The most unusual / unexpected thing your KH has ever done to you

Discussion in 'Chastity and orgasm denial' started by Dfberns, May 25, 2019.

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  1. Dfberns
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    Dfberns Living the dream, one day at a time

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    In the same vein as the thread "Hot things your KH have said to you" I would like to know The most unusual / unexpected thing your KH has done to you. For me it happened last night:

    We were in bed and Princess Di had been teasing my nipples in our ongoing experiment to see if I can have an orgasm through nipple stimulation alone. As of last night, I have been very close, but no success as of yet.

    But the most unusual thing happened later, as I was worshiping her with oral attentions. I noticed that the more I worshiped, the more relaxed she became. Before long she was sound asleep.

    Needless to say this was my most unusual / unexpected moment...

    With nothing else to do, I cuddled up to her and drifted off to slumber-land myself.

    Let's hear your most unexpected / unusual experiences.
     
  2. Mash2214
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    Mash2214 Locked today, tomorrow, forever

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    I’ll need to think about that for awhile. My wife is Very Vanilla.

    Just kidding
     
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  3. Miffy
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    Miffy Long term member

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    It would have to be when she totally out of the blue took me with her large strapon on her birthday
     
  4. Susanstoy91
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    Susanstoy91 Long term member

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    A few weeks ago, during a T&D session I was tied to the bed. It had been 30 minutes into the session and I was on the edge, but still locked in my cage. My Wife(KH) was licking and rubbing my balls and driving me crazy. She starts to rub her finger up & down between the bottom of my ball sac and my anus. This over the years has driven me nuts, but didn't happen very often. She just brushed over my anus very lightly with her finger. Then she slowly started to finger me. Not a full prostate milking, but just slowly in and out...This went on for about ten minutes. I wanted to cum and was so close...Then, like many other sessions, she just got up and left the room. Leaving me there to think about what had just happened. Not sure when or if this will happening ...again, but from my reaction, I hope she saw how much It drove me crazy...Maybe not "unusual" but very "unexpected"...:lockkey:
     
  5. Doug Scibor
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    Doug Scibor Long term member

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    I hope your praised her efforts and thanked her... from your knees.
     
  6. PouchPantyLover
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    PouchPantyLover Long term member

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    This turned out to be not at all unusual, but certainly the most unexpected. I am required to inform her of my schedule each day and keep her updated with text messages. I checked back in with her as I was returning into our section of town and she responded by texting me "meet me at nail salon by Times. We have an appointment to get a pedicure together".

    Many people on here are probably like yeah and? There are several things you need to understand why this qualifies as unexpected. First off I was under the impression only women got pedicures. Secondly I was under the impression pedicures were synonymous with getting your nails painted. Thirdly my wife playfully utilizes my crossdressing fetish, but she is very private about it and is highly concerned about public exposure. She had teased me about doing something like this in the past, but always in remote locations where it was unlikely anyone we knew would see us. The place she picked was smack dab in the middle of the busiest part of our home town with big glass windows facing the main thoroughfare. It was virtually impossible that someone we know wouldn't see us.

    So I had 30 minutes to kill before that appointment and it was filled with such nervousness, anxiety and excitement. I never in a million years would have predicted this. So the most unexpected thing she has done. The actual event was not as good as the shock and anticipation, but it was still a lot of fun. Hopefully next time she picks a color coat for me instead of a clear.
     
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  7. tomf_22033
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    tomf_22033 Long term member

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    Congrats
    I hope you enjoyed it
    For some of us Strapon sex isn’t unusual anymore. Maybe if you’re lucky you’ll become one of us
     
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  8. Tom Allen
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    Tom Allen Member

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    Unexpected: having been locked for three or four straight months, I thought Mrs Edge would unlock me for my birthday.

    Nope.

    Hmm, maybe she was waiting for the weekend.

    Nope.

    Oh, she's waiting for our anniversary at the end of the month.

    Nope.

    Once we passed those milestones, I knew it was going to be a very long ride.

    Honestly, not being unlocked for my birthday was the hottest, although not being unlocked at the 1 year mark was a close second.
     
  9. Penney
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    Penney Long term member

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    My wife has surprised me many times. The first one that comes to mind, seems so tame now, but at the time was a giant surprise.

    We had played with my pantie wearing off and on, but nothing more then for play times; my wife also knew I had a bit of a pantie fetish.

    About twenty years ago, before one of my business trips to Europe my wife was helping me pack as she usually did. For this trip she counted out the days and the guy underwear--one pair for each day, several weeks worth. I can still remember, as she kissed me good bye, she said that I was to throw away the pair of guy underwear that I had on at the end of each day. It would lighten my suitcase, she added, which was always an issue coming home since I had usually purchased presents to bring home. So by the end of the trip I'd be out of underwear--but coming home. Each night, as I was told to do, I discreetly disposed of my men's underwear.

    The day before I was to return home, I was in Florence and out of underwear. We talked on the phone about my flight home, and that I had no more underwear and that she had miss counted. Nope, she said, I was to go and buy some new women's panties for myself.

    Near to were I was staying I had passed a women's clothing store. When I went back I found that they had a large selection of panties, and also, lucky for me, a great sale on the panties. I bought six pair. I can still remember the nervousness I felt taking them to the counter and paying for them. This turned out to be the first of many pantie purchases overseas. I wore a pair of those panties on the plane home.

    The real surprise, however, was that unknown to me at the time, while I was gone she had thrown out all of my male underwear--everything! My underwear drawer was empty, but not for long.

    From then on I was only to wear panties.

    I've asked her where the idea for throwing out my underwear came from. She was rather coy, but said it seemed more appropriate to my new role, and that she liked my demeanor better when I was in panties.
     
  10. Nicoftime
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    Nicoftime The suspense is terrible...I hope it lasts

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    For me it wasn’t so much what she did, but what she said she liked and wanted.

    We tend to send dirty pics and memes to each other during the day, and hers started being about maid service. When we started all this maid stuff was a hard limit for me. I asked her if it was something she wanted, she said yes but knew it was one of my limits. I told her I was would try.

    I did the works, outfit and all, served, bathed, and massaged her. Later I pleased her orally and with fingers. I stayed locked and I rubbed her feet while we watched tv and we went to bed. I asked her the next day if that was something she wanted me to continue, her reply was yes. Over a year later we were playing a truth or dare game and one of the questions was “what was the hottest erotic experience you’ve ever had”. Her reply shocked me a bit when she said it was when you first were my maid.

    For the most part I thought her asking me to do that was mostly her wanting to incorporate my hidden feminine nature into our FLR, now I know that the experience excites her.

    I myself have some gender issues so am not opposed to it, but I did and do feel a bit silly in a full maid uniform. I’ve since given up on that and just dress femininely instead.

    The hottest thing for me that she’s ever done that was a bit unexpected was to inform me that the only time I will be out of my cage for the rest of my life, will be for the few minutes of fun she thinks I’ve earned.
     
  11. Doczilla421
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    Doczilla421 Long term member

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    She made it permanent. I thought that she would release me after a day or two... nope. That was a little more than a year in a half ago. She only allows it off to inspect it and during that time I'm restrained to the wall with chains and handcuffed, or spread eagle on the bed. That's the only time its removed and that's less than 5 minutes.
     
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  12. Frolicking
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    Frolicking These need attention too

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    In her opinion I had been clearly been pestering my wife, so suddenly she had enough and dragged me to a nearby tree where she nailed my nipple to it and left me there .
     

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  13. Penney
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    Penney Long term member

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    When I first read your reply I was shocked, but then realized your nipple was already pierced. I'm glad that you were not injured. So perhaps her treatment was appropriate for you. How long were were you left nailed there?

    BTW: What a great picture.
     
  14. Frolicking
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    Frolicking These need attention too

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    Thank heavens I was already pierced, else I would have .....
    She did not leave me that long. Something like an hour in the sun and then she really had trouble getting that nail out. However it was an unexpected expierience.
     
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  15. Penney
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    Penney Long term member

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    Oh my, I'd say unexpected! I can only imagine the image of her trying to work that nail free. I've wanted to have my nipples pierced, but Mistress has said no way.
     
  16. Cumwhenallowed
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    Hello all my first post, hope you don't mind if I join in. Docllia421 I know just how that feels, a previous mistress had me locked for 3 years. Like you I was only ever unlocked while restrained, I didn't touch my bear penis for the whole 3 years, she or her sissy hubby washed it only ever ejaculated while in the cage.
     
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  17. KittensProperty
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    KittensProperty Kitten's Happy Property

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    A night at the Friends Club when she and a woman we met that night put me in a sex sling. After a short teasing from them both, their attention turned to each other as i watched. Even more surprising was when i was turned to see the room across the hall while both of them joined the man in playing with his wife who was bound standing spread eagle.
     
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  18. Frolicking
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    Frolicking These need attention too

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    At least it makes your position cristal clear.
     
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  19. Dfberns
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    Dfberns Living the dream, one day at a time

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    Thank you all for sharing your experiences. I have enjoyed reading them and look forward to hear many more stories.
     
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  20. Blue Buoy
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    Blue Buoy She’s sea of undetermined depth and power

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    Something unexpected my KH did occurred when she and I first began exploring orgasm control training, and talking about cuckolding, and chastity. We were done having children and my wife suggested strongly that I get a vasectomy. She gave me the name of a female urologist that she thought would be good for me. I completely agreed with her, it made sense, but it was also a little humiliating. My wife accompanied me to get the procedure done. It was a quick procedure, a little numbing cream, a sharp scalpel and a few stitches. Shortly after that we began cuckolding and chastity and she loved it! She had complete freedom and before long she was playing with a couple of regulars with big cocks and from time to time a new guy that would strike her fancy in a particular way. She always played with these men alone. With some she would use birth control and for others not at all. It was beautiful to witness her decision making process, it spun me like a top! I often fantasize that the sequence of these events was more than a coincidence, that she had planned this from the beginning, to make me the submissive, sterile, pussy boi cuck I am today. I feel super lucky to be basking in the glow of such a radiantly horny wife that cares for me.
     
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  21. Elephantdonkey
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    Elephantdonkey Active member

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    Better look out for the squirrels I hear they like nuts! Lol!
     
  22. Penney
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    Penney Long term member

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    My wife has planned some fun unexpected experiences for me. This happened some years after I was first put in panties.

    Every year we would get away for a long weekend on our birthdays or anniversary. We would take turns planning it. This particular year my wife was in charge of the plans. She had laid out what I would wear in the morning we left. So after my shower I found a pair of shorts, a Victoria Secret black thong, and a t-shirt. I was rarely asked to wear a thong unless she had some fun play in mind, so I'm thinking this is looking good.

    She directed me were to drive as we headed out of town. An hour or so later we are in the downtown of a near-by town. She is reading the directions she had written down. I'm told to pull into a parking space, and I wondering what's this-no hotels in this part of town. I have no idea were we are going. Not for you to worry, she said, I was to just follow her. I did, right into a nearby tattoo shop.

    Once inside she and the artist discussed her design, like old friends. Clearly this had all been all planned by my wife. Later I learned that she had done quite a bit of research on the artist, and they had chatted over the phone. We were lead into a back room. I was told to take off my shorts and lay on the padded table. Now I realized why I was in a thong!

    I also knew by now "her" tattoo was going on my ass. This would be my first tattoo. The tattoo artist went to work, and over the next hour or so I was tattooed with the design she had decided on. I now have her rat forever on my bottom.

    Later that same night at the hotel, she took me for the first time with a strap-on, as she enjoyed a view of her new rat.
     
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  23. SubSnuggler
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    SubSnuggler Owned by Mistress2and4you

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    • making a whole body waxing appointment with a female practitioner and then making the appointment recurring
    • telling a female employee of hers putting a cup in the sink, 'don't bother to wash that, he's the only one that does the dishes around here' and pointing to a sheepish me
    • having me put on a slave anklet and refusing permission to ever take it off. I've had it for a couple of years now...
    • we have a huge shower and we almost always shower together. I'm always tasked with washing her head to toe while she stands there. One day as I'm on my knees soaping her thighs down she takes on a wide stance and tells me to clean her ass with my tongue
    • the first time she took me with a strap on...
    • and right behind that the time she made me ride cowgirl for what seemed like hours until I finally gave myself a sissygasm
    • taking me to an adult store and having me buy her a huge dildo while she browsed around
    • making me kneel naked in front of (fully clothed) her for a foot worship session. I had to lick her feet, while masturbating. She told me to ejaculate on her outstretched calf and then told me to clean her up with my tongue.
    • the first time she bent me bare-assed over the footboard and punishment spanked (flogged lol) me with my own leather belt, then admired the marks for the next few days
    • the first time she wore my key around her neck in public (she still wears it constantly)
    • the first time she told me she wanted to sit and watch me give a man oral pleasure (she's never forced me to do it though)
    She does a lot of other little stuff, like in public or private she puts her hand around the back of my head and grabs my hair and forcefully kisses me. To vanilla folks it looks like a passionate, loving kiss; to kinky folks perhaps more...

    All this stuff is probably pretty tame to most people here but pretty kinky to us.
     
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  24. tecolote
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    tecolote Long term member

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    I did not expect her to play the chastity game at all. I expected her to refuse flatly. I only even told her because I needed something else. It was kind of a hail Mary that I didn't expect would work even if she agreed to be the Keyholder. And now, very slowly, she surprises me more by starting to tease me just a little.

    It's not much compared to the things some people do, but it's perfect for me for now.
     
  25. johnjames55
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    johnjames55 Long term member

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    Let's hear your most unexpected / unusual experiences.[/QUOTE]

    My Mistress invited me to a private munch at one of her friends house, a chinese was to be ordered and it sounded like a fun night with lots of fetish oriented people from gay to lifestyle and ProDomme BDSM'ers. On arriving dressed smart casual I was met at the door and taken out the back and dressesd as a french maid, no knickers allowed and black knee high platform boots, I had to curtsy and introduce myself to the guests and of course my very short skirt was pulled up frequently so they could see my cage or anything else they wanted, somekindly dropped food on the kitchen floor and I had to get down on my knees to eat it, I was terribly embarrassed and humiliated as had never been made to cross dress before or display my cage to so many strangers. Looking back I enjoyed it though, although I wanted the ground to open and swallow me up at the time.
     
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