Sissy Slave Boyfriend


I told you that although you had a fairly talented tongue, you had only been able to make me cum once and it wasn’t exactly satisfying.


The More Aroused We Both Got


You quickly went from looking pleased with yourself to disheartened.  And you said that you were so disappointed in yourself and that you had really wanted to please me. Despite this, I noticed your little dick was quite hard and dripping pre-cum.  Your shame at being unable to satisfy me sexually was very exciting to you. And the more I shamed my sissy slave boyfriend for it, the more aroused we both got.  


So, I told you how I really felt about your self-described ‘expert oral skills’: “I know you believe that being good at bringing women to orgasm quickly and efficiently with your tongue compensates for your sadly average penis.  But it doesn’t.  I realize that you have probably been telling yourself this for a long time and it has helped your sexual self-esteem.”


And I went on to explain, “first, you’re definitely good at it for a sissy slave boyfriend but not the best I’ve ever experienced.  The best was my ex-boyfriend who could make me cum over and over that way and then fuck me with his thick, ten-inch cock until I was completely satisfied.”  My point was that guys with porn star-like cocks can eat pussy too.  And sometimes even better than you can.  And if that’s all you’ve got going for you, then you really have almost nothing to offer a woman.  


Sissy Slave Boyfriend – Convincing A Mistress


Well, almost nothing to offer except for how exciting it was turning out to be to humiliate and dominate a sissy slave boyfriend.  And there was the fact that you were persistent and that you said you had always found me enchanting.  My ego liked those things.  But I was still far from being convinced.  I thought we could be great friends but wasn’t sure there was much point in pursuing anything more because of your “shortcomings.”  But, you still seemed determined to convince me. 


For some reason, I had absently been lightly playing with your stubby little dick with a few fingers as we talked.  I barely noticed what I was doing until you started desperately pushing it into my hand, trying to get me to stroke it faster and harder. It was obvious that you were about to cum so I took my hand away, leaving you looking like a very silly sissy slave boyfriend ineffectively humping the air. 


You begged me to touch you again and said that you would do anything I asked. I told you that I did not want you to cum and asked if you still wanted me to continue. “Yes!” you replied in a very grateful way.  So I started edging you with my fingertips again and again – always stopping short of an orgasm.  And you moaned in pleasure and frustration every time – in fact, you seemed to enjoy having me control your pleasure.  That really appealed to me.  And I found that the thought of being a chastity mistress was kind of hot – I’m not gonna lie. 


Definitely Not Boyfriend Material 


I started to love having that kind of power over you.  And really, I also just liked spending time with you.  Sissy slave boyfriend or not, you were fun to be around and you treated me like a Princess.   Then, as if you could read my thoughts, you asked “so, where is this guy with the monster cock?  Why aren’t you married to him?”  And I somewhat sheepishly explained that although the sex was incredible, he wasn’t exactly a great guy and was definitely not “boyfriend material” 


You could have laughed at me here for framing him as “better” than a sissy slave boyfriend but you didn’t.  You just recalled “oh, yeah – I remember you complaining about that guy at the office with your friends.  He really does sound like an asshole and I’m glad that you never plan to see him again.”  Well, we both know now that the last part of that wasn’t and hasn’t been quite true but it was still a very kind thing for you to say. 


And then you proposed that “maybe this time you should try a sissy slave boyfriend with an average dick who adores you, rather than an alpha boyfriend who isn’t very nice to you.” 


What Did You Think?


Well, my sexy perverts… Did you like part five?  Were you expecting Sissy Slave Boyfriend to propose such a thing?  And how do you think that our Mistress will react?  But more importantly, what did our Mistress mean by “the last part of that wasn’t and hasn’t been quite true?”  Let me know what you think in the comments below!


Totally Lost?  Not sure what’s going on here? Don’t worry!  Head over to Part One:  A Sissy Slave Boss and read from the beginning.


Fun femdom fantasies Roxie (800) 601-6975


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