Fantasy to Reality Pt. 02

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The continuation of my story of fantasies becoming reality.
3.6k words
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Part 2 of the 2 part series

Updated 06/09/2023
Created 04/11/2020
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So what would you do next, dressed in your finest lingerie, standing facing the man who has taken you to places you only ever imagined, with his cum leaking from your ass and sliding down the inside of your leg?

Well it's a bit late for small talk so I guess he's just going to up and leave. I'm wrong. Instead he asks when my folks will be home. Another couple of hours I reply and he looks me up and down and says "What else do you have?"

I run to my room, careful to avoid dripping his cum on the carpet. My heart is pumping. What to choose? I have plenty of outfits but my mind is in a spin. It has to be black, slutty black. Speed is of the essence though, I need something I can put on quickly. My searching eyes stop on my crotchless fishnet bodystocking. The very thing. I rarely wear it but this seems the ideal moment.

Needless to say he fucked my brains out with me in it before the hour was out. I couldn't believe he could get so hard again so quickly. This time was equally divine, and he had no problem entering my well lubricated hole so I was immediately moaning like a girl. We didn't change the proven formula - he took me from behind first, then again with me frantically bouncing up and down on his rod and finally on my back when he plunged into me for the last time and fully seeded me. I remember thinking at that moment how everything felt so right, so perfect.

He did leave after that, taking the woodsaw with him. As for me, well the next few days went by in a blur. I didn't know what to do. Should I go and knock on his door, or find out his phone number, or lie in wait for him while he out? Or was that it? Did he just use me for a day? Was he laughing at me? Would he keep my secret?

Of course I wanked myself off at every opportunity, re-living the afternoon in as much detail as I could. The dildo has lost its magical appeal however, the real thing was so much better and I yearned for the next time, if ever there was to be one. As the week went by I was distracted at work, my mind wandering to think of him with increasing frequency. I couldn't concentrate, and my emotions ran wild.

Four days and nothing. I was convinced that was it, just a torrid one night stand. Then on the Thursday evening the doorbell rang. It was him. My father answered. He was returning the woodsaw and he also had a package addressed to me that had apparently been left in his porch by mistake. I ran down the stairs just my father closed the door and snatched the box from him. I leaped back up those stairs as fast as I ever had.

Once the door closed I ripped open the parcel. Inside were four more boxes, along with a handwritten note which I immediately grabbed.

"I know your parents are away this weekend. If you like what you see here, let yourself into my house on Saturday afternoon. Make use of these gifts and be ready in the master bedroom at 7pm."

I swear you could hear my heart pounding a mile away.

One by one I opened the boxes, starting with the largest. It contained the most exquisite set of red lingerie: an embroidered half cup lace bra, matching garter skirt and stockings, open backed lace panties and a delicate lace baby doll tied by a large bow at the front. I almost came there and then.

The second box yielded a make up kit containing mascara, foundation and lipstick along with brushes and several sets of false eyelashes.

The third contained an expensive-looking hair removal cream dispenser. In the final box was a key.

I melted. The next 48 hours would be the slowest of my life. I looked online for make-up tutorials and learned the basics quickly, tried on the lingerie over and over (it fitted perfectly), memorized the instructions on the dispenser and endlessly turned the key in my hand. I could hardly sleep, hardly think of anything else. Slowly the hours crept by.

At just before 6pm on Saturday evening I left the house clutching an overnight bag, and, as unobtrusively as possible, walked over to Mr Nelson's front door. After successfully unlocking it I walked in and stood alone, spine tingling, in the hallway of his property.

The house was spacious, a fine sized open plan living area dominated by a large fireplace. Leather couches, well chosen furnishings and deep pile carpets gave the the place a sense of sophistication without being ostentatious. The kitchen had high quality fittings, the bathrooms plenty of marble and chrome.

I made my way up to the large master bedroom. The room was sumptuous. Oak panelled wardrobes, heavy drapes and plush bedlinen. As I surveyed the room my eyes alighted on a small box, about 8 inches square, sitting in the centre of the bed. Beside it was a note which read "Do not open"

I was sorely tempted but I picked it up and put it on the nightstand. Then I got down to business, taking my time in dressing, feeling the delicate stocking fabric as I pulled it over my shaved legs, attaching the suspender straps with great care and donning the panties and baby doll, luxuriating in their feel against my skin. Entering the en-suite I applied my make up, arranged my shoulder length hair and checked my attire in the mirror one last time. I looked pretty hot it had to be said. I exited, dimmed the lights, closed the bedroom door and laid back on the bed, ready, willing and frankly a nervous wreck.

About ten past seven I heard a key in the door downstairs. I tensed and my heart rate went through the roof as I listened to the footsteps as he came slowly up the stairs.

The doorknob turned and there he was in front of me. I had forgotten what a handsome figure he cut. I heard him gasp and walk forward into the room. He was already excited, I could see that tell-tale bulge again. He stopped at the foot of the bed, towering over me.

I rose up and slowly crawled forward on all fours until I was in front of him. This time we were not in so much of a hurry so I was going to try to take my time. I sat up onto my knees and looked deep into his eyes. No words were exchanged, I just started undressing him. Slowly unbuttoning his shirt first and letting it slide off his shoulders. Then unbuckling his pants and letting them fall to the ground. His thick cock once again strained at his briefs. I pulled them down and it sprung out. I marveled again at just how wonderful it was. Slowly I leaned forward to take it into my mouth. I licked the shaft, kissed the head and sucked as if my life depended on it. All the while my eyes were glued to his face, searching for evidence of the pleasure I was giving him.

It was clear I was turning him on so much he wasn't going to hold out for very long. I knew I needed him inside me again, to feel him completely fill me. I let his glorious erection fall from my lips and moved back on the bed, laying on my back and moving my legs one to each side. In the finest lingerie money could buy I was spreading myself for him. I grabbed the lube I had ready and squirted a generous amount of the cool liquid at my entrance. My eyes beckoned him in. He needed no further invitation. Stepping out of his pants and briefs, ripping off his shoes and socks, this strong, virile man climbed on to the bed with his huge dick pointed straight out, harder than a rock. He stood over me and pulled at the bow at the front of my baby doll. He was unwrapping me.

Thereafter passed the most glorious fifteen minutes of my life. If he had taken me to heaven a week before, we went twice as high this time. The mixture of his deep, long strokes, his smell, the hardness and heat of his cock, the feeling of the suspender straps straining, the lace rubbing against me with every thrust. Nirvana. I urged him on, imploring him to "Fuck me" whenever I could catch my breath between my deep moans. I soon sensed he was close to coming, his pumping increasing. And then he did something completely unexpected. As he plunged into me, he leaned forward moving his face toward mine, and kissed me.

A bolt of electricity the like of which I had never experienced before or known since ripped through me. My life immediately made complete sense. I passionately kissed him back as he continued to pump me relentlessly. I arched my back as our tongues entwined and within a few moments he buried himself to the hilt and started to fire his hot sperm into me.

We continued with our kiss as he fully emptied himself into my waiting hole. I could feel his cock pulsing inside me, thick cum coating my insides. I was practically delirious with joy. As he started to soften he pulled away from the kiss and withdrew his cock, leaving me with an awful, empty feeling. He reached over to the nightstand and grabbed the box that I had placed there. Opening it revealed a beautiful glass butt plug which twinkled softly in the room's dim light. Looking me direct in the eyes he reached down and pushed it into my gaping hole - well, his hole now - and it sank perfectly into place. His cum was trapped inside me and I moaned with pleasure at the thought.

Laying on those opulent sheets, the scent of sex and sweat in the air, I knew I had found my place. That night we talked and talked. He told me all about himself: his work in the city; his upbringing; his failed marriage; how he'd found himself watching me even though he had never before entertained thoughts of being with another man. In turn I told him of my life, my delight in discovering lingerie, all my fantasies and desires. Hours later with his big arms wrapping me up, we fell into an exhausted sleep.

The next morning, with my plug still firmly in place, I gently woke him by sucking his cock. It was hard within no time at all and soon after I took his milk into my belly for the first time. As I felt the warm cum splashing in my mouth and sliding down my throat and chin, I savoured the taste of him, slowly licking my lips afterwards to get every drop. Half an hour later he replaced the plug with his cock and fucked me forcefully until he again blew his load deep in my loins.

After we had showered I spent the rest of the day as some sort of domestic goddess, cleaning the house, washing the dishes, hoovering the floor. I did it all dressed in black lace lingerie, one of my favourite outfits that I had brought along in my bag just in case. I even prepared him a succulent dinner that afternoon. Amazingly everything felt so natural, so comfortable, as if I had being doing this for years.

I knew I had to leave him before my parents returned but there was time for one more fabulous fucking, his magnificent cock spearing me for the third time that day, taking me to the same heights I had experienced before.

Thereafter we concocted many ways to be together. Weekends were straightforward enough if my parents were away, and during the week I would pretend to go for a walk but detour to his front door, or he would openly ask for me to help him with a 'project' he was doing in the yard. I imagine some of my other neighbours may have seen an odd pattern of behaviour if they were looking but everyone seemed oblivious.

Several months went by and summer turned to late fall. We settled into a steady pattern and the thrill and excitement of being taken by him never diminished. If anything the pleasure levels increased with the intimacy. We experimented with positions, tried every room of the house, the only constant was me taking his delicious cum deep into one of my willing holes at the end of every session.

And it was over the course of those weeks I gradually decided on a course of action that was to truly change my life.

After much deliberation I decided I wanted to fully become a woman. I wanted to look like one, feel like one, think like one. Perhaps deep down I had always these desires, perhaps it was due to my recent experiences, most likely a mixture of both. All I knew is that I wanted to live my life as a woman from now on.

I really didn't know how to broach the subject with Mr Nelson, or Mike as you should now know him. However in the same way as I had taken that initial leap of faith in my own living room, I knew I had to do the same again. So one day, as his cum was drying on my lips, I plucked up the courage and told him everything.

I guess I sort of knew what his reaction would be before I had finished talking. That tell-tale lust flashed in his eyes and his cock started to grow. He wouldn't make a good poker player.

To cut a story short I started on estrogen soon after and began the process of transition. Even though I had confronted my fears several times already, confessing to my parents was without doubt the hardest thing I had ever done. My destiny was decided though and they tried to support me as best they knew while never fully understanding.

I moved into Mike's house soon after. The desire and excitement never waned. He smuggled me into his work one day and took me roughly in the boardroom. It didn't have as many full lengths windows as I would have liked, but the thrill of standing there in stockings and suspenders as he, fully clothed, fucked my aching ass until it dripped with his semen was another ticked off chapter in my fantasy collection.

The hormones began to have an effect. My body shape started changing, breasts began to form, my hips enlarged. I felt different too, more emotional, a subtle change but clear to me. If it were possible I enjoyed my daily fucking with more intensity and heightened pleasure. The feelings lasted longer as well. My boy-clit was just a useless appendage. My primary reason to exist seemed to be to service the cock presented to me and to seek delight and joy from teasing out the precious cum contained within it.

The final part of my story took place on a day which started like many others: a long deep fucking before he went to work. This time however as my man went to leave he told me he had a surprise for me that evening. I was to go to our bedroom at 6pm and await instructions. My level of excitement knew no bounds.

Winter was pretty much upon us by then so I spent the day completing my daily chores dressed in my pink negligee and matching stockings and suspenders. The knot of anticipation in my stomach grew larger every hour until the clock struck 6.

I went to the bedroom. My phone buzzed and there was a text. "Close and lock the door," it said "and slide the key back under." I did as instructed and the phone buzzed again. "There is a package in the closet. Open it. Prepare yourself then wait for me to return."

The phone fell silent. I rushed to the closet and rummaged around for the package. It was a large, white, heavy box, expensive-looking with a large bow on the front. With shaking hands I pulled open the bow and opened the lid.

Contained within was the most stunning array of white lingerie I had ever seen. The finest, most delicate lace, the creamiest softest chiffon, the most elegant, sensual design. There was a quarter cup bra, matching garter belt with suspenders, a backless pair of panties, 4 inch stilettos, a see through chemise, light satin robe and finally a flowing lace veil. I sat back on my heels. It was just spectacular.

I knew what I had to do. I showered and shaved myself, even though I had already done so that morning. I took time to arrange my hair, re-apply my make-up and fix my eyelashes. As I finished and prepared to dress I heard movement downstairs.

Putting on this beautiful clothing took some time as I enjoyed the feel of the material on my body. The sheerness of the stockings, the tension of the suspenders straps, the chiffon and lace touching my body as I moved. The veil cascading down my back, the robe swishing in the air.

I was ready and I waited. I waited half an hour, the nervousness increasing every minute until I heard his footsteps on the stairs and him pick up the key, turn the lock and push open the door. I stood before him as his bride.

He looked magnificent, dressed in a smart suit and looking more stylish and athletic than I had ever seen him. His eyes widened when he saw me and his mouth creased into a smile. He walked over to me, kissed me deeply on the lips, took my hand and led me out of the room and down the stairs.

The sight that greeted me took my breath away. Candles glinted everywhere and the big open fire was roaring. It was the first time I had seen it in use. He continued to lead me until we were in front of the marble fireplace. There he pushed me down onto the sheepskin rug until I was on my knees. My greatest fantasy was coming true at last. As the logs crackled and the shadows danced on the walls and ceiling, I opened his belt, pulled his pants and briefs down and prepared to give him the blowjob of my life.

He tasted so good. I sucked and licked his cock, driving him into a frenzy. His cock was as thick and long as I had ever seen it. I bobbed up and down on him, cramming as much of his meat down my throat as I could. I would have happily continued for hours with the fire warming my heart and my soul.

He had other ideas though and soon he was naked. Within a few moments I was on all fours as he entered me from behind. I arched my back and moaned as he thrust deeply into me. I stared into the fire, lost in ecstasy as he continued to ravage me, my knees and elbows rubbed almost raw. He was taking his time, strong and steady, bringing me slowly up to the point of total abandonment. Just when I thought it could not get any better he withdrew and pushed me gently on to my back where I could stare up at him. We locked eyes as he recommenced his slow and deep fucking of me, ploughing me to the depths of my very being. He leaned in to kiss me and I wrapped my arms and legs around him, the feel of the lingerie straining against my skin pushing me almost over the edge.

He pulled his head back and sat back on on his heels, holding my legs wide, and started to pump me quicker. He looked at me, his eyes boring into mine and breathlessly said "You... belong... to... me."

"I am yours daddy'" I said softly, "Daddy I am yours forever."

At that second he pulled out, his cock throbbed and I watched as he shot ropes and ropes of precious cum over my body. He was marking me as his. His hot creamy seed splattered over the delicate fabric and I gave a loud involuntary yelp as it hit me. It seemed to gush forever and if I could bottle one moment and keep it with my for all time it would be that moment. As the stream of semen subsided I took up a glob from my chest with my finger and brought it to my mouth before sucking it down into me.

"Forever," I said.

Epilogue

We moved further out from the city a while later, it just seemed the right thing to do. Over time I completed my transition to a woman, giving my man some breasts to fondle and an extra hole to fill with his cum. Everything about the experience and about being a woman was better than I ever imagined it would be.

Fast forward and I am laying over a fallen tree in the woods behind our new home. The cock I worship is plunging into me from behind and my lingerie is rubbing against the bark and the leaves on the ground. My eyes are closed as I experience another of my collection of fantasies coming true. Then I gasp and open my eyes as I sense him reaching his peak. As he thrusts deeply and floods me again with his thick, warm, salty cum, realisation dawns on me.

There was no collection of fantasies after all. Instead there was only one gigantic fantasy. And I am living that fantasy as reality every single day of my life...

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2 Comments
Riki1942Riki1942over 1 year ago

You are definitely right about a real cock feeling nothing like a dildo. It's not just how it feels either, It's a real sperm squirting cock attached to a real man.

I wouldn't want to have a sex change operation because that would make it too much like being a real woman and I love gay sex as a crossdressing sissy.

If I were young enough for it to change my body to that of a pretty girl, I would definitely go on hormones, get breast implants if I needed them and become a shemale. I would still want to have my cock and balls so that I could still feel gay.

I can cum again, even after an orgasm and going soft, if I'm fucked long enough. As long as I could still cum from getting fucked, as long as I could have the body of a pretty girl, I wouldn't care if the hormones made me so I couldn't get hard and shrank my cock and balls. In fact, I think it would be sexy to have a feminine little cock and balls.

1sfshermale1sfshermaleabout 4 years ago
Ty

Thanks for the story....wonderful adventure and life

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