The Strap-on pt. 4 “Oh hell no!”

The further adventures of Ali and... what was his name?

[This series, of which this is Part 4, begins with a gift that is put to unexpected use. Chronologically, this part follows Part 2, but Part 3 is perhaps a flashback to happier times and earlier training. Ali keeps her boyfriend off balance, but he keeps coming back for more. He’s in a chastity cage as this part begins, and he’s been there for eight straight days.]

Ali saw the wet spot on my boxers and, with a contemplative air, slowly pulled them down to my knees so that I stood before her completely nude except for the underwear at my knees. I could only imagine what she thought of what she saw. She reached out and held the chastity cage, twisting it a little so she could inspect me for the leakage she knew was there. I thought I could detect traces of desire and lust, pity and maybe something else like scorn or derision, flitting across her face, and I knew she intended for me to see all those things in her glance, but that doesn’t mean they didn’t have their intended effect. My spirit wilted a little bit under her gaze, but all I could feel, as she twisted that cage, was how great even that felt, and I wondered whether it could actually make me cum.

I looked down at my body as it stood before her, too. As excited as it was, my limp cock nestled smally in the cage as if it was trying to avoid being seen in the bright light. I wished it wouldn’t do that, since Ali was thinking of getting me a smaller cage – she’d shown me the one she intended to buy for me. I didn’t think it would be uncomfortable, exactly, but a guy doesn’t like to think of that part of himself as so… negligible. Back when I could have them, I liked to think of my erection as at least reasonably impressive, but in the cage doing its disappearing act, my dick was just pathetic, and there would be no erection as long as it stayed there.

It was maybe a little redder than usual, and my balls must have been a little bluer. They felt swollen. It had been over a week since she’d put the cage on me, and during that time she’d relentlessly teased me, demanded sexual services, and deflected all my requests for release with vague hints and suggestions of pleasure to come. I’d been so horny the whole time, and the whole time my cock had stayed limp and tiny, leaking continuously the stretchy precum. It was demoralizing, and I felt myself approaching a limit.

Ali touched the tip of the cage where there was a little precum, and when she moved her finger it stretched with her to an impossible length: one foot, two feet… it finally snapped at three feet, and Ali game me a knowing look. But I don’t know what she knew.

I thought my faith in Ali was fading somewhat. Was that what she knew?

Was she ever going to let me go? Was she ever going to unlock my cock and let me cum? I didn’t know. I hoped, of course. I’d never wanted her so much, but in a way I was close to a breaking point, a point where I would just give up on the game, demand my release and, if she refused, find what I needed to remove the cage myself. What I would do after that I didn’t know, and I didn’t like to think about it. I wasn’t sure our relationship would survive my doing that, and I wasn’t sure I’d want it to.

She had complained during the week that she hadn’t been “properly fucked,” as she put it, implying, contrary to the facts and all my desire, that it was somehow my fault for not making love to her – when she held the key and was the only reason I couldn’t. But I still somehow felt guilty! Of course whether she’d been “properly fucked” or not (whatever that meant), she’d had me use the strap-on she gave me every day between bouts of oral sex. She’d always been one to have multiple orgasms whether by tongue or cock, but was clearly enjoying herself at a whole new level. I was beginning to think my desperation was part of her enjoyment.

She read some of my thoughts.

“It’s only been eight days,” she said. “Are you so impatient for release?”

Clearly I was so impatient, considering all the wild thoughts going through my mind, but suddenly I hesitated and felt reluctant to say so. Ali had been the best lover I’d ever had by far, and she’d never ignored my pleasure without a purpose. It had only been eight days (eight days with the length of eight long nights!), and suddenly I felt like a wimp even for complaining. I shouldn’t be letting my caged cock do the thinking for me, but how could I help myself?

What an eight days it had been; what if she wanted me to go another eight? I didn’t think I could stand that.

“Honey,” she said. “Have you ever had so much pleasure as you had this week?”

What the heck kind of question was that? I’d spent the past week in an agony of unfulfilled want! But when I thought about it, it did make some sense. Being horny felt great, and although my dick was held to a minimal size, it had never occupied so large a part of my thoughts. It tingled constantly, and it felt good. I didn’t know how to reconcile so much anticipatory pleasure with so much frustration at is continual denial.

Ali studied me and my cock and then smiled.

“I have just the thing for you!” she said. “Lie down on the bed.”

I did that and watched her reach into the bedside drawer.

At first I thought she had pulled out the strap-on she’d bought me almost two weeks ago that started all this, but it was a little bit different. The first one had been a peachy flesh color, but this one was a darker purple, and it was solid, unlike the other one.

She saw me staring at it.

“His and hers,” she said and shrugged theatrically. “Mustn’t play too fast and loose with germs!”

She waited for me to digest that and agree about germs, and then to absorb the fact that the seven-inch dildo she’d just pulled out was “hers.” I didn’t think that meant it was going into her, though – that’s what the “his” dildo had done.

As usual, she read me.

“That’s right. Turn over on your stomach.”

I want to tell you I saw what was coming and refused, that I refused to let her even begin to put that thing into me, demanded that she uncage me, and engage in normal sex like we used to have. That sex is reciprocal and not a constant power game; it’s about communication and mutual pleasure rather than exploitation and abuse.

I’d like to say that, and in my heart I did say it, but then I rolled over onto my belly as instructed. I was not surprised when I felt her finger spreading lubricant on one of my tenderest spots. I felt her finger slide into me, spreading the lubricant inside me, and then I felt that monstrous dildo at the entrance to my anus.

“Lie still,” she said, as I tried to move away from that thing, which was impossibly big, pressing against an orifice that was never meant to take such abuse.

“Ah, good,” she said as I lay still, holding the muscles tightly closed. There was no way that damn thing was going into me!

But it did. Despite all my efforts, it went slowly, inexorably, into me. Ali pushed it a little, at first just trying to get the tip into me, then pulling back a little, then pushing it back in, and as she did this, gradually going deeper, I could feel the resistance giving way as my muscles slowly accepted the monstrous intrusion.

When she finally got the thing all the way into me and was able to move it in and out a few times pretty smoothly, Ali somehow attached the thing to the harness I hadn’t even noticed she was wearing. I felt her moving around while she was putting it on, but like a moth pinned to a board I couldn’t really move with that thing up my ass. Why do people do it?

“Just relax,” she said. “You’ll love this.”

She began to thrust in and out, much the way I’d done with the strap-on with her, but whereas I hadn’t really gotten any pleasure from what I was doing, other than the pleasure it gave her, of course, she seemed to be enjoying herself. I can’t really describe the feelings I had. It felt good in a way? And every now and then it felt sexually good. The nearest I can put it, it felt like the action analog of being in the chastity cage – I wanted to be excited, my body was crying for it, but it seemed mainly to be an excited desire rather than any kind of fulfillment.

“Are you cumming?” Ali asked after a while.

“Do you expect me to?” I gasped.

We’d been going at it for maybe fifteen minutes by that time, with her making some of her usual pleasure noises, and I guess I’d done some, too, though I’m not sure why.

“I want you to, baby,” she said. “Cum for me!”

“I wish I could!” I said back, and maybe the pleasure feelings were coming a little more often, but after a while she finished what she was doing, and I did feel vaguely exhausted.

She rolled me over on the bed.

“You did cum!” she exclaimed. “Look at that wet spot!”

“It’s just more leaking,” I said, desperate for some reason. Could I have cum without even knowing it? I did have the usual drained feeling, but I was still so horny! I was just all confused.

“You made a circle over a foot in diameter. You call that leaking? Look. It’s real cum!”

She dabbed some off the cage and showed me, and damned if it wasn’t. She absent mindedly dabbed it onto my lips for me to lick, but I couldn’t really taste it.

“Since you came, I guess this is a good time to put the new cage on you!” Ali said brightly. “I think we’ll go with this one you haven’t seen before, a plastic one that won’t fit unless you’re completely soft.”

With that, she took off the old cage and took out the new one while I was lying there without anything on my cock for a change. The new cage looked like a small plastic penis. I desperately tried to get excited so it wouldn’t fit, but I stayed soft and ever so malleable. I’d been without sex for a week but couldn’t get any action down there at all, and before long she had it on me, new lock and all.

“We’ll see how that works!” she said, patting it dismissively, and I knew I had a long week in front of me. The super weird thing was that I couldn’t stop thinking about that dildo. Did I want her to unlock me and let me make love to her? Or did I want her to peg me again?