tagTranssexuals & CrossdressersFirst Time Sissy Maid

First Time Sissy Maid

bybart2077©

I had been fantasizing for many years about serving a dominant Mistress, watching lots of movies online, and generally lusting over the doms I saw posting ads. At the age of 28 I finally found the courage to answer a rather intriguing post by an older woman and her trans partner who were looking for a sissy maid for ongoing service. I answered the ad, included a couple of vanilla pictures, and was rewarded a few days later with a response. We chatted online a bit and I answered Mistress Red's questions as honestly as I could about my desire to be transformed, humiliated, and to generally serve her in any way she desired. We arranged to meet in person at a local coffee house.

I arrived for our meeting on time and found my new Mistress sitting at a corner table with no one else within earshot. She was beautiful. About 50 years old, tall and plump, with long curly blonde hair, very large breasts and a big beautiful ass. She was absolutely the BBW of my dreams. I sat down with her and we chatted casually for a bit before she delved into a few very pointed questions. She reiterated that she lives with a transsexual partner (Male to Female) who would be present during some of my service. I was asked about any bisexual fantasies to which I admitted to having a few but had never acted on any. Mistress Red was quite clear that if I was accepted I would be expected to dress in a full french maid's uniform, to clean and cook, take any punishment she saw fit to dish out, and to serve both her and her partner (Jordan) in any way they wished. My cock was so hard in my pants by this point I thought I would explode. I agreed and we left the coffee house and I followed her to her house.

Upon entering Mistress Red's home, a nicely appointed single family house with lots of privacy, she instructed me to follow her to the guest bedroom where she would help get me dressed. I stripped naked at her command and she took her time inspecting me. I felt so vulnerable and humiliated as she worked her way around my naked body, squeezing and pinching, and otherwise looking for reaction. She spent a bit of time on my cock and balls before working her way around to my little butt hole.

"What have we here? Hmmm? Is this a virgin ass I see?"

"Yes, Mistress, it is"

"We'll just have to see what we can do about that. There's nothing I enjoy more than seeing the look on my little sissy's face the first time his ass is stretched open."

"I don't know Mistress, I'm not sure I'm ready for that." I said still thinking that I had some choice in the matter.

"Oh, no worry my little sissy. We'll take things nice and slow" Mistress Red giggled at her own comment and gazed at me wickedly. "Now let's get you dressed. Hurry little sissy!" she commanded as she spanked my ass.

Mistress Red dressed me in thigh-high black stockings and five inch heels, garters, and lace panties. I could tell she was getting turned on by the progress she'd made and I must admit I was feeling very slutty in my new outfit. Next she attached breast forms to me, added a black lace bra, and pulled a lacy french maids dress over my head. The dress hung down just past my panties and revealed a bit of my stocking tops and garters. Next she went to work on my makeup and added a jet black wig to top it all off. Looking in the mirror I could not believe what I saw. I looked every bit the hot little slut!

"Now before I put your lipstick on why don't you do your Mistress a favor and get down on your knees, hands behind your back grabbing your heels. That's good. Now I want you to start your cleaning duties with my ass. You've got me so turned on I'm starting to sweat. Now clean it up."

Mistress Red pulled off her jeans and panties and exposed her big fat ass right in front of me. It was big and round with a deep ass crack that I was dying to taste. I leaned my head forward a bit and nibbled at the tops or her legs right where they met her butt cheeks and was rewarded with a little groan. I worked my tongue gently up her crack, going a little deeper with each swipe until I was smothering myself in her beautiful ass. Finally my tongue found her asshole and I licked all around it and ran my tongue up and right inside. Loving the taste and the noises I was hearing from my Mistress. My cock rock hard in my panties.

Finally Mistress Red stepped back and asked me how I liked that.

"Oh Mistress, I love your ass! I'll do anything to be allowed to worship it. Please may I have some more?" I squealed at her in my best little sissy voice.

"Of course you may. First let me fix your makeup and add a bit of red lipstick. Then after I take a few pictures we can talk about the other things I'll need from you."

Mistress Red proceeded to take several shots of me with her digital camera. Closeups of my face, full body shots of me dressed as her sissy, and even one of me on my knees begging like a puppy. She left the room and came back about ten minutes later to inform me that she had uploaded the pictures to several online email accounts and I was now truly hers to do with as she pleased as long as I didn't want the pictures to find there way to my coworkers and friends. At this point I was less scared than I probably should have been as I wasn't imagining anything I wouldn't do for this big beautiful Mistress.

It was then I heard the front door open and Mistress Red's shemale partner enter the house.

"That must be Jordan! Mistress Jordan to you, sissy. Oh, she'll be so happy to see you! Mistress Jordan loves getting her big cock sucked by little sissies after a long day." Mistress Red had a very evil look on her face and was giggling at my as she watched the fear spread across my face. "Now remember sissy, I've got all the pictures of you I need so you do everything Jordan wants and you do it with enthusiasm. Think back to all the little porn movies you've watched with sluts sucking on big dicks and you act the same way those women act." Her voice softened a bit and she added, "If you do a really good job I'll let you lick my asshole afterwards to reward you."

I was shaking quite a bit as Mistress Red led me out to the living room and introduced me to Mistress Jordan. The moment I laid eyes on her a bit of my anxiety subsided. She was actually a very beautiful and passable TS. She was sitting on the couch but I could tell she was tall, with dark brown skin, longish black hair, big round breasts and killer legs under a tight dress. Maybe this wouldn't be so bad after all...

"Introduce yourself, sissy!" Mistress Red barked.

"Hello Mistress Jordan. I'm Janey your new sissy maid. How may I serve you?"

Mistress Jordan looked me up and down and giggled a bit as she sent me for a glass of wine. I returned with her wine and knelt by her feet as she sipped at it. I was really getting into the part and felt like an absolute sissy submitting myself to a mature mistress and her shemale friend like this. But still, part of me, most of me, wanted to be completely used and abused by these two.

Mistress Jordan sipped at her wine as she looked down on me. One hand reaching up under her dress and starting to play with what looked to be a very large black cock.

"Come closer sissy, lick my panties and make your Mistress's cock hard." she whispered to me.

I crawled forward, nervous as hell, but went ahead and scooted her dress up a little exposing her panties and the cock trapped beneath. I put my mouth against the lace and began to kiss and nibble at the cock underneath. A girlish moan escaped my lips before I even realized it and my face turned beat red as both of my Mistresses laughed out loud.

"I knew you'd be an easy one to turnout" Mistress Red said. "You played coy in our online chats but I knew the whole time you'd be a good little cocksucker! Now take that cock out and get it in your mouth, whore!"

In just a few moments I was greedily licking at the head of Mistress Jordan's cock which appeared to be at least 8 inches, perhaps a bit bigger, and very think.

"Get it in your mouth! Suck it you little sissy!" Mistress Red barked at me and I noticed a video camera now in her hands recording every bit of my humiliation as well as the now frenzied look on my face as I fought to get as much of Mistress Jordan's cock in my mouth as possible. I was gagging and drooling but also loving it. I could not have imagined how absolutely slutty, whorish, and fullfilled having a cock in my mouth could make me feel and I was in heaven. I was now sucking for all I was worth moaning around the cock in my mouth and squealing like a little slut. Mistress Red was recording every moment and laughing to herself. I was a cocksucking sissy whore now and I was loving it! I was licking Mistress Jordan's balls and down to her ass, rubbing her cock all over my face and drenching it with saliva. It was hard as a rock and I knew she would cum soon.

"Time for our big finale, sissy." Mistress Red said as she moved in closer to get every bit of this on film. Mistress Jordan took the cue, stood up and jerked her cock right in front of my face.

"You open up that mouth, sissy, and you take every drop of that cum. I want you licking at it like it's the sweetest thing you've every tasted or this video is going straight out to your friends."

I pushed my tongue out of my mouth licking at the cock bobbing up and down in Mistress Jordan's hand only inches away.

"Please give me your cum, Mistress!" I squeaked. "Please cover my face and tongue with your cum. I need it. I'm such a whore, I'm your little cocksucker, please cum all over my face!" I begged in my little sissy voice.

"I knew you'd love this you cocksucker!" Mistress Red said. "Give it to him Jordan. He's been a good sissy. Cum in his slutty little mouth."

At that point Mistress Jordan let go a stream of cum that shot straight into my open mouth. It was sweet and salty and I actually craved more of it as soon as it hit my tongue. The second stream traced a line from my chin up the right side of my face. I leaned forward and took her cockhead in my mouth and sucked as hard as I could, working my tongue around her head as more cum came gushing out. I swallowed as much as I could and then used her cock to wipe up the cum on my face, licking it off and moaning and making yummy noises the whole time.

Mistress Jordan collapsed back on the couch and watched me lick up the rest of her cum.

"Well my little sissy," Mistress Red said, "I'm shocked at how quickly you took to your new duties. How about we try to stretch out that little sissy pussy of yours next"

"Yes please, Mistress!" was all I could say.

And I meant it.

To be continued.....

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by Anonymous

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by Anonymous09/16/14

great start

Can't wait for the next chapter. So looking forward to a sissy maid being fucked for the first time. I too was dressed as a french maid the first time I was fucked. I had sucked quite a few cocks by thenmore...

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by Meenachavan08/29/14

I want to read next chapter

Love this story and want to read more

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