My boss is a woman(Private w/elfowl)

[elfowl]

I smile and take a sip of water.  "I'm sure it will, and I can appreciate that.  I'm glad all that doesn't sound too bad."

I smile when he mentions the super yummy food.  "Well then, that sounds like an agreeable deal to me."  I say, laughing.  "I've always wanted to cook more."

I pause, making a dramatic show of going into contemplation, then speak up a little.  "There is one other thing you could do...  no, no... that's silly, never mind..."

[Daddydrew]

Andrew smiles and said, "Well it's been so long since i've had a home cooked meal. I usually order out or make ramen. I would love to try your food if it's anywhere near as good as this."

Sensing that his boss is a little nervous he says, "No no no, please tell me. I feel like I am in all the way now haha. What's that one other thing Ma'am?"

[elfowl]

I smile.  "I'll just have to try out a bunch of different things to cook.  It will be a nice little adventure for us."

I blush a little.  "Well, it's more than a bit silly, but I was thinking that perhaps.. you could... well do some of this stuff with me.. just to be supportive and such, you know.  I'm not talking about any of the hormones or the surgery or anything like that... but perhaps just like... wearing panties... learning how to tuck... learning how to put on makeup... learning how to walk in heels... perhaps even going clothes shopping?"

[Daddydrew]

Andrew almost chocked on his food when he heard this."Wait you want me to be a girl too? I don't know how I feel about that Ma'am." Andrew paused for a couple of minutes, "I don't think I would mind as much if we did those things here..clothes shopping though. I guess I could kinda help you there. Not sure if I would want to wear anything out in public though."

[elfowl]

I'm quick to clarify, "Just so that I won't be doing it alone.  And like I said, nothing permanent.  you don't have to become a girl if you don't want to.  If you do, I'd be more than willing to help you, and to pay the full costs of everything for you."  When he starts to agree to do things with me in private, I smile.  "Oh, thank you so much Sweetheart.  You have no idea what this means to me.  I'm so happy you're saying yes.  We'll take it one step at a time.  I'm not exactly ready to run out into a mall and go try on dresses right now either."

Once we're both finished, I ask.  "How about we clean up the kitchen together real quick, then we go cuddle on the couch and watch TV.  How does that sound Honey?"

 

[Daddydrew]

Andrew felt a bit of relief as he was confirmed by his boss he wouldn't be turned into a girl, to him this was just support for his boss. "Well I don't think I could ever be a girl and do what you are doing. I'm a ok with being a guy...Ma'am." Andrew could how happy this made his boss and Andrew felt good he was their for support.

"Oh, ya cleaning up sounds great. Cuddling....I uh, might feel a little uncomfortable about that. But uh...guess I can try it out?" Andrew said awkwardly as the idea of cuddling with his boss was a little weird.

[elfowl]

I can't help but notice Andrew's word choice, and I feel like prying just a little bit deeper.  I pick up my plate and glass, and carry them to the kitchen, indicating for Andrew to follow.  "You don't think you could do what I"m doing?  Why is that sweetheart?  and you're just ok with being a guy?  Not happy?  not estatic?"  I wait for him to answer as I rinse off the plates and put them in the dishwasher, then add.  "I'm just making sure I understand how you feel."

Once we're done in the kitchen I make my way to the living room, and lie down on the couch, scooting back, and then patting the space in front of me.  "Come here Sweetheart, let's cuddle.  Thank you so much for doing this.  I've always wanted more physical contact with someone I could trust.  You're really doing me a huge favor, and I'm feeling so much better already.

[Daddydrew]

Andrew sees the motion to follow along, so he walk behind my boss with my plate and glass. Placing them on the counter, he is a little caught off guard by the questions. "Well I uh...I mean..like...I've never been asked that before. I mean being a guy is good, I don't know anything else. I would say I am happy about it...um. But what your doing takes a lot of commitment too, also I know it is something you have probably wanted for so long right?"

After thinking more, the dishes were done. Andrew then follows his boss into the other room and see her lay on the couch with open arms. He pauses for a moment, but she reassures that this is making her feel a lot better. Andrew then sits and lays down on the space in her front of her and says, "Well I am glad this is helping you Ma'am, really I am." To say Andrew is the small spoon would be an understatement.

[elfowl]

I nod.  "It is something I've though about for a long time, but it certainly wasn't something that I was certain about until recently.  It does take a very large amount of commitment, and you have to accept that many things can go quite wrong.  There are a lot of potential embarrassing, uncomfortable, and even life threatening things that can come from transitioning, so it's very easy to think that just staying as a man is easier, and therefore better for you.  Really, all that I was sure of is that I was unhappy.  It wasn't until very recently that I decided that something needed to change.  It's a shame really, it was something that I had considered when I was much younger, and still had the good looks, and a young healthy body that would have recovered much more quickly, I didn't have the money to transition.

I happily wrap an arm around Andrew as I spoon him, happily pulling him to my chest.  I hand him the remote.  "Put on whatever you want to watch."  I tell him, simply enjoying holding him close to me.  I lay there with him for a few minutes, and begin to wonder when the diuretic I put in his drink will kick in.  I know that with the powerful diuretic is going to hit hard when it does, and I'l be surprised if he can hold his bladder more than a minute after he first feels the smallest urge to go.

[Daddydrew]

Andrew takes in everything his boss is saying and puts it into a bigger perspective. People today are a little more excepting about this compare to when his boss might have been younger. Would probably be a little easier with Andrew, but he shook that idea off. "Well I guess better late than never I suppose!"

Andrew feel very uneasy about cuddling with his boss, but he can hear her heartbeat which surprising calms him a bit. "Oh thanks." Andrew says as he sits up a bit, after scrolling through a few channel Andrew stops. He has a slight urge to pee, which he feels that he can hold. Then, what felt like a ticking time bomb, went from I think I need to pee to suddenly i'm a about to pee now. He does his best to get out of his bosses arms by saying, "Please I need to..." Andrew fell onto the carpet as right then and there, he started to piss himself. He couldn't stop, he just was frozen as he just kept peeing."

[elfowl]

I'm only half paying attention as Andrew flips through the channels.  I feel him stop, and then quickly start to look worried.  "What's wrong?"  I try to ask, but before I can even get the question out, Andrew is pulling at my arm, frantically trying to get up saying "Please I need to..."  before he face plants into the carpet.

"Sweetheart, are you okay?"  I ask, feeling genuinely concerned, then i hear the unmistakable hiss of Andrew's bladder releasing, I watch, unable to help but get aroused as Andrew's work slacks slowly start to get a small wet patch, that then quickly spreads all across his crotch, then down his thighs to his knees, down his front, and dripping straight down from his crotch onto the carpet, as gravity pulls at the pee making it run down from Andrew's raised butt.  In an instant, I'm right beside him, wrapping my arms around his torso and trying to comfort him.  "Oh my goodness Honey, are you alright?  What on earth happened?"

[Daddydrew]

Andrew is beyond embarrassed, he actually can't believe he lost control like that and so fast. One second he was fine, the next he uncontrollably pissed himself. He didn't want to move, he wanted this all to be a dream and just not acknowledge his situation. He could feel his boss trying to comfort him, "I...i'm ok...but I...I god...I am so sorry, I don't know what happen! I..I.." Andrew said as he started to get a little teary eye. "Please don't look at him, I didn't mean to do this, I just couldn't control it."

[elfowl]

I gently stroke Andrew's back, tyring to help him calm down, and pull him into a tight hug.  "Shhhhh, shhh, It's okay Sweetheart.  I know you didn't do it on purpose.  Of course you didn't do this on purpose.  I understand.  I'm not mad at you.  It's okay.  You're okay.  I've got you.  I'll take care of this, just calm down and we'll make everything alright."  I pull him onto my lap, sitting on the floor, and simply rock him side to side, as I hold him to my chest.

Once it seems like Andrew has calmed down, I pull him away and look him in the eyes.  "How would you like a nice bath, and some fresh clothes?  How does that sound?"

[Daddydrew]

Andrew just wanted to curl up into a ball and make this all go away.When his boss pulled him on their lap and started to sway him, Andrew put his head in her chest as he started to cry a little more. The mess he was in, how embarrass Andrew felt. After a few more minutes, Andrew sniffled and did his best to collect himself.

Looking into his bosses eyes, he wanted to cry again but knew that she was only trying to help. "I...I think that might be best. But I can clean myself and what do you have for clothes for me? Someone so tall, wouldn't have something for me." Andrew said as he looked away.

[elfowl]

I snuggle Andrew softly, gently rocking him as he calms down, cradling his head agasint my chest.

I nod when he points out that my clothes would't fit him.  "You're right Sweetheart, but... well... I don't think there's a good way o putting thsi delicately, but you're the same size as my little niece, and I think I have some clothes that her parents left here they last time they came to visit.  Let's not worry about that quite yet though Honey, let's get you into a bath, okay?  I stand up, still Holding onto Andrew, and carry him upstairs, down a short hallway, and into an enormous bathroom.  I turn on the tub, and plug it up with Andrew still in my arms, then sit down on the toilet lid, and cradle him in my lap as the tub fills up.

[Daddydrew]

Andrew was still in shock as to what happen, he didn't really hear the niece comment as he replied, "Oh uh, I guess that works." He didn't think about what he said but just wanted to be out of his piss soaked clothes and didn't want to smell like pee. Andrew looked at the bathroom as it was huge, it was almost the size of his apartment. As Andrew is being cradled by his boss, he was shivering a little bit, he wanted to put this night to an end. Not looking at his boss, "How...how much longer for the water?"

[elfowl]

I look at the mostlly full tub, and note.  "Just a minute or so.  Let's go ahead and get you out of these wet clothes, okay Sweetheart?"  Without waiting for an answer, I pull off his shirt, and undo his pants, standing him up, and pulling his pants down along with his underwear.  "Step out for me Honey."  I tell him.  I look at the water in the tub, and it seems mostly full.  "Alright, you can get in while it fills up the rest of the way.  Feel the water first and tell me if it's too hot or too cold"  I command gently.

[Daddydrew]

Andrew was caught a little off guard as his boss started to undress him. He was still in shock as his arms and hands were moving the way he wanted them too. He looked up at his boss when asked about the underwear, he didn't want to take them off. Not many people had seen his privates, they were small to say otherwise. After a minute he did as he was told and stepped out of his underwear, he tried to turn away but was of no use.

Andrew, butt naked, tested the water and replied,"It's a little hot but I think I can manage." Andrew then steps into the tub, he pulls his legs to his chest and waits for the water to fill.

[elfowl]

While I'm getting Andrew out of his wet clothes, now that he's simply standing there, I take in his naked form.  He's even cuter with his clothes off, and his tiny little genitals are absolutely adorable.  He's just too perfect for someone to take him and make him their little baby girl.

When Andrew says the water is a little hot, I move to put in a bit of cold water to cool it down, but once he says he thinks he can manage, I simply let him get in.  Once the water is high enough, I grab a washcloth, and rub some soap on it, then start gently, but thoroughly washing Andrew.

[Daddydrew]

Andrew was still very tense and was able to relax a bit when the water was full. The touch of the washcloth felt nice, it as soft and starting to make Andrew smell better. The whole time Andrew made no eye contact with his boss. He was utterly embarrassed that he was being washed like a child when he is an adult. "I...I, Ma'am..after this I could get an Uber or something and go home if you want. I completely understand if you wouldn't want me to stay, I doubt you enjoy cleaning and the smell."

[elfowl]

I notice Andrew making eye contact with me, and I smile at him gently, maintaining eye contact, as I start washing his privates.  "Nonsense.  I'm not going to send you out of my home just because of an accident.  Stay here tonight.  Please.  You're helping me, let me help you.  I'm more than happy cleaning you, and I don't mind the smell all that much.  Besides, we're getting rid of the smell now.  Aren't we?"

[Daddydrew]

Andrew still feeling a little down, nodded and said , "We are ya, I'm starting to smell better too....uh thank you." Andrew not noticing his bosses hand slide down between his legs, let out a slight moan. Embarrassed because he started to get hard, he hadn't been touched in years and his dick would only get up a few inches. He started to cough to try and make it less embarrassing for him.

[elfowl]

I feel Andrew start to get hard, and hear him moan, and I can't help but smile.  "Do you like that Sweetheart?  It's okay if you do.  If you want me to I can make you feel really good down there Honey.  Just let me know, and I'd be happy to do that for you."  I smile as I stare into his eyes knowingly.

[Daddydrew]

"No..I..I don't.." Andrew said as he stares into his bosses eyes. He felt so vulnerable, but he couldn't deny that it felt good. "I mean..(biting lip), it does feel good. Please...please keep going Ma'am." Andrew was breathing a little heavy as he started to relax a little more.

[elfowl]

I frown as Andrew tells me that he doesn't like it, but that quickly turns to a smile, as he admits how he really feels, and pleads with me to keep going.  "Okay sweetheart.  Just relax then, Mommy is going to make you feel all good.  I grasp his small rod, and begin to firmly rub it up and down, making sure to focus on the underside of his tiny cock, and the sensitive head now peeking out of his foreskin.  I reach into the water with my other hand, and gently rub the insides of his thighs.  "Go ahead and make cummies for Mommy sweetheart.  Let it all out. Sweet thing.  Oh you're so precious.  Let Mommy make you feel good.  Tell Mommy how it feels, go ahead."