"You get one come a month and one picture of me to obsess over"

The drive to see her takes three hours. I drove in total silence with the radio off. I had too may things swirling through my mind. I met her online and I sent the keys to my chastity cage to her. Once upon a time she was a cam girl, but was now "taking a break from that". Now, once a month, I would see her for “relief”, per our agreement. Knowing that I would be bare ass naked as soon as I walked through her door made my heart skip a beat whenever that thought crossed my mind.

I dressed nicely, but I wore my absurdly small black nylon bikini briefs. I hoped that she would like them, but I was leaking cock tears the whole drive, I felt myself getting sopping wet. No matter, they probably would not stay on very long. I have never gone without an orgasm a whole month before, and the entire month was an endless obsession over all things sex. I wanted pussy, I wanted breasts in my mouth. I wanted a blowjob, I wanted to cuddle. I wanted the freedom to stroke my own cock until come gushed out several times a day like I used to. All these things were denied to me for one month and my psyche was starting to unravel .

I navigated over to her townhouse, a nice place, but I had to park a block away. More time for my mind to go crazy thinking about what was to come. I knocked on her door, feeling like my heart was going too burst. I’m a respectable middle aged man. What am I doing here? “Submitting to a woman who owns my cock”, I thought to myself in response.

It took a while for the door to open. 

"Well hello there! Good to see you!"

I've seen pictures of her, of course, but seeing her in person felt like getting punched in the chest. I knew it was coming, but I felt overwhelmed anyway. Half my age, long brunette hair and elegant features. She wore a simple little black dress. Of course, I noticed that her dress had those horizontal stretches between her nipples because it was just a bit too tight. "Nipple Ripple" is the name for i think. This woman knows how to tease.

“Did you find the place ok?”, she asked very sweetly. 

Then without waiting for an answer, “Disrobe slut” she said calmly, easily switching gears to dominant mode

“Yes Miss Katie” I said. She prefers to be called Miss Katie. And then I immediately did just that. I slowly peeled off my bikini briefs and I saw a smirk grow on her face as I approached nudity. I was soon surrounded by a pile of my own clothes and I began to feel very naked, very vulnerable and not quite believing that this was happening.

I fumbled around trying to arrange my clothing into a neat pile. I realized that it is impossible to look cool when you are a naked man in front of a beautiful woman and wearing a chastity device. I suddenly felt a little cold, the noticeable feeling you get when you are bare ass naked.

Avoiding eye contact, I meekly placed an envelope containing two hundred dollars into her hand. Not much, all things considered, just enough to compensate her for her time. She took the envelope from my shaking hands. I just realized they were shaking! So not cool. 

“Thank you for the retainer fee” she said. It was not payment or tribute, it was a retainer fee. She is a smart girl with a college degree.

“Did you have a nice month in chastity? Did looking at my pictures the whole time make your balls want to explode?”

“Yes Miss Katie, I was miserable, but I never felt so alive.” She sent me many photos during the past month, all of them non nude selfies, but wearing the barest of things.

She disappeared out of the room for a minute. I glanced around and saw artifacts of a normal life, pictures of her with her friends, her family, some retro movie posters. Her cat sat nearby, completely disinterested in me.

She returned, but this time in a sheer black bra and panties. I twitched all over as I noticed a little tiny bit of her hair showing through her panties.Not much, just a little. So classy.

She made those long strides that only girls with long legs can do. I was hypnotized and completely under her spell at this point. I stood with my hands at my sides, not knowing what else to do.

“I picked out this bra and panty outfit just for you. As you know, I don’t get naked in front of slave boys. Nothing personal my slut, it’s just protocol.”

“I understand Miss Katie”.

“Well, are you just going to stand there?

I fell to my knees and started to beg.

"Beg me for permission to jack it!”

“Please Miss Katie, can I please come?

"Wait, you want permission to masturbate, or permission to have an orgasm? Get your story straight. I think you are getting greedy with me.

“Oh please Miss Katie…” was all I could utter. My mind was not operating in a coherent manner and I started babbling with my forehead and elbows and knees on her cold hard wooden floor, my ass shamefully pointed upward.

“OK, you may stop begging. Now look at me”.

She flicked her hair and smiled. Her white teeth lit up the room.

“OK boy, your sheer sluttiness has amused me.”

She took the key to my chastity cage and walked forward to me. At this point I noticed her hair smelled like flowers. and I trembled at her closeness to me. I was mildly disappointed that the chastity keys were on her key chain rather than a necklace or anklet, but I removed that thought from my mind. It was replaced by, “My God, her hands are near my penis!”

She turned the lock and slipped it off my cage. Immediately my cock began to grow, it was noticeably dented and purple from being half erect in it’s cage for the whole drive. The top half of the cage itself was stuck to the head of my cock as it grew, a detail that made her giggle. She then snatched away the cage and left the base ring of the cage right where it was. 

“Still five inches I see. Oh well, I don’t know why I was expecting it to get bigger.”

She then stood with her hands on her hips and feet lightly apart. The "Wonder Woman" pose that she knows I like so much.

"OK, now stay on your knees. Now give yourself the highlight of your new sex life. Do that thing only loser boys who can’t get laid do. DO IT! "

I began to meekly stroke, with one hand only.

“Use both hands, make some moaning sounds. Fuck your hands like the male whore you are!”

I started to pound my little cock with both hands and bucked my hips, my knees were hurting from her hard wood floor and I started to make some sounds that must have been comical to hear. I realized I was making squishy sounds as I fucked my hand. I focused on her face and made eye contact. 

“Don’t look me in the eyes while you do that, it’s unattractive. Maybe I can make my nipples poke through my bra. You like that, don’t you? See I remembered!” 

She began to twist her nipples through the thin fabric of her sheer black bra, and within moments her nipples began to poke through, enough to cast little shadows, a detail my overworked brain picked up.

Oh Miss Katie, I think I’m going to…“ I couldn't even complete the thought…

"Slut, I have decided that you may come. But please don’t come on my floor, lean back and come all over yourself."

I noticed with some clarity on how the small of her waist made a perfectly proportional V shape leading to her hips.

I was ashamed at myself. I barely lasted a minute, but it was a whole universe in a minute. She laughed, it was exactly what she expected to happen. 

"Freeze. I want you to stay in that position for a little bit."

She walked around me, her heels loudly clicking on the hard wood floor as she walked around me. I was still on my knees, leaning back with my come covered cock in my hands.

"My my, I have a naked ugly man with a little dick in my house, What ever shall I do!"

She kept me like that for a full minute and she started to laugh. I could tell it wasn't a fake laugh, she was really amused.

"Now, was that the best sex you ever had?"

Yes Miss Katie, it was and I am grateful!"

"Aw, you would rather masturbate in front of me once a month than have any resemblance of regular sex. That's so pathetic. But it's also rather sweet.

"OK, now put your clothes back on, but leave your pants on the floor and cock out, I want your cock cage to be reattached before you leave”. 

I dressed myself, feeling dirty and squishy from my own come still all over my belly. Of course I felt ridiculous standing there with my pants down and my wet cock hanging out.

“Would you like to see a new photo of me before you leave?”

“OH YES Miss Katie” I said, louder than I meant to.

“OK, that’s fair, you’re a low maintenance slut, I can allow that. Just remember when my boyfriend is railing me with his big dick, you’ll be looking at those phone pictures while your dick is locked up and I hope it makes your balls explode.” 

Making “my balls explode” was a phrase she used a lot. She must like it. I like it too.

“I have some homework for you. You are too old for me, and you have a small dick, and you are not particularly handsome. But for a man your age, you look OK naked. But OK is not good enough. I want you to actually look good naked. Next month I want you here at least ten pounds lighter. And work those biceps and forearms. And trim your hair, it frames your face better.” 

“Yes Miss Katie, I will”, I said. And I meant it. My less than optimal appearance before this goddess was inexcusable.

She leaned over and placed the cock cage back onto my penis, I was still half erect and she had to fight it, but she won. She giggled. And I noticed how long her eyelashes really were. I decided that It was worth being a cock locked submissive slut just to be that close to her.

Click.

Locked.

“Ok boy. I took a little selfie of myself a few minutes ago and sent it to your phone. Congratulations boy! You earned a little privilege! You earned seeing me naked. Not in person yet, that might come later, but now you have a real photo of me getting a little naked for you. Don't you feel a little bit special?" 

"Oh yes Miss Katie! Thank you so much!

Oh of course she sent the new photo to me AFTER I was locked back up. So devious.

She sat down and crossed out her long legs, casually displaying the kind of legs that makes men wreck their cars.

“Go ahead and take a long good look at the photo I just sent. 

I did and my heart pounded. MY GOD what a great photo.I had no idea her boobs were that generous. She hides them well in regular clothes.

"I want you to know that after to leave, I’m going to fuck myself with a dildo twice as big as you. Your sexual neediness actually made me a little bit wet. Isn't it worth all that time locked up in chastity, knowing that makes me a little bit wet?”

“Yes Miss Katie. And thank you for the opportunity to masturbate to orgasm and thank you for granting permission.

 "And I know we agreed to one come per month. Once we really get rolling, I think I'm going to dial it down to 10 a year. Ten supervised mastubation orgasms per year is PLENTY for a man your age."

My heart skipped. Once a month was making me sleep badly and sending me into a spiral of perpetual lust. Taking two a year away suddenly seemed like a BIG deal. But I knew what I had to say.  "Yes Ma'am, ten is more than I deserve!"

"Glad you agree. Now good bye slut. I know you like being called slut. That is your new name from now on. SLUT. See you next month, SLUT”.

I walked outside and closed her door. And I immediately noticed that I reeked of my own semen. I am such a slut. A needy dirty male slut whose life revolved around masturbating in front of a young woman who will never touch me. And I suddenly felt lucky. I was lucky to have such a goddess as my keyholder.

I drove home, another three hour drive. In total silence again. And despite having been allowed to have an orgasm only a short time earlier, my cock began to leak and grow inside it’s cage. I thought about the new photo she sent to me. And I knew I would be obsessing over that one photo for the entire next month.

And it felt like my balls were going to explode. This is going to be a long drive home.