Shooting the Moon

"And I have to invite them to watch," Diego said.

More gasps from the girls.

"I started by telling Isabel's older sister," Diego went on. "She laughed and called Isabel a tyrant and said I could go ahead and do what I needed to do without her watching. The next time I asked Isabel's younger sister. She made me beg but eventually said yes. She also thought it would be wrong to watch. But the most recent time, I asked Isabel's niece..."

What followed was another long, pregnant pause - a third-trimester, verging on overdue type of pregnant.

"Isabel's niece was delighted. She agreed to let me cum, but only if she got to watch, and only if she got to bring her friends. There were six of them. They put numbing spray on my dick... it took me almost an hour."

We sat in silence, imagining six teenage girls surrounding Diego on the couches of his own home, cheering and laughing as he sucked himself off.

"Diego," I interrupted the silence, "Did you decide who you were going to ask for permission next?"

Diego looked up briefly to catch my eye and then back at the ground. "You," he whispered.

I don't know if he was telling the truth, but Diego was getting my three points for sure.

I glanced at Cheryl who made a noise like she was about to speak. I saw her biting her lip and her eyes twinkled as she spoke. "You know, it's all a little far-fetched. A man being that flexible? But if it's alright with the other ladies, I'd be willing to give Diego and Isabel five points if they can prove it to us right now."

Isabel smiled.

STUART

"Stuart, this might seem like a weird question, but I want you to use your imagination. Picture our current society but with male and female roles reversed. So women everywhere are in a state of regulated chastity. Just like men today, if a woman is reported with her chastity belt off she will be given a piercing that ensures the belt is impossible to remove in the future. Women must submit to their keyholders, and if they cannot find one, they can only seek release at a government clinic. This means that women everywhere are desperate for sex, including your wife. And so instead of going down on her, you could demand as many blowjobs as you wanted, and she would give them to you eagerly. The question is simple - almost a freebie. Would you rather live in that world, or a world where nobody was in chastity?"

Stuart gulped and looked at his wife.

"We only get the points if we answer the same way?"

"That's right, Stuart."

"I'd pick the world where women are in chastity."

It was a perfect lose-lose question for a man. I saw Cheryl fold her arms across her chest and glare at him. Stuart was getting spanked tonight, no doubt.

"One point for you and Cheryl," I ignored their little tiff as I flipped through some of the options for the next question. "If your wife let you fuck her right now, no condom, how long would you last?"

Another pause.

"Two minutes."

"Stuart, come on." Cheryl, obviously angry, showed her response which read '10 seconds'.

"Alright Stuart, let's try and do better on this next one. I want you to guess how many orgasms you give to your wife for every one full orgasm that she allows you to have."

"Easy," Stuart looked relieved. "50."

Cheryl held up her answer which also read 50.

"What the hell -- did you guys cheat or something?" Kitty spoke out.

"Nope," Cheryl looked appeased by the small victory. "It's part of the system we're using. He brings me to 50 orgasms, and then he gets his one. It's a great incentive program for him. I'm not sure how long we'll keep it. I'm getting a little bored of the predictability, but it really does keep him motivated."

"Alright then," I nodded at Isabel who updated the score.

QUINCY

"Quincy, explain to us how you haven't touched your own cock since your eighteenth birthday."

Cheryl was asking the questions since I couldn't interview my own husband.

"I've had very strict keyholders M'am. I shower with the cage on and my hands are usually tied up when it's off."

"What about shaving?"

"I had laser hair removal performed when I was 18, and again seven years later. I haven't needed a repeat since then."

"Do you miss touching yourself?"

"Honestly, it's been so long. Of course I'd love to try if my wife let me, but at this point I really forget what it's like. I know I'm dependent on Sandy for whatever pleasure I get and don't try to fight that anymore."

"Alright Quincy, that makes sense. So some of these next questions are fast and quick and we're asking everyone the same ones. Let's start with this... how big is your cock?"

There was a long pause. Since I knew what was coming I looked around the room to gauge the reactions.

"Three and a half inches." He spoke with whatever quiet dignity he could muster.

Cheryl and Isabel started laughing.

"Quincy, could you be a dear and go fetch us a ruler from your kitchen," Cheryl said when she had calmed herself. "It doesn't have to be a long one."

DIEGO

Isabel had positioned Diego at the base of one of the couches with his back on the ground and his legs over his head. She had removed his clothes and his huge cock dangled from his torso, half-hard.

Kitty was sitting on that same couch, looking with interest when she spoke out.

"If it's okay with the rest of the girls, I know Diego needs someone to help him pull this off. I'd really like to be the one to do it. I'd give everyone one of my points if we all thought that would be fair."

Much as I would have liked to have been the one playing with Diego, my main goal that evening was to fuck the man of my choice, and I was already regretting giving points to Isabel. Pulling well ahead of Kitty would absolutely be worth it.

"I think that's a great idea" I spoke quickly.

The other ladies followed my lead, and though I could tell that Isabel was reluctant, I saw her glance down at the scoreboard and then she too agreed.

So Kitty knelt down, positioning herself so that Diego's head rested in her lap.

At first she spoke so softly that I could barely hear it.

"I want you to relax now. Breathe in, breathe out." She reached out and grabbed his cock as she spoke. His body shivered and she waited for him to settle. "I want you to realize what is going to happen. I have your cock in my hand, and I am going to take it and feed it to you. And you are going to blow your load in your own mouth. There's no escaping it, so there's no point in struggling."

I slowly watched as his cock thickened in her delicate hands. Even from the beginning her fingertips had been unable to make contact.

"Good, now as you come to terms with it I'm pushing your legs downwards. Good breathe in. Good. And when you breathe out I'm going to push your cock closer to your mouth. There we go."

Like everyone else in the room, I watched in a trance as Kitty babied him through these slow steps. It was clear that he had been quite nervous and his exceptionally large cock was not actually done growing. She tugged on it as she spoke, pulling from the base as if she was manually drawing the blood down its length.

"You know I was chatting with Isabel about you earlier. She said you both lived in the same dorm in college. You were a couple years older than all the freshman and you used to pick up girls at the bar and bring them back to your room. She said she would hear them screaming in the middle of the night as you fucked them. But the first chastity laws came into effect halfway through the year and suddenly the screaming stopped," she paused her caresses. "You must have had so much swagger back then. I wish I could have seen it."

She resumed her stroking.

"Fuck, look how huge you're getting." She whispered to him. "That's a dad-sized dick if I ever saw one. Are you ready to suck on it for me Daddy? I know that a man like you, who remembers the old days, must find this so demeaning. So I wouldn't want to do it to you without your consent."

Consent. There's a word I haven't heard in a long time.

She guided his cock to the entrance of his mouth and he opened his lips to receive it, but she moved it to the side like a schoolyard bully holding a toy just out of reach.

"Did you want it in your mouth Daddy? I need to hear you say it."

She slapped his cock against his cheek tauntingly and giggled but Diego couldn't bring himself to beg for his humiliation.

"Please don't torture me," he whispered. "You're a nice girl. You don't have to do this."

"Oh Daddy. Haven't you realized? There are no nice girls anymore."

She dragged the head of his dick across his lower lip.

"Come on Daddy, it's been two months. I bet Isabel edged you before coming tonight. She probably played with your cock every day this week. Am I right?"

Diego nodded 'yes'.

"You must be so horny. You must want nothing more in this world than to wrap your warm lips around that cock. All you have to do is ask."

His shoulders slumped just a little. He had given up. They always do.

"Please, I want it," Diego admitted, but under his breath.

"Louder Daddy, I want you to beg for it," Kitty bit her lip as she waited.

"Please, let me suck my own cock."

"Hmm, that's better. I promise to help you feel good Daddy."

Diego opened his mouth, and she slipped the whole head of his cock inside.

He looked ready to melt.

"Good, that wasn't so difficult now, was it?" Kitty continued. "I'm gonna push down a little more on you. There. I'm going to keep doing that. Pushing a little and then releasing so that it bobs up and down in your mouth. Do you like the taste of your own cock, Daddy?"

Amazingly she had managed to force almost three inches into his open mouth and so of course Diego did not reply.

"Now I want you to actually suck on it, okay? I should be hearing sloppy noises just like when you go down on your wife."

Kitty's tiny hands pulled his cock in and out of his mouth rhythmically as she spoke. Then she moved back up the shaft until she gripped his balls.

"I bet that feels amazing after not coming for all this time. You must have been so traumatized by having your niece and all her friends watch you. Laughing and cheering. Did they help you like I'm helping you? Six pairs of hands, roaming over your body, squeezing your balls and urging you onwards. I hope they were kind. I hope they stripped to their little polka dot panties to give Daddy a show. But they can't have been too nice or you wouldn't have waited so long to try again. What did they do to you Daddy? Did they squeeze too hard?"

I watched Kitty's one hand tighten on his balls until he groaned. "Did they make you beg? You poor thing. So scarred that you spent two more months in your cage. I bet you were getting close to asking for permission again anyway? Am I right?"

Diego mumbled in agreement.

"I wish I could have been at that party. I love watching girls attend these events for the first time. There's always one innocent little thing, so scared to touch and play along. You know the type right? The shy one with no older brothers or experience with boyfriends. The one standing in the corner covering her mouth and blushing furiously, hoping that nobody notices how she has absolutely flooded her panties."

Diego's cock twitched, either at the conjured up scene or his memory of what had really happened.

"I wouldn't be too embarrassed if I was you. I bet there's a girl out there tonight, still masturbating to the memory of your huge cock. Remembering how her tiny fingers struggled to wrap around you," Kitty mimed the actions of the virginal 18 year old, tentatively closing her hand around Diego's throbbing rod, one finger at a time.

"Can you picture her lying in her bed? Wearing only her pajama bottoms. She's pleasuring herself with one hand and sucking on a dildo that's half your size, wishing it was you, wishing she could go back in time and take your warm meat into her mouth just once," Kitty licked her lips as she spoke and I half expected her to act out on her fantasy. "She's whimpering softly because she doesn't want her parents in the next room to hear her. But it's hard to be quiet because that cock feels so right on her tongue, and her fingers feel so, so good on her pussy."

Kitty batted her big eyelashes at Diego and then leaned in closer, "Are you picturing it? She's trembling, and there's perspiration on her forehead. She arches her back and you can hear her hand as she rubs herself under her pajamas. She's sliding that dildo in and out of her cute little mouth and then she lets it slip from her lips just long enough to whisper, 'Fuck me Daddy'."

Diego groaned and saliva escaped from the corner of his mouth.

"Oh, is that what really gets you off? The thought of fucking a girl who is half your age? Having your way with her?"

Now she began pumping faster and Diego moaned even as his mouth was stuffed with his own flesh.

I'll admit the whole display was unbearably erotic. I was squirming uncomfortably in my chair and I saw Cheryl and Isabel doing the same. Even if I was growing to despise Kitty, there is nothing I find more arousing than watching a beautiful young woman force a stronger, older man to degrade himself for her pleasure.

"Fuck your cock is so huge. I wish I could feel it spewing inside my pussy. I wouldn't be able to keep you locked up for more than a day before I needed you to plow me again. Letting you fuck me over and over until I was too sore to walk. Oh, is that bringing you close?" she asked as his body shuddered under her touch. "Are you almost there, Daddy? Thinking about fucking me? Making me into your good little girl?"

Diego's eyes opened wide in panic as he realized there was no avoiding what came next.

"You don't have to resist anymore. A man with a cock like yours doesn't need to prove his stamina. Cum for me, Daddy."

She pushed him down one final time and then held him in place, with his cock buried as far into his mouth as it would go.

I watched Diego's balls draw close to his body, and saw the contractions of his muscles, first in his shaft as it pumped rhythmically, and then in his throat as he swallowed. Try as he might, Diego couldn't keep up with the monstrous firehose in his mouth, and white streams overflowed from the corners of his mouth.

When he gulped for the last time, Kitty finally pulled his cock out of his mouth. She inspected it closely, squeezing from base to tip and drawing out a final drop onto her finger. She held her finger up to her face and inhaled almost imperceptibly, but then quickly wiped the drop on Diego's lips.

She was beaming as she did it.

QUINCY

"Is that as big as it gets?" Isabel asked me as she lined up Quincy's dick with the ruler.

"Maybe a little bigger, but not much," I replied.

"It's so adorable," said Cheryl. "Like a baby carrot."

"It's not quite 3.5 inches yet. I'm gonna give it a few more pumps," Isabel said as her hand swallowed tiny Quincy in its grasp.

When she stopped to measure again I saw Quincy thrust out his hips slightly and his little penis throbbed as if he was willing it to grow just for the measurement.

"Well it's definitely not three and half, but I think it's okay to let Quincy round the number up a bit," Isabel concluded.

"Why did you never tell us that your husband was so inadequate?" Cheryl asked me. "I always thought when I saw him in his cage that you just picked out something too small as a punishment."

"I told you he was below average," I replied.

"Honey, this is not just below average," Isabel pulled Quincy's penis almost straight down and then allowed it to spring back into place like a pinball flipper.

"It is pretty piddling," Cheryl agreed with Isabel, "but I think marrying a man who is part-centaur has given you unrealistic expectations."

"I like Quincy's penis," I shrugged. "It's easy to hide during our dress-up games and his tongue does all the work that the rest of him can't."

"Well it's much too small for my tastes," Isabel flicked Quincy's dick with her fingers, this time sending it swinging from side to side, "But I do think it's cute that you two are together. You're like the princess that kissed the... tadpole."

Cheryl laughed again while Kitty sat and watched without comment.

Perhaps Kitty thought that it would be poor form to mock the hostess's husband, but I honestly wouldn't have minded. In fact, I took a perverse sexual thrill from hearing the other ladies make demeaning comments about Quincy and watching him wither. I knew when I first saw the question about penis size that something like this was bound to happen, and had been looking forward to Quincy's miniature reveal all evening.

I was already anticipating tormenting him about this during his next edging session. 'Quincy dear, what did Cheryl compare your penis to? A baby carrot?? Why don't you grab one from the fridge so we can check. I'm sure you're much bigger than that!'

At last Isabel took her seat and Quincy's humiliation came to an end. For the time being at least.

"Alright, Quincy, let's get back to our next question," Cheryl began. "What is the most recent sex toy or item used for sex purchased by your wife?"

"I had been complaining about getting sore knees from our breakfast routine. So she bought me kneepads."

More giggling from the girls. The knee pads hadn't occurred to me so we wouldn't be getting this point, but I laughed along anyway.

"I guess you're not eating oatmeal during this breakfast routine then, are you Quincy?"

"No M'am."

"Unfortunately, Sandy wrote down 'Butt plug' so no points for you. Next, we want to know if your wife has any embarrassing or teasing nicknames for you. Maybe a name for your penis, like thimble-dick, or something like that?"

"She calls me her dripslut."

Isabel let out a squeal of delight.

"Oh that's cute. I guess from when you leak in your cage?"

He nodded.

Cheryl checked my answer quickly. "Okay that's another point. Only a couple left now. Quincy, does your wife allow you to kiss her after you go down on her?"

"No, never."

Cheryl checked the answer on my board and nodded to Isabel to add another point.

"As expected. Alright, and what is the most recent game that your wife has used to decide when you were allowed to orgasm?"

"Umm, I'm not sure if this counts as a game. She kept me locked up, and she'd tease me without taking off my cage. And as always, I spend a lot of time on my knees. So she said that I wasn't allowed to orgasm until my precum dripped all the way from my cage to the floor while kneeling. It took almost three months before it finally happened."

I smiled to myself as I recalled the memory.

"Alright, final question Quincy," Cheryl continued. "What is the most humiliating thing your wife has ever done to you."

I scribbled down my answer, "NYE countdown". Then I did my best to put on a serious face as I stared at Quincy, hinting that I wanted a detailed description. I hadn't tallied up all the points yet but other than Kitty and Kayden who were way behind, it looked like a close game.

"There was a time when she only let me cum by counting me down from ten. She told me she wanted to train me to cum on command. At first she would give me stimulation all the way to the count of zero, but then she started removing her hand earlier and earlier. She made me watch videos of women doing this to men. Counting them down while they played with their cocks. After a couple of years it seemed like the only natural way to cum. Finally she was able to give me a ruined orgasm just by counting down while she rubbed her body against me or let me suck on her breasts."

I smiled to myself, knowing what came next.

"Last year we were at a New Year's Eve party for my job. She chose my outfit for me -- white pants, white top, black tie. On our way there, before we got out of the car, she took my cage off. I struggled all night to conceal an erection that came and went at the slightest provocation. But she loves to torture me so I thought little of it. We were on the dance floor when the countdown started, and I was already partially hard from dancing next to Sandy. But she moved behind me and wrapped her arms around my shoulders. I started noticing some of the single women from my workplace were looking at me, like they were expecting something. And then, along with the crowd, my wife started counting down in my ear."