Dear Matt

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A crossdressers letter to her special friend.
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Dear Matt,

I'm so sorry that I took so long to get back to you. Every time I tried to write to you these last few days my wife walked in to the room so I had to stop and hide what I was doing. But the other day I got her. We were in the car and she was driving so I started to daydream about us,

We were driving around in your car together one night. Your right hand was lightly caressing my left knee and thigh while my left hand was lightly caressing your hard cock through your slacks.

We stop at a red light and you lean over and kissed me. The kiss is not just a small kiss on the lips but a long deep kiss where our tongues dance together while exploring each other's mouths.

All too soon we are interrupted by the people in the car behind us honking their horn at us because the light has turned green. We smile at each other as you drive through the now green light.

You are the perfect gentleman when we arrive at your house. You open the car door for me and help me out of the car and you wrap your arms around me, lean me against the car, and kiss me again. I can feel the cold car against my back while your warm body is pressed against the front of my body. I giggle, just a bit, as we kiss as I feel your hard cock pressing against me.

Once inside we sit on the sofa where we sip chilled Champagne.

What girl doesn't like Champagne?

You gently take my glass from me and set it on the coffee table. You lean in and kiss me again. This time you press me back on to the sofa as you gently lay on top of me. Your hands start to play with my small titties causing my nipples to harden under your fingers.

Your kisses leave my lips and work your way to my neck. I whisper "I love your kisses, Matt."

As you keep kissing me my hand slips between us and I grasp your hard cock and gently squeeze and play with it. You raise your hips and I undo your pants and my hand slides in and now I have your hard cock in my hand with nothing in the way of my grip I can feel your cock pulse and twitch in my hand.

Your hand slips inside of my bra and you grasp my small breast causing me to moan softly with pleasure. Your fingers start to pinch my fat nipple and tug on my nipple ring. I squeeze and caress your cock a bit harder causing you to moan a bit too.

You break our kiss and start to nibble on my nipples and tug on my nipple rings with your teeth some.

You slide down further and lift the hem of my dress up, slip my panties to the side, and start to lick and suck on my clitty.

I moan louder as I feel your hot mouth wrap around my clitty. I do not last long before I start to cum in your mouth.

Then you kiss me and we share a cummy kiss together.

All too soon you stop kissing me, stand up, and offer me your hand. I take your hand and get up. The hem of my dress falls covering my clitty as we kiss again.

The taste of my cum is still on your lips as we kiss. You lead me to your bedroom where you wrap your arms around me tightly as we kiss again.

You pull me down on to the bed on top of you. Then you roll me on to my back, still kissing me the whole time. I pull your shirt off and rub my hands over your strong chest then I slide your pants off of you so you are totally naked.

I move you on to your back and I kiss my way down to your wonderful cock. Looking up in to your eyes my tongue flicks across the head of your cock. The drops of pre-cum leaking out of the tip taste so good I smile at you.

I start to lick and suck on your balls while I rub your hard cock against my face as I keep looking at your smiling face. Slowly I start to swallow your cock, the whole time I look deep in to your eyes.

I grasp your balls and gently roll them in my hands and play with them as my head bobs up and down. I feel your hands on the back of my head as I swallow your cock.

Your cock swells in my mouth and you start to cum in my mouth. I swallow some of your cum but not all of it. As you finish your orgasm I try to suck all of your cum in to my wanting mouth.

With a smile on my cum covered lips I crawl up your naked body and kiss you sharing your cum with you, just as you had with me.

"I love our cummy kisses, Matt." I say with a smile.

You reach up under my skirt and slide my panties down as I'm thinking to myself, "I'm so glad that I wore a garter belt and stockings today."

Now that my virgin pussy is uncovered you start to lube it up. Slowly you slide a lubed finger into my virgin pussy, then a second one gently getting me ready for you.

As your fingers flutter in my virgin pussy my hips start to buck up and down with pleasure. "Please don't tease me Matt." I say in a gasping voice.

With a bit more lube in your hand you spread in on your hard cock.

"It's OK Sweetheart, you don't need a rubber, I'm on the pill. Besides I want to feel your hot cum in me as you make me a woman." I say softly as I bat my eyes at you.

You gently grasp my legs and lift them as you aim your hard cock at my virgin boi pussy. I gasp as I feel you start to press yourself at my wanting opening. You slowly press yourself in to me.

I gasp and wince at the pain and discomfort of being fucked for the first time. My cherry pops and you slide in all the way in to me.

Knowing that I'm a virgin you pause so I can get used to the feeling of your cock deep in me. Then I feel your balls lightly tap against me as you start to slide in and out slowly. Slowly at first then you start to pick up your pace. Soon you are thrusting in and out of my pussy with long, deep strokes.

My legs wrap around your hips pressing you deeper in to me.

I feel a warm fluttering deep in my belly that spreads up my body. As it reaches my brain I realize what's happening. "I'm cumming!!!" I cry out as you thrust as hard and deep as you can.

I can feel your hard cock swelling in my pussy as you grunt, "I'm cumming too."

I squeal with surprise and pleasure as I feel your hot cum shooting deep inside of my boi pussy making me a woman. Not just a woman but your woman.

I reach up, grasp your head, and kiss you as you finish cumming in my now no longer virgin pussy.

You lay on top of me as we kiss and I can feel your wonderful cock start to soften in me and start to slide out leaving me feeling empty but wanting more.

You slide off of me to lay next to me as we cuddle and kiss. I squeal a bit as I feel your cum start to dribble out of my pussy proving that you have made me a woman.

All too soon I have to leave. I slip my panties back on then you walk me to the door, still naked.

At the door I turn and we kiss, long and deep. A passionate kiss between two lovers, my arms wrapped around your neck as your strong arms wrap around my waist.

"Good bye Tiffany." You say softly.

"Not good bye Matt but see you later. I'll be back to be with you again soon." We kiss again as I grasp your soft cock.

When I get back home I change my clothes and put Tiffany away before my wife gets home. Not totally away because I can still feel your cum dribbling from my pussy.

My wife and I get to where we were going as I end my day dreaming. I can still feel my heart beating fast and I long to feel you in my pussy.


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