Journey to Trans Submission Ch. 01

It has been at least thirteen years since I first discovered my kink and one year since I started to think about making it come true. This is a kink I have not shared a word with anyone for a fear of being judged and a fear of being told that it was not right to indulge in such objectification. Finally I came to the point where I said "screw the world, it's my life, my kink & I will explore it".

The first time I discovered my kink was in 2007, when I was uncovering the big bad dark world of internet porn. At the time there were a very few free websites and all I could do with limited financial means was torrent download the videos. And then came up one free website which changed my preferences for ever. I had been regularly gratifying myself from 2004 on through magazines, soft porn & hardcore much later on. And all of these were your regular straight porn videos which began with an unrealistic storyline, a woman in skimpy clothes needing to be ploughed, and a guy (sometimes multiple) giving the nice lady the slutty treatment she deserved through incessant 8 plus inch & fist girthed cock pounding that first violated her mouth, then her wet nether regions between her legs, then her rather elastic back room entrance between her rotund butt cheeks. And this finally culminated in the prized money shot with white ropes of silky sticky gooey cum splattered all over the nice lady's outstretched tongue, open lips, & dripping down her chin. The pattern of these videos were the same & after going through thousands of hours of these videos, I yearned for something different.

In the summer of 2007, as I was surfing through internet porn, with a cock out in one hand, I came across a new blinking link which read "categories". Intrigued, I clicked on the link and saw 3 signs - 2 of which I understood. The third one caught my attention - the insignia read "shemale". And I was drawn to explore further what this even meant. Fifteen minutes later, my cock, for the very first time, erupted with a big load coinciding with an on-screen male orgasm. My new favorite porn star & now secret crush, Yasmin Lee, was destroying a twink with her 8 inch long tool. As she stood in missionary pose, between his legs in the air, with her tool penetrating his clenched butt hole and his erect dick and blue balls clasped in her vice like grip, she looked into his eyes and in a husky tone, requested ever so lovingly, that belied the power she wielded over him at that moment - "will you cum for me?". And that resulted in the guy shooting cum out through his cock hole all over his chest. And with me shooting cum all over the screen. And when she proceeded to cum on top of him & then feed him the double load, I knew that a whole new world had opened up in my head.

At first I was confused to what I saw. Reading up more I learned shemales were a derogatory porn term for transgenders, along side terms like chicks with dicks & ladyboys. They were biological men who were transitioning to women through different treatments including breast augmentation, & hormonal treatment but had not yet gotten rid of their masculine tool. My knowledge about transgenders & repeated self gratification to shemale porn led to further self doubt & shame - was I attracted to men? I knew that was not true as I was a full blooded hetero man who was turned on by women. The girlfriend proved that. My lack of sexual interest in males around me proved that. Was I bisexual? Was I bi-curious? I had no answers except for the one answer - I loved watching shemale porn. I loved watching the power dynamic flip - a well endowed beast of man being turned into a tender bitch & made to squeal like a kitten. And the initial curiosity turned into a well established fetish in my psyche. Not a week passed by since without me jerking off to shemales burrowing their dicks deep into their subservient male sexual partners mouths & butt holes.

Though I always fantasised about being bottomed by a shemale, never did I ever think of doing something about it. That was until a year back. A major life event made me realise that life was too short to think about what my friends & family would think about me if they found out. I was surfing as usual for shemale porn & googling for details about a model I had jerked off to the previous night. I found a site which told me how she was a few hundred miles away in a neighbouring city. She had great reviews & her profile pictures were even more amazing. I could feel a hot flush passing through my body as I copied the number & dialled it. I could hear the phone ring on the other side & Lianne picked up, "Hello"! I was sweating profusely & I immediately hung up. I wasnt ready. My first attempt at getting some with a shemale was an abject disappointment. My raging hard boner was now gone & was replaced with a sense of anxiety & shame that I was now trying an escort service. It also played on my nerves that Lianne had 43 reviews - it meant she was great, but it also meant that she had been with 43 different clients at the very least. The risk of contracting an STD put me off the idea for the next couple of weeks. I shut off my computer & willed myself to sleep it off, & forget it.

Forget I did, but only for 2 weeks before I arrived at the shemale escort site again pursuing my deep dark desire to be subjugated by a shemale as her sex toy. I looked for Lianne and she was gone. She was in a different country now & I was crest fallen. She was the most popular one there who had great reviews. A lot of the other escorts were flagged as fake, which made me even more sadder that I had missed my chance. On a whim, I clicked on who's new in a 50 mile radius & saw 5 new escorts who had joined the site in last 1 week. One of them, Laela, had a great review already while the rest 4 had nothing of note on their profiles.

Laela's profile was short, brief and to the point. She wrote that she was half Asian half German, had a 9 inch long & 3 inch girthed tool, could top or bottom & charged 500 dollars for the night. Her profile photos did not have much to substantiate her claims. In my head, my voice told me it was all too good to be true. I was about to close the profile when I saw that she had stated that she was STD free, & would produce it to a client before the deed. And she warned off suitors not to contact her if they were not willing to share their health certificate. That was all I needed to know that I would at the very least try & contact her.

And as I was noting her number down, I saw the grey icon go green on her profile. She was online right now! And I could chat with her if I wanted to. More like, if i could gather the courage & my wits about it. My heart was pounding out of chest as I gathered all the courage and typed in as nonchalantly as possible, "Hi!'. 2 minutes passed without a response and I thought that I had lucked out. I reassured myself I would call her the next day. And got up from my chair when i heard a ping which got my blood immediately shooting to my organ. My brain froze when I saw the response - "Hi back muscboy87! Can I say that you look really cute & so doable in you white shirt?"

I felt flattered. And then a sudden feeling of paranoia struck. How does she know about by white shirt? My brain refused to operate further. I stayed motionless contemplating if my privacy was breached & whether I should close the window & get out of there. And another ping. My brain was telling me that the person I was chatting with would start blackmailing me next.

"muscboy87, don't mind me being too forward! I speak my mind. I checked out your profile on the site & thought you were cute. So tell me muscboy87, what do you want from me?"

I felt a sigh of relief. I had totally forgotten that I had uploaded a picture of mine 2 weeks back. I said to myself - no going back now muscboy87!

"thanks for the compliment. I find you cute as well. I was checking the site out & found your profile interesting. I am hoping we can catch up & if things go well maybe hook up"

Laela: "aww, so sweet! this is your first time, isn't it. On an escort site."

Me: "nope "

Laela: "you lie."

Me: ":O it's my second time visiting the site. Never contacted an escort before. But howd you know?"

Laela : "regulars are generally upfront about where they can catch up, fuck & bucks they need to shell. you wanted to talk first, like it was a date. I like it :)"

Me: "There goes my chance of putting up an act like I was a regular."

Laela: "Don't worry. I'll guide you through it. Let's talk like you suggested. It's a great idea. Tell me what's your deepest darkest fantasy & I'll make it come true."

I was headed into uncharted territory now. Never had someone spoken to me like this & made me feel comfortable sharing my kink. I felt a new sense of courage surfing through. I promised myself I'll be honest. Worst case, I would disconnect & Laela would dismiss me as another one of the creeps who lacked courage to move forward, & never know who I was. Confident that all would be Ok, I typed back

Me: "for years I have wanted to be bottomed by a shemale"

Laela: "oh darling! Every other man wants that to happen to him. Tell me what's your deepest darkest fantasy"

"What?" I thought to myself. Every other man - surely that can't be true. Was i living in a bubble of my own making imagining up all the judgement. Trying to understand what she meant, I typed back.

Me: "I don't understand. Being bottomed by a shemale is the fantasy I have"

Laela: "Ok - let's go about it a different way. How do you want to feel when you're being bottomed by a shemale? Do you want to be able to fuck her back after being bottomed?

Me: "No"

Laela: "When you are with your shemale partner, do you want her to fuck you lovingly like a virgin boyfriend - slow and steady? Or do you want her to teach you a lesson that she's the boss & she controls you?"

A raging hard boner in my pants told me what my brain wanted.

Me: "Id like to be taught a lesson"

Laela: "Good, we are now getting started muscboy87"

"Started?" I thought to myself as Laela pinged again.

Laela : "there are different types of lessons that can be taught depending on how you react to the lessons. These can be purely physical subjugation, or purely emotional subjugation or a combination of both. And in each of these lessons there are varying levels of difficulty. With physical subjugation, you will taught a lesson to comply with your shemale's dominance through physical pain. With emotional subjugation, you will be taught to comply on a psychological level. And in the third form of subjugation, you will be schooled both through physical pain & psychological shaping. If you're a beginner to bondage & dominance play I'd recommend physical play only. Emotional play might not be something you'd want to try as a first timer."

Me: "You sure sound like an expert. Are you a psychologist or something?"

Laela: "You're in safe hands. Don't worry. But if you must know. I have been a practising shemale dominatrix for about 3 years now. And yes, I did major in psychology a few years back."

I was astounded. This felt like I struck gold finding a shemale dominatrix. Impulsively, I also wanted to ask her what she was doing escorting. But then better sense prevailed and I went back to her suggestion on physical domination play.

Me: "Amazing to hear that you are a practising Dom. I have dabbled in BDSM before but with one of my ex-girlfriends. But there I was the dominant. She never liked playing the domme to my submissive kinks. I want to completely feel my sub kinks which I have repressed over the years. I was thinking the full experience. I'm sure I will enjoy."

Laela: "Exactly why I know that you're not ready. You don't *enjoy* with the full domme experience. You take pleasure in giving enjoyment to your domme. Very few people who aren't readying for the full experience make it through, and remain sane. I had one such sub who successfully made it through the full domme experience - it was a difficult period for both of us first. But now he's a much better person both sex wise & life wise. Multiple subs that I had wanted the full domme experience to only back out half way through. In such a case, the sub is left with memories which he perceives as bad since the brain has not fully accepted dominance of the partner still. Do you still want the full domme experience?"

Not blinking twice, I wrote back.

Me: " I'd love to be your second sub that made it through without prior experience."

Laela: "I knew you were cute. Whether you're strong or not - time will tell. But im starting to like you, my pet. Why not play a cute little game? Start calling me mistress."

My raging hard boner was popping through my boxers. I could see a wet spot forming against my cock tip. I was dripping precum by just chatting with Laela. Not giving a second thought, I typed back.

"Yes, mistress."

Laela: " Good. You catch on quick. To go full domme, I need to know a few things which I'll ask now. After that, I'll explain how we will go about doing this. We will sign a non disclosure protecting both of us. We will share our latest health certificates before starting off & periodically during the experience. And since I'm not going to be escorting for you, I will not be taking money. Instead you'll pay me tributes being the sub that you are."

All this sounded so formal. Just like 50 shades book. But wait - she just said periodically, what did she mean?

Me: "Periodically?"

Laela: "For the full domme experience, I need to break into your psyche, and physical world, flip it inside out, break you completely & put the pieces back. This takes dedicated time & effort. For our first experience I will be dedicatedly working with you 24x7 for the first four weeks."

I was wondering if it was too late to back out now. Should I just close the window and make a run.

Laela typed back seeing the delay in my response - "Run now & you'll be a coward. Not worthy of being my sub. Stay & you'll be a better person for it a few months from now.

That was enough to tell me that she was the one. She could already read my thoughts. She is the one who'll rid me of my shame & guilt & baggage.

Me: "I'm yours mistress. Where do I sign?"

Laela: "Good boy. We will e-sign the contracts tomorrow. I'll mail them over. I need to start knowing you better. It's better we start talking now. Share your personal number now. "

Me: "Yes mistress. Here is my number : @#$_$23##$."

Immediately I received a phone call. It was from Laela.

Laela : " I'm starting to trust you already my pet. Now to know you better"

Me: "Yes Mistress"

Laela : "To break you physically I need to know what your previous experience of domination play has been with women. When your ex girlfriend wanted you to top her, what did you do?"

Me: "I would get her forcefully on her fours, hold her pony tail back and then fuck her till she orgasmed."

Laela: "That's what guys do every day. What did you do to show that you dominated her? And don't make up stories my pet. The truth."

Me: "yes mistress. That was about it. She was not comfortable with anything else."

Laela: "Hmm. I see. What did you want to do though?"

Me: "Lot of things actually. Fuck her throat until she gagged. Fuck her ass maybe. Tie her up & then fuck her. Cum in her mouth forcefully. Make her swallow. She was terrified by cum & never allowed me to cum outside of her pussy."

Laela: "Interesting to see that your brain observed use of force as assuming a dominating position. Your psyche thinks that a partner who eats your cum against their wishes is subservient to you. This is pretty normal. What is it about force feeding cum into a partners mouth makes you feel dominant?"

Me: "Maybe the fact that they have to do something I tell them to do no matter they like it or not."

Laela: "Hmm. What if your sub liked being deep throated & guzzling cum? Would force feeding them make you feel dominant?"

Me: "Maybe not."

Laela : "How would you dominate your sub then?"

Me: "I don't know. I've not thought about it. I don't think there is an easy way."

Laela: "Ok. How about this? Let's say you came on the floor & told your sub to clean it up. Would that make you feel dominant?"

Me: "That's gross. I would not tell my sub that."

Laela: "Hmm. Wouldn't an obeying sub do anything they are told to?"

Me: "If you put it like that. Then Yes."

Laela: "Let me list a few things here. Tell me whether you would feel gross in each of these situations

1) You cum on the floor, toilet seat, or a wall & ask your sub to eat it up.

2) You make your sub cum every time into their mouth so that they recycle.

3) You top off anything they eat or drink with your cum. Only then they get to have food.

4) You take your sub to a public glory hole and force them to feed off cum from several strangers."

Seeing these texts sent my brain into a tizzy. All of these were too extreme & I'd never imagine telling someone to do it, let alone me doing something like that.

Me: "Yes. All of these are gross. I'd never do that to my sub."

Laela: "What if I told you to do it as my sub?"

Typically, I would have panicked. But the thought of having Laela feed me her cum did not repulse me. I was amazed by the fact that even the thought of having to feed off cum from several strangers at a gloryhole did not turn me off. As long as Laela was there with me to feed me cum, I was Ok doing it.

Me: "I'm surprised by my cocks reaction to your suggestion. My brain is saying no, but my cock says otherwise. I don't understand"

Laela: "That's probably because you have already started to trust me. And also because you secretly wish to be a cum guzzler. Tell me, have you ever tasted cum?"

Me: "Yes. I once jerked off into my mouth. Didn't like the taste"

Laela: "That's because you ate cum after you had an orgasm. I'll make sure you do it before you have an orgasm. Then you'll love to enjoy the different flavors and texture semen comes in. Oh, I have so many things to do to you. "

Me: "Anything for you mistress!"

I was feeling so slutty then.

Laela : "Anything?! Be careful pet"

Me : "Anything for you, mistress!" I repeated myself, wanting to show my obedience. For the first time I felt so comfortable sharing my world openly that I was willing to do any thing. Even if I would be repulsed by it.

I almost blew my load reading her text.

Laela: "Anything! Hmm. Consider this. I'll have you come over to my place in the next 1 hour. I'll strip you down naked. I'll collar you with a leash & chain, put a bitch mask on you, and tie you up to my bed. You would be on your fours and spend the night without food and water at the foot of bed until the next morning. In the morning, I'll set out a bowl of breakfast with dog food for you. And as you feed from the bowl, to prevent you from choking on the dry nuggets I'll dampen the food by peeing into the bowl. And then empty my hose into your mouth. We'll repeat that through the day with a few changes. How about that?"

Laela peeing into my mouth & being her literal bitch for the day turned me red with anticipation. This was way beyond what was acceptable to my logical brain. But my desires and kink seemed far too deeper than I ever thought were. I was actually excited at the thought of Laela emptying her bladder into my mouth. My mouth was salivating at the thought. I was imagining opening my mouth wide in front of her flaccid 5 inch cock & a jet spray hitting my mouth & back of my throat and into my belly. I would then lick her tip off to prevent her from soiling her clothes. I would then proceed to suck her off and make her cum in mouth. As these thoughts crept into me mind, a voice inside my head told me I was a certified slut. Without giving heed to my inner shame & guilt, I wrote back.