First Session

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To my own surprise and without real thought I quickly raised two fingers.

"Good," Mistress continued, "Regarding the second choice, I have already informed you that you will not come unless I allow it."

"I am inclined to allow it at this moment but will offer you the option."

She continued to explain that saying no would mean I would be released from my shackles, hood and clamps and that the session was over and that there would be no chance of release until the next time I would see Her again.

On the other hand, saying yes would mean that my left hand would be released form the chain and I would have to follow her instructions and that all other 'decorations' meaning the clamps attached to the hood would remain in place. She also warned me that it would be extremely painful to remove the clamps after an orgasm before She asked me to come to a decision.

Mistress Lynn gave me a few seconds to think it over and then said "what will it be slave?."

Again, two fingers went up quickly and Mistress appeared to be happy with my choice. Mistress stood up from her chair and unhooked my left hand. I dropped it to my side, waiting for Mistress' command.

"Good boy" She said.

"Now take your cock in your hand and start stroking, do it slowly."" I will tell you when you can speed up and when to stop, and when I tell you to stop, I want you to let go immediately," She said.

Meanwhile She had sat down again on the chair, lifted her legs and put her heels in my skin just above the nipples.

"You seemed to love them earlier so I am giving you a closer look, now when you feel you are about to come you may kiss one of my boots to ask for permission, but no coming before permission is granted." Mistress continued to instruct, while I had started to stroke my cock.

Left is not my preferred hand so it didn't take long for Mistress Lynn to tell me to speed it up and use longer strokes. I got some rhythm going and after a few vocal encouragements from Mistress Lynn accompanied by Her pressing Her stiletto heels in my chest I got to the point where I bowed my head forward to kiss Mistress' boots.

For a moment I had forgotten about the rope attached to the clamps and felt a shooting pain in my nipples again.

The moment I put my lips on Mistress' boot She said "STOP," and I had to let go of my cock. Mistress stood up and examined my cock dripping with pre cum.

"Way too early, you will need to learn control," She said, as She planted her knee forcefully in my crotch. She grabbed hold of my nipples squeezed them hard using her sharp nails and then attached the clamps again.

'Now let's try again," Mistress Lynn said but as I was moving my left hand to my cock, She gave another quick kick to the groin.

"Do NOT start before I tell you to." Mistress took her position in the chair and planted her heels on my chest again.

Like before Mistress would encourage me, sometimes vocally but mostly by just digging her heels deeper in my chest to be told to stop the moment I kiss Her boots.

This time at the end She kicked me in the balls twice.

We repeated this sequence three more times, then after the sixth cycle of frantic wanking encouraged by sharp stilettos digging in my skin, when I was ordered to stop after kissing Mistress Lynn's boot again, my cock started twitching when released.

Mistress instantly put the sole of one of her boots on the shaft of my cock and pressed it hard against my belly. Cum came out but it wasn't quite what I had hoped for.

"Now look what you have done," Mistress Lynn said sarcastivally.

She stood up and unlocked the remaining cuffs, removed the hood and gag and also removed the clamps from my nipples, which sent an enormous jolt of pain through my nipples as the blood rushed back in.

She teasingly pinched both nipples with her sharp nails and told me to get on my hands and knees again.

She got a new piece of rope, tied that around my balls and then tied it to a hook in the floor. Mistress Lynn picked up the chair and moved it back a little, then sat down and presented the cum covered boot.

"Time to clean slave, every time I will allow you to come it means that you will also have to eat your own cum."

"After all I have no use for it." She added.

"You will get used to it as you will to MY drink, which I will have for you when I allow you to drink."

Then She tapped the boot with her riding crop to indicate I could start, but as She was just out of reach it meant I had to pull on the rope to reach her boots adding more pain to my already sore balls. Mistress Lynn laughed at my struggle and sat back to watch me work.

When She was satisfied Mistress Lynn ordered me to stop. She handed me a bottle of water and also told me it would be the last time She would offer me 'normal' water.

Then She untied my balls and told me to follow her.

We went back to the throne where we had started. Mistress sat down and I kneeled before it. She put her heels on the top of my thighs.

"For your first visit you did really well slave but there is still a lot of progress to be made," She started to evaluate.

"I would like to see you again next week when we can continue your training."

"Until then I want you to focus on the things you have learned today."

She then stood up picked up a small box and said "It is almost time to open the locker and let you get dressed but I have a small present for you first."

She then told me to stand up and put my hands behind my back. She opened the box and took out a metal item which She quickly placed around my cock and then locked.

For a moment Mistress Lynn showed me the key with an evil grin and said "I'll keep this safe here."

She then told me to get my clothes and get dressed.

Once I was dressed, she was waiting for me in the hallway, Mistress Lynn gave me a kiss on the cheek and a hug and walked me to the door. She let me open the door said "Good boy, see you next week" and let me go.

With a head full of new impressions and lessons and a sore body I went home.

To be continued?

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4 Comments
LeoLewinskyLeoLewinskyover 1 year ago

Very nice story, but missing a detailed description of the use of a locking collar. And to the end, its getting a bit sour by the placing of a chastitycage. For my opinion chastitycages, blackmailing, sissyfication, gay actions and cuckolding are used too often by most authors and therefore quite boring in the meantime. Your style is very good and I would like to read more from you, perhaps without the points above!?*hope*

AnonymousAnonymousover 1 year ago

Yes, please continue! Can't wait for more

FailedscoutFailedscoutover 1 year ago

In interesting take and a good start.

Thank you for writing and posting here.

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