Another whap with the paddle on my burning butt. That makes eight. Only two more to go and then I could relax. I kept telling myself not to cry, not even to whimper. And I was concentrating all my energy into not moving a muscle.
Although I was strapped down, ass up over the padded saw horse with my legs spread wide and my asshole gaping open, I was desperately trying to hold still and not squeeze my ass shut. Not that I could, the way I was positioned. But I needed to practice for the day when I will finally be allowed to accept my discipline without being tied down.
The Mistresses are all experts at spanking and whipping. I know this. I have yet to see any of them make a mistake and accidentally beat my exposed balls or sting my vulnerable asshole when I'm in this position. Deep down I know this. I know I should trust in them completely and yet I can't. Not yet. I can't seem to give up my fear that their aim will be slightly off and . . . .
One more to go. I could do it.
Mistress Maureen paused for a moment to take a sip from her glass of iced tea and to inspect the placement of the whaps on my butt. I could see her reflection in the window in front of me as she tilted her head to one side in thought. I wondered if she knew that I saw her.
Novice Penny was standing beside her holding a clipboard. She'd been writing down whatever Mistress had been saying about me. They keep meticulous notes here on all the slaves, I've found out. Besides the usual —— age, height, weight, measurements (including length and width of erect penis, and size of the largest dildo we have so far been able to take up our butts) —— they keep track and grade us on all our lessons, as well as our reactions to whatever they've done to us.
“Penny, make a note that I'd like to schedule Jason here for an enema for one hour from now. And see to it that the new strap-on I ordered is in my room, along with a new tube of KY. I'm going to need lots of lube.”
“Yes, Maureen,” said Penny, as she scribbled away on her clipboard.
Mistress Maureen put down her glass and slowly stretched her pitching arm, rotating her shoulder and flexing her fingers. Then she picked up the paddle again, never once taking her eyes off my ass. Here it comes, I thought. The tenth and final whap. God, I think the last is always worse than the first, because I know that she'll put everything she has into it so it'll really sting my poor abused butt. I wanted to close my eyes, but I couldn't. I needed to see her swing. I needed to know when it came.
Man, I was right. Breathe, I told myself, only now realizing that I'd been holding my breath for the last minute or so. Damn. Would I ever be able to offer my ass without holding a small piece of myself back?
I felt Mistress Maureen's hands flat on my ass cheeks, cooling them. Ah, heaven. Now came my favorite part of getting beaten: She was raising the skirt of her knee-length sheer red toga and pressing her pussy, stomach and thighs against my flaming butt, leaning over me to caress my neck and shoulders. She wriggled a bit and I felt her pussy hair tickle my asshole.
“Jason, darling,” she whispered in my ear. “You did very well. I'm going to untie you now. Hold still until I give you leave to get up.”
“Yes, Mistress,” I sighed as she stood up.
Penny unstrapped the buckles holding my thighs, knees and ankles in place. Then she undid the strap that was across my waist. Last she freed my wrists.
Mistress Maureen took my hand and pulled me to the couch where she took me in her arms to comfort me. As she rocked me a bit, kissing my temple, she told me in that gentle voice of hers that she has decided to fuck me in the ass later today. And suddenly I remembered what she told Novice Penny a few minutes ago. She's really going to fuck my ass! With her strap-on!
Since my arrival here at the Compound, I've had my asshole filled with fingers, enema pipes, several different-sized butt plugs, vibrators and dildoes, but never with a strap-on dildo. My ass has never really been fucked at all in the traditional sense —— by man or woman. I knew it would happen, of course. My trainer Tom explained to me about what he called “milestones.” Things to “look forward to” that would indicate my moving up to the next level in my slavedom. Milestones are considered very high honors; the highest form of a Mistress's approval of my eagerness and ability to serve her.
Two of the milestones in particular stood out just then. One is the first time a Mistress actually fucks my ass with a strap-on, instead of just holding a dildo in her hand.
The other is the first time a Mistress takes me to her bed as her lover.
Well, the second sure hasn't happened yet. But the first was going to happen tonight!
Tom, who had been sitting in the corner throughout my beating, came over and pulled me up from the couch by my elbow. Mistress Maureen had dismissed me. For now. I was still a bit unsteady on my feet, but I meekly followed Tom out the door and down the stairs to my room. I heard him running the shower for me and then calling me into the bathroom which was already getting steamy.
As I took my shower, I tried to picture myself as I'll be later, positioned on my knees, being fucked silly by a woman. A month ago, I couldn't have imagined it at all. And yet now . . . now, I was already turned on, my dick sticking straight up, just thinking about it. What's happened to me?
After I stepped out of the shower and dried myself off, I gingerly lied down face down on my bed for a tiny nap, my bruised ass throbbing. Tom was rubbing lotion into my ass cheeks, his palms gently sliding over my skin, around and around in circles, all the while telling me things I should remember for later. My training has prepared me well for this, he reminded me. I must release my will and give myself to Mistress, obey her every command. I'm to position my body in any way she requires. I will kneel down, bend over, spread my knees as wide as I can, arch my back, and open my ass for each powerful thrust of her hips.
Open my ass. Open . . . .
I drifted off to sleep.
The next thing I knew, Tom was gently shaking me awake. It was time to leave for the Clinic to get my enema.
(End of Part 1)
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