Miss Bossy Bitch's boy

Tuesday, March 21, 2017

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!

Sunday, March 19, 2017

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

Friday, March 17, 2017

A hot scene

I was perusing my blog list and came across a post that spoke to me in a way that coincides with my mood.

A slave is tied down on a table, exposed and immobile. He has a machine slowly fucking his ass. His Mistress has rolled a condom on his cock and is using a Venus 2000 masturbation sleeve to tease his cock.

In the next shot the machine is still slowly fucking his ass. You can barely see it, but he cums into the condom as the Mistress removes the stimulation on his cock and rubs and squeezes his balls to get more cum to release. I imagine it was a ruined orgasm instead of a full orgasm.

In the next shot, his Mistress carefully removes the condom to keep it's contents inside and proceeds to drip the slaves cum into his mouth. All of this is happening with his ass still being slowly fucked by the machine. If I was in his shoes I would have a hard time opening my mouth. I like to think I would have a gag in my mouth that would not allow me to refuse my cum.

Next, the slave is locked into chastity again. I am not sure why she stopped the machine. I wouldn't.

Lastly, Mistress leaves her slave, still bound, still being ass fucked with the nasty taste of cum in his mouth. I can only imagine the thoughts running through his mind afterward. I know mine would be shame and disgust, but at the same time strong mental arousal.

Very hot indeed.

Thursday, March 16, 2017

Thoughts of torturous orgasms

For a guy that is trying to set a personal orgasm free record I am surprised on today's fascination with ruined orgasms along with post orgasm torture. One down side to long term denial is the eventual orgasm isn't as good as one every few days.

There are several ways that I find arousing. The best one is a long slow tease. Without even getting close to the edge. Going mad because even the feeling of orgasm is so far away. After a sufficient amount of time, some edging.

I can't say for sure as I don't remember, but it seems the best torture is to be edged close enough to the edge but with zero intention of allowing an orgasms. Working my cock time and again until I end up dripping several seconds after Mistress stops stimulating my cock. The goal being that I leak several times with never approaching orgasm until I am completely drained.

The next worst would be similar to above, but eventually allowing an orgasm, but with us both knowing that when I do orgasms, the stimulation will not stop, no matter how much I scream and beg. I love to think that Mistress could force a 2nd orgasm to torture me again.

Now I know I would hate either one of these. The first I would hate the most as I wouldn't even get the pleasure of an orgasm. I am guessing it's also the way I would be ramped up the soonest afterward.

Having zero control over how Mistress would drain me is the only reason I find this concept so hot. Knowing that my orgasm would suck would be such a mind fuck.

I also believe that either option would necessitate the use of a chastity device for a few days afterward. I don't think I could resist the desire for a real orgasm until my libido got built back up. In addition to removing the desire to cheat, it would also make me hornier faster.

Here are some videos of ruined and tortured orgasms.

Maitresse Madeline Compilation