My First Session With My Mistress
This is unfortunately, only a fantasy. If anyone wants to make it a reality, let me know
We had met on the internet, and we had spoken a number of times, but when Mistress told me She was going to visit NYC and would be available for a live session, I was excited and, I admit, a bit nervous. After all, live IS different from internet and phone. I was torn between physical fear, fear that I would disappoint my Mistress, and fear that the session would not meet my expectations.
Mistress told me a week in advance that she would be staying at the Plaza. I was already trained not to cum without her permission, but for this week I was given an additional instruction. I was not permitted to have an erection. Should I have an erection, I was to record the time, place and circumstances and the length of time of the erection. During the erection, and when waking up and before going to sleep I was to repeat "My cock and balls belong to my Mistress."
The week went quickly. The next thing I knew I was dressed in a suit and tie, outside my Mistress' room. Before I could knock on her door, I had to follow her instructions. I unzipped my pants and removed my cock and balls, so they hung out of my pants. I waited until the hallway was clear, but I was afraid that, at any time, someone would step out of their room and see me exposing myself. I could not wait long, as Mistress had given me a time to knock, and I did not dare to be late. Finally the time came and I knocked.
Mistress took a full minute to open the door, possibly the longest minute of my life. Finally, the door opened and I walked in, careful to keep my eyes down, as Mistress had ordered. Mistress immediately started to toy with my cock and balls, I'm sorry, I mean her cock and balls. That is what she kept asking me as she slapped my cock and squeezed my balls. "Who owns this cock?" she asked as she slapped it three times. "You do, Mistress" I answered. "And who owns these balls?" she asked as she squeezed them hard. "You do, Mistress" I panted through my tears.
"First thing, your safe word. If you want me to stop, just say "I want to go home" If You say that, I'll stop, let you get dressed and send you home. If you are staying, I want you to strip and get on your knees."
So I stripped quickly and got on my knees. Mistress quickly put a blindfold over my eyes. I could not see a thing. Mistress then pulled me by my nose while on my knees. I felt the carpet stop and I felt tile under my knees. This must be the bathroom. Mistress sat me down on what must have been the toilet. "Piss for me, my pet, Piss for me." I had never pissed before a woman before, but Mistress had ordered me to come prepared to piss so I really had to go. Finally, I was finished and Mistress told me I was a good boy. Mistress placed me on my knees in front of the toilet and ordered me to lick her shoes. I could not see, but I heard her piss hitting the bowl. When she finished, she put Toilet paper in my hand and guided it to her slit. "I want to feel the love as you wipe my piss. I want you to show me that serving me is the most important thing in your life."
So I carefully and gently wiped my Mistress' pussy. I was blindfolded, I could not see it, but I did the best that I could to wipe My Mistress, to clean her pussy from her piss. When I was through, I was about to throw the paper in the toilet to be flushed down, when Mistress stopped me. "Eat it" she commanded. "Be a good boy and eat it." So I ate the piss laden toilet paper.
Mistress then grabbed me again by my nose and pulled me out of the bathroom. She guided me over her knees and started to spank my ass. "This is for my pleasure and amusement. later I will punish you. With that she proceeded to spank my ass hard, occasionally taking a break to squeeze my balls.
Mistress must have spanked my ass around 50 times before she stopped. "That was your first spanking, and I have a present for you, your first collar." She put a leather collar around my neck and I was thrilled to feel it snug as Mistress fastened it. "I enjoyed giving you the spanking, but I am disappointed in you. I did not give you permission to have an erection, and yet, here you are, erect in my presence. This is an insult to me, and you must be punished." Yes, being spanked while laying across Mistress' lap, feeling her thighs surrounding my cock while she spanked me, gave me an erection. "Your problem is that you still think of them as YOUR cock and balls. They do not belong to you, they belong to me," she said softly as she squeezed my balls harshly, until my, sorry, her cock was once again soft. "How many erections did you have during the week? "Twelve, one every morning as I awoke and there were five nights that I felt erect before bed."
"And you did nothing to control your misuse of my property. I will punish you harshly. When you allow my cock to become erect without my permission, it is as if you are stealing my property. Do you agree to accept my punishment?"
"Of course, Mistress, I beg you to punish me harshly, as I deserve."
"I will punish you most painfully, and yet I cannot have you yelling, this is, after all, an exclusive hotel. I am going to place a gag in your mouth to muffle your screams. But I will not fasten the gag, so if you wish, you may spit it out and use your safe word. Do you understand?"
"Yes Mistress" "Would you like to go home?" "No, Mistress, I want you to punish me harshly as I deserve."
With that Mistress pulled me to my feet by my brand new collar. She put cuffs on my wrists and bound them behind my back. She pushed a gag into my mouth and I prepared myself for a whipping. But Mistress had something else in mind. "Who owns these balls?" asked Mistress as she rolled them in the palm of her hand. "You do Mistress" "You're damn right I do," laughed Mistress, as she put a clothespin on the sack. Oh, the indescribable agony. And then another, another and another. Eventually, 6 clothespins on my sac. She pulled on each one, testing each one to make sure it was tight. "Those balls are mine, and don't you ever forget it." Through the gag and through the tears I was able to mumble "Yes Mistress." Then she rolled my cock in her hand and again she said, very softly, "This cock belongs to me, doesn't it" I was so scared, I knew what was coming, but I mumbled "Yes Mistress" and immediately felt the clothespin pinching my shaft. If not for the gag, I would have howled, loudly. I thought of spitting it out and going home, but I wanted to please Mistress, so I determined to endure. So I did. Six clothespins on the length of my cock. My cock was flacid, so three were on the front and three were on the back. I was crying, tears streaming down my face, my nose was running, I was moaning behind the gag. Finally all six were on. It was over, or so I thought. "Those were for the erections you had during the week. One more for the erection that you had while I was spanking you." Mistress took my cock and placed one more clothespin on the head around the peehole. I fell to the floor. I rolled in agony., I thought I was going to throw up. I thought I was going to pass out, I don't know what I thought. This was pure pain. Hell could not be more painful. Finally I heard Mistress say, "Good boy, your punishment is over," and she reached down and began to remove the clothespins.
"Rest for a little, you have taken your punishment like a good little boy. You will be rewarded." I heard her leave and come back. I felt her drying my tears, and helping me blow my nose. "Remember, my little boy, I own all of you." Eventually, the pain grew less, almost tolerable. "You have pleased me and amused me. I am going to permit you to pleasure my body" She helped me to lie on the bed and removed the gag. Mistress instructed me to keep my tongue out. I expected to feel her pussy lips across my mouth, but I quickly realized that Mistress was not giving me her pussy to suck, but her ass. "Let me feel your love," she said. Let me feel your love for me as you tongue my ass, as you worship my ass."
I had no choice. Mistress sat on my mouth with her full weight. I licked her ass as gently as I could. "Tongue fuck me" she ordered. I did my best to insert my tongue in and out of her back door, I could smell and taste the fecal matter that is always present in any ass, no matter how clean. I could not let that bother me. I was just here to please my Mistress.
At long last, I could feel Mistress scrunch back. Her ass was now over my nose, her pussy was over my mouth. "I want you to use all your imagination, all your skills and talents, to give me an earth moving orgasm. I am giving you permission to become erect, and if you please me, I may give you permission to cum."
With that, I began to lick Mistress' slit very gently, while Mistress leaned over and gently started playing with her cock. She treated it with special tenderness, she placed some kind of soothing lotion on her hands as she stroked her cock slowly and tenderly. I was licking all around her slit, around her lips, tasting her growing wetness. My cock quickly grew hard. Mistress gradually increased the pace and firmness of her stroking. It was as if she was in my head. I, too, began to increase the firmness of my tongue. I began to suck her juices as they started to flow. I began to tease her clit, touching it briefly and gently. Mistress warned me again that I may not cum without permission. She was stroking me fast and hard. I sucked her clit into my mouth and flicked it with my tongue. I could hear her moans of pleasure as Mistress rocked her pussy on my face. 'Yesss, Yesss, Keep going, keep going.." she screamed as she rocked on my face. "You can cum when I reach 10 Mistress yelled as I continued to push my tongue against her clit as I sucked it and drank her juices.
"Six, Seven Eight" she screamed as I could feel her cum and I anxiously awaited the ten count. But Mistress let go of her cock and stopped counting. “Ohh OHH OHH that was good that was good that was verry good” Mistress was moaning as she came. My cock, sorry, her cock was twitching in the wind. I was one stroke away from cuming, but Mistress would not give me that one stroke.
My balls felt swollen, I wanted to cum. I started to beg "Mistress, please, I beg you, let your good little boy cum. I'll do anything, anything at all, Please, let me cum." Then I heard something that shrunk my cock immediately. A male voice. "Any trouble Honey?" Mistress responded "No trouble, loverboy, this littleboy wants me to let him cum, but I don't think he deserves it. Should I give him another chance?"
“I heard him mumbling something about doing anything, why not put him to the test?" "Loverboy, you're a softie. OK, I'll give him a chance." "Honey, did you call me a softie? You'll regret that."
Mistress lay me on my back and placed her ass on my mouth. "Last chance little boy, lick and suck for all your worth." As I licked my Mistress's ass, and tongue fucked her, I heard and felt her lover fucking her. Mistress was moaning. "You fill me, you feel sooo good. There is no one like you.” I felt his balls banging against my chin as I concentrated on licking my Mistress' ass. I felt him pumping faster and faster. Mistress was moaning louder and loader. Finally, they both exploded, very loudly.
"Little boy, clean my pussy NOW! suck me out. Swallow my lover’s sperm and my juices. QUICKLY!" To suck out another man's cum from my Mistress' pussy was something I never envisioned. I am not gay, never considered it. This did not feel right. But I wanted above all else to please my Mistress. So when Mistress lifted herself from having her ass on my mouth to placing her dripping pussy on my mouth, I drank her eagerly. Her juices were tasty, but the taste of male sperm was strange. Never the less I did not hesitate. I licked and sucked and swallowed. Gradually, I finished swallowing the sperm and found myself with a growing stream of my Mistress' juices.
Suddenly I felt Mistress reach once again to play with her cock. "Let me feel the love. Let me feel that you live to give me pleasure." And I did. I wanted to give my Mistress pleasure, whether or not she would allow me to cum. So I took my cues from her movements and teased her, slowly and sensually. Mistress was stroking her cock slowly but firmly. I was becoming harder and harder. I could feel Mistress growing hotter and wetter. I could hear her moan as I gradually increased the pressure on her clit. Mistress started to yell at me "harder, faster" but I waited, still teasing her. Mistress started to stroke her cock faster and faster. Finally I went after her clit with growing passion. "Cum when I count to ten" And she started to cum. My cock was aching but I concentrated on bringing My Mistress to her climax. As Mistress counted, she was rocking harder and harder against my face. "TEN" she shouted and I spurted long and hard. This was the best climax of my life. I was totally drained.
Mistress was rocking and moaning in the aftershocks of what I felt was a mighty climax. Finally, we both recuperated.
"Loverboy, help my slave get dressed, then we can shower"
I was still blindfolded as I was dressed. My collar was still around my neck and I was guided to the door. In a second, before I could do a thing, my blindfold was removed and I was literally kicked out the door. The door closed quickly behind me. I had a session that I would never forget, pain that was unbearable followed by a climax that was stronger than any I had in my life. But as I went to the elevator, taking off the collar, a precious gift from my Mistress, I realized that while I had been with her, I still had not seen her. I could pass her in the street and not recognize her. I had no idea of what she looked like.
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