My first story. And it is the true story of my first encounter with a CD.
With a click of the mouse, I had committed…
I was going to meet a cross dresser just a few miles from home. Could I go through with it? Is it really what I wanted? Who was I kidding? Of course I wanted it. Now it was time to just suck it up, princess.
I took a quick shower and the dressed in my tiniest, sexiest briefs, painted on designer jeans and a white, button down shirt. I was as ready as I would ever be.
During the short drive, I was fully aware of my hard cock. It felt so good rubbing against my seduce-the-CD outfit.
In a matter of minutes, I found myself parking in front of her house. Confidently, I give the door a few knocks. I was in no way prepared for the vision that opened the door. She was slightly taller than me. Slender. Shoulder length blond hair. Pretty face with enough makeup to flatter, but not distract. She had on a sleeveless dress, with sequins. Cut to mid thigh. Beautiful black stockings that lead to heels. I’ve always been a sucker for stockings and heels…
“I’m Brianna, won’t you come in?”
“Thank you. You look incredible.”
As the door closes, she places her hands on my chest and pushes me against a wall in the foyer. Sliding up close, she nuzzles my neck. Her perfume was filling my nostrils. “This can’t get any better,” I think to myself.
How wrong that assessment would be.
Her lips traced up my neck as she leaned in to give me a tender kiss. How soft her lips were. Almost as soon as our lips touched, I felt her tongue probing. I open a little wider and soon our tongues are dancing as if we were long time lovers, knowing exactly what each other needed. My hand glided down her side, then between us, as I cup her cock from outside her dress.
“You will get plenty of opportunity for that,” she whispered in my ear, “But first, there’s something I want to do.”
As she drops to her knees, her hands travel down my torso. First they moved to my hard and sensitive nipples. They love attention, and were getting everything they needed as she pinched them. As her hands were busy above, her mouth pressed against my jeans. A few hot breaths against my jeans, and my cock was aching for more. I reach down and open my pants so she would have better access.
“Love the briefs.” She commented, as she proceeded to suck the head of my cock through the material.
I’m in heaven. A beautiful CD. On her knees. Sucking me in her foyer immediately after letting me in for the first time.
Her hands abandon my nipples, only to proceed directly to my briefs. Lowering the band so that my cock was now exposed, she engulfed the entire 7 inches, pushing it down her throat in one swift motion.
“Oh my GOD, Brianna! That feels soooo good.” My hands grab the side of her head as I pumped her mouth. This lasted several minutes, as she continued to slide up and down my cock. Her saliva making my briefs wet.
“I suspect that you didn’t invite me over just to unload in your foyer. Why don’t we find a more comfortable place to continue?”
Releasing my cock from her mouth, she agreed. “Follow me” as she took my hand and lead me to her room.
Once there, she gently pushed me to the bed. In seconds, my shoes were off. Next she suggested I lift my ass up a little so she can remove my pants and briefs. Then she straddled me, her crack teasing my cock. As she slid back and forth, the buttons on my shirt are releasing from her skilled fingers. With each opening revealing more and more skin, her lips traced down until they found my always welcoming nipples. Nibbling gently, they were soon very stiff.
My hands caress her thighs. There’s just something about the feel of stockings that get me every time. Traveling up, I soon cup her ass cheeks, bushing up against the thong she was wearing. My finger starts to put pressure against her hole, as she continues to grind against my cock. Surprisingly, my finger slides in effortlessly. Obviously, she had lubed up before my arrival.
“Mmmm. Deeper. That’s it.”
Her words are cut off as she presses her lips to mine once again.
“Put another one in.”
More rocking and grinding as two fingers are now buried inside.
“I think I’m ready for the main attraction.”
With that, she grabs hold of my cock and presses it against her hole. A few rocks of her hips and I’m in balls deep.
“Hold still for a minute. Let me get used to it before pumping.”
As her hips start to grind, I start long slow strokes. Her ass is magic. So tight. I know I can’t last if this keeps up. It just feels too good.
“Brianna, if you want me to last, we’re going to have to slow things up.”
“What I want from you is to enjoy the ride.” And with that, she starts to slide up and down my shaft. Hard. Fast. And determined.
The feeling is amazing as the cum wells up, ready to explode deep inside her.
“Uunnnnngggggghhhhhhh! Here is comes, baby.”
“Give it to me. Give Brianna your cum. Do it!”
My body trembles as I experience the hardest orgasm of my life. The kind where marching bands play, and fireworks explode overhead. As the tremors subside, she slides off.
“Now… what are you going to do for me?” She says as she works her way up my torso.
I had never sucked a cock before. But, it was clear she was looking for me to do just that. As her legs straddle my head, she pulls her dress up around her waist, pulls her thong to the side and lowers the tip to my lips.
“Suck it. Suck Brianna’s hard clit.”
With that my lips open, and she pushes the head in. What a sensation! So hard, yet so soft. Warm. It took all of two seconds to know that I like sucking cock. I swirl my tongue around the head. As she pushes in deeper, I let my tongue travel down the underside of her cock. My hands find her hips and I guide the speed and depth of the thrusts as my virgin mouth figures out what it can and can’t handle.
“Nice. Of course, this is just the appetizer.”
I hear the top of the lube clicking open. She has every intention of fucking me. Finally, I’m going to feel what it’s like to have a cock up my ass. Her cock pulls away from my mouth, as she settles in between my legs. The cold of the lube is pressed to my hole, and a finger slides in easily. Then two. I’ve played with plenty of toys, so I know I can handle her. The fingers go away, only to be replaced with the head of her cock. As the head presses in, I’m relieved to find no pain, quite the opposite in fact. It feels incredible as she presses all the way in.
Here I am, with a live, warm cock buried in my ass for the first time. Only, the visual is a pretty lady, in a sleeveless, sequined dress, between my legs. I laugh to myself and think, “Of course.”
She paused long enough to lift my legs onto her shoulders. Then, she proceeded to pound me for a good 20 minutes. Her stamina was amazing. I held on to her ass, pulling her deeper with each thrust.
“Oh… my… GOD… Brianna… fuuuuuuucccckkkkk me. Harder. Harder. I want to hear you slapping against me.”
“I’m cumming. I want you to take it all bitch.”
The CD is calling me her bitch? Guess if the shoe fits…
I feel her explode deep inside me.
She stays in me while we make out like a couple of teenagers.
As she pulls out, I thank her for being my first.
“Yes. And first cock in my mouth. And first cock in my ass.”
“Seriously? If that’s true, than you have natural skills that you need to embrace.”
And, we did a few more times before she left the area to follow a job opportunity. Wish she’d come visit some time…
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with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/crossdressing/my-first-time-4.aspx">My first time</a>