The Boss' Baby Part 7 - Terms and Conditions

“So what’d she say?” Stephanie asked as she applied mascara and eye shadow to my eyes in Charles’ office.

“Who?” I asked. Playing dumb.

“Your wife. About your diapers...”

“Oh...uh...yea that” I stammered, as if I forgot “she said I was a freak. That this was going to be a stain on our marriage. But she was willing to work with me if that’s what I wanted.”

Stephanie stopped applying the blush to my face to stare at me inquisitively. I quivered under her gaze.

“You’re lying.” She said finally.

“What? No! I-i...what are you doing?” I asked as she scooped up her phone.

“I’m sending your wife the video of you humping your wittle pissy Pampers yesterday!” She said, tapping through her phone. “Her number was in your emergency contact file...”

“No wait!” I exclaimed. Stephanie stopped tapping and looked up, smirking.

“I’ll...i’ll tell her tonight...” I said. Hanging my head.

“Tell her what exactly?” She asked, crooking an eyebrow.

“That...that I wear diapers now...and...do I need to tell her about Charles too?”

She thought on this for a second. “Hmm...no. At least, not unless Charles orders you to. For now, you will tell her about the diapers. And you will get a picture of her changing you as proof.”

I nodded as she had me purse my lips to apply bright red lipstick.

“Oh and just so you know...” she said offhandedly “Charles likes it if you play with his balls...”

*****

I left Charles’ office an hour and a half later with cum leaking into my diaper from my butthole.

Stephanie had stood witness as Charles came in, complemented her on getting my makeup good enough for me to be “fuckable”. Laughed as Charles bounced me on his knee with my plug in while he told me what a pretty baby gurl I was. Then helped administer the spankings after Charles’ made me suck him until he was hard enough to fuck my ass.

On my walk of shame back to my cubicle, I ran into Dave from IT. Who was standing there menacingly with his arms crossed.

“Hi Tom,” he said. “Can I see you in my office please?”

I spent the long walk to the IT wing running through a thousand different scenarios in my head. Dave was the one who had shown Charles the sissy porn on my work computer. Dave knew what I’d been looking at. Was he going to use that information to blackmail me too?

Dave’s office was secluded at the far end of the hallway.

“So,” I said, once we had both sat down. Trying to sound casual, “what’s this all about.”

Dave crossed his hands and stared at me for a good while. He was a tall, kind of scrawny white guy who probably laughs in the face of all the people who called him a ‘nerd’ in highschool that he’s now making three times the salary of.

I shifted in my seat from the silence. Hoping he didn’t hear the diaper crinkle under my suit.

“What the hell does she see in you?” He finally said.

“My wife? I...I'm not sure to be honest...” I chuckled awkwardly.

“Not your wife dumbass, Stephanie!” He said, his face flushing with rage.

Dave apparently saw from my demeanor that I was extremely confused. So he clarified: “I saw the two of you come out of the bathroom together yesterday. And then again this morning. Both times I heard your girly-sounding moans. So how long have you been fucking her?!”

I struggled for words. How was I supposed to explain to this guy that he's got it all wrong without giving up my secrets? You see, she was actually in there changing my pissy diapers! And the moaning you heard was the sound of me humping said diapers!

“You don’t understand...” I finally said, “it’s...it’s complicated...”

“Does she know you’re a sissy?” He said. Playing his card. “Does she know you look at this shit on the internet?!”

He clicked through his computer a few times and turned the monitor to show me a video of a sissy getting pounded from behind by a big black man. I decided not to tell him that was pretty much me about 15 minutes ago in Charles’ office.

“Stephanie and I are not together, Dave. We’re not fucking. We’re just...friends. She helps me with my makeup and gives me tips and stuff. That’s what we were doing in the girl’s bathroom...” I said. Not exactly lying.

He narrowed his eyes. “Then what about the moaning I heard?”

“That was me practicing my girly voice for when I....one day...get fucked in the ass. She said it needs to sound pathetic. Apparently guys like that...” I said, hanging my head convincingly.

Again Dave stared at me for a long while, but apparently he bought it. “Well...it definitely did sound pathetic. And your lips are still stained, like you had on makeup earlier, so it makes sense.” He said. Turning to his computer. “I’ve got a lot of dirt on you, so if you don’t want this to get leaked to the office or to your wife, you’re going to need to do something for me.”

“What...?” I asked. Tired of this stupid porn being held over my head.

“Get me a date with Stephanie.” Dave said. It wasn’t exactly what I was expecting, but it was better than having to suck his dick or something.

“I...I'm not sure I can do that...” I said.

“I thought you guys were friends?” Dave asked, eyebrow crooked.

“We...we are but...”

“You have until the end of this week before I leak your search history. I still haven’t been able to figure out why Charles’ hasn’t fired you yet. He seems to even be favoring you now with how much time you spend in his office...”

You have no idea...I thought.

“I’ll see what I can do...” I said. Taking my cue to leave. I was almost at the door when Dave stood up and stopped me.

“Not so fast.” He said, coming closer than social norms would deem comfortable. “Before you go...let’s see if you can suck dick as well as some of the sissies in those videos you watch...”

*****

“He wants to what?” Stephanie asked. Changing my diaper for the 2nd time that day.

“Go on a date with you.” I repeated. Trying not to get excited as she wiped the piss off my shriveling dick.

“I don’t know...” she said “he’s kind of weird. And why would he get you to ask me for him?”

“He thinks we’re friends....actually, he thinks we’re fucking.”

She roared with laughter. “Me?? Fucking you?! With this tiny dick?!!” She pinched the tip of my two inch flaccid penis. I blushed in shame. “His dick is probably as small as yours anyway...” she shrugged.

Actually it’s about 6.5 inches...and his cum tastes a little sweeter than Charles’ I thought.

“Will you just go out with him please?” I begged. I really didn’t need more people at the office knowing about my porn habits.

She pondered as she powdered me. “I tell you what: if you wear a chastity device in addition to your diapers. I’ll go on the date with Dave.”

My stomach dropped. Unfortunately with all the sissy porn I've seen, I knew exactly what a chastity device was, and exactly how much I didn’t want to wear one.

“But...my wife doesn’t even know I wear diapers yet!”

“Then I guess you’ll have a lot to break to her tonight...”

*****

“We need to talk.” My wife Amy said when I walked through the door.

It was weird, because it was exactly what I planned on saying.

“About what?” I asked.

“About how weird you’ve been acting lately.” She said firmly.

Oh god. I thought. She knows.

“Do you not find me attractive any more?” She asked, almost tearing up.

“What? No, Honey! You’re beautiful! Gorgeous! I just...”

“Well then what is it? Huh? Why can’t I get this dick of yours hard for me anymore?” She said it as she squeezed my crotch. The diaper I had on underneath crinkled. I was frozen. Recollection shined across her face. “Are-are you wearing a...?”

“Honey I can explain...” I stammered.

“A diaper?!” She finished. Pulling my pants down and exposing the big fluffy diaper with the letters “B A B Y” written across it.

“It’s a long story, now don’t be mad but...”

“Why would I be mad?” She said, smiling. It was not the reaction I expected. “You know how much I want a baby and you obviously feel guilty that you can’t give me one. So you thought dressing like one and wearing a diaper would make me feel better! That’s honestly really sweet! Weird....but sweet!” She laughed. Kissing me.

“That’s...that’s exactly right!” I said, going along with it.

“Is that why you’ve been wearing my panties too?” She asked. “Because you knew how much I’ve been wanting a girl?”

“I...what? You knew?!”

“Of course I knew!” She laughed. “You think I didn’t notice the way you’ve been wadding them up and stuffing them in panty drawer? I just wish you would have bought your own...you’re staining mine and stretching them out...”

I couldn’t believe how well she was taking all of this. “I’m glad you’re not mad. But there’s one more thing I've been thinking about: if I'm going to get you a real baby, I need to build up as much sperm as possible until you’re ovulating again.”

She pondered this for a while. “Okay so no sex until then. But that means you can’t touch yourself until then either!” She laughed at that, knowing how preposterous that sounded. “You don’t have that much self-control.”

“Actually...there are ways to keep me from cumming until you need me to...” I said, dreading it.

“And how is that?” She asked.

“Have you ever heard of this thing called a ‘chastity device’?”