Two years ago when I resurrected my punting career (after a break of some twenty years) I went at it with gusto and dedication, and resolved to try out whatever the punting world had to offer. I have done black and I have done white. I have done Indian and coloured and oriental.I have done MILF and I have done GILF...and girls that are too young to get their driver’s licenses. I have tried French and Thai...and Greek! Muffing, OWO, 69 and every other position imaginable. BBW and stick slender and preggie. Upmarket and street hookers, quickies and an all nighter. Once off visits...and visits to wonderful gorgeous sensual ladies that I have been back to fifteen or more times. Massage with FH. ‘Rub and tug’ doesn’t do it for me...and I am really not into doubles and bdsm and golden showers and stuff like that, but who knows...I may yet try them out. That’s what makes the world of punting so infinitely alluring...the sheer tantalizing and gob smacking possibilities that are available.

And there is one corner of the punting world which I am yet to investigate and explore...the mysterious yet very alluring world of the She-Male!

The She-Male! A title that elicits reactions ranging from revulsion, disgust, horror and disdain...to lust, adoration and obsession. It seems that men either love them...or they loathe them! But whatever one’s reaction might be, one certainly cannot ignore them...they are as much a part of the punting world as up-market brothels, condoms and darkly lit street corners.

And so, over time, I have developed an interest and a fascination for the She-Male. I’ve done the research, I’ve done the googling, I’ve followed the threads on esa, I’ve watched the porn. It’s now time for me to try out the reality!

I have only one concern though! IT IS MY OPINION...and nothing or no-one can convince me otherwise. A She-Male was born with the XY chromosome...and so was born a boy. A She-Male has a dick. A She-Male has testicles and sperm and a scrotum. So a She-Male is a MAN!! No amount of sugar coating or body sculpture or exquisite lingerie or hormone replacement therapy or pretty words can alter that very basic fact. (And NO, I cannot believe that a fabled ‘Third sex’ exists!! That is about as realistic as unicorns and pixies and minotaurs...and Gollum!)

So, if I want to satisfy this compulsion that I have to visit a She-Male, I have to be able to accept in my own mind that I am about to visit and have sex with another man!! No matter how feminine, no matter how pretty, no matter how lovely, no matter how sensual ‘SHE’ may be...‘SHE’ is still a ‘HE’!!!

And I’ve given it lots of thought too!! Why this interest? Why this fascination? Why this need to visit a sexy looking ’woman’...that really amounts to being a very feminine man? Am I gay? No I don’t think I’m gay...I really see nothing sexually alluring in the common or garden variety of man! I’m actually revolted at the thought of touching another man’s dick, or kissing another man...or even holding hands with another man!! Gay men are mildly interesting and quaintly irritating...but hold absolutely no sexual allure or interest to me at all! And I love and adore women...every sensual sexy succulent wonderful molecule of them!!

So why She-Males? I cannot answer that…I really don’t know, I cannot understand my interest...I just know that I have to test the waters!!

And so test the waters I will!!

So I make the booking!! Friendly, helpful, very professional on the phone. Feminine voice, a little husky, a little gruff, a little high pitched, breathy. My follow up calls and messages are handled perfectly. Excellent first impression! I laugh when SM tells me about being stressed because all the nail salons nearby are closed. SM really wants to impress me with pretty shiny new nails...such a girl!!

I tap on the door! Hollow feeling in the pit of my stomach...what the hell am I doing coming to pay for sex with a MAN? My cock is shriveled high up between my thighs in consternation, confusion and panic!

The door opens slowly...and there stands SM in full glory!! Tall, very tall, slim, wide shoulders, boyish hips, long coltish legs, tight strong butt, flat chest...a MAN ! Dark ebony skin, clear and incredibly smooth and hairless, long black hair, large gold hoop ear-rings, bright high stilettos, pink lacy lingerie, tiny g-string...a WOMAN!! Not at all unattractive, very manly but at the same time extremely feminine! Big eyes, face rouged and painted. Long eyelashes! Lovely smile, sensual lips, very white teeth...and totally welcoming! SM invites me in with a huge wet kiss to my lips!! OMG! What the fuck am I doing here????

And so to business. This very manly SM is also extremely feminine! A contradiction in terms but that’s just the way it is. And I am nervous, extremely nervous! But SM has seen this all before...and soon has me relaxed and comfortable...and rearing to go! We explore and caress and laugh and chat and breath heavily...and explore some more! Very few working girls have kissed me quite as lavishly and as affectionately and as intimately!

I am knelt between SM’s splayed legs, nuzzling and nibbling the svelte polished skin of the upper thighs and belly and torso and crotch. Very aware of the tightly packaged silky pink g-string just millimeters away from my mouth. SM sighs and giggles coquettishly as I kiss and nibble...and something starts to grow and swell beneath the pink silk of those miniscule panties. It gets bigger and fatter...and uncoils and straightens and quivers and forces its way out from under the fine panty. A man’s cock!! Thick and black and engorged and huge! The foreskin rolls back and the glans is slick and ebony and polished and filmy with pre-cum...MALE!! I move my mouth towards it and part my lips...I am as horny as all fucking hell! SM giggles, delightfully, enchanting, sensual, aroused...FEMALE!! I slip HER cock into my mouth...

And the rest is, as they say , history!!

And so I have lost my She-male virginity! And if I am now gay because of that...so be it!!! I am a convert...totally and completely and without a shadow of a doubt! This MAN who is a WOMAN has just indulged me in one of the most erotic experiences of my life!!

Would I go back? Hell YES!!! I already have an appointment set up for 7:00 pm tomorrow evening!!

Yet I still can’t make up my mind!! Is SM a man, or is SM a woman?

Either way, DOES IT REALLY MATTER?

Go check it out for yourself!

Good post!

Well done WW, good on you i always say do the things that make u happy.

Wow enlightening and informative

Excellent post. Very thorough. ..

Once tasted never wasted, but no thanks not my cup of tea

Great post....the final frontier indeed....I don't think I have the balls to try it out but I am extremely curious.

An exoticness, a uniqueness, something that can’t be obtained elsewhere. They’re just totally unique in their sexuality in that they’re both… men and women and at the same time, neither men nor women. That might be the fascination.

@ WW,
I started the punting game about 3 to 4 yrs ago. What you described above is pretty much my punting story, you just say it much better.
Was also curious on the SHE male issue, and tried it once. Will I do it again? Don't think so. Why not?
- Them answering in a HE voice
- The she-male I visited was built too masculine for my liking (I like the ladies I visit also to be more on the petite side, I want to handle them, and not vice versa).

Without wallowing in a verbose stream of self consciousness as WHITEWHITE hath been pleased to favour us with, I have no mental hang ups about treating myself to an amorous intrigue with one these delectable creatures.
In fact last night I made good my promise to visit SM Marry again.
She fairly swallowed my cock.
And she treated me to the deepest French kisses the likes of which I have never before experienced.

So let not the censorious and carping tongues of detractors dissuade you.