She was only gone for a minute, but it felt like an hour before she walked back in and stood before me again, hiding her new toy behind her back.
“Do you remember when I talked about watching cowboy movies when I was a kid and obsessing on the scenes of guys getting tied up and whipped?” she asked.
“Oh yes, I remember,” I replied.
“Well, it’s not like they were using a tawse… it was more something like this.”
She brought her left hand out from behind her back to display her purchase. It was a black leather single tail whip.
I was speechless for a few seconds. “Uh, is that like a miniature bullwhip?” I finally asked.
“It’s called a signal whip,” she replied. “I actually thought about getting a bullwhip but the guy at the store recommended this for beginners, it’s only 4 feet long and he said it would be easier to control and safer to use.”
“Well,” I said, “safer sounds… good.”
She uncoiled the whip, dropped the end down to my cock and slowly looped it around the shaft.
“This would hurt more than the tawse, maybe a lot more. But I’ve practiced with it, on a pillow, and I’m pretty sure I can use it without breaking the skin. It’s easier to target this kind of whip than with the bigger ones.”
I went a little weak at the knees hearing her say “target,” knowing this meant places on my body. Places that would probably soon be feeling the business end of this new whip.
“Do you want to use that on me, Karen?”
She looked at me with eyes that were a little sad, and reached up with her right hand to caress my face. “Yes Jack, I do… seeing you chained up like this and holding this whip in my hand makes me want to use it… my stomach is doing flip flops, I’m so turned on.”
“If using that on me would excite you, then… I want you to.”
“Do you really mean that?” she asked me. “I couldn’t stand it if you thought I was too weird for you. Are you sure you want a crazy girlfriend that gets off on whipping you?”
“I think you already know the answer to that,” I said. “Look at your whip.”
She looked down at the whip looped around my cock and saw that I was hard as rock.
“Oh Baby,” she said, wrapping her arms around me, “I love you.” She leaned up and kissed me, and reached down to fondle my rigid cock again. It throbbed to her touch. “I love you too,” I said.
“You’re turned on too, aren’t you,” she said, squeezing some precum out of my cock. She put her fingertips on my lips and spread it over them, then reached back down to squeeze out more. “Open your mouth,” she said, and pushed her wet fingertips inside me so I could lick them clean.
“You remember your safe words, right?” she asked.
“Yes, and you remember I might beg you to stop but you don’t have to unless I use a safe word, right?”
“Oh yes… you know, when I bought this it was going through my mind how much it would make you beg for mercy… I know it’s weird, but I like hearing you beg.”
“It’s not weird Karen, it’s fun for me too.”
“Okay Sweetheart.” She unlooped the whip from around my cock and brought it up to my face.
“If I use this on you it will be on your back, your ass, and your thighs. I’ll go easy on you at first, but I’m really in the mood to whip you until you’re crying and begging for me to stop.”
“I understand.”
“But you know I won’t stop Jack, and your begging will just make me whip you harder.”
“I know.”
“Then kiss the whip if you want me to begin.”
She held the signal whip to my lips and I kissed the braided leather, and then Karen moved behind me. She cracked the whip in the air a few times and the sound made me jump in my chains.
“Sounds scary, doesn’t it?” she asked.
“Yes,” I replied, with a catch in my voice.
“Are you scared?”
“Yes.”
“I don’t blame you. Well you won’t be scared much longer, just in a lot of pain.”
She held the end of the whip, touching my back with it to measure off her distance, and I suddenly realized I was trembling with fear.
Without warning she swung the whip, striking my back diagonally across my shoulder blades. I felt nothing for a split second and then a burning sensation spread across my back. She paused, seeming to instinctively know the arc of my pain as it rose and fell, and then she struck me again, this time slightly lower than before.
“Oh,” she said, “I wish you could see the red stripes this makes. It’s like I can paint your back with this.”
The third lash was harder, and I groaned through my gritted teeth.
“That hurt more, didn’t it?
“Yes, it did.”
The fourth lash was harder still, causing me to arch my body and pull at my chains. “God, that really hurts Karen.”
“Oh Baby, I love seeing you move your body like that,” she said. She swung again and struck me in the same place but this time the end of the whip curled around me and caught the edge of my right nipple. “Jeez” I shouted, twisting in my restraints, “you really are good with that thing!”
“I told you I practiced,” she said with a giggle.
Then she began punishing me in earnest, lashing me again and again in an unrelenting rhythm, gradually lowering her aim each time until she reached the small of my back. I was on fire.
I sensed she was carefully focused on making equally spaced parallel stripes on me, and as bad as it hurt the thought of her being so detached from my pain was exquisite.
Then she whipped me sideways across the top of my ass. “Ahhh, I don’t know if I can take much more of that,” I said.
“I’m so sorry Sweetheart, but I’m afraid you have to,” she said, and flogged my ass again, putting another stripe just below the last. “God, that really hurts,” I said again, but now with an edge of panic creeping into my voice.
She swung the whip three times more without pausing in between and tears were now streaming down my face. “Please stop Karen, it’s too much!” I cried.
“I know it’s too much Jack. I want it to be too much,” she said, “I want you to feel like you can’t possibly take any more,” and she whipped my ass again as hard as she could, this time making me scream.
“It’s a good thing my ex soundproofed this room,” she said with a laugh.
She put the whip down and for a second I thought she was going to stop, but then I realized from the sounds I heard that she had started to take off her clothes.
“I’m so wet Baby, I have to strip before I soak right through these jeans.” It wasn’t the first time she had undressed behind me during a whipping, adding to my pain the frustration of not being able to see her naked body.
“Now I’m going to finish striping your ass Jack, and the backs of thighs as well. And I’m going to make myself cum while I do it.” I knew the worst was ahead of me once she started her ride to orgasm.
I could hear her start to breathe more heavily as she swung the whip and I knew she was pleasuring herself with her left hand at the same time. My erection had long since disappeared but picturing what she was doing behind me almost brought it back. Almost.
As she worked her way down my ass she began to grunt with each swing of the whip, each grunt now followed by a pitiful cry from me. “Please Karen, no more, oh God I just can’t take it. I’ll do anything for you if you’ll stop!”
“Jack, you’ll do anything for me anyway,” and the whip crashed just below the bottom of my ass, that tender place where the tops of my thighs ended. I screamed bloody murder.
Then she went to work on my thighs, and on one particularly brutal lash the whip curled around and managed to catch the side of my balls. I howled in pain and as I did Karen cried out, “I’m cumming, Oh God, OHH GOD, AHH AHHH AHHHH!”