Tags: Transgender, Gay, Bisexual, Sissy, Authoritarian
"Once I break you to suck and bend over for me, there is no turning back. Think about it."
The problem at hand right now is that I can't stop thinking about it since getting that email. And the reason I can't stop kicking around the idea of accepting his offer is because I find the thought of being owned and dominated by a strong, dominant male to be one of my main purposes in life. You could say that it's my true calling.
You could also properly conclude that I feel this way because it's what nature must have intended for me, because of having born with ingrained feminine and submissive traits. And having begun life with such traits from the very start, I am very prone to easily falling victim to certain men manipulating and controlling me.
And despite being male myself, and fully knowing how abusive these types of relationships are, I continue to allow them to potentially occur because I'm very much like the woman who keeps choosing the bad boy boyfriends; because I secretly like the punishment that comes along with these bad choices.
Which is a bit of a perverse and even toxic condition for me to have and to be born with, because when this right person concocts a certain mixture of abuse, shame, and humiliation, the resulting cocktail is an erotic drug that I cannot get enough of. It's a pharmaceutical potion that makes me say yes, when I should be saying no. And it makes it feel good, while it actually hurts.
As a result of these intense desires and persistent feelings to become someone's Sissy, it's now not uncommon for me to find myself routinely daydreaming about having to be available for a strong man like this as his personal servant, for whenever and however he chooses to use or abuse me.
It's a thing that's tough to come clean about and to openly admit it, but the thought of being forced to undergo various forms of discipline training, or being required to engage in various sexual acts until I've been completely broken and then re-molded into someone that can properly serve him; both excites me and scares me all at the same time. In fact, these thoughts have become so consuming that they've now become an outsized distraction in my life.
This rumination could even be best described as a hunger that can now only be satisfied by eating something that could very well be dangerous for me to digest. Because for someone like me, picking the right man is like going out to pick wild mushrooms, and doing so without first knowing which ones will fulfill my hunger, and which ones might make me deathly ill. But either way, one of the two things is going to happen, and I'm powerless to stop it.
I freely admit that It's certainly his implied threat in those words which has left me in this tormented state. But by accepting his invitation to give him an opportunity to break and then remake me, I am returning myself to a place and state of mind that I've been to and in not very long ago.
And it's essential for me to disclose that this is a place and state of mind that I left on my own free accord, but only because I was the stronger-willed one in the relationship. So part of this epic struggle taking place for me is the realization that if I venture back into this world of being someone's Sissy, I will be returning as a much different and far more experienced person this time.
Because now, I perfectly understand what my responsibilities to men are. I also now perfectly understood what exactly it is that I am, which is of even more consequence. So there is that anxiety-ridden element of "there may be no turning back this time" in the event that this man turns out to be the true dominant that I seek, but also intensely fear. You know what they say: "be careful of what you wish for," because it fully applies to this situation.
I don't even know where do to begin on how to educate you about how this will be returning myself to a previous existence, so we'll start with these intimate disclosures about my last relationship and about me. Everything about me and my life is frustratingly complicated. It has been since birth. I have a complicated relationship with not only my gender identity, but my sexual orientation as well. The experts tell me that the two are supposed to be separate, and easily recognized as being separate, but for me they're inexplicably entwined and inseparable. My long-term marriage to a natal female is further complicated by these two innate states of my inner-being that bubble like molten lava within the core of my existence. Fitting someone such as myself into a straight, binary-sexed world is even more complicated yet. Because I was born into a society that came with a set of rules that others have constructed for me based largely on religion; teachings, moral values, and obligations as a result of being born male that make no sense to me. Even worse, I've never understood or had any respect for the very clearly marked boundaries of these societal and patriarchal norms.
As a child, I didn't understand why I couldn't wear a dress like the girls. Nor did I understand why I had to have my hair buzzed short like some boy version of G.I. Joe. As a highly feminine male, I just wanted to play jacks and hopscotch with the girls. But what I got instead was repeatedly placed on a team in endless games of "Smear The Queer" with the boys.
Looking back, the only thing that saved me was that I didn't understand or know what being queer meant. All I knew was that I was different from these other boys, and I did my best to hide it. In hindsight, it was like having sex with a female during the five days before ovulation while not knowing that you can ejaculate. The not-knowing factor muted the potential danger of the situation that I was constantly in.
When I explain that this time will be completely different by bringing a new dominant male into my life, what I actually mean is: I will be retracing a path that I have formerly traveled, but not as a male. Because the last time I did so, it was as a woman. That's why I say that this time, I will be traversing this path with a much better understanding of who and what I really am. Because I now know that I'm not a woman or a female. And because of this new and intricate knowledge about myself, I can also no longer pretend to be a female to shield myself from the fact that I'm really just a Sissy. But this acknowledgement of my true self is both liberating and problematic.
I describe this as being both problematic and liberating, because being a Sissy, I am someone who was born between the two sexes of male and female. I have the fully functional body of a male, but I also have the feminine traits of a submissive female. And Mother Nature flipped my sexual orientation also to further punish me. So I now understand that I am a unique, but naturally occurring variation of nature that throughout history has been destined to serve men.
Women typically service males because those men have something they want in return. But as a Sissy, I service men because I like it. But when doing so, I also require nothing in return, which sweetens the deal. And this is why men throughout the ages have always secretly sought out these girls-on-the-inside like me that come with a penis. In seeking out Sissies like me, men also know all too well that our pleasure is derived during the acts of giving them pleasure.
The harsh truth is: the identity of being a woman is something that I hid behind for several years to shield myself from what I previously considered to be the horrors of the real me. Because being a Sissy isn't exactly one of the most esteemed positions to hold within a patriarchal society. In fact it's quite dangerous. This is why Sissies are routinely kicked out of their homes in their youth when they are discovered to be Sissies by their families. Our Father's can't handle that we'll never be real men like them. And our Mother's or sister's don't like us wearing their skimpiest clothing and tallest heels.
In patriarchal societies like these, and in the one in which I was brought up in, you don't go to a shrink and get diagnosed as being a Sissy. And it's not like we're formally listed in DSM V or the ICD-10 as Sissies with an accompanying list of symptoms and traits. Instead, we get made into girls by the docs and the shrinks to protect us from ourselves and these societies. So it's important to understand that "woman" and "female" was a medically constructed identity for me which was designed to keep men from harming me; like some of them have been attempting to do my whole life.
As a feminine, male-born, gender variant, I've always felt a deep psychological need to be kept in the safety of female spaces with the women. That's because I can honestly say that my sense of self and my feminine behavior characteristics are more like those associated with being a woman than they are of those like being a man. I have to sit down to pee to feel normal for fucks-sake. What kind of a male has to do that? At the same time, I completely get it about why the doctors have been doing sex changes on effeminate males like me to "fix us." But in my particular case, the mental pain of my tortured existence ran so deeply that I became a woman just to avoid facing up to what I really am. But in the end, this life detour was just kicking the can down the road, and I ended up becoming a Sissy anyway.
I of course can't speak for other Sissies as to their motivations or as to the reasons that they do or don't do the things that they do, but for me, there was an intense need to keep my potentially volatile secret about really being such a feminine male deeply hidden. And I thought that this, what I considered at the time to be an unsavory detail about myself, needed to be buried extra deep beneath the layers of my psyche because of having to exist in such an unforgiving society; a patriarchal society that constantly sought to harm me due to my extreme gender variance. Or if they couldn't harm me, then they at least wanted to sterilize me so that I couldn't breed.
The sad truth is, I tried to change, I really did, but it never worked. That's why I played all those painful games of "smear the queer" with the real boys, trying to cure myself. It's also why I prayed to the Good Fairy each night at bedtime as a child to turn my penis into a vagina before I woke up the next morning. But despite all of those masculine sports, endless prayers to the fake fairies of my childhood, and all of the other manly pursuits that were supposed to help me man-up and ultimately change me, I still woke up each day as a Sissy. And despite the best efforts of the doctors to try and turn me into a female in an attempt to hide me from the kind of men who take great pleasure in harming lesser-males like me, well, that didn't work either. Because no sooner than those quacks that were passing themselves off as medical professionals did just that, I immediately found out that I was no more welcome in the female spaces of real women than I have ever been in the male spaces of real men. I'm just thankful that I caught on to what they were doing before I allowed them to cut my penis off and turn it into one of those fake neo-vaginas. Because then I wouldn't even have any value to real men as a Sissy either.
So this is some of the backstory involved in this difficult decision that I'm now faced with as to whether I should accept or reject the offer from this man to as he describes "break me." And if I decide to give him an opportunity to do just that, then it will be only my second long-term relationship with a male, and this new man will be replacing my last boyfriend; the first guy to ever stick a real cock in my mouth and ass.
But in telling my story, it's important to note however that this first boyfriend was someone who was just as guilty as I was at the time of not facing up to the reality of who and what he really was. Because in that relationship, while I was certainly guilty of living as a woman to hide the fact that I am really just a highly feminine male and a Sissy, he was equally guilty of using my legal status as a woman to hide the fact that he was really just a bisexual male with an occasional need for some ass pussy from a Sissy.
This first boyfriend, as my wife and I collectively referred to him at the time, liked the fact that even though I was biologically male, had a fully working penis, and had perky, little estrogen grown breasts; that I was legally categorized as a female by the State. And by virtue of that little piece of legal fiction, the relationship and sex with me in the eyes of the law didn't technically make him gay. But beneath his own mental self-protection mechanisms, he was just as much in denial about the fact that he was actually fucking a biologically male Sissy in the ass on a weekly basis as I was. In his mind It wasn't another dude that was bobbing and slobbering on his knob, and leaking his cum out of their ass; it was instead a transgender female that had the same legal status and standing as any other female, such as his wife. The self-deception between the two of us ran so deep that we even called my penis a clit.
While I will always have very special memories of the time that I spent with that first boyfriend and of the experiences that we shared together because he was the man that popped my anal cherry; the sad truth about the relationship is that he wasn't anywhere near capable enough of handling a Sissy like me. And his inability to properly train, discipline me, and earn my loyalty as a true dominant figure eventually created a considerable amount of resentment instead. Because in reality, through me, this man was living the very life that he was too scared to live.
The sad fact was that this caricature of a man badly pretended to be a tough guy, but the whole time I could see clearly as day that he was just another Sissy beneath his facade of pretend masculinity. That's why in the end that it all fell apart, albeit amicably, just a short number of months after the relationship began. It started off with me calling him Sir, and then ended with me being the first person to slide a sex toy into his ass while he squirmed beneath me like another Sissy. He didn't just want his cock sucked, he longed to suck mine also. And eventually I had no problem or regrets about "turning back," and in ultimately rethinking not only the relationship itself, but my entire existence of living as a woman as well.
As a Sissy, and in going into that first relationship of mine with him, I perfectly understood my role to serve that first boyfriend's needs, sexual or otherwise. And in return, he was supposed to have been my dominant master. My teacher. My keyholder. The person who humiliated or punished me as needed. The person who withheld my rewards until I begged for them, and then denied them anyway. That's what the arrangement was supposed to have looked like. But it never did, and as a result, my resentment festered like a sore that wouldn't heal.
Because my Mother gave birth to a natal born Sissy, and because I was born into this destined role of being a natural submissive, and because that's what nature originally intended for me: this first boyfriend didn't even have to train me. Because due to all of my inherently inbred feminine traits that were selected either mistakenly or intentionally by the commingled results of my Father's sperm and my Mother's eggs at the time of my conception, I didn't have to read ancient texts to figure out how to please men; because how to suck and fuck them was programmed at birth into my genes.
But as a modern-day Sissy, the instruction manual on how to serve him, or men like him, had been posted on the Internet long ago by the keepers of other sissies. And like the good Sissy that I was: I found it, read it and then read it again to make sure I understood it. And then I practiced my craft to perfection. My morning banana wasn't just breakfast, it was cock sucking and gag reflex training as well.
As a Sissy, who takes pride in being a Sissy, you wouldn't be wrong to say that I'm akin to a sexbot that comes preprogrammed with all of the nasty and erotic artificial intelligence that you could ever want. I was created for men by men. And I come pre-packaged, and with batteries already installed, to do all of the nasty things I'm supposed to as a good fuck toy for men.
Without being told, as a good Sissy, I kept my body hair removed and my skin smooth. I had my ears pierced. I scoured and hunted in thrift stores and adult shops for slutty wears and needed attachments. I wore whatever panties, lingerie, or outfits that he instructed me to for each visit. I followed his instructions and dutifully smeared his favorite bright red lipstick across my lips each time before sucking his cock. And I had my wife pump my previously virgin ass full of anal lube each time before his arrival; just in case he wanted to bend me over and butt fuck me that day. I even went so far that each time he came over to molest me, I would await his arrival while kneeling on a small pillow with a bowl of warm water and a soft washcloth beside me. If he was coming by after work for a quickie before going home to his frigid wife, I would cleanse his penis and cum swollen balls, before sliding his manhood into my mouth, and slowly going down on him until he gave me further instructions about the manner in which he wanted, or in which of my all available holes, that he wanted his testicles drained. I was his personal, feminized male, cum guzzling slut that had totally surrendered to all of his wants and needs.
The typical and familiar narrative in these types of stories, in real life or when written purely for fiction, is the tired and overused old trope about how the philandering husband has become the cuckold. And the heart of the plot is always that he's the poor schmuck that's been written into the part of being the cuckold after getting caught in some sort of compromising indiscretion. Usually with some woman. And as retaliation, or as punishment, which he of course always end up happening to like by the way, his wife is then fucking other men; either in private or with him being forced to watch. Or she's somehow otherwise punishing him in creative ways that are just too over the top for women themselves to ever come up with.
But in my case, and with that first boyfriend, as the relationship and the sex progressed, I soon began to realize that it was my wife who had become the accidental, but real-life cuckold in all of this. I certainly didn't start out with this in mind as the outcome as I set out to figure out what my true sexual orientation is with this new boyfriend, but things certainly ended up that way. Remember, I warned you that everything about my life and about my relationship with her is deeply complicated.
It was against this backdrop, and in my alone in the dark moments, that I began to realize that even though I had become legally a female just like her, that in reality nothing had actually changed in our relationship or marriage. She still mindlessly did whatever I told her. She still cooked and cleaned. And she still expected me to fix the car or her broken or crashed computer.
Despite me being a highly feminine male -- a Sissy -- in nature's pecking order I still held an elevated position above her as a result of her being a female that was born a female. Because of my penis and because of her vagina, I was still a part and would always be a part of the patriarchy, albeit a fringe element. And she was still squarely in the matriarchy at all times. And these things remained true regardless of her more than abundant masculine traits as a woman, which couldn't trump my feminine male traits, because I was still a male, and would always be a male, no matter how much or how many female hormones that I ingested.
Because of my naturally dominant position over her, and before I even realized what it was that was happening, I made it at least partly my wife's job before his visits to help prepare me for this new boyfriend's use and sexual pleasures. Just because of my wife's subordinate position to me in our existing relationship, she had unwittingly become my handmaid in this new normal that was now her life. And after I had been prepared for my boyfriend's use, my spouse was then given the choice to either watch the sex that was occurring, or to disappear for a few hours if she chose not to be a watcher. And in hindsight I feel bad in admitting it now, but she was even instructed to text and ask for permission to return. Unbelievably, she willingly went along with all of it. And once she even fucked him also, just because I told her too. Which I also regretted afterwards, because she later confessed that his manhood was hitting spots within her vagina that I'd never able to to; further proving what a Sissy that I really am.
In divulging all of the important facts about my newfound, and often upside down marital situation, it's of the utmost importance to disclose that for the first few trysts, my wife did indeed watch this first boyfriend and I having sex. But for me, this sexual initiation ritual with him to become a Sissy and to accept my existence as one, began as a process of self-discovery about my latent homosexual tendencies. And by being present, my wife was forced to watch as his cock first tested and probed the boundaries of my gag reflex, then pushed past my anal cherry and into the depths of my rectum, and then ultimately witnessing the sensational ending, with his bitter seed being pumped all over my face. But for her, all of this was especially traumatic because of the realization of how much I liked and enjoyed it as he debased, deflowered, and used me as his personal cock-whore.
This sexual exploration between me and him was a time of radical acceptance for both me and my wife. And I say this because throughout our marriage she'd never been able to just completely cut loose and let her most primitive sexual instincts take over. Plain and simple, she wasn't able to cross the the line between being a wife and being a slut. In defending that boundary, she could never totally surrender her body and mind and allow herself to be used in any manner that her more dominant partner chose. But now, she was witnessing me doing exactly that. And it frightened her. But, and I have no way of being entirely sure, but judging by the look on her face and based on the amount of juices that would pool in her crotch afterward, I also think that it excited her. She couldn't bring herself to admit that however.
Up until this point, I think that you could sum up our marital relationship as: "she fucked me because it was her duty to do so as a wife." But I was fucking this boyfriend because I not only liked it, but also because I also needed it. Those are important differences. That's why smart men prefer sissies over natal females, because we've got a girl brain that's been fueled by an abundance of the sex hormone testosterone. And this is why a lot of middle-aged men eventually find themselves in some seedy hotel room with a feminine male like me, that's down on their knees in front of them, getting their dick sucked, before spraying their load all over that Sissy's face. Let's be truthful, the wives of these type men often balk at the idea of going down on them. And they don't swallow cum either; they instead spit it into a tissue and treat it like a big piece of snot that had attempted to slide down their throats. But Sissies get in line to do both of these things, suck and swallow, and anything else that a guy wants. But by far and large, the most interesting as well as the most important disclosure in all this is the unspoken truth that my wife has far more of a perverted streak in her than she's ever been willing to admit.
And an interesting side note in this recollection is that my wife had as much trouble unscrewing the relationship between her perverse desire to watch these sex acts occurring between me and him, and the ensuing jealousy that these actions unleashed, as I do in trying to separate my gender identity and sexual orientation. As I -- my wife's used-to-be husband, who at this point had now been turned into a female, both hormonally and legally -- was playing the part of the girly girl that she had never been and never was, her jealousy was boiling at the same time as her juices were flowing. Which for her was quite a conflicting and contradictory message to be receiving and similarly trying to unscrew. Throughout most of my torrid affair with him, she couldn't decide whether to take the boiling pot off of the stove that was her head, or to stick her fingers in the likewise boiling over casserole dish in the oven that was her vagina; because she didn't get instructions to do either from me. And she depended upon those instructions to do anything. But after months of either watching the intense sexual activity playing out between me and him, and by being stuck in the role of accidental cuckold, my wife's jealousy eventually won out; overpowering the sexual excitement that she was getting as a not-so-victimless-voyeur, and instead channeling those pent-up emotions into some serious anger.
It's also not only interesting but fascinating as well to note that despite my wife's crotch being dripping wet after each time my boyfriend had departed, she was far too shy and guilted about what she had just witnessed to pleasure herself. I know this because I checked her arousal level several times by running my fingers through the folds of her vagina after he'd had walked out the door. And each time she was deliciously hot, wet and well past the point of being amply lubricated enough to receive a male and mate with him.
But despite my wife's burning and obvious arousal, I did nothing to relieve her heightened state of sexual frustration. Because at this point we were both females and I no longer had any obligation to play my previous role of being the male in the relationship. Which also meant that I was no longer responsible for getting her off each time that we had sex. The male had just left: I was now just another female like her, and I no longer even liked using my penis as a penis. Because we both had clits now. Mine was just bigger than hers. And I mentally viewed the whole thing as me now being responsible for pleasuring males just like she was, which I was certainly doing. So without any guilt or remorse, I would just leave her in that elevated state of sexual discomfort, because she was not only too unwilling and stubborn to ask for any relief, but also too unwilling for whatever the reason to even give herself any.
You could further describe it as her having been conditioned to get something in which she was no longer getting, and not knowing how to process that. She was used to being the receptacle for men's sexual organs, and now we were both receptacles for their phalluses.
The sad truth in all of this is that my wife of decades couldn't master the mental gymnastics of what was happening to her enough to allow herself to masturbate during all of those months. And I intentionally didn't give her any instructions to do so. But I suspected that this was happening because by getting herself off, she would be succumbing to the guilt of the sex acts that she'd witnessed happening between me and him. And for her, she would be admitting that what she saw happening between us was actually arousing her. And she simply couldn't bring herself to do that. It was all so confusing for her because up until this point she had always just been nothing but a wife that did exactly and only what she was told, and now she found herself in totally unknown and unfamiliar territory. Her fate and the state of relationship were clearly uncertain.
In the long run this perverse cycle of him coming over for a couple hours each week to do with me as he pleased devolved into a pattern that during my encounters with this first boyfriend, that at first she would simply suffer in silence, but yet at the same time be unable to look away. But as more and more sessions of watching and suffering through the sex acts occurred; and as the mounting knowledge of the natural talent that I had for fucking and sucking men as another female mounted; and as the potential implications of what all of this could mean for her and our marriage sank further and further into her head; my wife simply stopped watching and instead developed a ritual of meeting him at the door of our apartment building. At this low point, she would simply hand him the keys to our studio flat, and with a forced smile on her face, she would then disappearing for a couple of hours, which became the norm for her.
Where it all further went bad was going into that relationship with this first boyfriend, I had agreed that he would use me as his Sissy for only one afternoon per week. But instead of fulfilling my role as a submissive, feminine male, I instead became his real girl on the side. And before long I soon found that having sex with him under the pretense of being a "real girl" felt totally fake to me. What I really wanted, needed and craved was for him to use, abuse, and humiliate me as the Sissy that I am. Instead, I found that he wanted to treat me like the woman that I was not. Don't get me wrong, at times he definitely treated me like a slut, and I felt like one as well, but there's a striking difference between how you treat a slut and how you treat a Sissy, because the Sissy gets treated as a combination of both.
There were other problems as well for me with this new arrangement that I'd dove into head first. Despite the fact that this first boyfriend wasn't overly creative and was actually somewhat shy about telling me what sexual acts that he wanted me to perform for him, with him, or on him each week, I realized that I suffered from neither of those two problems. I wasn't shy at all. And I certainly didn't lack creativity, in the bedroom or anywhere else. Just about anything other than pissing on me or leaving me bruised and beaten was fair game. My main rules and limits are: you can't leave anything other than very temporary marks on me and everything has to have an underlying erotic tone to it.
On the subject of pain, pleasure, masters, and slaves, before getting into the relationship with this boyfriend, I gave it a trial effort with my wife to see if she could play the role of the dominant in our relationship, so that we could avoid bringing a 3rd party into our marriage, because it's always risky for lots of reasons to do that. I just wanted sex, I didn't want to catch HIV or HEP C. But despite completely surrendering myself to her for a couple of weeks, it felt just as fake with her as it did now with him. Neither of them had the mental credentials to be true dominants. And even more shocking, in some ways my wife was able to better roleplay being a dominant than he could.
I have to intimately confess that while given that opportunity to be in charge, my wife wasn't afraid to demand that I kneel on the living room ottoman while she paddled my ass for failing to call her ma'am when I'd spoke. She also really got off a couple of times by donning a baseball cap and putting a strap-on harness with one of those big, fleshy dildos underneath her jeans, and then forcing me kneel and suck her cock; before sliding it up my ass. I have to admit that it was erotic as fuck, but at the same time it just wasn't real. It still felt fake. I wanted the real cock. I wanted the real man doing this shit to me.
As his Sissy, I felt like it was my duty to make sure that each of his visits had a different theme, or that each occasion repeated one of the previous scenarios that had really gotten him off; things that he didn't seem to tire of doing or repeating. The size of his prick and the expressions on his face were my measurements of success. But beneath the surface of it all, there was that same superficial, fake feeling that I'd experienced when my wife had attempted to play this same role with me. He just wasn't the right one. And once I realized that he viewed our relationship as him just banging a sexy female on the side; it was basically over. The magic was gone. And when that realization finally became total reality for me, I came to realize that in this in this particular relationship, I had been just honing my submissive and sexual talents for the very dominant man who would truly own me at some point in the future.
To this day it's still hard for me to be critical of that first boyfriend, even if I sound or come off that way, because he was just so nice in general as a person. And that's the kind of people that I surround myself with in real-life on a daily basis. But "too nice" was exactly the problem, and it doesn't cut it for what I need in the bedroom on occasion. And eventually it started to dawn on me that this was the exact same sort of thing that some of the women that I was fucking when I was younger would tell me, about me.
Unfortunately, back then being told that I was "too nice" just bounced off of my impenetrable facade of fake masculinity. In those days during my youth and early attempts at manhood, and while doing everything that I could to be as male and masculine as I could be; I never understood why at first it was teen girls and then later adult women that were saying this about me. But I totally get it now, and it's because I was so much like them because of my feminine and submissive traits.
Some of these females even confessed that the way I touched them was totally different than any other guy had ever did. My soft touch and female mannerisms probably worried them that I was making them gay. And I realize now that the girls and women saying this to me had been expecting to be used by a real man, in the same way that I had been expecting this boyfriend to also treat me. And because of these formative new learning and growth experiences that I was now going through, I was also now having this powerful realization that the needs of these girls and women back then weren't being fulfilled anymore for them by me than my needs were by him in this relationship. In fact, I was downright frustrated by his gentleness. It made me just want to scream something out in frustration.
It's tough to describe what you want or what think you might want when you haven't actually gotten to actually test everything out yet, but I'll do my best to try and describe these thoughts and feelings that I was having at the time and try to put them into something that you can understand. I wanted him to make it hurt, but without truly hurting me. I wanted a male that made me feel powerless and vulnerable around him because he naturally exuded the characteristics that triggers these feelings in people. I wanted to be unsure of the outcome and direction at all times because he was always in control. I wanted to feel danger, but at the same time know I wouldn't end up as a smell in his basement wall. I wanted everything to happen at the time of his choosing. I wanted to be taken to the edge, and suspended there, until he decided whether he'd push me over or safely bring me back inside. I wanted all of that and more. I dream big and fantasize even bigger.
But instead, I felt like I was the more dominant one in my current situation. I had this perpetual longing to be taken to that pivotal point of the unknown, to be left suspended there by him, and to be unsure of the outcome before ultimately landing safely; but exhausted by the experience. I wanted to be fucked hard and put away wet. And I was well aware that others had left me to find the man capable of fulfilling this need in them, so I now found myself secretly packing up for the same departure and resulting journey.
And while I was keenly aware that I had a wonderful wife that deeply loved me, and that I also this wonderful boyfriend on the side that was giving me lots of great sex and treating me completely like a woman; there was still that underlying tension that none of it was truly working for me. I was still hungry for the thing that I felt like I hadn't found yet.
My initial and "trial" meeting with that first boyfriend, which occurred in a very public place just to be on the safe side, should have been the canary in the coalmine that we weren't right for each other. But by being so inexperienced back then, I wasn't sure of how to read men at all while I was in that phase of pretending to be a woman. Worst yet, I didn't even know how to interpret men as a male, because I'm a Sissy and I've never been a real man, so I've always lacked that social skill-set. It was this hellish zone of being terrified of men on one hand and at the same time desperately wanting one on the other. And behind it all, I suffered with the harsh knowledge and guilt that my deeply rooted homosexual desires for men really just meant that I was just gay and couldn't accept that. I was very much aware that this is what some of the shrinks say about people like me. They think we're little gay boys with a mental-complex. At this point, I still hadn't figured out my true place in the world, but I was actively searching for it. And in the midst of this huge, unfilled void that I was seeking to fill was an equally large amount of guilt for seeking to fill it. I was so far beyond conflcted that Google hadn't mapped it yet.
Myself and this first boyfriend had agreed to meet at a coffee shop near my home. And when that day finally arrived, I found myself standing in the rain beside his car beneath a big, black umbrella. I'd brought the one that had came in the trunk of my Mercedes and had their logo on it; so that everyone who saw me dressed like this would know that I wasn't a prostitute; and wouldn't try either hitting on me or fucking with me. Besides, hookers charge for it. And I was fixing to give some away for free.
To this day, I can still remember what I was wearing. I had on a black, plaid trench coat that I'd purposely left open despite the cold, because I wanted to channel his view into the inviting and intentionally left uncovered space between my pair of knee high boots and the short jean skirt that was barely covering my ass. I also fully admit to wanting this total male stranger that I'd only ever spoke to before online to see my shaved smooth, creamy, white thighs that were adorned with tan and brown thigh socks. And like the slut that I am, I even further admit to having arrived fully intending to show off plenty of leg and ass as well as my braless chest. I was perfectly aware that my areolas and nipples were clearly visible through my sheer, white blouse, because I had made sure they did.
Because of all the male socialization I had prior to becoming a woman, I never felt a need to wear a bra or be ashamed of my breasts. I was often reminded of this by the actions of women that I would observe and study for social cues as they conversed with men. I would always see them unconsciously fixing their sweaters or jackets to conceal their chests. These women had been socialized to be ashamed of their breasts in public and to keep them covered in the presence of men since birth. I always thought it was quite tragic. But because of my male socialization, I wasn't afraid to rock my hormonally grown titties anymore than the muscular guy at the beach was afraid to rock his muscle bound chest. I'd waited decades to have these mammaries and I wasn't shy about showing them off for any man willing to look, or even stare.
I had spent a lot of time primping to look just like the slut that I was purposely coming off as for this first meeting. My look and behavior was bold and audacious. So audacious in fact that my wife had scolded me about my appearance before I disappeared out that door for that fateful first meeting.
I've never been low on self-esteem, and honestly, I thought I looked really hot that day. And I was totally confident that I did, but unlike in our email conversations that led up to this meeting; he was now suddenly acting uncharacteristically shy and nervous in comparison to his previous online behavior. This man, who in reality was still a total stranger to me, was also even unwilling to get out of the car and go inside of the coffee shop with me. At first I began to wonder if he was scared of "being seen with a tranny" because of the way I was dressed, which is a common trait in the men that wanna fuck transsexual women. But then when he soon asked me to get inside of the car with him, I started thinking "oh shit, serial killer," because of his strange and openly nervous behavior. Later though, after another few minutes of chatting, I ultimately realized that he was just incredibly nervous and intimidated by me, and I did get into the car with him to chat. But I also checked to make sure I had a door handle, that I hoped also worked, before closing it.
Everything about that first meeting should have been my warning beacon and an alarm should have been going off that I wasn't really getting the type of person required to handle someone like me that can be strong-willed and that's developed a dominant side as a survival mechanism, but at the time I was too naive to even remotely realize that back then. And it's completely fair to say that my hunger for that first real cock up my virgin ass had clouded my judgment. Embarrassing to admit, but completely true.
That first boyfriend's favorite roleplayed scenario during our numerous meetings that occurred at least weekly, and sometimes more than once per week over those several months, was for me to be dressed up as a teen schoolgirl. Which was something that I really got into doing because it was like a big missing part of me from my childhood, especially my teen years, that was now being carefully restored when acting out these fantasies with him. I just felt like this schoolgirl mode was the kind of thing that should have happened during my highly sexual active teen years, but of course never did, because I was forced to always pretend to be a regular male so that boys wouldn't beat me up.
I guess there's a certain irony in the fact that some of the same homophobic men that used to beat-up kids like me in high school later in life in their 50s then come to have these same types of feminine males sucking their dicks in adult bookstores.
And while I've talked lots about how for the most part that me and him had established a set meeting agreement of once per week, we did sometimes deviate from that set schedule and meet more often. Such as the time on New Year's Eve when his wife was out of town for a couple of weeks and I had been cock-teasing him throughout the day with sexy text messages and pictures to get him worked up before our next planned fuck-fest. I'd sent him some photos that my wife had taken of me perched on the ottoman and with her paddle resting across my ass.
Those photos with the paddle had of course been my idea, because my wife lacked the initiative and creativity to think up something like that, but I had correctly figured they would come in handy at some point in the future, and I was right.
So on that particular night, I guess I took the prick-teasing a bit too far, because I got him so horny with the half-naked selfies and with the pictures of her disciplining me that I was sending that he ended up asking if he could come over right then and have me fix the problem in his pants that I'd purposely created? This was like 11 PM.
I of course said yes, but at the same time that I was saying yes to him, the look on my wife's face was saying a very clear not just no, but hell no back to me. And she also made it quite clear that him visiting on such a traditionally celebratory night for the two of us was in her opinion a significant intrusion into an evening which had historically always been her exclusive real estate on the calendar.
But by this point in the relationship with him, my wife had already been fully forced into assuming the position and role of being the cuckold, so we simply ignored her weak protests and he came over anyway.
Looking back on that evening, the whole thing was pretty harsh on her, but it's factual to state that me and him were so caught up in fulfilling our own desires at the time that we readily opted to leave her in that disgruntled position and mindset. Or to be more blunt, she was basically left to quietly watch either the TV, or us as he blew a massive load of cum into my mouth right as the ball dropping.
People often picture the cuckold as someone who's been tied up and forced to watch, but she was so well trained about her place in the grand scheme of all of this that rope wasn't even necessary.
After orally finishing him off, I fully had the distinct impression that his wife had never before given him a blowjob to ring in the new year. And the timing of him coming as the ball was dropping couldn't haven't been any better as an extra special memory for him.
The memory of that evening for my wife probably isn't as good, because as the people in New York were watching the confetti floating to the ground, she was watching me slurp in a whopping mouthful of his vile semen. But instead of swallowing his stringy juice, that tended to be dull white like the color of pearls like I normally did; this time, I instead slow allowed it to leak out of my mouth and back onto his still pulsing, rock hard cock.
It was quite the scene and probably my best blow job ever, because I was basically using his penis as a brush to smear his cum all over my face and paint my favorite self-portrait. And for full-effect and to give him a little extra thrill, I even allowed some of his jism to drip onto my bare breasts. I also made no effort to leave and get cleaned up; instead opting to remain there between his knees, looking up at him like a little cum-covered slut that was awaiting her next set of instructions.
Everything I'm saying now is how it all really went down during those months. Once, and as I grew bolder and bolder, I even met him at the building door. On that occasion I was deliciously made up as a young school girl, and had come down to greet him and let him into the building; just to make him nervous at the thought or possibility of the neighbors seeing him with me like that. And I would always typically take these themed encounters a step further than he ever dreamed of, which is probably why he was so distraught upon losing me after I officially broke it off.
Such as another time when he showed up expecting to molest the little teen schoolgirl that he'd once again requested. It was on occasions like this that I would roleplay being a braless-teen-youth that called him Daddy at every chance. Before his arrival, I would be sure to carefully decorate myself in a tight, grey skirt that featured a plaid pattern. And I'd be wearing an equally tight, sheer white blouse that bordered on obscene and did absolutely nothing to hide my big, perky nipples.
My clothing was actually an authentic schoolgirl outfit that I'd ordered from an actual school uniform website. And I should add that prior to his visits that my nipples had always been previously engorged by the same kind of electric breast pump that's used by the mothers of newborns. In fact, I used to pump my breasts for days before his visits, doing it until my nipples were be as big as the erasers on the fat pencils that he first learned to write with as a little kid. And my areolas would be left as puffy and stretched as widely as something that you'd see in some soft of fetish magazine that featured late teen girls.
And beneath this totally age-inappropriate clothing, I'd have on something such as pink, polka dot panties, that would barely cover my little, shrunken, hormone fed penis. And with all of those girl hormones that the doctors had given me coursing through my veins, that poor little boy clit of mine just constantly leaked sex juices like an actual wet pussy. Which was embarrassingly noticeable when I wore dark colored panties.
My little clit which had been beaten down in size because of all those hormones and being in such a state as that all the time was really quite a deal for him for whenever he'd decide that he was in the mood to suck me instead. Because unlike his large gobs of nasty tasting, foul smelling cum that I struggled to swallow and that tasted pure awful, he barely had any trouble sipping down the small amounts of clear, sweet cum that I was still producing. No stringy, white stuff was coming out of me; it looked like the same clear substance that oozed out my wife's cunt when she was excited.
And to make it all even more authentic on these occasion, I'd even be wearing a pair of black Dansko clogs and white knee high socks. But his real shock would be in little twists and turns that he never saw coming, like finding me locked in a CB6000s cock cage.
I still fondly reminisce about the time that I instructed my spouse to give him the key to the cock cage without explaining what it was for. And another time, when per my instructions, my wife left me blindfolded and tied spread-eagled across the bed for his use. His surprise on that meeting was in discovering the large butt plug that had been pre-lubricated and stuffed into my ass by her.
Thinking about that day still makes my groin ache, because after he fucked me in the ass and pumped me full of his cum, he put the plug back in and left it for her take back out again. She'd left me full of anal lube. But he squished nearly all of that lubricant out of me, and left me full of sperm instead. My wife not only had to untie me afterwards, but she also had to wash our dirty sheets.
And it was such a delight when with the cock cage locked firmly in place, he would use all of my holes before deciding which one that he wanted to cum in; before finally unlocking me to satisfy my own needs while he watched. But back then it wasn't registering with me that he shouldn't have been freeing me, and should have instead been keeping me permanently locked up.
But all those little things and the added touches like the cock cage or the butt plug were always my idea. And in reality, and as my resentment with him grew, I came to realize that this boyfriend's penis should have been locked in a plastic cage too. I guess I was starting to feel like I should punish him for not punishing me.
I say all of this mean stuff not because I'm not a nice person, but instead because of his unwillingness to properly control, discipline, and supervise me as a Sissy. Because of his inability to dominate me, I begin to think of him instead as a potential sissy sister; a sibling that I would supervise, and one that would get used alongside of me by real men that the two of us would invite over. And I thought this because he was so oblivious to how I was feeling inside and about what I needed.
A couple of times I even asked him: "are you sure you're not trans too?" He of course assured me that he wasn't, but I still had my doubts. I was growing concerned that he might really be a "chaser," which is a person that can't transition, so they instead live vicariously through the trans women that they date and fuck.
I say all of these things because at this breaking point, I'd reached the conclusion that he simply wasn't the type of real man that I needed. And he certainly wasn't capable of handling me. In the end, I came to realize that he had a terribly poor understanding of what my needs as a Sissy were, and that he'd pretended to be a dominant just to secure me as his girl on the side. He was steadily breeding me, but the only thing I was giving birth to was resentment.
In the beginning of this grand experiment about my sexual orientation, me fucking other men was supposed to have been just a test that my wife and I had agreed to. At that point, I was a couple of years into living as a woman and I felt like we really needed to find out if I was actually just gay and hiding it behind a female identity? And after several long and intimate talks about my innermost feelings, my wife and I had mutually concluded that the question of whether or not I was really a woman had to be fully explored and answered for the good of both of us. And that lingering question had to be answered because of my ever increasing need and attraction to men, which was becoming quite a distraction in our relationship. And she knew it.
Going into this "real life test" as we termed it, she of course had significant fears that I might actually like men more than women and then leave her for one. But because of her enduring love for me, she went along with the experiment despite those worries; even if it meant eventually setting me free to live as a gay man.
Ultimately however, due to the mismatched partner that I'd ended up with, this test that we conducted to see if I were really just gay was a near-total failure. And the lingering question was left still unanswered. Which still troubles me to this day.
In the end, the only clear thing that had been definitively established during this elaborate test was that by my wife being repeatedly subjected to watching all of the sex taking place between me and him, that the whole experiment had sent her fears and emotions into literal orbit. By watching him fuck me in the ass all those times and by seeing him repeatedly cum in my face on multiple occasions, and by seeing how much I liked all of it; I think she and I both knew that this was still unfinished business. But for now, as a truce, we were agreeing to silently end it.
But the ending of it meant different things to both of us. She thought I ended it to come back to her and because I'd figured out that I wasn't gay. For me however, I knew this ending was for completely different reasons; he just wasn't the right one.
In the end, the sex had been fun, but in reality things hadn't gone as well as I'd hoped, nor as well as I had planned. And soon after breaking it off with him, I also stopped living as a woman. Because I'd reached the conclusion that I wasn't one. Nor did I wish to be one any longer. I'd accepted the reality that what I am is a Sissy. And I started telling myself that.
"Once I break you to suck and bend over for me, there is no turning back. Think about it."
Which brings us to the present and the most recent offer that I'm now lost in thought and obsessing about. Which is the same one that I shared with you in the beginning of these confessions about the past couple years of my life.
I've now spent the past eighteen months back living as a male, but also still taking my girl pills. And during this period of restraint and reflection, although the harmony has since returned to my marriage, beneath this peaceful appearing existence, my turmoil and confusion about my sexual orientation still swirls. So despite my male clothing and the illusion of peace and content in my relationship with my wife; my inner need to serve a strong man as a Sissy has persisted. And this nagging need to service men is something akin to being eternally hungry.
That's why I sit here now, pondering this new offer. Because the inner sissy inside of me tells me that it's my duty to suck his cock and to bend over and take it in the ass. And my inner voice is practically commanding me to take the test again to see if this male can actually break me in the manner that I dream about being broken. But at the same time, I fear that if I do this; there really will be no turning back this time. And because I don't have anyone else that I can share these deep thoughts with, I'm choosing to share them with complete strangers instead.
***** This story may not be republished for profit. Comments are welcome providing that they are respectful or constructive.