A First Time for "Hannah"

First story, please enjoy and feel free to leave any feedback! Thanks for checking it out and I hope to write more!

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At age 24 and after years of dressing in private, I finally decided I needed to get out. I had been scouring online personals for some time but never got further than exchanging a few emails and trading pics. I had been in touch with other CDs from all over the country and had even considered traveling just to get a "taste" but ultimately, I just wanted to be someone's object of desire.

First I must explain my specific desire; I wanted a man or a woman, to want me. Period. Being treated like a whore wasn't my thing, and wasn't what I had in mind for my first encounter while dressed. On the other hand, I meant business, and I wanted a sexual experience I had never had before. I wanted to be desired, I have always enjoyed hearing what my pics cause in the pants of my admirers and wanted to be able to take it further. The thought of me, dressed as a woman, turning someone on made me crazy with my own desire. I wanted to please!

I had thoughts of visiting a local adult bookstore and checking out the gloryholes and someday I might, but that's not what I had in mind for now, I also had thoughts of being with another CD, again, not what I truly desired this time, I even (and always will) considered finding a girl who wouldn't mind strapping it on and getting me from behind. But for my first time, I wanted a man...and of course, his cock. I wanted to provide a "gfe" but like I said before I wanted to get down to business fairly quickly and maybe if he was lucky, stick around long enough to give him a double!

I had arranged a meeting with someone I had met on an online personal site, he went by Erik and he was just a few years older, his pics were great! He was well built and had a great looking cock, the kind that makes your mouth water with anticipation! We had exchanged pics, he was very kind and respectful of my wishes and first rule; discretion. I had recently purchased all of the necessities to go out, including a quality wig, makeup and of course, breastforms. All in addition to my collection of lingerie and sexy clothes. My job provides great pay and I spared no expenses while collecting these items.

He had suggested the adult bookstore glory holes or a private room, I wanted a little more privacy and wanted to keep it a bit more classy. When I suggested I pick him up in a rented towncar (with chauffer) for a quiet night out, he had no objections.

When that special Friday came I had already arranged time off work in order to prepare for my evening. I pulled out all the stops and made sure I didn't miss a single detail. Starting with a hot bath and full body shave I found I could hardly contain my excitement. I also wanted to make sure my performance was strong as possible, so in order to ensure I maintained control, I brought my toy into the bath with me. After a long session ending in an intense orgasm brought to me by my "friend", I was ready to start getting dressed.

After I picked out my outfit I got started with my makeup, I wanted a look that was innocent but still sexy, and classy of course. Once I was done with that I returned to my room, my outfit was laying on my bed, that's when it hit me. Standing there, in my lace cheeky panties, I was about to be someone's woman. I could hardly contain myself, it took all of my self control to not break out my BIGGER "toy" right then and there. I shook it off and began to get dressed. I started, like any girl, with undergarments. I put on my long black gartered minidress slip (so as not to show from under my outfit) and black thigh thighs. My 34d breastforms fit perfectly into the bra cups, I felt SO sexy. Next I pulled my little black dress over my head, I loved it and was SO excited because of the way it made my ass look and how much skin it revealed. It came down to my mid thigh and when I stretched just enough, my garter straps we barely visible, I LOVED that look. Next I pulled up my leather thigh high 5 inch heels, they were tight, but not that BDSM tight some people like. I had plenty of practice wearing heels at home, it didn't matter the surface I was on, I was a natural, stairs were little challenge from the beginning.

I turned to check myself in the mirror and was stunned, I couldn't believe how sexy I looked. Like I said before, I've dressed alone at home for years but this was the furthest I had taken it and I really, REALLY liked what I saw. I always knew I wasn't shaped like most men(though always prided myself as a handsome one), I had a shapely lower body and fairly slim stomach, chest and arms but at that point, seeing myself fully dressed, I knew I should have been born a woman! I felt like I could make a KILLING doing porn! I was everything I had fantasized about in a "woman" hundreds of times! Again, I had to practice restraint to not draw the shades and go to work on myself all over again. ;)

That was when I heard the horn honk. Shit, the car was early! I hurried into the bathroom to double check the details of my makeup and wig, put on some earrings and necklace and like that I was out the door. That's when I realized I hadn't planned the timing very well, it was still light out and a neighbor across the street was out watering his lawn, I smiled as I noticed him staring at me out the corner of my eye. Then, I opened the door and told the driver to head downtown. I had been practicing a feminine voice for some time and was fairly confident in what I had developed so I wasn't too worried about giving myself away to anyone who didn't need to know any "details". I was to pick Erik up from his loft then start the night with drinks.

He was waiting outside his complex as we pulled up, with a rose in hand. As he opened the door my heart stopped and time seemed to do the same, this was it. There was no backing out. He entered the car and sat down, handed me the rose and kissed me on the cheek.

"It's a pleasure to finally meet you Hannah"

I smiled, "Likewise, you look even better in person" is all I could say.

He told me he knew of a place where we could go and instructed the driver to take us there. Upon arrival, he stepped out and offered me his hand as I exited the car. I asked the driver to wait and off we went into the bar.

It was a dark place, somewhere I had never been, I liked it, it was sophisticated and sexy, he led the way to a booth in the back. I felt like people were staring and I think they were, we sat across the table from each other and talked as we had a few drinks. The server was a cute blonde and I could have sworn she was checking him out, I almost felt a bit jealous, but then it hit me, she obviously had a huge advantage and was actually the one that was jealous of me! After a few drinks I really began to loosen up, I was having a good time and with the way Erik was looking at me, I could tell he seemed to be enjoying himself as well. I decided to get a little closer to him and switched sides to be closer. As I was sitting down, I felt his hand on the small of my back, that itself was a huge turn on. I returned the gesture by immediately placing my hand on his thigh.

That's when it happened, our eyes met and he leaned in to kiss me, softly at first but we both wanted so much more. I began exploring his lap with my hand as reached his hand to my side. In no time, he we were tongue deep in each other's mouths and I could feel his cock growing hard with my hand that had now found its way tucked inside his pants. Our kiss broke, we looked at each other

"My place isn't far..." he started to say.

"Yes" I said, nodding, interrupting him.

He laughed as I blushed, I was SO turned on could hardly keep my composure.

We left the bar and got into the towncar. On the ride to his place, we could hardly keep our hands off each other, I was all over him and he was all over me. I mounted him, facing him as we kissed. I had his belt undone and pants unzipped and was rubbing his cock with both hands. I didn't even know we had arrived at his complex when looked down and saw the precum dripping from his rock hard cock. I wiped it up with a finger and brought it to my mouth. I started licking it off but was so excited I ended up sucking my own finger like a cock. That's when the driver knocked on the privacy window. We both laughed again at how carried away we had gotten, I readjusted my outfit as he zipped his pants, we both got out, I paid the driver and apologized for the waiting.

As we walked up to Erik's loft, I realized I was a bit drunk, I reached out for his arm to steady me and again he put his hand on the small of my back. I felt so womanly, I was loving it. We made it up to his loft and entered, it was nice, a corner suite with lots of windows. He led me to his bedroom and began to draw the curtains.

"No," I said, "can we leave them open? I've always wanted that"

He told me I could have whatever I wanted and stepped toward me, wrapping his arms around me and placing his hands on my ass. We kissed, long and hard, then, as if I was in a trance, I dropped to my knees and began undoing his belt and pants again.

I have never given head before but I have fantasized while practicing with dildos, and of course, tasted my own cum. But this was different, it was so warm, and he was a little bigger than my usual toys, I guessed him to be just over 8 inches, cut and a perfect shape. I started gently licking and kissing his head and shaft but before long I was taking him into my mouth and with some focus was able to take most of him in while massaging his balls with my free hand. I didn't even realize he had his hands firmly on the back of my head as he sat down on the bed and moved one of his hands to my "breasts". At that point I looked up at him, still stroking him with my hand and said, as seductively as possible

"You wanna fuck me, Erik?"

Without hesitation he answered with a yes and I pushed him back down onto the bed as I straddled him, still kissing him. He helped remove my dress, but we left everything else on.

I reached down, pulled my panties aside as he applied some lube he had nearby. He gently helped me guide him into my ass, it was a strain at first, I tried to relax as much as I could but he could still see that I was a little uncomfortable. He gently eased himself in and out, just a little at first but as I relaxed more and more he slid in further and further. It wasn't long before I was riding him hard, I loved the look on his face. He was smiling and I knew he was enjoying himself, that made me want to work even harder for him as I thrusted down as far as I could onto his hot member. He was holding my hips when he started to moan with anticipation, I kept driving myself down onto him.

At that point I felt him start to tense up as he squeezed my ass tightly, shortly thereafter I felt him explode his cum into my ass, it felt amazing, so warm, so REAL. I was in heaven as I came myself, soaking the inside of my panties. We continued our pace more gently, gradually slowing until I laid down onto his chest and kissed him.

"That was incredible." I said softly.

He replied, "Even better than I expected, we should make this a regular thing."

He was still inside of me as we laid there for a little while, kissing.

Later on, I got up to get cleaned up and as I walked out of the bathroom, I noticed he was laying under the covers in his bed.

"I thought maybe you wanted to stay?" he said.

"I'd love to." (what girl wouldn't!?)

He laid close to me, spooning me, it wasn't long before I felt him getting hard again, I turned around and slinked beneath the covers. I wanted his cum in my mouth, that's exactly what I got, and I loved every drop. Afterwards we kissed and cuddled until we both fell asleep.

In the morning, we exchanged numbers, he asked me to call him sometime as he smiled. I smiled back and told him to expect one very soon.