Sleepwear

Last night I wore a nighty. It’s been months since I wore a nighty.  When Mistress asked, “where’s your nighty?” as I was crawling into bed, I got instantly aroused. I happened to be wearing panties at the time so l left them on as well.   I’ve never slept in both a nighty and panties before. The panties had an added effect on me. I had forgotten what it’s like to sleep in a nighty.  Normally I sleep naked. Wearing the nighty was a constant reminder of my feminine/submissive side. The straps digging into my shoulders. The satin rubbing my freshly shaved body as well as my nipples, arousing me further.  The restriction of my movement, all working together to turn me on more than I already was.

Adding the panties even pushed my buttons more. The panties restricting my normally free cock. Slightly riding up into the crack of my ass. The panty and nighty combo were certainly more powerful than either one by itself.

It’s 4AM and I can’t sleep.  I am sooooo horny. I don’t know the last time I had an orgasm, but it’s been weeks.  I want to edge myself so badly but I am afraid I’ll have an accident.  I’ve been obsessed with my eventual birthday beating, watching videos of guys and girls getting brutalized far harder than I would ever want with canes, whips, etc. It horrifies me as much as it arouses me.

The last couple of mornings, under my male clothes, I wore the swimsuit that I stole from Mistress’s donation pile. The swimsuit is very tight and restricting  The bra strap on it dug into my skin.  My cock and balls were severely confined. The bottoms rode up in the back. The front of the swimsuit is full coverage. The back of it is just the bottoms and the bra strap which left my back completely exposed. The thighs were cut high enough that I could see the skin of my hips over the top of the waistband of my shorts. In addition to wearing it around the house, I also wore it when I took the dog for a walk and while running errands. I was VERY self-conscious.  I felt like everyone could tell I was wearing it under my clothes.  I was very careful to not let it be seen while getting stuff done around the house. It was fairly uncomfortable, which in my mind was what it should be. Essentially being punished for being so desperate and horny that I was wearing a woman’s swimsuit under my clothes.  I’m always amazed by how much of my feminine side is awakened the longer I go without an orgasm.

That’s enough for now.  I’m going to try and drift off to sleep in my panties and nighty.

 

Panty Thief

Mistress and I are moving soon, into a much smaller space. We’re downsizing quite a bit. One thing we’ve learned is that we have far too many clothes.  We tend to wear no more than 5-10 of any one item, but for some reason have 30, 40, or more of a particular item.

I’ve had to get rid of a lot of my male clothes as well as all of my female clothes that were hanging in the closet.  Things such as dresses, skirts, and blouses.  Things I could wear around the house, but sadly haven’t in some time. Next, I have to tackle my female clothes that are in the dresser. These are panties (far too many), pantyhose, stockings, bras, nighties, and some lounging around attire. I’m going to get rid of the majority of these and just keep a few things of my favorites and Mistress’s favorites.

Mistress has also had to downsize a lot.  She has filled bags and bags of clothes to donate to charity. Every time I see a black trash bag with her clothes in it, I am overcome with a need to investigate. A few weeks ago it was panties and other lingerie that hadn’t been worn in nearly a decade. I browsed through the bag sitting in the garage waiting to be donated. I couldn’t help myself.  I just had to keep a few choice items for myself. Mistress almost caught me during my hunt. I had to pretend I was organizing the trash.  I kept going back to the bag over the next few days, making sure I didn’t miss anything.  Mistress is much smaller than me so I can’t wear many of her clothes unless they are very stretchy. Over the weeks since then I’ll slide into a pair of her recycled underwear.

I have my own panties (lots of them), but there is something taboo about taking a woman’s underwear and sneaking around wearing them that adds some excitement. It reminds me of when I was 15 years old and would go to one of my friend’s homes. He had a very hot older sister and I once stole a couple pair of her panties and wore them when I got back to my house. It was exciting and a turn on. I would fantasize about her catching me stealing her panties and my fantasy had her blackmailing me into being her slave by threatening to tell everyone what I had done.  She would verbally taunt me about being a panty thief and would spank me as punishment.  Stealing Mistress’s panties and sneaking around about it reminds me of that thrill I got way back then.

The reason this is coming up now is that Mistress has another trash bag of her clothes in our upstairs closet. It’s mostly swimsuits but has some other clothes in it. I have been in that bag at least a half dozen times. The first time I quickly squirreled away a half dozen items in case the donation happens too quickly. Since then I’ve gone through the bag, tried in some items (most don’t fit) but got lucky on a few. The other day I wore her too small for me bikini bottoms.  My cock and balls all crushed up. It was exhilarating.  I almost got caught going through the bag the other morning. The fear and excitement of possibly getting caught made my heart skip a beat. A couple items I wish I could keep, but space will be limited so I have to be extremely choosy. As I write this post, I’m dressed in a one-piece swimsuit under my shorts and polo shirt. It’s several sizes too small but I was able to stretch into it. It’s constricting, making me aware of every breath. It feels so forbidden and that turns me on.  I’ll wear it for the next few hours until my morning libido wears off. My mind will be spinning. One side of me is wanting to be caught by Mistress. She’d march me upstairs and make me undress down to the swimsuit. She’d verbally taunt me as she’s tying me down to the bed before using the cane on my swimsuit covered ass. She’d make me promise to never steal one of her items again while I screamed out in pain. She’d taunt me about making me sunbathe in the swimsuit to give me obvious tan lines to humiliate me. She’d threaten to make me buy my own women’s swimsuit to wear.  Just thinking about it makes my confined cock spring to life.

Reflection

This morning I woke up, fantasizing about getting a birthday beating. I started thinking about how much it’s going to hurt. I realize that if done the way I am begging for,  I’ll have bruises for a week, it will hurt to sit down for several days and it will take me past my limit.

I’ve also been fantasizing a great deal about Mistress getting stricter with me. Making sure I always have something feminine about me.  Punishing me for talking back,  being disrespectful or failing at tasks that need to be done. Pushing my submissive buttons to manipulate my behavior in a way that favors her.

Why do I want to be hurt?  Why do I want to wear uncomfortable panties and other clothes, or nighties that are difficult to sleep in?  Why do I year to suffer at the hands of my Mistress? 

I truly believe that I need to have control taken away from me. Being tied down and beaten harder than ever isn’t about being beaten.  While I am certainly sexualizing it, I know that the eroticism will quickly go away and I’ll have to deal with non-erotic pain. It’s deeper than a sexual fantasy, it’s psychologically driven. It’s about relinquishing all control to the woman I love with all of my heart.  It’s about me making myself vulnerable to her. Being tied down will force me to remain vulnerable while I try to stop the inevitable.  Being physically hurt will break down my domineering and controlling walls.  I need to be taken down a peg.  I need to be less in control. I’m not good at it. I need to serve my Wife and my Mistress. She’s my everything and me trying to be the boss or have things my way just doesn’t work very well.

Rarely do I give much thought to the why of my fantasies. For the last few weeks I’ve been fantasizing about the sexual aspects of this, but usually, that fades away. The fact I am still so focused on it has made me examine where this need is coming from.  I’m surprised by the results of my self-examination.  I want to serve.

Nervous Anticipation

I had dreams last night, but I don't remember any of them. What I do know is that I woke up extremely horny today.  Mistress and I still have to coordinate my birthday spanking.  I really mean birthday beating as spanking seems to tame to me.  I am to receive at least 51 strokes of the cane or other implement.  A stroke doesn't count if the stroke doesn't cause me to make a verbal response, nor does it have to stop at 51.  One of my readers left a comment that in addition to his birthday spankings, he also gets spanked for his wife's birthday. In my case, Mistress just had her birthday and that would mean an additional 46 spankings.  Just typing that last sentence made my cock hard.

My mind has been a bit consumed with the anticipation of this happening.  The problem is that we are moving soon and we are so unbelievably busy that we haven't had time to make this a priority.  It doesn't stop me from thinking about it when I can.  I imagine all sorts of variations.  Dressed up in a feminine matter. Gagged with a ball gag, a ring gag, a penis gag or Mistress's dirty panties.  A thick buttplug inside me or not.  In my chastity device to keep me from rubbing my cock against the blankets or my cock tied to the bedframe to keep me from squirming.  Legs tied together vs being totally spreadeagled on the bed.  Mistress ignoring my pleas to stop.  I would purposely be quiet, even though a stroke hurts immensely or I would fake a sound to stop the pain early.  Taking lots of pictures to post here in this blog  At the end of the day, I really want to endure the hardest spanking of my entire life. 

This last one is too tame.  

Birthday Beating

I have a birthday coming up and last night Mistress told me she didn't buy me anything.  I told her, "thank you for not buying me anything".  We are fortunate enough to pretty much buy what we want, presents for holidays and birthdays are more stressful than rewarding so we tend to skip them.  As far as my birthday goes, I prefer birthday shenanigans way more than any gift or special meal out. 

When Mistress told me that she didn't get me anything I told her that I would much rather have a birthday spanking than any gift.  You can't really buy a spanking, wait, you can, but that's a different story.  I told her I would love to get a minimum of 51 swats, stokes, etc for my birthday.  Mistress asked if we still had the cane in the bedroom and I assured her we did.  I then said that a stroke doesn't unless I make a sound.  She said, "oh, I'll make sure you make a sound".  My cock instantly got hard.  That was pretty much the end of the conversation and we went to sleep after a long day.

This morning I was stirring awake when I really wanted to be falling back to sleep.  As I tried to go back to sleep, my mind kept wandering to last night's conversation.  I imagined my Birthday Beating.  I won't be able to be beaten on my actual birthday as we have other things going on, so we will have to make alternate plans.

Now I am not really into pain for pain's sake.  It's kind of like spicy foods. I love spicy food however, there are some spices that are hot just for the sake of being hot.  There is nothing else to them.  If a portion of food is super spicy, yet it's very flavorful, I will gladly suffer through the pain.  Same thing with pain from BDSM activities.  Pain for pain's sake is not fun.  Pain that comes with the loss of control, or with a certain goal in mind, or for the arousal of the pain giver, those all make enduring pain worth it.  In this case, knowing I will get at least 51 stokes, and that there is nothing I can do to stop them (unless it's a real emergency) is a massive turn on. 

Of course, my dirty mind had to find ways to make the beating more interesting.  I imagine having to wear my butt lifting panties.  They create a nice target for Mistress to focus on, but then that might not spread out the pain enough (shudder).  I can also imagine other feminine additions.  Schoolgirl skirt and top.  Eye makeup so that it runs as tears fill my eyes.  A penis gag or dirty panties in my mouth while I get beat.

I imagine having to wear my largest butt plug.  Each time I would get hit, my natural tendency to clench my butt would stimulate my prostate.  This, in turn, would confuse my senses by connecting the intense pain to the pleasurable feeling in my prostate.

I imaging Mistress taking breaks from beating me to masturbate while I lay there with my ass throbbing.

I imagine Mistress taking out recent frustrations on me. We have had a particularly stressful couple of months.  I have had some very dickish moments, and deserve to be punished for them.  Nothing like being able to add some payback onto the birthday present I asked for.

Suffice it to say, I am fearfully and excitedly looking forward to the best beating of my 51 years.  I imagine begging Mistress to stop, but not actually using a safe-word.  I imagine purposely trying not to make a sound so that I can get hit longer.  If I end up looking like the poor guy below, I won't regret it.   

Back for now

Mistress and I have had a ton going on.  We started a business a little over a year ago and we have been busier than our wildest dreams.  It's been stressful so we have had more arguments than usual.  Nothing serious, but enough that we haven't engaged in kink in quite some time.

We also went on an extended road trip without any toys, feminine items, etc. 

Lastly, my extended time in small chastity devices appears to have caused my penis permanent damage.  I now have a medium upward curve to my penis from something called Peyronie's disease LINK. It doesn't affect much, but it means extended chastity is more or less off the plate.

Mistress and I have been home for a couple of weeks but I don't think it's appropriate to ask for D/s if she's not feeling it.  Because of that, I've been secretly doing things to myself.  I wear a silicone cock ring almost all day.  I have been locking myself into chastity for short periods of time (it's so addicting).  I have actually slept in chastity twice in the last week.  Mistress has fallen asleep on the couch and I've been a little drunk and extremely horny and that's how I have handled it.  I have worn panties almost every day since I have been home (I missed them more than I thought).  I wore a women's body shaper out of the house under my clothes to take the dog to the dog park and on the way home I exposed myself for the 5 mile drive through town.  I have never done anything like this before.  Scary but exhilarating!

As I type this I have my prostate massager in my ass.  It's the first time I have had anything in my ass for at least 6 months.  I missed this too.

My current fantasies are running through my head.

• Giving Mistress multiple orgasms while I have none.  
• Being locked in the dog kennel overnight.  Mistress has threatened this over the years, but I would hate/love to be forced to do.
• Long-term chastity.  Being locked regardless of the consequences.  Mistress likes my fingers more than my cock anyway.
• Public crossdressing. Now that the streets are so empty due to the coronavirus, I'd love to be forced to walk down a street dressed up.
• Secretary attire every day since we are sheltering in place.
• Fucking Machine Punishment
• Being tied down while the Venus 2000 penis pump gives me an orgasm, and then keeps going no matter how sensitive I am and keeps pumping until I cum again, no matter how long it takes.
• Crossdressing in a video chat room.

Have a great rest of your week.  Stay safe!

What I did

Mistress was out of town for a couple of days but is coming back this evening.  I had some alone time for the first time in over a year.  So what did I do?

First I wore my feminine outfit until I had to get ready to leave the house.  When I did leave the house I wore a vinyl thong with a built-in cock ring.  When I got home that night I put on my pink lounge clothes. 

When it was time to go to bed, I had one thing to try.  I have been wanting to see if it's possible for me to have an anal orgasm with no stimulation on my cock.  I have tried this before without success, but this time I had success.  I used my Aneros prostate massager as well as the Hitachi.  It took me quite a while to find the right combination of D/s items and vibration, but eventually, I did it!  I needed some extra stimulation so I used a spider gag to imaging being fore fed my cum.  I wore nipple clamps as well as a cock and ball strap.  Of course, I had to wear something feminine since I was trying to cum like a girl.

The next morning I had to run some errands and decided to dress up under my clothes. These look like grandma panties, but in reality, they are a thong in the back so my ass cheeks stick out.  Perfect spanking panties as the ass is framed perfectly for aiming a spanking implement.

When I got home I decided to play with my Venus 2000.  I ended up tease torturing myself, not allowing me to get close to the edge.  I wasn't able to do this very long as I wanted to cum very badly, which I did.  It was amazing!  If only I was tied up and Mistress kept me going like this for hours without cumming.

As I was getting the toys out of the storage area, I ran across a bullwhip I bought Mistress years ago.  I playfully smacked myself with it about 15 times.  Just enough to make it sting, but nothing I consider very hard.  Imagine my surprise when I see that I am marked by these fairly light flicks of the whip.  This really, really wants me to experiment more with the whip

Bummed it's out of focus

Well, that's it for playtime.  I have to put everything up and clean up the house before Mistress gets home.  I may have to wear something naughty to go pick her up at the airport.  I sure did miss her.  This kind of play is so much more fun with Mistress.

  

  

While Mistress is away.

Lilac women's deodorant and women's perfume fill my nostrils.  Eyelashes weighed down with mascara.  Lips heavy with red lipstick.  Dark pantyhose/tights worn for the 1st time in over 2 years.  Heels and a dress worn for the first time in over 12 months.  Heavy silicone bra inserts in my tight dress.  My head spinning as I walk in heels for the first time in months.  Every few steps having to pull down my skirt to keep it from riding up.  Clicking heels on the hardwood floors fill my ears. 

Mistress is away for a couple of days, so I am going to take full advantage while working from home.  Mistress also chose not to lock me in chastity.  I'm going to try not to cum, but with some of the toys I have access to, I don't think I will succeed.

Whatever will I do for the next 48 hours?  If you have any ideas, please comment.  I'll update a few times as things happen.  Soooo horny!

Orgasm Overload

When I was being denied orgasms for nearly the last 3 months I was really enjoying the neediness, desperation, and submissiveness that was created.

Now that I’ve cum a couple times I am craving more and more orgasms.  Instead of no orgasms, I’m wanting to be forced to orgasm until I’m begging to not cum. Since I came a couple weeks ago I can’t get this fantasy out of my mind.  I envision a couple different ways this would happen.

Mistress picks a weekend to indulge me and gives me a set of instructions. I am to be in our bed at the top of every even hour, naked and have 3 of my limbs self-restrained. We would have our Hitachi vibrator, Venus 2000 masturbation machine and a couple of masturbation sleeves available. Just before 8 am on a Saturday I head upstairs and restrain myself to the bed. Mistress comes in and pulls a blindfold over my eyes and restrains my untied arm and then walks around the bed tightening all of the remaining limbs.

She climbs onto the bed and lubes up my cock with coconut oil and stokes my cock until I get hard. She then mounts my cock and fucks me while I am tied down. She proceeds to tell me that she is going to take the whole weekend to milk me dry and unable to cum. She says she won’t be satisfied until I’m begging her to stop with tears in my eyes.  She tells me that we will start with the ways to make me cum. Her pussy. Her hand a masturbation sleeve. Once those no longer work she will move on to the heavy machinery of the Venus 2000 and the Hitachi. She says she’ll be adding certain elements such as nipple clamps, cock straps, butt plugs and other items that she knows pushes my buttons and gets me to orgasm faster. She also tells me to expect lots of post orgasm torture.

In no time I am at the edge and I ask for permission to cum. She tells me that this weekend I do not have to ask permission to cum but I do have to tell her when I am about to cum. I tell her that I am cumming and I quickly fill her pussy with a lot of cum. Mistress climbs off my cock and sits on my face and orders me to lick her clean. She then informs me that I will be eating as much of my cum as possible.  As soon as we are done Mistress releases my limbs, tells me to leave the wrist and ankle cuffs on and tells me to cook us breakfast.  We finish breakfast a bit before 9 o’clock and I work on straightening up my office.

My 10 o’clock orgasm is delivered by a very well lubricated hand and she doesn’t stop when I cum. I thrash in the bed until I’m exhausted and then Mistress feeds me a combination of cum and coconut oil from her fingers.  After each orgasm I am released and given something to do or we catch up on one of our TV shows.

At 12 o’clock I’m tied back in bed. Mistress uses her had again. It takes longer but I cum and eat it up again.  I’m sent off to run some errands with panties on under my clothes.

2pm - Mistress uses a masturbation sleeve. It takes me a while to get hard so Mistress applies nipple clamps. The pain makes my cock throb and Mistress forces another orgasm out of me.

4 PM - I’m having a hard time cumming so a cock strap and nipple clamps are added.  Mistress uses the Hitachi and is able to make me cum. She keeps it buzzing long after I cum and I am begging her to stop. 

6 PM - Mistress tells me to go insert a butt plug and head upstairs. Now she starts using the Venus 2000. This device can suck an orgasm out of guys that have erectile dysfunction and can’t get hard. It takes a while but a very uncomfortable orgasm rips from my body. This is starting to feel like torture.  I am instructed to leave the plug in.

8 PM - as I am about to head upstairs Mistress announces that I am done for the day. I am to remove my plug and we will start again at 8 am on Sunday.

I sleep very well, but also concerned about the next day.

I’d like to keep going but I also want to leave it a mental mystery. I do imagine there is a point where I can’t cum anymore.  I also imagine there is a point where I am having an orgasm, but since I can’t cum, the orgasm keeps going and doesn’t stop. I’m in heaven and hell at the same time. I’m pulling against my restraints because it feels so good, too good.  Cumming until I can’t cum anymore and still being forced to is an amazing fantasy of mine.

One other variation of my fantasy is not just orgasm overload but total overload.  Blindfold, earphones with white noise or porn playing in my ears. A gag. A heavy leather collar. Nipple clamps. A tightly laced corset.  Stockings and high heels. The e-stim plug in my ass.  I’m tied to the bed with the plug pulsing in my ass, the Venus stroking my cock and the Hitachi adding vibration wherever Mistress wants it.  For the next 4-5 hours, Mistress keeps the machines running.  Turning off and on. Changing the speed of the stimulation. Nipple clamps are removed and added back. The earphones are occasionally removed so that Mistress can fill my mind with things she knows pushes my buttons. After each orgasm, the machines relentlessly keep going. Making me scream in agony until the agony turns to pleasure again.

A boy can dream, right?

Now that I’ve got myself all worked up. I should stroke my cock through my panties to orgasm, but I won’t. I’ll post this and get to work.

Out Of Chastity - For Now

I've been too busy to post and am going to make this one short as I really don't have time now.

I am currently unlocked.  After 77 days (my 2nd longest lock up ever), we went on a trip, on a plane.  Mistress doesn't like me locked up on planes or in hotels as she likes easy access to my cock.  So far this year I have been locked for 171 days which is 2 days longer than last year, and we still have 4 months left in the year.

One thing that happened over the last 77 days is that my cock now seems to have a permanent upwards hook on the tip of my cock.  Best as I can tell, when I would get hard in the cage and my cock wasn't in the best position to get hard, it would bunch up at the end of the cage with the tip pointing up.  We're still doing some research, but it's likely this hook will reach Mistress G-spot even better.

So far I have had 2 orgasms since I have been unlocked.  The first one I was too excited in Mistress and I didn't have permission to cum.  I stopped long before I thought I was at the edge and my cock pumped months worth of cum inside Mistress.  While the orgasm was unfulfilling, being inside of her was indescribably amazing!  It had been so long.  The 2nd orgasm was much more fulfilling and I am looking forward to my next one.

I have also been able to edge again.  In the 12 days since I have been unlocked, I have edged 9 of these days a minimum of 8-10 edges each time.  If I had time right now I would be edging and possibly decide to go over the edge.

I have now had 9 orgasms, but only 5 authorized.  I absolutely love not having control of my orgasms.  I'm out of time and have to run.

  

Reflecting on Chastity

Today is my 60th straight day in chastity. If Mistress keeps me locked for another 15 days, I will have spent more time in chastity this year then I did all of last year.  If she keeps me locked up for another 33 days, it will break my old record of 92 days of being locked up.

Last July I had 3 orgasms, one of which was unauthorized when we went on a trip around our state. This July, zero. 

I’ve had 8 orgasms this year of which 4 were unauthorized and those unauthorized orgasms are why I’m locked right now. I don’t deserve to have access to my cock as I can’t be trusted.

Last night I managed to get Mistress to tell me that she has had at least a few orgasms while I’ve been locked up. I wish she would tell me when she does this because I absolutely love the mind fuck aspect of her being able to masturbate while I can’t. And that she can cum as much as she wants and I can’t cum at all. It’s a chastity slave’s biggest turn on.

I’m really, really wanting to pleasure Mistress with my mouth, my fingers and any toys we have.  I want to be close and intimate, give her pleasure and make her cum.  However, I also want to be needy, desperate, denied, locked, tortured, willing to do anything and addicted to my situation.  I fantasize about making out with Mistress, my hands all over her body, my fingers inside her, making her cum over and over.  My cock is completely ignored while Mistress pinches my nipples while telling me she has no intention of unlocking me any time soon.  The frustration of being so intimate and sexual with Mistress while I am completely denied makes my head spin.

So that’s where I am today. Locked, denied, frustrated, and loving it. 

Some captions that make me squirm...