Thursday, June 30, 2016

Playing With Mitch in the Dungeon

This naughty boy had to be severely punished! First he was suppose to text Aunt Jenn when he landed at the airport.  I checked his flight landed on you think I got a text from him? Then 2.5 hours after landing, he was suppose to meet me at my dungeon. Do you think this naughty boy was on time? Noooo.  His loss, not mine.
And don't you dare call me "Mistress Jenn" unless you want to see the sadist in me.  It is and always will be "Miss Jenn".  Just because I do some of my sessions in a dungeon does not give you the right to decide how to refer to me.  Do I make myself clear?

The pictures don't do it justice.  He's got a ton of welts everywhere, sadly you can't see them very well. I brought this masochist almost to the point of tears on multiple's rare to see the eyes of a masochist water and having him begging & pleading when he saw which implements I had chosen to punish him with. You can beg & plead all you want, but when my sadist side comes out to play...there's no stopping me!
I washed this naughty boys mouth out with soap & had him performing cleaning duties while wearing his parachute ball stretcher.
The big bad strap, this was my favorite!
And I do believe he's got his little sissy panties on inside out, what will I ever do with poor helpless Mitch?
I've got him strapped down to the spanking bench.  Both legs & arms. So very helpless & vulnerable...
I'm really regretting that I didn't take a photo of him all locked up in his cage.
This is one of the two spanking benches at the dungeon
The very effective
I loved the mirror here, as I get to watch Mitch's facial expressions while I spank him OTK
Such a beautiful red color. All bottoms should be pink, red, or black/blue.
Nice round butt, perfect for spanking :)

Since we were doing the Miss Jenn Experience, after the dungeon we headed out to dinner  & some bar hopping before his bedtime spanking.  I chose El Gaucho for dinner, since I enjoy fine dining and El Gaucho has just the right ambiance, especially coming straight from the dungeon.  Perfect lighting, paintings, and music.  Plus you can't beat the food.  Then we checked out a few bars, before heading to Mitch's accommodations for the night. Now although Mitch did get some fun spanks (OTK) & cuddles, the sadist in me was not letting the masochist in Mitch off easy.  I had him bend over the couch and some of the strikes with my paddle were so strong that I had his little sissy body flying into the back of the couch upon impact. Then ended with some soft sensual paddling, a bit of nipple pinching, and teasing....before locking this bad boy up into chastity. Something he had NOT been expecting!


  1. Oh my, this is the dream session. How luck this boy is. I want to make my way to that. Beautifull work miss jenn. Silvio

  2. Miss Jenn. I sit here, Sunday night - 4 nights after feeling all of your instruments. And, I can still feel those spanks. And I am still sore. I have never felt anything like this. And I loved it all. Well, there are moments that were sheer terror and pain and discipline - but being a masochist, looking back it is sheer pleasure. Thank you so much. You are such a delightful person to be with. I am humiliated by the panties being inside out. but, trying to put these back on after the first spanking, I wasn't thinking clearly. And, I am so sorry for being late and not texting as I said I would.
    That said, I can't wait to do this again. You surprised me many many times over the evening. I loved my time with you. The dreams I had following our evening - hmmm.... Thank you for your compassion and allowing me out of the chastity device before I flew home. I think I owe you something over the next couple of weeks for that compassion. You have a new fan. To any subs or boys needing discipline and considering seeing Miss Jenn. Do it. You will be so happy you did. A little sore for sure - but happy. Mitch

  3. I love his pretty red panties and the fact that you made the color of his bottom at least match that color if not more.