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I recently had the pleasure of a weekend filled with guided masturbation backed by the thrill and excitement of light humiliation.
We started the weekend off with a little trip to the local sex shop, my sweet stroker boy who is straight and not a hint of gay or bisexual was sent on a mission and the purpose behind it was to make him uncomfortable and slightly humiliated. I instructed him to remove his undies and to place a cock collar around my dick before walking into the store. I made him approach the butt plugs and pick each and everyone up and check them out naming them and describing them for me, not only was he embarrassed and humiliated he was turned on and excited and had a semi erection growing in his pants. I had no intention of making him buy one of those butt plugs I just wanted others to see him exploring them on the shelf!
I then made him go browse the dirty magazines and movies looking at shemale porn and gay magazines, again he is not gay in any way but it was all about humiliating him in public…taking that chance of someone thinking he was a dirty boy and liked that type of porn. As he browsed their selection he had to read the titles out loud to me so anyone within earshot not only heard him reading them to me but also calling me Mistress.
After a few careful selections for purchase sending him to the sales clerk to pay proved to be very exciting for this horny humiliated  stroker slut because the lady behind the counter suggested cock related items to him to go with his purchases, the nervous laughter I heard from him was well worth all the effort in sending him there. As a result of his exchange with the young lady he went out to his car with a raging hard on and left with the instructions to edge his cock on the way home, and then be naked and collared for me on web cam as soon as he walked in the house.
The rest of the evening was spent with him enjoying some drinks and being naked for me on web cam as I went about my usual routine, this part was especially hot for him because he kept imagining that this is just how it would be if he were here naked and collared for me while I was working. Patiently waiting to please me in any way he could and willing to do anything for me. I would give him tasks to do while I was busy like going into our adult chat room and admitting things he normally wouldn’t or exploring enchantrix empire and commenting on things nobody would even dream he had any interest in.
We ended the night with one of the best two mistress phone sex sessions I have ever had, involving him exposing himself to another lady, his day and how he ended up on the phone with the two of us and all the many things I had him do for me, watching his cock grow harder with every instance of humiliation and the fact he was telling another lady who thought he was such a nice sweet guy made it even hotter. He was granted an orgasm only after promising to do one of the things for us he never thought he would tasting his own cum and he followed through with a bit of teasing and light humiliation from us about it.
This was just the beginning of the weekend for my horny stroker boy and the next day proved to be a bit more humiliating and exciting for him than the first…..but that is a blog for another time hehehehe I am more than happy to share with you all just what happened the next day that worked him into a horny frenzy, but you’re going to have to do your own phone sex session with me for those details :wink wink:
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Oh wow!! What a great day for this gentleman. I can only imagine the excitment and trepidation and anticipation as he shopped in the adult store, then to top it off with a two Mistress call must have been spectacular. Great Blog Post!!!
Well thank you gummy he did seem to have a great time. He was nervous and excited and horny the whole time and making his shop for humiliating things was just perfect….and yes the two mistress call to end the night was fantastic just love exposing and sharing strokers and slut with other ladies!
Thank you for an amazing weekend, Constance. The way you had me go into the Adult Sex Store and browse the butt plugs, before having me purchase the super sized bottle of climax lube was so humiliating and arousing. Having a sexy Phone Sex Mistress guide my masturbation for the weekend was awesome!
You proved to be a very good boy that weekend for me doing everything I asked no matter how humiliating it was. I had so much fun guiding your masturbation weekend and spending so much time arousing you and keeping you horny and on the edge for me!
He was lucky to be able to spend so much time with you 🙂
Yes and he appreciated it………I still was here for everyone as well my stroker slut just waited patinetly like a good boy should
What a lucky guy to hang out with you for so long and get humilated. What’s a guy have to do to get that lucky. Ms Constance, I enjoyed your show tonight and I will make sure I vote for you for most creative. We can pull the upset and beat Ms Ally. Haven’t been to too many of your shows but that will all change. I had such a great time tonight and once again, thanks for being in the penny auction.
Kurt
Hi there Kurt and thanks for the comment to answer your question what does a guy have to do to be so lucky……….well hehehehehehe be a good boy to me help me in anything I need and do whatever it takes to make my day better this is what that guy did and has been doing for 2 years and I am willing to go out of my way to make his stroker humiliation dreams come true 🙂 Thank you kurt for being at my show I loved having you there and hope you do join more they are fun and silly and sexy all wrapped into one LOL and it is my pleasure to be in the penny auction I am soooooo looking forward to the auction itself
i would love to be put in this situation by Ms Constance. i would love to be humiliated in this fashion. being humiliated by a beautiful woman like Ms Constance is something i think about all the time. i know im a failure as a real man, so being a obedient sissy slut is something i want to be able to be for a woman like Ms Constance.
I bet you would britney humiliation has always been part of what you love so much being a sissy slut. I adore you sweetie and you being my obedient sissy slut sounds wonderful!
Just spent a little time tonight remembering this awesome weekend. I’ll never forget it 🙂 Thank you for this memory, Ms.Constance.
awww sweet boy it was my pleasure!!!