Monday, August 22, 2016

Chastity and Periods

Mistress mentioned that she liked the idea of me being locked during her periods as a reminder of what she is going through.  I was looking for some relevant blogs.  This is the most relevant one I could find.  

This woman has it down to a science.  She has his entire month of chastity and orgasms synced with her monthly cycle.  28 days perfectly choreographed.  She goes from giving him 4 days of orgasms (5 a day) to a dead stop (the day she starts her period) to maximize his compliance when she needs it the most.  When her period is over his libido is built back up.  In the premenstrual days he is at his most obedient.  He is only unlocked 4 days a month and whenever she desires sex for the other 24 days.  His peaks coincide with hers.  Kind of hot really.    

That means he is locked 313 days a year (shudder).

A couple articles referenced in the post are linked below.

Sunday, August 21, 2016

Ramped up

I'm a little surprised how quickly 24+ hours in chastity has gotten me ramped back up.  Last night I had lots of dreams that I faintly remember as being sexy and with D/s elements, but I don't remember any of them.  I do know that I woke up a few times with my cock straining against my chastity device.  When I got ready for bed last night I stood in front of the mirror in my nighty and with my chastity device sticking out from underneath.  I felt so erotically humiliated.  This morning when I got up, and went to the bathroom I pulled up my nighty and sat down to pee with my pink chastity device squeezing my cock.  Again, so erotically humiliating.  To be a masculine guy at my age with such feminine and submissive tendencies just makes my head spin.  Just writing this makes my head spin.

I ran into a blog yesterday that I have been reading a bit    I haven't read much, but the few things I have read are her keeping her man in chastity pretty much 24/7, she frequently chains him to her bed, and he's forced to wear latex shorts as well as a latex maids dress

I don't know why the longer I go without cumming the more my brain fills with feminine thoughts.  I understand why I get more extreme fantasies, but the feminine part surprises me.  I would think the more cum I get stored up, the more I would have masculine thoughts.  Either way, my mind is a mess today.  A nice horny, desperate mess.  

Saturday, August 20, 2016

In a mood...

I woke up way too early again.  I wasn't ready to get out of bed, and I really thought I could go back to sleep.  Instead I had 2 hours of naughty thoughts going through my head.  The main catalyst for this is last night as we were going to bed Mistress told me that I had to lock myself up in the morning.  Also not cumming in 2.5 weeks is a pretty substantial reason.  So here is the mix of thoughts that crammed my mind this morning.

1st thought was about going back into chastity.  I felt my hard cock and especially the sweet spot a few last times before getting out of bed.  To avoid being tempted too much, I locked myself first thing this morning after feeding the dog.  I imagined a lot of teasing until Mistress decides to unlock me.  She is having her period which means I'll be locked for some time.  That reminds me of reading about Mistresses that keep their slaves locked when they have their periods to remind them to be sensitive.  Other Mistresses make their slaves wear panty liners or special panties during their periods.

We went shopping at a mall yesterday.  We walked by many stores that make my cock twitch.  The Bally, Maidenform, Hanes store.  A store that carried women's workout clothes.  Several stores that had women's clothes and when in stores, walking by displays of things that turn me on.  I don;t admit to it much, but whenever we walk by these items, whether in a mall, Target, Costco or any other place, my cock twitches just a bit.  I dream of Mistress humiliating me by buying something just for me and the public part of that shames me even more.  I am reminded of the times Mistress has done that.  Nighty shopping and Goodwill shopping for clothes for my feminine side.  It's a real mindfuck vs shopping online.  A couple stories that stick in my mind.  This Mistress taking her slave to get fitted for a bra at Victoria's Secret   Or this Mistress that sends guys into Victoria's Secret with a note that they don't know what is on it

I also spent a lot of time thinking about some naughtiness on an upcoming trip.  Thinking about panties, nighties, painted nails, clear mascara, maybe some perfume or women's deodorant.  Chastity under my swimsuit and on the plane.  Maybe a butt plug or the strap on.  A little public humiliation.  Possible bondage, teasing and denial and lots and lots of sex... hmmmmm


Friday, August 19, 2016

New Opportunities

We have had some recent changes in our world.  This means we will be spending much more time together and will have free time we didn't have before.  The other night Mistress said something to the effect of " since I have less control at work, I plan to take more control of you".  That is one of the hottest things I have ever heard.

My job has gotten to the point of where I work form home much more than I had.  This morning in my horny haziness of trying to wake up I had naughty thoughts of being put in unusual situations during the day.  I read lots of stories of Mistresses that make their slaves stay naked around the house.  Others make their slaves wear a suit while others keep their men in feminine wear or bondage all day.  Some torture their slaves during the day in intervals  I thought of having to wear clothes I see in ads in gay bondage websites or slutty outfits all day.

Mistress now has more time to watch or read naughty things.  She has the ability to be a task master and make me drop what I am doing to do whatever she wishes.  She can essentially have 24/7 control over me as her job won't interfere like it did before.  Mistress is very creative when she has the time and ability.  When we first met she had a voracious appetite for learning my proclivities and put me in some very unique situations.

I adore my Mistress and want her to be the happiest woman on the planet.  I am very excited to please her in any way I can.  


I did some quick math and realized I have spent more time in chastity this year than the last 2 years combined.

2014 - 17 days
2015 - 21.5 days
YTD - 48 days

We still have 4+ months to go.  Eeek!

Tuesday, August 16, 2016

A Nice Edge

It's been quite some time since I was a bit horny and unlocked at the same time.  It had been forever since I touched my own cock and nearly two weeks since Mistress had.  I decided to take advantage of my situation.

I browsed some blogs until I found one that had a hot story.  I open my pants and slowly stroked my cock until it got hard.

The blog post I chose was this one

As I stoked,  Here are some of the highlights as I started to read...

He was fully dressed, head to toe, with his wig, makeup done, wearing one of his amazingly sexy outfits, a black blouse with incredibly sexy, figure-hugging, super-tight white jeans that hugged his butt in that seriously sexy way.  He was even wearing his adorable, strappy sandals.

“Take your pants off,” I told him.  Then, after just a second’s hesitation, “The shirt and wig, too.”

Because as good as he looked with it on, I wanted to be rough with him, and didn’t want to mess it up, or have it get in my way.

...I had to stop...  and then start again...

Once we were there, I buckled a sturdy leather collar around his neck, pulled out a new dildo and shoved it unceremoniously in his mouth, slapping him around a bit.

And really, he was so fucking cute, gagging on the cock in his mouth, and choking when I shoved it in deep.

I was impressed, though.  I figured out that, when he’s given the chance to control it, he actually has some really good deepthroating skills.  There was one moment in particular when he, eager to please me, pushed forward hard against my hand, taking the cock as far as it would go, and holding it there, pushing even harder, until I felt that unique change in pressure as it slid far past the point that should’ve stimulated his gag reflex, and down his throat.

...I had to stop and start again...

He pushed himself to take it farther, to keep it there longer, until, coughing and sputtering, he pulled back, lowering his head as he gagged.

In the next moment, he took a deep breath, lifting his head back up, his lips parted as he waited for me to push the cock back into his mouth.

He really is an excellent cocksucker when he’s given the freedom to do it on his own.  When I fuck his mouth, however, he has a little bit more trouble suppressing his gag reflex.

Which is something I’m going to have a ridiculous amount of fun breaking him of.  I want more than him sucking cock.  I want his face thoroughly and relentlessly fucked by men who will further degrade and objectify him, reducing him to nothing but a pair of holes to take their pleasure from.

... I imagined my Mistress treating me this way...

Before long, his eyes started watering, smearing his makeup in that particular way that happens when women (or sissies) are made to choke on cock.  And it only made him hotter.

I was relentless with him, forcing it into his mouth, down his throat, grinning when his eyes watered and tears fell, his body convulsing as he tried hard not to throw up, and calmly and quietly enduring every slap that landed on his face.

He really is such a good boy, and he works so hard to please me.  A boy that good deserves a reward.

...I had to stop, longer this time.  Then I started again...

One of my favorite toys to use on any boy is a long, slender prostate massager, a kind that’s surprisingly cheap and common to find literally anywhere, which makes how effective it is even more amazing.  Most people would say it’s the most basic kind of massager out there, but sometimes the most basic kind is the best kind.

I lubed it up and sat on the edge of the bed, while he knelt on all fours in front of me, his ass to me.

“This is a fantastic view,” I told him, sliding the massager smoothly into him, using the angled bulb at the end to put pressure on his prostate.

He gave a low, shuddering moan and eased back, urging the massager deeper into him.  I grinned.  My darling, eager slut.  He loves it deep, and hard, and fast.

I kept the pressure steady, thrusting it smoothly in and out of him, until his moans intensified and I knew he’d had his first orgasm.

Oh, one of many, I thought, grinning, as I kept the pressure up, fucking him through his orgasm.

The second (or maybe the third) orgasm, he fell forward, the massager momentarily falling out of him.  I didn’t hesitate, pushing it immediately back in, keeping that intensity up.

Relentlessly, I fucked him with it, as orgasm after orgasm wracked his body.  More than once, he felt the carpet beneath him, expecting to feel his cum there.

But no, he cums like a girl now.  Not a man.

...Again, I had to stop...  and start again...  I imagined Mistress making me have orgasms from ass play alone and with no ejaculation...

I turned to him.

“I need the tub filled with cool water, I need something soft on the floor that you can kneel on, that you don’t mind getting wet, and I need an extra towel.  And wash all your makeup off.”

He nodded, hurrying to fulfill my commands.  By the time he was done, I sat on the toilet seat beside the tub, two lengths of rope in my hands.

I told him to come stand in front of me, positioned him the way I wanted him, and began tying the rope around his thighs, binding his wrists to them.

Once I was satisfied it would hold him, but wouldn’t be too tight, I had him kneel down, facing the tub, and stood behind him.

...stop...  start...

I pushed him down until his chest was resting on the edge of the tub, his face over the water.  And then, with a firm hand on the back of his neck, I pushed down further, until his face was submerged.

For a moment, he was still, obeying the unspoken command that was the pressure of my hand on his neck.

And then, once his lungs began burning, he began struggling, pushing up against me.  I held him down only a second longer before releasing him, letting him up.  I gave him a moment to catch his breath, then pushed him under again.

...stop... imagining me in this situation...  start...

This time, I held him down a fraction of a second longer before letting him up, pulling him upright by his collar, his head against my chest, and shoved the cock in his mouth, gagging him.  When he coughed and sputtered, I slapped him and pushed him back down into the water.

The longer this went on, the longer I held him down once he started struggling, the harder I made him push back against me before releasing him and shoving the cock back down his throat.

...I was so wanting to cum, but didn't...

I pulled him back to lie down on the bed, grabbed the lube, and began stroking his cock.  I knew it wouldn’t make him cum (and I doubted he’d be up for another orgasm at that point, even if he could), but I wanted something that would feel mostly good to him.

I mean, of course I worked it once he got sensitive, making him squirm.  I couldn’t be too nice to him.

But I didn’t torture him too much, or for too long.  He’d had a long evening.

At this point I decided it was best to put my cock away and get back to work.  It felt great to touch myself, and also to not cum.  I am in such a horny mood re-reading that story.  I could imagine doing every bit of it...

Thursday, August 11, 2016

New Outlook On Chastity

I started experimenting with chastity back in 1999 or 2000.  At the time I started with the CB-2000.

Not Me

This was such a new concept.  The thought of being under control by my then wife was so exciting.  The device was terribly uncomfortable, but I made due.  The biggest issue was that my wife never really got into the chastity thing.  I take that back.  She got into having me lock up and then forgetting about it.  I traveled quite a bit back then and to be on the road, locked up and having your keyholder ignore the situation was awful.  I am willing to trade some discomfort for the excitement, but the excitement wasn't there.  The device eventually broke while sleeping one night.  It was so painful that I still remember it.

I then upgraded to the CB-3000

The device was a mild upgrade, but still not worth the hassle without a keyholder that was not an active participant.  I became resentful.  Not at the concept of chastity, but at how it was implemented.  
Many years later the wife at the time started to get a little bit more into D/s and FLR.  We attended some events, visited a pro-domme a few times and that created an opportunity to try chastity again.  We decided to invest in a custom device.  I got a Price Alber piercing to prevent pulling out from the device.  We did lots of research and spent way too much money on a beautiful custom device.

This device was the best I have owned.  It was heavy but for the most part comfortable.  I still had the issue of my balls being pulled and after a week my scrotum would start to chaffe to to all the readjusting.  It's very secure, especially with the lock that goes through the piercing.  Within a year of getting this device my marriage had ended.  My new partner and now Mistress and keyholder took more interest in chastity, but the same issues came back.  I became resentful about chastity.  

In the last year I had a mindset change and decided that my being chaste was of showing I was invested in D/s.  The mindset helped quite a bit.  At the end of 2015 and into 2015 I went 4 weeks and 1 day in chastity.  It was the easiest chastity experience as Mistress was more involved than normal.  However the device was still more work than it was worth.

Over the last couple years I started seeing devices that didn't need to support itself off the testicles.  I was intrigued.  Men really seemed to like these devices and swore they were more comfortable.  I was skeptical as I have already invested a small fortune in devices.  I came across a plastic device that was 3-D printed.  

It's super lightweight.  In fact the lock on the device weighs as mush as the device itself.  If I use the plastic security tabs it;s only a couple ounces.  Since my sweet spot for an orgasm is right below the glans, I don't need a device that covers my entire cock.  Just the top third is enough to prevent me from trying to stimulate myself.  I can cheat and get an orgasm from a Hitachi, but you can do that with any device.  I really don't like Hitachi orgasms as much as friction based ones anyhow.  

So after 15 years of chastity resentment I have determined it was due to the discomfort of the device.  My current device is comfortable enough that I don't need the constant attention of my keyholder to override the discomfort of the device.  Obviously the more attention, the better, but the device itself creates no resentment for me.  I can ride my bike, run, lift weights, swim, etc and really not have to worry about the device all that much.  I can pee standing up for the most part but I still sit at home which most guys with piercings do anyhow.  I can wear whatever I want.  Feminine clothing is much more comfortable with this device vs other devices.  

All of that being said, I now find chastity enjoyable.  I recently went 2.5 weeks without being locked and kind of missed it.  I wasn't about to ask to be locked up, but was pleasantly surprised when I was told I would be.  All the fantasies I had for years are more believable now.  Having my cock locked and owned by my Mistress.  Giving up the right to touch my cock.  Giving up 100% control of my orgasms.  Being able to prove my fidelity (I'm not the cheating type, but a device certainly proves it).  All of the above with very little discomfort.  It's a match made in heaven for me.  So all of my years of complaining about chastity are over.               

Wednesday, August 10, 2016

Femme in Public

I've now been locked in chastity for 8 days other than a brief reprieve when I got my beating.  The chastity is now working its magic.  Even though life and work has been keeping any erotic thoughts out of my head, the constant feeling of chastity keeps pulling my thoughts in that direction.  I frequently find myself thinking about how I don't know what my cock feels like.  I am getting hornier and more desperate by the day.  As I have written over the years I dislike chastity, or I used to dislike it.  Now that I have a super comfortable device, I actually like it.  It's not perfect, but damn close.  I will soon write a post about how I view chastity now.

Today's post is based on a blog post I read a few weeks ago that I can't get out of my mind.  In the post, a Mistress takes her slave to get his/her makeup done professionally.  I frequently fantasize about being feminized in front of another woman, but the thought also scares the crap out of me.  Here are some of my thoughts.

  • I think about something similar to this story, or 
  • Me having to be feminine in front of a pro-domme
  • Having boudoir photos taken of me as my alter ego Sophia
  • Out in public dressed.  (Halloween, Gas Station, Drag Queen Events)
Here are some key phrases that stood out.

So we set an appointment for this past weekend.  And, as I’m sure you all know, I had lots and lots and lots of fun in the days and hours leading up to that appointment.  The poor sissy’s blood pressure was probably off the charts.  He was so nervous and flustered.  It was adorable.

More than the humiliation of having to endure it, more than being seen by more than one person that way, more than yet another piece of his masculinity being taken from him, that was what worried him the most.

“Do you want sweet?  Sultry?  Day?  Night?  Glamour?”  “Let’s go with sweet and innocent,” I told her, with a very not-sweet-and-innocent grin at Sounder.

Less than an hour later, she stepped back and asked Sounder what he thought.  He turned to me, and I couldn’t stop smiling.  He looked pretty.  Downright pretty.

Still, I couldn’t help but pull up his dress in the car and stroke him through his panties.  I drive an SUV, and he pulled his dress back down when we pulled up at a stop light next to another SUV.

Full story here -

There is a 2nd part to the story that isn't my cup of tea, but I am sure Mistress will enjoy reading.

Thursday, August 4, 2016

Happily surprised and a little worried

Last night Mistress decided to tie me up and have some fun.  I found myself tied spreadeagled and blindfolded on the bed.  Immediately a couple swift smacks to the balls and then the Hitachi turned on under my balls.  I was in heaven.  Mistress undid each leg and slid 2 rubber bands designed for binders up each leg before tying me back down.  She then alternated between snapping the rubber bands and using a super skinny stick and a fat rubber stick on the inside of my thighs.  She has done this many times before, but this time was different.  I couldn't put my finger on it.  It hurt more than usual.  Frankly it sucked.  She would occasionally stroke my cock, but not with any real purpose so it didn't do much to alleviate the pain.  She said she was punishing me for recent transgressions.

It turns out there was a reason for the pain to be more than I was used to, more than just punishing me.  She had a plan.  After reading for the last 6 years that I felt she was too kind, and didn't push me to my limit, she was going to do just that.  She kept asking if I was enjoying it.  While I was enjoying the bondage and the cock stroking, the beating fucking sucked.  She kept asking me if I was ready to call red.  I really didn't want to.  I became annoyed and mad.  I was pissed off and irritated.  I didn't like it.  There was very little eroticism to the pain.  I kept begging her to stop without saying red.  I didn't realize it at the time, but now I see I was testing her to see if she would quit or pull back.  I'm happy to say she didn't.

After I called red, she released me.  I retreated a bit while I dealt with these new emotions.  To add insult to injury she told me to lock myself back up in chastity immediately.  Well played.

As I knew would happen, what I felt last night has gone away.  Writing about the above experience got me hard.  Not hard because I got a beating I didn't like, hard because I have a Mistress that is willing to push me as well as punish me.  Truly punish me.  That makes being in a D/s relationship much more real.  Last night I truly submitted.  I had no control other than "red".  This is what I have been asking for.

Moving forward, I love the idea of playing closer to my physical and mental limits.  There are some challenges however.  Last night I was in a fight or flight response.  Had I been untied I would have left the room or physically kept her from hitting me.  Since I was restrained I had to deal with it so I alternated between emotional fight and flight.  Dealing with me saying and acting like "i don't like this" will be a challenge for her.  Pushing through that attitude and making me deal with it will be hard, but also very rewarding.  I am excited at the prospect and a little scared.

I woke up in the middle of the night last night and replayed the scene in my head.  Knowing that Mistress is willing to go until I beg her to stop had my mind running with other scenarios that push limits.  Below are somethings that could really test my limit and make we want to say "red".  It's also hot to think that "red" might be ignored.  I now believe Mistress has it in her.

  • Painful or uncomfortable bondage
  • Electricity 
  • Public Humiliation
  • Breath Play
  • Chastity
  • Teasing and Denial
  • Nipple Play
  • Cum Eating
  • Corner Time
  • Time Out
  • Cage
  • Piss Play
  • Strap on or fucking machine
  • Cross dressing
  • Public feminization
  • Oral Sex
  • Dildo sucking
  • Ball busting
  • Butt Plugs - extended wear
  • Scent Play
  • Edging

I know we can't always play to my limits.  It's her choice of when we do that.  I just want to end this by saying I am so happy she can be mean and sadistic if she wants.  I just hope it turns her on to be that way sometimes.

Tuesday, August 2, 2016

Too Nice?

Last night Mistress and I had quick but hot sex.  As soon as we started she started talking about some things she has planned on an upcoming trip.  Clear nail polish for both my finger and toe nails.  Panties almost every day.  Teasing and denial while I am locked in chastity.  Mistress fucking my ass with a dildo.  The sex was quick, but much needed.

Mistress is very kind to me and as a macho male I appreciate it, however my submissive side is looking back on last night thinking she was too nice.  First off, I came a bunch.  Half of me is thankful Mistress didn't make me eat any of it.  The other half is wishing Mistress at least smeared cum all over my face if not making me use my tongue to clean up.  The other nice thing Mistress did was not make me lock myself back up in chastity right away.  In fact, she went to work and told me to lock myself up after my bike ride this morning.  While physically I was happy to be unlocked for sleep and my ride, my submissive mind yearned for a meaner version of Mistress that locked me up the second I came.  The mind fuck of instant lock up is insane.   I guess what I am saying is that as a submissive male, meaner = nicer.