My boss is a woman(Private w/elfowl)

[Daddydrew]

Andrew was starting his Thursday morning like any other morning. Making coffee and checking emails. His job was a secretary for a good sized company and his boss was one of the higher ups. He had been working for the company for a little over 2 months and always found it odd that his boss wanted a guy secretary. You see his boss was a guy as well and Andrew had suspicions that his boss had a thing for him. Maybe it was due to his small size, Andrew was just over 4'6 and was skinny to boot. His boss always called him nicknames like cutie, honey, and it didn't really bother him at first. But lately his boss has been a lot more touchy lately. Hands on Andrew's shoulders and the other day he groped Andrew when he bent over to pick up some papers. Andrew wanted to go to HR about this but he felt that he had an understanding with his boss after this incident. Besides he had a pretty easy job that paid well, so he didn't want to risk loosing it. Andrew was replying to email and waiting for his boss to arrive.

[elfowl]

Driving my black SUV into the company parking garage, I pull into my executive parking spot close to the door.  I turn off the car, and simply sit in the driver's seat for a few moments, feeling lonely and unfulfilled.  I was getting older, and while I had been quite successful at my job, I had nothing to show for it in a relationship,  And one very important thing was missing in my life; children.  Thinking things over, and feeling sorry for myself, I realize that I'm longing for something deeper than that.  I didn't just want children.  I wanted to be a mother.  The realization hits me hard, and another realization comes along with it.  I have to do something about this.  

I stand up, grabbing my briefcase from the passenger seat, and walk inside.  I take the elevator up, and walk past the rows of cubicles to my office.  Walking past the first door into the lobby of my office, I arrive at Andrew's desk.  Andrew's a fine young man, and the main thing that's kept me going the past few months.  He's an absolute cutie, an adorable pint-sized package.  I can't help but smile when I see him.  "Good morning Andrew Honey."  I say, putting a hand on his shoulder, and giving him a quick rubbing massage.  "How are we looking this morning?"  I ask, feeling happier just from seeing him.

As I listen to Andrew's response, a thought occurs to me.  It's a very devious, and deviant though, but immediately I realize that it's caught fire in my brain.  It will be tricky, and I'll need to be very careful and meticulous about it.  But I want to be a mother, and I want Andrew to be my child.  Somehow, "son" doesn't seem right, but child does.  "Andrew, you're a fantastic worker, and you've really really been an asset to me over the years  Would you let me treat you to dinner tonight?  I think you deserve it."

[Daddydrew]

Andrew's shoulders get tense as his boss was rubbing his shoulders. He tried to gradually sink away but his hands were too large for him to slip out of. "Good morning sir, everything is going alright, nothing too major. Though you do have a meeting in 20 minutes."

"Oh, thank you sir. That would be really nice. I haven't been able to really go out much since I am still new to the town. Not sure what's good around here. Um where were you thinking?" Andrew replied as this took his mind off of his shoulders.

[elfowl]

I sigh and frown at the though of another boring and pointless meeting.  If I had my way I'd simply spend all day in my office, working with Andrew.  "Right thanks for the reminder.

I smile when Andrew seems receptive to my suggestion of dinner.  "I was thinking I would cook for you actually.  I live alone and cooking just for one isn't much fun usually.  I've got a new chicken dish I've been wanting to try out, I'm sure it will be delicious though.  I also wanted to talk to you about a few things concerning my future, your future, your position, and the future of the company, and it would probably be better if we talked about these things in private.  So what do you say?  I can take you to my place after work, and we can have dinner there.  Would that be alright?"  I fix Andrew with a long look, one that says 'don't say no.'

[Daddydrew]

A few thoughts went into Andrew's head, "could this be a raise? Is something happening with the company?" He was thinking. Andrew was curious and wanting to accept, he was getting really good praise so he figured it had to be good news. However the idea of going to his bosses house alone with him was nerve wracking. Was this some ploy to get in bed with him, it wasn't like Andrew would be able to say no. His boss towered over him and always made Andrew feel so much smaller.

Thinking it over for a minute he replied, "Well sir, I uh am flattered but...I don't" Andrew then stopped as he looked up to his boss, he looked into his eyes and felt this overwhelming pressure to say yes. "I..I mean yes I would love to. Chicken sounds really good. besides it will be nice not taking the bus home.ha.."

[elfowl]

I smile, a little bit triumphantly and pat Andrew's shoulder fondly as he agrees to dinner.  "Good boy, I'm sure you'll enjoy it, and we'll have a lot to talk about.  You certainly won't regret it.  I'm going to take you far Sweetheart, just trust me."  I walk into my office with a satisfied sigh.  Tonight I was going to tell Andrew everything, and after that I was going to make him mine, one way or another.  I was going to become a woman, I was going to become a Mommy, and Andrew would be my little baby.

I soar easily through the usual drudge of morning e-mails, leftovers from last night, as well as new, and routine issues of the morning.  Nineteen minutes later, I was off for the meeting, a fresh cup of coffee in my hand courtesy of Andrew.  I felt a great weight had been lifted from me, and my spirits were soaring high.

[Daddydrew]

Andrew nodded and slightly rolled his eyes at the nicknames he is being called. The rest of the work day went normally, however Andrew's boss was in a great mood. Every time he passed Andrew he was in great spirits and Andrew kind of like how happy his boss was. Andrew had a very good feeling about tonight.

Finally Andrew was sending out the last of his emails as he was getting ready to leave work for the day and join his boss for dinner. Andrew was both nervous and excited about tonight. He was hoping for a big raise, maybe work from home. But he was so curious about all the news his boss wanted to tell him. Andrew send his boss a gchat from his computer saying he was done for the day. Andrew turned off his computer and leaned back in his seat and went on his phone, waiting for his boss to be done.

[elfowl]

I smile when I see Andrew's message, and try to hurry to get done myself.  A few minutes later, I shut down my computer for the day, and step out of my office.  "All ready to go for the day?"  I ask happily.  I'm more than ready to bring Andrew home with me.  "Let's be off then, we've got a lot to discuss."  I wrap an arm around his small shoulders, and guide him to the elevator, taking it down to the parking decks.  I lead him to my large, black, luxury, SUV, and open the passenger side door, to let him in, then walk around to the driver's side, and get in as well.  "Make sure you're buckled up Honey,  I'd never forgive myself if I got in a wreck and I lost you."  I say, not starting the car until I'm sure he's secure.

I pull out onto the road, and start asking questions.  "So, do you live by yourself Andrew?  Is your family local?  Any close friends or relatives?  Do you have any pets?"   I let a short silence fall between us, then ask "Do you want to get right into the important parts, or do you want to relax for a bit first, and then talk about them over dinner?"  I find myself driving a little bit more slowly, and with a little bit more caution than normal, as I make my way out of the city.

[Daddydrew]

Andrew nods as he packs up his laptop and puts his bag over his shoulder. He feels a giant arm wrap around his shoulder as his heart skips a beat. He see's his bosses arm as he is guiding him to the elevator. He kept his head down, hoping no one would see this. Lucky for Andrew, he was shorter than most of the cubicles so not anyone would really see them. Andrew's eyes went huge as he saw the SUV, "This has to be the biggest car I have ever seen!" He then had to lift himself up to the passenger seat. He buckled up as he was told, but he felt so small in this large car.

 

"Oh, I do live by myself. No my family lives a few states over, I haven't seen or talked to them much after college. I am thinking about getting a cat though, would be nice to have something show me some affection haha." Andrew said as he went silent. "Well I am very curious sir, I know you have been complimenting a lot lately...am I...am I getting a raise? Is the company doing ok?"

[elfowl]

I laugh as Andrew marvels at the size of my car.  "I hope you don't think I'm compensating for something,  I'd hate to have to prove otherwise, and then get in trouble."  I joke.

Everything with Andrew just keeps getting better and better.  When he mentions a cat, I have to stop myself from telling him to pick me, and that I'll give him all the affection that he could ever want.  Andrew's quite smart, and very direct.  His questions cut straight to the heart of the matter.  "The company is doing just fine, profits are up, and there are no major roadbumps in the foreseeable future.  Honestly I wouldn't even be considering what I'm about to do if that weren't the case.  I have been very impressed with your work, and I want to make sure that you stay with me Andrew.  You're smart, have a good amount of self-discipline, and you work fast.  It also doesn't hurt that you're very easy on the eyes, and cute as a button.  I want to give you a raise, a very big raise, so that if anyone else wants to take you they'll have to think long and hard about it, but I need to make sure I have your support for what I'm about to do, and your commitment to me.  Do you understand?  I'm a lonely man Andrew, I've got plenty of political and business allies, but there's no one that I have a true friendship with, no one who would support me emotionally when things really hit the fan, no one that I can rely on, even when things get tough.  No one except you Andrew.  I'm about to do something really big, and I want you to be with me while I do it.  Once I tell you, you have to keep quiet about it to everyone until I'm ready to reveal it to the whole world.  Can I count on you for that Andrew?

[Daddydrew]

Andrew let out a few sarcastic laughs saying, "Ya that might be hard to explain."

Andrew kept smiling while his ego kept getting bigger, all the compliments he was getting was making him blush a little but get excited as well. That was until his boss was telling him he was cute as a button. "Oh thanks sir...um I guess your easy on the eyes too." Andrew said a little awkwardly. Andrew's heart was beating a million miles a second, was he right in assuming that his boss had feelings for him, what was he saying. "Sir I don't know what to say, I mean i'm glad you think of me that way but I...I don't know what to say." Breathing heavily, Andrew wanted to see where this was going. "Sir...I uh...yes I won't tell anyone I promise. You...you can count on me sir." Andrew felt a responsibility to hear our his boss, after all he had given Andrew such an opportunity and has been nothing but supportive.

 

[elfowl]

My heart skips a beat, and I have to concentrate to keep us on the road for a moment when Andrew says I'm easy on the eyes too.  My heart only beats faster when Andrew promises that I can depend on him, and that he won't tell anyone.

I take a deep breath and steel my nerves.  "Like I said before Andrew, I"m a lonely man, and quite rankly, I'm not happy as a man.  I want to become a woman.  I'm going to go on hormones, and begin to transition, and I want you to be there for me while I do.  To that end, I want you to move in with me.  I know it's asking a lot, but I will give you a raise, and quadruple your salary, I will cover your living expenses completely, and I will make sure there's a good position available to you when I retire."  I keep staring straight ahead, not daring to look at Andrew and see his reaction.

[Daddydrew]

Andrew doesn't move, he grabs his pants to make sure he isn't dreaming. There is so much to take in right now, he wants to support his boss while also realizing he would be making a huge life change, but that money is also hard to pass on. Taking a few breaths and not making eye contact, he says,"Si...sir I am...so happy for your decision on transitioning and I want to support you in that. But moving in...that salary...how can I say no." After another minute Andrew slowly turns to his boss who is so intense and seems to be shaking. Andrew looks away, closes his eyes and say, "Sir, if you  think I am the only person you can rely on...and..and..you need me for something like this. I...I accept your offer and will do anything I can to help you with this. Besides I am not someone who goes out much so staying inside should be a breeze..ha...ha"

[elfowl]

I want to reach out and hug Andrew tight, but I have to keep driving, so I settle, for simply reaching over and putting a hand on his thigh.  "Thank you so much Sweetheart, you have no idea how much this means to me.  I'll make it worth it to you.  I promise."  I do my best to keep it together, but a few tears manage to slip out of my eyes.  I wipe them away quickly.

After a while I pull off of the main road, and drive past the edge of the suburbs.  My house is located just outside where the housing development has slowly spread to.  I had bought the land when it was very cheap, and as the city sprawled ever closer, my property value hand only climbed higher and higher.  The house itself was huge, even for my standards.  a Five bedroom, four and a half bath monster of a small mansion, it was done in stone, in a neo-Gothic style, with three floors.  I pull up the circular drive, parking my SUV behind my sports car, and get out, quickly walking around, and opening the passenger side door to let Andrew out.  I open my arms wide to give him a big hug, essentially lifting him, out and setting him down on the ground when I'm done.

[Daddydrew]

Andrew, still unsure on how to feel about all of this. He see's his boss get a little emotional and replies, "Of course sir, I mean I only want to help with this. You gave me a great job and..and of course. I know it wasn't easy for you to tell me this. But I promise I won't tell a soul.

Looking at the road, Andrew was seeing a lot of construction still going on. But when they pulled up, Andrew's jar almost dropped at the sight of the house. He had only seen houses like this on TV and couldn't actually believe his boss lived here. Maybe staying here wouldn't be so bad. He then saw the sports cars in the driveway, maybe he could convince his boss to let him take them for a test drive. When they park, his boss basically jumps out of the car and comes to the side. Andrew a little jumpy doesn't expect to be lifted out of the car the way he is. "Woah, uh thank you for that. But I'm glad I can help again. This place is amazing! It's like something out of a movie."

[elfowl]

I smile happily as Andrew compliments my home.  "It's even better from the inside Honey.  Would you like to come see?"  Withou really thinking about it, I take his hand, and start to lead him into my house.

I lead him past the hedges and statues of mythological heroes and beasts lining the walkway to the door form the driveway, unlocking the door with my thumbprint.  The door opens to reveal a foyer with a grand staircase leading up to a railed walkway that curves around both sides of the two story room, with pairs of doors flanking both sides of the stairs, leading to other rooms.  "Take off your shoes if you want to go upstairs Sweetheart, let's keep the carpets clean, okay?  I'm going to go start making dinner, but you can explore if you would like."  I tell him.  "You'd probably like the den upstairs, or the living room down here where the bigger TV is."  I suggest

[Daddydrew]

"Well sure...I" Andrew let out as he was basically dragged into the house by the much taller man.

Andrew's jaw dropped bigger than it ever had before. He was looking at the most spacious and grand house he had ever seen. The walls were decorated so well, the ceilings were so high. He felt like Richie Rich or like he had just won the lotto. "Oh sure." Andrew said as he took off his shoes. He was so excited to see the whole house. "I uh, I'll start in the living room hehe." Andrew said as he ran into the living room. It was huge, the TV itself was bigger than Andrew himself. There was a huge fireplace to match, with speaks and a shelf of books. Not too mention a nice collection of wine. He turned and saw the couch, which seemed to be 25 feet wide. Everything was so huge. Andrew didn't know what to do first, "Uh sir, how do you turn on the TV out here?" Andrew said s he picked up the giant remote.

[elfowl]

I smile, absolutely loving Andrew's reactions to my house.  I smile and quietly praise Andrew as he takes off his shoes, leaving mine on.  "Good boy.  Thank you very much Sweetheart."

"Just say 'TV On.'  Then tell it what you want to watch,  it's hooked up to Cable, Satellite, Netflix, YouTube, and any other streaming service you can name."  I call out from the kitchen, starting to cook, turning the oven on, and preparing the chicken.

"What do you want to drink?  I have water, milk, juice, tea, coffee, and soda."  I ask as I set the rice, and broccoli on to cook so they'll be ready along with the chicken.

[Daddydrew]

Andrew is beyond amazed, he can't stop oooh and awww at everything. He goes to House Hunters as that is something he watches a lot. the quality and detail are amazing. "This is so cool!!!" Andrew yells from the living room.

"Oh, well I see you have a good selection of wine, do you think I could have some of that? I mean...uh, if not i'll take water please." Andrew replies

[elfowl]

"I'd prefer we stay out of that tonight.  I keep that around for parties, and important business guests."  I call out.  "I'll just fix us both some water."

I finish cooking Dinner, and load the chicken, rice and broccoli onto two plates, then set them at the table.  I pour two glasses of water, and slip a very powerful diuretic into Andrew's drink.  I sit down at the table, then call out.  "Andrew Honey, Dinner's ready.  Turn off the TV, wash your hands, and come eat."

[Daddydrew]

Andrew was a little bummed but said, "Aw man...ok I understand. Water is good then.

Andrew was so into the TV that he barely heard his boss call for him. "Hmm, what? Oh ok." Andrew turned off the TV then tried to find  a restroom to wash his hands. After his 3rd try he found one. After washing his hands he headed towards the kitchen. The kitchen was amazing, it was so open and big It felt like you could easily fit 20 plus people in here. "Oh smokes this area is huge. Uh where do you want me to sit? Is any seat fine?"

[elfowl]

After the second time Andrew goes in to the wrong door.  I call out.  "Do you need help?"  Luckily he seems to find it shortly after.

When Andrew asks where to sit, I motion to the place that I set out for him with food on the plate.  "You can sit wherever you would like, but if you want to eat, I'd suggest that place."  I then laugh.  "You don't have to sit there if you don't want, just move your plate wherever you would like to sit."

I dig into the food, and after a few minutes, ask Andrew.  "Well, what do you think?"

[Daddydrew]

Andrew, not wanting to be rude, took the seat that had his food set out for him. Although he had to climb up onto the chair to be able to sit on it. He saw his boss dig in so he decided to as well. As soon as the food touched his tongue he couldn't help but let out a huge "mmmm".

"Oh sir this is delicious, like really." Andrew said as he was shoveling his food into his mouth. "Your house is amazing too, it's soooo big and cool." Andrew said as he continued to eat.

He was curious though, "So sir, I want to help you with your transition. But what can I do to help? Just take calls and emails? Not sure how much I can help?"

 

[elfowl]

I smile, it's amazing how childish Andrew acts already.  There won't need to be too much change to make him into my baby girl, really all it will need to be is taking his mindset, and mannerisms down by about five years it seems.

"I'm really glad you like it Sweetheart."  

I can't help but laugh a little as Andrew asks what he can do to help me transition.  "Well being my secretary is a good start, but an even better start would be to start calling me Ma'am instead of Sir."  I tease.  "Really what I'm looking for from you, and what I'm going to need a lot of, is emotional support.  I'm going to need a lot of hugs, and physical contact, probably words of affirmation and reassurance.  Do you think you can help with that Honey?"

[Daddydrew]

Andrew looked up and said,"Oh, yes I can do that si...I mean Ma'am. That might take a little getting use to. But I mean hugs and physical contact doesn't sound too bad. I can definitely do with you Ma'am. I have no problem helping you out there, especially if you keep making this kind of yummy food." Andrew continued to dig in as he was starting to get really full.