Amy's Saga

At the end of that night, my cute black female host turned to me, and as if saying something mundane like "The weather is so nice today," she whispered "You know, I can never truly cum in these parties, because I cannot concentrate with all those things happening around me."

I smiled at her. She was right for herself, but not for me... Although she must have thought she was addressing an adult man, she was actually talking to a woman just like herself. That woman could not have reached orgasm, because she had not been treated as a woman that night!

CHAPTER 3

So, I was determined to find out how my body and mind would react to having sex with a man, while I was in my practically "full female" mode. Therefore, I changed my strategy, and rather than looking for a male-female couple for sex, I decided to seek single men for it.

As anyone who has the slightest knowledge on how men approach sex could tell, I was inundated with responses from very articulate and seemingly sweet men on one end of the extreme, to straight up weirdos on the other...

Yes, I know this is the part where my common sense may get questioned the most. How could I entrust my body to an entirely unknown man, risk getting raped, without being able to do anything about it? After all, I was in someone else's turf, in a weak and small girly frame..

Well, I cannot really answer that question, because I don't know how to address the truth in it. To be frank, I knew I was taking a risk, albeit a calculated one. I could never be really sure that I wouldn't meet the next Jack the Ripper who could pass as a normal person in need of some kinky sex.

I guess I was still relying on my ability to distinguish good people from the bad ones, and trust on a higher power who could still forsake me despite my apparent transgression!

Anyway, I had started going through the replies, and decided on giving a try to one of them that looked promising... a young guy with a hot body. After much preparation, I drove to his place, only to realize that I had forgotten my purse at home with my driver's license in it. You can imagine the horror I felt after coming to the realization that I was in drag at night on downtown streets, with no identification whatsoever...

Trying to obey even the most minor traffic laws, so as not to get pulled over by a cop, I went back home and picked up my purse. The guy's house was about a half-hour drive from mine, so by the time I arrived there, I was about an hour late. He wasn't too happy about it, and had possibly already found a way to relieve himself. At least, it looked that way from his indifferent attitude after seeing me on his doorstep.

So, needless to say, I stayed there for five minutes, drank a glass of water, and headed back home. My first attempt to have sex with a man as a woman had ended in complete failure. But, a voice in me was telling that this was for the better. I would see very soon whether this was true or not!

CHAPTER 4

So, the next few days passed with better preparation to meet my first man for sex while being a full woman. After some further deliberation, I found a new candidate. He was a middle-aged black guy with somewhat lighter skin. He seemed quite nice and polite. Not to forget big and handsome!..

He seemed very interested in me like most other guys who replied to my post, but his interest also seemed a little more genuine than the others. He offered to take me out to dinner first. Although I would have loved the idea of spending the night as a woman with a man as most couples would do before any intimacy, I was also scared about how well I would fare in public.

Sensing my hesitation, he proposed to meet at a Starbucks instead of a full-fledged restaurant. Now, as you can see, all these are good signs, because someone who wanted to hurt me would directly invite me to a private place. So, although I was apprehensive about meeting with him in public because I could get "read" by others, I was also happy he was insisting on it, somehow displaying his good will about the whole encounter.

But, my preparation took forever, as I had wanted to look my best. At that moment, I sort of had a grasp on why women are known to take so long to get ready before going out the door. You may not fully agree with that drive, but I think I might be a rather stereotypical female in that regard... ;-)

So, I wrote to him to say my preparation was taking long, and asked if he could tolerate that. I had also mentioned some of my previous encounters with flaky men. He responded with an emphatic "No way I am going to stand you!"

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By that time, I had already become proficient in transforming myself into a fairly passable woman. Starting by shaving my entire body to be sure no trace of hair was left, I continued by working on my face. Concealing the shadow of a beard can be a problem, and I had an especially strong beard. So, I repeated what Sally had taught me, i.e. applying a lot of lipstick to my entire face. Then, I rubbed it until it created a thick enough layer over my skin such that beard shadow wouldn't be visible anymore.

Next in line was to put on my wig, and move it around slightly, until it sits naturally over my head. When I go out, I usually choose low-key wigs, because overly attractive hair... well, attracts too much attention. Other than its style, I also make sure the wig's color matches my normal hair, eyebrows, eyelashes, etc. That would mean dark brown or auburn for me...

Once the wig was in its place, I proceeded to apply make-up, which created sort of a second layer, then I applied eye makeup and finally lipstick. To match the mood of the occasion, as well as my slutty disposition, I chose a red lipstick, the same bright red color in which I had already painted the nails on my fingers and toes.

As for my outfit, I had already decided on a light colored summer dress with a flowery design. Although I would have really liked to wear a strapless dress or at least one with narrow straps, I couldn't do that because of the critical function my bra was fulfilling. I had 34C prosthetic breasts integrated into my body with

medical-grade glue; but there was no guarantee they would stay in place, so wearing a bra with strong straps was a requirement in that case. Therefore, a strapless dress was out of the question, as it would expose unsightly straps!

Finally, I slipped into a pair of strapless three-inch sandals that matched the color of my dress. My red toes were peeking at me in all their brightness, reminding me that my feminine transformation was complete!

Oh, of course, not to forget appropriate jewelry, i.e. earrings, bracelets, a necklace and my favorite silver anklet, all complementing my overall appearance, without being ostentatious!

Replenishing the lost effect of my favorite perfume during the entire transformation, and finally picking a handbag, I was all set to hit the road around 10.30 pm. In complete dark, heading to the house of an unknown man, I was ready to claim my femininity, or see it get shattered and disappear into ether, depending on how things would progress through that night!

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After driving about 45 minutes, I arrived at his neighborhood. The time was nearing 11.30 pm, almost midnight. It looked a fine neighborhood, clean and orderly, but not very rich, probably upper middle class... I circled around carefully while looking for his street number, not to raise attention from anyone. But, I could not see any signs of life, except a few dim lights emanating from a few houses.

Finally, I found his house. I parked my car on a side street and got out. Slowly, but decidedly, I started walking towards his door. I could feel an ever so faint summer breeze tingling on my naked shoulders and bare legs. The little noise made by my high heels on the sidewalk reminded me of similar noises made by hookers in movies. Rather than making me feel scared or ashamed, that realization somehow strengthened my resolve to go through that door. I was no different than a hooker, going to a man's house in a skimpy outfit for nothing more than cheap sex. The only exception was that he would not pay me, because I was not doing this for money. I was doing it to prove to myself that I could finally have sex with a man as a woman; therefore, that last step in convincing myself that I was actually female, not male, would be taken!

I reached the door and was looking at it in disbelief! If I knocked it, my life could turn different forever. I could have also given up at the last second, run back to the safety of my home, without him ever knowing that I had stood at his doorstep. Probably, he would think I was one of the countless flakes looking for sex on the Internet, and he would forget all about it the next day... while I would continue to struggle forever in unfulfilled fantasies of womanhood.

But, I was not the one to live with unfulfilled dreams anymore. I had the resolve to struggle through real relationships, not dry fantasies! So, I knocked on the door... Not just once, but for a few times to signify my intent... more to myself than to him!

After only a few moments, the door opened. There he was, standing and checking me out with curious, but also clearly very lewd eyes.

— Thanks for coming, he said softly, I am Michael!

— Hi, I am Amy!

I couldn't believe how my voice had come out. It was definitely not something I had heard from myself before. It was something else... Softer, differently determined, unmistakably feminine!

Michael held me from my shoulders and pulled me inside. As soon as I heard the door closing behind me, his face was only inches away from mine.

He hugged me, and I almost instantly felt his lips on mine. My bag fell off my shoulders... As his hands were traveling down my back to my hips, I realized the reality of the moment. Everything I had fantasized for years and years were becoming a reality right in front of my eyes, and I was the protagonist in it. All my expectations for some quiet, romantic moments before the sex vanished very quickly from my mind.

His tongue was thicker than anyone I had kissed before, moving very rapidly in my mouth. There was no reason to resist anything anymore... I started kissing him back, wrapping my arms around his neck.

Even on my three-inch heels, I was still much shorter than him. Reveling in my petite 5'3'' size, I rose slightly on my toes to hug him at his 6'2'' frame. I felt years of yearning flow out of my body, getting replaced by feminine desire. It was working, my metamorphosis was starting!

I felt his hand lifting my skirt and finding its way through my skimpy panties, into my crack. Michael was losing no time in arriving at his target destination. He whispered:

— Seeing your picture online, I dreamed of this...

So had I, but things were happening a little too fast... I was looking for a place to lie down. He sensed that, and pulled me slowly to a dark room behind him. On the side, I could see his living room under a dim light; something jazzy was playing in the background, while I was being dragged into a bedroom... for sex!

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Michael led me onto a bed in what was a small and very dark bedroom. After a few more seconds of passionate kissing, his hand was back at my crack. As for me, under the spell of that moment expected throughout a lifetime, I was about the drop my last inhibitions. So, I moved my hand over to the front of his shorts, and immediately felt the unmistakable hardness underneath it.

With Michael's hand probing what would be my vagina for the night, I was stroking his manhood under the fabric of his shorts. My female transformation was getting the better of my judgment, because before I knew it, I pulled his shorts down for an unrestricted access to my prize.

His cock was incredibly big, pulsating under my small girly hand. As I stroked it, Michael started kissing me even more fiercely. His finger in my crack had also intensified his invasion, so I realized I had to do something before things went down even faster and out of control.

I told him I wanted to change into something more comfortable. This was true, and not just an excuse to slow him down, as I was thinking the purpose of my first dress was to sit down with him and chat for a while until things would warm up. But, apparently, we had zoomed through that initial stage in just seconds.

So, despite all his lusty fervor, Michael had been able to pull himself together and, as a good host, showed me the way to his bathroom. Once inside, I took my dress off, adjusted my wig and the prosthetic breasts, and freshened my makeup. Then, I wore a lace teddy that I had bought for such an occasion. Finally, with my high-heeled sandals still on, I was ready for a night of intimacy!..

All this took about ten minutes, during which I could sense Michael's impatience growing, as he strolled outside the bathroom door. He asked once if I was OK, and I affirmed it. When I finally left the bathroom, he looked at me, and very clearly liked what he saw. As for me, I had enjoyed his reaction, as I had already started developing a strong appreciation towards the kind of interest a man could have towards a woman.

A side-effect of all this work had been a terrible thirst, which was not helped by the warm temperature in his house. I asked him for a glass of water, which seemed like an extra whim after making him wait outside the bathroom door for so long!

He showed me the way to the kitchen. While I was walking in my lace teddy and strutting over my high-heels towards the fridge, I knew Michael was coming behind me and watching my back and ass the whole time.

As soon as I emptied the glass, Michael's hands were all over me again, and I knew they would be there until the end of the night. In order to pacify his excitement, and also to do something I have been wanting for a while, I dropped on my knees on the kitchen floor, pulled down his shorts again and took the entire length of his cock into my mouth. Michael's hands moved onto my hair, grabbing my head strongly from both sides. I had sucked many men before, but his cock was possibly the biggest one I had seen... and, that had coincided with my female inauguration night!.. ;-)

That moment was different than all other times I had sucked a cock before... That night, I was feeling incredibly feminine, in those clothes, sandals, jewelry and makeup that had taken me hours to perfect... I was loving the whole experience, even before the main event had started!

Although all men love getting blown, Michael apparently was more interested in a different kind of action. He led me back to the bedroom we were already in, and, without turning the light on, placed me on the side of the bed on all fours. I could already feel the tip of his cock at the entrance of my crack, but this position was not the best to start a good ass-fuck!

Lo and behold, he was unable to put his cock into me and getting a little frustrated. Thinking we could both get some visual benefit from light, I asked him to turn the lights on. He refused, and continued his efforts to no avail...

I suggested lying on my back, which is always a better position, at least for me, to get fucked. He had to agree, as he could go nowhere in his favorite doggie position...

As soon as I lied on my back, Michael was all over me again. I could see his face in the dark and feel the weight of his big body over mine, which was a little unexpected to handle for me. The penetration was better, and I could feel him gaining about half an inch or so every time he pushed his cock into me.

But, the pressure added by my wig, bra and teddy, on top of his great body weight, was making me increasingly breathless. At some point, I started feeling like I was about to suffocate, while Michael, unaware of it, was still pushing his way into my body.

I told him in a distressed voice that I needed some breath and couldn't enjoy what was happening at that moment. Perhaps thinking I was playing hard, Michael whispered to keep quiet and take it.

At that very moment, I sensed I could understand how people felt getting raped. Fear covered all over my body, as I had no chance to get out of that utterly vulnerable position, in the house and bed of a man much stronger than me, forcing his body into mine...

Still mostly breathless, but my mind rushing through thoughts to get me out of that position, I said:

— Michael, I can't breathe. I can't have sex like this!

This time, my pleading had worked and the man over me lifted his weight a little to give me some room. I slid from under him, took my teddy and sandals off and adjusted my wig not to cover my face while lying down.

With only my wig on my head, and my bra covering the prosthetic breasts, I lied down again. Being freed from most obstacles, I was now naked and free to enjoy sex with my man!

I think he had also sensed my relaxation, so he pulled out of his earlier aggressive behavior that ended up almost raping me.

Michael was still aggressive, but now in a more loving manner. Furthermore, being able to breathe and cool off, I too had become a willing partner. I raised my legs over his broad shoulders, and moved my hips forward. Michael responded by pushing his cock deeper into my body. Now that I really wanted to get fucked, my sphincter muscle was relaxing, while his enormous manhood penetrated into depths that I never knew existed in my body.

Before long, I heard a slapping sound. Michael looked at me in the dark and whispered:

— My balls are slapping against your ass cheeks. I'm inside you all the way, baby!

Then, he added with a victorious smile:

— I'm gonna fuck you good and hard, girl! Now, you cannot escape...

I whispered back in my newly found female voice:

— Who wants to escape? Just fuck me!

And he did... Every time he pulled out, my body was moving towards him as if to beg not to empty my body. Then, as he pumped back into my hole, I was losing all sense of time and space, out of pleasure...

Michael was now pumping at an incredible speed, and I was having trouble meeting his pace. That was the difference between a big, muscular, virile man controlling the entire fucking and a little helpless female, doing nothing more than just lying there, providing a wet dark hole to deserving manhood!

But, being female, I was incredibly enjoying the assault my hole had started receiving. I began moaning uncontrollably, and soon my screams filled the entire house.

Knowing he now owned my hole, Michael turned me over, so he can put me on all fours again. This position, which had proved impossible about a half hour ago when we just started fucking, now became so easy.

As soon as I was on my hands and knees, Michael pushed his giant cock into my asshole, and started fucking me with a torrid pace. I felt like my ass was being split in two, but I was also enjoying it like hell.

Once my eyes got used to the darkness, I could see more than before, but would still like more visual input. So, I asked Michael to turn on the light, and he agreed this time. As he moved away momentarily, his cock popped out of my asshole, and I felt a big void and coldness in the hot room...

As the light filled the room, I raised my head and looked into the mirror next to our bed. I saw a naked brunette looking at me, her hair a little messed up, but makeup mostly in place. Her voluptuous breasts were looking inviting inside the black bra that was the only piece of clothing on her body. Her hairless shiny ass was raised in the air, waiting for her man to split it into two again, and fuck it as if there was no tomorrow.

Realizing that naked brunette who got fucked savagely and waiting on her hands and knees to get fucked even more was me had been an incredible sensation.