19 year old Carolina Sweets has never been tied down and tickled before. She has no idea what is in store for her. He lied and told her that he was going to go easy on her. Afterwards she told us how horrible it was being tied down and ticked
Our latest game show features our Wheel of Pain. The player must first spin for a body part & position and second she must spin for an instrument of the 12 different types.
I've talked a lot about the lovely Rain DeGrey. She has so much to offer whenever I see her. Big tits, a firm ass, a beautiful body, everything about her screams, “Torment me.” She loves pain. It's how she gets off. And it's a good thing, too, because she has a long day ahead of her.
There is a wooden post in the middle of the room that is going to provide the central structure of Rain's bondage. From there I can lock her arms and neck into place. A pair of metal pipes on the ground give me something to lock her ankles to. It leaves her tits and pussy exposed, a familiar position for her. I walk up and tell her what she already knows. Today is going to be intense.
She has been with me before. She thinks she knows the drill. It starts with some bondage, moves on to some discipline, everything gets more intense and she gets the most amazing orgasms of her life in the end. Normally that means starting with a flogger or maybe a cane. Today I'm going straight for the whip.
The lash raises welts all over her body as soon as it touches her skin. The bright red stripes start crisscrossing her body, each blow bringing out another one. They will turn into bruises tomorrow, leaving her with dozens of little reminders of how this day started. She grunts and screams with each strike, but the ball gag in her mouth muffles it all.
What is normally the finale is just the warm up today. I tied her tits off with leather thongs to restrict the flow. It makes them firmer, purple, and extremely sensitive. She should be happy to have a man playing with her tits, but for some reason the only thing she does is scream at the top of her lungs every time my paddle comes down on them.
Well, I said she likes pain with her pleasure. I decided to see how much she likes having clamps on her nipples and pussy while I give her a bit of stimulation. The celebrator is a small vibrator but it is powerful. Pressed against her clit, especially with clamps on, it can be more than enough to overwhelm a woman's senses. Rain is a screamer and this level of intensity is more than enough to have her bellowing at the top of her lungs and struggling against the shackles holding her in place.
Once I take the leather off of her tits you can see what all of the fuss was about. Her breasts are covered in the purple bruises that tell the story of the day. They won't be fading any time soon, but given how much of a pain slut Rain is I think it's more likely she'll be playing with them when she masturbates than calling me back to complain.
I plan on making the back of her match the front. I have paddles and canes ready to go, and lucky for her there isn't a very good way to tie her ass cheeks off to make them more sensitive. It means I am going to have to work a little bit harder to get the bruises to show, but anything worth doing at all is worth doing right.
Rain's turned around, but in almost the same position. The most significant differences are plain to see, though. A pair of leather straps lift her ass cheeks so that they are perfectly places for punishment. Her ball gag as been replaced with a harness that covers her mouth and connects her face to her post. It lets her see the top, which forms a nice little shelf for all of my toys. I lay them out in front of her so she can get a good look at them all. I feel like a little anticipation goes a long way.
Each one feels a bit different on her ass. Each one is going to leave a unique mark, on her ass and on her psyche. It doesn't take much to make those marks, either. The bruises are just as big and beautiful on Rain's ass as they were on her chest.
And this time, when I grab a vibrator, I go for the gold. The Hitachi has given Rain knee-quaking, body-rocking orgasms before, so she knows what to expect as I press it against her clit. All of this suffering has made her pussy dripping wet and all she wants is to feel some pleasure. This little motorized menace is going to give her more than she bargained for. Rain is used to having a quick cum and relaxing. This toy is going to tear multiple orgasms from her body until her legs can barely hold her up anymore. If it weren't for the restraints holding her up she would probably collapse to the floor in a mess of flesh and fluids.
Afterward Rain and I have a very nice chat. She tells me things about how much she loves to cum after pain, as though I hadn't know. Even better, she gives us all a good look at the aftermath of our fun times together. Her pussy is red from being worked so hard. Her ass and tits are covered in bruises. The whip marks all over her body are still clearly visible. It's been a long day and knowing Rain she'll be back and begging for more in no time.
Ivy Addams is the kind of sexy starlet that O.T. loves having in his clutches. Some girls whimper and beg from the second he puts them in bondage, and they can be fun, but sometimes he enjoys putting a particularly willful one in her place. Ivy is more likely to laugh than cry when she feels the sting of the whip, but that's fine because it will just make her eventual tears that much sweeter.
Her entire world exists withing a few feet of a set of parallel, metal pipes. Some part of her, usually her head, is forever locked between them, and so if she plans on getting anywhere she is going to need to stretch and contort to do it. Even at her most free she is hardly able to wiggle her ass without wrenching her neck. It makes for a perilous predicament as she tries desperately to avoid the single tail O.T. is wielding.
Like we said, though, Ivy has some spunk. When he is messing with her in the worst of ways, applying clamps to some of the more unconventional parts of her body, she doesn't miss a beat. Instead of breaking down in tears she has a few choice words for her perpetual tormentor. We hope that acting out makes her feel better, because the punishment for back talk is another day in the dungeon, so she is going to be here for a while.
Being wrapped with ropes is like being hugged. Kat Monroe gets a nice big hug. At first she's just sitting and waiting for OT. He's tied her and abandoned her. She struggles in the rope with the huge ball in her mouth. When he returns he drags her to the pulley and pulls her up by her feet.
Using Kat's own wrists restraints to gag her is genius. To keep it in her mouth OT pulls her into an intense hogtie and attaches her legs to her gag. She tries to pull free, but her own body holds it tightly to her.
No one likes to squat. Having to squat deeply because your neck. Is tied down and up so you can't sit or stand has to be the most painful and frustrating position. With her own stockings over her head Kat is blinded.