Two of those months locked in chastity, my cock compressed to half its normal size, caged and secured to a ring behind my balls that ensured a boatload of pain if I tried to get the device off.
The urethral insert worked wonders, along with the more severe compression of my cock to a smaller size, and the tighter ring behind my balls. Combined, it was clear I wouldn't slip out of this cage. I could cut it with wire cutters, big heavy wire cutters, maybe. Even that would risk damage to my scrotum.
I didn't try. I accepted my cock was locked up and I was being trained by Ash to control my erections and orgasms, just as I was training to build my body up.
The effects of my injury were long gone, but I continued to go to Ashley as a personal trainer.
It was a weird feeling when I thought about it. I had given Ash control over my body. Control over not just my exercise, but I was obeying her, letting her control what I ate, how I exercised, and my sexual behavior. She was my keyholder in more than one way.
My social and dating life had always been active. I didn't have a girlfriend, the last one had left in a huff six months before, but I'd dated a couple of women when the accident happened. After I got back on my feet, I tried dating again.
My first date in a few months; a nice girl named Melody. Cute name. Cute face, too, not great looking but nice enough and she had a body to die for. She worked out, ate right, and looked amazing in a tight club dress.
We had a lot of fun. We went to dinner at a club, and then danced and drank and then walked on the beach. That's where I kissed her, and she was into it. I think she liked me, and the kiss was followed by holding hands and then kissing some more, passionate kissing with tongues and lots of saliva exchange.
My cock was trying to get hard, but the cage held it in check. I could tell it was bulging between the cracks.
That's when Melody's hands went to my ass, pulling my hips toward hers. We were standing next to my car, kissing before we got in. All was going well and she was sending signals she wanted to go back to my place.
Her hand was squeezing my ass and pulling me in to her, all signals were go in my mind.
Then her hand roamed from my ass to my crotch.
She was feeling for my cock, through my heavy denim jeans. She probably expected to find a nice, erect member hiding in there, given the way she was pressing up against me. In fact, normally at this point my cock would have been trying to burst through my pants.
But I was in training. Under Ash's control. She had determined I was to have no erections without her permission.
What it did find was something hard. Like, something made of metal. The cock cage. Small, but definitely there, and not something she was expecting.
Everything came to a screeching halt. The kiss stopped, she pulled back slightly and her hand pressed my crotch a little harder, feeling the metal cage around my cock.
She looked puzzled, and kept feeling around, trying to understand what she was feeling. I could see her mind working.
Does this guy have a disability? Wait, maybe her underpants are in a bunch... no, that's metal. What do guys wear that is made of metal down there? There's his balls, but where he should have a cock is this hard metal thing...
How stupid could I have been, to allow things to go this far? Of course I couldn't have sex with Melody. I couldn't even masturbate, much less have sex!
My cheeks flushed with embarrassment. It was dark so she probably couldn't see me blush, but both our demeanors changed. It was like a huge bucket of ice cold water had just been dumped on both of us.
"I... uh... should probably take you home," I said, fumbling the words.
"K." she said, not really understanding anything yet, but realizing something was wrong. She probably felt she had stepped over some boundary with me and done something wrong herself, and yet she was incredibly curious as to what was going on between my legs.
We drove in relative silence. When we got to her place, she gave me a peck on the cheek, said she'd enjoyed the evening, and was gone.
I went home and threw a lamp against the wall, then went to bed and cried. I would have masturbated but... I couldn't.
The next day I showed up early for my training session with Ash.
Ash nodded, a slight smile on her face. "Yes, being in chastity means, well, you are forced to be chaste. You can date, but no sex. That's the way it is."
"But, but... this was supposed to just control my embarrassing erections in the gym and to keep me from masturbating too much! This thing is going to fuck up my ability to see women at all!"
Ash shrugged. "Michael, it is chastity. It's not some game. It's you being chaste. Controlling your urges. Having your ability to engage in any sexual activity restricted. Period. Masturbation, fucking, whatever."
"I am your keyholder, and I decide. Now, if you want permission to have sex, you can always ask me ahead of time and I might approve it and allow it. But it isn't something you get to decide for yourself. Not while you have a keyholder."
The full impact of what I had done with Ash was now hitting me. She literally controlled all my sexual activity. In fact, as my physical trainer, she had gotten to the place she controlled most of my physical activity, including exercise and diet.
"Look, I understand you are frustrated. Perhaps it is time for a milking." That's what Ash called giving me a hand job and some relief from being locked up.
Just being in front of Ash had gotten me aroused, even though I was still frustrated. I agreed. A milking.
Ash got out the lube and jar of my semen collected over the last few weeks (it was frozen, and I added some each time she milked me). I dropped my pants.
One of the weird things about the current model of chastity cage we were using was the rather deep urethral tube. It was semi-rigid and went deep inside, back behind my actual cock when I was in chastity. When she removed the cage and I got erect the tube went back the length of my elongated cock, but no further.
Ash always left that tube in my penis, even when milking. She'd sometimes move it in and out, up and down, using it to stimulate me and help me cum. But she didn't remove it.
The lube and removing the cage had already stimulated me to the point I was ready to cum. It had been a week and I was soooo ready. Ash started stroking, at the same time pulling the urethral probe in and out. My cock was getting jerked inside and out and I couldn't last more than a minute.
My orgasm came fast and hard. I grunted loudly, almost cried out, it was so intense.
"Oh, fuck! Fuck this!" Ash yelped, letting go of my pulsing cock, which was still in the process of pushing as much semen out as it could. The cum continued to splatter on her, even as she moved to get away, but she was sort of trapped between me and her desk.
When I was done, Ash had several ounces of my semen splattered over her top. Even some on her face.
"Disgusting... ewww... you got is all over me!" She griped. "Dammit. I don't have another top, either!"
She was using Kleenex to try and wipe the slime off her top. It succeeded in smearing it around, but didn't really get all of it off.
"Um... you have some... on your chin..." I said hesitantly. I didn't know what trouble I was in. She seemed upset.
"Oh fuck..." she wiped her chin, then her face, and returned to her top as I watched.
In spite of being in trouble, and having had that orgasm ruined halfway, this was really exciting and satisfying. It was the first time I'd ever seen my cum on Ash. It seemed like a giant step forward in our relationship. I'd actually ejaculated on Ashley, my keyholder, the woman I had the most massive crush on.
"Dammit," Ash continued to grumble, cleaning herself as best she could. "That will have to do. We need to put you into more controlled circumstances, maybe. No more ejaculations like that one. You must have been really frustrated about not being able to fuck your girlfriend, though?'
Ash snickered just a little as she began putting my cage back on. This was my second favorite part of my whole relationship with Ash-- the part where she manhandled my cock and balls, pulling, pushing, prodding as she got the cage back on.
"Wait... Ash, will you give me permission to fuck this girl? My date, Melody."
"I don't know, Michael. When are we talking about? Do you have a date lined up? Is it assured she will sleep with you?"
That stopped me cold. The date with Melody had gone well, but ended badly. There was no guarantee she'd date me again, and even if she did I couldn't tell when or whether she'd be willing to go to bed with me and fuck.
"That's what I thought," Ash said, reading my face. "Now, if you actually get yourself a girl lined up reliably, maybe we can make an appointment for a couple hours before hand and maybe, just maybe I will let you out of your cage. We shall see. Until then, you stay locked up."
This whole episode really made me aware that I had turned over a lot to Ashley's control. It wasn't just control over embarrassing erections at the gym; it was complete control over my sexual activity. And thus, significant control over my dating, romantic and love life.
I called Melody that night, and she was evasive and didn't want to go out. My chances there were ruined.
Sitting at the table looking at the salad I was eating (dinner defined by Ash, as most of my food was these days), I realized my main romantic and social contact was now my personal trainer. I'd given myself over to her in so many ways. She was defining my physical activities, my diet, and my sexual activity (or lack thereof). This in turn restricted my love and romance life... to just Ash.
Ash, as my keyholder, was becoming the focus of my emotional and sexual life.
Which sort of made sense. I'd had a huge crush on her from day one. I mean, why else would I have allowed her to lock up my cock and balls in this thing, and why do I let her put me back in it every time she milks me...
And why did I have her milk me? By which I mean, give me hand jobs, because that's really what it is.
Was Ash my woman? No, definitely not, in the sense I knew she had two keys on the chain around her neck, which meant she had another guy she was keeping locked up. Hmmm... that just meant she wasn't monogamous. Though I was sure as hell monogamous. Ash was the only person I had any kind of relationship with, and as long as she held that key, that was enforced.
I felt my cock and balls, trapped in the metal cage. It gave me a sense of safety, of belonging, to know Ash was in charge down there. In fact, feeling the hard metal between my legs gave me a sense of belonging. I belonged to Ash.
That was good enough for me, for now. Forget Melody. Ash was my lover. Ash was my girlfriend. Yeah, the relationship was weird, maybe not entirely mutual, and definitely kinky, but that was OK.
I determined I would ask Ash out sometime. Try to expand our relationship outside the gym. Honestly, I thought I had a chance with her. She was my keyholder and masturbatrix, after all. We were already intimate ... in a rather kinky, weird way.
