Becoming a Sissy Maid & Slut Vol. 05

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Becoming a Sissy Maid & Slut, Vol.5, Chapter 11.
3k words
4.48
32.9k
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Part 5 of the 14 part series

Updated 06/08/2023
Created 07/13/2016
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Prefix: A continuation of my sissy maid and slut journey. I hope you all do enjoy my unfolding story here. I am writing further chapters with hopes to give you all a semblance of some of my sissy ideas and thoughts so that these may excite you as the reader. I will try hard to keep each chapter on an exciting flow of what I feel may be life of a full time sissy maid and slut to a true dominant, yes in my case a Master but always hoping it turns readers on.

Please try to keep with me as I'm outlining numerous other chapters to follow, with some erotic plots, twists and turns... Happy curtsies.

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Chapter Eleven: Being Gang Raped is a Sissy Slut's Privilege.

As I arrive back home, I know I have to take care of a few chores before I get Master's dinner on the go. I also need to keep watch on the time as when Master comes home from his work I must dutifully and daintily greet him at the front door with a curtsey and a welcome home how was your day?

I am always kept busy as a sissy maid and rightfully so. So I get on with a few chores and then with Master's dinner. But once he arrives I as noted greet him. Soon it will be time for me to serve his dinner. Master notes that Sir Rick will be by for dinner as well. I curtsey and get the table ready. I also greet Rick with a curtsey once he arrives.

Soon seated I serve them their dinner and then as typical once Master gives me permission have myself a bowl of gruel. Master though is kind enough to allow me to pour myself a fresh cup of hot coffee, to which I show immense gratitude for such kindness.

As I know already, tonight is being set up as a massive gang rape of me. Master tells me again that the motel room I made my BBC porno movie last night will be the room for the arranged gang bang. I acknowledge this and my nervous, excitement to what will be for me a most memorable night of massive, bondage, gang rape. He and Rick are very excited for this as well.

As dinner finishes, Master and Rick relax in the living room as I then serve dessert and coffee. I then wash all the dishes. Once finished I re-enter the living room and curtsey before Master telling him I have finished washing the dishes. It's now about 6:00pm as he then sends me to my bedroom to then dress as slutty as I can see fit for my gang rape session. I curtsey and say, "Yes, Master, I will Master, thank you Master."

In my room I remove my maids dress, petticoat, slip, pink pantyhose and my pink heels, leaving my white bra and panty on. Carefully put these beautiful, feminine clothes and shoes away. I then touch up my makeup. Now I go through my pantyhose drawer and decide on which pantyhose for me to put on. I decide to go with a pair of sexy, black, fishnet pantyhose.

Carefully, next pulling them up my smooth legs and over my sissy hips. Oh I'm looking quite slutty. I then pick out a short dress long sleeved, with a white satin upper section that then cuts in at the waist line a very short black raw silk designed skirt section. The skirt is A-lined very short but flares out giving gentle fullness to the lower part of this sexy, lil, slutty dress. My black, fishnet, pantyhose clad legs sexily stand out long from this dress's short hem line. Next, I pull out a sexy pair of medium blue, suede 5 inch spiked heeled pumps. A sexy blue contrast to the black and white colour scheme I am wearing. I then grab a small, long strapped, blue suede purse to put my I.D., some cosmetics, perfume and a bit of cash inside.

Finally I have a sexy, black, suede, bolero jacket with fringe down the sleeves, Mmmm so cute 'n sexy. A final standing check before a my full length mirror and I look to my eyes so deliciously, sexy and slutty. Master and Rick will surely approve :-)

I walk upstairs to the living room as I enter I see Master and Rick are very excited by my look. I curtsey and say, "Does Master approve of my outfit tonight?"

He says with immense pleasure, "Oh yes, Chantel, oh yes. You make one very cute and sexy, sissy slut."

Rick chimes in, "Fuck yeah George, I agree, she's fucking hot."

I smile and reply with another curtsey, "Oh thank you gentlemen, I feel so girly, sexy and slutty. I hope all the men who will have their way with me tonight will enjoy my dress."

Master replies, "I'm sure they will," he follows, "I also want to say that if you are a very good and cooperative sissy slut tonight. If all the men who will use you tonight are happy. I will actually let you have tomorrow, Sunday off." "And you will be able to dress as girly as you wish and just rest and relax. I will then automatically agree to free your sissy dick and let you play with it if and as you wish."

I so happily reply, "Master, you are too kind to myself as a sissy slave. But I will work even harder pleasing all the real men who will have their way with me sexually tonight in order to be granted a sissy day and play with myself day off. I love serving you my dear Master."

With that it's just past 6:30pm and we need to get on our way back to the cheap hotel and room #110. I have a busy night as a sissy slut ahead of me. Master reminds me that they have arranged 30 men to pound my sissy ass and 30 more men to fill my sissy mouth with glorious cock. I'm as expected terrified but also like a good sissy slut excited and wanting to please.

The drive out to the motel fills with excitement for not just me but for Master and Rick as well. As we arrive and Master parks, I soon along with Master and Rick step out of the SUV. I love the sound and feeling my feet make when I plant such sexy, spike heel shoes on pavement. We then walk to the motel's office and my heels gently click with each sissy step I take.

Entering we greet the manger again and I curtsey to him. He gives me a sweet, cat call whistle as I look so sexy, slutty and hot. I blush with sissy pride.

Master asks, "Is room #110 set up for tonight's gang rape?"

Frank the manager replies, "Certainly and a few of the guys are already here waiting in room #109. There are three video cameras in #110 set up to run full time over the hours that Chantel will be gang raped."

Master perked up says, "Good, good I like to hear that and that already a number of the men are waiting to enjoy having their way with Chantel."

I stand daintily and quietly hearing this sexual talk about me as a slut. It amazes me now as I drift into thoughts about with all that I do as a sissy slut. I think as the men chat, just a few short weeks ago I was living a rather normal be it in reality 'faux' male life. My sissy thoughts and crossdressing were all closeted. Now I'm standing in heels, fishnets, a short, slutty dress, wig and makeup at a cheap motel, only minutes away from hours of male gang rape on my sissy butthole and sissy mouth. I soon drift back from my thoughts to hear Master ask me if I'm ready to get started?

I sheepishly curtsey and say, "Yes, Master, I'm ready to service and please many, the stiff cocks of many horny men."

We all then walk to room #110. Frank opens the door and we all walk in. There is set up a low back padded dining type chair that has belts at its rear legs and attached to its arm rests, two more belts. The three video cameras are set up around this chair to capture different angles of my soon to be gang rape.

Master, actually takes my left hand and kindly walks me to the chair. He orders me to take each belt around the chair's rear legs and cinch them around my high heeled ankles. He notes they do not have to be tight, but secure to keep my feet properly restrained. I do exactly as I'm told and soon both my high heeled feet are secured with the belts.

Master has me then bend over the low back of the chair but before my wrists are secured, I am to flip my short dress up over my back. This exposes my buttocks and them being covered by my black, fishnet pantyhose and my black, satin panty. I then am told to pull both down to around my knees.

My sissy bottom and lower back with my sissy tattoo exposed is ready to be lubed up. Master hands me a tube of KY jelly, I squeeze some onto my fingers and I then begin to work it up and inside my butthole. Once I'm done I lean over the low back of the chair and Master then takes the belts around the chair's arms to cinch my wrists securely. I'm not in pain but it will not be the most comfortable way to be. The chair offers a bit of padding for my chest to rest on. Master see's I'm not too comfortable and actually grabs a pillow off the bed and stuffs it under my chest area. He asks if that feels better and I say, "Thank you and it does."

I'm nervous but again as a sissy slut, I am excited too. As I breathe a bit nervously, Master pets me by stroking my wig's hair. He then caresses my chin and has me look up at him. He smiles and tells me how proud he will be of me tonight. I thank him and tell him I wish to please him and all the men.

It is here where I find my first two sexual partners will be Master and Rick and soon both are readying to do me. Master will butt fuck me as Rick will face fuck me. As they begin to drop their pants and briefs, Frank walks to see the video cameras and check if they are all recording. All a'ok, Master begins to massage my butt cheeks with his firm hands and soon works to open my butthole. Rick waits until Master is inside me and in a few moments, Master's stiff cock is up and inside my butthole. He begins working me over. I struggle for a few moments but soon relax as he nicely thrusts his stiff rod inside me.

Now Rick takes his hard cock and presses open my mouth and as my lips part and my mouth opens to take his manhood inside. "Mmmf, ummf." I say. Rick gently face fucks me. Both men now work their tools of manhood in my two most popular sex holes. I am keeping as relaxed as I can and I fight pain and try to enjoy the lust up my butthole while I feel the texture and taste of a stiff cock in my mouth. Both soon work into a good frenzy as if they are in a competition with each other of fucking a sissy slut like me.

As both get closer and closer to their desirable prize of lust I feel their urge and it makes me want to be so open to receive their pleasure.

Closer and closer each gets and then I feel it, first Rick lets a wad of hot, semen fill my mouth. Oh it's thick and oh so gooey. I as expected swallow every bit of it. Rick with a panting gasp then pulls out of my sissy mouth. Luckily for me Master George is now about to blow his wad of thick, glorious, man cream up my ass. "Ahhhh, Ughh, Ahhh." He says as his load lets go nicely up my butthole. He then pulls his cock out from my butthole and sighs as well. I'm thinking, Oh my God what a feeling?

Master and Rick both pull up their briefs and pants and tell me I'm a good little slut as they step out of the frame. I thank them and am left tied down to the chair. I wait for the next two gents to arrive. As they walk in a soon to be long procession of butt fucking and face fucking begins to go on for me tonight.

For the next few hours it's basically two men at a time with stunning, stiff cocks shoved up my ass and in my mouth with pounding glory. The working over I get with each gent then letting go of their semen is great. It does not take long for cum to ooze out of my butthole and stream down my thighs to my knees and soaking my panty and pantyhose as well as some jizz dripping onto the room's linoleum flooring. In my mouth I swallow all the prized treat of thick semen by my face fucking, male sex partners.

After the first ten pairs of men have had their way with me, Master and Rick come back to the room. Master asks, "How are you doing Chantel?"

I reply knowing to be positive, "I'm doing well Master."

He goes on, "Do you need to stretch or anything?"

I say, "No Master, I'm ok. But may I please have a glass of water?"

Master says, "Ok, Chantel, let me guess you'd like to wash the taste of all that cum down your throat?"

I reply, "Yes, Master, but I'm enjoying the cum that I do get."

He and Rick both laugh a bit and Rick gives me a glass of water with a straw added as my hands are still tied down. It refreshes me. Master says for me to get ready for the next group of ten pairs of men.

He and Rick then leave, soon two more horny guys come in. It only takes moments for each to stuff my butthole and mouth with their stiff cocks. My butthole is wet and sloppy so it takes cock very well now.

These men pound my face and butthole. Cum soon fills my insides, both up my bottom and down inside my stomach. Another pair of horny men have their way with me. Each zip up and walk out.

By the time twenty pairs of men have had their way with me more and more cum has run down my thighs, soaking my pulled down panty and pantyhose as well as pooling up on the floor.

Master and Rick come back and untie me this time to let me stretch as well as take a bathroom break. Another glass of water and I'm tied back down to the chair.

My final push of ten more pairs of horny men begins. My butthole has been ravaged and the taste of semen fills my mouth so thoroughly. Knowing I've swallowed so much cum already has me feeling quite proud of myself.

I make it through the last ten pairs of men. I'm now spent, tired and my bottom side is a mess. Master, Rick and Frank all return to untie me, let me clean myself up in the bathroom. To which I wash my cum soaked panty and fishnets before I then pull both back up over my slutty hips. I then fix my short dress, fix my lipstick and walk back out to where the men are.

My buttocks are sore and my lower back is too by being tied up, bent over a chair, as I was in my 5 inch heels. Master has me wash the pool of cum off the floor and soon we are on our way back home.

It's late as it's now almost 1:30am. There is a lot of hours of good hard raw ass fucking and face fucking video that Master will later edit and upload. But soon we must be on our way.

We get home and Master tells me how proud he is of me tonight. I thank him and give a curtsey. He tells me I will have Sunday off and all to my sissy self, just as long as I dress up as expected and be sissyish and girly. I can put on a maids dress or any slutty outfit I wish when I awake in the morning. But to make sure though that I'm as always in high heels and hosiery. I can sleep in as long as I wish too as well. I will be allowed to have my sissy dick be freed from its cage once I awake and greet Master in the morning. I am so happy right now, I thank him and curtsey as he them dismisses me to my bedroom.

I change into my sleeping lingerie and pantyhose and as I drift to sleep I am proud of myself as I pleased Master so much that I get a full Sunday off.

Sissy slavery is hard life at times, but it's what any true sissy like me really wants and needs. The hunger for such a lifestyle is strong. Real men would not feel such, but 'faux' men who know that they are weak, effeminate sissies do know this. Master proves to me how fair of a Master he is. I LOVE IT! I LOVE BEING HIS SISSY MAID AND SLUT! Sunday will be a blissful day for me.

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8 Comments
Loverofincest69Loverofincest692 months ago

If I could change 4 things in this story it would be the the sissy would have licked up all the cum off the floor. And put on her cum soaked panties and hose without washing them. And put a pulg in after she was done.

AnonymousAnonymousalmost 3 years ago

The story is very nice. But here Chantel fails only one one point. While she is fucked, she doesn't write anything about her enjoyment while getting fucked. It appears that she tends to wrap up fucking sessions quickly. She should write how her sissygasm builds on and as she is locked in Chastity, a bodily-orgasm should happen. This is how sissies locked in Chastity tend to orgasm. They can't cum from their pricks. So the orgasm has to come out some way.

dacoach44dacoach44over 7 years ago
Lovely work

Such an enthusiastic girl; way to go, Hon!

Sissy_ChantelSissy_Chantelover 7 years agoAuthor
fucking machines...

njcaptionlover,

Thanks for your thoughts. Stay tuned for more chapters to follow. I've written or am finishing up some stuff that is going to be similar but not exactly as you noted. But the fucking machine(s) for one will be returning as the chapters come out here. Other sissy, hardcore sex will be coming forth, IMO some yummy endorphin stimulating stuff to cum! :-)

njcaptionlovernjcaptionloverover 7 years ago
Just an idea

Would like to read how Chantel is hooked up to two fucking machines and put on display on the adult store displaying how the fucking machines work.

Chantel should be made to do two more porn films.

1 where she is gang banged by dominate shemales

2 gang banged by women with big strapons.

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