Uh-Oh

Mistress appears to have taken my recent blog postings to heart.  Yesterday afternoon, we had another intense scene.

I went upstairs and get things ready.  I puled the bondage straps out from under the bed.  I put my wrist and ankle restraints on.  I pulled out several toys and striking implements so Mistress could decide what she wanted to use.  I put towels on the bed, put some music on and dimmed the lights.  I laid on the bed, blindfolded myself and tied 3 of my limbs to the bed straps.

Mistress came in the room.  She restrained my 4th limb and tightened the straps down TIGHT.  Mistress put 8-10 clothespins on my scrotum as well as clover nipple clamps on my nipples.  I had recently added the clover clamps to the toy drawer as the clothespins are not intense enough for me. Mistress stroked my cock while lecturing me about my recent attitude.  She continued lecturing me and telling me how things were going to go from now on as she pulled the clothespins off of my scrotum causing me to gasp.

Mistress added rubber bands to my upper thighs and proceeded to snap them.  Out of all the implements we have used so far, these leave the best marks.  I was fortunate that Mistress put 3-4 bands together.  Combined, the pain they created was less sharp than a single band.

Mistress would hit the insides of my thighs and when the pain got too much she would stroke my cock to bring me back to my desperate horny state.

I lost track of time as Mistress continued to alternate between torture and pleasure.  Mistress told me how she intends on taking me to a local drag queen event.  First to observe, with the goal of taking me out in public the next time we go.  The thought scares me to death but also excites me.  At some point I will end up being fully feminized in public.  

Mistress also talked about putting me on a points system.  The more I serve her, the quicker I get to have scenes I enjoy.  Mistress also told me that she was going to start holding me much more accountable and enforce punishments much, much quicker.  I assured her that I want to be held to the highest standard and am willing to pay dearly for not serving her well.  I need to be doing more around the house.  To me this means I need to be doing chores while Mistress relaxes on the couch.  I would like there to be a 'honey-do' list every day.  I would like Mistress to remember that I am wired differently.  Having a list of tasks and being held accountable to complete it would really reinforce our D/s dynamic. There will be some challenges and push back from me, as she pushes me harder, but we both know I will be more fulfilled the more totally I am controlled.

At one point Mistress climbed on my face with her facing my feet.  She planted her pussy on my mouth.  I licked her as furiously as I could.  I tried to reach her asshole with my tongue.  I probably went about this the wrong way.  My intention was to show her how much I want to orally serve her.  I want to be consumed by her pussy.  I want to earn the privilege to be allowed to put my tongue in her asshole.  What I think I did is I went too fast and it wasn't doing anything for her.  I really do want to casually spend an hour or more between her legs worshiping her pussy.

I believe I almost got fucked in the ass with a strap-on, but I think a wardrobe malfunction occurred so instead of an ass fucking Mistress just put the dildo in my ass.  I kept wishing it was bigger and deeper.   

I am guessing after about 30 minutes, Mistress removed one of the nipple clamps and immediately rubbed the nipple.  OMG!  It was probably the most painful thing she did to me all afternoon.  Which is surprising considering how many times she hit my balls, smacked the rubber bands and hit me hard with implements.  That was until she the took off the second nipple clamp and rubbed my nipple which again was intensely painful.  On a scale of 1-10, my nipples are still sore at a level 1.  I was hoping for a residual pain level of 5-6.   

The longer the scene went on, the more I confessed my total and complete surrender to Mistress.  I confessed that I have totally embraced chastity.  For years I have resisted it unless it was for entertainment purposes, but now I believe it is in my best interest to be locked 24/7 for the rest of my life.  Release should only be for Mistress' pleasure.  I also confessed I have now accepted my feminine side.  I truly believe I am more subservient when I am dressed, perfumed, erotically shamed, etc.  My bad attitude is when my masculine side tries to take over.  I begged Mistress to keep pushing my feminization so that I naturally choose feminine over masculine.  I need encouragement if not outright force in the afternoons and evenings, when my libido is lower, as deep down I want to be dressed.  I just need help getting me over my last bit of resistance.  Lastly I confessed how much I want to kneel at her feet.  I think this act alone is a very powerful one.  Much like a queen asks her subjects to 'bend the knee' to show they serve her, and her alone.  It might feel uncomfortable the first few times, but I would bet a large sum of money that she would get used to it and eventually love the symbolism of me kneeling before her.  I would go into subspace very quickly with just this act alone.  It also a good position to orally pleasure her.

Mistress mounted my cock and rode me.  I really thought she was going to make me cum inside her and them make me clean her out. but she had other ideas.  We are going on a long trip soon.  I tend to get stressed and snarky when we travel and having an orgasm would just increase the chance for me to have a bad attitude.  I was to have no orgasm.  Instead Mistress gave me some instructions for the week.  I am to continue to stay in chastity until we leave and had to lock myself up the second we got done.  I hope she intends to keep me locked until the morning of our trip and not release me the night before.  I truly don't want kindness and mercy.  I am also required to wear my largest butt plug for 2 hours every day until we leave (I am wearing it now).  That being said, I believe I should wear it on the morning of our trip as well.  She also mentioned that we would be having another intense scene as a preventative measure at the end of the week.  That way when I get stressed and snarky she can remind me of what will happen if I don't change my attitude.  I am wishing we have a 'daily lesson' so to speak.  

Mistress managed to edge and beat me until I was a mass of submissive putty.  I don't think there was anything I wouldn't have done at that point.  She owned me.

Before Mistress untied me I asked her if I could add a few tasks to myself that I knew I would regret.  She indulged me.  I asked to wear my bikini in out hot tub.  She told me that I could.  I also asked to wear something slutty the rest of the night and she told me no.  I asked if I could wear pink leggings and a pink camisole and she said I could.

Mistress then untied one of my limbs  She told me to untie myself and that I would now be pleasuring her.  She ran off to the bathroom while I untied myself.  I was in such a state of subspace and pure desire to serve that I untied myself and knelt on the bed awaiting her arrival.  I was still wearing my blindfold and restraints.  Mistress came back from the bathroom and laid on the bed.  She told me to use my fingers inside her.  I begged to be allowed to go down on her first.  She told me 'no'.  I am pretty sure it's because she just went to the bathroom, but I knew that.  I really wanted to lick the remaining drops of piss from her pussy.  I can't think of a more submissive way to express my true desire and devotion than to do such an act.  It is also deep rooted in my brain as it goes back to my very first submissive fantasies I had as a pre-teen.

I obeyed Mistress and started to put my fingers in Mistress and instead she changed her and and told me to fuck her.  I did, much better than I expected but still was on the edge fast.  I then made her cum several times and she squirted quite a bit.  This made me want to grab a glass and catch her juices and drink them up.  She made me fuck her again.  This time I got too close to the edge.  I should have dribbled, but somehow did not.  Mistress was not having any more of that.  She had me make her cum a few more times and then she announced she was done.  I was disappointed as I didn't want this feeling to end.  Ever.

She had me clean up the room and put everything away.  I hate having to clean up after a scene, but being made to do so put me in the right frame of mind.  I am a slave and I don't get to decide what I want to do.  We then went to the hot tub. I was wearing my bikini.  If any of our neighbors were outside paying attention, there could have been 3-4 that could have seen me.  I was in such sub-space that I really didn't care.  I could see that becoming a new requirement.  Sitting in a hot tub in a bikini is way naughtier than being nude.  The feminine reinforcement is powerful.  

The bottom half of my bikini

After the hot tub, I did put on my pink leggings and camisole and made us dinner.  Mistress did a great job of reminding me of my outfit and my position as her slave.  I forgot to wear my butt plug when we got out of the hot tub.  I am fortunate Mistress reminded me as I was able to put it in at bedtime and sleep with it in for a few hours.  If I were her, I would have let me fail so I could have punished me for it.  I'm mean like that.  

At bedtime I thanked Mistress for her abuse.  I also encouraged her to keep at it.  This morning as I write this I am encouraged where this is heading.  I am still in pretty strong sub-space and am willing to do absolutely anything.  Mistress has now had a couple scenes where she has shown an ability to be mean.  I am truly scared of disobeying which is something I can only say a few times not only in this relationship but in my entire life.  I want to live in a certain state of fear because that fear is what will get me through my resistance and disobedience.  Fear will free me.

                 

        

Conditioning and Normalization

Mistress is really starting to do a good job of mentally torturing me.  Over the course of last evening, Mistress told me she had intended on letting me out for some D/s play, but I got home too late and missed out.  Of course I had no idea that was part of any plan so it's an extra mindfuck.  Mistress also mentioned that she had masturbated while I was at work.  I find that very, very hot, especially with my cock locked in chastity.  I imagine her texting me through out the day telling me she just had another orgasm.  It makes me want to be forced to track her orgasms on this blog along with my own.  Talk about a mind fuck.  Logging dozens and dozens of orgasms every month while I got months at a time without one.  Hot!  https://missbossybitchsboy.blogspot.com/p/history-of-orgasms.html

Mistress also played with my locked cock before bed.  Now that does several things to me.  It let's me know that Mistress acknowledges (and hopefully enjoys) my situation.  It gets me ramped up far more than I can ramp myself.  Having her fingers all over my locked cock, makes my head spin.  It reinforces my place in our relationship.

Being locked in chastity for long periods and having Mistress torment me, is exactly how my chastity fantasies play out.  Being locked and ignored is no fun.  Being locked and constantly reminded and tormented makes me want to stay locked forever and ever.

Last nights teasing has me pretty worked up this morning.  I woke up and my mind went straight to naughty town.  I got up and put a full spray of perfume.  I got dressed in some feminine clothes.  I have a fairly large selection (always want more) and I am forcing myself to wear things I rarely wear.  These clothes are more modest, which I am so no modest right now, but wearing more normal clothes, is an important part of normalizing my feminization.  I did put on my high strappy pumps and I tightened the straps a couple extra holes so I can feel like my ankles are restrained.

This picture I saw yesterday really spoke to me.

I recently had a dream where I have become so accustomed to being dressed that I stepped out of a hotel room to investigate something outside my door that I forgot that I was dressed.  In real life I have ventured out on the back patio in feminine attire, certainly very aware of my situation.  But the truth is that I am getting more and more conditioned to being dressed up.  I used to never wear my bras, but now I try to find a shirt where I can wear one.  Not because it's comfortable, but because it's not, and I am getting used to it.  I am too shy to wear my inserts though.  I used to wear heels for only a short period of time, but now I am used to them and walking in them.  They are not comfortable, but I miss them when I take them off.  On the weekends Mistress doesn't make me dress, but I can't resist and put on something casual but feminine when I wake up.  I do wish she "forced" me to be dressed more often or made me wear certain items to push my boundaries even further.  I love the conditioning and normalization of my feminine side as well as my chastity device.  I can't believe I can say that.        

    

Harsh Treatment - Yay!

Mistress and I recently had an anniversary.  Last night Mistress gave me a very memorable anniversary scene.

We came home after a couple drinks at a local bar.  We both had the right amount of buzz in us.  Mistress said she wanted to tie me up and I was more than happy to oblige.  Looking back through the blog, the last time I was tied up was March 28th.  I ran upstairs to take a shower and Mistress got out some champagne.  After my shower I got our bed ready for our adventure.  I pulled the restraints out from under the mattress, and put towels on the bed.  I pulled out all of the toys and laid them on the dresser.  I put on 2 ankle and 2 wrist restraints.  I put a large rubber band around each thigh as well as a blindfold over my eyes.  I proceeded to tie 3 of my limbs so Mistress would only have to restrain one.

Mistress came upstairs.  She finished tying me up.  It was then that I realized I had forgotten to put my perfume on.  I mentioned it to Mistress and she grabbed a pair of panties out of my panty drawer.  She sprayed a bit on the pair of panties and then put them around my head and over my nose.  I was instantly in a trance.  I can't explain it, but that perfume does that to me.

Mistress also added extra rubber bands to my thighs before tying me back down.  I don't remember the exact order of events, as it is now a blur, but I was well used.  Before the scene was over Mistress had massaged my prostate with her fingers.  She had inserted a dildo in my ass (unfortunately she wasn't wearing it).  I had clothespins on my balls and my nipples (my favorite).  She managed to hit me in the balls more times than I can count all while stroking my cock with a well lubed hand and a Hitachi vibrator.  I have multiple bruises on my thighs of where the rubber bands inflicted their excruciating pain.

Mistress had me so worked up that I was running at the mouth with confessions of how badly I wanted to be treated.  Everything ended with Mistress making me cum against my wishes.  Even though I came hard it was also a ruined orgasm.  She stopped or slowed down a bit when I started cumming so I lost that complete drain that can happen and then she kept stroking me to where I was laughing hysterically.  I was spent.  Or so I thought.  I woke up early this morning completely on 10 again.  I wanted to wake Mistress up and have sex but also want her to sleep.  My mind is racing with thoughts and I can't stop it.  Here are some of the thoughts I had while being tortured and some follow up thoughts.

• Feminization.  I begged for more and more feminization and I believe Mistress will enforce it.  Failure to either follow instructions or self feminize myself will be dealt with harshly.  I hope.
• This post https://missbossybitchsboy.blogspot.com/2017/08/enroute.html caused Mistress to comment on it last night.  I imagine coming home to an outfit by the door as soon as I enter the house.  Or a butt plug, chastity device, restraints, or certain notes.  I can't even enter the house without following the instructions first.  So hot!
• Harsher treatment.  Mistress was pretty mean last night with her actions as well as her comments.  I would like to be able to say I was scared or taken back by it, but I wasn't.  I am absolutely enthralled by it.  I begged to be treated as harshly as possible.  The thought of actually safe-wording or begging for less harsh treatment makes my cock hard.  If Mistress can get me to dread something in the D/s realm, she will have done something I didn't think could be accomplished.
• Scent training.  My perfume is working well.  I also begged Mistress to scent train me in other ways.  I imagine being restrained and having her socks or panties after she works out being put into my mouth and over my nose.  I can't explain why, but the idea turns me on so much.
• Order.  Being ordered to do things.  Being made to wake up to make Mistress her coffee.  Being made to change outfits throughout the day.  Being told to fetch items upstairs, not because Mistress is lazy, but to keep me obeying without question.
• The cage.  I get the feeling I will be experiencing the cage again soon.  Mistress seems to like it and I can't argue with its effectiveness, especially when combined with other items (straight jacket, heels, bondage, etc.)
• Chastity - More of it.
• Shocking collar.  I mentioned using it and Mistress seemed to agree in another context.  The thought makes me shudder.
• Challenges.  I am dreaming of Mistress making me do things with the sole intent of trying to get me to say 'no' and then punishing me for saying no.  

  In closing, Mistress has me so worked up with how she treated me last night and her comments make me hope for most of what she said to come true.  That would be heavenly.

The Dress

All week I have been getting progressively more desperate, which is one of my goals with orgasm denial and D/s.  All week I have been upping my feminine dress.  Wearing bras, and my highest heels even though they are challenging to wear.  I have 2 dresses that most people would consider inappropriate for most women to wear in public let alone a middle aged man.  All week I have been wanting to wear one of them and have chickened out.  That ended this morning.  I had the perfect combination of horniness and testosterone so that when I sprayed perfume on my chest first thing, I was at the mercy of my libido.

I chose a peach form fitting dress with a cutout on the side, definitely the sluttier of the 2.

When Mistress came down the stairs and saw my I have a perfect rush of erotic humiliation.  I also really like the way the dress makes me feel.  It's squeezing me in a good way.  The height is perfect. I feel sexy in it.  I am also so horny I feel like outing myself a bit.  I need to get something out of the back of my car and the only way to do that is to open the garage.  I would never do it (during the day) but the temptation is there.  Or going out in the back yard just for the risk of being seen.  This combination of chemicals running through my body has me all worked up wanting me to push my boundaries.

This dress also makes me feel very slutty.  It's the kind of dress I imagine myself in, on my knees sucking on a huge cock.  Or being fucked like the slut I am.  A fake cock but a huge one nonetheless.  

This is one of those dresses that I feel I should be punished for wearing.  It's not appropriate and a 'girl' like me knows better.  

It's also one of the dresses I fantasize about Mistress making me wear when she ties me up so that she can cut it off of me.  

It's amazing to me how the right a dress can make me feel.  Actually, many items of clothing make me feel this way but with different fantasies.  Like they say, 'the clothes make the man' :-)

Thoughts on this week

Today is the 5th day in a row of chastity and a butt plug.  When I woke up this morning I had zero desire to plug myself or to dress feminine.  Still, I have freely and willingly given up my right to decide these things for myself.  I inserted the plug, put on my rose scented deodorant and misted my chest with my perfume.  By the time I made it to the spare bedroom with my feminine clothes I was back into my slutty head space.  I am truly astounded how fast my perfume affects my mind.  Because of that I decided to wear a blue bra (Mistress has no bra requirements so far) a low cut top that matches and peeks out of the top, lace boy short panties, a too short skirt and my Mary Jane platform shoes.  Now as I write this blog, any lack of desire I woke up with has been replaced with a potent cocktail of brain chemicals such as testosterone that had my head spinning.  Add to that, being in chastity, being plugged, being dressed and being on my 70th day without an orgasm and I am kind of a mess.

By 8 am this morning I will have worn a butt plug for a required 13 hours this week.  It's likely closer to 15 hours as I didn't remove it promptly each day.  That's easily a record.  I have never been plugged 5 days in a row let alone for so many hours in such a short period of time.  The plug has gotten progressively easier to put in.  It's still not easy as it's relatively large, but it's easier.  Sitting on it is much easier than walking with it in as it doesn't move as much. One pint of interest is that I wore it in the tub the other day to shave my body.  Sitting in the tub drove the plug in even deeper than my office chair does.  As I sit here I am thinking of Mistress making me wear the plug when we leave the house together so she can frequently comment on it.    

Chastity.  No matter what I say or think about it, it certainly raises my libido.  There is literally no way to ignore my cock.  Regardless of the type of device I wear, I am hyper focused on my inability to touch myself.  The interesting thing is that if I am not wearing a device I can pretty much ignore my cock.  That being said, yesterday Mistress check out a new gym and left for about 90 minutes.  Had I not been locked in chastity, there is no way I could have avoided touching and edging myself.  

Each morning, when I get dressed I can deal with it pretty easily as my libido and testosterone is high.  Looking down and seeing my heels (and today's bra making it appear that I have breasts) make me feel super horny.  As the day wears on, I have a harder time being dressed.  Being in an outfit, walking in my heels, my feet starting to hurt, erotically humiliated, this is where the submission comes in.  Mistress could certainly make me more self conscious if she chose to, but she doesn't.  That's both good and bad.  Accepting and encouraging me to be more feminine will allow her to keep pushing me.  At the same time, occasionally making comments about my attire or groping me, is a very powerful mind fuck.

My attitude.  I have been snappy a few times with Mistress.  She has told me to watch myself a few times.  The clear idea was that I was about to spend time in the cage.  Just the thought of it brings me back to my place in our relationship.  I dislike being in the cage, but I love it when she is strict with me.  

Although I have had some challenges this week, I would call it a success.  Mistress has added items to my task list.  The result is that I am in such a state of mind I don't want it to end.  I want to go deeper.  My mind is desiring more restrictive, challenging, feminine, humiliating, painful or disgusting things to happen to me.  I am kind of addicted to the chemical cocktail going through my brain.        

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

The power of scent

One of the biggest surprises I have had in recent years is understanding the power of a scent.  I knew that smells can bring back memories of a long time ago.  Every time I smell leaves in the fall, I am immediately reminded of walking home from school back in junior high over 30 years ago.  Fresh cut cedar takes me back to my first job also 30+ years ago.

That brings me to current time.  Mistress bought me some perfume before Christmas so that I could add it to my daily feminization.  Out of all the feminine things I do, wearing perfume has the strongest, most immediate impact on me.  I can have pretty much zero femme thoughts when I wake up, but one spray of perfume on my chest and my brain goes into feminine overdrive.  It makes me WANT to be more and more feminine.  It pretty much removes any desire I have of resisting feminization.  When I pick out my feminine clothes for the day, the perfume makes me want to choose sexier, sluttier or classier clothes.  No jeans and t-shirts, but skirts, dresses and uncomfortable high heels become my choice of attire.

I had been planning on writing this post for some time, but what triggered it today is a post and caption I saw online.

It wouldn’t take many nights like this, only being allowed to cum or even touch himself without the smell of her filling his nose, before the scent of her would become pleasure.

I often fantasize about Mistress doing this to me.  I love the idea of the panties being worn by her all day ending up on my face any time my cock received attention.  I love the idea of training my brain to make her worn panties an aphrodisiac.  To train me in such a way that I can't get off without her scent.  Some duct tape to keep me from breathing through my mouth and some worn panties or pantyhose stretched over my nostrils.  I would be in submissive heaven.

Or even worse, my own worn or cum stained panties or pantyhose.

Just thinking of being tied down, blindfolded, teased, denied, and tortured.  Having Mistress' scent fill my nostrils and my brain.  Just thinking of it makes my cock hard.

Writing this I am reminded of a blog where a Mistress used her dirty socks in this manner.  Even more devious, she made her slave get turned on whenever she took off her shoes.  http://wedlocked-femdom.com/2014/11/22/training-the-slave-to-become-aroused-by-a-smell/

In closing, scent is very powerful.  Much more powerful than I ever imagined it could be.  I am starting to fantasize about all the ways we can use different scents in a D/s way.  From adding perfume to my nightime routine or adding a pair of worn panties to my nostrils next time I am locked in the dog cage.  The idea of having shoes taped to my face or being forced to smell Mistress' socks to condition me, it's all very erotic to me.