tagTransgender & CrossdressersAsh's New Life Ch. 01

Ash's New Life Ch. 01


Hello readers my name is Ashley, I am a twenty year old crossdresser. I started dressing around the age of twelve. This is one of many stories I have written. Some parts are real some are fake, I'll let you decide which.


My story begins very normally, one Saturday night some friends and I met up at a local alternative lifestyle club in town. We had some fun, kicked back some drinks and had some fun messed with a couple girls like me, although they had no idea I was a girl like them at times. At about 3 am I decided it was time to go before I went home with one of these girls. So I said my good-byes and walked out of the club. Heading to my car is when it happened, someone came up behind me and grabbed me putting a rag with something on it over my mouth and the last thing I remember is a guy saying, "sleep tight princess."

When I awoke I was chained to a wall my wrists at my sides, feet together, and a ball gag in my mouth making it impossible to scream for help. The room was pitch black, I couldn't see anything, then somebody came up and put there face close to mine. I turned my head to avoid any contact, then they pulled away and a woman's voice called out, "Hunny she is awake."

A male's voice calls back "good it's about time."

Then all of a sudden the room was filled with light, blinding me for a few moments. When my eyes adjusted the male and female were standing in front of me they're faces covered by ski masks. The man opened his mouth to speak "welcome back to reality. Sorry about knocking you out like that, but it makes it a lot easier to get you here and where you are now."

He stopped and the woman said, "we have a proposition I think your going to jump at. Hunny do you want to tell her?"

I'm thinking that's the second time she has referred to me as a girl but I'm a guy. At that moment the man interrupts my thinking. He says, "we have been looking for someone like you for a long time now. We want you to stay here with us as our 'daughter' and slave'. You must be wondering why we keep referring to you as a girl."

He looks at the woman and nods, she walks back and pulls the blanket off what I think is a portrait of some kind of a girl bound up just like I was. Then I noticed her head moved as I looked down at what I was wearing. I instantly realized the portrait was actually a mirror and the hot blonde in it was actually I. I just looked and stared for a few minutes and was interrupted by the guy saying, "do you like?"

I shake my head up and down, then the woman says, "if you stay here with us you can and will dress like this al the time."

Then the guy cuts in "so here is the bottom line, you can either stay with us or I can knock you back out and when you wake up you'll be sitting in your car. No questions asked and nothing ever said about it again. All you have to do is shake your head yes or no."

I thought for a second and decided this was what I wanted all along and shook my head yes. The woman walked over and hugged me as best as she could with me chained to the wall. As the guy pulled out some keys and starts unlocking my restraints. When he is done and I can move he takes me into his arms hugging me telling me he is glad I decided to stay.

They take they're ski masks off and am relieved to find out they are old friends of mine, who I will call Kris and bob. Then Kris walked over to a table in a corner and picked up my jeans and emptied the contents of them on to the table and said, "I guess you won't be needing these anymore."

And threw them in the garbage can. Then picking my keys up off the table she says she is going to get my car before the club has it towed. We start heading for the stairs and walk to the living room. We sit on the couch me in the middle while she calls a cab. We sit there and have small talk till the cab arrives. She gives her husband a long deep kiss and then me a peck on the cheek then she leaves.

As soon as she is out the door he turns to me placing his hand on my thigh. He tells me again how happy he is that I'm staying, then he moves in and kisses me softly and lovingly, he breaks the kiss a few minutes later and says, "you must be tired let me show you to your new room and lets get you ready for bed."

We get up off the couch and he leads me by the hand to the stairs and fallows me upstairs and to a door and lets me open it and we enter the room and he turns on the light. The walls are pink thick white carpets and it looks like a teenaged girl's room would. He asks "do you like it?"

I respond "it's beautiful"

He smiles and walks over to a dresser and opens the second drawer pulling out a baby pink silk nightie. He then walks over and sits on the edge of the bed and tells me to take off my shirt and skirt. So I reluctantly do what he says exposing my pink lace bra match thong and garter belt that's holding up black thigh high stockings. He hands me the nightie and I take off my bra and put the nightie on.

He then asks me to get on my knees between his legs. So I slide down to my knees between his legs looking up at him. He leans over and kisses me while I move my hand to his crotch and can tell his cock is hard as a rock underneath. I start to undo his pants and pull his cock out wrapping my hand around it and stroking it. He then breaks the kiss and I move my mouth to his cock kissing it.

I stick my tongue out and swirl it around the head then liking more and more till it is soaked with my saliva. I then move my mouth into an O and start to take his cock in my mouth. I look up at him as I slowly move my mouth down his cock. I slide all the way down and then back up it. I pick up speed with each stroke. After about 10 to 15 minutes he grabs me by the hair pulling my mouth off it saying "if you keep going I'm gonna cum in your mouth and that's not where I want to."

He stands up and helps me up taking me into his arms holding me. He then whispers in my ear "I want to fuck the cute little ass of yours."

I lightly moan my approval as his hands grab my ass. He then slides his hands up under my nightie and starts pulling my panties down. I stop him and turn around my but towards him bend over at the waist and pull my panties down around my ankles. I then look back at him and say "please be gentle daddy I'm a virgin."

He puts his cock at the entrance to my hole smiling he says; "I would never hurt you, much."

Then he slowly started to push against my hole it took him a minute but it finally pops in. he stays for a second letting my muscles relax and when they do he slowly slides in until all of it is inside me. Then he just as slowly pulls out till just the head is in then he picks up some speed pushing it back in and I groan in pleasure/pain. And he keeps at this speed till I get use to it then he picks up speed and so on until he is pounding me and I love every second of it. After about 30 minutes he pulls out and I get a sad empty feeling. He then says "lay on your back on the bed so I can fuck you like a real woman."

I do as I'm told and he takes my panties the rest of the way off for me and I spread my lags around him as he gets on top of me. I reach down between his legs and guide his cock to my hole and I moan as he pushes it back inside me. He instantly starts fucking me just as hard as he did before. I locked my ankles around his back and held onto by my nails in his back. He fucked me like his girl for about 30 minutes of constant pounding, all of a sudden I had an orgasm some how and shot my cum all over my nightie and then he groaned and came deep inside me. Then he says, "that was great baby, you can look forward to that more often."

"I enjoyed it too but I made a dress on my nightie." I told him with a sad face.

"That's ok put your panties back on while I get you another one."

I stand up and bend over picking them up then putting my feet in I pull them up. He walks over to the dressed and pulls out a blue silk nightie with white lace trim. He hands it to me and I change into it. I then climb into bed and he tucks me in kissing me on the head. He then leaves the room closing the door behind him, I fall right to sleep thinking about my new life.

To be continued...

If you liked this story or didn't comments and suggestions are greatly appreciated.

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bymaidashley69© 10 comments/ 136989 views/ 21 favorites

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