seth was older. He was 39, and a questioning straight man. Lady Bex had spoken to him about trying a session with another man, going into detail about the things she wanted. She knew he was a little intimidated, but he would do anything for her approval.

Seth, the good pay pig he was, paid for the private dungeon room where they would meet. Lady Bex and Zach were already there. She had things to do to Zach before Seth arrived. He was on his hands and knees, his legs tied with rope in a “frog tie” style. His balls were held in place quite literally between his legs by a wooden humbler. Lady Bex had unlocked his desperate cock when the session began, and she could tell by his whimpering that he desperately wanted it to be touched.

She grinned, “Poor thing. Who knew it would only take a week of being locked up to make you so desperate. That’s pathetic.”

Her crop landed squarely on his balls, and Zach yelped. His ass was already glowing a bright red from the flogger she had used previously, which she intentionally let hit his balls too. He could scream and yelp all he wanted, Lady Bex knew what her bitch liked.

She squatted down behind him and teased the head of his penis with her thumb and forefinger. Her short, red nails looked glossy in the dim lighting. Zach moaned and his hips wiggled as he tried to get her to touch more, but she pulled her fingers away. She laughed, “Do you want me to touch your little dick, bitch? Well, there’s conditions to that.”

“Anything,” he breathed, “Anything, Lady Bex. I’ll do anything, It hurts. I need to touch it, please!”

His hands were free, and his fists were gripping the carpet under him. She smiled, “That’s my good boy.”

She had brought her own toys, not wanting to use the dungeon’s. She was sure they were fine, but she preferred to use her own. She pulled a padlock and lube from her bag and set them on the floor behind him.

“Hands behind your back,” she ordered. Zach obeyed. She snapped the padlock around the rings of his cuffs, locking his hands behind his back. His head was forcibly lowered to the floor, where he belonged.

She lubed one of her forefingers and teased the bitch’s asshole with it, before gently sliding it in to the first knuckle. She moved it back and forth, trying to loosen him up. His ass was gonna be put to good use later, and she didn’t want him to tear. Once he could take two fingers, she began to fuck him a little harder with them. He moaned and his cock twitched.

“Please will you touch it Lady Bex?” He pleaded.

“Will I touch what, bitch?” Lady Bex replied.

His voice was desperate, “Please would you touch my tiny cock?”

“Not yet,” she answered with a quiet chuckle. She thoroughly enjoyed his desperation. She curved her fingers to press against his prostate and at the same time reached between his legs to give his cock a firm smack.

Zach yelped, “Thank you Lady Bex!”

She rewarded him by giving him three full stokes. Any attention to his cock was

needed. She pulled her fingers out of him and replaced them with a lubed plug. It was bigger than what he was used to, but his ass needed to be stretched. Lady Bex was careful when she slid it in.

She removed the humbler and rubbed the place it had been, both to ease some of the bad pain and to check for any potential damage. He seemed to be fine, so she moved on to untie his legs and unlock his cuffs.

“Stretch while I get something else,” she ordered.

“Yes, Lady Bex,” he replied, slowly straightening one leg. She planned to put his legs in the same position later, but for now she was gonna add some more cuffs. His wrists and ankles already had leather cuffs around them, but she was gonna strap a pair on his thighs. It didn’t take long at all.

“Now, Seth should be here any minute if he knows what’s good for him,” she started, “Come, over here.”

She waved with her hand for him to follow her.She picked the crop up as she moved. She sat on a very comfortable leather-padded chair. The back was very decorated, and the whole thing nearly looked like a throne. She sat, and Zack, being the anticipatory bitch he was, got on his hands and knees in front of the chair.

Lady Bex smiled, “That’s a good footstool.”

She rewarded him with a lash to his balls with her crop. He yelped, clearly not expecting the lash. She lifted one leg from his back and rotated her ankle. Her strappy heels amplified her beauty, the high-thigh stockings accented her legs. Her garter belt fit snuggly around her waist and the comfortable bralette decorated her breasts with lace. Her feet were a little sore, she’d make one of them massage them after their session. She looked at her phone, it was almost time for Seth to arrive. She frowned, thinking he would have been a little early.

She relaxed, enjoying her break from standing. There was a very quiet sound of a key jiggling in a lock, and the door opened. Lady Bex looked up from her footstool and met the gaze of her other submissive.

“Hello, Seth,” she greeted. It was the first time she’d seen him that day.

“Hello, Lady Bex,” he replied.

“Strip,” she ordered. She wasn’t in the mood for formalities. If he had a issue with something, he would tell her.

Seth obeyed, quickly removing his clothes and setting them on a trunk beside Zach’s. He knelt, waiting for a command.

Lady Bex stood and looked down at Zach, “Stay until you’re told otherwise.”

“Yes, Lady Bex,” he breathed, and she could tell that he was in sub-space.

She turned to Seth, “Stand.”

She crossed the room to the large bed where her bag sat. She pulled a set of cuffs and a collar identical to the set Zach wore, and locked them around the wrists, ankles, and neck of her slave. She pulled a pair of condoms from her bag.

She removed her necklace with the key to Seth’s chastity cage and unlocked it. The cage and key were both placed on the bed. His cock was erect immediately, he’d been locked for much longer than Zach.

“Footstool, come here,” she commanded, reaching into her bag for something else. The bitch crawled to her and knelt by her feet. She enjoyed his devout submission to her.

“Stand up,” she said. She opened the wrappers of two condoms and put one on each.

“Zach, kneel.” Lady Bex ordered. Seth looked at her, unsure of what to do. She turned to him, “You, stand there.”

“Zach, be a good cock sucker. Don’t let him cum,” she ordered.

He nodded. She wasn’t upset at his lack of verbal response. Quite the opposite actually. His sub-space was very strong and she was glad he was in it.

He was very good with his mouth. Lady Bex often used him as a pleasure slave for that reason. She loved making him suck a cock for her too.

Seth couldn’t help but moan, and Lady Bex knew the pleasure he must have been feeling. He ran a hand through Zach’s hair, then gripped it tight and held them there by it.

“May I face-fuck hm?” Seth asked. She nodded. Instantly, he bucked his hips. Zach’s gag reflex had disappeared long before. And he became a very still and relax piece of fuck meat for the other slave. Seth, still knowing his place, retracted from Zach’s mouth before he could cum.

She repositioned Zach so that his feet nearly touched his ass. The cuffs on his thighs and ankles were locked together, his hands were behind his back, his plug had been removed, a pair of clover clamps were added to his nipples, a phallic gag in his mouth, and a blindfold.

Seth was on his knees behind him, lining his cock up with Zach’s asshole. When he was fully sheathed, Lady Bex spoke, “Now, Seth, you are not going to cum until you have permission. To earn it, you’re going to make him cum.”

“Yes, Lady Bex,” Seth replied. She sat on the bed and watched, slipping a hand into her panties.

Seth started to slowly pump in and out of Zach, who moaned softly into the soft carpet. Seth wasn’t big by any means, his dick was quite pathetic, but it seemed to feel good to Zach. Zach had never cum from anal only, and she thought how Seth would feel, to actually get another man off. He was questioning, but by the end of the night he would have a much better idea of his own sexuality.

“Harder,” Lady Bex commanded, “He’s warmed up now.”

Seth obeyed, and the sound of skin slapping skin filled the room while Lady Bex teased her clit.

“Now, stroke his cock,” she ordered. Seth looked at her, but obeyed. He stroked it slowly at first, it was probably his first time touching a cock other than his own. Soon he sped up and Zach moaned through his gag.

“You may cum, Zach,” Lady Bex said. As if it was commanded, Zach came, his cum filling the condom. Seth slowed his pounding to a gentle thrusting.

“You can pull out. It’s time to lock you back up.”

“I don’t get to cum?” Seth asked, almost in protest.

She raised a brow at his tone and replied, “No.”

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