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...

Things Running Through My Mind Almost Daily