Fantasy to Reality

So there I was, my stockinged legs resting on his shoulders as he pumped me relentlessly with his thick hard cock. My panties were long gone, allowing my boy clit to slap rhythmically against my stomach. The suspender straps were still just about attached to my garter belt and my bra clung to my D size breast forms. And I was in complete heaven.

—

I suppose this was in some ways inevitable. I was never the most confident of young men. I never thought myself gay, I always lusted after girls, but being 'blessed' with a tiny dick and a skinny and lightweight physique, I never had the confidence to do anything other than look from afar.

Truth be told it was when I discovered porn I got interested in lingerie. I was drawn to videos of women getting a thorough fucking in all sorts of positions while wearing stockings, suspenders and baby dolls. I was attracted to the women myself, to how sexy their attire made them seem. I used to wank furiously as I thought of plunging my little dick in them over and over again.

However over a period of time my thoughts and beliefs changed. For some deep down reason I started imagining what it would be like to dress like the women in the videos and make a man desire me in the same way. What would it be like to have the power to propel a man to those levels of lust? How would it feel to drive a man so wild with a sway of the hips or a cross of the legs that he would want to fuck me senseless? I couldn't shake the thoughts from my mind.

Living at my parents it was relatively easy to secretly experiment with my Mother's wardrobe. While using her panties gave me some encouragement in my feelings she possessed little else that helped my urge.

So online I went. A pair of black stockings, a matching garter belt and a cheap lacy baby doll was my first order. It did the trick, I was hooked even as I undid the packaging. I couldn't believe how sexy wearing lingerie made me feel. I started ordering more, spending hours trawling sites looking for something special. I bought a 6 inch dildo early on and had the deepest, longest orgasms I had ever experienced as I bounced on it dressed in my hottest lingerie.

Porn helped. I would watch almost mirror images of myself on the computer screen getting hammered while I pounded away at my ass. I rarely lasted more than a few minutes when I really got into it, even though there was a gnawing emptiness afterwards. I yearned for more.

Along with my physical wardrobe came the endless fantasies. Taken in a hotel room by a stranger. Or naked in the woods over a fallen tree as my moans carried through the undergrowth. Or in the boardroom at work against the tall glass windows while others worked in nearby buildings. Or beside a roaring fire in a log cabin in wintertime, where the sensual fucking lasted hours. Even with one man at each end, spit-roasted and drinking down semen while being endlessly battered from behind.

But that's all they were. Fantasies. I knew I would never experience them, I was too cowardly. I could get by like this. Perhaps pluck up the courage to buy a rocker machine one day to make it more 'interactive'. That was going to be my life and I was resigned to it.

I did start getting deeper into the dressing up however. My parents were often away at weekends and I had the run of the place. Often I would put on full sexy attire underneath sweat pants and a baggy top. I'd answer the door to the delivery man, walk around the garden, that sort of thing. I'd do the washing up or ironing minus the sweats. At the end of the day I would treat myself to my dildo while trawling the internet and look forward to the same the next day.

And then came Mr Nelson.

He lived next door. I didn't know him well, my parents mentioned he had split from his wife a year or so ago, no one knew exactly why. I didn't know what he did or what he liked. He was around 15 years older than me, a big man, over 6 foot and well built too. Definitely looked like he worked out. I did think I'd seen him look at me for a bit longer than is usual while I was in the garden once or twice but I'd dismissed it. He wasn't someone I thought about very much.

One spring day I was going about my chores indoors dressed in my favorite purple lace ensemble when the doorbell rang. Luckily I had my sweats on so I answered quickly. It was Mr Nelson. Could he borrow my Dad's woodsaw? I didn't see why not, I knew where the tools were kept so I beckoned him in. Of course I got the thrill of knowing what I was wearing underneath while he was standing there but I was well covered up so there was no risk.

He followed me out to the back room and I rooted around for the saw. It was right at the back of the bottom cupboard. As I got up from grabbing it, the edge of my sweat pants snagged and as I stood up the pants were pulled part way down, exposing one suspender strap and the top of my stockings. Of course he had to be staring straight at me at the time.

You know when time stops dead still? That's what happened. A second of so pause before I grabbed at the material and pulled the pants up. The damage was done though. My face reddened and I looked at the man in front of me hoping beyond hope he hadn't seen anything. But he had.

Not only that, he was smiling. A small smile at first opening up into a wider grin. "What do have we there?" he almost laughed.

"I'm sorry," I stammered, not sure what to say next. "Here, take your saw." "Please."

He walked back into the living room without answering and I skipped after him holding the saw. He stopped abruptly and turned and I almost ran into him, before I stepped a pace back. Even in full panic mode a curious thing caught my eye. A bulge in his trousers. And it was ever so slightly growing.

Time was momentarily still again. I knew then I had a choice. If I yelled at him to get out, made a massive scene perhaps he would go. I couldn't make him leave, he was a much bigger man than me, but if I acted now perhaps I could contain this. Some how, some way.

Every fibre in my cowardly being said run away. Get rid of him and deal with the consequences later. Go hide in a corner, cry, figure out a plan, pray to God you'll get away with it.

I didn't move. Something deep in my soul, I don't know what to this day, resisted. I could see the bulge growing, in fact I couldn't take my eyes off it. The voice in my head was screaming 'run' but still I stood there. This was my moment of destiny. A life defining decision. There was no doubt about it, no mistake, I was making that bulge grow.

Me.

So for the first time in my life I took a deep breath and a leap of faith. With the voice still screaming in my skull I pulled my top over my head and threw it on the floor. Then pulled down my pants and kicked them away. I stood before him in all my lingeried glory. And the bulge got even bigger.

He hadn't moved a muscle which I took as a good sign. So, with a slight wobble, I walked up to him. I could feel his breathing was heightened and see his eyes were bright and sharp. There was something else in his eyes too, something I now recognise as lust but didn't know it at the time. I stood in front of him and stared into his eyes. Still he didn't move. Taking courage I took his belt buckle in my hand. He didn't resist. I undid the clasp, pulling them down. His cock was still constrained within his pants but only just. I slid down and knelt submissively before him and pulled the briefs and the pants fully to the floor. His cock sprang out immediately and it was the most beautiful thing I'd ever seen.

Now watching porn you'll see a lot of cock. However Mr Nelson's rod was something else. About 7 and a half inches long, thick with it and the most perfect cut head. In all those years of online porn I had never seen a better example. And it was currently standing beyond the horizontal and six inches from my face.

I knew what to do, practising on the dildo had helped. Plus I'd seen it a thousand times on the screen. Without using my hands I moved my mouth over him and started to suck and lick. The texture of his cock was incredible and while I could only take so much in I did my best to give a professional blow job. I never took my eyes off his face, locking into his eyes, starting to recognise the lust.

Now sucking a cock is great for both parties as my slobbering and his twitching can testify. But let's be honest it's not what the thing is designed for. It wasn't long before I yearned for him to be inside me and surmised he felt the same. I let his thick stick go and just said 'lube' as I ran to my room. When I returned he was still standing but had divested himself of his clothes. I stopped short. This was it. A man in front of me with a raging hard on pointed straight at me. Finally I was going to get fucked. My heart skipped a beat.

He took the lube and motioned me to get on all fours. I complied and he pulled my panties down to my thighs before rubbing a generous amount of the cool liquid against my opening. My own tiny dick was hard and pointing downwards as he inserted one finger in me. Then two. He'd done this before. The feeling was intense.

I knew what was coming, that initial pain as the bulbous head pushes past my sphincter and then a delirious pleasure. I'd felt it many times before, but this time was oh so different. When he pushed into me my life changed in that instant. I knew as his first thrust gave me that sharp pain and I arched my back that things would never be the same again.

He took it slowly at first, I think he knew I wasn't used to his size. But after a few strokes he started a slow and steady rhythm. Pushing all the way in and withdrawing all but the tip. I grunted in time with his thrusts at first but the pain soon subsided and pleasure took over along with that wonderful feeling of being full. Quickly the grunts turned to girly moans. I knew then that with every stroke, as he filled me deeply to the hilt, that he was slowly fucking my masculinity away. With each thrust I was becoming a woman. With each moan I was becoming his. He was owning me and I was happy to let it be so.

Twenty magical minutes of being taken by him followed. After being hammered on all fours I sat astride him and rode his weapon as our hands entwined, him helping me to push up and plunge down so I was fully impaled. Twenty minutes of incomparable passion and desire. However my fantasies nearly always had the same ending and that's where we came in. With me on my back, legs draped over his shoulders watching him jackhammering me. Over and over. I had never experienced anything like this pleasure, this wanton need, this deep longing in my soul and I wished the moment could have lasted forever but he was moving fast towards his climax.

I had one more grab from my fantasy to come. I lock eyes with him as his pumping gets faster and deeper. "Fuck me daddy," I moan. His pace and power increases. "Fuck me," I implore. I know he is close. "Fuck me," I say softly.

"Fill me up."

"Make me pregnant daddy".

He comes with his deepest thrust and a guttural grunt. Flooding me with thousands upon thousands of sperm. I arch my back as I feel him shoot five, six, seven times, a cascade of warm sticky cum coating me deep inside and finishing my transition to womanhood.

We are spent. He pulls out of me and gets up to try to find a towel. I stay where I am. My boy-clit is throbbing but it will have to wait for attention until he has gone and I can relive the whole thing. Finally I rise up and immediately feel his seed start to trickle down the inside of my leg on to the stocking top. My legs buckle with joy. Realisation hits me. In the space of less than an hour I have seduced this man, sucked his cock, had my brains fucked out and absorbed his milk.

Say what you want about fantasies, the real thing is a million times better.

He returns. As he takes a swig from the beer he's taken from the fridge he stands and surveys me. "You know... this is only the beginning," he says.

My heart flutters and I know he is right. I am his now and he will use me as he wants. I will do anything for him, anywhere, anytime. And I cannot wait to start. But that's another story...