Showing Charles the Time of His Life

 Showing Charles the Time of His Life

A co-worker in my office is great – she’s smart, she gets her work

done, and she’s cute (you thought tgurls didn’t NOTICE??).  And

as if that isn’t enough, she’s totally cool with my gender-blending

personality.  AND, to boot, entirely Politically Correct.  Even by

Berkeley California standards.

Anna (her name) is engaged to a lovely man – a very sweet guy Right

Outta a casting call for sincere mid-western guys.  (I’m angling for

a role at their wedding –I simply love any excuse for a fitted bodice

and cleavage down to here )  Anyway, Anna suggests I give Charles

a little taste of the local kinky scene – take him to some tgurl bars,

maybe pop into a San Francisco sex club, and maybe even meet

some of my friends (including one porn star) for drinks.  Anna’s

convinced Charles should really see this side of the city at least

ONCE before they settle down to a relatively quiet married life.


The plan is simple and Anna and Charles think its great.  C and I will

do a little bar crawling – I’ll make sure noone sends us a round of

drinks and we’ll avoid the genuinely raunchy spots. I convince both of

them that a little ‘costuming’ is needed – a femme-y top, and a bit of



So – Charles arrives at my place, wearing tight dark jeans and,

frankly, already smelling like he’s had a fair bit to drink.  I have him

slip into a new top – a scoop-necked Indian cotton flared tunic looking

thing toped with a black net shrug.  (I remember thinking he’d be

even MORE adorable with a bra – but thought he’d totally freak with

that suggestion.. LOL. Oh, and some really cute little magnetic fake

pierced earrings.


Charles is looking remarkably cute and all I can do is think that if he

weren’t such a good friend’s fiancé, I’d soooooo try to seduce him!

But …  girl to gurl, I can’t. Anyway, its time for the makeup.

I sit him down at the coffee table with a table top-mirror and tell him

what little bit of makeup he’s getting for this evening’s walk on the

wild side: eyeliner, mascara, eyeshadow, lipliner, lipstick and gloss.

And maybe a bit of foundation.  And a little sparkle thrown into his


The darling boy asks for a drink – and I make him a cocktail (one of

the 4 that I know how to make) and he drinks it like a shot!   Um.

Another Sunrise for the thirsty boy.

So I’m putting on the mascara, and he’s acting very comfortable –

if still nervous.  And THEN he starts flirting.  More than flirting.  And

when he tries to run his hand up my thigh, I take his hand and put it

on his lap .  He in turn holds my hand and brings it to his crotch which

has an extremely hard cock straining at the seams of the jeans.

He smiled and whispered to me, “Janine, its been two years since

Anna introduced us and for all that time I’ve thought about being in

bed with you, about your thing in me!”  I was speechless.  Here was

the fiancé about to marry my best friend and I’m finding out he has a

kink no-one could EVER have suspected.


“Oh darling Charles, you know we can’t fuck …  I wish … “ and

I left the sentence drop because I wasn’t sure WHAT I wished –

except I knew I sure did want to have that man, naked, next to me.

Somehow, we managed to get out of my apartment and into the car.

We went to a bar and I saw one of my pro friends – another gurl

who’s been doing freelance acting and escort work for a couple of

years.  She and I went to the lady’s and I told her the story. We came 

up with a thoroughly wicked plan. We’d take Charles to one of the

city’s sex shows, the one specializing in tranny stars!

In the car ride there, we teased Charles – saying he was in for a treat

he’d NEVER forget. ‘got to the place, paid the cover charges and in a

sofa in a dark corner of the club, Candace sat on one side of Charles,

and I, on the other

We took turns at teasing him with kisses and  glancing fingers along

his thighs for the longest time.  And when the cabaret show was

going strong, I leaned down and unzipped his fly and – a little trick I

learned from, ahem, years of practise – I gently slipped a condom on

his up cock with my mouth.  Candace started stroking his shaft as I

played with his public hair.  He was sooo  exicited.  His nipples were

popping,  and he was breathing faster and faster.  His fully exposed

groin began thrusting up into the air.

And, on cue, Candace leaned over his lap, tugged off the condom

and started giving him head!

As he got closer, I leaned over from the other side, nibbled on one of

his earlobes and said “how dos it feel having someone who used to

be a man sucking you off, darling girl?”

And THAT was it.  He came with a barely muffled long moan (the

4 girls in the next sofa giggled) and he said that was the best he’d


We cleaned and prettied him up some, went on to another bar (where

he managed to keep his cock in his jeans) and at a third bar, we

joined a table of tgurl admirers – where our new gurlfriend, Charlene,

was introduced.  At the time Charlene was  giving out ‘her’ phone to

the third guy, we grabbed our new girlfriend and went back home –

where we gave her the little lecture about safe sex and lube types.


Next day at the office, I ran into Anna at the copier machine.  “I

haven’t talked to charles yet today “ she said.  “Did your little tour

shock him last night?”    Ohhhhhh…. You can be sure that darling

fiancé may NEVER be quite the same again!”  She laughed at what

she thought was a little joke, and I and I smiled at what I suspected

must STILL be going through that darling man’s head..

Charles/Charlene – you’re a natural !!!