tagTranssexuals & CrossdressersMy Crossdresser Dream

My Crossdresser Dream


How do I reconcile my desires? I don't know. If I did the I would have done so already would have I? Oh well, here they are. The dreams of a semi closeted cross dresser.


We will start with the easiest thing to do, yet the hardest step I have yet to take. The blow job. Taking a cock in my mouth and sucking it until it explodes.

I can imagine it. I have dressed up and gone over to his house. I have been here many times before dressed as a woman. Sometimes the tramp, or the lady, or even just a normal girl. But never when he was a awake. This is not the sort of man that I would be prone to dream of. He is a friend. He is a neighbor. He is safe, yet so dangerous all at the same time. And yes he is gay.... where I am not. I am just a straight cross dresser that is bi curious. I need kid gloves to be used on me. But I don't know how this will go...

He answers the door in the usual way until he sees me. Then he is shocked. He ushers me in faster than usual. The conversation starts awkward and moves to more Q & A style. I finish with telling him that I needed him to know. I needed him to... I stop. I have to tell him. I have to tell him that I want to suck a dick. I have to tell him that I am curious. That I have to explore this sexual feminine creature inside me and the next step is to get his meat in my mouth. I have to tell him that I want to get on my knees and suck him Until he comes in my mouth. As he looks around out the door to see if the way is clear, and I know I have to blurt it out.

My words seem strange to me and I am not sure if it came out right. In fact I don't know what I said, might not even be what I thought I said. I want to explain... but I don't want to crush what little moment might be left. I ask him to sit or lay down. I am not specific so I am not sure where he is going... chair, couch, or, 'shiver' bed. He sits on the couch to my relief, but not before putting in a gay porn movie. I'm not wild about it, and am somewhat taken back... but I realize that he is a gay man and I am dressed as a woman. If I want that spongy head in the back of my throat, I have to allow him stimulus.

He is hairy and not my type... if I actually have a type. But he has a cock between his legs and he is willing to let me swallow it. It is bigger than I expected and smaller than I hoped. As I taste it I have to work my way slowly through the experience and he allows me to do just that. I want to gobble up his cock like it is my last meal, I want to be a real tramp and start sucking it for all I can. I don't manage that. I'm tentative like the lady I dressed to be tonight. But I hope I'm learning fast.

I think it is smaller than what it is. I find that out by trying to swallow him whole and gagging on him. I start to pull off but he hushes me smoothly, holds my head down... not deep in my throat, but not letting me off of him either. I will have to thank him for that. I wasn't sure if I was going to swallow his cum, or even let him cum in my mouth... now because he helped me be a real woman, I think I owe him that much. He pleads for me to take it slow, that I can suck him as long as I want. Strangely it does soothe me. And I work him deeper and deeper down my throat. But in slow methodical fashion.

I gag here and there. But finally, he lain completely out and I have swallowed him completely. I actually let it rest at the back of my throat for a second, enjoying the feeling of pleasing a man, the moment of taking it like a woman. I almost wish that I hadn't taped my own cock deep inside me. But I rub my smooth crotch hard anyways. I know that precum is trapped beneath the tape and in the cavity that I have made for my own maleness. But now I am just a woman, enjoying pleasing a man.

And I am apparently a distracted one. He starts by being a gentleman. Warning me he is about to cum and tries to get me off his dick. I start obeying him, but then I remember. I want him to explode in my mouth. I resist, and do so to forcefully. I jerk further down his shaft than intended. In fact I deep throat him. Which is far more than I can take and immediately he reacts by erupting with volcanic force. I am not in position, nor ready. I know that to swallow him I should have the head of his cock tight between my lips. But it's to late.

This is my second mistake as a brand new cock sucker. His cum gushes into and down my throat. I gag on it and it comes out around his shaft and out my nose. I try to resist the urge to pull off. I don't know if he senses this or I got myself in the position to encourage him, but he holds my head in place. Allowing me only to back up his shaft but making sure he kept cumming in me. I open my mouth to breath and am instructed firmly, "Swallow it bitch!" and I obey like the good girl I want to be... the good girl that I am.

I am sure that this is exciting him even more. He cums more with near equal force. Repeatedly filling my mouth with his seed while I, quick as I can, swallow it down. And then slowly the raging torrent of cum slows and stops, marked the jerking of his dick in my mouth. I pull off him and he instructs me to clean him off. I start to get up and he just tells me "No." I get it. I lick and suck the cum off of him. I am a good girl and lick his spent cock clean.

As I get up off my knees he tells me to get cleaned up. Start for the bathroom and again he orders me. "No, right here." I use my fingers to clean my face, then lick his cum off of them. He smiles in a almost cruel way, hands me my purse and tells me, "Fix your makeup before you leave." I quickly pull out my compact and in the near total dark quickly powder, clean up the mascara, and reapply my lipstick.

After I am done he hands me a bill, "I called you a cab." I am shocked. I absently take the money and allow him to usher me to the cab and open the door for me. He gives the cabby my address then adds, "Unless she wants to go somewhere else..." and then hands the cabby money as well. I am totally lost. Not sure if he said he or she to the cabby. The cabby laughs knowingly as he takes the money given him while I hold the money given me.

Embarrassed I quickly stuff the unknown bill in my purse. The cab starts moving. I just live behind where I gave my first blow job. The cab stops in the alley behind my own house. "Home? Or would you like to make more?"

"Home," my voice cracked. I don't know why I didn't just get out there. He went around the rest of the block and dropped me acrossed the street from my house. In the light, even if in the middle of the night. He handed me a card with his number on it with a lusty look in his eyes and he watched my ass as I walked across the street. I put that in my purse as well. Again not knowing why.

He honks as he leaves and I try to get through the door as fast as I can. I am breathless as I lock the door behind me. And shaking.

I make the bathroom and look in the mirror. There is still cum on my chin. I wipe it off with a finger and then lick that finger clean. My cell phone rings. I answer. "You have the makings of good cock sucker," the voice on the other end informs me. "I will fuck your mouth anytime."

Hanging up I sit heavy on the toilet seat.

The realization hits me. I will need more practice.

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byDaddyisaCD© 6 comments/ 65162 views/ 4 favorites

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