The Strap-on, pt. 2

You didn't think it was over, did you?

[In part one of this tale Ali gave our hero a gift, a hollow strap-on dildo. He hoped at first that it might be a way to satisfy Ali’s stated fantasy of double-penetration, but after putting it on him Ali first compared the size of the thing very favorably to the size of our hero’s manhood, then pretended to give it a handjob, and finally put it on over her man’s cock. He was able to please her with it enormously but without feeling much of anything, and when the time came for his reward, he found himself suddenly locked in a chastity cock cage.

Ali persuaded him this was just to make the following day more pleasurable, and our hero spent a hard – no, let us say a “difficult” night – in the cage, unable to sleep because he was so horny. Our story picks up the following morning.]

They say that even if you think you didn’t sleep a wink all night you probably slept five hours, or I think I read that somewhere, but you couldn’t prove it by me. All I know is that if I did manage to get any sleep at all, it was a light sleep punctuated by all sorts of lurid dreams. I felt I was being devoured by sexual hunger, and this was only made worse by the fact that I couldn’t even get hard. Somehow it all made me feel weak.

I woke up and lay quietly for a while, then finally just got up, a full hour before Ali. The first new indignity I had to endure was the change in my peeing. It wasn’t possible to stand up and do it the way a normal guy would, I had to sit on the toilet, being careful not to piss down my leg at that. Then, to pass the time until Ali got up I first took a brisk walk around the block and then found myself washing dishes and making breakfast. I simply had a tremendous amount of (caged) energy I needed to burn off.

When Ali finally did wake up, I found myself in the strangest position. I was waiting. Waiting on her, and waiting for her. She had put the cage on my cock and kept my desires raging all night without making any definite promise as to what, if anything, she would do to ease my discomfort or what, if anything, I could do to persuade her to do so. My cock was leaking pre-cum. I’d put on a pair of underwear and sweat pants when I got up, and there was a wet patch high up on my right leg where I’d been leaking.

“I made breakfast for you!” I said, bringing in a tray with food on it.

“Umm, not now,” she said, ignoring the tray. “You have a wet spot. Did you need to use the bathroom?”

“No. I’m just excited,” I admitted. “I’m leaking a little is all.”

“That’s hot,” she said. “Take off your clothes.”

I did so and stood, clad only in the cock cage, as she surveyed me from under the covers.

“I see,” she said. “You don’t seem very excited, but you do have a little leakage problem. Should I get a smaller cage for you? You aren’t taking up any more than half of that one, and I want it to fit you right.”

“Why not take it off?” I practically begged, hating the whine that had crept into my voice. “I’m sure you would be able to tell how excited I am then!”

She smiled ironically but otherwise ignored that.

“Hand me my phone, please. I do think I should get you another one.”

For some reason I gave her the phone. I knew I could refuse and thought that if I insisted, she’d take the thing off of me, and the game seemed to have taken a sinister direction, but I also felt mesmerized or… I don’t know. I was standing there nude and on display, my cock held captive, and at some level I just felt like I had to do what she told me to do. And god I felt horny. I even thought if I did as she instructed she might take it off and let me have some relief.

So I gave her the phone, and first she took a couple of new photographs of me, but then she started looking up chastity devices, swiping through her options.

“No, too big,” she said to herself. “No, too big… No, too easy to take off… ah! Take a look at this one, dear!”

I looked where she pointed. I think it was called “my little hero” or something corny like that. It looked like a thimble on a hinge. With a big lock and a weird looking metal straw of some sort.

“What’s that?” I asked, pointing to the straw thing, realizing even as I spoke that it was the dumbest thing I could have done. I could have ridiculed the size, demanded release, grabbed her phone and stomped on it… anything! Anything would have been better than asking that lame question.

She smiled and looked me up and down again in a way that reminded me I was naked and she was covered and stripped even the thought of will-power out of my mind.

“It’s just a little thing that’s supposed to make things better or something if you need it. But I doubt it would ever be necessary. Yes, this is the one!”

She ordered it.

“I’m horny,” she said when she’d finished ordering the new cage. “Why don’t you make yourself useful?”

“How?” I asked, realizing again how lame that sounded.

“Your tongue,” she replied, pulling off the covers and spreading her legs. My only thought was how best to comply.

After she’d orgasmed several times Ali pushed me away with a sigh.

“That was so nice! Thank you!” she said, pulling the covers back up to her neck so that again I was nude while she was covered up. If she was doing that to make me feel powerless it was definitely working, while the fact that I knew she was naked under the covers with the wettest, slickest pussy imaginable kept my desire at a fever pitch.

“Can we do more now?” I asked.

Again it sounded sickeningly like a whine, but I was so desperate! And again Ali ignored the tone and acted like my request was completely normal and something she fully planned to honor – some other time.

“Maybe after breakfast.”

She ate then, while I sat on the bed. When she was finished eating, she asked me to get her the book on top of her desk, so I got that for her, fearful that she’d spend the whole day reading and forget about me completely. As to that, however, I was wrong.

Ali read for about an hour, looking up every so often, giving me the once over as if she was contemplating letting me go and having sex with me. This kept me in a perpetual state of readiness, and I didn’t dare go do anything else for fear I’d miss my chance.

Finally she got finished with her reading.

“Do you know where the strap-on is?” she asked. “In the bathroom,” she answered her question.

I nodded.

“Will you go get it please?”

I did so.

“And now put it on?” she asked.

“Like yesterday?” I asked, hoping she would take the cage off at least for that purpose, but it was not to be.

“No, this time I want to try it with you still in the cage to see how that works.”

Ali has a wonderful body. She’s thin in all the right places and thick in all the best places, and when she pulled the covers back off of her I just about died with desire, and god! My poor cock! I thought it would either explode or break the cage with my desire, but nothing doing – it just sat there, limp and tiny, enclosed by the unyielding steel. There was a small but steady flow of pre-cum weeping out of it.

I tested Ali’s readiness with a tentative finger, slipping it deep into her pussy.

She sighed with pleasure at that and pulled me down to her.

I carefully guided the strap-on into her then and she gasped with pleasure.

“Oh, that’s so heavenly!” she exclaimed, writhing under my ministrations. Even an hour after the oral sex I’d given her, and after her meal and the reading, she was only a touch away from orgasm, and she started cumming right away. Meanwhile I could take deep strokes, looking down at my massive artificial member that was bringing her such joy. I could watch it slide in and out, could see Ali’s slipperiness from her beautiful pussy all over it and imagine how it would have felt if I could have felt anything.

I was so jealous of that strap-on! And my actual cock, caged and useless by comparison, flapped pathetically as I moved. It was maddening, but I did the best job I could, believing that my own pleasure would come after her complete fulfillment. Strangely enough, the movement of my cock, caged and all, was stimulating me more than I could have imagined. I was actually worried I’d cum if I wasn’t careful.

Finally she pushed me away with a sigh.

“That is so much better than you usually do!” she said. “You use it so well!”

What is a guy supposed to say to that? Was she encouraging me? Or humiliating me? It felt like both, and I gave a disheartening little shit-eating grin and laugh as if it was a compliment in the hopes that she’d finally unlock me and let me take my pleasure.

I think she knew me better than I knew myself. She gave me a sharp look, very brief, and then subsided back into bed, pulling the covers back over her.

“Can I take this off?” I asked, meaning, as usual, the cage. I meant the cage!

“Yes, hand it to me, darling, please,” she replied, meaning, of course, the strap-on!

I took it off and handed it to her, and she looked at it thoughtfully. I swear she was trying to decide whether or not to get out of bed to wash it and put it away, or to make me do it, and I broke. Again.

“Can’t I make love to you? Or at least can’t you let me out of this thing?! I’m about to explode!” I blubbered on. I can’t explain it. I’m usually not such a wimp, but the whole thing had come as such a surprise and caught me so much off guard. And Ali seemed to know how to make everything worse and worse while, at the same time, keeping me in this delectable sense of anticipation so that I was almost afraid that she would take it off and bring the whole thing to an end.

I was a mess, all right. And I was not expecting her to say what she said next.

“You don’t seem to like my breasts anymore,” is what she said, pulling the cover down and revealing her breasts, looking at them with theatrical sorrow. I love her breasts! I have a weakness for big nipples, and hers were always big, swollen even more with the morning’s activities. They looked so good that for an instant I forgot about my own overweening hunger, but it was true that in my anxiety to please her with the strap-on and the oral sex, I had ignored her breasts completely earlier.

“I love them!” I exclaimed, and moved towards her to prove my devotion.

“Oh, it’s too late for today,” she said, pulling the covers back up over them. “They’re too sensitive. You know what cumming does to them.”

I did know that, and for some reason this distressed me.

“It’s okay,…” she sighed. Yes, poor Ali!! She’d only come for about thirty minutes twice that morning! How she was suffering! Even in my pathetic state I could see how ridiculous that was, but she meant for me to feel guilty.

She saw the progress of my thoughts, I’d swear it, and gave a smile I didn’t know how to interpret before finishing her sentence.

“…you aren’t used to the way things are yet. I’m sure you’ll do a better job next time.”

tbc