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First Encounter Ch 1

"Two cross dressers meet for the first time"

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Author's Notes

"My name is Monique. I’m a life long cross dresser in my mid thirties with limited experience. You are Jenny, slightly younger and more savvy in the womanly ways. We met on a cross dressing web site and after exchanging correspondence and pictures, we decide to take our relationship to the next level. <p> [ADVERT] </p>This is the story of that encounter."

We have arranged to meet for the first time at a hotel in a large city halfway between our home towns. I arrive first, pay for the room, and text you the room number.

While I'm waiting for you to arrive, I decide to get dressed. I remove my clothes from my suitcase and proceed to the bathroom. I strip down and admire my naked body in the mirror. I begin with a complete body shave, paying particular attention to my private area and rear door. I want these to look attractive to you so I take extra care to remove all hair. I then take a nice hot shower, cleansing every pore, again paying attention to my crotch and rear entry. 

I step out of the shower and towel off, beginning to feel the excitement of the upcoming encounter. I apply scented lotion all over my body and smile as I regard the reflection of my glistening body. I especially enjoy the glint of light off of my buttocks and hope you will find it as attractive as I do. I slip into my black lace thong, which barely covers my enlarging member. I also don my black lace bra and black thigh high stockings and begin to apply my makeup. I start with a light coat of foundation, followed by power, blush, and eyeliner. I complete my look with an application of bright red lipstick and don my wig, brushing it out and arranging it on my head. My finishing touch is a dab of perfume behind each ear and a pair of clip-on earrings. I twirl as I look into the mirror and am greeted with the reflection of a beautiful woman, eager to meet her new lover for the first time.

As I slip into my black Teddy and new red pumps, I hear your knock. I walk unsteadily in my new heels to the door and my hand is trembling as I reach for the knob. Fears and doubts flood my brain. What if Jenny doesn't find me attractive? What if I don't meet her expectations? My apprehension is eased when I swing open the door and am greeted by your warm smile.

"Hi Jenny, please come in," I stammer. 

You enter the room and we embrace. "Hello, Monique, it's quite nice to finally meet you, although I feel as of I already know you," are the first words out of your mouth. You are several inches shorter than me, especially in my heels. As you look up into my eyes, our lips are drawn as if by magnets to each other. We engage in a long passionate kiss which leaves me quite breathless.

"Oh wow!" I exclaim, "I've never kissed a man before." 

You look into my eyes and softly coo, "I'll not be a man for long". You wink, grab your bag and head for the bathroom to change. 

I am reeling with excitement as I stagger to the table and pour a stiff jigger of Scotch. I down it in one gulp as I hear the shower running. I tap lightly on the door and enquire, "Jenny, would you care for a drink?"

"What have you got?" you ask sweetly.

"Just some fourteen year old Scotch," I reply.

"That sounds lovely," is your response.

I pour you a jigger full and open the door to set it on the vanity. I catch an image of your naked body through the shower door and my heart races with excitement.

I return to the living room and pour myself another drink. I intend to sip it slowly, but the thought of having you naked in the next room causes all rationality to fly out the window. I down the second shot and set the jigger on the table. 

The Scotch is beginning to take effect on me when you emerge from the bathroom. I take my first long look at you and am stunned by your beauty. You are wearing a coral nightie, tan thigh highs, pink thong, and black pumps. Your makeup is flawless and you are sporting a shoulder-length blonde wig. I notice a distinct bulge in your thong which is barely concealed by the hem of your nighty. You twirl for me as I exclaim, "Jenny, you look simply delicious!" We embrace again and I get a whiff of your perfume, which is as intoxicating as the Scotch. Our ruby red lips lock, and this time, I'm not kissing a man, but the beautiful woman of my dreams. 

As we regain our composure, I notice the empty shot glass in your hand. "Refill?" I ask.

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"I'd love one," you respond.

With trembling hands, I pour you another drink and hand it to you. I notice your red nails and how they match your lipstick perfectly. "Your nails are lovely, Jenny. Do your toes match?" You slip one pump off to reveal your red toenails through your stockings. "You've covered every detail," I exclaim.

"I wanted to look my best for you," is your response.

"Well, you've certainly succeeded," I respond. I pour my third drink and raise it. "To first encounters." We toast and retire to the couch to get comfortable.  

 We take our seats side by side on the sofa and exchange small talk. We complement each other on our presentation and describe how we achieved our looks. I'm particularly interested in your makeup skills and you reveal that you had a professional make over to get you started. We share stories of our femme experiences, and just become acquainted with each other. I feel quite at ease talking to you and get the feeling I have known you all my life. 

As I set my now empty shot glass on the coffee table, my hand comes to rest on your knee. This brings a slight gasp from your lips, and I see my touch is having and effect on you. I notice a slight stirring in your thong, and your lips part slightly.

"Oh Monique, please go higher," you pant.

I trace the outline of your stockings higher up your thigh, and feel my own member begin to come to life. Our lips once again meet, and I revel at the slight taste of Scotch in your mouth as our tongues begin a slow dance. My wondering hand makes first contact with your extended shaft, and I get my first feel of your lovely appendage.

"Please don't stop," you breathe.

I think that I couldn't stop if my life depended on it. As I lightly stroke you, I feel your hand on my thigh, lightly caressing me. When you reach my thong, you pull it to one side and release my now fully stiff shaft from its confines. We continue our passionate kissing, each caressing the other's cock and stroking lightly. I sense a degree of shyness and hesitancy in you and decide to take the initiative.

To be continued.....

 

Published 
Written by Monique65
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