“That’s excellent. You suffer beautifully. Let’s get you up on the bench and get to work on that lovely bottom of yours.”
Her custom-built spanking bench was like a sawhorse. It was padded leather with shelves for the knees that were about nine inches below the top piece. The spankee would kneel lengthwise on the bench, and there was a headrest like those on massage tables.
He was positioned so that his cock and balls hung off the back end and his head fit into the headrest. His wrist and ankle cuffs were fastened to eyebolts on the bench. She wrapped a heavy strap around his middle, cinching him tightly to the bench.
She attached a clover clamp to his left nipple. He hated those clamps and sucked in his breath as he felt the bite. The pain would diminish as his body adapted, until she took them off, and then the pain would return. She walked around and put a clamp on his right nipple, making him hiss. A light chain that went over his back and connected the two clamps. When she got behind him, she pulled on the chain to torment his nipples — more hissing.
A small strap that cinched around his cock and balls and held them to the frame of the bench, further preventing him from bucking around.
She lubed up the enormous dildo, and he felt her squirt some lube up his ass.
“I’m just going to put the head in to loosen you up, and then I’ll start the spanking.”
She pushed the dildo in an inch or two, then back out, then in and out again.
“How’s that?”
“Umm, feels good.”
She showed him her leather paddle. It was thick, like heavy belt material, five inches wide and ten inches long past the handle.
Oh God, that looks fearsome. My butt’s going to burn.
She began with light strokes, counting to herself. When she got to fifty, she switched to the other cheek and put fifty on that side. His ass was turning red, and she didn’t want to burn him out too soon.
Moving behind him, she pushed the dildo in about three inches and fucked him slowly, popping the head out just enough to let his anal sphincter close before pushing in again.
When he moaned, she stopped and went back to paddling. She made the strokes a little harder this time and gave him another fifty on each cheek, alternating from one cheek to the other. She could see he was feeling it now, so she resumed fucking him with her strap-on, using the same pattern as before. When he moaned again, she pushed in until his sphincter stopped her where the dildo widened out to two and a half inches. She held the pressure against his anus.
Chase knew she was at the wide point of the dildo, and he wasn’t sure if he could take it. Everything felt good up to this point. He knew he had to go for it.
“Try pushing out and see if you can’t let it in a bit,” she said.
He pushed his anus out, but it was really stretching him, and he was afraid she was going to tear him open.
“Good. Keep pushing and I’ll keep the pressure on. Let’s see if we can’t find a new limit for you.”
She kept the dildo pressed firmly against his anus and rotated her hips, which stimulated all those nerve endings in his anus. He could feel the dildo rubbing against his prostate as she swiveled her hips. The sensations were fantastic. He’d felt nothing like it before. If it weren’t for the strap around his waist, holding him to the bench, he would shove back against her. He pushed his anus hard, and it relaxed, and the dildo slid all the way in.
“Oh god. It’s really stretching me.”
“Take a minute and breathe into it. Once your anal muscles relax, they will adapt, and it will feel good.”
She began moving the dildo, sliding in and out, just enough to keep the large section inside him.
“That feels amazing. Please don’t stop.”
“I knew you’d like it. You’re an anal slut.”
She plunged the dildo in and out in long, slow strokes. When he was comfortable taking the whole thing easily, she stopped.
“It’s time for the last phase of your punishment. Are you ready for the cane?”
“I don’t think I’ll ever be ready for the cane, but let’s get to it.”
She took up her cane and positioned herself behind and off to the side so she could get a good stroke. She began tapping his ass with the cane, getting her measure and then, without warning, delivered the first stroke.
He heard that fearsome whistle of the cane swishing through the air just before his ass exploded in pain.
“Oh god,” he cried, knowing there were five more of those coming.
“What a beautiful mark. Your ass is already crimson from the paddle and the cane leaves a deep white stripe which turns into a red weal. I’ll see if I can make a nice ladder down your butt to your thighs.”
With that, she began tapping again, measuring her stroke and he heard the whistle and again his ass exploded in pain. Without pausing, she continued tapping and laid on the next four strokes, one after the other.
“That looks so hot. I have to fuck you some more.”
She threw the cane aside and plunged her dildo all the way in. She pounded his ass with fast, deep strokes, her tempo increasing until she rammed it all the way in and started grinding against him. Her moans and cries signaled her approaching orgasm. She grabbed the chain on his nipple clamps and pulled them so hard that she pulled them off. When he screamed, she let out a shout and her hips pumped furiously against his tender ass. Her orgasm overwhelmed her, and she finally collapsed over his back, covered in sweat and gasping for breath.
Chase, too, was sweating profusely and felt like she had wrung him out to his limits. His ass was on fire, his anus felt raw and stretched as she pulled out of him.
After she caught her breath, she said, “That was amazing. I’ve never had a session like this before. You’re a unique guy. I’m going to let you up in a minute, but I want to check one more thing before I do.”
She got down behind him and started fingering his anus. “Does that feel ok?”
“Yes,” he said, wondering what she was going to do to him now. He felt toasted.
She slid her whole hand into his already loosened anus, and just held it there.
“Is this okay?”
“Yes.”
She started rubbing his prostate, massaging it gently and after a while, jism flowed out of his cock.
“Stop. Wait. Are you milking me?”
“Yes. I thought it might help relieve some pressure for you.”
“Please don’t do anymore. Let me up and I’ll explain it to you.”
She unfastened him, helped him up, and then led him over to the bed. “Let me lie on the bed and then you can lie half on top of me, and I can cuddle and stroke you. I know you won’t want to sit on your bottom for a bit.”
Once she was lying on the bed, she opened her arms to him, so he could put his head on her breast and lie next to her. He hooked his leg over hers and felt his cock up against her thigh, and it was turning him on.
“Let me hold you for a while and then I’ll get some ointment.”
“Ummm,” he responded, not yet ready to talk.
As they lay there, she planted little kisses on his head and took his hand and put it on her other breast. Not saying anything, they just laid there, feeling each other’s energy and a warm glow encompassing them.
He had positioned his palm directly over her nipple and could feel the energy coming out of her nipple. His cock grew harder against her thigh.
“I can tell you’re feeling better. Let me get some ointment to soothe your bottom.”
She wiggled out from under him and went to a cabinet and brought back a tube of gel. She began gently coating his inflamed butt.
“This gel is a combination of Arnica and Aloe and will help to heal you quicker. Would you like to take a shower? We can put more ointment on after.”
“That’s a good idea.”
“I see you still have an erection. Is there something you would like to do with that?”
“I think all I want to do is feel the sexual energy as I admire your beautiful body.”
“I like that. Let me show you the bathroom. There are towels and everything else you might need in there.”
The bathroom was enormous, with a large walk-in shower that had nozzles coming from every direction. She started the water and got the temperature right and then gestured for him to get in. Without waiting, she washed him with a moisturizing body wash. As she rubbed the soapy gel over his chest, she said, “You have an impressive body, and I love the feeling of your hairless skin. It’s so sensual. Is it hard to maintain?”
“It takes some maintenance, but I think it’s worth the effort. I like the feeling of it too. As you’ve probably noticed, I’m a slut for sensations.”
“I noticed. I like sensations too.”
Standing behind him, she continued to soap his body, carefully washing his battered ass cheeks. “Is this okay?”
“Yes, but please don’t rub any harder.”
“I’ll be careful,” she said as she slipped her fingers into his ass crack and rimmed his anus. “How about this? Is this okay?”
“That’s nice. I love you playing with those nerve endings in my anus. You can keep that up as long as you like.”
After toying with his anus, she moved her hands around to fondle his still hard cock.
‘You’re amazing. How can you be hard after all we’ve done?”
“Cup my testicles with your hand.”
“Wow, these boys are heavy. You’ve got a lot of juice stored in these balls.”
“I enjoy keeping them that way. Keeping my ejaculate keeps my sexual energy high and allows me to edge more often.”
“I want to hear more about that. Are you ready to get out of the shower?”
“I am.”
When they stepped out of the shower, she took a towel from a towel warmer and patted him dry. When he was dry, she gave him a soft terry-cloth robe, dried herself off and asked, “Would you like something to drink or snack on?”
“I would like that. Yes, to both.”
“Let’s go to the kitchen and see what we can find.”
~
After slicing some apples and cheese along with some crackers and cold sweet tea, Brigid asked, “Would you like to eat standing up, or can you sit on that tender bottom?”
“I’ll try sitting, but if it’s too uncomfortable, I’ll get back up.”
After they were sitting comfortably, Brigid asked, “Why were you so upset when I milked your prostate?”
“If I hold on to my semen, I can have full-on non-ejaculatory orgasms. That’s a tremendous source of energy for me.”
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