I was then directed to come to Headmaster as he sat in his chair, assume position 2 and suck his very hard cock. I did this with joy, trying my best to take his full length down my throat. When I was given permission to use my hands, I twisted up and down as I sucked the head, my glistening cunt spread wide and throbbing.
Headmaster then directed me back to the ottoman, stood over me and twirled the flogger over my body as adrenaline coursed through me in anticipation of one of my favorite toys. I moaned as he struck my breasts, belly and inner thighs with the flogger. I must have made my enjoyment too obvious for he soon placed the handle of the flogger in my mouth commanding me not to drop it and moved on to the dreaded cane.
The cane is a thin stick which looks harmless enough but packs an awful stinging bite. Headmaster applied the cane to my inner thighs as I cried out my pain.
I was told repeatedly to be quiet “it won’t make it an easier,” yet this was the one order I had the most trouble following. When the pain is nearly more than I can bear, I have to release it from my body somehow. That somehow for me is crying out. I think bearing his discipline in silence will be one of my hardest lessons to learn from my Headmaster.
Headmaster lifted my leg, unbuckled and removed one sandaled heel. I thought perhaps he would suck my toes, but I was not at all prepared for his true purpose.
The cane met the bottom of my foot with blinding pain. I cried out and instinctively jerked my foot away from him, my body covered in a sheen of sweat.
He leaned over me and snarled, “Don’t pull away from me. Don’t you EVER pull away from me, do you understand?”
I nodded that I did, and God... help... me... he moved back to my foot. I considered using my safe word at this point. I felt it forming on my lips, hoped that Jay might say it for me, but he watched in silence. I couldn’t bring myself to say it as it seemed somehow a badge of failure to me; and so I endured two more licks on the bottom of the foot by the cane, each time disobeying by crying out loudly and pulling my foot away.
Headmaster then had me stand and directed me to remove my other heel. I unbuckled the shoe and tossed it off my foot. I was immediately grabbed by the hair my head pulled down to his seated level,
“Now did that seem appropriate to just toss your shoe like that? That’s something an obstinate child would do. Are you a child?”
“No Sir. I’m sorry Sir.” I managed.
He then sent me to retrieve a condom from the bag. I brought it to him and began to open the wrapper. Again I had done the wrong thing.
“Did I tell you to open it?”
“No Sir,” came my humble reply.
In time he told me to open it, and then place it on him.
I was directed to turn around and sit on his cock. I instinctively began to rock back and forth and was ordered to be still and just sit on his cock. When I complied, I was told I could rock slowly back and forth. I began to move slowly on his cock enjoying the sensations inside my cunt as Daddy approached me and placed his cock in my mouth. I sucked Daddy’s hardness while I bounced on Headmaster’s cock. What a lucky girl I was.
When Daddy was satisfied, he sat back to watch me bouncing harder and harder on Headmaster’s cock. When I was close again Headmaster pulled me backwards by my leash, my collar choking me as I leaned back against him. Thankfully I was given permission to cum because I could no longer control my arousal and was flying towards an unstoppable orgasm.
My strangled gasps filled the air of the hotel room as I came. When it was finished, I leaned forward onto the ottoman, panting and sweating, his cock still inside me as I tried to regain my senses.
He struck me along the back and ass with the cane, this time eliciting deliciously pleasurable sensations.
I began to bounce up and down on his cock harder and harder until my nipples were in agony. My bouncing came to a stop only to have him thrust hard from underneath me as I cried out, “my tits, Oh God my tits”; again an instance where my safe word was needed yet I did not want to fail in using it.
I was able to push past the pain and began to thrust violently on his cock again until my thighs were burning and I was gasping for air as hard as I do after a 4 or 5mile run.
I eventually dismounted his cock and stood only to be pulled down to his level by my hair.
“We have learned some lessons today, haven’t we?” he questioned.
“You were brought here to learn your place and learn to be more obedient to Daddy."
"We all know that you like to test limits. The lessons learned here are to be carried beyond this room otherwise I am wasting my time. Do you want me to waste my time?”
“No Sir,” I replied.
“Good girl. Now repeat to me what I have said and what you have learned here today.”
“That I am to take the lessons here and apply them in the world outside this room. That I am to learn to be more obedient to Daddy.”
“Good girl,” he crooned.
I was then sent on my hands and knees to retrieve a warm wash cloth and carry it back in my mouth. I was then directed to remove his condom full of his seed and clean his cock and balls with the cloth. I was made to repeat the whole process for Daddy minus the removal of a condom.
I was then sent to retrieve the dildo still stuck on the mirror. I couldn’t bring myself to put it in my mouth and attempted to crawl with it in my hand.
“Is that how you are to bring things to me?” he asked.
“No Sir,” I responded as I gripped it in my mouth.
When I returned to kneel before him my bottom was caned as he chided, “I gave you two examples of how you are to bring things to me and you made a conscious choice not to do it, didn’t you?”
“Yes Sir. I’m sorry Sir. I’ll do better Sir,” I responded as the cane dealt its discipline.
I was then sent to fetch various other things with my mouth and generally tidy up the room.
I then dressed him as I knelt before him... I placed his underwear on him which I had retrived with my mouth, his shorts, and his belt.
By far the worst thing I was made to retrieve with my mouth were his shoes and socks. I hesitated over them, horrified at the notion of putting them in my mouth, but too spent to endure much more punishment so I complied and carried each sock and each shoe to him in my mouth. When I had fully dressed him, I placed each sock and shoe on his foot and tied them.
He then sent me to retrieve my dress at which Jay stopped him saying he was not done with me and wanted me naked.
Headmaster again sternly reminded me this was just the first of our lessons. I was to take what I learned beyond just today’s session. Future sessions would increase in intensity, most especially in the discipline dealt for disobedience.
"Yes Sir,” I replied humbly.
After he and Jay shook hands, he left and Jay and I were alone in the room. My dearest Jay laid me back on the bed and sunk his hard cock into me. We fucked with our own particular rhythm, his cock rubbing just the right places inside me until he came with a moan, warm, wet and familiar inside me.
Jay and I have embarked on a new world of sex and discipline which is exciting to each of us. Much has happened in the week since this particular session which I am eager to share with you in upcoming posts.