My boss is a woman(Private w/elfowl)

[Daddydrew]

Andrew then looked away from his boss and closed his eyes as he was been stroked off. It felt so good to Andrew, his boss really knew how to work his tiny cock. The whole time he was moaning, twitching, and breathing heavily with every stroke. Then when his boss started the mommy talk it turned him on even more, along with the sweet and kind words. "It feels..it feels so good! Oh god..mo...mommy!" Andrew said as he started to cum, not realizing at first he had just yelled out mommy to his boss. Andrew didn't last long, he could barely lost on his own.

[elfowl]

It's hard to stroke Andrew off properly with how small his cock is, but luckily that doesn't seem to matter, as he's cumming into my hand and the water very quickly.  I lean in and kiss his forehead as he comes down from his climax, his tiny penis cumming into the water, as his petite purse pulls his marbles up close to his body, and shoots their contents through his system.  "Such a good little thing you are Sweetheart.  Making cummies for Mommy.  You're absolutely precious Honey.  You really liked that a lot huh?  It's okay, you don't have to be embarrassed about it at all, there's nothing wrong with it.

"You ready to get out?  Or do you wanna play in the cummy water a bit more darling?"  I ask, framing both options as equally viable choices.

[Daddydrew]

As Andrew is coming down form cloud 9, he slowly starts to realize his situation. Not only had he just let his boss jerk him off, but he called her mommy too. Then as he talk to him he sees the pool of cum in front of him. Andrew responds, "No I don...I mean it felt really greats..but I." He pause for a second saying, "I'm sorry for calling you mommy, we can go back to Ma'am please."

After being asked Andrew replied, "Well I..(looking into the water). I think I' ready to get out please." He then starts to stand up as he tries to get out of the tub.

[elfowl]

I smile, delighting in Andrew's slow realization of everything that happened.  When he apologizes I wave him off.  "No need to apologize Dear, I actually quite liked it. In fact, I'd like it very much if you kept calling me Mommy."

I grab a big fluffy towel I had set off to the side, and unfold it as Andrew stands up.  As soon as he steps out, I'm waiting for him with arms held wide, and wrap him up in the towel, drying him all over, making sure to dry inside his legs, his crotch, between his butt cheeks, and behind his ears.  As soon as he seems to be all dry, I wrap him up tightly in the towel, essentially using it as a swaddling blanket, to wrap him snugly.  "Alright let me take you to the clothes I say, as I sweep him off his feet, and carry him into the little girl's guest room.  I lay him down on the bed, to let him wriggle out of the swaddle on his own if he wants as I go to the closet, and pull out all of the dresses that my "niece" had left behind.  There's a simple little girl's party dress in each of the primary and secondary colors, pink, and white,  The main difference is the picture printed onto the bodice and skirt.  There's a wide variety from hearts, to "Mommy's girl, to a silver unicorn, to flowers, to butterflies, and a few others.  I lay out the dresses and ask Andrew.  "Which one do you want?"

[Daddydrew]

"Oh really? Um, well I guess that's ok then." Andrew said thinking that since it would just be them 2 for awhile that it wouldn't be a big deal.

Andrew let his boss dry him off. She was very quick and clean about it, he was dry within a minute. However he was expecting to be wrapped up the way he was. When his boss picked him up he said, "Oh you don;t have to keep carrying me I can walk too." His words did nothing as he was carried into the other room. As he was placed on the bed, he sat up and wiggle a bit out of the towel as only his privates were covered. His eyes went huge at the "selection" of dresses to choose from."Which one? Ma'am...I mean...mommy. Don't you have anything else I can wear? At all?" Andrew asked. Andrew wondered how old this niece was, she couldn't have been older than 2. "Geez, I..I guess...I guess the one with flowers on it? I don't know." Andrew sad in embarrassment.

[elfowl]

I shrug as Andrew tells me I don't have to carry him.  "I like carrying you, and you're really easy to carry, you're quite light.

I frown and shake my head "No" as Andrew asks if I have anything else he can wear.  "Everything else I have would be way too big on you."  I nod when he picks out the blue dress with flowers on it.  "Okay, seems good.  Now, I'm not sure if you'll like this next part."  I go to the closet, and pull out an open package of little girls' goodnite pullups.  They have prints of princesses on them.  "since you had an accident, and such a big one at that.  I want you to wear these.  I don't really have any other underwear for you anyways, and I don't want you making a mess on my carpet, or my niece's dress either.  In fact, you wet so much before, that I want you to wear two of these, just to be safe.  I know, I know, 'it was an accident'  but just to be safe.  If you can go 24 hours without making another mess, I'll let you go back into regular underwear, okay?"

[Daddydrew]

"What no, no no...please no. The dress is bad enough enough, but pullups?" Andrew said in a slight panic. It made it worst since all of this was for a little girl, not a grown man like himself. He also blushed at the comment of not having an accident on the dress or carpet. He wanted to rebuttable but figured she had a point.After hearing the condition and knowing that he was in no position to argue he said, "24 hours an I get my clothes back?...I guess that's kinda fair. an you wash my clothes though? That way I can wear them again tomorrow after the 24 hours are up?"

[elfowl]

I stand firm as Andrew pleads with me.  "I'm afraid it has to be this."  I'm amazed when Andrew takes my words a diffrent way than I was intending.  I had planned on giving most of his clothes back tomorrow, before work, but since he was agreeing to going the full 24 hours without them, I wasn't about to correct him.  Of course, I wasn't going to let him go 24 hours without an accident either.  "Yes, I'll wash your clothes, and you'll have them back in exactly 24 hours, if you can not have another accident by then."

I pull a pullup out of the package, then fluff it out, and hold it open down near the floor for Andrew.  "Step into these please, so Mommy can get them on you Sweetheart."

[Daddydrew]

"Great, I assure you I won't be having any kind of accident!" Andrew replies.

Andrew pauses, then looks down at the waiting pullup. He couldn't believe he was actually going to put that on. Taking a big sigh, he walked over, leaned on his boss and pull one foot in, then the other. Almost falling down in the process. The padding felt a little odd, but a little nice. Although he couldn't believe how well these fit.

[elfowl]

I smile and nod.  "Great, then you'll be right back out of these, and back into your own clothes in no time."

I wait until he puts both feet through the leg holes in the pullup.  I pull it up to his waist with a little "Upsidaisy!"  I then pull out another pullup, and hold it open for Andrew again.  "Step into this one too Sweetheart.  After he does, I reach over and pick up the blue dress.  "Alright now.  Arms up!"  I wait for Andrew to put his arms up, and slide the dress down over his head,  I slide his arms through the sleeves.  "There we go."  I coo as I smooth out the skirt.  "That looks really good on you Sweetheart."  I tell Andrew.  Looking him over, the skirt only comes a little bit down past the pullup, but it's hard to tell from the wearer's perspective since the skirt poofs out so far.  When he sits down, or moves quickly, the skirt will show flashes of the pullup.

[Daddydrew]

Andrew feels himself pulled forward a little at the "Upsidaisy", leaning more into his boss. Getting very close to her face, he blushes a little. Andrew then goes to step into the second pullup, which is slightly harder due to the pullup he already has on. Seeing the blue dress come towards him, he is hesitant to raise his arms. "Do I really need to wear a dress?" He thought to himself. He looked down at the pullups he was wearing and he figured he was already in this deep, he then raised his arms for the dress. After she was done fixing the dress, Andrew blushed at the comment replying, "I do? Hehe thank you." Andrew was nervous to move, he kept trying to pull the skirt down as much as he could, but to no avail. He felt it ride up so much, he didn't want to move. "The dress is a little short don't you think? One wrong breeze and i'm on display for the whole world."

[elfowl]

I feel happy as Andrew takes the compliment well.  "You very definitely do Sweetheart.  You're so cute I could eat you up!"  I smile apologetically as Andrew asks if the dress is too short.  "It probably is a little short, you're a little bit taller than my Nice, but I'm afraid it's the same length as the other dresses, and I don't have anything else for you to wear.  She usually wears it with some tights to cover up her legs and feet.  Would you like me to grab a pair of those for you?"

[Daddydrew]

Playing with the dress a little he looked up and said," Tights? No I don't think I need tights. I mean, it's just a you and I." Andrew admittedly was fond of the idea of tights, but he thought it would be to much. The thickness of the pullups against his privates felt really good. Even though he just had a release in the tub he started to get a little hard.

[elfowl]

I can't help but smile, seeing Andrew play with the dress.  When he declines the tights, I shrug.  "Up to you, I certainly don't mind you flashing your little princess at me for the rest of the night.  Now, if you're up for it, I want to set up a contract with you, one that will promise you the raise, as long as you hold up your end of the bargain.  This will be more to protect you, and make me keep my promise legally than anything else.  It will also formalize the agreement.  Sound good?"

[Daddydrew]

Andrew smiles and lifts the dress a bit to show off his pullups, then giggles.

He then became more serious at what his boss was saying. Even though he was in a dress and pullups, he was focused on the contract. "Yes I am ready for the contract. I am willing to do whatever it takes to not only help promote myself, but help you along the way. Sounds great!"

[elfowl]

I giggle as Andrew flashes me,  and wave at his underwear.  "Hello there Princesses.  It's lovely to see you."

I'm very glad that Andrew is onboard for and seemingly excited about the contract.  "Alright sweetheart, you relax for a bit, I'll get everything sorted out, and get you to sign.  Sound good?"  I get confirmation from him, then head down to my office.

I write out a contract that includes a few key details; changing his title from secretary to full time personal assistant, changing his hours to 24/7 with a large number of breaks, Giving me full power to dictate his tasks, any disciplinary actions, and his uniform, as well as discreetly having me both adopt him, and be granted full power of attorney and legal guardianship, it also ensures that Andrew's salary is quadruples, promising that I will cover the difference, even if the company won't agree to the raise.  There is also a clause that gives a penalty of five times the remaining value of the contract for whichever party breaks contract first, with the contract lasting 20 years.

I print out a copy of the contract, and take it and a pen on a hunt for Andrew.

[Daddydrew]

Andrew nods and says,  "That sounds good...mommy."

As his boss leaves Andrew sits on the bed in the room. Looking down, the dress rides up and the pullups clearly are on full display. He then started to think about the contract that his boss was going to present him. Even though so much had happen tonight, he was focused on his pay increase. While also making sure he could be a pillar of support for his boss.

After a few minutes of boredom, Andrew saw a mirror next to the bed. He stood up and walked in front of it to get a clear view of how he looked. He was a little in shock of what he was wearing, but he somewhat liked it. Even though he woke up this morning as a grown man working for his boss. He now looked like a little boy in a dress that had potty issues. The dress was somewhat pretty in his mind, not too mention when he lifted up the dress he got a long look at the pullups. He was in the mirror for a good few minutes looking at himself that he didn't know when his boss would come back in.

[elfowl]

After checking the Living room, and the upstairs playroom, and being unable to find Andrew, I finally go back to the room I left her in and check.  I'm surprised to find her checking herself out in the mirror.  "Hey there pretty girl."  I call out, walking into the room, and smiling at Andrew.  "Checking out how pretty you are in your dress and your padded princess panties?"  I ask, genlty pulling her to me, and planting a kiss on her forehead.

"I've got the contract right here, and a pen for you to sign with, I only need a signature on the last page."  I say, handing both over.

[Daddydrew]

Andrew almost wets himself in shock as his boss comes in the room. "What? Huh? No I...I..I just wanted to see what I look like is that. I mean, I don't usually wear this kind of stuff so I mean..I just wanted to see how I looked is all." He then feels her pulling him and landing a kiss, which feels nice because she didn't make any remarks he didn't like.

He takes the pen, then he gradually looks over the contract. Andrew seems to only be looking for the money aspects as he also see's the word support appear a few times. Shaking his head, as though he read everything, he says, "It all looks good. I'll just sign and add my initials on this last page." Andrew has signed the contract.

[elfowl]

I smile.  "There's no need to be embarrassed sweetheart.  Trust me, I of all people, understand what it's like to want to try on pretty dresses, and see how they make you look and feel.  If you would like, we can put on the tights and some shoes, really complete the outfit so you get the full effect.

I can't help but worry as Andrew looks over the contract, if he smells something fishy right now, then everything is ruined.  I nearly breath a sigh of relief as he signs.  "Alright, I'll go get this sent in, and send off copies to all of our offices.  Congratulations Andrew, you're now officially promoted to my live-in personal assistant."  I take the contract and go back to my office, making sure to send coppies to my lawyer, HR, and the legal department.  Andrew was mine now.  Completley.

[Daddydrew]

He blushes a bit, "Ma'...I mean...mommy. I'm sure you can understand, but I doubt you know what it's like to wear pullups." Andrew was tempted to say yes, he felt a little shiver at his bare legs and was contemplating it." No...I think this is fine thank you."

Andrew smiles wide as he hears he has been promoted! Never in his life would he think he would have been getting paid as much as he is now. It would take years to rise up in the company to make a salary like this."Sounds super! I am really excited to help and of course...be paid a little more." As his boss left the room he did a little victory dance. He then crawled up on the bed as he stared at the ceiling with his legs cross. Wondering what he would do with his pay increase, what to buy. Where to go."

[elfowl]

I smile.  "Those pullups are designed to feel, and look like panties, so they're less obviously for bed wetters."  Seeing him shiver, I frown.  "Okay... well if you're sure."

I make my way back into Andrew's room, I was tempted to demand that he let me fuck his ass right then and there, or to move him immediately into a crib in the little girl nursery with thumb less mittens, and a crawling harness so he has no hope of getting out.  For now though, I keep things simple, and slow.  I want him to love me, even if I know that he will in the long term.  "You about ready for bed?  We should probably take off your pretty dress when you sleep Princess, we don't want to crush that lovely poofy skirt.  We can stay up a bit later if you want, I can get you some water and we can watch a movie, or if you'd like you can have some special fun with Mommy."  I say, giving Andrew a wink.

[Daddydrew]

"Well these are definitely thicker thank panties...not that I know what panties feel like of course...it's just these are a little thick and I am wearing two of them." Andrew replies.

Andrew, not feeling too tired with the raise and promotion he got said, "Well I would be fine with staying up a little later. I don't think it's too late? I wouldn't mind a movie" He then paused, "What do you mean special fun?...mommy."

[elfowl]

"Well, once you graduate from those training panties, I'll have to have you try on some real panties, so you know."  i tease.

"We can definitely watch something then,"  I say with a smile.  When Andrew asks about special fun.  I give him a very serious look, and look deep into his eyes.  "Andrew, you are as cute as a button.  And qutie frankly, sexy as hell.  Mommy already helped you with an uncomfortable little stiffy while we were in the bathroom, and Mommy would like her turn now."

[Daddydrew]

Andrew let's out a small "grrrr" noise at the comment but pay no mind to it.

He then feel this pressure come from mommy, she is being very sweet and kind to Andrew. But now he feels like she wants more. "Well..thank you mommy for saying that...but um(gulp) what do you mean by...it's your turn?" Andrew says as he frozen with a little curiosity and a little fear.