Meeting My Future Master

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When I got decent enough Darryl had me dressed up fully and took me into the car. I thought we were just going to go for a car ride and I'll suck him off. Instead we drove to a club that I never heard of, I was freaking out about going out in public. He calmed me down saying that it was a drag night and that it would be good for me to see other girls like myself. I was so nervous getting out of the car, I held onto his arm with all my might. It was crazy because when we got inside we got a lot of looks. I was worried that something was wrong but Darry just said it was because all the guys there wanted to fuck me and all the girls there wanted to fuck him. It was a bit of a ego boost.

The show was fun. It was nice to get out of the house and drink and have fun. It was like in the beginning when Darryl would take me to the bar after workouts although now my true self was out with him. It was nice to be close to him as Diane, have other people see but not worry.

After the show, Darryl and I went up to a drag queen called Jasmine, he knew her already, and they had mutual friends. He introduced me to her as his girlfriend which made my heart flutter a bit. It was weird being around talking to another "gurl" talking like girlfriends but it was also sweet. Darryl explained how I just started to dress and I could use some help doing my make-up. Jasmine took me by my hand had me sit down and she did a whole drag make over on me. Countoring, highlighting, fake lashes, the works. It was a lot to remember but the result was beyond anything I was doing at Darryl's place with the info I got from the magazines.

I was living the dream I had a hot bf who loved me and was helping me become the woman I was meant to be but never knew until I was living it. But then the two worlds I had would collide. The one where I was happy with a handsome, dominate black boyfriend and the one where I was in a loveless marriage would merge and only one will survive.

It has been 10 months since I first met Darryl and I was now dressing up enfemme for him anywhere from 2-4 times a week. I was wearing panties fulltime. When I would leave home for work I would have a bag in my truck of my car with stockings and even a corset that I would wear while at work. It was so erotic for me to have my girly things on while at work. I was able to do my make up a little bit outlandish but was comfortable being taken out by Darryl as Diane and having the world see me as his girl.

Darryl was preparing me to be his girl, one day while sucking him off while watching IR porn he stuck a finger inside my ass. It hurt a lot and was a shock but Darryl told me I would regret messing up on sucking his cock. So I just concentrated on his cock in my mouth as his finger slide in and out of me. I felt like his puppet with his finger inside me and like I was being ripped opened. After I got my prize of his cum in my belly Darryl took me to his bathroom. He told me that we were going to take a shower, I love being all wet with him. After the shower Darryl told me that I need to be clean all the time. He took out something that I never saw before, a douche. Darryl filled it up with water, applied lube to my ass and put the nozzle inside. The warm water filled me up, giving me cramps, I told him it hurt but he said that it had to be done. Once it was all in side he made me leave the water inside for a few seconds before I could sit down on the toilet and release. After it was all out he filled me up again with water, to get myself as clean as possible.

Now my insides matched my outside Darryl got a bag and took out a butt plug. First time I saw one and was frightened of having this thing inside me. Darryl asked me if I was his girl, I said yes. He then lubes up the plug and pushes it inside me. It rips my tight sphincter open, I tear up at the pain, Darryl caresses my back and he pushes it in calling me a good girl. It pops in, and Darryl tells me what I should wear it as much as possible. I walk out of the bathroom feeling the plug in me, another sign that I'm Darryl's girl.

Twelve months and I was happier than ever with Darryl. I was in the best shape I ever was. Life with Eve though was still a bit of a struggle. I was eating her out still but not communicating with each other. Going through the motions of being husband and wife. I was always looking forward to being with Darryl. All day he was always on my mind. Thinking about what he would have me wear, what we would do, his cock, or if he would take me out.

I went to his house to the backyard around 9pm. I stripped out of my male clothes, wearing stockings, garters, corset, bikini panties, bra and heels. I walk in and master is waiting for me. He hugs me and kisses me, I melt into his arms. He has a dress for me to wear and says we're going out. I get excited and we jump into his car.

As he's driving I get a bit nervous as I noticed that we're getting close to my neighborhood. I ask Darryl where he is taking me but he says it's a surprise. A coldness comes over me as I see we turn onto my street and he parks in front of my house. He tells me to get out, I say please don't do this. He says that it's the best thing for me. I stay in. He gets out and goes around the car and grabs me by the arm and drags me out of the car. He's pulling me towards my house, not knowing what is going to happen. Fear runs through me, what if Kevin opens the door and sees me dressed with Darryl. What is going to happen if Eve opens the door and sees me dressed with Darryl. I want to run away but Darryl's grip on me is too strong.

Darryl knocks on the door. Eve opens it and sees Darryl first. She looks confused as why is he there since I was supposed to be with him at the gym. Darryl doesn't say anything, he walks in towards her and kisses her. First time they kiss although during the dinners over the year master would flirt and touch her thigh gently in front of me. With the kiss I see Eve melt into Darryl's arms. I am free from his grip but I'm standing there at my door where someone who I thought was my man was now kissing my wife. I'm standing there dressed up for a night on the town as Diane looking at a scene I couldn't imagine.

The kiss breaks and Eve looks backs towards me in my dress. She doesn't say anything, she has a confused look but then realizes its me. Before she can even said anything Darryl says that she needs a real man in her life. He then picks her up, kisses her and walks upstairs. Darryl tells me to come along. Not knowing what to do I follow them. I'm glad that Kevin was sleeping already. We get into our room and Darryl begins kissing Eve more, stripping her. He asks what does she think of me and she says that I make a pretty woman. I'm standing there not sure what to say or do. He has Eve stripped laying on our bed. He strips himself, making out with Eve sucking on her breasts. His cock is rockhard and he lines up for Eve's tight pussy. He plunges in and she screams out in ecstasy and pain. He says to Eve that is what a real man's cock feels like. Not the little clit that I have. Watching this I'm totally humiliated, rock hard in my panties, my nipples are solid and I'm also jealous of Eve for getting to fuck my man before I have.

They fuck for about 30 minutes, missionary position with Darryl kissing Eve and playing with her breasts. She orgasms like I have never seen within ten minutes of Darryl fucking her. I'm filled with fear that Kevin will wake up and want to see what the noise is about. Its hot watching them together but I keep on imagining myself being in Eve's position taking Darryl's cock. She shudders with another orgasm as Darryl tenses up and cums into my wife's pussy. He asks Eve if she is on birth control, she says no. Darryl looks over to me and says that if I don't want Kevin to have a brother or sister I should get down there and clean up the mess he made with Eve.

Flushed with humiliation, not sure what to do, I walk to the bed, and go on it facing Eve's cum filled pussy. Darryl says that I know what to do. I go down onto her pussy and start sucking out Darryl's sperm. I do it for about 5 minutes while Eve moans from the waves of pleasure and Darryl stands over us. While I'm on my knees worshiping Eve's pussy I feel Darryl get on the bed behind me and lifts up my dress exposing my ass. His hands move around my pantied ass and pulls them down. I feel Darryl take my plug and takes it out with a small pop. He then lubes my ass and then I feel him enter in me finally. It hurts but I love it. He moves himself all the way in and slowly stars pumping away while my face is in Eve's pussy.

It feels so much different from plugs, fingers or dildos. It hurts, it burns, but I love it. As he keeps going I start to push back against his thrusts, I feel him inside me. It takes lots of concentration to keep eating out Eve and getting fucked by Darryl. I felt a wave of pleasure that started to build from his thrusts. After 20 minutes I cum from his fucking. I let out moans of pleasure. While I was being vocal Darryl cums for the second time that night in my ass. Hot with sweat and the pleasure of sex filled the room. Darryl gets off of the bed and I feel empty without him in me.

He gets up off the bed and starts to get dressed. He looks at us and says that he wants us both but we would have to submit to him fully. If we do not we would never see him ever again. With that he leaves the room and the house. Eve and I are still shocked and dazed by the events of the night. We get dressed, me in panties and sweat pants and tshirt. We then discuss everything that just happened and that has been going on the whole year.

I shared that I felt like a woman around Darryl and that I was happier now than I ever had been. We discussed our marriage and how it hasn't been one. We talked about the sex and how amazing it was. We had no idea what it would mean to fully submit to Darryl but we knew that if we didn't that we would regret it and our lives would still be fully changed by him but not happy. We agreed what we had to be with Darryl.

The next day Kevin goes to school and I get dressed up as Diane the first time around Eve. She comments to me about how my body looks different since I have been seeing Darryl. I've lost weight but my chest does seem to be a bit puffy but not buff. I dress up in clothes that I have in the garage. I knew that Darryl would appreciate seeing me fully femmed. Eve lets me borrow some of her make up and it was touching for me to be Diane around her and she commented how I seem happier with more of a bounce in my step being Diane.

I was still nervous going out the hose in the day time especially with neighbors but nothing happens. Eve drives us to Darryl house with me giving directions. We get to his house we have no idea what is going to happen. We go to his front door. He answers and we tell him that we love him and that we need him in our lives. He asks if we are fully submit to him as his slaves. We still had no idea what it really meant but we agree. He tells us to get down on our knees and take out his cock and worship it. Together we sucked our new Master's cock together. He cums on both of us. He tells us that we are no longer husband and wife in reality but his slaves. He tells us to give our wedding rings to him as a sign of our love and loyalty to him. We pause and look at each other but we do as he says. He then tells Eve that I was to always be referred to as Diane. After that he tells us that we can go to our house and that he would be over later that night and that we need to have a key for house for him. We then drive home in our separate cars with his cum still on our faces.

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8 Comments
AnonymousAnonymousover 4 years ago
Wonderful Story! Loved It!

I loved the story and would love to have this happen to my wife and I. My wife knows that I dress, but not of my desires to be a woman to a strong man! Love it and I can’t wait to see what the next installment brings as Eve and Diane become his slaves.

CdJenniferHCdJenniferHover 4 years ago
My Dream

As a sissyboy I have dreamt of being owned and trained by a BBC, this story only wants me to try harder.

stacejostacejoalmost 6 years ago
Loved it

My panties were Wett all the time....

SusanlynnSusanlynnabout 6 years ago
Very Hot

This had my little sissy clit leaking gurl juices all in my panties. Please write more!!! 5 STARS!!!!

sashatvslutsashatvslutover 6 years ago
Good

I enjoyed this story, but parts were painful to read. If you get someone to proof read, I think you'll have a hall of Fame worthy series.

I hope you keep writing and get better.

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