While crossdressing as a girl, my prime targets were CONSTRUCTION SITE WORKERS, because their penis was usually soooooo strong...with enormous staying and sustaining power when in erection...and their hands were so very coarse, and that coarseness, like sand paper, caused an unspeakably soothingly great pleasure they they were gliding, touching or squeezing my soft, white skin -- a titillatingly tingling sort of feeling hard to matched by the hands of men doing other jobs. Whenever I entered a construction site, I made sure that no more than two workers were around at any spot, for I could not possibly handle too many men. Those men were always will to have sex with me provided that it was FREE, and in that way I got the satisfaction I craved for, and I felt so happy when they said that my butt was pretty, white and soft.
In general, construction site workers were rather SHY, because they were rather poor. The first reaction when I approached them was that they told me direct that they had not money. When I told them I would do it for them for free, they were still not too interested because in my days as a crossdresser, my female hormones intake was irregular, sort of D.I.Y., or do-it-yourself without medical guidance, so that I did NOT look too pretty.
But this magic always worked...I pulled up my skirt, and beneath it I wore no panties, and then I let them see my clean-shaved, bald little cock with my very small 2-inch-long penis, and my legs were were so slender and white, with the soft lily white skin of my thighs putting my brownish but docile-looking penis into sharp focus.
THAT in eight cases out of then caused the men who saw it...my cock...to have a raging erection. In many cases I purposely walked off and away after I had exposed my cute little cock for those men to see, and they literally RAN after me to ask to have sex with me.
But there was indeed a small problem. Their penis was so very hard, and big, so that I coughed violently as it never seemed to get soft even after more than 20 minutes after it had been pushed...almost brutally...into my mouth, and the skin on my knees caps really hurt since their staying power was so good that I had to kneel on the ground...sandy construction ground...for over 45 minutes...kneeling and being choked...and just couldn't leave until they allowed me to do so.
Perhaps you may not understand this, which is that as crossdresser, my greatest pleasure was to have succeeded in luring...tempting or inviting, say what you may...a man/boy to unzip his fly ...take out his penis... and then to willingly and urgently allow me to suck him off.
Each sucking off experience vindicated my SUCCESS as crossdresser, because HETEROSEXUAL MEN WOULD ONLY INVITE GIRLS TO DO THIS KIND OF THING TO THEIR PENIS. Therefore, I so very much enjoyed getting down on my knees to suck men's penis, although the look of it...me being naked on my knees with the man being in the full dignity of being fully clothed, standing above me, pressing my head and mouth onto his penis...did look sort of embarrassingly awkward, if not humiliating by normal standards.
Yet that was my major activity in my days as crossdresser, roaming the streets in the darkness to literally BEG men to take out their penis to let me suck it. You have to read these lines to really believe that a person such as me could have ever existed in this world, and yet that was what actually happened...what I was so very much interested in doing...in those bygone days of crossdressing.
As a crossdresser, I collected over a period of over ten years a large number of bras of various designs. By my last count just before my MtF transition ...in March 2013...the numb,er of bras in my wardrobe amounted to over 200.
I bought some... at about 40%... with the money I saved from from my university scholarship...given to me by the Malaysia government because of my straight As matriculation result...and the rest of them at nearly 50%...I STOLE them from the women and girls living in my neighbourhood.
Most of the terrace houses in Malaysia have low fences, so that climbing over them to steal some clothes isn't a problem, and few people do that anyway because there is no market for old, used clothes. But the bras that the women and girls in my neighbourhood are of most attractive colours, designed and patterns. There were of different cup sizes, ranging from B to D++, but that was no problem for me, because I just wanted to get that exquisitely comforting, most soothing, feeling of having bra on. I got my bra on even while I was going to school, just beneath my shirt, and naturally I did that most often at night.
This was me, at the age of 13, when I started crossdressing as an obsessive-compulsive habit.
It was hard....excruciatingly hard... for me to pass even one single day without having spent some time...even a few minutes would do... on admiring myself...my image in a the mirror...and that girl with a beautiful me in a wig and some fashionable, colourful female clothing is THE holy grail I must seek out daily.
There was this great unease, a sense of not being in the right place, if I didn't put on girls clothes for at least 15 minutes at a certain time of the day. It might be done early in the morning, late at night, or even in the afternoon.
I was UNABLE to get hard in practically all situations, even after watching porn videos, because I tended to think of myself not as the boy having a girl fucked in the video, but as the girl being submissively fucked.
And then when I was in bra and panties...my mother's lingerie...I got so turned on when looking at my own image in the mirror. Oh yes indeed, my skin was so white, so smooth, and the sexy lingerie I was in made me look so pretty. And then up...up...and up...my soft penis got awakened, as if from an intensive dream, and it almost suddenly hardened to to form a rod, not necessarily rock hard...it never was that hard...was hard nevertheless because it was able to get erect.
I made it a point NEVER to do chest-expanding exercise...the way most boys did...and that kept both my shoulders and chest small enough to enable me to put on my mother's close-fitting clothes.
See, how FLAT and SMALL my chest was, and in those magic moments when I was captivated by the beauty of my own body, I put a black/red bra onto my chest -- the sexy-looking bra, like a magic wand, helped highlighted the whiteness and smoothness of the skin at my shoulders and chest, and so I was turned on yet again, and in such monitored, carefully paced routines, my penis was finally able to get hard enough to cum.
After I had shot my cum loads, I took off my girls clothes....and then I was able to lie most peacefully in bed, usually all naked, imagining in my own way I had just been a girl who had been fucked hard by a man.
A successful crossdressing adventure out on the street in the darkness of the night can NEVER have a successful conclusion with having a sexily designed bra on.
At any time before my formal MtF transition in March 2013, my breasts were never big enough to prop up even a B Cup bra, but I often had a D Cup bra on while going out in girls clothes. I had a tight string tied at the base of my near-male-looking breasts, so what little flesh there was in my breasts was pushed up by the binding pressure from the string and then my breasts would stand up firm, the way female breasts normally do.
That D Cup bra I had on was to give any man I met on the street that attractive, large-tits-no-brains vulnerable little girl illusion. In the darkness, under the dim street lights, the man would normally push or slide his hands, usually both, into my unbuttoned shirt, and they would push up my bra to squeeze, touch or caress my breasts.
When that was happening, it did NOT matter whether my breasts were really that large, for as long as the man's hands felt something soft and smooth at where my propped-up breasts were, they would get their needed erection to have me penetrated, usually in my mouth, but rarely in my asshole as 90 per cent of the men I met on the street were afraid of getting infected with a sexually transmissible disease, or STD, from me.
Crossdressing was a dangerous...very dangerous...activity, because it involved me dressing and making up as a girl...with wig, girlie lingerie and clothes...and then I needed to venture and wander around at dark streets to find my games, men who would like to have sex with me. I might get arrested by the police.
Sometimes I went into the lift of an unguarded building at 3.00 pm, and there I stood inside the lift, allowing it to take me up and down half a dozen times. If there were people using the lift during those hours, they had to be men, because women and girls normally didn't dare to venture out so late at night.
If the man who was in the same lift as mine was to my taste, I would tell him WHAT I was by lifting my skirt to let him see my small cock. Normally, men would like to do something with me during such small hours of the early morning, because the chance of their being caught was zero. If somebody came around while we were having sex, we could just close the lift door and escaped. The lift was big enough for the two of us, though it got a bit packed if the man was a large one. I liked men to say that I was pretty, and I was delighted when they said that my skin was white, smooth and pretty. The lift therefore became a convenient vehicle for my nocturnal ego trip.
One of the most sexciting things I did while crossdressing was to urinate in public, at a well-hidden location behind trees or walls. But the spot where I chose to squat to urinate was carefully chosen so that there might just be somebody...a man, a woman... a boy or a girl....passing by.
I usually did this kind of public urination at a location near some isolated houses, where it might just be possible for someone to leave the house to do shopping at mid-afternoon when the streets are usually empty in the tropics. It didn't really matter if it was a woman or a girl passing by, in which case I noticed that they pretended not to have seen me butt bare urinating. The women and girls usually took quick steps and quickly disappeared from sight. Their apparent embarrassment THRILLED me in a way I could not describe in words.
And then when a man or a boy passed by, I would be a bit more audacious, purposely turning my bare butt in their direction, so that they HAD to be able to see me. Usually the men or boys paused, and instead of walking away quickly...the way women and girls did...they chose to walk off very slowly, turning their heads to look back at me every now and then even if they were already some way off.
Nobody ever approached me for sex while I was doing this kind of public urination. But it made me so very happy, being able to expose my pretty butt and lily white legs....with my skirt lifted up way high...while I was urinating for them to see.
While at university, I was getting ever bolder in my crossdressing adventures. Instead of sneaking out from the university hostel in the middle of the night...as I often did during my first two years there...I began venturing out as a girl in broad daylight, choosing to go out in the afternoon hours between 1 pm and 2.30 pm when the hot tropical sun makes the back streets and lanes as deserted as they are at night.
Once having found my favourite hideout, which was a back lane sandwiched between the back of a worn-out building and a high stone-paved wall, I stripped myself half-naked, and just stood there, waiting for a man, my target, to pass by. Sometimes nobody passed by even though I had been standing there for one full hour. But occasionally in three times out of ten, a man...or a boy...might pass by, and then I put on an overcoat, beneath which I was just in bra, panties and stockings.
I asked the man/boy to come into the back lane, and there in broad daylight, I took off my overcoat....pulled down my panties to show him WHAT I was....with penis, balls and all...and then he understood. Some men/boys just ran off, thinking that I was crazy, but about 40 per cent of the men/boys I met up there chose to stay behind, always asking me to give them a blow job. Eighty per cent of the men left in a hurry after I had sucked off their penis...with their cum having been shot onto my face...but a small number of men/boys were brave enough to pull off my panties and stockings to attempt to fuck me in my asshole.
Because it was in precariously broad daylight, and because my asshole was really very tight and small, NOBODY succeeded in penetrating me in such situation. Most just explored the outer perimeter of my asshole, starting to cum upon first contact. But that already made me feel so happy, and my long march to become a girl had taken a big step forward because of such AUDACIOUS daylight adventures.
At the age of 17, I was simply addicted to crossdressing. I viewed it as a liberating activity from which I got the strength and will to live on as a human being, because my life as a boy was so very meaningless and outright boring to death.
Near my home there was a construction site, and around the construction site rows upon rows of very shabby, dilapidated iron-plated houses were built to house the migrant workers who came to work as low-paid workers doing menial work that few locals were living to do.
After school while I was passing by those houses, I saw lots of dark-skinned workers lying or squatting there and there -- all so very strong and temptingly sexy the way their legs appeared, with lots of hairs and hugely muscular. Therefore in mid-afternoon, when workers either slept or went out to relax after their morning work, I slipped into a worker's uniform, a big overall, and went into the site to seek out my targets.
I normally approached workers who were sitting way outside the construction, and in pairs, and wouldn't approach any group exceeding three persons, for fear of unnecessary danger or harassment. Then seeing that there was nobody else around, I would unbuttoned my worker's overall...removed my hat to reveal my long midi-sex hair...and there under the sunlight, my skin was sparkingly white, and smooth as velvet, and then I approached the men...let them see my small small, neatly shaved cock...showed them my mini-sized docile-looking penis....and these acts of provocation never ever failed to get the men rock hard down there between their legs.
Then we went to a corner away from the houses, behind the walls of half-constructed buildings, and there we had sex, and there I got the satisfaction...that comfortable fucking by the very big strong penis of those workers...of both my asshole and my mouth.... and that was what I had been so much needing all day long.
(The construction workers were all so very surprised that although I was a boy, my skin was so smooth, soft and white. They couldn't resist the temptation of touching me on my breasts and my thighs, and I told them direct that I wanted them to have me fucked, because I was training myself to be a girl, and that at home I was raised as a girl by Papa. Normally construction workers didn't ask further questions, and most proceeded to take me to a hidden location to have me fucked hard....oh, their penis was so strong and long...nearly 8 inches hard for many of them....and I DID enjoy being fucked by construction workers.
Their skin was so dark-looking in its gross coarseness, and the darkness of their rough, hairy skin, when contrasted with the lily whiteness of my soft skin...without hairs...turned me on, sending pulsating vibration to all my nerves, stretching my feelings of exaltation to their maximum limits.)
Me : Getting ready to dress up as a girl for my crossdressing adventures at night.
I was in the final year of my B.A. (English and History) degree course. My earnings from working as a part-time teacher at a boys' secondary school had helped me to save up enough money for buying female hormone pills and pretty female clothing. My wardrobe by then had different types of wigs, skirts, stockings, heels and wedgers.
In this picture, I was using a special pussy lubricant to lubricate my asshole before going out at night in girls clothes. Lubrication of my asshole was a needed procedure before having crossdressing walks as some men I met up on the street might want to have anal sex with me.
Without sufficient lubrication, my asshole might be hurt by excessive friction with the penetrating penis which could be quite big if the man was an Indian. My breasts were comparatively small in those days...at just A Cup...and they didn't actually start growing until after i had been castrated by Master for disobedience in December 2013.
Because I enrolled in the university as a male student, it was not convenient for me to leave the men's hostel in women's clothes. So I preferred to put my female clothing...along with my wig...into a travelling bag, which I carried with me to an isolated location where nobody would recognize me even if there were people walking near me.
In the final years of my university studies, I got much bolder and ventured to do crossdressing at day, but normally in the afternoon when the hot sun of the tropics would keep most people off the street. Then usually behind a wall of a building situated at an isolated location, I would change into female clothing -- with particular emphasis on putting on a sexy bra with frills and nice, colourful linings.
I would stay put at that location to WAIT for a man/boy to pass by. I had found that I had more success with Indian and Malay men, and much less with Chinese men. That is not because Chinese men have no interest in ladyboys, it is just that the Chinese in my part of the world are richer than the Malays and Indians and they are all travelling in their own cars, and are seldom on foot.
As a crossdresser, although I had been having breasts for years, they were not immediately visible and needed minimal wrappings to simulate the flat male chest because they were comparatively quite small -- at about 33 inches, sometimes a bit more and sometimes a bit less -- but never more than that at any time before March 2013, when I began having injection-type hormones under professional guidance.
My small tits in my view in no way interfered with my crossdressing. When I felt that irresistible urge to put on girls clothes, I would tie a rope or a string very tightly at the base of my breasts, and that sort of forced compression pushed my breasts up and had them rounded, thereby making them more erect and bigger than they really were. Afterwards, I put on a bra with sponge paddings at both cups, and those two little steps....using a string to push up my breasts....and bra paddings...made my breasts look more presentable at an attractive measurement of 37-38 inches -- and with a clearly marked breast cleavage too.
If you are not a crossdresser, you will find what I did rather ludicrous, if not madness itself. But you have my obsession, you know very well that it is MOST important to have those nice-looking tits...real or fake... in place while in women's clothes, because those are essential baits for having men hooked in the darkness of the night.
My activities as crossdresser occurred mainly in the small hours of the morning, between 2.30 am and 4.30 am, for during those early morning hours, there are few police cars, if any, on petrol, so that I would be safe from possible arrest.
I had different types of wigs for use, from medium-length ones covering just my ears to long hair ones flowing onto my shoulders and at my back. I usually put a tight hair band on my wig, because it wouldn't look too nice to have my hair just dropped off while I was having sex with men. That never happened because of this tight hair band being on.
The darkness of the night was comforting and protective, because in the darkness it was I who took the initiative to find men, not men in police uniforms trying to arrest me for crossdressing. When I couldn't find a suitable man, I would just lift my skirt up at a dark corner...or just lay flat there...to masturbate until I started cumming. Or if I still couldn't manage to cum, I just squatted at roadside to urinate to pee like a girl to seek release from my tension.
Somehow, I could NOT cum by being just at my room...I needed to be in girls clothes to walk around a bit on the street to get myself hot enough to masturbate to orgasm.
The most suitable man should be somebody walking all alone without a companion, because I felt that I couldn't manage two men/boys at the same time. Once at the age of 15, I did hook up with two teenage boys at the same time. The two boys stroked my body all over...massaged my nipples...and finger fucked my asshole. All went on quite well until they for no reason turned on me, saying that a sissy like me deserved to be beaten up. And they started kicking me at my legs, and it was lucky that there were some houses nearby, and I rushed beneath the windows of one of those houses to seek protection -- so the boys had to leave, lest they should wake up the occupants of the house.
Since that unlucky incident, I never ever dealt with two men/boys on any one occasion. I often carried a travelling bag with, and in that travelling bag I put my male clothing. I left my house and district in male clothes...changed into girls clothes at a district where nobody would ever recognize me on sight to avoid such embarrassment as bumping by accident into a neighbour who might exclaim, 'My God why are you in girls clothes ?' That never happened because as soon as my crossdressing adventures were over, I went back home to my district in male clothing.
In the early morning, there was no danger at all for me to have sex with men just at roadside, and pictures were always taken of me as souvenirs by the man/boy who had me fucked. He kept one picture in his handphone and I kept one my own handphone, as a keepsake for memory -- and, please don't laugh, as my TROPHY.
As you might have expected, some of my nighttime activities took place at the male toilet. I never did it with any man at a toilet at a busy district. I chose a toilet at the suburban areas where few if anybody would ever use it. The toilet was most convenient for me because if the police did come, we ...the man and I...could easily hide in the closet behind close door.
As I always had all my male clothes ready for changing, I would immediately turned back being a man at short notice. There was no danger of my ever being arrested. I did fear such newspaper headline as 'Male university student arrested at toilet dressed as a girl.' That might mean that I could be expelled from university for moral indecency.That never happened, because I changed into girls clothes INSIDE the toilet once I found that a man was already there, so I could lure him into my embrace with my feminine charm. He knew what I was and what I was up to...no words needed to be exchanged...and things could get started immediately.
When it was all over, I changed back into male clothes and left the toilet as a man. On several occasions, some men actually paid me for my services, as they believed that I was a prostitute, and I played along by accepting the money, although as you see that was really not what I was going after at the toilet.
The country parks remained the best places to be for my crossdressing activities. There, my activities could last for a longer time period without any fear of possible police arrest. There are as usual urban services department garbage collection points at those country parks, and most are walled so that I could do what I liked with the man I picked behind those walls.
At the country parks, I could have sex with men at day, under broad daylight, as finding a policeman on petrol was next to impossible. My white skin looked brightly shining at day, and was irresistibly attractive to the lone morning walkers who usually felt free to do all sorts of things with me, as you can see here.
But more often I had to limit my activities to urban areas which were accessible to me on foot. Papa didn't allow me to learn driving, because if I didn't drive, I could be more easily confined to home.So much of the time I just took a long walk in the darkness into a wooded area near my home or university.
Fortunately there are plenty of heavily wooded areas in the region where I lived and/or studied. I changed into the sort of 2-to-3-inch heels I like (still do) as soon as I reached the wooded area of my destination, and there I sat at a bench to patiently wait for a man. And if I did see a man, and then succeeded in getting hooked up with him, that particular man was likely to be both wild and bold, because he too was certain that under cover of darkness and in such thick woods, there could not possibly be any policeman around.
So occasionally, he might just get so wild that he tore off some of my clothes, and the bra I put on was usually the first piece of garment to be damaged or soiled by such violent bursts of uncontrolled hot passions. But as usual although some of my female clothing might have been torn off or even shredded, my male clothes remained intact inside the travelling bag I was carrying with me. So I could also walk back home without showing any sign of having had such violent encounter with a man who literally turned into a hungry beast in the pitch darkness. Perhaps you may like to know that men treat all crossdressing males as 'girls', and as I served them so eagerly and obediently, they never ever had any intention of hurting me, as least that had been my experience and my own impression.
After having been fucked hard, I liked lying down naked on the ground in the darkness, between the double levels of a dark sky and an even darker earth, After I had sucked off a man and had been massaged/stroked at my breasts, my weak, soft little penis began to harden...it still couldn't get erect the way a normal male does...but it was hardening so I could close my eyes, recapturing...flashing through... the exciting moments when that man I just met had fucked, spanked or humiliated me, and then I would cum. If you are not a crossdresser you won't ever know why I needed first to be in girls clothes...and then be touched by men...before I could get a bit hard. Getting an erection may be easy for a normal man, but for a ladyboy like me with such a weak, soft small penis, I had to put on girls clothes to be fucked, punished and or humiliated by men...or even a little boy...before I could get sufficiently hard to cum to get the release I needed.
Ninety per cent of my adventures at night took place in wooded areas which offered convenient shelters for me to avoid possible police arrest. I noted that men were especially aroused by my lily white skin, so I took great care to keep my skin as white, soft and smooth as possible. At day I never went outside without an umbrella to shield myself from the skin-darkening uv rays.
Second, they liked me to have a small, bald, cleanly shaved cock. Quite often when I told men that I was a ladyboy seeking sex with them, they appeared not to be interested. But as soon as I lifted up my skirt and let them have a look at very cute little white-skinned cock...along with my very short, uncut penis of less than 2 inches...they almost...to a man...immediately got aroused, and some actually RAN after me as I was turning to leave. Before I went out as a girl, I poured plenty of icy cold water onto my cock to make both my balls and penis retract to the smallest possible size to make an open declaration to men that I was a submissive small-cock ladyboy who couldn't cause them embarrassment by getting hard. My small cock was a guarantee...a warranty...that I would not...was not able to... go on top of them, as was often feared by some men.
Most men did NOT stroke my penis while they were having me fucked, so I had to stroke my poor little pee pee myself to make it cum while I was being penetrated. Some strong men could shoot out their cum loads into the air -- and the cum loads sailed in mid-air for three or four feet before landing onto the ground. But I could just manage...after much stroking of my penis...leak out one or two droplets of cum...markedly very thin and noticeably watery...very much unlike the normally thick sticky cum men shot into my asshole and mouth...and I felt so inferior, and that made me become more and more determined to SOMEHOW have my useless, miserably small pee pee cut off so I could become a girl.
Third they liked my butt to be very round and bubble-like. Initially at 13 or 14 my butt was flat like any boy's but after intensive female hormone treatment with injections at both my arms and belly on a daily basis, my butt gradually acquired the feminine curves and undulating shapes men liked. They delighted at seeing my little cock with its soft small penis dangling and drooping in between my girly soft white thighs, and then their sense of of male superiority...the fact that their own penis was so big sitting in between their muscular hairy thighs...caused them to have a tremendous erection.
I usually took along a bed sheet when I went out and if I found a man who was interested in me, we went to a well-hidden spot behind some trees or a wall. Then the man would strip me down to bra and panties...usually having my bra pushed down to expose my big nipples...and having my panties pushed down to my knees to expose my small cock which I carefully held in one of my hands to prevent it from hardening...just in case...and then I INVITED them to take pictures of my body.
I liked pictures being taken of me while I was lying on a bed sheet in wooded and grassy surroundings, because that gave me a sense of liberation from the social restrictions I was in ...having my breasts wrapped up to pretend to be a boy...and as you can see from this picture, my face looked serene and contented, as I was preparing to be first spanked and then fucked by a nice boy I met long ago --one night at 3.30 am when I was aged 15.
Until I started having hormone injections on a daily basis in April 2013, my breasts were just these. I liked my breasts being in such condition, because I only needed to use a tight rope/bandage/wrapping to push up my breasts at their base so they would get the needed cleavage -- and become large and erect enough for a C Cup bra to be put on them. While I was crossdressing, the main attraction I had for men...quite apart from my small pee pee...was NOT my breasts, but the visibly soft and white skin at my chest and shoulders. That was clearly visible above the low cut of my dress, and stood out in the darkness of the night in all its feminine splendour, even under the dim street lights.
Because of the outdoor activities men usually get involved in either because of their work or because of their personal interests, they tend to have dark, coarse skin. So a crossdresser like me...with soft creamy skin...attracted men mainly by virtue of my white, smooth skin, at least that was what held men in suspense when they cast their first looks at me.
The door opening up to the rooftop of most residential buildings is usually left unlocked, and that was often where I sat late at night to wait for my game --- a lone man getting bored late at night and going up to the rooftop to breathe in some fresh night air to release himself from tension. A middle-aged man...preferably in his mid- or late 40.s...was my prime target for men in that age group tend to be more interested in ladyboys.
Usually if I stayed up at the rooftop for 2-3 hours between 12 midnight and 3.30 am, I could find a man walking up, often feeling very hot because of his needs in between his legs. Middle-aged men are (still are) very good at making a girl feel turned on by the way they stroke a girl's body, for they are invariably quite experienced in this sort of thing.
In particular, I liked being stroked and caressed at my breasts, nipples and cock, and I felt almost totally intoxicated as the strong arms of the man held me tight and close to his hard, male chest ---one hand of his was on my breasts...groping and clamping my nipples...white the other hand was digging deep beneath my panties to make me feel --- oh, sooooo good !!
The MUST thing that all men asked me to do on the street was to suck off their penis. From my standpoint as a crossdresser...and at that time a man...sucking off a guy's penis WASN'T so wonderful as some porn videos want to portray that to be. The penis, when fully blown up, tastes like rubber of the softest stuff, and for some men who have some kinky hangups, simply sucking their penis does NOT get them hard enough to get ready for having me penetrated.
Sometimes, I would prefer the man to suck MY small penis, so that I could feel what it was like to get hard inside a mouth. As for myself, I feel (still do) the fun part of giving a man's a blow job is to feel the soft penis get SUDDENLY harden inside my mouth, and it sort of blow up like a balloon.
And then I like the HUMILIATION of being on my knees to submissively serve a man, because it affirms my role as an obedient girl playing the stereotyped submissive female role. When the man cums in my mouth, he feels so proud...his manhood being affirmed and boosted...while I feel affirmed...and positively identified...as a girl, because only girls have to eat a man's cum, which is also sprayed onto my face to add to my most willing submission to men as a man in training to be a woman.
On the other hand, when a man, as this boy did to me in the picture, was willing to put aside his pride to bend down to have my miserably small pee pee sucked, I felt so grateful to what he was willing to sacrifice his male pride to do for me, and that gratitude made me become more obedient to him afterwards. When my penis was being sucked a man, it couldn't get hard the way men do, but there was this palpable feeling of hardening....those hardening sparks typical of manhood...going down at my penis. The men in my part of the world were seldom willing to suck my penis...just a few did...but those few who did it to me made me feel so glad...so grateful !!
The call of the wild...that flaming passion to cross dress to become a girl...usually woke me up at 3.30 am and unless I could get some release,...perhaps through watching a suitable porn video which could help me to imagine that I was the girl being fucked in the video...that burning passion...a irresistible drive that circulated like stormy sea in my blood and heart...MUST make me put on bra, panties and skirt to go out onto the street to at least walk around in girls clothes, and if possible to find a man, so his hands could touch my body -- all over, at spots that mattered most to me, which are (still are) my nipples.
As I was putting on makeup to make myself presentable as a girl, I was mesmerized by that sweet girl in the mirror...my female persona...and SHE must be allowed the freedom...coming out... which she wanted and so richly deserved, because she was so pretty. I normally chose NOT to dress like a slut... such as being in a low cut T-shirt and an upshirt...because an outfit like THAT would scare off men. Men do NOT like having sex with streetwalkers. They prefer having sex with a girl who looks like someone living his neighbourhood, or someone who looks like a schoolgirl or housewife.
That hot, raging passion might take quite some time to subside, and for as long as it lasted I HAD to keep loitering around on the street. I kept off the main roads to avoid possible police patrol cars...which were rare in my neighbourhood...and the public parks were my favourite destinations.
As day began to break, and the dark earth became awash with the faint morning light ... at about 5.00 a.m.... at least one or two men would appear at the public park for jogging or morning walk. I would sit butt bare on a bench near some big trees with my back against a wall...that skirt of mine you see in the picture was specially designed, so that when I was seated, my body was well covered from the front, with my breasts and thighs completely clothed -- but if one looked at my back, and then cast one's eyes downward, one can see my bare bottom.
( The ultimate aim of all my crossdressing activities was 1) to bring my nipples to THIS erect, firm condition which is (still is) essential for my orgasm and 2) to get any man/boy I met to have me penetrated in THIS doggy style, because it makes (still does) me feel all woman.)
In the semi-darkness of the early morning, I would wave my hand to the lone man jogging past by, saying, 'Hi, good morning....are you lonely ?' When I first crossdressed at age 13 and 14, I NEVER succeeded in attracting any man even if I was in this sexy outfit. I soon found that I got the wrong targets. At the beginning, because of my fear of physical attacks from men, I chose to play a safe game by approaching old or much older men in their 50's and 60's. I was usually IGNORED when I greeted them. I then found out from books that men in this age group might have andropause, a condition under which because of old age, they cannot or find it difficult to have an erection. Therefore I discovered that it was not that old men were generally 'decent', but that they just couldn't get hard. So I later switched to greeting middle-aged men, who responded well to my greetings.
Once a middle-aged man had been lured to sit beside me, he would see my bare butt, and my naked condition from behind. I chose to avoid teenage or young boys, because they might turn violent on me, and I had had experience of having been physically assaulted by young boys. Mature, middle-aged men are (always are !!) very good...and gentle... at stroking and caressing the female body...knowing where my most sensitive spots are...and like good teachers, they would teach me how to suck off their cock without using my teeth. My sweetest crossdressing experience consisted in moments when men succeeded in making my nipples turn ERECT and FIRM, because I need (still do) such condition to get orgasm, and that was particularly so in those days when I still had a penis, which found it so extremely difficult to get hard under any circumstances.
In my decade-long crossdressing loitering on the streets,.. at both day and night,.. I DELIGHTED in standing to pee in public. That could perhaps be a sort of perversity. Be that as it might, the feelings of standing butt bare or in mini-skirt...and yet not urinating like a girl squatting or sitting down...gave me a refreshingly good feeling of liberation and triumph.
At home while living with Papa , I was not allowed to stand to pee, and Papa made sure that I would need to sit down to pee even at school by having my cock tightly wrapped up, leaving just the tip of my penis out at an opening cut at the wrappings, so that if I did disobediently stand to pee at school, my urine would unavoidably dirtied my cloth cock wrappings -- and I would be whipped for that.
On the other hand, in the middle of the night, I often used squatting to pee as a technique to lure men to come near me. When I saw a man at some distance from me...such as a garbage collector or street sweeper...I purposely squatted at a spot within his sight, and sooner or later he would come forth to ask me what I was doing. If he was willing to come up to me, I was half way on the road to success, because that would give me the needed chance to reveal to him my ladyboy identity-- and my intention of having sex with him. By the way, NOT every garbage collector or street sweeper was interested in me, because, as they said, they were either afraid of contracting Aids or losing their job for having public sex. Even if I ASSURED them that I did not have Aids, that didn't work, so that quite often, I just loitered around the street...and having been unable to find a suitable target...just took a pee at a street corner...and went home, feeling released anyway for having urinated in public butt bare in girls clothes.
Closely linked to my obsession for crossdressing was my desire to be identified as female by members of that particular human specie --that is, women and girls.
You might have thought that when I crossdressed I ventured only to approach men for sex. In fact I wanted to get close and chat with a woman/girl just as much as I did in relation to men/boys. It was far more dangerous to approach a woman/girl, because women tend to be very sensitive to gender recognition, so that if I didn't make up myself very carefully to look my best as a girl, there was a good chance that the woman/girl I approached might just successfully READ me and then scream out for help, mistakenly treating me as a sex predator of some sort.
Women and girls are by nature more compassionate and helpful if they see somebody of their own sex in distress. I sometimes did approach women...mainly mature women for the sake of safety, for young girls got scared so easily...and I did so on the pretext that I had hurt some parts of my body, for example my legs and or chest.
Mature women would in most cases rushed all out to help me, giving me massage at those parts of my body which were supposed to have been hurt in an accident. I liked to feel the warmth and softness of their hands on my legs, hands, arms or chest because that gave me such comforting feelings of warmth, security and empathy, all of which were adorable feminine qualities I myself would have liked to embrace...I wanted in short to learn how to behave like a girl in real life.
The few women I approached in my decade-long crossdressing activities never found out that I was a man/boy, and all of them treated me with great kindness to see to it that my physical problems were solved. Indeed a few women praised me for having such white soft skin, because it was difficult for anyone to have such fair skin in a hot tropical region. They said, 'You must be a very obedient girl, always staying at home...otherwise your skin wouldn't be so white !!' Then I shared my feelings of frustration with them, which were that I felt so inferior and oppressed as a girl.
All the women comforted me by telling me they all had had such bitter experience of being harnessed/bullied by men, but they told me to be strong because as a girl, I must learn to somehow accept my fate as a human being a bit less equal to men/boys who society ENCOURAGED to have us women and girls bullied. I heartily enjoyed having such heart-warming girl/woman talk with people of MY gender.
At other times I showed some women the red lash marks made on my legs by Papa because I had been found to be not obedient and gentle enough, they all pitied me...as a weak girl being bullied by strong, macho men...and comforted me by telling me to be strong. All such words...coming from the mouths of people of the gender I wanted to acquire...warmed my heart in a way only crossdressers like me might understand.
Master's youngest sister... a girl in her mid-20's...was helping to adjust my new life to becoming a girl in the four months before my castration in December 2013. One day as she was opening the door of my bedroom room...which was locked from outside...to bring me my breakfast... she found that I was masturbating the MALE way, which was that I was looking at the pictures of some naked girls in a porn magazine while caressing and stroking my penis to work it up to that feverishly heated pitch that enabled me to cum.
She took away my porn magazine immediately and then she advised me to start masturbating the FEMALE way since in a few months' time I would need to have my balls cut off in Bangkok, Thailand. I sobbed and begged her to allow me to keep at least one porn magazine because I needed it to cum...I felt so bored and uptight if I couldn't get myself to leak out those few drops of cum that somehow got jammed in my penis, driving me to such infinite, non-stoppable restlessness that I couldn't sleep a bit at night.
Master's sister talked with Master about my problems, and they agreed that despite my crossdressing adventures, I was basically lacking in real-life experience as a girl, because I usually crossdressed for a few hours every day, but had never lived full time at day 24/7 as a GIRL. Master talked with his close friends about my problems, and they came to the conclusion that i must be made to become s STREETWALKER ...a girl loitering at night at remote country park lanes or urban back streets awaiting clients....so i could really learn what it was like to be a girl before i underwent that needed surgery to have my balls cut off.
Streetwalking is mostly done by low-class prostitutes with no homes of their own. When I was a teacher, I had always advised my students not to get close to such women, as they were in my view CHEAP. I therefore absolutely refused to become a street walker, even if I was only required to walk the streets for about two hours every night -- and if there was no client, I could go back to my little locked bedroom.
Master and his friends got very angry -- and for nearly one week, i was given suspension whipping two times a day...each session lasting for 15 minutes...very painful indeed, as some lashes were targeting my poor little penis. i could take the pain at my butt, but not at my poor little penis, so i knelt down and apologized to Master, saying,'Pleaseee don't punish me poor penis anymore...tooooo painful !...Pleaseee dress me as a girl and make me walk like a hooker on the streets !!' My face flushed red...almost crimson...when I said the word, 'hooker'. So starting in mid-October 2013, I began streetwalking...becoming a hooker instead of just being a crossdresser loitering around to get men hooked on a part-time basis.
That strange urge to put on girls clothes and start going out at night came all over me in the hours between 2.30 am and 4.30 am. However desperately I tried to keep on sleeping...to avoid the TROUBLE of crossdressing... I almost always wake up (still do)...with a start...during those hours, and just couldn't get back to sleep again.
Then the urge came...at first in bits...but gradually mounting to a crescendo which DROVE me... like the explosive force generated by the sparks of electricity... to get all naked -- and then, as if in sleep walking, I went in front of a standing mirror to look at my own image...yes, mirror , mirror on the wall, who is the most beautiful of them all ? Yes, the answer came...popped... into my mind - me- I had got to get that pretty girl out.
Whether I was indeed that pretty was not the issue, it was just that I simply must put on some makeup...in a rush...and put on my girls clothes...also in a great hurry...to go out onto the street to find men, not necessarily to have sex with them, though, but just to EXPOSE my body to the man so that his hands...yes his hard hands with coarse-skinned palms...men's hands are usually so stimulating...would touch my soft, lily white and smooth skin to EASE the pressure building up inside me.
Many of the clothes I put on were passed to me from my dead mother, and some others had been STOLEN from the backyards of some of my neighbours. Some women in my neighbourhood often forgot to collect back the bra and panties they put out at their backyards...on clotheslines... to dry, so that at night I sometimes sneaked out to steal their clothes, mainly lingerie and bras -- particularly bras which came in beautifully with different sizes, patterns, frills and colours, and I often stole the black, red and pink ones.
I never bought female clothing from any boutique, because I could not go though the embarrassment of being asked by the salesgirls there as to why I was buying those clothes. My dead mother had left behind a good stock of skincare products and makeup material --enough for my use for years --but I did buy some of those things at supermarkets though, since there I wouldn't be unnecessarily queried or secretly laughed at... behind my back...by the salesgirls.
After I had got dressed, I looked at myself in the mirror... at night, it was much easier to do crossdressing as the darkness would cover up even major shortcomings in my facial makeup. Thus mesmerized by my own image I would go out, leaving the door unlocked, closing just the gate so minimal sounds were made, and so neither Papa nor my neighbours would be disturbed or awaken by the squeaky sounds of opening and closing the door.
There in the darkness I loitered, walking through back streets and lanes -- waiting for the lone male passer-by, and there were usually a few. I had learned to avoid teenage boys who once attacked me, and I picked mostly middle-aged men. Old men seldom showed much interest, and at first I thought they were more 'decent' in that traditional moral sense, but later on I found that old men usually had an erectile dysfunction problem called andropause which prevents them from effectively having an erection.
Throughout my crossdressing years, I found that men were attracted to me by three things, namely, my white, smooth skin which tended to shine with brightness under the dim street lights, and then men liked to touch and squeeze my breasts...my nipples in particular... as one of the first things they did when they were prepared to let me serve them.
But my major selling point was not my skin or my breasts...which were small by female standards anyway...but my small, cute cock, particularly my penis which looked so submissively little, so attractively docile...miserably vulnerable... in its bald, clean-shaven state.
And then when the real thing came, I enjoyed being stroked at my nipples and butt cheeks...few men stroked my cock...I did that myself as I was being penetrated... and THAT titillating feeling of the hardness of the male body...so dark-skinned ... pressed against the softness of my breasts and butt...oh so very white... was a most addictive, unforgettable experience which kept driving me back to crossdressing in certain time periods of my life when I DID try hard to give up everything to live a NORMAL life like any boy.
The mirror is at the centre stage of my crossdressing experience. To arouse myself to an intoxicating, intense crescendo of sexual excitement...which was needed to give me the AUDACITY and RECKLESSNESS to go out onto the street dressed as a girl....I needed to look at my own image -- made up beautifully at my face and dressed up in pretty clothes on every every part of my body -- from the frilled hair band, pink ribbon and hair pins in different shapes on my hair to the flimsy stockings and 3-inch heels my creamy white legs and feet were in....
And then, in those magical, intimate moments of almost other worldly encounter between my physical shell...the real me standing in real on my feet at the bedroom...and the fascinatingly beautiful me, that mirrored fantasy persona in all the colourful splendour of female clothing .. which was that pretty girl, that female me in the mirror...I felt totally immersed, captive, and mesmerized.
That memorization soon accentuated to a climax as I was stroking my own body-- and as my eyes were kept glued onto the mirror, where that female me, the girl living inside my body, looked invitingly back at me -- telling me in cognition that she must be made to feel happy, contented -- and yes I heard her say, 'Let me be free.'
This meeting between my two different halves merged into one as that URGE once again came over me, and at my heart...as well as in the eyes of the quietly coy female image in the mirror, I heard the cry, 'Let's go out.'
And off WE went onto the street, braving the darkness...and the taboos of society...to seek that ultimate pleasure of self-realization fueled by an obsession that is called crossdressing.
The roots of crosssdressing are with...and in...the beautifully designed bras and panties of girls. It is rare indeed for anyone to grow up in a family without at least one person of the female gender, who should be the mother. In some cases, boys may grow up with as many as up to half a dozen girls, because he may have several elder or younger sisters.
And the bras and panties the girls/women put on are so very beautifully frilled, patterned -- and they feel, above all, so very soft when touched. But the clothes that boys are ever allowed to put on are so very dull looking with the colour range being narrowly limited to maybe just four colours -- white, black, grey or brown.
There was in my own experience a strong desire...almost determination...to break the almost dreary monotony of the male dress code and replace it with lively, attractive female clothing of any sort -- any female garment is in my view more attractive than the male one.
Before the death of my mother in a car accident when I was 11, she bought lots of very sexy, nice-looking and really pretty bras and panties. When she was not at home...out shopping or even simply busily occupied with housework somewhere at the other side of the house....I delighted in putting on her bra and panties, and then I so enjoyed looking at my own fresh, girly image in the mirror -- with my small, white and neat body being so beautifully presented...and enhanced...in Mama's pretty pink, red or black bra and panties.
I kept my bedroom door carefully locked while looking at myself in the standing mirror -- oh such a beautiful me. Afterwards I carefully folded Mama's bra and panties and put them back in place into the drawers where they belonged.
I wished I could have breasts so I could put on those, oh, so femininely attractive bras, and I hated seeing that little ugly bulge beneath the panties. I would have preferred the V-spot between my legs to be flat and neat, like Mama's.
In my view, if you have a boy...or boys... at your home and you won't want him/them to run the unnecessary risks of becoming, like me, a crossdresser... eventually ending up in MtF transition... you should make sure that ALL the bras and panties of the women and girls in the family are kept put of reach of the boy/s...preferably to be secured under lock and key...so your boy/s won't ever be able to use them for such GREAT FUN when you are not around.
Once a boy has put on bra and panties...especially the BRA...he may --'will' is more appropriate in this context --easily get obsessed with that nice image of his with a pretty bra on -- and the road to crossdressing is, perhaps unfortunately, about to begin for him.
In my view, a place with four seasons, with a winter, is most ideal for crossdressing. In the tropics...where I am...I was often in shorts and mini skirts... I must have some clothes on...while walking around the streets in search of the right men/boys. But in a place with wintertime, I could just put on a big, warming overcoat...having it fully buttoned up from top to bottom...and there was therefore absolutely no need to put on anything beneath that overcoat.
As I was teaching during my university years, I had money to travel abroad. For several times I was in Hong Kong.
Hong Kong people are very busy and won't care to look at anybody or anything while walking on the street, and in wintertime, people get themselves wrapped up in thick winter clothing as soon as it is 15 degrees C or below. So there was absolutely no chance for me to do any crossdressing at day because of the very look of the overcoat, which prevented the curves of my body from being SEEN from any angle.
But in the small hours of the morning, from midnight on, things turned favourable for me, so I put on a big overcoat with nothing beneath it ...I left the hotel and began loitering about.
During the three trips I look to Hong Kong, on Hong Kong Island city and a peninsular city called Kowloon...in three different districts respecively called Wan Chai, Shamshuipo and Western District...I met up with quite a few men on the street, and there were quite a lot of them in a big city like Hong Kong.
I let them as usual know what I was, and if they were not frightened off by what I was, I unbuttoned the lowermost buttons of my big overcoat, and let them have a look at my cute little clean-shaven cock. If they care to stay put until that moment, the sight of my cute little cock...with its lovely- looking soft small penis lying docilely on small pillows that were my balls...was SURE to be able to lure them into my 'trap'.
All the men I met up with were Chinese, but since I am also an ethnic Chinese, I had no problem in communicating them. We usually had sex in the men's toilet. It was very easy for us to have sex as I would just need to unbutton my big overcoat, and then I could be fucked butt bare and when sometimes there were two men with me, one would have me fucked in my face, while the other would penetrate me in my asshole.
There was absolutely NO danger of being caught by the police as if anybody else was entering the toilet at any moment, I could fold up my big overcoat in seconds. The men were basically never in danger as they were fully clothed, leaving their fly open, which was what men were supposed to do anyway at a toilet.
Some men thought that I was doing that for money, and gave me a bit of money after having me fucked. I accepted the money to set their hearts at ease, as most men outside the corssdressing community wouldn't understand why a boy ...such as me...however feminine-looking...should dress in girls clothes wandering around the streets in the middle of the night.
This was me, at the age of 15. The picture was taken by one of my schoolmates just before I had sex with him.
Ever since three of my schoolmates had discovered that I was being trained to be a ladyboy at home, Papa had asked me to have sex with all three of them so that they wouldn't tell the school principal about my secret - the school would kick me out if they ever found out that I was a ladyboy. Boys crossdressing to be girls at day or at night is deemed to be a very serious moral offence and would definitely lead to my immediate expulsion from school or even a jail sentence if for example, I was found to be having sex with a man in public places -- such as at a toilet or a street corner.
In those early days, I was just taking contraceptive pills...at three pills a day... and I was unable to grow large breasts which remained rather small -- indeed they were hardly noticeable if I straightened up my body.
But my skin did look very feminine --soft, white and smooth, and I was learning to obediently kneel down...like any girl... to suck off the boys and then get down on my hands and knees to be penetrated by them. However you may look at it, this kneeling down thing is very humiliating. But somehow, once I got used to it...being down on my knees at a man's feet...I seemed to have got OBSESSED with it...and, then as now, I LIKE it this way, which is to get down on my knees to be be fucked by men.
This was the way I pressed down my breasts to simulate the flat male chest. My cock was turned inward to be tightly sandwiched in the V-cavity of my thighs to simulate the flat female pussy. As my breasts were growing ever larger because of heavy female hormone intake...reaching nearly 33 inches when I was 18...I needed to have them pressed tight and have them FLATTENED to avoid suspicious-looking eyes from casting on my chest when I was attending university lectures -- and while I was teaching part time as a male teacher at a boys' secondary school.
But Papa insisted that my cock...especially my penis...must be kept small, so my cock had to be bound tight and curled inwards at my butt cleavage. While I was walking around with my cock bound, I really felt like having nothing but a flat ...and fat...pussy in between my legs---and it was in that condition...having my cock bound in this way...that I started getting used to sitting down to pee.
While studying at the university for my honours degree in English Literature and History, I felt the female hormones I had been taking since the the age of 13 began to have major impact on my emotions, feelings and sentiments.
I felt increasingly interested in BOYS, which I didn't want to ...how could I, being a boy myself, fall in love with boys in general, or might be one boy in particular ?...and I believed that it was just an undesirable side effect of my crossdressing sex adventures at night.
Most of the students in my major subjects, literature and history, were girls, Girls are generally better than boys in such subjects, but in my class, I was an exception in that my grades were consistently better than those of my girl classmates, and I soon became a pet of my lecturers. I knew the girls were envious of my academic success.
And behind my back, I often heard the girls gossip about me, saying that I was sissy, and when each Department was asked to send out a representative to participate in the Inter-faculties Third-year-students football tournament, the girls. probably to punish me for being too good at English, wanted to choose me...the only boy in the third-year literature class...to represent the English Department to join in the Arts Football Team which would go against the boys in the Civil Engineering Department.
Football was much too rough a game for me, and it wasn't possible for me to change into sports wears in the men's changing room -- because I had breasts hidden beneath my shirt. When the Civil Engineering Department representative, a very handsome boy, came to our Literature Department meeting to oversee the so-called election of a representative from my Department, he found to his surprise that there was no room for a choice, because I was the only boy student there was in all Year-three core modules of the English Literature Department.
The girls insisted nevertheless that I must represent my Department, but I absolutely refused to do so, and then that boy said he would see me in my hostel room to discuss with me about the matter. When he was in my room, I explained to him that all my life I had never played football, and I had spent most of my time on doing household chores like a girl, so the game was too rough and tough for me.
I put on short pants to let him see my slender, softly white legs without hairs, and insisted that I wasn't suitable for playing football with such legs. And then I broke down in tears, because I was so afraid of somehow letting everybody know ...right there in front of thousands of eyes...that I had breasts and was a ladyboy.
The boy said that rules could not be changed and as Chairman of the Selection Committee, he must choose me to represent my department. In desperation, I got down on my knees and told him my secret, which was that I was a ladyboy, and if the university found that I was a ladyboy, they would kick me out for having breached basic moral codes.
The boy caressed my hands, saying, 'Very small and white.' And then he stripped me naked, and while patting me on my breasts, he said, 'Don't cry...I will do something to help.' He kissed me on my lips...and cock...making licking rounds at the tip of my penis with his tongue.
I felt so very weak...and drained... and then we had sex. While he was penetrating me, I felt my penis began to harden...I asked him for permission to get hard... and then I handed him a table tennis bat telling him that he could spank me on my butt if he was offended by my getting hard without his permission. But he was so very kind, saying, 'Sure...get as hard as you can...your butt is round and cute...I will never spank it, dearest.' Oh he was so kind to me, and my heart was touched, and then I sobbed in his arms because I was so grateful to him for his kindness, understanding and concern.
At the next Faculty Football Tournament Meeting, the boy, as Chairman, announced that the English Department would be exempted from the football contest because of a technical inconsistency with the rules : Since there was just one boy...me...in the Third Year of that Department, there could be no 'selection' in its strictly legal sense, and as the normal selection procedures could not be legally carried out in my Department, the whole Department would accordingly be exempted from sending a representative to the football contest.
I was so grateful to the boy, and one night I met up with him at a seaside somewhere in the outskirts of the town...and under protection of the darkness around us, we had sex under the witness of the twinkling stars...and as he was caressively touching my breasts and butt, and ramming his very big, 7-inch penis into my asshole, I felt fulfilled and so very happy-- in a way I never did.
In the days following that...over a period of nearly six months... we met two or three times a week, and I dressed and made up beautifully for him. To avoid being seen in girls clothes, I went out with him at 11 pm and went back to the hostel at half past one in the morning.
We walked together in the darkness, hand in hand, at the deserted streets...at times stopping at dimly lighted street corners for a face-sweetening kiss or a heart-warming embrace -- and then we hugged each other at the public parks...having sex there...with my boobs fully exposed -- my nipples standing firm and erect when gently glided over by the evening breezes.
He said that I liked my cock to be small and cute, and so I carefully had my penis bound tight...as tightly as possible...to make it retract to form a small lump. Before having sex with me, he unwrapped the bandages on my penis, and if he was satisfied that my penis was soft and small enough...that was, I could definitely not get hard enough to be ever on top of him...I would be graced with being fucked butt bare. He often asked me, 'You like being fucked like a girl ?' I assured him that I liked to play the female role -- and that set his heart at ease.
Then I told him my dark little secret which was that I could get hard if I was whipped on my butt...I needed to get at least a bit hard to be able to cum...and I begged him to have me whipped because I liked the liberating feelings of leaking out my cum loads.
He took off his waist belt and had me whipped on my butt, and as the 'bak'...'bak' sounds of the belt impacting on my butt kept reverberating at the park, my soft penis got hard, and then I had orgasm and could at last cum to get that much needed relief from the hugely big tension building up inside me.
But that happiness of mine was not to last long...the boy soon graduated, and then he went to Canada for his advanced Master's degree almost immediately after his graduation. I sent in emails to him. At first he gave me long replies...then the messages got ever shorter...and soon I noticed that he always intentionally kept a distance from me in the way he wrote. Then one day he sent me this email, '...I would have loved you for all eternity but for the fact that you are a boy. I can't spend the rest of my life being married to a girl with a cock.'
After that I heard no more from him. I looked at the pictures I took with him : He was holding my hand tight, and I was smiling beautifully, having had myself carefully dressed and made up to create the prettiest girl image I could think of to help him keep me, hopefully for ever, in memory.
I looked at the picture, and then, almost desperately, I looked at my small cock. Oh, why was God so cruel to me by forcing me to hang this extra something in between my legs ?
(Me - Having sex with my lover at the university, and he had such big, masculine hands !!)
When Papa didn't return to his rented flat there in Singapore, I sneaked out at night to that sitting-out place after 12 o'clock midnight. Once, I met up with an Indian Tamil man. He approached me with his shirt wide open, showing his very hairy chest, like a gorilla's, and I liked that.
I asked him whether he would like to have some fun with me, and he nodded his head...held me by my hand, which his big, hairy hand caressively touched...and then he took me me into an HDB flat lift. He pushed the button for the top floor, to which the lift ascended, and then he stopped the lift there. He touched me on the V-spot between my legs, just beneath my skirt and he asked, 'Are you a boy ?' I said, 'Yes'. He said, 'Good...nice skin...pretty boy.'
There in the stuck lift, he stripped himself....and me...all naked. Oh, his penis was so very hard and huge....almost nine inches...and then he caressed my body...and kept my small penis swinging left and right...for ten minutes. Then he said, 'I have made you happy...now you make me happy...suck.' I got down on my knees to suck him, and his cock was so huge, penetrating my mouth with such ferocity that I coughed. He then tried to penetrate me in my asshole...I felt the tip of his penis pounding in...it pushed in just a little, and when it attempted to go in deeper, it sort of got jammed. Afterwards, he said, 'Your asshole is too small. Maybe next time.' He gave me his phone number, but I never contacted him because a penis like that was just much too big for me.
In the months before my castration in December 2013, Master invited dozens of His friends to have sex with me so i could get used to my future life as a shemale escort. That period of training, from March through December 2013, was meant to make me accept the reality that my cock as a whole must be made soft and dysfunctional.
It was there merely to amuse and arouse men/boys, but i would never ever be allowed to use it for penetrating anybody, especially girls because i must remember that i myself was...am... and always will be a girl, and having my cock turned hard was punishable by (harsh) whipping.
So when Master and/or His friends had me fucked during that period, i always remembered to hold DOWN my penis, and forcibly twisted it backwards if and when I felt that it was hardening at any time.
In the period between March 2013 and December 2013, I was practising for my future job as a shemale escort by streetwalking at night, looking for men/boys to have sex with at just USD 10 for half an hour, and sometimes the price I asked for was just USD 5, since I knew that I would get whipped or spanked if I returned home empty-handed with no money having been earned.
I didn't dare to walk out in the open where there were crowds outside bars and restaurants, because I was so afraid of being read as what I really was, and I might get beaten up for that. So I loitered at dark street corners, with understandably not many people walking by, but there were still a few.
I would ask to be taken either to a hidden back-lane staircase corner, or I might take the man up to an unlocked rooftop of a flat nearby. An unguarded rooftop was in fact much safer than a street corner, as there would be no police patrol there. As I said, I wasn't taking female hormones regularly in those days, so I didn't look too pretty, so in fact on most occasions I just let the man pay any amount he felt like it, and I didn't ask for any fixed fee.
So most men paid me just USD 5, usually for the blow job I gave them, and some paid me USD 10 for playing with my small penis...turning, twisting, pressing and pulling it...but just one or two men even asked to penetrate me in my asshole in any one month, most men citing their fear of my being an STD (sexually transmissible disease) -carrier as the primary reason for not having anal sex with me.
Picture Below : As a crossdresser, I LIKED stealing women's lingerie from from among the clothes taken out for drying on clothes lines by my neighbours. Actually I felt it very embarrassing to buy bras and panties from department stores, because the salesgirls often sort of gazed at me, in wonder, as to who I was buying those bras and panties for.
The easiest way to replenish my stocks of bras and panties was to steal some from my neighbours. Many different kinds of bras and panties...many of which had beautiful designs, frills and patterns...were taken out for drying in the afternoon at the backyards of the terrace houses in my neighbourhood. The house occupants were usually at work/school somewhere during the afternoon hours in between 2.oo pm and 4.30 pm. So when I felt THAT need to put on something different, something really attractive or sexy, I would just steal one or two bras or panties from different neighbours. It took less than two minutes to snatch a bra or panties off a clothes line and I was never caught.
Because the number of clothes items they lost...stolen by me...was so very small...just might be on average 2 bras and/or 3 panties per year/per household...hardly any woman/girl noticed that they had been stolen by somebody.
Just one teenage girl suspected that I might be involved in the loss of her cute underwear, and one afternoon, as I was walking by one of the terrace houses...intending to steal something...she rushed out from her house and asked me whether I had seen her cute Hello Kitty bra. I DID steal her bra, but I shouted at her, asking her what she was asking me about her bra for, because I was a boy, and I never even looked at bras being hanged out on clothes lines in my neighbourhood.
Then I told her to hang her 'smalls'...her bras and panties...behind other clothes, so they wouldn't be easily seen and therefore cause embarrassment to me or other passers-by. The girl's face flushed red, and she immediately apologized to me for her rudeness, and never asked me about her lost lost bras again.
I had over the years (from junior secondary school to university) stolen a total of 16 bras from that girl, by the way, because her bras were so very cute, always having Snoopy, Hello Kitty. Teddy Bear, Angry Birds and other cute cartoon characters sewn onto the bra cups.
One of greatest fantasies I had was to be CAUGHT by someone...preferably a mature man...for urinating or defecating on the street. To realize that fantasy, I often chose to purposely squat at a street corner....I lifted up my skirt, way high...and then I started urinating right there at a street corner under cover of darkness, but with my big, round, lily white butt fully exposed to view under the glow of the street lights dashed onto it. I did that many times over a period of nearly 10 years, but succeeded only once.
That single memorable moment was when I squatted to pee behind the walls of an electricity generation outlet. A Malay street sweeper approached me...he was dark and bearded, just the sort of mature man I liked...and he ordered me to get off immediately as he was sweeping the locality. When I was standing up...with my panties down...skirt lifted up...he saw my small, neat-looking cock, and then he said, 'Wait...are you a ladyboy ?' I said 'Yes', and then without asking for my permission he pressed me down on my knees...he unzipped his fly...and , oh dear, his penis was like an elephant's, dark, hairy and nearly 8 inches hard.
He said, 'You need to be punished for dirtying the streets with your urine.' Hue then used his big hands...with worn-out, rather dirty-looking finger nails.... to pull up my T-shirt, and then he said, 'Nice...very white skin...big nipples.' Without further delay, he pushed his big rock-hard penis into my mouth, and penetrated it with such force and ferocity that I coughed uncontrollably when the tip of his huge penis touched the top of my throat. I pushed him off, because he was getting too rough. I said, 'Enough !' but his replay was 'Not enough', and then he ordered me to get down on my hands and knees...made me butt bare...and attempted to penetrated my small asshole.
He tried to enter me, but it seemed that my asshole was not his size, so that he pushed his penis back into my mouth again, and then he started cumming, and his cum...lots of it... spilled all over my face. Then he said,'Get dressed. Next time don't urinate on the street or I won't spare your little asshole next time !' Then he went back to his work of sweeping the street and I quickly walked away, feeling SATISFIED because my fantasy had been realized.
(Even NOW, having become a girl, I still like urinating and/or defecating at street corners, staircases and public parks, because urinating in public and if possible being caught by a man in the act is such fun !)
Whereas I enjoyed sucking off a guy and if circumstances allowed, had anal sex with him, I did NOT like being kissed by men, because most men/boys didn't shave their beard properly, and the beard/mustache stubs left on their jaws, chins or upper lips were quite sharp and sort of prick my soft facial skin, causing my jaw and chins quite a bit of pain upon rubbing with theirs.
Nevertheless, that was seldom a problem since most men were in such a hurry to finish having me fucked at a convenient, outdoor spot somewhere that only one out of every ten men I picked up on the street ever had me kissed.
But then those who cared to take me to a hotel room did kiss me repeatedly...not just at my face, but my whole body, especially my breasts... and I normally needed to close my eyes to control my own face from sort of withdrawing from such encounter of the most unpleasant kind.
The male toilet is the most ideal place for having sex with men. As a crossdresser, I spent much of my time loitering in the early morning at urban locations where there was a public toilet.
At night, the toilet is usually visited by men of different sorts...old men who because of health problems need to urinate at frequent intervals...factory workers returning home from night shifts...and some drug addicts.
When I found a suitable target.. usually a line passer-by without any companion...I would walk up to him and tell him WHAT I was by lifting up my skirt to let him see my cock. This trick ALWAYS worked, even if at first the man would out of suspicion or fear refuse to even get near me.
That was because my cock was really very small and neat after it had been shaved clean, and I made sure that, after having been dipped in icy cold water for 15 minutes, my penis retracted to its smallest, most lovable length...about two inches...when I crossdressed as girl at night.
So even if at first the man would say, 'Go home...go away' when I first approached him, he would come after me after I had shown him my little lovely cock, because it indeed looked so very cute, so very docile, looking male yes -- but my little cock was decidedly submissively feminine in overall looks because of oolour contrast effects of the clear, white skin of my legs.
After the man had seen how small my cock was...how short of penis was, like a little peanut...he would become confident that I would be UNABLE to get on top of him.
So then the two of us would go inside the toilet to do what I wanted, that was to have the man's hard penis inside my mouth...oh to piss right into it or to shoot his cum into it...and then if he liked, he could penetrate my asshole.
Having sex at a public toilet is 100 percent safe, since it is done behind close door, and we could therefore have plenty of time to readjust our clothes if intruded upon by a patrolling police officer. The man would just need to zip up his fly, while I just needed to put down my skirt. It is perfectly legal for a crossdresser to use a male toilet. Indeed people will be surprised if I used a female toilet, since I had a cock with a full set of testicles and penis.
Hi Jeniffer,
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How Can I contact you ?
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