I suddenly realized I wouldn’t be able to get a safe word out if I needed to, but Karen seemed to read my thoughts, “I read about something you could do instead of saying a safe word,” she said. Then she pressed a small rubber ball into my left hand. “Just hold this and let it go if gets to be too much, okay Baby?”
I nodded my understanding and squeezed the little ball, hoping I could keep it right where it was.
“I want to be naked while I whip you Jack,” she announced, and proceeded to undress away from my sight. I could hear her breathing heavily as she did and grew harder knowing she was getting excited all over again just from the anticipation of whipping me.
A minute later she appeared alongside the bed, naked and holding the Scottish tawse in her right hand. She held it out so the leather straps touched me between my shoulder blades and then she trailed them down along my back and over my ass.
“I’ll start slowly Jack and gradually start hitting you harder, just like last night. And I’m sorry but I guess it won’t end until I’m hitting you pretty hard.”
With the ball gag in my mouth I could only make an “Mmm-hmm” sound.
She left the tawse draped across my back, reached over to the butt plug still inside me and started to slowly pull it out. Again it hurt as the bulging part of the plug stretched my sphincter.
“I don’t want anything distracting you from your whipping,” she told me. It was a relief when she finally pulled it all the way out, but I couldn’t stop wondering what else was coming… until she bent down and whispered in my ear.
“I’m going to whip your back now Baby,” she said, “and then I’m going to fuck your ass really hard with that strap-on.” So I was going to be fucked, something I actually dreaded more than the impending whipping. It almost made me want the whipping to go on as long as possible.
The first strikes of the tawse across my shoulder blades were relatively light as she promised but the instrument still made a loud snapping sound when the leather straps met my skin. She struck me again and again, moving slightly downward with each stroke until finally reaching the small of my back.
The sting from the lashes spread a heat over my entire back. Karen paused, stroked my hair and said, “I love whipping your back, it’s really getting me hot. I’m sorry but I have to start hitting you harder now.”
Then she started over again on my shoulder blades, bringing the tawse down hard. Each lash was like a hot flame across my back now, burning and then receding into a persistent sting. She whipped me again and again, a little lower each time until she once more reached the small of my back. I held the little ball tightly in my hand.
She paused once more to stroke my hair. “Are you looking forward to me fucking you in the ass, Sweetheart?” she asked me. I tried to make a negative-sounding “Mmm-hmm” sound through the ball gag but I don’t think she understood me.
“I guess it will be more fun than this whipping is,” she said, “although I’m going to have to fuck you as deep and hard as I can.” I nodded my understanding.
“But before I do that I have to whip you really hard,” she added.
Without waiting for a response from me she brought the instrument down as hard as she could across my shoulder blades, bringing from me a guttural cry of pain into my ball gag.
“Oh yes, that’s what I want to hear Baby,” she said, and once again the tawse began a journey down my back as she whipped me even harder. I was crying out into my gag with each stroke and my tears were coming fast. I squeezed the rubber ball as hard as I could.
I could hear her breathing harder until she was moaning with each blow, and glancing over at her I saw she was rubbing her pussy with her left hand as she whipped me with her right.
By the time she reached my middle back she was gasping with each stroke. She whipped me faster and faster and I knew she was approaching another orgasm as her gasps turned to cries, which sounded just like my cries of pain; we were crying out together in pain and pleasure and it drove me as deep into subspace as I’ve ever been, feeling at one with this woman in the most intimate way imaginable.
When the tawse finally crashed down on the small of my back Karen stifled a scream as she climaxed and threw herself over me on the bed. Lying across my burning back she continued to rub her pussy and cry out her pleasure as her orgasm went on and on.
She lay still for a few minutes as she recovered, her breathing slowly returning to normal as the fire on my back gradually cooled to a dull roar. Finally she moved her body to lie against me on her side, drawing her right leg up and over me. I could feel her wetness on me as she kissed my face and whispered “Oh Jack, God that was so good Baby, so good. Now I’m going to fuck you.”
She got up and went out to the living room, and reappeared a few minutes later wearing the strap-on. She stood next to the bed directly in my line of sight and fondled the realistic erect cock protruding from her crotch as if to give me time to fully appreciate it — along with the knowledge that my asshole was its destination. I was about to get fucked, and there was nothing I could do to escape my fate, except for letting go of the rubber ball I still held.
To my surprise though she took the ball out of my hand and removed the ball gag. Then she clambered up onto the bed, getting on her hands and knees perpendicular to my sideways-turned head, and lowered her hips down to my face. When the tip of the silicone cock touched my lips I realized that my mouth was not to be spared.
“Suck me Jack,” she said, “suck my hard cock.”
I opened my mouth to let it in. Karen began to gently rock her hips to move it in and out me, pushing it into me a little deeper each time. When it was only halfway into my mouth I gagged on it.
“Relax and take it in,” she said. “All of us women have to learn this, with you guys always sticking your cocks in us everywhere.”
She continued to slowly fuck my mouth, sometimes holding her cock still for a few moments after pushing it in. I realized I was thinking of it now as “her cock,” and did my best to hold back from gagging to let her have her way with me.
Soon she began making sounds of pleasure again. “That’s it Baby, suck my cock, take it all the way in,” she said, “Make it good and hard so I can fuck your ass with it.” Of course on one level I knew the silicone cock was already hard — but on another level I felt like I was being forced to assist in my own rape.
“Mmm, I like fucking your mouth Jack,” she said. “I wish I could cum down your throat with my cock.” I wished she could as well.
She thrust it into me again and again and I learned to take it. Finally she touched the back of my throat and held it there, moaning with pleasure. Then she slowly withdrew and climbed off the bed, stopping to whisper “ass time” in my ear.
I watched her pick up the tube of lubricant and apply it generously to her cock before getting back on the bed and kneeling between my bound and spread legs, and the next thing I knew she was pushing a cold glob of the lubricant into my asshole. Then she moved her body up over me, supporting herself with her left hand as she positioned her cock with her right. I felt it touch my ass cheeks and tensed up.
“Try to relax Sweetheart,” she said. “It’s going in whether you like it or not and it’ll be easier for you if you relax.”
Karen guided the head of her cock with her hand until it made contact with my asshole and then she slowly began to enter me. I tensed up again and it felt awful. She withdrew, applied more lube and put her cock in me again. As she pushed into me I tried not to resist, and she slowly pressed it in more. Suddenly it slid forward and I gasped in pain.