Control: Dating Ashley

It took two weeks for me to build up the nerve to ask Ash out for a date.

My cock was locked up the entire time. Two weeks is the longest I'd gone without relief, and I was worried. I'd given up on dating, my relationship with Melody had come to a screeching halt and I'd decided I would focus on Ash. But that meant accepting her decisions about when she'd allow me to cum.

During that two weeks Ash had focused on me more, and it felt good. The attention, I mean. She put me on a more rigid discipline of exercise and diet. My physical therapy needs were basically over, and she shifted our emphasis to cutting down the amount of fat on my body and building up muscles.

Making my body leaner and harder. That was OK with me, though Ash really pushed me hard. 

Implicit in all the work was the idea that if I did well, she'd let me achieve and orgasm. In fact, at one point she actually said that.

"You are working really hard, Michael and I am proud of you. I think I might let you cum soon. Just focus on your diet more, I want one hundred percent compliance there. And trust me, I can tell if you cheat. That spare tire around your waste won't lie."

So I did. I threw myself into Ash's regimen, both to please her and in hopes she'd let me take off the cock cage and I could have an orgasm (or two).

It was a Wednesday, after my workout she supervised, when I finally asked her out.

Ash was pleased with my progress and it emboldened me.

"Michael, I am happy with what you are doing here. I think maybe it is time you cum for me. Maybe tomorrow, before you work out? Come a few minutes early and we can take care of you in my office."

"Actually, Ash..." I started a little nervously. "I was thinking, um... you know what would really make it special for me and be meaningful? If maybe you and I were to go out together and have dinner at The Sunshine Company. That new place that specializes in sustainables? Then afterward we could, say, maybe go to your place and you could do me, you know, give me the reward. That would raise my excitement level so high... um... I..."

I trailed off. She was looking at me with a funny look.

"Why Michael," Ash said. "You are asking me out on a date!"

"Yeah," I said, embarrassed. Ashley outclassed me and I suddenly realized it had been dumb to ask. 

"OK," she said, and I had to remind myself to keep my mouth closed, as my jaw wanted to drop in amazement. "But understand something. You and I are not in some sort of traditional romantic relationship. That isn't going to happen. I am your keyholder, and I will spend a little more time with you outside the gym, sure. But it has to be on my terms."

I nodded quickly. "Of course," I said. "Anything. I'd just be really happy to be able to spend some more time with you."

"OK. Then you will have to understand that on our date, I will be making the decisions. I will decide when and where. You will defer to me and my decisions the entire time. Is that understood?"

I nodded. "Yes. That would be great, actually."

It actually felt sort of good not to feel like I would be the hook to make sure the date went well. 

"All right then. We will be going out Friday night. Pick me up at my place at 6:00 pm. Screw the Sunshine Company, we are going to Fleming's Steak House. If, and I do mean if the date goes well, then you can have an orgasm afterward."

I was grinning from ear to ear. Ash had said yes, and her terms were just fine-- I was happy to let her make the basic decisions, it meant I knew she'd be happy with the date and I didn't feel the pressure. 

Ash told me exactly what to wear for the date. Slacks with a button up collared shirt and tie, but a casual sport jacket. I shined my shoes before hand, though she didn't ask for that. I picked her up exactly on time.

She looked fantastic.

I mean, until that moment I had only seen Ash as a personal gym trainer wearing tights or bicycle pants or sweats. This time she was wearing a black dress with black nylons and looked casual and yet somehow incredibly elegant all at the same time.

It blew me away.

Simply being seen with her in public made me grin and feel like a million dollars. I swear, people turned and looked at us. I knew she outclassed me, I am only an average looking guy and I was walking along with a gorgeous woman that has a high end supermodel body wearing elegantly tailored and perfectly accessorized clothes.

I looked down at what I was wearing and realized that while I had dressed the way she demanded, it was still not up to par. Too late now.

The date actually went reasonably well. It turns out Ash is incredibly smart; she has a history degree with a minor in English Lit. We talked about all sorts of things from current events to history to some of the latest medical advancements. She also has an amazing sense of humor.

Ash ordered drinks for both of us, martinis. I don't like gin that much, but Ash didn't bother to ask and simply ordered the drinks, so I drank it. She also ordered the wine. A rather expensive bottle, one that paired with the Chateaubriand she ordered for us.

I made no decisions during the entire meal; she ordered the drinks, the wine, and the dinner with the side vegetables.

During dinner she also reminded me of my special diet, instructing me how much of the meat I could have (three ounces) and informing me I could only have one tablespoon of the scalloped potatoes. I obeyed of course. Just being on a date with this stunning woman was enough for me. If she'd told me to eat rat droppings, I would have gladly.

My cock enlarged several times during the dinner. Just being closer to Ash and feeling her presence was getting me aroused and my extremely tight cock cage was simply not having it. It was uncomfortable, a reminder that this woman had control of my cock and my sexual behavior. Complete control I had given her freely.

Being reminded of that fact made me hard again. It was a vicious cycle.

After we shared desert the waiter came by (he had begin simply addressing Ash whenever he approached the table, as she was clearly making all the decisions), and put the bill down. Ash gently moved it over to my side.

I picked it up and looked. And almost gagged.

$537. Dinner for two. Drinks, wine, dinner, a shared desert. I had to add tip on top. 

"Tip him 20%," Ash gently admonished me. That was over a $100 tip. That was more than I normally spent on a date's dinner in total. But I pulled out my credit card and paid.

Ash patted my lap, feeling my metal cage briefly and said, "good boy."

That made me feel slightly better, but the size of the bill left a giant hole in my wallet and an ache in my head.

I had done one thing that night that Ash had not determined and instructed. It was my own idea, I got her a rose.

She accepted it with grace, smiled brightly, then informed me that it had thorns and she was disappointed in it.

I hoped she appreciated the thought anyway, but it did remind me that with Ash, I needed to make sure I tread carefully. She had made it clear that if we were to date, it was based on her criteria and rules.

Based on our relationship, which had been primarily professional and rigid, I didn't think Ash would be open to anything after dinner.  Like, she wasn't going to invite me over. I was locked up anyway and I doubted she'd just unlock me and have sex with me. 

I was right. Ash had me drive her home. I got out of the car in front of her townhouse and walked her up; she liked that kind of thing. At the door I waited patiently. Nervous as heck. I still couldn't help but hope she'd invite me in. She fumbled for her keys, opened the door.

At least kiss me, I thought to myself. I spent a lot of money on a date, and the least you can do is kiss me...

"Thank you, Michael. See you at the gym on Monday. Make sure you stay on your diet. On Monday we are going to start in on strength training for real. I want to see that body of yours get hard."

She smirked, we both knew there was one part of my body that wouldn't be getting hard.

And she closed the door in my face. No kiss. 

At home that night I broke a lamp and a mirror. My frustration with wearing the cock cage was extreme. But it wasn't as extreme as my desire for Ash and being so close to her, on a date, and not even being able to get an erection. With any other woman, in that same situation, I would have expected a night of debauched sex. With Ash I got "Thank you, stay on your diet".

The next week with Ash was just back to normal, except she was getting more intense in her requirements. 

"Michael, I want you to use this food diary from now on. Write everything you eat or drink in here, including something as simple as water. I will ask for it to check it at random times so make sure it is always up to date."

Ash handed me a small booklet. It was clear I was expected to do this so I accepted the booklet and nodded. "Yes, Ash. I'll keep it up to date and accurate."

My diet was strictly regulated. It was a good diet, I have to admit. Lots of protein, healthy, designed to get me into shape. But she became extremely strict with it, questioning me and making sure I strictly followed the diet.

My exercise routine became more intense as well, moving from rehab to actual health and body building. More weights, lots of running. 

Ash actually said it at one point. "I am remaking you, Michael. I can create something out of you, turn you around and make you something good. Just allow me control, and you will see the results."

Ash wants control over me, specifically so she can make me into something new and improved. At times I think she thinks of me as her doll or possession. A sculpture to mold and create according to her will. I am doing it because, well, I want to be close to Ash. I like being around her and like the attention she is giving me. Her having control over my body is somehow satisfying in a very weird way.

The effect of her regimen is clear, too. I am getting leaner, more muscled. I'm actually proud of myself. Giving Ash control is having a positive effect.

One day I might actually be able to lift weights as heavy as Ash does. Then she'll respect me.

Really though, I just wish she'd allow me to cum more often. 

I convinced myself that the more control I gave Ash the more she would appreciate me, like me, the better I would be as a man, and the more she would be willing to spend time with me. The closer we would be.

I asked her on a second date the next week. She said OK. Actually, she specifically said, "Well, as you have been following your diet relatively well and working out as instructed, I guess maybe you can have a break. Sure. We will go to Fogo de Chão. You can dress more casually this time. Pick me up Saturday at 6:00. Make the reservation for 6:30."

It had been three weeks now since my cock had been temporarily unlocked and I'd gotten any relief. Ash had not seemed to be inclined to give me any relief since then. Going out with her again... I was either going to come away ten times as frustrated, or maybe convince her to give me a little private time and an orgasm.

I dressed as instructed and picked her up. She looked amazing, as usual. Outside of the gym she had this aura of elegant sensuality that got me excited.

I could feel my cock expanding and being stopped in its cage. It did this periodically, it would begin to become engorged and expand but be stopped by the cage. As it got larger it became more uncomfortable and eventually the erection would subside. Being around Ash made that more difficult, but I tried to simply focus on making her happy and less on my own sexual urges.

That helped some and the erection relaxed though it came back at various times during the evening. Each time I simply focused on doing something to make Ash happy and stopped thinking about myself and my urges.

The evening went well. We talked and flirted, and it seemed like Ash was having a good time. She ordered for me again, and pretty much determined where we would go, what we ate, drank, everything.

Ash is really smart, and funny, and the more I was around her the more of a massive crush I got. Originally, it was because she was gorgeous, but more and more it was because she seemed like the perfect woman.

A perfect woman that knows what she wants, and likes to get it. As long as I gave her want she wanted, things went well. There was one point where I suggested we get a different desert, and sort of pushed; I saw the flash in her eyes and her serious face and it was scary. I backed down immediately and we got the creme brulee, just as she had wanted. 

All was well then.

In other words, as long as Ash was in control and getting her way, things between us were fine and she was happy and that made me happy.

As the evening reached the end I began to think more and more about wanting to get my cock cage off. 

As we were leaving the restaurant, I decided to go ahead and mention it. My stomach was tied in knots as I got up the nerve.

"Um, Ashley... I... was wondering if maybe tonight we could go to your place and maybe you could, um, well, it has been three weeks since I've had any release. You know. My chastity. Could we... what do you think?"

She looked at me sharply as we stood outside the car.

"I certainly hope you aren't suggesting that I might fuck you," she snapped at me.

My eyes went wide and I shook my head, putting my hands up. "Oh, no. No... no. Of course not." Down deep I might have thought that but clearly it was out of the question. "Just... you know... my cage off, a little relief like we do at the gym..."

She looked at me with disgust, eyes going up and down my body.

"Get in the car. Take me home," she commanded. I did as she demanded.

We didn't say a word during the drive back. She stared out the window, not saying anything. I wanted to sink through the seat down through the ground and disappear.

"Pull in right there," she said. "In that spot."

It was a guest spot at her condo complex. I parked, turned the engine off and went around to open her door. At this point I figured I was going to drop her off at her front door and get a "thank you" like before. If I was lucky.

When we reached her front door she took out the keys, opened it and entered. Once inside she turned around and said, "Well come in. You asked for it."

My hopes went up, I entered her house and she closed the door. I was inside her condo. Alone with her. This was a huge step forward. My cock had started to engorge again and was bulging between the wires of the cock cage. I tried to stay calm.

She led me in then turned to me.

"A couple of things I want to make clear. We've had a couple of nice dates. But understand something. I am not going to let you insert any part of your body inside of my body. OK? Do you understand that?"

I nodded. "Yes," I said in a husky voice. I didn't know what was going to happen, and the details of what she had just said weren't clear. I didn't actually understand, I think my arousal was too intense.

I followed her back into the bedroom.

"Strip," she ordered.

I dropped my pants, exposing myself. It's what we usually did.

"No, no. I said strip. All of it. I want you naked."

Oh. Things weren't happening the way I thought they would but still, something was happening. I was getting naked in Ashley's condo and that was more than I had ever dreamed. One step at a time.

With all my clothes off, including my watch and ring and socks and everything, I felt cold and vulnerable. Ash had not removed one item of clothing. It felt so unbalanced. At the same time my cock felt like it was about to pop it was trying to engorge itself well past what the cock cage allowed.

Ash inspected me. She checked the tightness of the back ring, and for any signs I had tried to remove the cage. It had a urethral insert that went far back behind where the penis extended from my body, making it impossible to remove without actually cutting off the damn thing, but she checked.

"You are clean, that's good," she said clinically. "OK. so I think it is time to introduce some level of discipline into the project,."

"Discipline?" I asked. "Um..."

"You will see." She pushed me back and I went back onto the bed, falling into a sitting position, laying back and supporting myself on my arms.

That's when I saw the riding crop.

"Ooowowwww.... fuck...." I cried out as the whip came down on my bulging testicle sack. It was clearly protruding from under my compressed cock inside the cock cage, and pushed up and out by the back ring. Perfect position for getting swatted.

"Move your hand," Ash said in a commanding tone. I had automatically covered my sensitive gonads.

"OOOWWW.... fuckfuckfuck..." I cried out again when the whip came down. "Why... ASH! Why are you doing this?"

"Michael, it is time you understand your role in this relationship better. I decide when you get unlocked. I am in control of your orgasms. I am not in the mood to listen to you begging for your sexual pleasure after a nice dinner out."

She whacked my balls again. It never occurred to me to ask why I was letting her do this, but I was. I could have just gotten up, gotten dressed and left (at least I think I could have). Instead I was laying there on her bed letting her hit my balls. I was actually spreading my legs to allow her easier access to my balls. To hurt them.

"You want an orgasm? You want me to provide a hand job? This is the price. The price for ruining a perfectly good date with your whining. The price for an orgasm. Pain for pleasure, Michael. Pain for pleasure."

She continued whacking my ball sack with her riding crop. I yelped with each strike. The pain was terrible, and after the first few strikes it started radiating out to encompass my hips. 

My stomach was getting nauseous.

I couldn't help but roll away. She was striking me, hurting me, with a regular rhythm. Whack. Whack. Whack.

To get me back under control she grabbed my scrotum. Her hand wrapped around my ball sack and squeezed, making my balls bulge out. She then was able to strike my balls directly, even if I jerked and rolled around. She controlled my testicles and made sure she could hit them precisely.

"Please..." I groaned.

"Please what?"  *Whack*

"Please hit me again, Ash?" she pushed.

"Please stop..." I moaned. Why wasn't I just getting up and walking away?

"Wrong," Ash said. *Whack*  *Whack*

"Please... hit me again," I asked.

"Better," Ash said. *Whack*

"Beg for it." Ash said again, waiting.

"Please... hit my balls again, Ash," I begged. I loved having her hand on my genitals in spite of the fact it hurt like hell. 

*Whack*

"You may have an orgasm now," Ash said. "Get up on your knees, hands and knees. Spread your knees."

I did as instructed. She unlocked and carefully removed the chastity device, sliding the long probe out of my urethra (it felt so strange to have it out after three weeks).

Grabbing my cock she began jerking me.

"Oh... fuck..." The pain in my balls was gone in an instant as the sensation of my free cock expanding unfettered grew with an erection that was as hard as any I had ever experienced.

Ash's hand stroking my cock helped it along. It had been so long since I'd cum or felt any pleasure down there it was amazing, heaven. I felt the sperm building inside me, the semen gathering as Ash stroked me.

"Cum for me, Michael. Now. Cum." It wasn't encouragement, it was a demand. Ash was demanding I cum, right then.

I obliged. My muscles began contracting and I moaned loudly, a sound virtually the same as when I had been moaning from the pain from her ball beating.

"Fuuuuuuckkkk..." I grunted and then felt the spurting begin.

It kept going. Spurt after spurt. Ash kept jerking, stroking and encouraging me and my cum just kept coming. It was the longest cum I had ever had. Probably the most I had ever ejaculated. 

And it was probably the best orgasm I'd ever experienced. After three weeks caged and all the frustration and hopes dashed and the date that night and seeing Ash in her condo, in her space, and letting her beat my balls and then drain me, that orgasm was like an explosion of pleasure.

Ash kept stroking me until she was certain she'd gotten every bit of cum out of my balls.

Collapsing to the side I moaned and panted, exhausted. My cock was still hard, though it was becoming softer. 

"Wow... oh, Ash... thank you. That... was worth waiting for. Amazing."

"Damn right. Now, you made a mess. Clean it up," Ash said in a demanding tone.

"Wha... oh..." There was a big puddle on the floor where I had cum. "Kleenex..."

"No. Lick it up. Do it."

I blinked a few times. By now I knew never to question whether Ash was serious about these things. She meant exactly what she had just said. She wanted me to clean up my semen puddle by licking it up.

The puddle was right next to me, so I rolled over back onto my hands and knees, leaned down and began licking.

I'd never tasted semen before. It was gross, I had expected it to taste bad in some way, but no, it only had a slight taste. What got me was just how slimy it was. I mean, it was gross. Some biological discharge from my body, pure slime.

"Ash, please... this is gross. No one should have to--"

"Oh fuck you Michael. You guys always want blow jobs and to cum in women's mouths and see them swallow it. And we do it, too. For you guys. So don't jerk me around, I know exactly what that stuff is like and I know it's nothing. Get the rest of it."

Oh. She was right, actually. I'd actually cum in a couple of women's mouths before and hadn't even thought about it. This was no different than what I had asked them to do. So...

I licked the rest of it up. I lapped and licked and made sure the floor was nice and clean. And I swallowed it all.

When it was all cleaned up Ash told me to lay back on the bed. "Let me get your cage back on."

Oh. Yeah. This freedom and sexual fulfillment was temporary. I lay back, spreading my legs to give Ash access to my genitalia. She tugged and pulled my flesh through the too-small rings, getting everything set for the cock cage and sheath that covered me and prevented my cock from expanding or being stroked.

She lubed up the urethral insert liberally (she knew how to do this) and slid it inside me, slowly but steadily. The familiar sensation of the probe going far up inside me was actually somewhat welcome. I started to get erect but she was pushing the cage on hard, pushing against my cock and forcing blood back out.

Ash smashed and pushed my cock back with the cage and eventually managed to get it on all the way and aligned with the rear cock rings. With a final click the lock went into place, announcing that I was once more locked up and under Ash's control. Subject to her whims.

Ash ruffled my hair and said, "Good boy. Time for you to go home. You can leave now."

I stood and got dressed as she watched.

"Don't expect this often," she commented as I pulled on my shirt. "I took pity on you. It's better if you maintain solid, strict discipline over your body and urges. I was a softy tonight. See you on Monday."

I showed myself out of her house and drove home.

It was a good night. My balls didn't ache and even though I relived having Ashley jerk me off in her house while on my hands and knees, I wasn't frustrated.

No, I had another date with Ash, was invited into her house, got naked and had an orgasm with her. I mean, if that doesn't constitute her and me in some sort of sexual relationship, what does? I had to admit, Ash was becoming a bigger and bigger part of my life. I didn't mind not being able to date.

Ashley was my keyholder and I had turned myself over to her, and that was OK.