Amy's Saga

AMY'S SAGA

CHAPTER 1

I think I had always known it... Yes, I had known this incredibly powerful drive in me since as early as age four or five, but had not been able to understand its impact until way into adulthood. There are many factors, social, cultural, religious, etc., behind minimizing the importance of that drive. I had always been able to cover it somehow and deny it even to myself before others. The fact that I had fallen in love with women also helped overlook the veracity of the need to become a woman in the first place. After all, the prevailing wisdom in the society tells us sexual kind of love happens between opposite sexes. So, I must have been a true man!..

Denial can also be a very powerful drive... It can make us do things against our best interest, yet we would not be really cognizant of the consequences until it is too late. I too fell victim to that. I got married at a young age, into a life not conducive to my happiness...

Of course, it did not work!.. After a huge cataclysm with my wife, I started questioning many of the assumptions in my life. Needless to say, the biggest one of those assumptions has been the lie I've been telling myself about being a man, and a straight one for that matter.

After a long-standing struggle, I gave in to having sex with men and actually liked it, not much to my surprise. But even that was not too big of a breakthrough... As I had found after my illicit affairs with men, there were tons of guys out there who engaged in gay sex, many of them calling themselves straight, while even being married during the process.

About nine years ago, listening to my inner voice, and watching countless similar examples in the outside world, I finally realized that I had to do something to bring out the female in me. For years, I had been crossdressing at home when I was alone, even in my childhood (of course, in simple ways). But, now I was looking forward to seeing the daylight as a woman. So, I decided to give a try to one of those male-to-female transformation services whose ads I had been reading for ages, without having the balls to do anything about it. Interestingly, losing my balls for a second fuck-hole was also what I had been yearning for all along... :-)

====================================

In June 2011, the relationship with my wife was already at a point of complete break-up, so she had left me to live with her sister until the final step, divorce. On a Friday night, I went to meet this trans-woman called Sally, in Dallas. She was running a Male-to-Female Transformation service in an apartment complex near the airport, along with a female helper, a woman who looked in her late 50s. I was thinking that if the experience turned out horrendous, then I would have at least tried it.

After cleaning and shaving my whole body, I went to meet Sally. I had decided to wear something neither male, nor too female for obvious reasons: I couldn't be the first, as it denied the spirit of the exercise; while the second should have resulted from Sally's efforts, not mine.

So, when I met Sally, I was wearing a plain white t-shirt with gray leggings underneath, barefoot with flip-flops, exposing a silver anklet that I liked for its simple femininity.

As I was coming out of my car, Sally opened the door to her apartment in the basement, looked at me in appreciation, and said in her unmistakable, feminized male tone "You have a nice physique!" I guess that boosted my confidence, because I realized I had started swaggering ever so slightly and swaying my hips when I walked towards Sally... A good sign in mental transformation!

She took me inside and introduced me to her helper. As we sat down, the older woman also complimented me and said she liked my anklet. After a few minutes of chit-chat, we moved to the room inside to start my transformation.

Sally seemed really into what she was doing. She spent a good 60-70 minutes on me, putting makeup and transforming my face. Then, from among a variety of wigs, I picked a long wavy one that looked very feminine, without being over-the-top attention grabbing... It was auburn in color, also being close to my natural colors.

We then picked a dress that wasn't too short, so it covered my upper legs while exposing the knees and below. Since I was shaven clean all over, there was no problem exposing my legs.

Assuming I was one of the many transvestites who loved pantyhose, Sally recommended one matching my dress. But, I hate pantyhose, and there was no way I would wear one in 90-degrees Dallas weather in June. So, instead, she painted my toenails black and gave me one of her strappy sandals for the night.

Then, she took a good number of pictures and gave them to me. These have been some of my most prized possessions since that day. :-)

Finally, had come the pivotal moment of the night! Sally's transformation package included a girls-night-out to downtown Dallas. We would be going to a restaurant or a night club, spend an hour or two, then come back to her apartment to change back (to male clothes, if I wanted).

But, it was already past 10 pm, so on a Friday night, going to downtown and coming back would take too long. Therefore, instead, we went to a nearby Mexican restaurant for some late dinner.

Here it was, my moment of truth, to find what I was made of... i.e. what Amy was made of!..

====================================

As we got out of Sally's car and walked towards the restaurant in the dark of the night, I felt this strange but expected tingling in my stomach. Needless to say, I was also extremely wet between my legs, living beyond my wildest dreams of going out as a woman... and a fairly pretty one, I should say!

Climbing the few steps into the building, we came across a family leaving the restaurant. Suddenly, that started creating a lot of clichés in my mind. A good Christian family that just had dinner running across perverted shemales!..

I did not have the courage to look them in the eye, as if I had to... Then again, probably they did not even pay much attention to us anyway, in the dark! The problem was mostly in my mind, projecting my apprehension upon other people...

Anyway, we entered the restaurant and got seated at our table. Our waiter was a young guy in his twenties. He was very polite and professional. Even if he understood that two out of the three women at the table were not biological females, he showed no sign of it. We were all called "ladies" by him.

When I got used to the situation, I had also come to realize the surreality of it. There I was, in a regular restaurant, "en femme totale" as they say, and the whole thing continued flowing without any problem.

After my trepidation was over, I started looking around at the other guests. There was a young couple in the next table, and the girl was staring at me every now and then... For the first time in my life, a woman was staring at me intently like that, and what's more, when there was another guy next to her. Even if it was her curiosity more than anything else, that was an unusual thing for me, highlighting the extraordinariness of my situation.

At one point in the conversation, the three of us were talking about dating men. Then, Sally's older assistant turned to me and, in a slightly surprised tone, said "Oh, you also want to have sex with men? Well, that's very normal!"

You got that right, lady! It was normal... Even though some men say they like crossdressing while being 100% straight, I find that hard to swallow... I mean, seriously? While even the full "straightness" of upright men is a doubtful premise, why would anyone who enjoys wearing woman's clothes pretend to be fully straight?

In any case, we finished our dinner and started going back to Sally's nearby apartment. In the parking lot, Sally turned to me and said:

- Well, Amy, even if you had any nerves, you've shown none of it. Congratulations!

I asked her how I can meet men for dating, and yes, also for sex! She gave me some tips, but obviously not any names, because, as she put it, she did not want to be involved in "solicitation".

While I was leaving her apartment for the night, I had decided to keep my feminine appearance for the weekend. Sally said that was a good idea. She also invited me to a concert that her "all trans-girl band" would be giving the following night, on Saturday, in Denton, about 40 miles north of Dallas. She said I would meet new and interesting people. I said "sure"...

But, I did not go there, the next day. I chickened out and sat at home in my woman's clothes, makeup and nail-polish from the previous night... only to regret it later, to think about the people I could have met in that concert, as well as whether that could have changed my female life later on!..

CHAPTER 2

Fast forwarding for three years... It was June 2014, and I was already comfortably having sex with men, and with many of them, for that matter. However, I didn't see myself as an integral part of the sex. Something was terribly missing. I was meant to receive all these cocks not as a gay man who chose to be passive in bed, but as a woman that I had always felt I was...

I knew I was already happier living my daily life as a woman, doing routine things. The missing piece was how I would react to intimacy as a woman, i.e. the other vital part of human life... Hence, three years of experimentation with men had brought me to the conclusion that I needed to try having sex as a woman... and see if I was fooling myself about that very drastic desire of changing my gender, or not!

By that time, i.e. June 2014, I had become fairly proficient in transforming myself into a woman. As some people also affirmed after seeing my picture, I had been reasonably successful in turning into a passing woman, and an attractive one for that matter.

So, men must have liked what they saw in me. But, then again, that was the easier-to-please gender. Men are pathological seekers of sex, and most of them would love to fuck any skirt, or any hole that moved, so to speak!

But, would I also look appealing to a woman, as a woman? That was the bigger question I had to find an answer for...

Therefore, I put an ad into Craig's List, worded exactly as follows:

"I am a very passable TG, looking for a Male-Female couple to play with. My name is Amy, I am quite small in size, only 5'3'' and 125 lbs with a slender body. The picture is really mine (I have more that I can send later, if there is mutual interest). If you are serious in meeting with me, please send me a face picture for both of you, then we'll see where that leads us. I will reply to all serious inquiries. I am looking forward to meeting a hot couple this Saturday evening. "

Yes, I was turning into a sleazy temptress... and, I could not feel ashamed of that, no matter how hard I tried! ;-)

====================================

Well, my post had triggered some amount of interest from adventurous couples. Had I addressed single males, I am sure I would have been inundated with fuck requests. But, as you can guess, most of those would be coming from scary losers, so the sheer number of replies would not tell much by itself about my prospects to get laid as a woman!

From among the replies, one attracted my attention about a white man who said his wife was some sort of a minority. He had also sent a picture of two of them together. Although the picture was a little fuzzy, it provided some authenticity about his claim that they were looking for a third person for sex, preferably a trans-girl...

Anyway, by the time I received his response to my inquiry about who they were and when they wanted to meet, I was in my office late Friday afternoon, at the end of a work week. The guy invited me to their house; which I tentatively accepted, but said I had no time to get into my female persona... He said "Fine, come as you are, you can come as female the next time we meet". That was a fine answer, so I went there, a good 50-minute drive away from my work, as well as my house.

The guy was a white man, probably in his early 50s. He had a beard and a thick Texas accent! So, there I was with a perverted(!) Texan man among all the Bible-Belt folks!

His wife (not girlfriend, as they say they were married) was a cute 26 year-old black girl. So, this was already an unusual union. They both had kids from previous marriages. After their respective divorces, they had found each other on the Internet. So, how about that good old Net as a match-maker?

Apparently, they had a very open relationship where they would invite people to their house for collective sex! Their preference would be men with good stamina to fuck them both in one encounter. So, my male host was a bottom bisexual, if there is such a term...

Thus, it seemed like they were interested in me as a trans-girl who could use her native cock on both of them. That was quite an intriguing proposition for me, even though my main interest was to meet a couple where the man would be willing to fuck me, while the woman would be involved as sort of a lesbian in the mix.

But, the truth is one cannot tailor everything in life to his/her taste. The same had proven true in this case for me, even though the outcome was still quite fascinating!

====================================

It turned out my hosts had also invited another couple, a Hispanic man & woman in their 40s to 50s...

So, with me, that made three men and two women... or, two men and three women... depending upon how you look at it!

Well, you wouldn't believe at our gathering until you saw it. First, people sat down, talked and drank in a friendly and civilized manner for about an hour. I was thinking "Is that really it? It can't be!"

Then, it turned out that the Latina lady had never been with a woman before. Therefore, the young black girl was going to break her in, so to speak... In a short time, whatever little clothes people had on were taken off, and my black female host went down on the Latina woman right in front of us. I guess it was business as usual for most of them, but pretty surreal to me. All my sex encounters up to that moment were limited to just another person (male or female).

Then, the two women must have thought there was too much intrusion, so they went inside, and we gave them some privacy.

About 20 minutes later, the black girl returned. She must have decided for a change of air, so gave me one of the best blow-jobs of my life... She didn't cheat in any part of it, so once it was over, I felt like I wanted to eat her pussy, not only as a payback for suitable reciprocation, but more...

I had not gone down on a woman I hadn't known before, so that was a question mark for me. I was already settled for anything that didn't taste or smell badly.

To my surprise, as soon as I started, I realized she actually had a really peculiar and sweet taste. She was quite petite, not too pretty, but attractive in her own way. She was standing while I was eating her, so looking from down up, I saw a woman in a way I had never seen before.. and that was magical!

I saw some sparkling in her eyes, and at that moment, I realized they had blue or green undertones (there must have been some white ancestry in her lineage, even though her skin was still fairly dark).

And, you know what else I realized? You may be familiar with that bitchy tone that some black women use in their language, not in a bad or condescending way, but simply how they talk to people during their normal lives.

Well, that paint called "culture" had been removed right in front of my eyes during the very act of cunnilingus. She had become a malleable sweet girl, simply enjoying the sensations emanating from her sex organ.

You may have heard people telling each other "I love you!" during sex. You should never take that seriously! But, it was so easy for me to fall in love with that angelic expression caused by my own actions during those few magical moments...

Then, we stopped, and things returned to normal. Well, "normal" in that case meant any other kind of sex activities between three men and two women... and then, we really stopped for good.

====================================

At one point, my bearded host asked me to go with him to their bedroom inside, so that I can fuck him. See, in his mind, I was one of those sultry shemales who enjoyed fucking men in the ass. The problem is that people do not realize this is mostly an artifact of porn. Well, transsexual prostitutes may be doing it for the money; but, then again, for money, people do all sorts of things they normally don't do. I don't think any trans-girl in her right mind would want to fuck a man... even fucking a woman could be questionable, but definitely not a man. All that hassle to change into a woman is to be treated like a woman inside and outside the bedroom. So, why would I want to use my dick on anybody?

However, he was the host, so I yielded to his desire, and we moved to the bedroom. He immediately spread-eagled on the side of the bed, and offered his puckered hole to me. Despite my trepidation, I still attempted to put my cock in him.

But, lo and behold, no matter how hard I tried, it did not work! I was not getting hard before a scene that was not even a bit inviting to me. So, we gave up and returned to the living room where the other three were involved in carnal acts of their own!

I could justify not getting hard at the prospect of fucking a man, but I was still thinking I could nevertheless fuck a woman. After all, that's what I had been doing for years, i.e. until I lost interest in my wife, and found my true interest being in becoming passive in sex with men!

But, fucking a woman still sounded as an attractive endeavor... I thought I could even do that after transforming into a woman, i.e. especially if I don't go through a full sex reassignment surgery, therefore keep my cock on an otherwise completely female body.

So, I started looking at the two women available to be taken, in front of me. Sensing my intention, the host guy warned me about wearing a condom. Yeah, sure, I would do that, why not?

Then, I put on a condom, and tried to penetrate one of the women in the mix. But, I was still not getting hard enough... I tried entering the other woman... My dick was still resisting and defying my intentions.

I just could not get hard. It was not about fucking a woman or a man... I was being put face-to-face with a cold, but true fact: My body and more importantly my mind were rejecting the traditional male role I had been forcing myself to play since my adolescence. I just could not bring myself even to the state of excitation where I would be playing the role of the active man with a cock! Let alone reaching orgasm through fucking any hole...

====================================

That night had revealed one of the most sobering truths of my life. Whether it was real or just forced, my previous life of acting as a traditional male in sex was clearly and unequivocally over. I had been suspecting that for quite some time, but being presented with the cold truth had still been quite shocking to me!

The preceding three years of my life, where in all my sex encounters I had acted as a passive participant, were now standing as the undeniable reality. However, at the same time, I had become acutely aware of the fact that all those racy affairs that could have been written off as simple encounters of a bottom gay man were actually more than that... The female in me was trying to burst out, and did not want to get limited to sporadic moments of wearing women's dresses, then walking streets for fun!

This was not a hobby, and I was more than a simple crossdresser. As evidenced by my experience that night, my psyche was transforming into something that I had resisted for a very long time. My penis could no longer become hard to fuck anybody...