"Winner, winner, chicken dinner!" I yell out abruptly. This almost got a smirk out of him, I think. "Well, you get reward number one! I will ride you to completion tonight! I tell you what, if you can manage to make me cum with your penis, you can sleep tonight without a cage! Now, on to question number two. Am I happy or upset that your penis is smaller?"
This time he doesn't hesitate, "Upset, Madam." He seems so confident in his answer.
I taunt him, "Oh, and why would I be upset? I told you 5 months ago that toys are so much better for me now anyways. I'm sorry dear but, that is a wrong answer. Penalty for that wrong answer, you must eat me to completion if you are unable to get me there with your penis." I almost feel guilty because that was a trick question as I couldn't care less either way. "Now, this is going to be the final question, get it right and you will be quite happy. Get it wrong however, and I have a feeling you will not like the penalty. Your length decrease, are you now between 4 ½" and 5", 4" and 4 ½", 3 ½" and 4", or 3" and 3 ½"? Think hard, Dear."
This time he does not answer quickly, I can only imagine what is going through his head right now. He is probably going into full panic mode. After almost a minute of processing he finally has an answer for me. "I think I am between 4" and 4 ½", Madam." He almost sounded desperate with this answer.
"No, no you aren't, unfortunately." I just bluntly let him know. "As it turns out your penis has gotten so small, I don't think you will ever make me finish with it again. It's hardly even a penis befitting such a manly body. It's pathetic if I can be frank with you, 3 ¾" with a matching girth of only 3 ½"." I gave this statement a moment to sink in for him. He lifts his head trying to see even though he can't see anything with that mask on. "It's okay though love! This just means the penalty for missing this question will be waiting for you in the morning. You see, I had bought three new pairs of underwear. One pair that is simple but sexy, that was intended for you if your penis was now 4" - 4 ½". The other is incredibly sexy only fitting for somebody with next to no bulge to fit underneath, somebody with your size penis. Just rest assured tonight that the final panty will not be waiting for you as you are still above the 3 ½" mark. This pair is for somebody that might as well not even have a penis." He is motionless.
Before he can speak or really contemplate what has just occurred, I grab a small amount of lube and push him into me. I start grinding really slow, trying not to get him there too quick. With him in me it's almost as though hardly anything is there; the sensation is disappointing. After about a minute of slow grinding, I start barely picking up my hips and dropping back down. I am methodical and extremely careful not to pull up to high as that would be far too easy now. He slips out after just a few thrusts, he easily slips back in. After just 4 more thrusts he grunts hard, then breathes heavily out. "Well, looks like you get to lick me again." After he starts to shrink, I quickly leap up and sit on his face before he can react. I let everything flow out of me covering his lips and I'm hoping most of it went into his mouth. After almost a minute of smothering his face with his own cum coming out of me, I grab the cucumber. I barely pull off of his mouth and he starts to say something but I shove the cucumber in, exclaiming "Suck it! Suck all of your cum off of this cucumber right now! This thing is the same size you used to be! This is what I have done for you and you now do for me!" This sick moment lasted far longer than I thought it would. Rory didn't hesitate after I started yelling at him, he genuinely looked like he was giving it everything he had. Once he was done and all the cum was cleaned off of the cucumber and his lips, I hop off of the bed and go to clean up.
Rory is left there with his own cum and my juices drying on his face, he does not speak a word. I get cleaned up shower off and then grab his newest cage. This new cage is the exact same as before there is just a head, no shaft room at all and it is tighter and more angled down than previous. This gives it a more discreet look and when wearing jeans/shorts, makes any sort of bulge non-existent. I untie him and remove the mask, all he does is thank me, almost in a state of shock. He gets up and goes to shower off without saying anything else. While he is showering, I pick up the room and put everything away. I leave out the black thong for him to wear in the morning.
The whole panty thing is not at all sexy to me, but it does accomplish the goal of humiliating Rory. This takes everything we are doing to whole new levels and that, that excites me. This whole journey we are going down has been exciting me more and more. Tomorrow I think I'll talk to him more about it all and make sure everything is okay.
-Rory
While showering, I am in a state of almost shock, but also odd satisfaction. Through this entire time when wearing the cage, it was just that a cage. Our lives were fairly normal aside from the fact that my cock was now my wife's. This level of domination, yes, I would definitely call it that now, hadn't been broached before. I absolutely loved it. The degradation, the fact that I can't satisfy her how a man is supposed to, but rather how she wants me to instead. When she slapped my face with my own cum on her hand 5 months ago, the thought of tasting it did come into my mind. Did I ever think she would force it on me in this way? Absolutely not. How turned on this entire night has made me is mind boggling. Then to top it off I cannot believe; how small my cock has gotten!
After I showered, I just went to bed, I did notice that a black thong was waiting for me in the morning on my nightstand. She did say that this that this was for me to wear, I didn't think that she would be into this sort of thing and I don't really consider myself a cross-dresser. No matter, I still obediently put them on just as I do everything, she asks of me nowadays. I'm not exactly sure when I started just doing everything with no questioning involved but it just slowly became a thing. These were definitely sexy if they had been on my wife. Today is my rest day, so instead of running I get to make a cup of coffee and relax on the back patio enjoying the sun rising. The house looked clean and tidy so relaxing is all I have to do this morning, what a change of pace.
Allie finally got up well into the morning and immediately came and sat down with me outside, she had a serious look on her face.
She asks, "Love, how is all of this going for you? Not last night alone, but everything we have been doing? I know you asked for the caging and all of this, I want to make sure I'm not going overboard. If I am please tell me now, before we go farther and things aren't repairable."
I honestly think this is the overall happiest we have been, things are starting to get a bit kinky between us but honestly, I think I like it. I tell her, "Honestly, I think things are going great. I was extremely skeptical in the beginning but I went along with it as it was my fantasy in the first place. You seem to have taken into the roll extremely well! Last night was extremely intense but there was not a single part I disliked. I do have one question though, why are you making me wear this thong? I didn't think you were into cross-dressing at all."
"That all makes me very happy, and as far as the thong goes, it doesn't turn me on itself. However, the humiliation it must be causing you, does. The fact that I know you are thinking about how your penis doesn't even make the fabric stretch, just a snug fit, is very erotic to me. You knowing that your penis has gotten so small it can't even fill a pair of panties, just tells me you should wear them more often. It can serve as a constant reminder that you aren't a real man downstairs anymore, more of a micro-man. Thank you for being honest with me that nothing has gone too far, we can keep pushing forward if you'd like?" She said this with at first joy, then taunting, topping the whole speech off with an almost daring tone.
All I could come up with is, "Yes Madam, that sounds like the perfect idea to me.". I had no idea what was to come next but so far, I'm just getting drawn deeper and deeper.
