Jay and I had a most illuminating and erotic experience last Sunday. I have been conversing with a new friend for about a month now. We have been getting to know each other in general, and most specifically discussing my desire for a 2nd dominant.
Last Sunday Jay and I made the decision to meet with him. The parameters were set that if there seemed to be some sort of chemistry, he would dispense with the small talk and move forward quickly with what we all desired. We were to meet at a local hotel which also housed a lounge where we might have drinks and chat.
Unfortunately, the lounge was not available on a Sunday afternoon so it was agreed we would simply meet at the hotel and find a quiet place to chat.
Jay informed me that we had to make a little side stop on the way over to our meeting which turned out to be a trip to the mall where I was to pick out a pair of panties to wear to our meeting.
When we arrived at the hotel I was nervous as a cat. We walked in and glanced around the lobby to see our guest had not yet arrived, so we sat down to wait which made it even worse. He arrived not five minutes later and my heart began to pound.
We exchanged pleasantries and sought out a quiet place on the other side of the hotel to chat. We sat with Jay to my right and our new friend directly across from me.
“I understand you made a stop on your way here today,” he began.
I nodded my head in assent.
“And what did you make the stop for?” he prodded.
“A pair of panties,” I answer shyly.
“Why don’t you show me,” he replied.
I lifted my dress enough to flash him the panties.
“Go ahead and stand up and take them off and place them on the table here,” he directed.
I hesitated for a moment, glanced around to see the area was deserted, stood up, removed the panties and tossed them on the table.
“Fold them up neatly and place them on the table,” he directed in a measured tone.
I retrieved the panties from the table, folded them awkwardly, feeling silly and embarrassed and placed them back on the table.
“Do you have your rosebud in?” he queried.
I nodded that I did.
“Stand up, bend over the chair, and show me,” he replied.
I did exactly as I was told, lifting my dress to show him my pink rosebud glimmering from my asshole.
I sat back down, twirling my sunglasses nervously in one hand until I caught him staring from me to the twirling hand. I immediately stilled my hand with nothing but a look.
We began to discuss our mutual desire to check in and adjourn to a room.
“Do you understand why you have been brought here today” he asked.
“Yes Sir,” I replied.
“And why is that?” he countered.
“For training, Sir,” I responded.
“That’s right. And do you understand that you will be pushed and limits will be tested?”
“Are you ready for that?”
“Yes Sir,” I responded as my pussy moistened and a tingle of fear began to run through me.
As we reached the hall on which our room was located, our new friend which I shall refer to as Sir Headmaster going forward, turned to me and said, “You will remove your dress here in the hall.”
The hall was deserted but I could hear people moving about somewhere nearby. I looked at him nervously, unsure what to do.
“I can hear people around the corner,” I protested weakly.
“Then we’d better move quickly, hadn’t we?” Headmaster replied in an even tone.
“Yes Sir,” I responded as I quickly pulled my dress over my head leaving me entirely naked save for my heels.
I scurried behind him desperate for the privacy of the closed hotel room door.
When we entered the room, Daddy ordered me to my knees and affixed my collar around my neck.
Headmaster approached me and informed me he would be teaching me my basic positions which I would be expected to memorize and move into quickly with only the utterance of the number by him. He further clarified I was to use the standard safe words of “yellow” and “red” with which he understood I was familiar. He suggested I let Daddy call my safe words for me, but would allow me to use them as well during this first session.
Position one required me to stand, hands behind my head, chest out, legs spread. He circled me as I stood in this position explaining that this position allowed him to view and inspect nearly all of my body. My pussy grew even wetter as he looked me over as if I was a piece of livestock of which he was considering purchase.
Position two required me to keep my legs straight and lean forward at a 90 degree angle, legs still spread, hands on the back of my head. From this position I was told he could inspect areas he could not see in position one such as my pussy and ass. He could make sure I was clean and properly shaven he told me as he spread my ass cheeks and ran his finger over my dripping cunt. He returned me to position one and slowly inserted his fingers in my mouth as I sucked my own wetness from them.
Position three required me to kneel on the ground hands behind my head, chest pushed out, while position four was a position of worship which placed my face on the floor arms outstretched in front of my body.
From here on out he would call out numbers and I would comply with the position. A time or two I stumbled on what to do with my hands in position one until my head was jerked down by the hair to his seated position and he quietly said to me in his measured tone, “The hands go in the same place in each position. Why is this so hard for you? It’s not that difficult, is it?”
“No Sir,” I replied.
My leash was attached to my collar, I was ordered on all fours and made to crawl along the floor as he led me about the room, the leash taut enough to cause the collar to choke me.
When this task was completed I was directed to remove his shoes and socks. I have a thing about feet. I am not fond of touching them with the exception of my own and my daughter’s cute little feet, so I had a little trouble with the notion of removing his socks. I did remove them and immediately tossed them inside out onto his shoes. It was an act of laziness I was not going to get away with. I was immediately reprimanded and told to fold the socks neatly over his shoes right side out. I squeamishly turned them right side out and laid them neatly over the shoes as directed, my need to please outweighing my aversion to touching his socks.
He then removed his belt and I watched nervously knowing what was coming next. I was led to the bed and made to bend over it, ass exposed. I was relieved to find the strokes of the belt were rather mild and easily bearable.
I was then ordered back down on my knees and made to remove his shorts. I noted the bulge of his cock in his underwear and wondered when I would have the pleasure of seeing it. I was led about the room on all fours a few more times before being told to remove his underwear.
His cock sprang forth, large, hard and oozing with precum. He brought it to my face and I reached out to take it in my mouth only to be slapped in the face and reminded I had not been given permission to take him in my mouth. He slapped his cock in my face quite hard a few times before allowing me to take him in my mouth. I sucked and tasted as my head moved up and down.
When he pulled out of my mouth to slap me a bit more, I took my hands off my head to move the hair out of my face that had fallen down and was irritating me. He immediately pulled me up by the hair, bent over to look me in the eye and said in that measured tone of his as if speaking to a child,
“You don’t move your hands. If you need to move your hands, I will tell you, understand?”
I nodded my head that I did.
Headmaster began to rummage through the gear bag that Daddy had brought, surveying what he had to work with. He found the bag of clothes pins and began to methodically attach them to my breasts.
He then found one of several dildos in the bag. I was mortified by the one he pulled out. It had not been used in some time and was covered in dog hair from its last visit to our bed. I always thoroughly clean our toys after use. I have no idea why this one was in the condition that it was. Nevertheless I was embarrassed by my unkempt dildo.
He led me to the mirror mounted on the wall and attached the suction cup dildo to it. I was then directed into position #2, ordered to push back into the dildo and began to fuck it. As I did this, Headmaster came around in front of me and inserted his cock into my mouth. I was to fuck the dildo mounted on the mirror while sucking Headmaster. I felt a bit embarrassed by the noise of the mirror banging against the wall as I moved. We were near the door to the hotel room and I did not want to make too much noise. Headmaster began to move me back and forth on the dildo at the pace he was seeking. The mirror squeaked and banged against the wall in a most mortifying fashion.
When Headmaster had had enough I was led back to the center of the room into position one. I stood with my hands behind my head, chest pushed out as he took the end of my leash and began to lash at my breasts methodically dislodging the clothes pins with his blows. I cried out a few times with the pain.
When he had succeeded in removing all the clothes pins, he took each breast in his hands and squeezed forcefully.
“It’s not putting the clothes pins on that is painful; it’s when you remove them and the blood begins to flow back in,” he told me as I panted and groaned in agony.
When my breast torture was complete for the moment, I was laid back on the bed, legs bent and spread. Clothespins were attached to my pussy lips. Again this was entirely bearable and arousing for me, until he retrieved a roll of electrical tape from Jay. He wrapped this around each thigh and attached it to the clothes pins, pulling my pussy lips in a most wonderfully excruciating manner.
He also attempted to attach a clothes pin to my clit at which I cried out, “What the fuck?!”, and jumped unable to tolerate the pain level. I should have used my safe word at this point. I am surprised I was not reprimanded for not doing so.
Headmaster noted that I was very wet…so wet that he had trouble affixing the clothes pins to my pussy lips.
“When did you first become wet?” he probed.
Again I was shamed. . Shamed that I was so extremely wet, shamed that I was spread out there on the bed for he and Daddy to stare at just how wet I was, shamed to tell him I had first began to grow wet during our conversation in the lobby. After a little writhing around and stalling, I finally admitted to him when I began to grow wet.
He came to the side of the bed, my leash raised in his hand preparing to strike my inner thighs and/or pussy. I flinched, cried out and tensed.
He leaned down and said in a measured tone of voice again as if speaking to a child, “I haven’t even done anything yet. Quit anticipating it.”
I couldn’t help myself. I continued to writhe and whimper as he raised the leash again. He finally took pity on me and covered my eyes with his hands as he struck my inner thighs and pussy with the end of the leather leash.
I was rewarded with his cock in my mouth and his fingers moving on my clit. I sucked his cock to the best of my ability with my head in an awkward position, licking up and down the shaft until I reached his balls. Licking and sucking his balls until I was rewarded with “That’s a good girl.” My clit became more and more stimulated as his fingers worked it.
“Are you close to cumming?” he asked.
“Yes Sir,” I breathed.
“Don’t you do it. Don’t you cum without permission.”
I was pulled back up off the bed into position one as nipple clamps were retrieve from the bag and attached to my nipples with the chain connecting them threaded through the O ring in my collar, causing the clamps to bite into my nipples at first in a very arousing manner which would quickly become increasingly painful.
After a few moments I was directed to sit on the ottoman facing the chair and masturbate for him. I did this with abandon as my pussy was so wet and so very swollen. I took a furtive glance at Headmaster every now and then as he focused his attention on my hand and cunt which only served to increase my arousal.
When I was clearly close, again came the order, “Don’t you cum.”
I whimpered a bit and slowed my hand trying to stem the rising tide of pleasure threatening to wash over me.
“Don’t slow down either. Don’t you cum, but don’t slow down,” Headmaster ordered.
I took a couple of breaths which always helps me hold off cumming and did my best to comply.