As promised Maddie was all ready for Halloween, she had purchased this Baby Doll Sissy outfit secretly then surprised me with it a month or so ago. Maddie had never ever shown any interest in my fetishes. Then out of the blue one day she gets this in the mail tells me its for Halloween and she thought it would be funny to have me wear it and try it on. We both had a good laugh, but mostly she did, as she made me model it for her. I was game to do it in hopes she may come around with my crazy fetishes. To my amazement she again out of the blue had set up this whole ordeal just a week after I tried this on, Turns out she was taking detailed notes on our conversations, so one day I arrived home to this whole set up on my bed. Needless to say she went all out and humiliated the shit out of me and used all of the crazy things I had talked about or showed her over the time we have been together. It turned out to be one of the best nights in quite a long time. This happened a week prior to Halloween. I think she got the taste for humiliating me and liked it. So when the time got close she had come up with some more Humiliation for me, but this time in public. She had promised me she would wear an outfit to compliment mine. She wore all white, a skimpy maids dress with white long gloves, thigh high heeled boots, choker and a chefs hat. Maddie looked amazing like a Slutty Mistress Chef.

Once she was all dressed she set out my outfit and she added some pink thigh socks and gave me her pink emu boots to wear, before she got me into my new outfit she had one more task. I noticed how much my Sissy enjoyed having something inside her so I got you this, Maddie held up a decent size butt plug and attached to the base were three small rubber rings, She promptly lubed it it and began the chore of pushing it into my ass, after a few min she managed to begin my humiliation, now that the plug was in place she moved around to my front side and of course I was already excited, she stroked me once or twice then pulled the attached rigs forward, one went over my cock and was slipped down to the base, then the other two remaining rings were for each of my balls, one pulled tightly around each nut separating and keeping a squeeze on all three separately, this whole setup felt amazing and kept me stiff and fully aroused. Maddie slipped the dress over my arms and my face into the giant pink heart shaped bonnet. Now as the outfit wasn't humiliating enough she put the wig from last week on me once again, so so precious you are my Sissy boy. Oh my god this outfit you bought is so over the top Sis, I can't believe you are making him do this. Laughed Erin. She had no clue what Maddie had just fitted me with. Maddie and her sister then put me in full makeup.Oh sis look at your little Sissy isn't she just darling. they both laughed This turned me on so much for some reason, to be treated like this.

Unbelievably this was even more humiliating than the other night, as now I was really dressed like a full blown sissy girl, and the embarrassment of Erin being there made it even worse. Had Maddie and her sister really planned to take me out like this? Or were they just teasing me? Her sister was along to take photos and help out. My hands were covered in some type of mitten like hand restraints and tied in front of me.The heart shaped pink head piece really upped the sissy factor. Maddie's pink emu boots and socks finished the whole look. They escorted me to the van, the heart bonnet was so big it hit the roof inside the van. I had to keep my face down in humiliation for the whole ride. We were headed to the downtown area. I was really nervous on the ride over and was having second thoughts about going out in public like this. This area was known for late night events, bars and clubs. Once at our destination I stepped one foot out of the van and got a pit in my stomach and became very nervous. Maddie snapped a pink collar and a leash around my neck. My first thought was, I hope I don't run into any one we know. Her sister unloads a wagon and begins stacking it full of pie boxes, I was in total awe that she was really going thru with this and she has stepped up her game by adding the pie factor, laughing She says Maddie what made you think of pies? and damn Sis don't you think forcing him in to this outfit is quite enough? Maddie answered, it just sounded like it may be fun seeing our little sissy getting pies in her face. She winks at me. Erin had no idea about what went down last week as well as what my raging fetishes were.

Erin had the wagon loaded up with Marie Calander banana cream pies, we began to walk toward Main st.and already I was getting much unwanted attention. Maddie was loving every min of this and letting women take pics with me and asking them if they wanted to pie me. To my surprise none of the women were interested in creaming me with a pie. Two hot girls dressed as maids even kissed both my cheeks at once for a photo leaving imprints from there heavy red lipstick. One really drunk girl was obsessed with me and kept saying how she wished she had her very own sissy and asked Maddie if she could take me home. Maddie was all smiles all night just watching me squirm. The drunk girl wouldn't leave us alone before we knew it she was pulling a dildo out of her purse and holding it up while saying, are you a real sissy boy? you must like to suck cock then, right? Maddie chimes in, Oh girl you have no idea how much she loves to have things in her mouth. Laughs Maddie and Erin. I can't believe she said that shit. WTF? You don't say, slurs the drunk hot blonde. She pushes the tip to my lips, well lets see the sissy suck some cock. she giggles. No way! Maddie steps behind me and places her hand on the back of my bonnet, be a good sissy and show this nice lady how good you are at sucking cock. She says laughing out loud. What the Hell Maddie I say with an angry tone. Oh my Sissy bitch you will not raise your voice to me. Now show us ladies some respect and do as we ask.Or ELSE! I like her said the drunk woman. Yes Mistress, I bow my head Maddie opens up a pie box and holds the pie in her hand offering it to the woman, oh my what do we have here, the girl grabs my face, such nice pink lips, she plunges her dildo into the pie and smears cream all over my lips, she re dips the dildo and with one hand on the back of my bonnet she shoves the tip into my mouth. Erin is snapping photos of this whole ordeal with the look of horror on her face. The woman wastes no time fucking my mouth with the cream covered toy. Maddie just makes it worse by egging her on. "oh yeah sissy suck that cock you know you love it" laughing " take it all in your mouth you slut" "that's a good Sissy girl" I can believe this is happening on a public street corner. This strange woman is now fucking my mouth with her own pie covered dildo, right here for all to see. This is so humiliating and yet such a rush. Another woman walks over and says, Brit what the hell are you doing? She pulls her away from me and says I am so sorry she obviously has had to much to drink. Let's go.

The both walk away and Maddie just smiling with a pie in hand. Oh that went well, she laughs. How did you like that Sissy bitch, you just love having your ass and mouth stuffed, don't you Sissy pie? Erin chimes in Maddie what has got into you? I have never seen this side of you. Maddie hands Erin the pie, she likes this Erin, trust me on this. Really, are you for real? but why? Oh I will tell you later, just feel her crotch. OH MY says Erin I guess you know your guy best Maddie. How strange. Go ahead Sissy get on your knees and tell Miss Erin what you want. I kneel down in front or Erin, Mistress Erin please smash that pie in my face, I really want you to, I deserve to be humiliated. Erin just laughs, this is some kind of joke right? Maddie? No joke Erin he love this shit. Well ok if you says so, Erin looks me in the eye, you really want me to hit you with this pie? Yes Mistress, please let me have it. I have never hit someone with a pie before. Are you sure. Fuck Erin just do it smash it in his face and smear it around good.said Maddie. Erin was nervous and unsure. Beg for it bitch, says Maddie. Please smash that pie in my face Mistress, I want you do do it! Let me have it I am begging you. Erin finally gets up the courage and smashes the pie in my face, take that you Sissy, she twists the pie back and forth smearing it like a pro. Oh this is fun Maddie. Says Erin.

The pie tin slowly slides off my face and they help me back up onto my feet. Nice job girl you got her good. Maddie wipes most of the pie off with a towel and we continue walking down Main Street. There are many comments made about me and my outfit, but honestly I had already been humiliated beyond my widest dream. After hours of waling around and still no takers on the pies we turned down this alley way. There was a large plastic garbage can near a door, Maddie decided to push me back into it and I toppled over into the can ass first. Maddie pushed and stuffed me down into the bin, my feet were dangling over the edge. Mistress what are you doing? She laughs, putting you where you belong in the trash. with my hands tied in front there was no way for me to get out without help. She leaves a note, please pie the trashy Sissy bitch. She left me there with a wagon full of pies and the note, we will be back soon time for a drink, now don't go anywhere we shall return soon. Here I was now helpless as hell, stuck in this can hard as a rock dressed like this with my ass plugged and cock and balls bound up. Two dudes come around the corner and take a piss in the alley and didn't even notice me. Then after a while I hear female voices, the two ladies from earlier were walking thru. Oh my god look who it is, said the girl, I wasn't kidding, that woman told me she really likes to be humiliated. I see that, said the second woman. Come on look at the note! Well, what the hell, go for it! I will stand watch. The Hot blonde opens up every box and sets them on the ground, about 14 pies.

The woman began smashing the pies all over me covering me, smearing twisting and smushing each pie, she even slipped off my boots and dumped half a pie in each then smushed them back on to my feet. The two laughing hysterically the whole time. All but one pie had me covered head to toe. She had left my face for last and said to me if you are here when we pass back by I am taking you home with me, you can be my full time sissy. With that she smashed the last pie into my face and it exploded onto the heart bonnet and the crust just stayed there, she pulled out her dildo once again and pushed it into my mouth. There you go Sissy Pie Girl, my gift to you! Well you have been properly trashed and humiliated. have a good night.

The two ladies walked away, I couldn't move, clear my face, wipe anything off. I was stuck like this, now worried who may find me. Thankfully Maddie and Erin soon arrived to find me in this state. Oh my god Maddie look what happened. I love it! said Maddie, and I think I know who it was, as she slips the dildo out of my mouth, she then begins fucking my mouth with it and says, did my little sissy enjoy her trashing? mmppffff. Yes Mistress. My you are such a mess, you have been a naughty little Sissy haven't you. Oh no, look what you did to my pink emu boots, they are ruined. You own them now. They pulled me out of the bin and walked me back to the van. Walking in pie filled boots was not only a strange feeling but a challenge.

So Sweetheart, was this your best Halloween ever you little freak?

Yes Mistress, thank you