I love mature men

Although I grew up in a very small family with just my stepfather, Papa, my extended family on my mother's side is very large, with large numbers of uncles and cousins. My uncles all know about my upbringing as a girl, and occasionally (just two or three times every year) when they visited Papa and I they noticed that at home I was in girls clothes. 

They asked Papa why. Of course Papa wouldn't tell them he was having sex with me, and he gave them the simple answer that since my cock was so very small, and I was so soft and timid, it would be in my interest to train me to be  a girl, and amid their laughter, they chatted about how I could ever get hard with a penis no longer than 2 inches - and  as they were chatting, they often asked me to pull off my skirt to let them see my small cock....and my very white butt and thighs...and I noticed that my uncles all got very hard when Papa asked me to get down on my knees to serve them tea butt bare. 

I did hear that some of my uncles asked Papa for permission to have sex with me, but that was always turned down since Papa said that I was after all a boy and getting down on my hands and knees to be fucked was just for real girls. Papa sounded so morally decent that my uncles never ever dared to ask to have sex with me again. 

Now that I am working as escort, my uncles are among my most supportive patrons. They like having sex with me  -- with me being  dressed like the way I used to ...in male sweater...and they insist that I must at all times spread out my legs wide for them to see how FLAT I was down there, with my cock having already been cut off. 

THEY TELL ME THAT PAPA HIMSELF WOULD LIKE TO HAVE ME BOOKED, BUT JUST DIDN'T HAVE THE COURAGE TO FACE THE SITUATION BECAUSE PAPA BLAMED HIMSELF FOR HAVING MADE ME BECOME WHAT I AM NOW, AN ESCORT WHO EVERYBODY LOOKS DOWN UPON. 

One day, while having me penetrated in my asshole, one of my uncles...a fat, bald middle-aged man with just primary school education....asked me to allow him to take a picture of me, with my legs widespread to show that my cock had been cut off...so he could show the picture to Papa, because Papa would very much LIKE to see my bottom, he not having seen or touched it for so long since I left home after university. 

Then several weeks afterwards, my uncle returned, passing me a handwritten note by Papa, which read  : 'Thank you Jennifer...would it be all right for me to have you booked and then have you fucked ?'

 I passed the note to Master but Master said no, because He didn't like Papa for not having me castrated much earlier, leaving the 'MESS' for Him to clear. When I told my uncle that Papa was not allowed to have me booked, my uncle felt so disappointed, because he said that if I had agreed, Papa would have given him USD 300 as reward for getting me back.

As I was growing up as a boy, one thing I missed out most was the chance to grow body hairs, all over, if possible on my chest and all over my legs. Papa would have me whipped if I did not carefully shave  off all my body hairs, including my pubic hair, so that my body was not just smooth and white, but  always kept soft and hairless like a little girl's. 

Although I was exempted from physical education lessons on (falsified) medical grounds, I still had to put on shorts in physical education lessons to do some easy gymnastics, alongside the girls to get my basic physical education grades for admission to university. 

I felt so very shy about my slender, white arms and legs...totally without hairs...exactly like a girl's and the boys called me 'Sissy'...'Cecilia', that was another nickname for me...right in my face. Then after castration, Master put me through a 6-month-long electrolysis session for permanently removing my body hairs, including pubic hair. 

So I often feel so inferior, so inadequate, since I have never had body hairs of any sort, not even armpit hairs. 

And those of my clients who have lots of body hairs are usually in their 40's, and I so looooove to press my body and face against their body hairs, which cause friction on contact with my soft, white and smooth skin....and THAT friction, that titillating feeling of being brushed over by thousands of small brooms, makes me feel so very high, so very turned on, that at times I can't control saliva from flowing out from my mouth -- and I often have to squirt down there at my pussy once a man's hairy body is upon any part of my body, particularly my breasts and butt cheeks.

My former teachers and teaching colleagues are among my most supportive clients. 

Unlike my students...who come book me just to punish and humiliate me...these teachers, most of whom are middle-aged, sympathize with my situation. Although when I was a boy I was admittedly sometimes too proud, the new me...with my eye brows having been shaved off...my ear lobes pierced with twin/triple ear rings...my neck collared...my hands and feet chained...my whole body lily white smooth, soft all over without muscles...and my penis 98 per cent cut off...is VERY attractive to them. 

They say that I am humble, obedient and dependent now, and am no longer the haughty, aggressive and boy teacher I once was. They know that the club managers will have me whipped if I do not speak 'correct' broken, ungrammatical  English like primary school students, so they bring along some English compositions written by their students for me to read. 

The compositions are full of grammatical errors but clearly show the 'standardized grammatical structures' used by most of my clients, especially my own students who still form over 60 percent of my clientèle.

The trouble with me is that my English is too good, so to twist it back to the shape it once was when I was at primary school takes much patient teaching. 

I am a slow learner, and so my teachers and teaching colleagues do not hesitate to order me to get down on my hands and knees to be spanked, but only gently with their bare hands, and never with the small rod given to them by the night club in case I am found to be disobedient. 

So if I say 'I will make my skin whiter and softer' instead of the  colloquial bazaar English 'Me makes skin more white and mighty soft', they will just finger fuck me...very gently, at the perimeter of my pussy and asshole only...never too deep down and in...so I won't get hurt. When I finally manage to say the correct version of any sentence, remembering to add -s to 'make' after 'I' and 'We'...the way my students do ...they praise me, saying 'Good girl, Jennifer, very clever'. 

And I feel so pleased, because they will also send in straight-As feedback reports to the club managers, who will then report back to Master, who will then love me, cherish me and hug me ever more !!

In recent months, a middle-aged man who was Papa's close friend is coming to book me at increasing frequency.  When Papa started training me to be a girl at the age of  13, he used to come to my home to observe how I was being feminised  by being made to kneel down to serve him tea, and he was often invited to have me spanked butt bare if and when Papa found that I was not soft, gentle and obedient enough.

One day while he was observing how Papa stripped me naked to be whipped butt bare for not having skin that was white, soft and smooth enough, he suggested that since my looks were so pretty for a boy, and my school grades were so good, he was thinking to make use of my sperms to make his wife pregnant, and he said that it would be wonderful to have a boy or girl who looked like me, and with my soft, white skin and submissive character. Papa said that it was okay and in the following day I was taken to a clinic where the doctor used a forced orgasm machine on my asshole so I got so turned on that I shot out a good load of cum, which the doctor as far as a I knew had then inseminated that man's wife with.

Now nearly 13 years afterwards, this same man is coming to have me booked at least twice a week. He does not fuck me, but asks his son, a primary school pupil aged about 11 + to first have me spanked and then have me fucked in my pussy and asshole.

The boy looks  remarkably like me, with soft white skin and a small penis, but unlike me he is very aggressive and dominant. He often have me collared and then have me crawled and barked like a dog before having me fucked in my face, pussy and asshole, with the sort of ferocity and strength I couldn't possibly imagine that his small penis could sustain, for I myself...having a very small penis before my castration...wouldn't have imagined that a small penis like this little boy's could be THAT strong.


My neighbor....that middle-aged man...insists that I MUST moan and beg for mercy from the boy as I am being spanked and fucked by the boy, so that, as he says, his son will grow up to be more 'man' and will know how to control and discipline his wife after marriage.

The boy keeps asking me all sorts of questions while having my breasts squeezed and fondled, and the most frequently asked question is how come my English is so poor and yet I could find a job as a teacher before my castration. I answer him by saying that I am now a girl, and I need to train to be stupid, ignorant and humble so that I can become more obedient, inferior and then can be  more well liked by men and boys. The boys laugh, saying that he has never heard such stupid talk before, and have me spanked butt bare for my stupidity.


I don't mind being spanked by young boys...they have been doing this to me for several years, but this boy, looking so very much like me when I was at his age, has me feel worried. Might he be, in a twisted sort of way, my own son ?

Since Day 1 of my MtF transition, Master decided to train me to be a timid, dependent child. i was told to forget my past as an independent, educated adult. The most embarrassing thing about learning to be a small child is NOT speaking poor broken English...that can easily by managed by memorizing some basic pidgin English rules normally used by street hawkers, maidservants and waiters...the most difficult thing IS ...yes still is...ask men/boys to help me with excretion and urination, and to help me to take a bath. When i was in training at Master's residence, the sons of Master's friends...aged between 12 and 19...all had taken their turns to help me with using the toilet and having my daily bath/baths.  

Now my condition is better, I am asking the much more gentle, mature clients to help me with such matters. Instead of using the bath as an occasion to squeeze, twist and even pinch me all over, mature men bathe me gently, first having my breasts cleansed and dried, and that is followed by plugging woolen balls into both my pussy and asshole to give me the inner of comfort of deep cleaning and cleansing. For mature men, a bath is a bath is a bath...yes they do touch and caress me here and there...but for the boys having me bathed is having me tortured and humiliated, which is an entirely different...almost repulsive....experience.

The fact that I am now so very free going online writing about my MtF transition and escort experience is due in large measure to the help given to me by several mature men at the initial stages of training to be a submissive slave girl. 

When Master discovered that  i...as His administrative assistant.... had embezzled money from company investment funds for my own private use in buying clothes, makeup kits and hormone pills, He was determined to send me to jail. But three of Master's closest friends helped to persuade Master to give me a chance. Yes i was bad, having stolen money, but then... they all said...  i appeared to be soft, feminine and obedient and, Master's three friends said, i would be very good material for shemale escort work.

So Master gave me a chance on condition that i agreed to under feminization ...which i myself liked anyway...to train to be an escort, with castration to be carried out on me if i was found to be too disobedient and too boy after six months of training.

Despite long years of crossdressing and making myself up to be a girl at night, my shape wasn't good...for a girl...at all. My advantages in training to be a girl were just that i had a small girlie frame, small hands and feet, and that my penis was very small and soft, largely dysfunctional because of long years of having taken contraceptive pills. Having said that, my skin colour tone was uneven with those parts of my body exposed outside my shirt....arms and neck...notably dark, almost tanned at my upper arms. And then my breasts were so just small , with just my big nipples being in female erect shape, but still big enough. 

All those defects did NOT stop Master's three friends....all in their late 40's and early 50's...from patiently having me caressed all over, and then had me fucked most gently and slowly in my asshole --- to  kind-heartedly cause me minimum pain. Without the patience of understanding of Master's mature friends, i couldn't have possibly got used to my new life as a girl so successfully during the initial stages of my training. 

These kind men didn't mind the fact that i still had mannish muscles on my arms and legs...especially my legs, because i needed to stand to teach as a teacher...and they comforted me by telling me that having hard muscles was all right....i was born a boy anyway...and those muscles would definitely all disappear to become fats as soon as i underwent castration to have my testicles...my balls...cut off. To these three mature men I am eternally grateful for the success i have had in my MtF transition.

My mature clients consist mainly of my teachers, visitors from abroad (mainly British and American) -- and the fathers of my boy students who I got to know on occasions of   school-organized interaction meetings with parents and/or annual home visits which teachers must made to parents of students with poor academic results.

As most of my students had poor school grades,  over a period of four years' of teaching as a male teacher, I got to know quite a lot of men. The fathers of my students knew me as a soft-spoken, gentle teacher with unusually white and smooth skin for a  person of the male gender.

When some men complained to me that I was a bad teacher, so that their sons had such poor results, I couldn't help controlling my tears...I said sorry...and  a few men demanded an apology from me, I actually got so ashamed of my performance that I got down on my knees to say sorry. 

Now that I am a shemale escort...and am having sex with their sons on a regular basis,,,these men, as fathers who I knew, also have me booked. They say that they got a great interest in me as soon as I saw them for the first time, my skin being so white....my hands and feet being so small...and my voice so soft in a sissy sort of way.

They like to have me fucked doggy style, and often enter me most gently, and when my asshole is being penetrated, they never  do it in a rush, but always make sure that I am being drilled  gradually, sort of inching in, and if I moan in pain, they will withdraw and allow me time to lubricate my asshole again for furthermore penetration. 

They like to have me fucked with my glasses on, the way I used to look as a teacher. They show great sympathy for me for being required by the night club administration to speak broken,  very poor English but comfort me by telling me that it is all right, because men like girls   the way I am, being stupid, ignorant and uneducated, so that I am  most attractive because of my poor English and total submission to men.

They say that my character is suitable for my work, as I am by nature soft and submissive, and if I had continued being a male teacher, my pretty skin and looks...along with my bedroom skills...would have been wasted. All that makes me feel good, and I am so glad they keep coming back to have me booked.

Mature men in the 45-to-65 age group like having me dressed and made up as a little child. They help me to take a bath first....carefully have my hair bound  and combed into double ponies....and some even FEED me with a mild bottle.

 And then they tell me stories from Andersen's Fairy Tales -- while my nipples and pussy are being caressed by their hands. I LIKE being made up and dressed to look like a child, and after all the love and care these men give me, they will ask me if I have been a naughty girl at any time during  my life. 

I tell them the naughtiest thing I did was to teach part time as a male secondary school teacher while at university. THIS  mischief always gets me spanked butt bare while being placed on the knees of these mature men.  Being spanked by mature men always gets me wet at my pussy, and the pain mixed with pleasure cause tears to swell up into my eyes.

 Then they say, 'Don't cry, Sweetie' -- and then they pat me on my double ponies, my cheeks and that little penis clitoris I get in between my pussy lips. Oh I feel so relieved as the mental pressure building up inside me is being drained by their kindness, understanding and compassion. They KNOW that it is hard for me to train to be a child, but they say I am doing the right thing, since my body is so small and my face has the typically  innocent looks of a little girl.

 If  I keep moaning in pain and persist in begging for mercy, they will let me off their knees, and then I will be fucked hard, brutally hard, till the last fibres of my being seem to be breaking apart by the sheer force, velocity and determination with which these men have me fucked, usually in my pussy....which is what I like...instead of in my asshole, which could cause me unnecessary pain. I like mature men because only they are willing to treat me, bathe me, discipline me and have me fucked like the little girl I so very much want to be.

ture men are very good with their massage skills. They seldom have me fucked straight away, as do most boys, and they choose to used their fingers/the vibrator  to gently caress my pussy and asshole before having me penetrated.   

While my pussy/asshole is being gently vibrated/massaged/caressed/touched, they keep on praising me for having a pretty, neat pussy, and they use their hands to purse my pussy lips, so that the clear outlines of my pussy stand out clearly even if I am in panties or trousers, as the case may be.  That turns me on, because I do like to have a pretty-looking pussy, and I want to see it being pursed up like sandwiches by the rough fingers of men,

They gently caress my pussy for at least 15 minutes before having me fucked, thereby making my experience an enjoyable routine rather than a sort of forced torture, as most boys tend to make it to be.

Mature men have a skill that young men seldom have, and that is whole body massage. They know where my sensitive spots are, and they use their fingers to gently meander all over my body, first my breasts, then my nipples, and that is followed by hand strokes over the insides of my thighs, and licking of my cheeks ...those on my face, and those on my butt...which make me feel  so very hot.

Young boys seldom even both to do all these pre-penetration manoeuvres,  and their straight, almost brutal,  penetration WITHOUT FOREPLAYS really hurts me, not just my body, but deep in my soul.

For such foreplay, so gentle and caring, make me feel like a human being, not a human toy. Most of my teaching colleagues and teachers are capable of doing such foreplay, and for that I am most grateful to them.

My teachers and former teaching colleagues have been told that although I WAS an educated male secondary school teacher, I AM being 'de-educated' to become an ignorant and stupid child who will willingly get down on my knees to be disciplined by men. 

So although I am not allowed to read or write (except for blogging on my escort experience on the Internet), I am encouraged to acquire those skills normally mastered by little children, such as drawing cartoons. My clients  will draw cartoons on the blackboard for me to do imitation drawing, and because  throughout my school years I concentrated on reading and studying ...I seldom did any cartoon drawing...I don't usually do cartoons drawing very well, and the cartoons I draw are really not so nice.

 I have to draw on the blackboard  butt bare with my panties down, getting ready to be spanked if my clients find that my drawings are not satisfactory. My students  do  mercilessly spank me really hard if I don't do my cartoons well...leaving lash marks on my poor butt...but my teachers and former colleagues...as mature men...just gently pull down my panties and have me GENTLY  hand spanked only. Oh,  they are so gentle and kind, these mature men, and I DO love them !

Mature men are generally more patient with me even if I don't succeed in getting them hard within 15 minutes. My students...those naughty boys...would have me spanked if they don't get hard in 10 minutes, saying that I don't work hard enough.

But my teachers and former colleagues would just sit there, reading or just taking a short nap, and then I get down on my knees to have them sucked off, gradually and tenderly. 

They keep saying, 'Don't worry, dearest, even if I don't get hard it isn't your fault...you won't get spanked for that.' Which sets my heart at ease, so I lick and lick....suck and suck...and eventually bingo, that naughty penis of my teachers and colleagues does eventually get hard. I like mature men for their patience and understanding.

I love having sex with mature men in the age group from 30 to 55. Most of my teachers, and some of my fellow-teachers...colleagues at the teaching staffs of the secondary schools I used to teach at....are in this age group.

 I like them for the lovingkindness,  tenderness and gentleness while in bed, which is very much unlike the BRUTALITY  and near BESTIALITY which most young teenagers show while I am required to serve them. Most teenagers have watched too many porn videos online for their own good, which means that it isn't realistic to expect me to do for them all those things they see on videos.

Yes, weird acts almost like dreamy unreality or fantasy could be forcibly performed, but those  will be  done under duress...I am so afraid of being whipped butt bare.... but they are done very much against my own will, and for that the whole situation of  fun, pleasure and  that ecstasy of mutual sharing  which lovemaking is meant to give  both me and my clients is gone, literally being trampled into oblivion.

I am intending to write about my experience with mature men...mainly my teachers and former colleagues at school....and although they form less than 30 per cent of my clients, they give me 90 per cent of my joy at work. 

I hope my writings won't bore you, but I trust that you will forgive me for that....please do forgive me for my poor writing...I know that I am stupid but writing gives me such joy because being locked IN much of the time, almost 24/7, is soooooo boring, and I am not allowed to read or write, blogging is the ONLY activity I still have with which I can seek release to my tension in my long training to be a soft, gentle, obedient, dependent  and STUPID female slave. 

(Me - having sex with one of my secondary school teachers. He used to teach me English and he tells me over and over again he likes me a lot, both as a bright language  student and now as an obedient escort.

He has me booked at least once a week, and when he first met me....when I still had a penis, but castrated...he offered to buy me out from the night club, so I could re-start my life as a male teacher. I told him it was too late, because I had committed the crime of embezzlement, and  I would be sent to jail on the basis of the evidence collected  if I didn't work as a shemale escort. He pities me so, and gives me tips...extra fees...to help me pay off my debts. Although I never get those tips...all money must be surrendered to the club manager....I  sincerely thank him  so very much for his love and understanding.)

Most of my teachers... and some of my colleagues at the school where I used to teach as a male teacher... are in the 35-55 age group, and I find them delightfully gentlemanlike while having fun with me. 

At the time when I still had a small penis....but no balls....they would just gently patted me on my penis, and some actually licked it and tickled it saying that it looked very cute. When I asked for permission to get hard while being touched, caressed or tickled at my penis, that permission was ALWAYS granted. 

Now that I no longer have a penis, my teachers and former colleagues would just gently lift up my skirt to see that little penis clitoris...which is what remains of my poor pee pee...and they often kiss it, saying that it is exquisitely pretty. 

That makes me feel so glad, because I like men to say that my poor little penis is pretty.