The Boss' Baby - Epilogue

Author’s Note: I started this story over two years ago. It started out as a small little idea about a man that gets dominated, sissified, and cuckolded by his Boss. I thought it would be a fun little chapter or two to add to my blog. I had no idea it would become so popular. People were messaging me every week asking for a new chapter. So I wrote as best I could with no clear idea of where the story would go. As the real world became more demanding, my ability to write this story suffered. A feedback loop of more people wanting more Chapters and even some very unkind words caused me to feel the most self-conscious I ever have as a creator. Eventually the stress of trying to churn something out was so great I ended up abandoning the story altogether.  Then another nail hit the coffin: my Tumblr got deleted. It felt like a meteor came and destroyed my world. All the posts, captions, and stories I’d written were gone in a flash. Once I got over the initial loss and depression, my creative juices started churning again. But I had no outlet, no Tumblr to post to, no pictures to caption. All I had, tucked away in my Google Drive, was the Boss Baby story I’d started years prior. So I picked up where I left off. I went back and edited/changed what I could, and started adding new bits to the story. It helped me get out of my slump. Helped me get the drive to write and produce content again, so I started a new Tumblr, a Patreon, and began writing more Boss Baby. I still had no clue where the story would go, or how it would end, and I struggled with that for a while. I’ve written and rewritten this Epilogue more times than I can count, and I’ve hated almost everything I came up with. What you’re about to read is the only iteration I’m somewhat happy with. I know people are going to hate it. People are going to want more, for it to go on forever, or for it to end with everything tied up nicely. I don’t think I can do any of those things. At the end of the day, I’m just an amateur writer with a blog for a very niche set of fetishes. This is the best I can do, so I really hope you enjoy it:

Epilogue - One Year Later

“Where are we headed, sir?” I asked between the sounds of gluck gluck gluck while I bobbed up and down on the cock of my new boss, George.

“A party” he replied, not looking up from the phone he was tapping away at. He touched a button on the side panel of the stretch limo to signal the driver.

“Yes sir?” the driver’s voice said over the intercom.

“Double time, please” George said, “We have other business to attend to.”

I felt the limo pick up speed as I lurched forward on my knees. Further onto George’s cock.

It had been almost a whole year since I was shipped off to the corporate office. I mostly did the same thing I did in Charles’ office. Except, instead of having one man to please and pleasure throughout the day, I had the whole 9th floor. I basically made my rounds to every cubicle or desk, climbed underneath, and got to work.

Most of them were old white men that either weren’t getting enough at home, or reveled in the power they had over me. Oftentimes it was both.

At nights, instead of going home I was taken to sleezy hotels or simply left in the “stables” with the other sissies in the corporate building. On weekends, I provide entertainment for prospective clients. Usually in the form of dancing, competitions, degrading and humiliating acts, anything to keep the old men satisfied and amused.  Much the same way concert/sports tickets are handed out, or golf trips are used to network, I’m simply an object used to “bring in business”. And ever since I got my boob job, business has been booming.  George tells me all the time that I am “one of his best new prospects” and that I “have a good head on my shoulders”. Not for thinking, mind you, they could care less about what I have to say. More about what I can do with my head and mouth on someone else’s head of their cock.

I have gotten several plastic surgeries to make me  look more like a pathetic bimbo. In addition to my new C-cups, I’ve gotten lip injections, ass injections, a face-lift, laser hair removal (which is actually really nice to not have to shave my entire body every day) and liposuction.

They let me keep my cock though, thankfully. They say having a set of cock and balls between my legs keeps me horny and eager to please. They tried castration on others and they basically just became shells of themselves. My dick is properly caged though. I can’t remember the last time it came off. What I wouldn’t give to have a full blown erection again, even if it would probably only be 2 inches when full-mast at this point.

I’ve gotten better at sissygasming. But it often takes me quite a while to do so. Usually whomever is using my ass is long done before then, leaving me frustrated and disappointed.

They also rarely have as good of a dick as Charles. I find myself missing Charles’ big, black, bulbous head and his veiny, triumphant shaft. Instead, it’s usually old, wrinkly white wiener and balls sprouting gray hairs. You would think that with less artillery down there that they would be more gentle in comparison to Charles. But they’re not. It’s like they’re trying to make up for their lack of endowment by being rougher and crueler to me.

Or, as in George’s case, they pay very little attention to me. Like I'm nothing but a warm mouth for him to use on his way to different events.

“We’re here,” he finally said after pumping his salty load in my mouth without so much as a grunt.

As I gulped down his load I looked up through the window of the limo to see my front lawn. The house Amy and I bought together after we first got married.

The front lawn was decorated with blue and pink balloons. The pink and blue reminded me of baby colors. Were they welcoming me back? Was I going to get to live with them again? I would gladly wear the diapers and be treated like a baby if it meant I could be back in my own house around my own wife.

The yard looked better than it ever did when I was living there. George seemed annoyed as he got out of the limo, like he had much better things he could be doing that day.

My heels clanked on the sidewalk, I had gotten much better at walking in them over the months. We made our way to the front door. It felt weird to be ringing the doorbell to my own house. I wanted to just walk in. But it had been so long that I felt like a stranger.

The door opened to a woman with long black hair. “Hi there!!” Gretchen said enthusiastically, until she saw who we were.

Gretchen has been Amy’s friend since college. I always got the feeling she never liked me. The look on her face right now confirmed my suspicions. Maybe it was the fact that I could never satisfy Amy. I could never give her the baby she wanted, the sex she desired, or the life she needed. Gretchen probably heard all of Amy’s complaints, but would always bottle up her feelings about me when I was around.

She spared none of my feelings this time. Turning up her nose and looking at me and my new breasts like I were the scum of the Earth.

“Everyone’s in the back,” she said. Not bothering to welcome me into my own house or even offer drinks or something.

The inside looked mostly the same as it did before, with the exception of all the pictures adorning the walls. The ones of me and Amy together were replaced by her and Charles. I couldn’t help but notice how much happier she looked in the pictures with him than she ever did with me.

George and I walked to the back. I was a little nervous with how many people were there. It’s always nerve racking when people see me for the first time. Well, people that aren’t paying for me, that is.

When I stepped outside, the crowd had the exact reaction I expected. Scattered whispers and hushed voices. All from people I once knew, or used to be friends with.

“That’s him”

“Him? Or ‘her’?”

“Oh my god! He looks so different!”

“No way that’s him!”

“You know, I always suspected…”

I tried to block it all out. Over this year, I’d learn to block out a lot of things. Instead, I focused on searching the lawn for Amy.

It didn’t take me long. Even in a crowd she always shined like a candle in a dark room. She was facing away from me, talking to a group of people I didn’t know. Perhaps some of Charles’ friends.

I awkwardly came up behind her as the group laughed at a joke I probably wouldn’t get. I gulped and tapped her on the shoulder.

She turned around with that radiant smile I hadn’t seen in ages. She looked a little caught off guard, but not as much as me when I saw her large, rotund, pregnant belly.

“Hello, Tommy” she said softly. Giggling at what must have been my extremely flabbergasted expression. The rest of the group behind her took the hint and their leave, while Amy and I stood there stiffly. “You look…so different!” she said.

“Yea uh…you do too.”

She smiled brightly and rubbed her very round belly affectionately, “yea…I guess so, huh?”

“Is it…is it…mine?” I asked hopefully, though I already knew the answer. Amy and I hadn’t had sex in over a year, and even when we were I was never able to give her what she always wanted. So she didn’t even feel the need to glorify me with a response. Instead I looked around at all the baby stuff, and suddenly it all made sense.

“You know it’s funny I…well, a small part of me thought this was all for me…” I said sheepishly, but it just made me feel more pathetic. “I’m sorry.” I muttered.

“For what?”

“For all of this, the sissy stuff, the diaper stuff, that I let…all of this happen.”

She looked at me for a long while, her eyes darting back and forth to each of mine. Finally she said: “I’m not.”

It caught me off guard. “You’re not?”

“No.” She smiled, and touched my arm affectionately for the first time in almost a year. “We both got what we wanted.” She smiled as she looked down and stroked her pregnant belly. “I’m gonna have a baby, and I get to be with a man that can provide for me, in all the ways that I need.”

Her words stung, but deep down, I knew them to be true. “But what about me? I wouldn’t say I got what I wanted...”

She scoffed at that. I looked up at her quizzically.

She laughed again, “Oh come on! I saw your search history! It’s what got you into this mess in the first place! Being a sissy is something you’ve always wanted! Sure...you may be faced with the harsh realities of it now, but I saw the way you were with Charles. I heard the sounds you made while you sucked and fucked him. You were made for this. It’s who you are, and you’ve finally gotten that.”

Again I was struck by the accuracy of her statements. I had been hiding my sissy desires since I was very young. I had always wished to be whisked away, feminized, and used as someone’s plaything. I never thought it would actually happen, and when it finally did, I’m not sure it was everything I imagined. I do like it, don’t get me wrong, but what is it they say about being careful what you wish for?

She put her hands on my shoulders and turned me around, whispering in my ear. “Charles is right over there, why don’t you go say ‘hi’ to him?”

I didn’t think seeing Charles would make my heart flutter more than it did for Amy, but it did. What was it about this man that made him so powerful and alluring? Amy gave me a kiss on the cheek before shoving me forward.

I stumbled a bit as I caught my balance. Heels on grass was never a great idea. I had to put most of my weight on my toes. As I walked through the crowd I noticed Stephanie, the secretary from my old office, standing there talking to Steve, the guy I used to fuck at the office when I was in desperate need of relief. She was holding a small leash that was attached to someone behind her. She tugged on it and out crawled Dave from IT. He was the guy that turned in my search history to Charles. Pretty much what got this whole thing started. Dave looked so feminine and skinny now that I hardly even recognized him. His outfit was ridiculous, a little pink frilly dress that did nothing to hide his very wet diaper. As I walked by, the smell alerted me to the fact that his diaper probably wasn’t just wet…

When I looked back to where I was going, Charles had disappeared. I felt my heart and stomach sink a bit, then felt an arm around me.

“Well hello there,” said a gruff voice. I immediately recognized my old Boss’ alpha cadence.

“H-hi Charles.” I said, trying to sound nonchalant, when really my heart was racing.

“How have you been?” he asked.

“I’m okay…”

“Just okay?”

“Well I’d be better if I could…maybe…move back in with you and Amy?” even in my head it sounded stupid, it sounded even more ridiculous when I squeaked it out loud.

“I’m afraid that’s out of my hands.” Charles shrugged unsympathetically, “You belong to George now.”

My head slumped and I did everything I could to hide my disappointed tears.

“Hey, cheer up,” Charles said, leaning in close, “Watta you say we go into the study and have a little…meeting. For old time’s sake?”

I tried to conceal my excitement, but I don’t think I did a very good job as I nodded enthusiastically.

“I’ll head that way, meet me there in 5 minutes,” he said.

******

I knocked on the door to what used to be my study.

“Come in.” came the deep, stern voice. I anxiously stepped inside, Charles was sitting behind the desk, it was all highly reminiscent of his office. “Close the blinds if you don’t mind.”

I followed his orders, the same way I did when I first stepped into his office over a year ago on the day that changed my life forever. My hands were quivering, my heart was thumping out of my chest, I don’t know why I was so nervous.

“Have a seat,” He said, and I did. He stared at me with those cold, searching eyes. Fingers interlaced under his chin. I’ve learned by now that he likes to let the silence hang, to establish dominance, but it didn’t make me any less uncomfortable.

“How are things going at the Corporate Office?” he finally asked.

“They’re…good.” I said, sort of surprised at my own words, “I think I’ve…finally found my place in life. Doing a ‘job’ I always wanted. I’m…happy.”

Charles smiled, “And you weren’t happy before?”

“I was. But not as happy as I could have been. I always dreamed of being a sissy slut and…I guess I finally achieved it. I was always having to hide my true nature, my true fantasies, and now I'm living them out. Well…mostly.  It’s definitely not everything I thought it would be, but…yea, I think I've finally found my place in life.”

I couldn’t believe the words coming out of my mouth. It was like I was coming to this realization all at once.

Charles chuckled, “Well, I’m glad I was able to help out.” He pushed his chair back and smiled, down at the tent forming in his slacks, “Perhaps…a ‘thank you’ is in order…”

My mouth immediately started watering, but I gulped it down and felt my face flush as I asked: “Could you…maybe um…spank me…first?”

He reared his head back and roared with laughter at that. Even I couldn’t help but shrug and laugh.

He beckoned me over behind the desk. My heels clanked as I teetered over. Both of our breathing was heavy and measured.

“Bend over.” he growled, getting into his dominant mode.

My body was quaking in excitement as I bent at the waist and laid flat over the desk. I felt his hands on my skirt, hiking it up, and rubbing my smooth buttocks. His huge, rough, warm hands made me tremble. He fingered my lacy pink panties a bit, but didn’t remove them. He liked the visual. Then I felt his hand smack against my ass.

“Oh! Thank you sir!” I bellowed.

With each successive spank my voice got progressively higher-pitched and more pathetic. I was able to take a lot more than I used to. In fact, he was the one to tire out first. My ass was red and bruised by the time he was finished, but I could have handled much more. I missed the feeling of his rough, gruff hands on my thighs. Even after all the hands that have groped me over the past year, they were all impersonal, more unsure, or too sure. Charles’ felt just right.

“On your knees.” He commanded, and I immediately obeyed.

It felt like old times. I was jittering from the anticipation. Seeing the bulge in his pants. I drooled over the prospect.

He smiled that knowing smile, relishing the power he has over me as he unzipped his fly. My breathing quickened as I anxiously awaited the reemergence of the first cock I've ever sucked.

There have been many since then, but none as beautiful as his. The veiny, bulging, black shaft and his bulbous, throbbing head. I waited there, mouth hung open, in awe of its presence. Like a God needing to be worshiped, he gave me a slight nod that was all the permission I needed.

They say that smell is the strongest sense tied to memory, and I believe it, because just the scent of his skin instantly brought me back to a year prior, when I was on my knees in his office about to perform the exact same act. Oh how i’ve grown since then, but conversely find myself missing my more naive former self.

I expertly slid my tongue around his balls, reveling at the taste. Like a dessert you haven’t had in ages. Tracing my tongue all the way up the veins of his shaft until I was running it under his frenulum, the sensitive spot under the head of his cock that I was now sucking on like a popsicle. I listened to him groan, how I missed making him make that sound, ignoring the fact that Amy always made him groan louder.

He pulled on my pigtails, my hair so naturally long now he could practically steer it any way he wanted. I was able to take his shaft down my throat with ease and very minimal gagging. Even slipping my tongue out to lick his balls while his cock was still down my esophagus.

“Look at how much you’ve grown!” Charles moaned in ecstasy. He was never much for compliments when it came to me, so this revelation of his gave me butterflies.

I could feel him swelling, his breathing quickening. I was so excited to get his load. But he stopped me. Yanking me by the hair off of his cock.

He stood me up off of my knees and flipped me around, shoving me over the desk again.

It was like we were conducting our old ritual again. I was panting like a bitch in heat over his desk because I knew what was coming. He hiked my skirt so that my rosy red cheeks were exposed to the cool air. He groped them, spread them, like he was inspecting meat at the market. I could feel my hole puckering for him, winking at him. I felt his spit run down my crack. The crackling of his cock as he stroked it with the saliva I'd slobbered on him. I felt his hand on my lower back, pushing up my top.

“I see you got a new tattoo…” he chuckled, which made me cringe. “ Your Cock Here “ He read, tracing the arrow of the tattoo down my crack and between my cheeks. He spread them, pressed his thumb into my hole, listened to me inhale and exhale sharply. Then he put the head of his dick where the arrow indicated, and entered.

There used to be a slight pain as someone slid their dick into me. But not anymore. Not with Charles. My body welcomed him like a flower wanting to be pollinated, and I felt nothing but bliss as he pushed his cock into my asshole.

“Ohhh my god…” I gasped, not realizing how much I truly missed his dick until now. It was a mixture of euphoria and nostalgia. With every thrust, it was like a light was going on and off in my head. Like I was in a vortex of exhilaration. He started pumping and pounding me, and I jammed my hips back into him in rhythm, begging for more with my body.

I felt a sissygasm building almost instantly, I reached my hand between my legs to catch my load shooting through my cage. I wasn’t about to cum all over his floors again, even though they were technically my floors. I caught my puddle as my cage flopped everywhere. I immediately brought the warm goo to my mouth and licked my hands clean. Feeling like a drug addict getting her fix.

Without breaking rhythm, Charles pulled open a drawer beside me. Pulling out a large stack of papers. He plopped them on the desk in front of me. “These are the deeds to your estate,” he said between breaths, “you are going to sign them over to me.”

I whimpered as he placed a pen down next to me. I wasn’t about to argue, not while this was going on. Plus, what would I even say? It’s not like I was using the house anymore, I was busy spending my days getting used at the corporate office or in hotel rooms. He placed a pen next to it, it took me three attempts to grab it with my sticky hands amidst the shaking of my body as he fucked me. He slowed his rhythm long enough to allow me to sign and initial the necessary pages. Then I got to the last file.

“What is this?” I asked.

“Divorce papers.”

My heart dropped. All the feelings of pleasure before now forgotten as I thought about Amy. Our marriage throughout the years wasn’t perfect, far from it, but we still loved each other, even if we couldn’t fully fulfill each others’ desires.

“She will never see you as a man again” he said, as if reading my thoughts. “Things will never go back to the way they were before, and even if they could, would you really want them to?”

He was right, as always. After spending so long changing my dirty diapers, watching me suck and get fucked by Charles, wear skimpy dresses, and all the other things Amy saw me do, there was no way she would ever be able to think of me as the ‘man’ I once was. Our lives had taken a new direction, and we were both better off for it.

I scratched my signature over the lines of the papers. Feeling surprisingly melancholy about the whole thing. But Charles must have been elated. As soon I completed signing off on my wife and I’s divorce he began fucking me with renewed vigor. My current problems forgotten, all I could do was focus on the amazing feeling of his dick sliding in and out of me. Pounding me in the prostate and making me squeal the sissy girl I was.

I could feel us both building to orgasm now. His dick and my prostate doing that telltale pulse. Our breaths quickening, becoming more labored until both of us were grunting and grinding against each other. I came first, of course, another load in my hand as he began exploding inside of me.

Then the door opened.

“I figured I’d find you both in here.” Amy laughed and stepped in as if nothing were amiss. Charles slid out of me, leaving me panting over the desk with two loads leaking out of me.

“Did you get him to sign the papers?” she asked, and Charles smiled victoriously. Amy clapped her hands in glee and came around me to give Charles as much of a hug and kiss as her pregnant belly would allow.

“You just couldn’t contain yourself could you?” she said, smacking my ass. I wasn’t sure if her comment was directed more at me or him, no one seemed to care, as we all laughed heartily.

“I brought this from upstairs,” Amy said, she was holding one of my old Adult Diapers. “I found them when I was cleaning out his nursery the other day to make room for the new baby’s!”

She handed the diaper to Charles. He looked at it in bewilderment. “What do you want me to do with this?”

“I want you to put it on him!” She smiled and nodded over at me, then smacked his ass affectionately with a wink, “You need the practice!”

Charles chuckled sheepishly as he awkwardly took the diaper. It was the first time I had ever seen him look even a bit unsure. He opened it up like a newspaper he was about to read, then looked up at me with the diaper spread between both his hands. “Uh…well um…lay back then.” he said.

I turned around and laid my back onto the desk. Still cupping the load in my hands from before. I felt so silly as I lapped it up like a kitten while Charles used one hand to grab me by the ankles and lift my backside up so he could slide the diaper underneath. My hole was still leaking his load, which now ran down my crack and into the padding of the diaper. Amy handed him the wipes and powder. In all the times Charles and I spent together, the closest his hand ever got to my genitals was just now when he was rubbing a baby wipe over my cage and cleaning the sticky residue. He kept looking to Amy for reassurance, but she just stood with her hands on her prominent belly with a huge, loving smile on her face. Charles applied (a little too much of) the powder, and then brought the front of the diaper up and over my waist.  He gave a small sigh of relief, probably from realizing he had indeed oriented the diaper correctly and not put it on backwards.  He put the tapes on, a little too tightly for my taste, but I was surprised at how good it felt to be in a diaper again. Like a small comfort of what used to be.

When he finished Amy gave him a proud kiss on the cheek, “Good job, babe!” she said to him, “Now come on! We need to get back to the guests! It’s time to open presents!”

They headed for the door, Charles opened it for her and let her step through the threshold. Amy stopped, and turned around.

“Goodbye Tom,” she said, looking at me a bit pityingly,  “I hope you have the life you always dreamed of!” Charles simply shrugged and nodded.

They both left without another word. I watched as they made their way through the house and to the backyard to join the rest of the gathering. I watched from afar as they clutched each other lovingly and laughed with their peers. I watched how happy and excited they seemed to open the presents for their new, future offspring. I watched how the life I thought I’d always have felt more and more like it wasn’t for me.

George came up next to me and gave me a quizzitory look. “Are you wearing those stupid diapers again?”

I just shrugged and said “Yes sir, I’ll make sure to remove it as soon as we get in the car.”

He nodded, checking his very expensive watch, “Well it’s time to go. Do you want to say your goodbyes?”

I stared out once more at the happy couple. Then I shook my head. There was nothing I could say that hadn’t been said already, there was nothing I could do to change the situation. This was the path I went down, the path my subconscious ultimately took me down.

I turned around and headed back through the house with George, leaving the life I thought I wanted behind, and the life I actually wanted ahead of me.

THE END