“I guess to some extent I am, but it’s not really that I just like pain… it’s exciting when I know that hurting me is turning you on.”
“You were telling me last night about how pain and pleasure got mixed coming from the nerve endings from your ass.”
“That’s right.”
“What if I whipped you on your back? Wouldn’t that just hurt, and not be like, you know, sexual?”
“Um, yes.”
She was quiet for a moment, seemingly lost in thought. “You remember those cowboy movies I told you I liked watching as a kid?” she asked.
“Yes,” I replied. “You liked it when a guy got whipped.”
“Well, when a guy got whipped it was always on his back. If I wanted to whip your back, would that be okay?”
“That would be fine if it excited you Karen.”
“Um, it would… I think I want to do that later. I’ll start slow again like you asked.”
“That would be good,” I said, as my cock throbbed painfully inside the spiked cock ring.
“Do you know what the hottest part of last night was for me?” she asked.
“Um, no, what was it?”
“When you started crying while I was whipping you. That’s kind of sadistic, isn’t it?”
“I think that’s pretty hot,” I said.
She reached over and began toying again with my trapped cock. “Some time Jack, when we’re in a place where we can make all the noise we want, I’d like to whip you until you scream. Would that be okay?”
I winced as my cock swelled even harder against the cruel spikes. “Yes,” I said.
“Mmm, I can tell it excites you. Oh God, that thing must really be hurting you now.”
“It is.”
“I’ve got to use your mouth now Jack, I’m so hot for it,” she said breathlessly.
She lifted her hips and pulled her skirt up to her waist, and then she pushed her panties down over her legs and kicked them off. She lay back on the couch, parted her thighs and put her left leg up on the coffee table to give me full access to her. As she pulled my head down to her lap with the leash she told me to get on my stomach, and she helped me move my legs up onto the couch so I could. The spikes hurt even more as I lay down with my cock under me against the cushions.
After I got into the position she wanted she pushed my face against her crotch and said simply, “Lick.” My mouth found her soaking wet pussy and I began eating her, swallowing her juices as I worked my lips and tongue on her.
As she began to moan with pleasure I could hear her fumbling with some items from our shopping bag and a minute later I felt something cold and wet pressing at my ass cheeks and quickly finding my asshole, and then an insistent pressure as she began to push the lubed butt plug into me.
Helpless to stop the inevitable with my hands cuffed behind me, I groaned into her pussy as she pushed the plug in deeper, and she responded by moaning louder and grinding herself against my face. I didn’t know what size she was using but it felt like it was too big for me to take.
I gasped when she gave it one final push and my sphincter suddenly closed over the recessed part of the plug, and Karen said excitedly, “Oh yes Baby, it’s in you all the way now.” I was nearly in tears from the pain from my cock on top of the discomfort of the plug stuffed up my ass but I kept on eating her out as best I could.
Her breathing got faster and more urgent as pressed harder on my head with one hand and on the butt plug in my ass with the other. Suddenly she cried out, “Oh God, Jack, I’m going to cum,” and moments later, “Ahh, ahhh, oh GOD!” as her body shook from the orgasm that overcame her.
She stroked my hair as her breathing slowly returned to normal and I kissed the wet insides of her thighs, her juices smeared all over my face. “Oh God, Jack, that was so good, I came so hard Baby,” she said. “Now I want my favorite after play.”
She slid further down on the sofa, raised her hips up and spread her lags wider, and I knew what she wanted as she pushed my head down. She reached around under herself and pulled her ass cheeks apart as I moved my mouth from her wet pussy down to her assshole, circling it slowly with my tongue before touching the small opening and entering her.
“Yes Baby, mmm that feels so good after I cum. Fuck my ass with your tongue Jack.” I pushed my tongue deeper into her ass and explored her inside, slowly moving it in and out of her. “Ohhh, yes Baby, I love that,” she sighed.
Finally she tugged at my leash and helped me back up to a sitting position, adding to the pressure of the butt plug still inside me, and rearranged herself as well. She looked at my cock, which had now turned an alarming shade of purple inside the steel cock ring, and without a word she went into her purse to retrieve the small keys and mercifully unlocked and removed it. There were angry red dots all over my cock from the sharp screw points but the skin wasn’t broken anywhere.
Karen held the glass of wine to my lips and I gratefully drank from it, then she finished it off herself and reached over to stroke my cock. As my long suppressed erection began to grow she said, “Poor Baby, I guess you want to cum yourself?”
“Yes,” I replied.
She was quiet for a few moments before saying, “I’m sorry Jack, I know you must want to, but I want to tie you up and whip you first.”
I swallowed hard, remembered our recent conversation. “I understand,” I said.
She got up from the sofa and straightened her disheveled skirt. Then she pulled at my leash indicating I should stand up, picked up the shopping bag and led me into her bedroom. Being led on a leash to what was sure to be a painful fate made me weak in the knees.
Karen never said a word as she buckled the wrist and ankle cuffs on me. She then had me lie facedown on the bed and went to work cutting the bondage rope we bought into four segments and securing each of my limbs to a bed post. It was a queen size bed and my arms and legs were spread wide.
“Raise up,” she said, and as she shoved a pillow under my hips to elevate my ass I suspected that a whipping wasn’t all that lay ahead of me on this bed.
Finally she took the ball gag out of the bag, placed the ball in my mouth and buckled the strap tightly at the back of my neck. “I wish I could hear you scream Jack,” she said, “but since we’re in a hotel that will have to wait.”