The Hathaway

Punished

We quickly changed into sweat pants and tee shirts, and drove to the boarding house. The first floor was empty, and we were able to make our way to the kitchen and down the cellar steps without meeting anyone. We waited silently in the main room, and after a moment we heard a faint moan and the sound of a door closing. Miss McFiercesen entered through the door that led to the back portion of the cellar, with all the arched storage rooms in it, but this was not the Miss M. we were familiar with. She wore a red leather corset and matching thigh high boots with six inch heels. We could just make out a black studded jock strap under her micro-miniskirt, and atop her fuchsia wig, a black leather hat managed to remain in place through some unseen attachments. She held a patent leather riding crop and her hands were partially covered with fishnet finger-less gloves that reached almost up to her elbows.

She lifted a finger to her lips to signal she still wanted silence as she approached us and whispered. “Thank you for coming on such short notice.”

We were both so taken aback by her appearance that it took me a moment to respond. “Umm...Yeah, no problem. What’s this all about?”

“I need your help with Helmut,” she whispered, gesturing to the back of the cellar. “I’m punishing him for disappearing like he did, and I need a witness. I only need one of you, but I didn’t want to ask either of you to do something behind the other’s back. You can both come in if you want, just don’t make a sound while you’re there”

“A witness?” Ben asked. “and why are we whispering?”

“It’s part of the humiliation,” she smiled. “He needs to know that someone saw him being punished but he’s not allowed to know who. All he knows is that it’s someone he knows from town, so when he’s out in the real world, he can never be sure if the person he’s talking to has seen him...well, bound and mastered.”

Ben chuckled, “Oh my god, I thought he was walking funny today.”

“I bet he was,” she smirked. “His balls took quite a beating last night. So, who wants to watch him take his punishment?’

We looked at each other and grinned. “I’m in.” I said with a chuckle.

“Hell yeah,” Ben added, “Wouldn’t miss this for anything.”

She once again shushed us as she opened the door and lead us down the hallway to the last room on the right. She opened it and gestured for us to enter, then, following us, she closed it with a bang. Her demeanor immediately changed, as she strode purposefully to him and slapped his face hard. “He’s here,” she said flatly. “Now you’re really in for it.”

Helmut was lying on his back in a leather sling, which hung in the middle of the room. His hands and feet were spread wide open and bound to the chains that hung from the ceiling to support it. His ass and belly were bright pink from the whipping he had already endured, and a heavy weight swung slowly as it dangled on the end of a cord that was tied tightly around his balls. His chest was covered in clothespins, with the heaviest concentration surrounding and covering his nipples. He was blindfolded and gagged, and he was clearly in pain.

Miss M. circled him casually, whipping his belly a couple of times, causing him to spasm in agony and whimper through his gag. “What’s the matter? You don’t want to be seen like this?” She lifted a foot and gently nudged the weight hanging from his balls. As his muffled scream filled the room she leaned down and whispered in his ear, “You should have thought of that before you made us all think you were dead.” To bring her point home she whipped him a few more times in quick succession, then let him rest for a moment.

While his cries were fading to a pathetic whimpering again, she strode over to us with a smile and said, “Well lookie here, he brought a friend.” She gestured for us to silently follow her to his side. “I wonder who it could be? Maybe it’s the mayor, or maybe the chief of police. Maybe it’s one of the protesters, after all they already think you deserved to be punished, maybe they just get to see it first hand. Maybe it’s one of the social workers at the Hathaway, wouldn’t that be nice? Every day you’d be acting all macho and tough, but he will only be able to see you like this, tied up like the bitch you are, taking whatever punishment I decide to give you.” She dragged the riding crop along his torso as she continued to circle him. “Maybe it’s that guy you were busy fucking when your family needed you most!” With this she swiped at one of the clothespins on his chest, causing it to pop off and fly across the room. He flinched and let out a muffled protest. “Oh, did that hurt?” she mocked. “Well how does this feel?” With one great sweep she knocked all the clothespins loose and they clattered throughout the room. He convulsed with such force that he would have torn the sling from the ceiling had it not been hung with chains, and his howl of pain seemed barely contained by the gag.

She continued to taunt him, reattaching clothespins, kicking the weight, and whipping him at will, until she reached for a dildo and said, “Enough foreplay, Let’s get down to business.” She stroked his face with it so he would know what was coming. “Are you ready for this?” she said, not so much as a request for his permission, but as a warning that it was coming whether he wanted it or not. He nodded his head yes, but she wasn’t satisfied. “I want to hear it,” she said as she undid the gag. “Beg for it.”

“Please…” he muttered as he tried to catch his breath and work his aching jaw.

“Please what?” she demanded as she beat his chest with the dildo.

“Please give it to me.”

“And where does my obedient little bitch want it?” she teased.

“In the ass,” he begged. “Please put it in my ass.”

“Good boy,” she cooed, moving the dildo down his torso toward his crotch. “I’ll do as you ask, but first…” With a sudden smooth movement she pulled it back up to his face and forced it into his mouth. “...I think you need to swallow it.” He gagged and struggled as she forced it down his throat. “Swallow...swallow…” she ordered as he tried to pull away. She slid it in and out, giving him short breaks to breathe before forcing it back in. “All the way...that’s it, get it nice and wet.” Finally she was satisfied that he had suffered enough and pulled it out. “That should do,” she said as he wretched and coughed, trying to regain his breath.

As she moved to attack his ass, she looked at us and said, “Get ready.” We looked at each other in puzzlement and then turned our confused gazes to her. She rolled her eyes, “Get your dicks out, You’re his gag from now on.” We looked at each other with big eyes, we hadn’t expected this, but at the moment, Miss M. was not someone to be argued with, so we both dropped our pants. “Good,” she said when she saw we were both rock hard. “Who’s going to be first?” she leaned forward and asked Helmut, “You like having strangers stick their dicks in your mouth, don’t you, you little slut!”

He had regained his breath and chuckled, “Won’t be the first time.”

She took offense at this and shouted, “Yes Ma’am!” as she once again kicked the weight, sending it swinging violently.

He tried to double over but the restraints wouldn’t allow it. Opening his mouth to scream, he could not manage to make anything beyond a tight whimper come out.

“Someone stick a dick in there and keep him quiet…” she demanded. When we looked at each other in disbelief she ordered, “Now, ladies. Now!”

As I straddled his head and slid my dick into his mouth, she disappeared under him and he began to struggle in discomfort. My dick wasn’t nearly as big as the dildo she had just forced down his throat, so I knew it wasn’t because of me. When she popped back up she was holding the weight. “There, is that better? I bet it is.” She set the weight aside and gathered his balls in her hand. “Are these puppies a little tender? Yes, I imagine they must be. Does this hurt?” She gently rotated them in her hand and he shifted uncomfortably, but did not seem to be in any great distress. “How about this?” She placed her other hand on top of them and began to squeeze his balls between them. This time she got a response. He was suddenly writhing in pain and my dick could feel the vibrations of his voice as he tried to scream. “More?” she asked innocently, and squeezed even harder. His struggles increased, but to no avail. After a moment she released his balls and his screams diminished into sobs.

“Switch!” she ordered motioning at us with her head to indicate that Ben should take over as the gag. For the brief moment when he didn’t have one of our dicks in his mouth He gasped for air and sobbed outright. Once Ben was in, she turned to me and said, I think he might need his nipples tortured from time to time. Use your own discretion, but don’t hold back. No matter what.” I nodded and gave one a quick tweak. She looked at me in disbelief. “Really?” she said, “I just had a whole package of clothespins there. Give it all you got!” I squeezed harder and got a little response from him, but she coached me, “Harder...harder, use a fingernail….now twist it...That’s right...dig that nail in harder...good.” Helmut was writhing in pain by the time she stopped giving me instructions, and she returned her attention to his ass.

“Well,” she addressed him, “the moment of truth. You ready for the real thing or do you want to be warmed up first?” He tried to mumble something but Ben’s dick prevented his sounds from being understood. “No preference? Fine, I’ll decide. Hmm…” She spread some lube around his hole and picked up the dildo that she had choked him with. It was still wet with the slime she had gathered from his throat, and without warning she thrust it deep inside him. He again convulsed, nearly knocking poor Ben over and bucking his hips as high as he could manage. She showed no mercy, easing it almost all the way out, only to shove it back in hard when he started to relax. She continued this until his responses slowed, then she started to stroke his dick.

For all the pain she had put him through, I was surprised to see that he had a raging boner. Her tone softened, but she remained in charge. “Are you ready for the real thing?” she asked. He nodded and she motioned for Ben to remove his dick. “I want to hear it,” she instructed with quiet intensity.

“I want your dick in my ass.” He was breathless with anticipation. “Please give it to me.”

“Why should I?” she asked haughtily.

“Because I’m your bitch and I deserve to be punished. Please punish me.”

“What do you guys thing? Should I punish him or make him wait for it?” She again held a finger up to remind us not to speak. We both nodded yes. “So I should punish him?” she queried. When we continued to nod yes, she leaned forward and whispered, “You’re in luck, the jury has decided on a quick and thorough ass fucking. Are you ready to receive your punishment?”

By now he was writhing in anticipation. “God, yes!”

Without a word, she reached down and unsnapped the studded jock strap that had been holding her dick tightly in place. It burst forth, seeming to revel in its newly won freedom. Ben and I looked at each other then down at our own rigid dicks. She was at least three inches longer than either of us, and almost as thick as a forearm. She smiled at the shocked looks on our faces as she lubed it up and began forcing it in. but her attention was soon devoted to administering her punishment to Helmut. She began slowly and would stop every so often to catch her breath. If she took her dick out of his ass he would immediately start to whimper at how empty he felt, and when she returned it, he would breathe a great sigh of relief. Sometimes she would lean forward and lift his head up so she could kiss him. As the pace and intensity of her thrusts started to quicken, and it became clear she was nearing climax, she started asking a series of questions. “Who’s my good little bitch?”

“I am, I’m your bitch.” he answered

“Whose balls are these?” she asked as she moved her hand off his dick for a moment to give his balls a quick squeeze.

He flinched slightly and replied, “Yours, do whatever you want with them.”

Returning her hand to his shaft and pumping furiously she continued, “Who has the biggest dick you’ve ever seen?”

“You do. My god it’s so big!”

“And who’s the most beautiful drag queen in the world?”

“You are, Daisy, you a…” His answer trailed off into a nonverbal cry of ecstasy as ropes of hot cum erupted from his dick and splattered all over the front of Miss M.’s shiny red corset.

“Good boy!” was all she could manage before she was overcome by her own ecstasy, doubling over, and falling on top of him in convulsions as her balls emptied themselves deep into Helmut’s hungry hole.