Becoming a Sissy Maid & Slut Vol. 02

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She replies, "My name is Jennifer and it will only be a few minutes, please have a seat Chantel."

I curtsey and then I sit quietly. People in the mall walk by the salon and most notice me, how can one not with a sissy maid in a black, maids dress, heels and hose.

Another lady then comes from the back and calls for me, I rise and face her then give her a curtsey with a yes ma'am. She leads me to her work table and asks me to sit. Again I curtsey and then sit.

She says, "My name is Linda, you are very polite Chantel with all your curtsies. You do not have to do so."

I reply, " Thank you ma'am, but I have to curtsey, it's a part of my lifestyle, my Master will not tolerate me not doing so."

She kindly replies, "Oh, ok I would not want you getting in trouble with your Master."

She and another lady name Monica carry on. I get my ears pierced and my large hoop earrings fitted and then my acrylic nails completed, all with a lot of small talk about me being a sissy maid.

Once my nails are done and polished with pearl, translucent polish, I note that I must now be extra careful when pulling up and on my pantyhose. Linda confirms with me being careful to do such. But soon we are done and I move up to the cash register to pay for it all. The ladies are all so polite to me and find me fascinating. I pay the bill and curtsey as I then leave, they all wish me luck in my new life.

I now walk to a department store inside the mall to buy some pantyhose, a bra and panty or two. Paying for this is all fun yet humiliating but people see me and understand. I then walk out to the parking lot and wait for Master to arrive to pick me back up. As I stand out in plain sight in my heels and wait, more people see me, giggle, give comments and take photos or videos of me. But soon Master arrives. I get in back his SUV and he asks for me to show him my earrings, nail work and what I bought for my sissy self. The guys like it. We then drive back to Master's home.

Once back home, I'm ordered to serve coffee and get on with preparing dinner. Ah life of a sissy maid and it's only just beginning for me. I then get on with dinner. Once ready I set the table. Master has told me where I will sit and were my sissy bowl and sissy mug will be placed. Once done, I enter the living room, curtsey and note, " Dinner is ready for serving everyone."

They all rise and be seated. First, I walk around and serve their plates. I then go around and pour wine and/or coffee for them, I curtsey with each serving.

Once done Master gives me permission to pour myself some cold, black coffee from this morning. Then I am to be seated. He then takes the small pot of plain gruel that I made for myself and pours some gruel into my sissy bowl. Cheap food is what I now get. Food for me as an enslaved sissy is to eat to live, not live to eat. Any special food that may be given to me in future will be a pure reward and at the pleasure of my Master. I thank him and begin to spoon it in my mouth and swallow.

Soon conversation moves to my special evening after dinner. My gang rape session by Master George, Sir Gage and Sir Rick. Again I only speak when spoken too. But when asked, I tell that I'm looking forward to the gang rape and having my anal cherry taken. Inside my head I am scared though as I'm sure that it will hurt.

Once dinner is done, the gentlemen all then retreat to the living room. I bring in a serving tray of coffee and dessert and as a good sissy maid serve each. Master sends me back to the kitchen to do the dishes.

It's now about 6:30pm when I am done. I go to the living room and curtsey as I state the dishes are done. The men are all excited as it's now coming time for my gang rape.

We all walk to the 'Punishment Room'. Entering we see a bondage bench. It looks kind of like a large weight lifting bench with a padded bench. Attached where one's feet may be is a welded bar and some padded, leather ankle cuffs. Up front is another welded bar where one can place their wrists in padded wrist cuffs and a padded base to place one's head/neck and can be strapped in place. It keeps one locked in bondage in doggy position. Looking at it I don' t think it's that comfortable. But comfort is not its real purpose, bondage fucking is.

Master instructs me to get on the bench. I do and I then strap my ankles in place. Before strapping my wrists in place, I am to pull up my dress, petticoat and pull down my pantyhose and panty. Master hands me some KY Jelly to lube up my virginal butt hole. I make sure to do it well. I then place my wrists in the cuffs, and Master does them up. Finally I put my head in place on the pad and my Master straps a collar to my neck. I'm without a doubt locked and defenseless. My anal penetration will soon begin.

I am very nervous but say nothing. Master has a video camera set up and recording on a tripod. He then stands in front of me and my locked in place face. He drops his pants and briefs, kicks both off. His cock is being engorged with lust.

He laughs as he dick slaps my face, then he asks, "Chantel, what do you want?"

I reply, "I wish to have you and the others rape me please. Please take my anal cherry."

Master then walks behind me. I can't see anything of what he is doing, but I soon feel his firm hands grasp my white, sissy bottom. He kneads it and then begins to pull my cheeks apart, thus my butt hole is totally exposed. He begins probing my butt hole with his stiff cock. But soon he has it pushed right inside me. Oh it hurts. But he begins to work my bottom over. Oh God between pain and lust it's an incredible feeling that I am having. The pounding Master is giving me is hard but now rhythmic. I'm almost delusional with feelings and lust.

The ass pounding he gives me goes on for a good 6-7 minutes. He thrusts harder and harder. I can sense he's about to blow his load of hot, creamy cum up my rectum. Once he shoots his load up in me the feeling is incredible. He is sweating and leans over my back and caresses my upper body with his hands, panting and then pulling out he says, "There you go Chantel, a joyful butt full of my hot cum. Your cherry is now taken, I own it and you have two more men waiting in the wings to do the same to you."

I say, " Oh thank you Master!"

Next up is Gage, it does not take him long to slip his stiff one in my now nice and wet butthole. His plan for attack is rapid and hard thrusts and enjoying the sound of me grunt and moan like the slut I am. Rapid, rapid, rapid with the sound of slop from my wet butthole. His ejaculation though is large in amount, gooey and thick. Sweat drips from his brow onto my lower back as his finishes his ejaculatory thrusts. And he is spent! Slurp is the sound made as he pulls his cock out my butthole. He walks away with wink and a smile.

Then finally here comes Sir Rick. He too begins by dick slapping me first as he laughs at me and I smile back. He then goes around and slaps my bottom asking me, "What do you want Chantel?"

With excitement, I tell him, "I would love him too fuck me too please."

He then pulls my still wet and sloppy butt cheeks apart and probes my wet butthole with his stiff rod. Oh my God he begins hitting me hard. It is an incredible feeling as he works my butthole over. He soon too reaches his orgasm and shoots his wad of goo up my butthole. Out his cock pops and he says, "That was great Chantel."

As he walks away. All this sex captured on video to be soon edited and uploaded for the social world to see.

The gents put back on their briefs and pants. Master releases the restraints from me. I get up off the bench but then fall to my knees before Master George. I tell him how happy I am and grateful for not only my gang rape tonight, but all that has unfolded in my sissy life to date.

He says, "That's good Chantel." as he orders me to clean myself up and meet them up in the living room when done. I am on my knees and bow with a thank you. I then stumble to the bathroom.

Wads of toilet paper are used to wipe both the KY and the cum out from my bum hole. I then pull up my panty, pantyhose and then adjust my petticoat and dress. As I walk upstairs in my heels, my ass by how it hurts tells me it has been violated by real men. I'm going to love being used as a slut from now on. I enter the living room and curtsey. Master tells me that I'm a good girl, I curtsey and thank him. He dismisses me to my bedroom and tells me to awake by 7:30am. Give myself an enema, shower and dress for another day of sissy slavery. He says we have another busy but exciting day ahead. I curtsey and wish them all a good night.

As I drift to sleep my first full night enslaved in my new home I think about my journey to date. It's been incredible. Though I have much more to endure.

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3 Comments
AnonymousAnonymousalmost 5 years ago
Wishing for more detail.

Wish there was more detail about how the cum tasted, and the feeling of having it down her throat and swallowing into her stomach.

Also, would have liked much more detail of her losing her anal cherry. How did it feel when the cock heads slipped in. Did she feel anything on her ass pussy clit?

hope the story gives these details going forward.

AnonymousAnonymousalmost 8 years ago
Love the story so far.

I think it would be great to be "her" . My pink lacy panties are so wet it is humiliating.

BonemealBonemealalmost 8 years ago
Very Sexy!

Yummy, I wish for some of the same stuff your story has. It gave me a boner even tough I have recently masterbated.

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