My MtF transition experience has BORED me, and I find being a girl. and an escort ..as I am now...disastrously frustrating. I like the way I was -- dressed up as a girl to find sex at night and yet working at day as a male teacher giving lessons to boys. That unfortunate incident of my being caught for embezzlement has cost me my cock and, what is worse, the immeasurable happiness I found as a crossdresser.
Now lying in bed all naked...as a girl with a pussy...awaiting to be fucked by any man/boy who has booked me...I am still thinking of de-transitioning from girl back to boy, or less pretentiously...at my present age...from woman back to being man. But as I look down at that flat pussy with a neatly cut slit in between my legs, I can't help missing those days when my cock was still there. The fact is that however dysfunctional or softly small a cock is, it is a much needed organ for retaining the sort of freedom enjoyed only by men, and permanently denied to women.
With a cock on, I don't need to line up at female toilets to just pee, and when I urinate, I could if I liked choose to stand to pee, whereas now, as a girl, I MUST sit down to pee. If you are a man, there is nearly no danger at all that you maybe raped at a back street at night, but as a girl...as I am returning home from an outcall...I have been raped on the street in pitch darkness many times over.
When the fire of passion gets all over me at night, and there is no man, no client, no boy or anybody of the male gender around, my body keeps burning hot like fire all over, and masturbation won't help. In my days as a crossdresser when I still had a cock, I could just masturbate, and although my penis couldn't really get hard, I could after a struggle cum...and then there was that release from the TENSION building up inside my body, as it is now even as I am typing out this particular article.
My dream time...that wonderful time...when I was a crossdresser is now sadly gone, and I miss it from the very core of my being. There is nothing I can do about it now, since now my cock is gone, and I actually have no hope of going back to being a male, getting back the freedom that I so dearly miss. Being a girl makes me look pretty...and cute too...but this physical condition, being without a cock, and so vulnerable ...is frustratingly constraining, to say the least.
Physically there is no way for me to be a crossdresser again, but the memories of my good old days as a crossdresser linger in mind, and in the quiet of the night, when I suddenly wake up, I miss that experience. This is the experience I want to share with you if you care to read about it.
After months of unemployment following my graduation from university, I successfully got a job as administrative assistant at an import/export firm.
I had to falsify my medical reports to prove that I was normal like any other man to be able to get that job --as the fact that I had breasts would prevent me from getting any decent job, which normally doesn't accept ladyboys as applicants. I was in charge of the accounts department, and in my desperate need to make myself prettier, I juggled the account figures to steal some company funds for my personal use.
I was therefore able to buy lots of pretty clothes, and very expensive female hormone pills, both of which made me look very pretty and impressively shapely when I crossdressed as a girl at night in search of sex with men on the street.
I started taking foreign trips, because once abroad, I could freely put on girls clothes to walk out onto the streets even at day, without the fear of being recognized by anybody who might know me as a boy/man.
In those wonderful months when I stole plenty of money from company funds I took numerous trips abroad, to Singapore, Hong Kong, Shanghai and even New York. I liked travelling to places with a winter, because in wintertime I could dress myself up most prettily in beautifully designed and patterned thick woolen winter clothes which are so very colourful. Furthermore, once in a big overcoat, I needed not put on anything beneath it, and that all-enveloping overcoat was just too perfect for having public sex when I cross dressed in foreign countries.!!
(If at any time you happen to see this blog of mine, do read about my MtF transition in a separate, related blog here under my name, Jennifer Yvonne Lee. My Google + profile has been permanently suspended...for indecency... so you will NEVER be able to find my Google+ profile anywhere.)
Picture 1 Below : I was a crossdresser until March 2013. I graduated with an honours degree in history and literature from Universiti Utara (Northern University), which is just off the Malaysia-Thailand border.
I was brought up as a girl by my stepfather who had had sex with me since the age of 13 when he found out that I liked crossdressing as a girl to go out onto the street at night to have roadside public sex with men.
Upon graduation from university, I worked as an administrative assistant at an import/export firm in Malaysia and was caught by the manager for having embezzled company funds which I used for buying jewelry, clothes, female hormone pills and skincare products.
The manager took me to his home where he stripped me naked to check if I hid any money I stole in the pockets in my shirt and trousers. He found no money, but he did find that I had small breasts, soft white girly smooth skin and a small cock with a weak penis that was limp to the point of not being able to get erect even when stroked hard.
In return for not pressing criminal charges of forged identity (I disguised as a man when in fact I was a shemale) and embezzlement (I stole about USD 50,000 from the company investment funds), I agreed to feminized to be a female slave of the manager who is now my Master.
As you can see, my chest was almost flat in those early days in March 2013, when Master and His friend required me to play 3P with them.
Picture 2 Below : At the initial stages of my feminization training, I had to get used to being fucked and caressively touched by men without getting hard myself.
It was hard for me to do that as when I was a crossdresser, I often got hard while sucking a man off or being penetrated in my asshole. Getting hard while being used by men like a girl became part of my natural reaction...almost involuntarily...while having sex with men.
So whenever I got hard, Master and His friends would not hesitate to use the greatest force possible to press and squeeze my hardening penis into a limp lump. Or if that didn't work....which meant my penis kept getting hard....I would need to get down on my hands and knees with my butt raised way high to be spanked or caned by Master - for getting hard without permission.
Picture 3 Below : Towards the end of October, 2013, Master found that despite having me disciplined with the whip or the cane, my penis was still getting hard without permission. I myself tried my very best to hold down my penis while I was being penetrated by men, especially when the man happened to be Master.
But still, that hardening process continued. I was taking female hormone pills on a daily basis but the secretion of the male hormone testosterone from my testicles, my balls, effectively prevented significant progress in my feminization : My breasts as you can see remained unsightly small by normal female standards, and my penis didn't retract to become small enough to acquire that cute, docile look that the men in my part of world like.
So eventually Master decided that He must send me to Bangkok, Thailand for my balls to be cut off. In that way, my male hormone manufacturing centres, my testicles, would be completely destroyed in one single cut. I would be left with just a penis which could never become erect again. My penis was expected, as the Thai doctors said, to retract significantly to become much smaller and weaker after my castration.
Yes it could be FELT to be getting hard when stroked, but it was just a hardening process that couldn't translate into an actual, visible erection in that normal, male way which I used to show before my testicles were cut off.
Picture 4 Below : Two months after my castration, Master sold me as a slave /submission escort to a night club in Thailand for a period of two years.
My penis was, as expected, even then shrinking into size from tip to root, both in terms of length and width, retracting to just about two inches when clients poured icy cold water onto it to to make it retract and contract to the smallest size possible. This was how my body looked in February, 2014, two months after the cutting off of my balls.
Picture 5 Below : When I was a crossdresser, I didn't usually have anal sex with men. Most of the men I picked up on the street tended to be a bit scared about having me fucked in my asshole - for fear of contracting an S T D, or sexually transmissible disease.
On most occasions I just got down on my knees to suck a man off at a street corner -- under cover of darkness. Most men would like me to pull down my panties to take a look at my butt, but when they saw that my asshole was so very small, they were discouraged from having me penetrated there, for fear of being not hard enough to sustain a credible penetration. A few men did try, but because of the tightness of my small asshole, they just succeeded in exploring the perimeter of my asshole, just at the part where my asshole folded together.
When I first underwent training to be a shemale slave, Master often punished me for disobedience by having me PAINFULLY dry fucked, meaning that He penetrated me without first having my asshole lubricated. When I gradually became more obedient and cooperative by having my asshole spread wide open with both my hands, Master started lubricating my asshole with olive oil before having me fucked. The smallness of my asshole did cause many problems to my students who started coming to have me booked in their hundreds after my castration.
Eventually the night club manager to whom I was sold solved this 'small asshole problem' by requiring me to insert a butt plug into my asshole at least two hours before I am (still am) fucked in my asshole. The butt plug serves to loosen my asshole sufficiently....making it larger...so that when the boys come to have me fucked, they can more easily enter me without suffering the embarrassment of not being able to enter me because of their not being hard enough.
(Pictures Below : When I started working as a castrated shemale escort in January 2014...soon after my castration in December, 2013...I didn't like having a big butt plug inserted into my asshole as preparation for my being fucked by my clients, 90 per cent of whom were my students.
So during the first two weeks of my work, NONE of my students succeeded in penetrating me because my asshole was just too tight. A big naughty student...who I often punished by being made to stand in class...forced me to turn up my butt...so my asshole was exposed in full view...took the following two pictures....to show how small my asshole was to the night club manager.
Consequently, the night club managers asked my boys clients to gather together...initially just 20 of them...so they could see me kneel down to apologize to them for having such small asshole -- and then I was told to push the butt plug into my own asshole to loosen it in front of them. That was so shameful...my face got all red...but the boys clapped their hands in applause and approval. I had to say this to express my apologies : "I am so sorry for having such a small asshole..I'll make my asshole big enough for you next time. If it is not big enough, please whip me... very sorry Sirs !!"
Picture 6 Below : Soon after my graduation from university, I was unable to find a full-time job as a teacher because I couldn't even hope to pass a bare-chested X-ray medical exam with me being stripped naked above the waist.
I had grown breasts and if found to be a ladyboy, I wouldn't qualify for any full-time teaching post. The government here won't employ transgender people as teachers. I had left my stepfather's home because he said he wanted to send me to Thailand to work as a ladyboy escort. I believed that with my university education, I should qualify for something better than that. But I soon used up all the money I took with me when I left Papa's home and I had to sleep rough on the streets, mostly at public parks.
One day, a girl classmate mine met me at a public park. I told him what had happened and revealed to her my ladyboy identity. She said that was okay...she would take me in at her rented flat in Kuala Lumpur. She said, 'It is all right...I let you eat nutritious food and soon your penis will get strong again.'
So we lived together after that....we had lots of sex...but sort of lesbian style, with my girlfriend sucking and stroking my penis -- and me touching her breasts and butt.
But despite the fact that I took no more female hormone pills and I did lots of dumb bell exercises to make myself more 'man', my penis just couldn't get hard. My girlfriend was disappointed...she tried and tried...stroked my penis for hours at times...but still I couldn't get hard.
She suggested that I should cut off my breasts to look more normal. But I flatly refused that, because I loved having breasts and after all, it really took me lots of time to grow my breasts. Cutting them off was out of the question.
So eventually we had to separate. Before she left, she gave me lots of her pretty dresses, skirts, heels, bras and panties saying that I indeed looked much nicer in girls clothes.
Picture 7 Below : I was taking heavy doses of female hormone on a daily basis while I was at the university. One effect of taking such heavy dosage was that I got sooooo very hot, so that I sometimes ventured to go out ...in girls clothes...onto the street even at day.
Once I went to a construction site near my university hostel. It was a public holiday so the construction site was nearly deserted. But there were two or three workers around, and from the way they dressed, one was an engineer, one was a foreman and one was a general worker.
I went into the site....told the engineer what I was...and expected him to turn me away. But to my surprise he said that he would very much like to have me fucked, even though I had a penis, and he invited the other two men around to have me gang banged.
I told him that I couldn't deal with three guys at the same time, because it was a daytime -- what if the police came ? The engineer assured me that it was okay...the police never ever visited the site.
Not only that, the engineer phoned another engineer from another site just nearby to come so someone could hold the camera while I was being gang banged.
I found ALL the men at the construction site so very strong, because most of the men I picked up at night couldn't get hard enough to penetrate me in my asshole -- but all these guys could, and each one stayed inside me for at least 15 minutes.
The picture below showed how a general worker, the bald-headed man, was stroking my penis while the other two guys were stripping me naked ---with another man holding a camera to take a video of what was happening to me. The general worker's hands were very coarse and rough, and caused my little penis to fell very itchy while he was stroking it.
Then I saw the bald-headed man unbutton his flay...took out his rock-hard penis, which then he shot out a jet stream of cum that travelled in mid-air, in a sort of curve, for at least two feet behind it landed on the soil.
The four guys took turns to stroke and squeeze my nipples and penis, until I FELT my penis get hard...which it actually didn't because it just couldn't...but I leaked out a few droplets of watery, runny-egg-like cum anyway -- the guys clapped hands, saying 'Good girl' and patted me on my head.
The guys said that my skin was soft, white and pretty and, after they had had me fucked, asked me how much I would charge them if they wanted to have me booked next time.
I told them I was just a crossdresser....I did all this public sex for pleasure, not for money. They kissed me on my tits, saying 'thank you' when they left me to get dressed behind a wall.
This is the 'fuck room' at the night club at which I work. It is lavishly furnished with carpets here and there, both on the walls and on the floor. The overall atmosphere is pinkish and erotic, with a touch of the romantic bedroom designs used by Turkish sultans in the bygone days of the Turkish Empire.
Like other escorts, I need to strip myself naked as soon as the time for an appointment begins. I prefer to take off my clothes at the very last minute as the room is kept cold like a refrigerator at a consistent 14 degrees Celsius. Some clients, especially the mature, middle-aged ones, would prefer to take off my clothes with their own hands, but young clients like my students would prefer to have me serve them all naked as soon as they enter the room.
In the drawers of the closet placed again the wall are stored various discipline and bondage devices like the collar, the whip, vibrators, nipple clamps and so --to be used on me...and other escorts...as and when the clients wish to.
The carpet at my back covers a doorway leading in a zip-zap way to a hidden underground cellar where clients may punish me by having me put on a forced orgasm machine....or have me subjected to suspension whipping (very painful !!)...in case I am found to intentionally or unintentionally disobedient or impolite to them. Sex work is work, but it is really very humiliating work -- to the nth power by any normal standard.
When I was a secondary school teacher, I often scolded my naughty boy students for disobedience, especially when they chatted...boisterously...while I was teaching them. Now that I am an escort, my boy students keep coming to have me booked -- with a vengeance. They think that I was just too 'loud-mouthed' when I was a man and a teacher, and that I should be taught lessons as to how to behave as a soft, gentle and QUIETLY obedient girl.
I beg them not to have me punished, but the answer is always that if I could stand to pee...the ways men do...they would let me go unpunished. I keep apologizing but that basic requirement....standing to pee...I just can't do it, at least not in the way men normally do. I can just manage to stand peeing with my legs awkwardly spread out wide, and ACCURATELY hitting the urinal with my urine... or anything placed on the floor in between my legs...is 100 percent impossible because....because...my penis has already been cut off...for disobedience...by Master.
So I have to obediently get down on my knees to accept, as the boys say, my well-deserved punishment -- on my mouth--because I was just way too mouthy and loud-mouthed when I was a male teacher.
One of the most painful punishments I normally receive is to have my tongue clamped with a clothes clip. When I was an English teacher, I often had the boys punished for mispronouncing certain English words. Now that my tongue is clamped with a clothes clip, they ask me to to pronounce multi-syllabic, tongue-twisting words like 'responsibility' and 'humiliation', which I often unfortunately sort of slur or babble through as I just can't twist my tongue while trying to read out the word. That gives the boys an excuse to punish me further, which consists in requiring me to eat their cum and/or drink their urine, which they shoot direct into my throat. As my mouth is kept wide open by the clothes clip, the cum/urine shot down my throat easily has me gagged, so that I cough uncontrollably.
To avoid having such punishment being unnecessarily prolonged, I normally choose to voluntarily take out a table tennis bat....hold it in my mouth...crawl on my hands and knees at...and around... the feet of the boys...and then BARK like a puppy, with my head nodding every now and then. The boys would then take the table tennis bat from my mouth and have me spanked butt bare for five minutes. I notice that they can always sustain a long, rock-hard erection...and have me penetrated long and hard... after having me punished in this way -- and they are normally so satisfied that they generously tug stacks of banknotes (equivalent to about USD 50) INTO my mouth as tips for my 'good service'.
Once, whilst in senior secondary school, I wandered off, in girls clothes, to a beach near my home. The beach was deserted with nobody in sight, so that all around me I heard only the distant sounds of receding waves, and the whispers of winds that blew over my body, lifting up my skirt like a balloon, so that I felt so excited, because the light sea breeze somehow got my small penis a bit hard, which otherwise it wouldn't despite my stroking it repeatedly in the loneliness of the night.
Then I saw a much older man in his late 60's appeared on the far horizon, and as he came ever closer, I noticed that his hair was all white, and was apparently harmless.
I lifted up my skirt and told him that I was a boy, a crossdresser looking for sex with men. The old man seemed very interested, and then he hugged me, stroking my breasts with his big hands, a bit rough yet so comfortable.
Then in the midst of his stroking my nipples, a young boy appeared from behind a beach rock...it was his son, and the old man said, 'Hey, son here a pretty girl with a penis...you like to try her.'
The boy hesitated, but extended his hand to touch my penis beneath my panties, already pushed down to my knees by his father. The boy murmured to himself, 'Yes very small penis...skin so white and smooth.' Although outwardly I appeared shy, closing up my legs to get my small penis hidden, I was so very glad that I could hitch up with those two all at the same time.
I knelt down at the feet, begging them, 'Please be gentle...I just want to be a girl, like any girl.' 'Why do you want to be a girl ?' the boy asked. I said, in my trembling voice, saying, ' Papa treats me like a girl a home...so I want to be a girl.'
(Me - Being fucked by a 65-year-old man at a deserted beach, with the fine beach sand as my bed. The old man said that my skin was very white and smooth, like a girl's, and that made me so glad, because I really wanted to BE a girl.)
With that both father and son smiled, and they took me behind the beach rocks, had me stripped naked, and there beneath the setting sun, they took alternate turns to have me penetrated in my mouth and asshole.
As they were leaving, they gave me their phone number and asked me to contact them again for sex. But I threw away the little piece of paper with their phone number on, because it was never safe to have sex with the same men for a second time, when they might bright along someone who could be well prepared to give me a hard time - or beating - something I did experience some time ago.
(Me - Getting down on my knees to get ready to suck the boy's penis, and this kneeling down at the feet of a boy younger than me by at least five years made me feel so inferior, and in my inferiority and submission, I felt paradoxically sooooo feminine, so very girl)
Crossdressing is obsessive-compulsive in nature, in that when that inner urge surges up one's brain, a sort of biochemical reaction occurs in one's brain, which simply FORCES one to put on girls clothes, put on girlie makeup and get into heels.
There were times when I resisted that kind of urge, because it was too strange, me being forced by it to put on girls clothes, and then I stood in front of a standing mirror, admiring my own femme persona, though to be frank, that girl image in the mirror of mine was NOT necessarily too pretty because in my crossdressing days, I didn't rigorously follow strict hormone treatment, me randomly taking estrogen pills as and when I felt like it. As a whole, I was NOT looking too pretty...sort of like a sissy boy when in girls clothes...and could still be easily read as a boy at day, though at night I should be passable with a bit of makeup and skin whitening.
That absolutely irresistible urge came punctually in the small hours of the morning, in between 2.30 am and 3.30 am. I startled up...literally flushed out...from my sleep...then as if mesmerized, I searched frantically for bra, panties, skirt and blouse to put on.
That urge was so strong that I really spared no time in making myself pretty or passable because I MUST be out on the street just to walk around as a girl...in minutes... not necessarily to find a man to have sex with, but just to give liberation to that female persona of mine, so that SHE could walk free from the harness, the prison and the chained compression of that male hulk of mine, which I didn't really like, but which I had to accept because of the way I was born with it, penis and all.
In the darkness I wandered aimlessly, and if I happened to see men...lone men walking all alone by themselves...I would approach him, asking if he wanted to have sex with me while lifting up my skirt...revealing my small cock...for him to have a look.
Some men were just scared off, but up to seventy percent of the men/boys I met up with showed interest, not necessarily to have me penetrated in my asshole, but just to ask me kneel down at their feet to suck their cock.
In the darkness, they liked pressing my head down, so their cock could penetrate my mouth deeper...down to the top of my throat; occasionally I got gagged, and then I coughed, and as if boosted up by a sort of sadistic satisfaction, the man's cock usually got even harder as a result of my coughing.
I did that mostly at street corners, but a few men took me home to have anal sex with me, but that represented less than 1 per cent of the men I picked up on the street in the course of my decade-long crossdressing adventures in the middle of the night.
Me : Doing 'penis sparing', sort of like a sword fight, by having my small penis sandwiched in between a man's thighs, so that his much bigger penis touched mine, and mine his, creating through friction a sort of itchy sensation that fired me with passion, while making the man very hard indeed.
As I said, in my days as a crossdresser, I was not taking female hormones regularly, and my body was NOT neatly feminine, but passably soft and white - for a crossdresser.
Occasionally, men liked having my small breasts pressed down and flat, so that beneath the tight belt on my chest, with my breasts pressed really low and flat, I had a perfectly flat male body with a flat male chest illusion.
For some men, they NEEDED to make my body look like this...looking male yet feeling soft because of my smooth skin...and then they could get aroused and get hard enough to penetrate me.
I found men who would like to do this with me basically gay, and were not really interested in ladyboys, T-girls or shemales. Anyway, I DIDN'T look too pretty , and I just couldn't pick and choose who to have sex with, and as long as there was a boy/man around to satisfy that irresistible urge of mine, it was okay with me.
While in matriculation class, I became the sex slave of three of my schoolmates who knew about my ladyboy identity. As the school administration would expel ladyboys from school for moral indecency, I had to satisfy the needs of those three schoolmates so as to keep their mouths shut about my secret, which was that I had breasts and was taking female hormones to feminize myself.
My three schoolmates had poor high school certificate exam grades and were unable to get qualified for matriculation. But that didn't mean that they would release me from my bondage.
After school, they would require me to meet them at specified locations which were usually rooftops or some isolated, deserted staircases.
There they would require me to suck them off, and while I was sucking their penis, they would caress my breasts. It looked kind of odd, that a boy was sucking the penis of another boy out there in public. But I must do that or they would report my case to the principal in which case I would be expelled from school, thereby losing my chance to go university.
So throughout my matriculation year, I slept with them as required, and got spanked on my butt if they found that my skin was not white and smooth enough to arouse them.
Whilst at university, I liked crossdressing at night...in between 1.30 am and 4.30 am...at a red-light district near the university campus. I whitened my skin as much as possible, often simply by applying whitening powder all over my body.
I stayed well off from those ladyboys who were real prostitutes, preferring to loiter at rather secluded locations several blocks away from a night club where most ladyboys were concentrated.
Because of the remoteness of the location where I was usually at, I picked up no more than one man every two weeks, and I often got him hooked up by offering to allow him to have me fucked at a cutthroat price of just USD 2 per half an hour. My aim was not to make money but merely to get that most thrilling experience of being treated...and fucked...like a girl.
The men I picked up liked to take me up to a room at a low-budget inn nearby, and although much of the time the man would pay for the hourly room rental, sometimes I paid that myself, because I was so hot with passions and couldn't afford to lose the man who I picked up only with such difficulty as sometimes getting down on my knees at a street corner to beg him to fuck me like a girl, because as I often told the man, I so very much wanted to be treated like a girl.
When at the room, I would take off the rope that bound up my small cock so the man could twist, turn or pull my penis as he liked. But MOST men just liked looking at my small 2-inch penis, but would NOT touch it. Most insisted that I must get down on my knees to suck off their penis first, and I would then be penetrated, usually from the front, and very seldom from behind, as you might have thought.
(Me : Being ordered by one of my students to lick his feet on 3 March, 2014, three months after my castration.)
After I had licked his feet, I was told to stroke my castrated penis while being on my hands and knees. My student told me that if I didn't get my penis hard in 15 minutes, I would have to lick his feet yet again.
His feet were very foul-smelling, so I tried as hard as possible to get my poor little penis hard. But it just didn't get...in fact after my balls had been cut off...my penis just couldn't get easily turned on, the way it once did, and it seemed to get hard all on its own, and I couldn't get it even a bit hard anyhow.
So after 15 minutes of unsuccessful stroking, my penis remained soft as ever, and I had to start getting my head way down to the feet of my student to have his toes licked again and again.
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