Mistress Jessica’s Adventure: Cum Fuck Me Boots

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There was at least one bright spot to the loss of my sexy Boots.  The exhilaration that I felt knowing that another guy was wearing them and doing no telling what in them made me crazy with  excitement.  I continued to imagine all of the decadent and vile things that a grown man wearing high heeled Boots must be doing in them.  He must be masturbating incessantly; maybe he is actually fucking somebody in them; or maybe he is getting fucked in them.  I couldn’t be sure of the details exactly.

My “Come Fuck Me” Boots were made for one reason only – to provoke a sexual response which they had done quite well for me.  Now, they belonged to another Boot freak. The scenarios that played out in my mind entertained my psyche for weeks as I shopped for a replacement pair.  I did eventually buy another pair of sexy, shiny Boots that were even taller and sexier than my first pair.  But as they say, we never forget our first love. 

This new adventure opened another menu in young Jessica’s cross-dressing journey.  The complexity and the imagination of the role play scenarios that I had created in my mind served to help me through my grief at the time.  Little did I know, but this new revelation also greatly enriched my fetish experience.  My Boot Fetish had originated as a mere visual and tactile stimulus, yet looking at and touching the Boots was enough to make me cum. Without the physical touch available, my adoration began to evolve into a complex interactive love affair for Boots, cross-dressing in general, and the behaviors associated with such taboo topics.  Essentially what began as a still life photo was growing into a full fledged movie.  When I looked at my soft porn, or was lucky enough to see a woman wearing Boots in public.

I began to see more than just a sexy pair of Boots, I wanted to know what the Boots would say if they could talk….and in my mind the women who were wearing the sexy Boots were broadcasting what they intended to do in those Boots when they got home.  I began to imagine how much power these sexy leather-clad predators exerted on their prey when they seduced them in the bedroom.  Oh, I wanted that power!      

I desperately needed to expand my fetish wardrobe.  But my budget was small, my range of travel was limited by two 26 inch bicycle wheels, and I felt very self conscious buying things at the same store near my house.  So, I tried to take advantage of every opportunity that presented itself to me.  Luckily, one afternoon my mother handed me a ten dollar bill and asked me to pick up a few things at the department store.  I added the money for a pair of black fishnet stockings, and somehow lost the receipt on my way home.  with a roll of vinyl black electrical tape and a shiny black garbage bag I created Jessica’s first vinyl dress.  It matched the shiny black stiletto Boots perfectly, and the fishnets made the ensemble breathtaking!  Jessica was back and even bolder than before, and Jessica’s Boots had quite an exciting story to tell about loads and loads of cum deposited on them, followed by loving adoration and care to clean them properly.                

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I could tell he wasn’t much into the more brutal aspects of BDSM by his delicate comportment. And upon dressing him, painting his face, and crowning him her with the wig, it was made more apparent. “I will call you Fannie.” She enjoyed humiliation even though she didn’t say so, I could read it. As if the cross-dressing weren’t humiliating enough, I took it a step further and decided some pegging would be in order and there were no qualms on the sissies part. I laid her on her back and looked into her doe-eyes. I worked it in slowly as if she were a tender virgin. I could tell it was her first time. “Do you enjoy having your pussy made love to?” “yes!” sighed out Fannie the sissy. “I am going to fuck you as if you were my

She enjoyed humiliation even though she didn’t say so, I could read it. As if the cross-dressing weren’t humiliating enough, I took it a step further and decided some pegging would be in order and there were no qualms on the sissies part. I laid her on her back and looked into her doe-eyes. I worked it in slowly as if she were a tender virgin. I could tell it was her first time. “Do you enjoy having your pussy made love to?” “yes!” sighed out Fannie the sissy.

“I am going to fuck you as if you were my girlfriend,” I said as I slowly, but firmly continued to thrust into her. She was getting into a headspace, truly believing herself to be a woman in that moment. She turned on her stomach and raised her ass up beckoning my strap-on. I thrust with more vigor, losing myself in the moment and she gasped in pain but arched her back challenging herself to take more of my dick. I flipped her sideways and threw her leg over my shoulder so she could look at herself in the mirror getting fucked as her mascara ran down her cheeks. A stream of cum flowed out of her sissy dick and came out so hard it got all on her face.

As Fannie gathered herself and got back into man-mode I asked him if he learned anything about himself? He said his intention when he came to see me was to feel like a woman for 90 minutes, but he knew in the back of his mind he was a man, a very important man with an authoritative position so the fact he was just in a wig and lingerie, getting his ass made love to like a young girl was ultimately humiliating, but it gave him this jittery feeling in his stomach. He left me a very generous gift so I gave him a butt plug. “Now that you are not a fragile virgin anymore, I expect to really be able to plow into you next time. Use this for practice.”

Miss Nikki