Terrible Orgasms

I have been getting in a deeper state of desire over the last couple days.  Being locked in chastity and having my ass plugged seems to be a perfect cocktail to get me hornier by the hour.  Last night, after Mistress and I got out of the hot tub, Mistress was showing off her pedicure.  I tentatively licked and sucked one of her toes.  She didn't stop me so I kept going.  Then I got a bit of encouragement.  I was in heaven.  I frequently fantasize about licking and sucking Mistress' as well as kissing her feet and shoes.  I really wish I could do it more often.

Last night as we were falling asleep, Mistress told me that I would be plugged for 3 hours today.  My plug went in at 5:58 this morning, so this particular task should be done by 9am.  This is the 3rd day in a row of being plugged.  It's possible this is a record, but I can't be sure.  By the time Mistress' period is over it certainly will be a record.  I have also noticed it's a bit easier to get the plug in.  I don't have to push in and out as much before I push it all the way in.

Plugging myself first thing in the morning, in addition to my perfume and the clothes I have to wear, I start my day feeling a desperate form of sluttiness and erotic humiliation.  The more Mistress requires of me, the more I want to experience.  Instead of pushing back, I want to go deeper.

After I wrote yesterdays post that touched on having my next orgasm be terrible in some way, I have been thinking about other ways to make it awful.  Not because I want an awful orgasm, I just want to have zero control over what happens to me.

I have been fantasizing about having to impale myself on Mistress' cock.  At some point she would make me cum and lick it all up.

After licking Mistress' toes last night, the idea of having to masturbate on her feet and lick them off sounds humiliating, especially if I had to wait for the cum to cool.  The 3rd picture looks like a ruined orgasm to boot.

Having to cum in chastity and stay locked up seems particularly cruel.  Even worse, saving it to consume later.

Being stimulated with painful electricity during and after an orgasm would be on my list of fears.

 Having a clothespin zipper looks very hot but would be so amazingly painful.  Maybe that's a good thing.

Having my balls punched or squeezed every time I got close to orgasm would likely make me cum, but would prevent an actual orgasm.  Probably the worse kind of ruined orgasm.

I have read of this scenario many times, so I was surprised how hard it was to find a picture.  The premise is that the slave doesn't deserve to cum with a person.  He has to have humiliating sex with a doll (male or female doll).  After orally performing on the doll for an extended period of time, he is told to orgasm.  Afterward he has to clean off the doll with his tongue.  The stories I recall had the Mistress taking pictures and video so that she could use them in further humiliations.  Or even worse, doing this with others in attendance.  Some good public humiliation.

As I read back through this post and look at the pictures, I am actually disturbed by some of the ideas I came up with.  Most would be a challenge for me and some would outright suck (no pun intended).  That being said, I know I would look back when my libido recovered and be extremely turned on.  I take a certain amount of pride of having to endure something that I don't want to endure.    

Locked, Plugged and Dressed

I sit at my desk this morning with my ass plugged and my cock locked in up in chastity.  Since it is now spring, I am wearing lace boy shorts, a white blouse, white skirt with a floral pattern and high 6" strappy pumps.  My head is spinning with desire.  If there was any way to stroke my cock right now I don;t think I could resist the temptation.

On Sunday Mistress informed me that I would be locked in chastity along with having to wear a butt plug for 2 hours every day of her period.  I can see this becoming a monthly ritual and I hate to admit that I like it.  Having scheduled torments for to endure are a pretty hot idea.  Mistress can tease me days in advance that she will be starting her period and that I will be locked up and plugged soon.  All that I am missing is something phallic in my mouth :-)

I half woke up about 30 minutes before I got out of bed, tossing and turning hoping to go back to sleep.  With my cock straining against my device, I had no real hope of falling back to sleep.  My mind was racing with naughty thoughts.  I imagined Mistress making me dress up and take a ride in her car.  I imagined being locked in the cage to remind me of my place.  I imagined Mistress making me walk in these heels on our treadmill.

It's not been 67 days since my last orgasm.  My mind has been filled with extreme ways of making my next orgasm as unenjoyable as possible.   I imagine being edged and edged over again until I am bucking at my hips. I imagine just being allowed to dribble until I am dry.

If that happened I technically still wouldn't have had an orgasm.  I imagine Mistress making me cum, but not stopping stimulation until no matter how much I begged.

Lastly I fantasized about her making me clean very single drop up in as humiliating and disgusting way as possible.  Licking every drop off her body, especially after it has cooled and I have come down from the height of pleasure.  

I am certain that eating my cum after such a long denial period will be the worst part of it all.  It will also be the part I play back in my mind over and over again.  Some of the worst things ever done to me are the best!

  

   

Mistress' Fantasy

The other night before bed, Mistress asked me if I would ever consider having a threesome with a transsexual.  Mistress knows I have fantasies of threesomes, but my fantasies of threesomes are with 2 girls and a guy (me).  Don't blame me for this, I was born this way.  I have my "deviations", but bisexuality isn't one of them.  I have no problem with gay sex or transsexuals, it's just not for me.

Now Mistress has been with women.  She likes for me to be dressed up as a woman and some of our best sexual scenes have been with me in full feminine attire including full makeup and a wig in addition to women's clothes.  These have been extremely hot times.

Now my idea of a threesome is probably different than most.  While having sex with 2 women seems hot, this is my typical idea of a threesome.

 

Even though I can't imagine myself with a guy or transsexual, I absolutely love simulating that type of play.  I have huge fantasies of choking on a strap-on dildo shoved down my throat until tears are running down my face.

Count't find a man sucking a dildo with mascara running

I fantasize about being fucked in the ass until I orgasm without any cock stimulation (still haven't done this though).  Pretty much any porn that shows a man dominating a woman, I flip in my mind to it being a woman with a strap-on treating me the way the woman get's treated.
      

Now I am a "never say never" kind of person.  I am pretty certain with the right kind of conditioning, training, teasing and motivating that Mistress could get me to where she wants me.  I don't like the word "force", but I eventually could be coerced into crossing my hard limit if Mistress really wanted me to.  She has already done so as far as having me dress feminine so much.

I imagine my training as having to watch certain TS porn instead of any other kind.  Having Mistress tie me down and stroke my cock until I go mad with desire, all the time telling me what her plans are for me.  Making me repeat what she says until I can't think of anything else.  Making me simulate bi-sexual activities with toys as much as possible.  Of course cum eating is also an important aspect of it all.

And now for some images for Mistress and her TS fantasy