I WAS A LITTLE TOO HARD ON MY PUSSY BOI THE OTHER NIGHT…

He did disrespect me over the phone.  A little.  The disrespect however was a result of me playing games with him by calling him at work.  My boredom (still waiting on contractors to get their crap together ), and my innate bitchy nature led me to treat his small infraction as a greater one.

I also failed to take into account that I’ve been turning his life upside down, forced him to break up with someone he had dated on and off for years, and this is the first time in his life he’s been in chastity.  My poor boy is under some serious stress.

He came over promptly at 9 still wearing a rumpled suit and looking tired.  He was carrying a bag of antiseptic numbing cream I ordered him to get.  I met him at the porch in full Domme attire.   A leather corset/bustier, polished leather knee boots, and skin tight leather gloves.  I was also wearing my big flesh colored strapon.  It’s a larger one, about 10 inches and very thick.  I had already coated it with a thick layer of oil based lube.  I like using that instead of Butt Butter when I’m in a disciplining mood.  It lasts forever, and fills a man’s bowels with a sticky slick gel that doesn’t wash out easily, and will be felt for days.  I was holding my favorite little toy of pain, a 2 foot flexible rod I call Screamer.  I was all dressed up, but the problem was…It’s Texas, and even at night, which it was, it’s hot as hell.  I was sweating like crazy, which made me doubly irritated.

I met him at the porch, and I told him in my best pissed off voice to take his fucking ass to the stables, strip, and wait for me there.   He said ‘yes ma’am’, but it was said in a way that seemed slightly defiant, which even further angered me.

I watched him disappear inside.  I lit a long cigarette, and locked my dogs on the porch then walked to the stables.  He stood there naked, looking at the ground as I’ve taught him. His jaw seemed rather set however, so he wasn’t happy about something.   A condition I full intended to cure. 

Earlier that day I had a couple of construction workers who have been working on my stables move a heavy massage table from my screened porch, to the stable.  I had attached leather restraints to the table legs days ago, and had forgotten to take them off.  The workers that moved my table either had very good poker faces, or they just didn’t know what it was.  I’m betting the latter.

I grabbed one of my saddles and laid it horizontally across the table and told him to lie down on top of it.  He did so with care but it took a moment because he’s wearing that ridiculous cock cage which is really too large for him, and is way too heavy for day to day use.  I hooked him into the restraints.  The saddle was at about the level of his pelvis so his cute ass was sticking up nice and high.  I rubbed his pretty little mounds with a touch of lust and longing. 

“Do you know why I am disciplining you?”

“Yes Ma’am.”

“Why?”

“Because I whispered yes Ma’am and yes Mistress on the phone instead of saying it clearly.”

“And why did you not say it clearly?”

“Because I was embarrassed, and knew my co-workers wouldn’t understand.”

I was actually surprised he said it in that way.  It was completely honest, and I can work with honest.

My first stroke was to the back of his legs and he went almost completely white with shock (they always do that), followed by a high pitched hiss.  I waited precisely 8 seconds (like I do with every stroke),and struck the bottom curve of his buttocks.  I got a nice brazen yell, and a little thrashing. My third was a little higher on the buttocks, and I heard the first “Oh God, please…”

The next stroke brought the water works, and the pleading.  (Most people have zero idea what it’s like to be struck with a rod or cane. If you’re thinking that it will take lots of strokes to get you crying you would be completely wrong.  I’ve had some real tough guys on my table.  I’ve never gone over 14.  Ever.)

The 6th stroke broke him completely, deep uncontrollable sobs with heart felt pleas.  He told me how sorry he was, how he would never do it again.  I said nothing and waited 8 seconds and struck again, he screamed briefly and just continued to sob.  His ass was streaked with huge welts, and a few spots of blood. They would bruise up a little over the next few hours.

My 8th and final stroke brought a high pitched hoarse scream followed by more deep sobs.  He promised me he would never do it again with trembling lips, and big round tears.  I walked slowly in front of him, my greased strapon dangling obscenely in front.

“Are you sorry for what you did Cunt II?” I asked in an uncaring monotone.

“Yes Mistress, it’ll never happen again.”  He said sobbing.

“Are you certain this issue is closed, or do you need more instruction?” I said again in a monotone.

“No more, please Mistress.” He said sobbing harder.

“Very well Cunt II You sound honest and truly sorry.  This matter is closed.”  I said plainly.

I walked around behind him and carefully washed his buttocks and the back of his legs.  I liberally spread numbing cream over his bottom, and told him I would return in 10 minutes to let him think about what he did.  He continued to sob as I left, but his crying was getting less intense.

I poured myself a glass of Crown Royal whiskey over ice, lit another long cigarette and sat on my porch.  His honest answers and my weak justification for his discipline were weighing heavily on me.  I found myself in the strange position of caring about him enough that I needed to feel justified and right about the things I did.  It’s crazy I know. I just whipped a man, and not ‘play-around’ whipping either.  This was the real fucking deal, for an offense which amounted to….nothing. 

For the hundredth time I wished Cunt II was a deserving little bitch with just enough asshole in him that I would feel happy and justified.   It’s funny, I often wished for a longer lasting more ‘real’ Femdom relationship,  and now that it looked like I had it, I didn’t know what to do.

After 10 minutes, I walked to the stables.  He had stopped crying, turning his head the best he could to see me approach.  I smiled encouragingly to him, (Something I never do), and straddled his poor abused ass.  I slid the head of my cock between his reddened cheeks and pressed it against his little pussy. 

I always fuck a man after whipping him.  Expressing your authority in a strong way shortly after giving him pain solidifies the lesson.   The person giving the lesson and their authority is just as important as the lesson itself.  Fucking a man takes him to a deep submissive place.  A place where he respects not only you, but your word.  It also is part of the feminization process; the stern hand of discipline, and pleasure coming from the same authority.

I was gentle tonight.  It was a large strapon and he was eager to please me after the spanking.  I fucked him slow and evenly, with lots of kisses, lots of love, and telling him how proud I was of him.  He didn’t cum, but after 20 minutes or so I milked his prostate with the strapon and drained him dry with little a continuous, leaky, dribble.  I know it didn’t satisfy him, but I’m certain it eased some of the pressure of chastity.

I let him get cleaned up, and sent him home just after midnight.  He seemed tired but no longer in a dark mood, and he showed me nothing but love and respect.

It took me a long time to go to sleep that night, and I promised myself to be just as honest with him as he was with me.  If this was going to last, I had to get as real for him as he was with me.