Becoming A Woman

[regina_allen55]

Background:
I am a 49 year-old crossdresser who is married only my wife dosen't know my secret. I have never been with a guy but the thought of taking him in my mouth dressed as a woman excites me. I love kinky and have a forced fetish. I am looking for someone who is interested in roleplay of my introduction.
My story:
My story starts when I meet someone on line and decide we should meet in person. I travel to a small town just outside where he lives. I check into a cheap motel and shower, then dress.
I'm wearing a short black shoe string dress with black lace top stayup stockings and heels, black lace bra and thong, with long red hair peach eyeshadow and red lipstick. There is champagne to help me relax. I have never done this before and I don't know If I can go through with it there is a knock at the door and I put down my glass and walk toward it. I hesitate as my hand reaches for the door handle

 

[msboy8]

New Character

OOC New Character

Jeb Stuart, Male 42, 6'1", 233 lbs, dark brown hair, a little more weight than he used to pack. Has love handles and a little "Budda belly". Used to cut through the female population with ease, but now he ia older.

IC

Jeb knocks on the door and waits. He is having second thoughts about the "On-line Dating" thing. Well, if she is a dog, he'll have his way with her and go his merry way.

 

[regina_allen55]

The knock at the door startles me and I take a last gulp of my wine. I run my hands down my thigh spressing my dress down as I make my way to the door. "What if he dosen't think I'm pretty?
"What if it's not him?
" he might have someone with him and there will be two of them?
So many questions enter my mind as my hand shakes slightly as I reach for the door knob. I turn it and pull the door inward.
You stand there, looking me up and down. My mind races and I breajke the ice.
" Hi I'm Regina"
You push the door closed and as you turn I push my hand out to greet you.
Your eyes roam my body as you come closer. You take myhand only you pull me to you. i feel your tongue
push past my lips and into my mouth as you use it to explore my oral cavity.You pull me against you and I feel your hands
on my buttocks kneeding them roughly. I try to pull away but you are too strong and you begin to over power me.
I fight to breath and hear my self as I start to whimper.

 

[msboy8]

Jen

Jeb continues his assualt on your mouth, his tongue diving deeper and deeper past your full red lips. His hands on your ass are relentless. Then suddenly, it stops. You find yourself falling onto the edge of the bed, perched there on your full ass, as if it was coreographed. You see Jeb standing there finishing off your glass as he oogles your breathless body.

*Hmmm, not bad, not bad at all. A little older than I'm used to, but what the hell, I'm getting older* "You are a fine looking woman", Jeb says as his eyes continue to rove over your figure.

 

[regina_allen55]

I look into your eyes and see them filled only with lust.the wicked smile which is now on your lips tells me that you plan to use me as your new sex toy. You are standing between my legs which have been pushed apart and my dress has ridden up, exposing my stocking encased legs with just the slighest hint of my panties.
I look at your crutch and see your cock, big and thick pressing hard against the soft material of your trousers.
Your eyes roam my body, each time your gaze stops at my lips.
"Please Jeb we need to take this a little slower"
You see my eyes becoming moist and the quiver in my voice tells you that I'm not prepared for what is about to take place.
You have already thought things through and you know tha I might not be co-operative but then you will take me anyway and will if neccessary use force to do it.
" I've"
"Never"
" Been with a man"
I stammer.
Your smile becomes even more evil as you gaze down at the scared prey before you.
I soon realise that my words will be fruitless.

 

[msboy8]

Jeb

"Never been with a man?", Jeb repeated. "Well then, Regina, we'll have to take it slow". Jeb smiled at Regina's relieved look. He takes your sweaty hands and brings you to your feet. Never letting go of you, he sits down on the edge of the bed. "Now let's take it nice and slow, darling", said Jeb, " just get on your knees and we'll take it real slow and easy."

Once Regina had got on to her knees in front of him, Jeb unziped his pants and freed his big, hard cock. "This will be your first lesson, darling", Jeb ordered with a big, superior smile, "just take this into your cute, little, mouth and see how it feels".

 

[regina_allen55]

You see the look of fear that still fills my eyes as you make me take it in my hand. I wrap my fingers around it's thickness and start to stroke it long and hard. Precum oozes from the eye, mixed with a touch of urine. I can smell the mustyness as it has been in your trousers ,waiting to become free. Your hand touches the back of my head and you exert pressure pushing my head forward.
It's as if I am remotly controlled as my lips part and my tongue darts out like a snake and I begin to lick the head of your swollen cock.
I run my tongue over and under the head,covering it with my wetness. You push my head again and I run my tongue down the length of your shaft, leaving a trail of my saliva and a hint of lipstick. You place both hands on my head and you manouver it so as I lick the shaft back and forth as I stroke your cock.
I take your swollen sacks which hand like hugh pendullems from your cock and take each one at a time into my mouth sucking and rolling each around my mouth.
You pull my head back and look deep into my frightened eyes.
I see your eveil grin telling me that what I am doing meets with your approval

 

[msboy8]

Jeb

*not bad*, Jeb thinks, as Regina's hot, wet tongue licks his cock. *She only needed a little urging, and her mouth feels so good. Taking my balls in her mouth, on her own too. I pull her head back and smile my approval.

*Never been with a man, well she can't say that now*, Jeb thought. "You are doing fine for the first time Regina, now let's see how much of my cock you can take down your throat", Jeb said tauntingly. "I can guarantee a big prize at the end"

 

[regina_allen55]

You hold my head tightly as you push more and more cock meat down my throat. My gagging is mixed with the whimper of some small trapped anmial as your cock head starts to pound my gag reflex. I breath heavily through flared nostrils as I try to breath Your hips thrust back and forth as you now begin to rape my mouth. Your cock feels like it's going to push through the back of my head as you pound my now aching mouth.
I knew this was a bad idea I think to myself as I am now feeling what it would be like to be a woman , forced to suck cock against her will.
you reach down and pull the straps of my dress down exposing the 1/4 cup black lace bra I wear beneath it. You pull it a way and expose my nipples.You take one in your hand as you still hold my head with the other.
You begin to twist and pull sending pain through my body. You like giving me pain as I try to cry out, only the sound is muffled with my mouth still full of your cock.
I know you have it in your mind to shoot your sticky seed down my throat as I can now taste more precum telling me that your climax is not far away.

 

[msboy8]

Jeb

*Oh her mouth felt soooo good*, thought Jeb as he pounded away at her mouth and throat, *She's gonna make me cum, the sly bitch. Now to raise the ante*

Jeb pulled Regina's dress down and ripped her bra off. Jeb smiled as he gave one of her nipples a little pinch. That and the way she flared her nose was enough to bring a loud moan from Jeb's lips.

He continued moaning as he lost control and he came and came again. His hot cum flodding Regina's mouth and throat. Jeb continued fucking her mouth until all his cum was released into her. He then let go of her head, but left his sated cock in her mouth to see what she would do next.