It has been a while since I last wrote to you, my dear readers. I have had a lot of memorable sessions, but this time I want to tell you about a truly remarkable overnight session some time ago.

Timewaster or not?

He was a new potential sub who was eager to bombard me with e-mails. At first I was a little sceptic, if he would eventually prove to be just a timewaster, but as I got used to the way he wrote his e-mails and figured how to slip inside his head, discovered his kinks and made sure that he could not go an hour without thinking of me, I knew I had potentially something really magical wrapped around my little finger.

Usually at the beginning sub men have strict lists of do’s and don’ts, but as they become more and more obsessed about their Mistress, the lines become blurred in a lovely way. The do’s may become less important and the don’ts may become more tempting. What is left is a different, a more selfless, kind of submission, which is a sign of confidence to a Domme. And don’t be scared of me, I will respect your hard limits, be scared of yourself, for you may become so obsessed that you will loose your own limits.

This was the case with this sub as well. I didn’t have to put a lot of effort to persuade him to lock himself in chastity and send me the keys, and just five days later I had his signature in a contract that gave me a carte blanche for our overnight session, but also I knew about his main kinks: humiliation, chastity, cuckolding and his addiction for lesbian porn. What a naughty boy… I didn’t need to rack my brains in order to arrange a session of a lifetime, not just for him, but everyone involved. After he had sent me the confirmation for our hotel booking, I made a few phone calls to my trusted kinky collaborators, I had the basic building blocks for the session in order.

I’ve arrived

Once he sent me a message that he had arrived at the hotel, I told him that I would be arriving shortly, and ordered him to be waiting for me outside the hotel. Once in the room I made necessary checks that he indeed was wearing the chastity cage and naturally I didn’t miss the opportunity to tease him before our dinner at the restaurant downstairs. I played with him a bit just for fun. I told him first to strip naked, I grabbed his chastity and shook it. Then I moved my body closer to him, I grabbed the back of his head with my other hand, bit his ear and whispered: “such a small penis needs to be locked permanently”. This sent shockwaves through his whole body, and I could hear how he was desperately trying to swallow something resembling of an unpeeled egg. His nervousness made me laugh spontaneously.

Make me some tea

I slapped his cheek gently and told him to help me with my beloved trenchcoat. Then I told him to kneel like a good doggy as I sat in the armchair to relax. I commanded him to brew me a nice cup of high quality Japanese sencha green tea before unpacking my luggage. I saw his face switch between fear and excitement when he took my black lingerie and sex toys from my bag. Once he had organized everything neatly in the wardrobe, on the bed and the table, I told him to crawl over and be my leg rest, while I enjoyed my sencha. A naked sub on all fours underneath my feet. I pushed his head with my other foot, while I demanded him to hold position.

I placed my toes on his lips and told him to kiss them, while I slided my other foot along his arched back and down his ass until my toes found his testicles. At first I played with his balls gently, and I noticed how his chastity cage was getting nice and tight and he got so distracted that he stopped kissing my toes. What a perfect reason to give him a little reminder, that a sub should never forget the tasks given to him by his Domme. So I removed my foot from his groin and said: “I don’t remember giving you permission to stop kissing my toes!”, and then I kicked his balls. He let a groan from his mouth but proceeded worshiping my toes immediately.

Why are you leaking?

After I was done with my sencha, I stood up and grabbed his chastity. I noticed he was already leaking. “What is this tiny piece of skin and why is it leaking?” “Do you pathetic small dick loser really think that you have any chance with a stunning woman like me?” “You wouldn’t even know how to satisfy me, I need a real man with a proper big dick, not just a skinny worm like this!”, and then I grabbed his balls with force and gave them a few slaps. I walked to the bed and grabbed my favourite strap-on dildo. I told him to get up and I placed the strap-on next to his chastity. “Can you see the difference? If you had a nice big dick like this, you could stand a chance, but with a small dick like that…

Do you think I would ever bother, you wouldn’t even last a minute with me?” Then I placed the dildo on his lips and told him to open wide. “But it doesn’t mean that you can’t serve me. Show Mistress how good you are at sucking dick!”, I told him and laughed as he started deepthroating the dildo passionately. I helped him a bit and pushed it deeper and made him gag.

His eyes were watery due to gagging on the dildo several times. I told him to get washed quickly and then dress up for the dinner.

Shall we go to the restaurant?

I checked myself in the mirror, and let my hands wander first over my breasts and I adjusted my bra a little, and then let my fingers slide over my luscious curves and pure white skirt. I smirked at myself, perfect mood for some naughty mischief. My sub stepped out of the shower and I told him to hurry up. It’s never a good thing to make your Mistress wait for you. He looked hilariously clumsy as he was trying to dry himself with a towel while getting dressed. In the elevator I looked at him via a mirror, used my curvy butt to squeeze him against the wall and rubbed myself against him, slowly and sensuously, while maintaining eye contact with him in the mirror. I could see excitement, submission and anguish in his eyes as he was getting a rare treatment from an elegant Mistress. The elevator reached the ground floor, I winked at him and gave him a blow kiss via the mirror.

We reached the restaurant and were directed to our table. After we had made the order, I excused myself and went to refresh myself. Or to be honest, I went to the toilet to remove my panties. I made sure they had my scent and went back to the table. I handed to panties over to him and told him to sniff them properly before placing them in his breast pocket. He felt embarrassed to do that in a full restaurant, but I did not give him an option, and he obeyed. He clearly liked the idea of doing something like that in public, but I don’t think anybody even noticed it. But the important thing is the fear of being caught in the act in public.

 

 

to be continued ……… part (1/3)