Femme Dreams & Chastity

I am on my 50th day of being locked in chastity and it’s been 70 days since my last orgasm. Each day gets a bit more difficult, in a good way.

I had a few dreams this week related to chastity and feminization.  I had two dreams where I was somewhere barefoot and I was worried people would see my pink painted toenails. So I would walk with my toes curled under into the carpet.

In another dream I was fully dressed in a dress, heels, wig and a hat.

I was out in public and people started showing up. I have no idea why I expected privacy, but when people saw me I panicked that they would know I was a guy (I have a beard).  I took off my heels thinking that would make it less obvious.  It didn't.  The f

A few days ago I was released from chastity to do a device swap out before Mistress and I went to a meeting.  The thing is I didn't go into the new device immediately (I intended on locking back up at bed time).  When we got home from our meeting Mistress noticed my unlocked status and called me out for it.  I quickly locked myself up.  It's a huge on turn-on when Mistress either calls me out or gives me commands.  Having my chastity device acknowledged either verbally or physically is a huge turn on.  So are things such as my perfume, nighties, nail polish, etc.  Any sort of bossiness, bitchyness, attempt at humiliation or other form of acknowledgement makes me swoon.

Now chastity is not easy, but it can be very fun with the right attitude.     

Ready To Burst

It's been 64 days since my last orgasm.  I have been locked in chastity for 44 of those days so far which make it a total of 108 days I have been locked in chastity in 2018.  I have been locked up 5 days longer than I was in 2017 which was my oldest annual record.  I am 48 days shy of my record for being continuously locked up.

This is a pretty good depiction of my last orgasm

Needless to say I am an absolute horny mess.  I wake up in the mornings with my cock straining against it's cage.  My mind races with erotic, humiliating, painful, and nasty thoughts.  I dream of Mistress making me service her in multiple ways while I stay locked.  I dream of being dressed up and being her chaste feminized servant.

We've been very busy lately which has limited my posts a great deal.  It has also limited our ability to be intimate.  We were able to fit in a quick-y a couple weeks ago, but it was so quick and neither one of us came so it was essentially an edging session for us both.  While we were having sex Mistress asked me when I thought I should be allowed to cum again.  I said 'never'.  That was wrong to say.  The problem with never having another orgasm makes you forget how good they are.  It takes away the desire and the desperation since you know you will never have one.  Even if I was to never have another orgasm, I shouldn't know that is the intention.  Always believing I have the chance to cum makes the tease and denial that much more effective.  So how often should I cum?  It's not up to me of course, but I feel it should be a range.  Certainly I think I should have extremely long dry spells of 2,3,4,5 months.  I also think I should be forced to cum 4,5,6 times in a very short period.  To be tortured with orgasms to where I am brought to tears and begging Mistress to stop.

With all of this mental focus on cumming my mind has been going back to something I read many, many years ago.  The post was from a Mistress that denied her husband orgasms, but when she did allow them it had to be either non-pleasurable, humiliating, mundane or otherwise undesirable.  Of course that puts all sorts of ideas in my head.  Here are some that I came up with and some that I found online.

• Ruined orgasm
• Use Hitachi on chastity device to force orgasm. Ruin it if possible.  Don't unlock him!
• Made to masturbate in front of Mistress and made to lick up the mess
• Cum on Mistress shoes and made to lick it up
• Clean my cum out of Mistress pussy after orgasm
• Forced to cum into a condom and have it poured into my mouth
• After an orgasm, smear the cum all over the slaves face and let it dry.  Don't let them wash it off
• Post orgasm torture
• Make the orgasm hard to achieve (stand on one leg, use numbing cream, etc)
• Masturbate slave with icy-hot.  If he cums from this he is a real pain slut
• Cum on or in a sex doll.  Lick it up.  A male sex doll it more humiliating
• Have slave raise his legs over his head and make him cum into his mouth
• Use electricity to make orgasm painful
• Squeeze slaves balls as he orgasms and for a time afterward.  See how much cum you can squeeze out.
• Save cum for later
• Only let him cum when he has something in his ass.  He will soon associate the 2.
• Make him cum on a dildo and lick it off
• Prostate milking

All of that makes my cock hard.  Some of those things I wrote are things I wouldn't want done to me at the time, but I know damn well I would fantasize about it later.  Being in chastity sure make my mind more devious.

Now onto some obligatory pictures that have caught my attention lately.

28 days locked

Today is my 28th day in a row locked up and 47 days since I last came. We’ve been too busy for anything outside of our day to day so the enforced chastity is a good mind fuck.  My naughty mind keep going into more extreme fantasies. Some I’m a bit ashamed of, in a good way, that I would love to confess.

Here is a post that I was just reading that had my cock straining so hard against my cage I thought I would break it.  She has some great ideas.  Enjoy!

http://www.keephimcaged.com/post/179276041336/locktober-2018-21

Reading stories and getting worked up.

This morning I woke up very, very horny. I decided to find some stories that would get me even more ramped up.

Here is an excerpt from one of them on Literotica.

Good boy. Now crawl into our room and get on the bed doggy style." I did as I was told a little fearful of what was going to happen next. I waited on the bed with as I heard her walking into the room. "Now I want you to hold very still and relax." With that I felt a cold sensation on my asshole. I could hear the squelching of the lube she had brought in and then the intrusion as she sticks a wet finger up my hole. I gasp and rock forward but before I get to far she grabs my balls and pulls me back. "Did I give you permission to move?"

"No mistress. Sorry mistress." I feel something loop around my balls and being pulled tight.

"Now you can't move. I've just tied your balls to the bed so don't get any ideas." With that said she goes back to fingering my ass. I bit back a yelp at this intrusion and hope she gets bored soon. She then adds another finger and I let out a gasp as she runs the tips of her finger over my prostate. "Ooo somebody liked that didn't they. I'm going to make you a little ass slut. One thing I learned about were these things called anal orgasms. Apparently if you stimulate the prostate enough a male can cum just from that. So I've decided that for now that is the only way you will be cumming. And to top it off you will have to eat it all. She starts to fuck my ass rapidly making sure to stroke the prostate with each thrust. I begin to shake from the sensations and I suddenly feel a pressure disappear from me. I look between my legs and see a fluid pouring out of my cock onto a plate. She laughs in pleasure as she continues to pump in and out of my ass until the flow stops. She then pulls her fingers out and goes to wash her hand, leaving me sitting there shaking after my first anal orgasm. She comes back and pushes the plate underneath my face.

"Please mistress don't make me eat my own cum."

"Begging won't do you any good. You lost that right a long time ago. You are going to eat every drop on that plate and you will eat every drop that comes out of you for the rest of your life." She shoves my head down in the plate and all I can do is lick it up. It has a salty taste to it and I screw my face up in disgust but I finish it. She stands up and walks away leaving me tied to the bed. I'm afraid to move for fear of getting punished. My cock throbs in my cage over everything that has happened to me in the last few hours. She comes back a little while later and unties me. "Go make me dinner. I don't care what. Just surprise me."


ANOTHER STORY

Kneel just outside the glass door here and edge for me while I shower. I want you to count them out."

Oh Em Gee. She takes long showers; even on work days like today.

The first edge is while she washes her hair. Head tipped back, clearly luxuriating in the water cascading over her head washing the shampoo away. Of course it helps that I am a sucker for the fragrance it has. 

"That's one." I moan. 

She straightens up and wipes the water from her face and smiles at me. Clearly relishing my longing for her and my self-denial for her benefit.

The second is as she soaps her chest while smiling lovingly through the glass at me. I stop just short of ejaculating and huff a hoarse "Two." My cock twitching multiple times but fortunately not squirting. I timed it perfectly.

She smiles and wags a finger at me in mock scolding.

The third edge comes as she washes her ass, which is pointed at me. As she smiles down at me I swear she is spending far too long washing her anus with a finger. Is she actually sliding it in? I can't quite tell. "Oh god, oh god. Three" I gasp.

The fourth hits as she uses the shower head between her legs. Clearly giving herself another orgasm as I watch her and she watches me. 

"Are you ... getting ... close?" she asks.

"Yes" I moan. 

That she is watching me do this is so erotic. Through clenched teeth I say "Four" as I let go and grab my own legs and start gasping to keep from going over. 

She orgasms against the shower wall looking down at me. When she finishes shuddering she rinses and hangs up the shower head and shuts off the water.

"Hand me a towel for my hair"

I pass her the towel with the hand that hadn't been stroking my cock. She dries her hair vigorously. It makes her tits shake marvelously.

By now I am no longer fully erect, only a half mast. I am, however, on perpetual edge. It has been a minute of panting and handing her a towel since my last edge but just two strokes and I am right back at the peak "Fiiive" I croak. 

She stops drying and peeks out from under the towel and giggles at me. "Now dry me off."

I take the other towel from the warmer and wipe her down with its warm softness, drying her without actually being able to touch her. 

"That feels so nice" she says.

"Now... Be a good jerk boy and edge for me again and then hands off.

She turns and picks up her deodorant. She watches me in the mirror as she applies her deodorant. Next she picks up her perfume and gives two quick sprays. 

I let go just barely in time. "Si-hi-hi-ix"

She turns around and grasps my cock with thumb and forefinger and lightly rolls it between them. Once, twice, another edge. Good lord she can play me like a violin.

Coyly she asks "Is there anything else we should do before we lock this thing away for the day?"

I know the right thing to say "I love you. Please don't make me cum".

She closes her whole hand around my shaft. Slow and gentle she strokes. One, two, stop, another edge. 

"Really? After all that you don't want to cum?"

"No, please don't"

"No?" Stroke, stroke, stop. Another edge.

"Oh god, Please don't make me cum"

"Ok" She replies, with a half smile. 

She steps in close. The scent of her makes my head swim. My legs begin to shake.

"Kiss me" she demands in a whisper.

We kiss. Soft and deep. That alone edges me. 

I whine "Hmm Hmm Hmmm!" into the kiss and my knees start to buckle and my eyes roll up. She breaks the kiss and just stares at me.

I pant hard and fast. 

When my breathing steadies just a bit she leans in and asks "What do you say?"

"I love you. Thank you for not making me cum."

Placing a hand on my face she looks at me with a smile and movie-star eyes and says "I absolutely love hearing you say that. That is so hot and so sweet."

She turns and picks up the bra and panties from the hanger and puts them on. My head slowly starts to clear as I step back from the edge.

She picks up the cock cage and says "Let's get you secured for the day shall we?"

Locktober so far

As of today I have been locked in chastity for 15 days straight. That brings my total days this year up to 79 total days and still counting.  I need to stay locked for another 24 days to beat last years 103 days of lock up.  I would need to stay locked for another 78 days straight to beat my record of  92 days of being continuously locked.  That means I would need to be locked until December 29th to beat my old record.  The idea makes my head spin. Let’s say I wasn’t unlocked and allowed to orgasm until January 1st. That means I would be orgasm free for over 3 months and I would only have 11 orgasms for the entire year.   That’s a far cry from my 600+ orgasms a year I had when I was younger. If I stayed locked until Jan 1st I would be locked 159 days or over 5 months. The thought of that makes my cock even harder.

Since Mistress and I are busier than ever we don’t have much time for play or for me to be dressed up I am still thoroughly enjoying being locked and denied. Mistress is doing a good job of not making me feel ignored. She is however tempting me by leaving my chastity keys on her vanity. It’s much better when she hides them from me. So far the temptation is not too great.

Locktober Desires

While it’s only the 3rd of Locktober, I’m 6 days in at this point as we started early. In addition to being locked in chastity I am also warring my collar and have my toenails painted bright pink. Mistress seems really intent on keeping me locked up and pushing my buttons. That makes my head spin.

The last few mornings Mistress has gotten out of bed before me. This would typically be the time that I would stroke my cock and edge myself. Since I am locked that’s not an option and it frustrates the hell out of me. I’ve even tried moving my cage back and forth but quickly realized that’s pointless. When I get frustrated like that my brain goes into overdrive. I start fantasizing about being pushed further. Since I can’t get any stimulation on my cock I yearn for other stimulation, like my ass. Fantasizing about being able to cum from anal, but also knowing that it would likely only frustrate me more.  Thinking about being plugged and/or having my nipples stimulated or tortured as those are my other erogenous zones.

The longer I go without cumming (26 days so far) the more my feminine side starts to over take my thoughts.  Having my toenails painted and wearing nighties is just the beginning. I’ve been fantasizing about a long nightgown that would be difficult to sleep in.  I’ve been fantasizing about being fully dressed and wearing heels again as much as possible. I’ve been fantasizing about wearing a camisole, stockings,  clear mascara and tinted lip balm when I leave the house. I fantasize Mistress calling attention to my chastity and my femininity as much as possible as a way to erotically humiliate me.  Just last night she made an innocent comment on my toenails.  It made me very aware of my feminine self and I loved it.

Mistress and I will be going out of town for a few days. I’m packing a nighty that she loves to see me in.  I’ll be in chastity which will be unusual. Mistress normally likes to keep me unlocked when we travel together but I can’t be trusted in hotel rooms after she falls asleep. Ideally I will stay locked until we get to the airport and relocked after going through security. Or I can wear a plastic device that I’ve already worn through a couple of airports.  My mind is so ramped up right now I am fantasizing about staying locked the entire time, and also pleasing Mistress with my fingers and mouth every day.  The thought of staying locked while Mistress orgasms multiple times is one of my favorite fantasies.

In closing, I just wanted to say how much I love it when Mistress locks me up.  It’s not the chastity that I love, it’s the control I’m forced to relinquish. I also love it when Mistress keeps adding to my situation. This time it’s not just chastity. It’s my collar. It’s my toenail polish. It’s nighties again. The more she puts on my plate the more my head spins with desire. I’m a horny mess.

Apparently I’m so horny that I’m a bit of an exhibitionist today as well. These are all pics of me.

Addicted To Desperation

Last night I was in bed in my nighty waiting for Mistress to come to bed.  When she came into the room she told me to get some towels.  That's how she tells me she wants to be fucked and given a good orgasm or 3.  As I got out of bed I took off my nighty.  She told me to put the nighty back on, which made my dick swell.

I love having to wear feminine attire in front of Mistress.  I love the erotic humiliation.  I feel shame, but a the same time accepted, which makes the shame a turn on.  I love how being dressed makes me less likely to be disobedient.  I love being encouraged to wear something feminine.  I wish I could be OK dressing up myself, but I am not there yet. 

As I put the towels on the bed, Mistress told me that she didn't get a chance to read my post from that day.  She asked me what I wrote.  I told her I would tell her as soon as my cock was inside her.  Mistress was in bed and I got on top of her.  In no time, Mistress's hands were underneath the bra of my nighty and she was pinching my nipples.  As I eased my cock into her I started to tell her about my post from that morning.  I told her about LOCK-tober, NO-vember and DENYcember which is a thing nowadays with those practicing chastity.  I told her how this year I am running behind last year as far as my time locked up.  Mistress jumped on this immediately and told me that I would be participating in all 3 months of this unless we were traveling.  I assured her I can stay locked up while traveling as well. 

We continued to talk while having sex.  Mistress told me that I needed to start wearing my collar again.  She told me to get my toenails painted this morning.  She also told me that she soon would be tying me up.  All of this talk got me fucking Mistress hard.  In no time she had one of the strongest orgasms I have felt in a long time.  She squirted all over my cock and came hard.  It seemed like all of that talk was getting her going as well.

Mistress then closed her legs with me still in her.  This is the position she likes to tease me.  We continued to talk.  I told her how much I love it when she is mean to me.  When she hurts me.  When she makes me dress up feminine. When she locks up my cock.  Mistress then told me to cum.  I begged her to not make me cum.  I told her I would do anything she asked me to.  I told her I wanted my last 3 weeks of denial to still be with me.  I dreaded the idea of cumming and having to go straight into chastity.  I dreaded the idea that she might make me clean my cum up with my mouth.  Mistress relented and told me to get off of her without cumming.  I tried to stay inside her and enjoy the feeling I knew wouldn't be feeling any time soon.  Mistress told me to go put my device on immediately.

As I struggled to put my device on my still hard cock, my head was spinning.  It has been quite sometime since Mistress cared about whether or not I wore my collar.  I love wearing it as it's a constant reminder of me relinquishing myself to her.  I love it even more when she wants me in the collar.

I climbed back into bed, locked and still in my nighty.  I gave Mistress a series of kisses as I thanked her for the privilege of being inside her.  I thanked her for locking me up.  I thanked her for not letting me cum.  I assured her that she can do whatever she wants to me and I will love it, even if I don't at the time.

I had a tough time sleeping last night with my libido so high.  But it was exactly what I needed.  This desperation and desire is like a drug to me and I am addicted. 

   

LOCK-tober, NO-vember and DENYcember

In 2016 I spent 70 days in chastity.  In 2017 I spent 103 days.  So far this year, it's only been 64 days.  I need 40 more days to beat last year's record.  Here is my tracker https://missbossybitchsboy.blogspot.com/p/chastity-tracker.html

I had hoped to be in chastity for 365 days this year, but as usual, reality is different than fantasy.  Even if I was locked up the rest of the year, it would only be 150 days or 5 months total.  That would be hot.

While I haven't been locked, I have been much more faithful to my orgasm denial regiment.  Here is that tracker https://missbossybitchsboy.blogspot.com/p/history-of-orgasms.html

I have only had 11 orgasms this year and that includes my unauthorized ones.  Last year I had 21 that I admitted to and I am guessing another 5-15 that I cheated and didn't disclose.  My last orgasm was in a hotel pool 3 weeks ago.

All that being said, I have had increasing chastity fantasies.  That's when I am not fantasizing about being dressed in my feminine attire, which I do a lot. 

A couple weeks ago I dressed while Mistress was out.  I hate dressing up without being told to do so, but sometimes the urge is too strong.  I have a hard time with my feminine side without a bit of encouragement and preferably some coercion. 

Yes, LOCK-tober, NO-vember and DENYcember are a thing and have been for a few years.

If the tables were turned

I have been thinking a lot about how Mistress could be meaner to me over the last few weeks.  It's hard to be mean to someone you care about and want the best for them.  That got me to thinking.  What if the tables were turned.  What if Mistress came to me and said she was tired of being the dominant one?  What if she asked me to take control and to 'be mean' to her?  What would that look like? 

Now while I am submissive, I certainly have a switch side that I can call up when I want to.  If she wanted to switch places, I know I would be very, very good at it.  Here are some ideas of what I would do if I had control over her.

Every morning she would have to touch herself until her pussy was wet, and then she would have to start stroking my cock until I was rock hard.  Some mornings I would fuck her and other mornings I would tell her 'no' and to get her day started.

On days that she didn't have appointments, she would have a 'uniform' to wear.  I would requite her to wear secretary style clothes during work hours in our home office.  Heels would be required and stockings optional. 

Or even better.  A hobble skirt to make it hard to walk.

Throughout the day I would summon her to my office.  Sometimes I would have her do down on me at my desk.  Other times I would make her lift her skirt and show me her panties.  Other times I would just dismiss her.

On weekends I would have her wear a skirt as much as possible.  We would go out to and I would have her go into a bathroom, remove her panties and hand them to me.  Later I would give them back for her to put on.

She would have to wear a nighty every night and a long restrictive night gown would have to be worn on occasion.

Occasionally I would do something called "Power Hour".  It would be an hour that I showed her how much power I had over her.  The scene that sticks in my mind is one with her in the pillory in our basement.  

Once her head and hands were locked up I would spread her legs and attach them to the frame.  I would tell her she would remain in this position for the next hour.  At first I would just walk around and touch her.  I would smack, pinch, prod and do things to make her feel more exposed.  I would sit in a chair in front of her and stroke my cock.  Eventually her legs would start shaking from the stress of being bent over and spread out.  Then I would clamp her nipples and hang weights from them.

Depending on my mood I may give her multiple orgasms.  Other times I may turn off the lights and leave her in the dark, watching her from in infrared camera.  Other times I would put my cock in her mouth and force her to suck my cock.

I might change it up and instead of power hour, have contemplation time.  I would tie her to the bed, blind fold her, and put headphones on with white noise or porn playing in them. I might put a vibrator inside her and either leave it on really low or really high for as long as I wanted.  Other times I might put the e-stim in her and on her and have her randomly tortured.  Other times I might make her stand in the corner and make her contemplate her new found desire to submit.

And I would be remiss if I didn't say that the fucking machine would be put to regular use on her.

This is just a tip of the iceberg of what I can imagine doing to a needy desperate submissive (like myself) if given the opportunity.