Maddie had the biggest grin on her face as I wait on all fours on the bed. She tugs on my pants and makes sure they are pulled tightly into my crotch then winds up and slaps her open hand into my crotch, smearing and grinding the pie she had dumped into my pants just minuets ago. Squeezing my pie covered bulge, hope your ready for this? Mistress please that toy of yours is quite big. She gets up close to my ear, it sure is, big and pink! she giggles. Can't wait to see you on it. I better add some more lube. she giggles. Maddie grabs some lube and globs it on to my pink nightmare and strokes her rubber gloved hand up and down the latex dildo, smiling and stroking it, Oh yeah, such a big pink cock, she laughs out loud, I bet my sissy can't wait to have this baby inside her. With that she slaps her hand into my ass and smears and rubs the second pie she slipped into my pants earlier. Pie slop now falling down the front and back of my legs to me knees. She spreads my feet and slides her toy into place between my legs. The tip of the toy only inches from the hole she made in my pants, she slipped her two fingers into my ass for good measure and whispered to me. Its time my Sissy Sock pie bitch, I want you to slowly lower your ass down I will guide this lovely pink cock into place. This may hurt a bit so I will take it slow so my sissy can enjoy every inch of her demise. Lets do this, she places one hand on my shoulder and I begin to lower myself, I feel the cold tip pressing against my asshole. I am feeling so vulnerable helpless and sissified right now, so humiliated and hard as hell at the same time. Could this really be happening, My thought to be innocent girl has me dressed in a sock suit, my cock and balls tied up tight, she has my head covered in her smelly sock, she has my lips slathered in hot pink lipstick and gifted me with a long flowing black wig, a soft wool hat. Now I am about to have my ass violated and who knows what to follow. The really messed up thing is I am so stiff and turned on right now, could she be really turning me into her Sissy? This is insane, and she knows it!

I feel the tip just pushing its way in and her hand pulling down on my shoulder to help everything along. Up and down nice and slow Sissy girl, pie cream oozing out and deeper inside me as it goes deeper with each push. Maddie is basically fucking me against my will slowly and seductively. Oh yeah Sissy Pie, that's a good girl, take that cock up your ass. she laughs.This was quite uncomfortable and painful, Mistress please I can't go any more. Oh you silly Girl just be patient. This was so wrong on so many levels, how could I let her do this. Just stop there, try to sit down and keep the pressure on until your muscles relax. Maddie took her phone and set in in place zoomed onto my face and began recording. Now sissy do as I say, yes mistress.
I wish I could see your face right now. Your cock is so swollen and hard. You must be loving all this attention. Now move your sissy tight ass up and down on that cock, yess just like that, relax and let that cock find its way in. Keep at it. Maddie removes one yellow sock and slips a smaller dildo I was forced to suck earlier into the sock, but not before dipping it into a coconut cream pie and covering it real good. She ties a knot to keep the sock tight. So sweetheart you know real Sissies like all their holes filled. Oh please no Mistress not that again. Please,,,she slips the sock cock into my lips once again, now follow my lead Sissy, in and out, just like this she begins fucking my mouth with her pie covered sock cock, her other hand pushing down on the top of my head. Up and down, in and out oh yeah now your getting it. I can't believe this is happening. Mpppfffff. oh my keep going Sissy your ass needs to sitting in that pie before this is over. So humiliating, So naughty. I finally pass a point of pain and find myself relaxing and embracing my sissification for the night. My ass slips down onto the pink toy and my cheeks kiss the pie cream. Maddie continues fucking my mouth with her cock sock, This is sensory overload, I am now being fucked by this once innocent shy woman turned Mistress.

Oh yeah Sissy you are almost there, ohhhh mmppphhffff. my cheeks barely pushed into the pie as my ass came to rest on my calves, finally, I say to myself, feeling quite filled. Maddie continues to fuck my mouth with the sock cock then unties the knot stuffing the sock in with the dildo gagging me silent with her yellow sock. Oh My sweet little Sissy you have come this far don't stop now. She grabs my socked feet and pulls them apart spreading my legs and allowing my ass to smoosh right into the pie with a splat Pie squishing out on all sides and the pink cock to slips all the way up inside me. Oh that's a good Sissy take that whole cock up your ass. Holy shit oh my this was a total surprise I was not prepared for I just froze in place from the feeling of this going too far, afraid to move and inch I was in awe of what she has done to me. She stands up both hands on my shoulders. How's that feel darling? I said nothing still frozen with the overload of sensation. Now that you are completely at my mercy, lets tie those hands again, she tied my wrists together in front of me and removed my wool hat. She slipped her white slouch socks back on dipped her foot into the pie and began pushing the yellow sock deeper into my mouth with her foot. Oh suck a humiliated Sissy Sock Pie girl you are, pitiful mess. Maddie picked up a coconut cream pie and said Sissy needs a a pie and she plopped it onto my head and knocked of the tin off, a few gentle twists and grinds then she replaced my hat and pulled it down tight, Pie oozes out the sides and she just smiles. Then 2 banana cream pies are slammed to each side of my head and smeared in thoroughly, as I began to shake and quiver Maddie continued to smear and press the pies to the sides of my head, Cum for me Sissy she shouted. I couldn't hold back and blew my load yet again.

Just as I stopped she smashed a second coconut cream pie right into my face smeared, twisted and smushed it in good and held it there until I came again. I was so overwhelmed with pleasure and even after two orgasms I was still rock hard. I just sat there in my Sissy sock suit, hair matted totally humiliated covered in pie, gagged with a sweat sock with a pink dildo up my ass.

Maddie continued her quest of total humiliation by pushing me onto my back and stepping all over me with her pie covered socks, she finished me off by fucking my mouth with her pie covered socked foot bringing me to orgasm one last time.
She went off to shower up and I just fell asleep in my totally humiliated state, exhausted and covered in pie.