My boss is a woman(Private w/elfowl)

[elfowl]

"Well it's simple Sweetheart.  Mommy helped you shoot out your cummies in the bathtub.  Mommy may be becoming a woman, but for right now, she still has her penis, and you excite that penis very much Honey.  Mommy wants you to make her shoot out her cummies too.  There's a lot of different ways that could be done.  Mommy would really like to stick her penis deep in your ass, but she understands if you're not ready for that Sweetheart.  Though if you are, Mommy promises to go slow, and to make sure it feels very very good for you."  I could simply make fucking me with his ass part of Andrew's duties and force him into a rediculous amount of debt if he refused and therefore broke the contract, but I don't want to pull the trigger on that too soon, there will be something much more valuable down the line, I'm sure of it.

[Daddydrew]

Taking a big gulp, a bit of reality set in as Andrew hears these words. He has never seen another penis in his life besides his own. Sure he had been curious, but nothing really came from it. An although he may have played with his ass once or twice, he didn't think he could actually take one in his ass. "Wow....uh mommy, that's a lot to take in.. I uh...ha ha...I mean..oh my...I really appreciate the time in the tub and what you did, but you are asking for a lot." Being a little frantic, Andrew said, "I....I don't want my ass to do with any of this....but with that being said...What else can I do for you." Andrew said while trying not to move.

[elfowl]

I can't help but look disappointed as Andrew tells me that he doesn't want to use his ass.  "Well sweetheart.  You can use your hands, or your mouth, but that will take a lot more work from you.  If you let me use your ass, all you'll have to do is lie there and take it, if you want to use your mouth or hands, you'll have to work much harder to get Mommy off."  I say, slowly, as If I'm explaining the concept to a small child.

[Daddydrew]

Andrew's eyes are gradually looking downwards as he is staring at his bosses crotch. Hearing what she is saying, he would like to get this over as quickly as possible. "Ma'am...I....I mean mommy, I am so unsure about this. 'Panicking a bit Andrew says, "I...I guess you can use my ass." Andrew wincing at the idea."But I am so tight mommy, please please be gentle...you'll be my first technically."

[elfowl]

I stride over, and plant a kiss on Andrew's forehead.  "I promise you I'll be very very gentle Sweetheart.  I'll make sure to stretch you out first too."  I grab the dress, and pull it up over his head and off.  "Now, Honey, do you want to do this in here on this bed, or do you need the restraints on Mommy's bed to keep you from moving around too much, and making Mommy hurt you on accident?"

[Daddydrew]

Having the dress pulled over his head, with his pullups for the world to see, Andrew is unsure on how to answer the question. "Well I...I guess you can do it here on this big." Andrew said taking a big gulp. "Just please please be gentle, this...this is my first time mommy."

[elfowl]

I nod, scooping Andrew up into my arms, then lay him down on the bed, and kiss his forehead.  "Good Girl"  I praise.  "Wait here, Mommy's going to go get some lube.  Mommy promisses to be very very gentle Sweetheart."

I walk out, retrieving the lube as fast as I can, and walking back just as quickly.  I pick Andrew up by the ankles, and pull off the pullups, then flip him onto his stomach.  I spread apart the cheeks of his bottom, and pop open the cap of the lube, then squirt a large amount onto the pucker of his anus.  I take my index finger, and start to probe his anus.  "Relax Sweetheart.  This will feel really really good if you can relax, and trust Mommy, okay Little One?"

[Daddydrew]

As Andrew laid on the bed, he was very nervous. While he was waiting for his boss to come back to take his virginity, he also couldn't help but notice that she was calling him a girl now. Andrew didn't have any attention of being called that, but did not want to correct her at a time like this.

Andrew let out a small yelp as his boss pulled his pullups off and put him on his stomach. He closed his eyes and clenched the covers on the bed. He could hear the tube being open and the lube being applied to her finger.  "I..i'll try to relax...mommy." Andrew said as the initial insertion made he moan, which he did subconsciously. He was even more embarrassed at that moan, he couldn't help it. Her finger was a little cold and felt very unusual. Andrew then taking deep breaths started to relax his anus. As the finger probing kept going, Andrew find himself getting hard again and unknowingly to him, he started to enjoy it.

[elfowl]

I keep probing slowly, gently stretching his anus, and swirling my finger around to get his ass used to having something pressing it open.  After a few minues, I gently press two fingers together, and slowly slide them into Andrew's anus.  "Theeeere we go.  Such a good girl, nice and relaxed for Mommy.  you're doing amazing Sweetheart.  How does that feel?"

[Daddydrew]

Andrew had never felt something like this before. He imagined this as being very uncomfortable, but it's far from it. His bosses fingers were so long and they felt incredible. Unknowingly, Andrew started to move and breathe to his bosses rhythm with how she was gradually expanding his anus. He also slowly starts to raise his as slightly. When she slowly slides her second finger in Andrew lets out another moan. He also cums just from her two fingers. "It....it feels ok..no..not too bad." Andrew replies in a high pitched voice. 

[elfowl]

i can't help but smile a little, as Andrew cums from anal stimulation, then describes it as simply "Not too bad."  "Sweetheart, you just came from two fingers in your ass.  I think it's a little better for you than just 'not too bad'.  Don't you agree?"  I take the lube, and pour more on my fingers and Andrew's ass, then start trying to spread my fingers apart, both to stretch Andrew's anus more, and to make a small gap for me to pour more lube into his ass.  "There we go, plenty of lube, since your boipussy doesn't make any on its own Honey."

[Daddydrew]

Andrew, twitching, couldn't lie to himself as this was the most amazing orgasm he had ever felt. He had never had that kind of stimulation before an it seemed like she was hitting his own gspot. Andrew still feeling a little sensitive after cumming so hard replied, "I've never cum like that before an so hard. I...I don't think I can take more." He then lets out a soft cry as his boss continues to finger his ass an pour more lube. "My..my what? Please don't call it that, it's not any kind of pussy. Andrew replies as his limp dick twitches and tries to gets hard. The wetness of his ass feels like nothing he has felt before.

[elfowl]

I smile.  "Oh no Sweetheart, you told Mommy she could fuck your hiney hole, and Mommy has done so much to get you ready for her.  You aren't getting out of this that easily."  When Andrew objects to the classification, I frown and double down. "Honey, it's a hole that's about to be pounded by a cock, so for right now at least, it's a pussy.  you certainly don't have another hole that could be your pussy, and you're acting and dressing like a little sissy boi, that's with an I in case you weren't sure.  So for right now, this hole,"  I say, thrusting in my fingers to emphasize my point.  "is your Little boipussy.  You understand me?"

[Daddydrew]

Andrew knew that his boss wouldn't let out so easily, but he was having trouble finding a rebuttable against her. "No, but..I mean you dressed...me like that. I.." Andrew was struggling, he was in ecstasy but also trying to resist what was happening. Everything his boss was saying was accurate, but he still tried to fight it. But as his boss really thrust her fingers in he let out pleasuring noise saying, "Ye...yes..mommy. God..(breathing heavily)..it...it..it's my little boipussy." Andrew said as he put his head face down.

[elfowl]

I smile.  "Yes Sweetheart, I have absolutely no problem saying that I dressed you like that.  I made you look like the little sissy girl you were always meant to be.  An adorable thing like you, couldn't possibly be a man."  I keep thrusting my fingers in and out, having stretched Andrew's hole enough, I add a third finger into his ass to thrust, and stretch him more.  "Let's keep going Princess, you're almost ready for mommy's cock.  You're such a good girl, so close.  So close."

[Daddydrew]

At this point Andrew was loosing his senses and his boss was pushing him to the breaking point of his control. Why did she do this to him and why did he enjoy it the way he did. Grunting he replied, "A sissy...girl? Mommy..please.." Andrew again stopped halfway through his statement as he yet again was getting hard, especially when the third finger was inserted. "Uhhhhh, ahhh." Was all he was getting out at this point. Her words were pushing him still, "Ye..yes mommy. God this feel so good...please keep calling me princess." Andrew wasn't aware of what he was saying as he only became more horny but the anal play.

[elfowl]

I keep thrusting my fingers deep into Andrew's hole, spreading them apart to stretch him out more and more.  "Of course Princess.  Your mommy will call you exactly what you are.  you're Mommy's adorable little Sissy Princess, and mommy's going to introduce you to your royal duties.  You're finally ready for Mommy's cock in your bottom."

I pull down my pants, and coat my cock in more lube, before lining my cock up with Andrew's anus, and slipping my fingers out.  "Here we go.  Bear down for Mommy like you're going poo poo, and it will go in much easier Sweetheart.  Be a good Princess for Mommy."  I start to gently push my cock against Andrew's anus, making sure to go slow, and gentle, but very firm, to get my cock inside of her, and then push in deep.

[Daddydrew]

Andrew's eye's were practically rolling in the back of his head from pleasure. His boss saying all of these words didn't help either and he couldn't control what was coming out of his mouth. "Yes mommy,  I am ready for anything you say. Please don't keep your princess waiting."

When she pulled out her fingers, Andrew slightly looked over his shoulder and his eyes went wide. Her cock was huge, he then turned away and kept his eyes down as it entered. It slightly hurt when the tip started to enter. Not as much as he thought it was, but it felt like the opposite of pooping. As the cock was going further in, Andrew let out the loudest and slowest moan yet, really gripping the bed as he did his best to stay still.

[elfowl]

"Such a good girl"  I coo.  "Lets get this all the way inside."  I push my cock all the way inside of Andrew's ass, slowly slowly, inch by inch until my hips are touching his bottom.  I hold still, letting Andrew get used to having my cock stretching out his anus.  "How does that feel sissy?"  I ask.

I wait for a full minute, before groaning, and pulling my cock back out until just the tip is still inside of Andrew's anus, and then thrusting in hard.  pushing all the way in again.  I slowly work myself into a rhythm, giving long, slow, but deep strokes, pushing in as far as I can.