Doing Business, Part 30 (Patreon)

Thirty

She dangled the key to my chastity cage in her left hand a little longer–a final tease that I had been so close to release–before casually tossing it across the room. It was gone, for now.

“What do you think?” she asked. “Is this a good look for me?” She had taken the purple dong and held it between her thighs. The placement wasn’t quite right, but if I squinted a little, it did almost look like she had a cock of her own.

I nodded. “Yes, Mommy.”

“This is what all the hubbub is about, huh?” she asked, playfully slapping her toy with the back of her hand so that it bobbled up and down. “Men are so silly.”

I had no rebuttal for this. If anything, it was probably my inability to conform to the social standards of “men” that had resulted in where I was now–crawling around the ground with a wet diaper while my boss stroked her cock in anticipation of using it on me.

“Have you ever wanted to be a girl?” she asked.

“No,” I said, shaking my head. “Well…I never thought about it.”

“Nothing wrong with that. You’re happy with the skin you’re in?”

“I think.”

“How does the idea of this going into your bottom make you feel?”

“Honestly? A little nervous.”

She laughed, gripping the shaft tightly in her hand. “But you want it?”

“Yes…”

“If you end up liking this, you should see what else I brought,” she said, nodding towards her suitcase. My eyes followed to the sealed luggage. What else was there?

For the sake of my own curiosity, I also hoped that I liked tonight’s toys.

“Come up here, Baby,” she said. “Up on the bed with me.”

She didn’t have to tell me twice. I crawled across the bedroom and climbed onto the bed. Her soft hands were on me immediately, easing me down onto my back.

“Do you know that I appreciate you, Baby?”

“Y-yes, Mommy. Of course.”

“You’ve done a lot for me in our short time together.”

Had I done all that much?

“More so than doing the tasks of an assistant,” she continued. “Of which, you’ve done very few so far. And more so than just pleasuring me or entertaining me with your humiliating antics. I think you–just being around–has been good for me.”

“Well…you’ve done just as much for me,” I said.

She straddled my body, hovering above me like an angel as she looked down into my eyes.

“You’re an excellent baby.”

“You’re an even better Mommy.”

She moaned a little, massaging my chest with her hands. Slowly, her hands spread out across my body. She rubbed my shoulders. My neck. My arms. Even my face–softly stroking my cheeks and running her nimble fingers through my hair. It was a feeling of bliss unlike anything I could remember experiencing before.

If she had stopped now, got up from the bed, and put her clothes back so she could go get a sandwich, I think I would’ve felt satisfied. It wasn’t getting off–but this felt like love. I felt loved.

“If I could make you c*m without unlocking your little cock,” she cooed to me, her lips pressed close to my ears, “I probably wouldn’t ever have to unlock you again, yes?”

An absolutely terrifying idea, but one that sent pulses of pleasure through my body. Yes, fine. Destroy the key. Flush it down the toilet. Throw it out a window. Wrap it up in a dirty diaper and throw it in the dumpster.

I bit my tongue–scared that I’d blurt out something I’d regret later.

Fuck.

At the worst possible moment to have a conflict of conscience, I was reminded of my conversation with Kylie and my withholding of that conversation from Mommy. And I was just going to idly lie back and let Mommy pleasure me while continuing to keep this from her?

“M-mommy?”

“Yes, darling?”

“I…I, uhm, have something I need to tell you.”

“Yes? What is it? Do you have to make a poo? Are you going to make another stinky diaper for Mommy while I’m on top of you?”

I really wished that was what was happening.

“N-no. There’s something I didn’t tell you before.”

The smile faded on her face, just a little. “Oh? Interesting timing on your part for a serious conversation.”

“I just don’t think I could fully enjoy anything that would happen tonight if I wasn’t completely open with you.”

She remained on top of me, but she sat up, her moist pussy resting on my cage. “Go on.”

“It’s about…Kylie.”

She laughed. “That’s the very last name I would’ve expected you to say. What about her?”

“She asked me to do a favor for her.”

“Hmm. What sort of favor?”

“She wants me to buy her alcohol.”

She laughed, shaking her head. “A ballsy girl, eh? Did you tell her about us? This isn’t, like, a blackmailing situation, is it?”

“N-no,” I said, shaking my head. “I don’t think so. I don’t think Kylie has any interest in talking to her mother about anything, let alone us. I didn’t tell her anything about us either…though she certainly assumes we’re having some sort of…relations.”

“Well sure,” Mommy said. “I’m sure many people assume. Baseless speculation doesn’t scare me too much. Though I’m curious why you didn’t tell me about this little conversation sooner.”

“I’m sorry, Mommy. I guess…” I remembered that I still hadn’t told her everything. There was still the promise of making things ‘worth my while.’ But did I dare reveal that too?

As if able to, at least partially, read my mind, Mommy asked: “What did she offer you in return for fetching alcohol for her?”

“She just said she’d, uh… Well, she didn’t exactly say how she’d repay me.”

“But the implication was that she would find some way to return the favor?”

I nodded again, my cheeks bright red.

“Even with your little cocklette all locked up, you still manage to do a good amount of thinking with it. Impressive.”

“I’m sorry, Mommy. I didn’t want to keep it from you and…”

She put a single finger over my lips. “I don’t know what you thought you were going to get from her with your cock locked up and in a diaper, besides more humiliation. And if that’s what you wanted, I’m happy to help you reach that goal.”

“N-no, I just…”

“Let’s not worry about it anymore,” she said. “I’ll take care of Kylie. And, right now, I’m going to take care of you, baby.”

I took her for her word, and I let go of that little knot of anxiety I had been holding so close to my chest. It was a great relief.

“Do you wish you were a big boy?” she asked, grinding herself on my diaper where my cage was.

“Y…yes. Mommy, I really do.”

“Alas, Mommy’s kitty isn’t for little baby-cocks, is it?”

“No, Mommy.”

“You didn’t choose the key, you chose the toys.”

“Yes, Mommy.”

“Allow me to introduce you to this fine fellow,” she said, grabbing the purple cock and holding it in front of her. “Not the biggest I’ve ever seen, for sure. In fact, if I took a fella home and this was what he was packing, I’d be a little let down. But, for a little butt-virgin like yourself, I imagine this will do just fine.”

She could try and downplay its size, but I still couldn’t imagine that thing fitting inside my ass.

“Y-you said that there’s another one in your suitcase?” I asked. “A…bigger one?”

She laughed, shaking her head. “One thing at a time, Baby. I can’t wait to show you what else I brought with me. But, as they say: ‘Baby steps.’”

I could accept that. To stick to the infantile metaphors, I’d have to crawl before I could walk. I’d have to…get fucked by a smaller plastic cock before I got to see whatever was to come after.

Her hands were on my diaper, teasing at the tapes like she was going to peel them away. But first, she’d squeeze and grasp the stiff lump caused by the metal cage contained within. Each would draw a moan from my lips–more out of desperation than actual pleasure.

“You want it so badly,” she said.

‘It’ wasn’t defined, but it didn’t have to be. ‘It’ was anything that could get me to climax.

“Yes, Mommy.” I felt my voice fraying as she somehow managed to make me even more pathetic and desperate than I already was. “Please. Please.”

“Oh,” she said, smirking. “Begging. I quite like that. Give Mommy some more of that, won’t you?”

There was no hesitation on my part, I simply turned on the spigot and let it run: “Please, Mommy. Pllllleeeease. I need it so badly. I’ll take anything. Everything. Can I please have it?”

“But why do you want it so badly?”

“Because you keep me locked up, Mommy.”

“Surely it’s more than just that.”

I took a deep breath. Fine, if you really want me to beg. “Mommy, I can’t be around you without getting turned on. Every single thing you do–every single thing you do to me–it drives me crazy. You have me. You have me…” Kylie’s words from dinner came to mind. “...wrapped around your finger. You want me to be a baby? I’ll be the best baby you’ve ever had. You want me to wear diapers? Poop my pants? Crawl around like a baby? Absolutely humiliate myself in front of my roommate, co-worker, pizza delivery girl, and the entire executive team for our company? I’ll do it. Because, at the end of the day, I’ll do anything for you. Any insane disgusting thing you want, Mommy. I’ll do it. Because if it makes you happy, it makes me happy. So, please. Please, Mommy. Make me c*m. Make me explode. Stick anything you want up my ass. Destroy me, Mommy.”

She didn’t respond immediately. Which made sense, given the amount of information I had just vomited at her.

“The pizza girl, hmm?” she finally said. “You’ll have to tell me more about that later.”

“Okay…”

She started peeling back the tapes on the diaper. One at a time, slowly, filling the room with the sound of the stubborn sticky tabs being pulled away from the diaper. When she was finished, she pulled down the front of the diaper, laying it flat on the bed beneath me.

“I have to admit, this isn’t what I’m used to. Usually, when I open your diaper up, there’s a disgusting mess waiting for me to clean.”

I didn’t say anything, letting my glowing cheeks do the talking for me.

“Here,” she said, reaching for something off the bed and bringing it to my face. It was one of the new pacifiers, which she plunged into my mouth.

“There’s really nothing you need to say,” she said. “And you’ll still be able to do all the moaning and groaning you need to.”

I nodded.

“Now hold this for me.”

Before I knew what was happening, she had grabbed both of my hands, clasping them together above me and she then thrust the purple plastic cock into them.

It felt surreal, holding this toy in my hands. Perhaps it was a bit prudish on my part to have felt so strange, but I’ve never held a dong in my own hands before. It didn’t feel that different from what I had expected: firm, with a little flex to it. Soft to the touch.

It was then clear to me why I was holding it–she had the lube.

“When playing with little bottoms, it is of the utmost importance that everything be good and slippery,” she said. “That means both our purple friend here, and your little backdoor.”

She squeezed a glob of clear gel into her hand before slowly applying it to the toy, thoroughly covering every square inch of it. Now, under the room’s lights, it seemed to glisten and shimmer–as if some sort of holy relic.

“I’ll be taking Mr. Purple back,” she said. “Now, there’s a few ways we could do this, but I think a better angle–for the both of us–would be if you rolled over.”

I watched her squirt another batch of lube into the palm of her hand. This time, she carefully dabbed the fingers from her other hand into it, spreading it to her fingertips like an artist putting paint on their brush from the palette. Then she slid off my body, giving me plenty of room on the bed to flip over. I did, finding this new position to feel even more vulnerable than the last. My ass was sticking up in the air–hers to do as she wanted with. My caged cock now rested on the wet diaper under me. Fitting, really, that I should never be too far away from my diapers.

She began to carefully paint my bottom with the lube. I felt myself instinctively tighten up at her touch.

“You have to let me in, Baby,” she cooed from behind me. “Take a deep breath. Relax.”

I did exactly that: I took a near-infinitely deep breath. I relaxed. Relaxing wasn’t easy. With my body in this position, and with the knowledge of what was coming, it was hard to convince my muscles to cooperate.

Relax. You want this.

I felt myself loosening. Unclenching. She could probably already tell, but I felt it was important to tell her through my pacifier: “Mommy, I’m yourth.”

She hummed in delight and began preparing my backdoor once again. This time, her finger tips entered me; slow and steady. I bit down on the pacifier, channeling all the energy I would’ve liked to have used for my sphincter muscles into my jaw. It seemed to work.

“That’s much better,” she said. “What a good boy. I think that should do it. What do you think? Are you ready for Mr. Purple?”

I couldn’t decide if I liked this toy having a name or not, or if I just disliked the name ‘Mr. Purple.’ What was the alternative, though? Hank? If there had to be a name, this was probably the best option.

I offered an affirmative moan in response to her question.

She was prepared–I could immediately feel the stiff tip of Mr. Purple pressed against my hole. How? How was this thing ever going to fit? But with just a little push from her, it slid into me.

“Ohhhhhhh…”

“I’ll assume that’s a good sound.”

“Yeethhh, Mommy.”

“I’m going to take it nice and slow, okay? Little by little. You tell me if I need to stop or remove it.”

“Mmhmm.”

True to her word, I felt the toy slide deeper into me. Toy? It seemed like an extension of her now. Mommy wasn’t using a toy. She was fucking me. Fucking me with her cock.

“Is this too much?”

“No… No, Mommy.”

“I’m going to keep going.”

“Pleath.”

I was losing comprehension of how deep she was now, and how much more of her cock there was to fit inside me. It almost didn’t matter–it felt all consuming. It filled me. Completed me. It was simultaneously overwhelming yet not enough. I can take more. I can take everything. I was likely overestimating my abilities to take a cock at this point. Yet I knew, for sure, that I was in love with what I was feeling at this moment. It was hitting all the nerves–nerves I wasn’t sure that I had ever had stimulated before.

“Unnnnnh,” I moaned, teeth still clenching the pacifier for dear life. “More. Mommy, more!”

“That’s exactly what I hoped to hear,” she said. “Look at my little baby, begging for more cock. Are you Mommy’s little butt-slut?”

“Unnh. Ohhhhhh.”

“I’ll accept that as a yes.”

I felt the cock reverse course, slowly pulling from bottom. Just as it had taken eons for her to fill me with it, it seemed to take forever to draw it back again. Again, it was hitting all those poor neglected nerves.

“M-more,” I stammered the best I could with my mouth still locked around the pacifier. I doubted I needed to let her know what I wanted, but it couldn’t hurt.

“That’s the hard part,” she said. “Now that you know you can take the whole thing, I can do it again…”

“Mm.”

“...and again…” She pushed it as deep into me, again, before sliding it back out.

“Mmmph.”

“...and again…” Another thrust.

“Unnnhhhh.”

“...and again…”

“Unnnnnnnnnnghhh. M-mommy…”

“Now that you’ve been introduced to the concept of getting fucked, we can talk about what’s next.”

Did I want whatever was next? I wasn’t even sure of anything anymore. I just wanted more. I didn’t care what it was. My own manhood, shriveled and locked away, could barely stand it, and I felt myself dribbling into the diaper–a near constant leak of anticipatory prec*m.

“It’s possible to make a boy c*m just by playing with his bottom. I don’t even have to touch his cock.”

“Mmm,” I moaned. “Pleath.”

“It doesn’t come easily,” she said, giggling. “Pardon the pun. But we’ll get you there in time. For tonight, that’s where this other toy comes into play.”

BRRRRRRRRRMMMMMM

I could hear the Magic Wand activate behind me with its electric hum. She hadn’t even touched me with it yet, and still felt like its energy was coursing through my body. She reached through my spread legs with the wand and held it against my cage.

Is this what it’s like to be electrocuted? I could barely even process the waves of pleasure that immediately began to ripple through my body. The cage only seemed to amplify its contact with me, spreading its pulses over a larger area.

“And while the wand works its magic on your cage,” she said, “I push Mr. Purple deep inside of you.”

“Unnh. Unnnnnh. Unnnnnnnnnnnhhhh… Fuuuuuck.”

It couldn’t have taken any longer than half a minute. Almost immediately, I felt my cock oozing into the diaper–an eruption fueled by two weeks of hopeless desperation. I lost all the strength in my entire body and I collapsed on the bed, shaking and whimpering like a pathetic baby as my cock continued to leak between my body and the diaper.

She slowly withdrew her cock from me for the last time. The human body, so I was told, was an incredibly versatile machine. I’m sure that my asshole would be fine in the long run. But at that moment, it felt like it was the size of a tunnel on the highway. She could park her car in my ass if she wanted to.

Her soft hands were on my back, cycling between massages and gentle strokes.

“Was that worth it?” she asked. “Did you get what you wanted?”

It took a few seconds to remember how to speak again, and the words that finally came out of my mouth were unfiltered and raw from the forefront of my brain: “Throw away the key.”