I've been dressing since I was ten, always being careful to never be seen by anyone. The whole time I grew up I'd never had any girlie clothes of my own but I'd always worn my sister's things, even used her makeup. I always made certain that she never ran out of makeup too quickly. When I knew I had the house to myself, I would dress up and pretend I was a girl. These sessions ended in a great masturbation with something usually deep in my tight little asshole, or boy pussy or ass pussy, as I've seen it called.

At any rate, that was quite some time ago and now, I was living on my own with the freedom to purchase whatever I wanted. To be sure, the closets in my apartment were full, almost overflowing, with dresses, skirts and blouses. The floor of them was filled with shoes of all styles and colors. But still, I'd never ventured out except a few times late at night and only for a short period of time.

Yes, I'd grown a bit bolder, finding a website where I could post pictures of myself in all my womanly glory and still remain somewhat anonymous. My masturbation adventures now included lifelike dildos, one that even squirted fake cum on demand and the photos I took of myself using these were also on the website. I really enjoyed that particular dildo and oftentimes practiced sucking it, pretending it was the real thing. I deep throated it on occasion then let it pump into my mouth.

I had a very good job in a large department store and I could wear quite a variety of things beneath my clothes, like garter belts and stockings, panties or a bra if I was also wearing a vest to hide it. Well, you get the idea. This is something I did on a daily basis and, in fact, I couldn't remember the last time I'd worn a pair of male underwear. My hair, which was longer than most men wear, was always kept back in a pony tail except when I dressed like a girl. The boss liked me, mainly because my performance was always professional an my sales were exemplary. He sometimes kidded me about my hair and general demeanor, but always in a friendly way.

On the website I made many friends, mainly with girls like me, but they were usually many, many miles away from where I lived. Often in other countries. I liked seeing their pictures, sometimes with them servicing a real man. We exchanged ideas and talked quite a bit. They encouraged me to try and get out in public but I was afraid someone would recognize me or “read” me as a man in girl's clothing.

Time passed and I grew bolder, going out in daylight and filling my car at a convenience store, though it was always on the other side of town. With my confidence growing, I would sometimes do my grocery shopping while dressed up but always in a very, very large discount store that also offered clothing and makeup, even televisions and other household items.

But even though I was now out in the real world, I felt lonely, having no real friends I could openly talk to about my secret identity. Then I met someone in my town who liked my pictures, all of them, and I was intrigued by his, though they were mostly of his dick. We talked online quite a bit and one thing lead to another. Before long, I agreed to meet him in a public place so we could talk face to face with me dressed up like a girl. That meeting would change my life forever.

We agreed to meet on a Saturday so as soon as I got off work on Friday, I went home and soaked in hot bath, shaving everywhere that needed it. I was mostly hair free to begin with but I enjoyed shaving my legs and pubic area. I had a hard time sleeping that night, either out of anticipation or fear. Even my normal masturbation and dildo sucking didn't help that much.

Saturday morning, I was up early and spent more time than usual getting dressed. I was, however, ready to go before it was time, dressed up completely in the way he said he'd like to see me. I was dressed casually: mid thigh length gray skirt, pale blue blouse, very sheer white bikini panties. I had on black four inch heels, light beige stockings and garter belt. My blonde hair was combed out with a loose flip under style, worn with dangling earrings, watch, and bracelet. I think I must have checked my purse a thousand times before it was time to leave.

When I arrived at the diner where we were supposed to meet, my stomach was filled with butterflies. I calmed myself as best I could and stepped out of my car. This was it, the moment of truth. Could I actually meet with someone even though we'd been talking for weeks? Taking a deep breath, I walked into the diner and looked around. I saw him sitting alone in a booth at the same time he saw me.

He stood and motioned for me to come join him. Too late to run away now.

“You're more beautiful in person than any of your pictures,” he said with a warm smile as I moved next to him. He was easily eight or none inches taller than me and very good looking.

“Thank you. You're very kind,” I said and slid into the booth opposite him.

We ordered iced tea and talked about nothing in particular for several minutes and I began to relax. The longer we talked the more comfortable I became and the more I liked him. Either he was a fantastic liar or he had no qualms about revealing his life to me. This was an entirely new and very thrilling experience to me.

Then he asked something which brought me back to reality.

“What do you think about bareback?”

“I uh, I've never done that,” I confessed. “I mean, I'm disease free and I intend to stay that way.”

“Exactly the way I feel about it,” he smiled. “But something I'd like to do is lick your sweet ass pussy.”

“You would?” I couldn't imagine anyone wanting to do that.

“Yes, I would. I'd like to eat your pussy, suck your clit, and then, fuck you really good. I want to cum in you, Dana. I want to fill you with cum and then watch it ooze out of you and make a video of the entire thing so you can post it on your site.”

I had to admit that his idea sounded exciting and it made my virgin ass pussy tingle with excitement.

“But would I get to suck your cock?” I asked hopefully.

“Of course. There's nothing so exciting as watching a girl sucking your cock.”

“And where would this all take place?”

“My house is available.”

I swallowed hard. Everything seemed to be falling in place but was I ready to have sex with a man?

“But you know, I'd like to get several pictures of you before we did anything. You know, some regular shots and then some that are a little more risque. Then we'll move on up to some where you're showing me your goodies and finally where my dick is in your mouth and pussy.”

“That sounds like it could be fun,” I giggled.

He pulled out his camera and took a facial picture of me laughing. Then stepping away from our booth he took a couple of more pictures, which were actually the first of me in a public venue.

Motioning me to get out of the booth he took pictures of me. A couple I know had a good view of my garters and my upper thigh. We moved on outside and used his truck as a background. Here I did some posing for him and yes, I raised my skirt a few times, showing off my panties and the silhouette of my small dick.

I enjoyed having my picture taken much more than doing it myself with a self timer. This was so much more exciting, or maybe it was the thought that before long I would be having my picture taken with his dick in me. This, of course, would be an added bonus to having sex with a man for the first time.

“The camera loves you, Dana,” Robert declared and snapped off more shots.

He wound up by taking a close up of my face while I smiled brightly for him. As apprehensive as I was when I arrived, that's how excited I was now. And not only was he taking pictures but he planned on a video as well.

“Would you care to follow me back to my house?”

“Sure. I mean, I wouldn't want to leave my car sitting here. Heaven only knows how long I'll be gone,” I giggled.

“Baby, I'm gonna fuck you nine ways to Sunday,” he laughed and walked me to my car.

“Just remember, I'm a virgin.”

“And I'm truly honored to be your first,” he said and patted my butt. Then he surprised me by giving me a kiss. A kiss with a lot of tongue involved.

Looking up at Robert I smiled and said, “I want you.”

“Then let's get moving, babe,” he replied.

The drive to his house didn't take long, covering only three or four miles, but during the drive I began feeling doubts once again. One part of me was unsure about what was about to take place and yet another part wanted to feel his cock sliding in and out of me.

As soon as we stepped into his house Robert took me in his arms and began kissing me deeply and I was kissing him back just as passionately.

His hands were all over me, caressing me gently. My own hands had somehow found their way to his crotch and I could feel the outline of his very impressive manhood.

“I want to suck you, Robert. I want to suck your cock,” I whispered. “May I, please?”

“By all means,” he grinned.

I found myself on my knees in front of him with my fingers fumbling with the opening to his pants. After a few moments, I had his zipper down and was fishing inside his shorts. I couldn't believe the size of his cock when I grasped it with my small hand, though I had nothing to base a comparison on. When I finally pulled him out into the open I was in awe of the beauty of his cock. He was, I guessed, about eight inches long and close to two inches around with a large deep purple head and he seemed to be growing even as I looked.

“You're so big!” I gasped.

Holding him in my hand I leaned forward and kissed the tip of his dick, letting my tongue snake out and taste him at the same time. Several more times I kissed and licked his throbbing cock, loving every second of it. When I took him in my mouth I shivered with excitement. It took me a few seconds to figure out that he was taking pictures of me again.

“Oh, Dana, that feels so damn good! And you look so fucking sexy sucking my cock!”

Feeling his cock sliding in and out of mouth, over my painted lips, was more thrilling than anything I'd ever imagined. I think I could have spent the rest of the day sucking his wonderful cock.

While I was sucking him, Robert removed the remainder of his clothes and now stood before me completely naked. He pulled me to my feet and then picked me up and carried me up the stairs to his bedroom.

After taking a moment to set his camera in motion, he kissed me deeply and opened my skirt to let it fall to the floor. Shortly afterward my blouse and panties joined them. He guided me onto the bed and positioned me on my hands and knees.

I felt him moving behind me and then was shocked to feel his tongue dancing along my puckered little hole and then plunging inside.

“Oooo, baby,” I moaned, wiggling on his tongue.

A few minutes later I felt him applying lubricant to me and I assumed he was ready to enter me. I was half right. Robert slid a finger into me and began working my little hole open. It felt wonderful instead of the blinding pain I had anticipated. Then he added a second finger, stretching me open a little more.

“Oh! Oh! It feels so good!” I gasped as he slowly moved his fingers in and out of me.

“Get ready, baby, I'm gonna fuck you!”

“Yes! Yes! Do it! I want you cock inside my ass pussy! Oooohhhh, baby, fuck me good!”

His cock was bigger than his fingers and when he pressed forward I felt myself being stretched to unbelievable lengths. It hurt and felt wonderful at the same time.

“Oh! Oh! You're so fucking big! It feels so good. Oh fuck, you're spitting me in half! Do it! Do it, baby!” I squealed as his cock slowly worked its way inside me.

By the time he was completely inside me I was panting like a bitch in heat. Maybe I was. But damn, it felt so wonderful to have a man deep in my ass pussy!

Robert slowly backed out until only the head of his cock was inside and then moved back into me. Again and again he slowly repeated the process and I thought I might be losing my mind because it felt so good.

“Yeah, baby, fuck me... Oooohhhh, it feels so good!”

Slowly and steadily he moved back and forth, gradually building the strength and speed of his thrusts until he was giving it to me hard and fast. His balls slapped against me with each stroke.

“Yyyesss! Yyyesss! Oooohhhh yyyesss! Fuck me hard, baby, fuck me hard! Oooohhhh, it feels so good!”

By now Robert was pounding me, each of his lunges harder than the one before.

My body began to shiver and shake and when I looked between my legs I saw that my own dick, though no erect, was spewing a stream of cum.

“I'm cumming! I'm cumming!” I cried. I couldn't believe I was actually cumming, though I'd read of such things happening. Even when I finished he continued to hammer my ass pussy with hard thrusts, keeping me flying high.

“Oh fuck! Oh fuck!” Robert bellowed and really slammed into me, holding my hips and pounding me harder and harder.

I knew he was about to cum in my ass, “Yyyesss! Yyyesss! Now! Fill me now!”

Driving as deep as possible into me, I felt his cock begin to twitch and then a magnificent heat began spreading throughout me. He was cumming in me and I was loving it. I loved the feel of his seed filling me; loved knowing that I was accepting the treasure he was giving me. Never in my life had I felt more feminine than I did right now.

When he pulled out of me I felt some of his sperm flow from my freshly fucked ass pussy, oozing its way down over my balls. I imagined that this had to be similar to what a woman felt after a man pumped his thick, hot seed into her. I held this position for several minutes as he snapped more pictures.

Robert pushed me down and rolled me over so that I was covering the wet spot created by both of us. He moved beside me and kissed me passionately before just holding me close to him.

“You are fantastic, Dana,” he said and kissed me again.

I responded to his kiss and let my small hands move over his powerful body and down to his now flaccid cock. Holding him in my hand I could feel his heartbeat and then I felt him growing before I slowly stroked him, urging him back to full glory.

“Will you cum in my mouth?” I asked when it was evident he was able to perform again.

“Is that what you want, Dana?”

“Yes, it is. More than you could possibly know,” I said and pushed him onto his back as I slowly kissed my way down to his glorious cock. “I want to suck your dick and swallow your thick cum. May I? Please?”

“How could I possibly say no?” he replied and grinned as I zeroed in on his manhood.

When I took him into my mouth, I could taste where he had been but I didn't care. In fact, that knowledge only made me more determined to give him the best blow job he'd ever had.

Even though we started with him on his back and me moving up and down his throbbing cock, we somehow managed to change positions. He was now on top. Robert was straddling me, literally fucking my face but at a much slower pace than he'd fucked me. He would stop and let me play my tongue all around his bulbous head and then he'd slide all the way inside until his pubic hair was tickling my nose. There were times when I thought I might gag but I fought back that urge and continued on my mission.

While I sucked him, Robert greatly distracted me by stroking my much smaller dick and it was evident that he wasn't going to stop until I exploded. I managed to forestall the explosion by concentrating on his dick, using my tongue to massage him, coaxing him to give me his load.

My moans and groans grew more insistent as he stroked me and all too soon my body gave in to his demands and began moving with him. I started shaking and bucking and knew he was going to make me cum before I could get him to give me his.

“Do it! Do it, Dana! Cum for me!”

With my mouth full of his cock I began to squeal uncontrollably and send my hips up from the mattress. My cock was taking control of my actions and showing no intentions of backing down. I shook mightily and then I felt my own release and then felt my cum rolling down my shaft. I was cumming hard and I know it was much more than when I masturbated.

Then it happened - I felt his cock growing harder and thicker in my mouth just seconds before he began pumping his seed. I had to swallow and then swallow again but I could also taste his wonderful cum. I had done it! I had given him a blow job! I was happy and very content, holding his cock in my mouth and coaxing every last drop of his cum from him as he smeared my own sperm all over my dick and balls.

I spent the weekend with Robert and he fucked me several more times in different rooms of his house and in a variety of positions, most of which I'd never dreamed of. Before I left Sunday evening, Robert had agreed to become my partner in crime. He would photograph me all around the city and I would be his steady fuck. Every weekend for six months he would take me somewhere and then take pictures of me in various stages of dress. But those stories will saved for the next chapter.

To be continued.