WEAR HER MAKEUP (PILLAR OF THE COMMUNITY by Janine)
I’d noticed a guy at the sex club’s bar – and I was feeling Ohhhh so
hot. He was smiling and shamelessly taking in my careful makeup,
my shimmery and strappy little halter dress, my thigh-highs and my
impossibly tall, cum-f***-me heels. We smiled at each other and,
predictably enough, he send over a drink and we started talking.
At one point, after he’d been talking to me for about five minutes, I kidded him that he’d spent the entire time looking at my cleavage– and I reminded him there were even more surprises under my dress. He smiled, took my hand, and placed it on his pants letting me know he already knew about it. I laughed and grabbed him by the
back of the head and gave him a breath-taking French kiss and as I ground my torso into his, pushing my groin and my breasts against his body, I could feel him stiffening.
After what seemed like forever in this groping embrace he suggested we retire to a corner to do, well, what it is you do in dark corners of sex clubs. Within minutes he had undone the dress’s halter top and my panties were down near my knees – and as I fondled his cock, he ran his fingertips along mine. He told me he’d fantasized about doing a tranny gurl since – forever -and now, he was finally about to do it.
He was deliciously slow – both in offering as much foreplay as
anyone can expect at a sex club and in achieving his own orgasm.
When it was clear he was about to cum in my mouth, he was so
wonderfully sweet and asked if I wanted him to pull out and squirt
elsewhere. I mumbled no and he beamed back at me with a
thoroughly satisfied look on his face after he’d cum and as I looked
up at him and lovingly sucked clean his cock and balls.
And that’s when he invited me to his house. We drove across the
bridge to Berkeley and I remember thinking he was familiar (and I
was really hoping he and I hadn’t done this before and I’d simply
forgotten his name!) We got to his place – a huge mcmansion of a
place so high in the East Bay hills you had a view of an amazing
stretch of San Francisco Bay. It was too late to see much, of course,
but the beauty of the lights and the dark outlines of the hills in Marin
Country was simply gorgeous.
He opened the front door, disarmed the security system, and turned
to me and said “and you, my darling little pussy gurl, can be my little
wife this evening!”
darling, it may be small its going inside of you !!!
He took me by the hand to the bathroom in the master bedroom. On
the counter were, obviously, his wifes toiletries – perfume, makeup,
combs and curlers.
I was more than a little surprised. Guys usually don’t treat their
married status so casually …
He said “I’d like you to wear her makeup.”
So that was the game! I was to become this very sexy man’s
mistress while wearing his wife’s makeup. I was to wear her makeup,
her fingernail- and toe- polish, her earrings and a pair of her panties
and both suck him off and take away his male virginity in their
bedroom – in their bed.
As the evening wore on I learned his wife was a very successful
lawyer who travelled extensively. And that she was sexually
disinterested, and, of course, that she had no idea her darling
husband had this particular kink.
I also learned why he seemed familiar. The man I had just heard
screaming as he was penetrated for the first time in his life was, truly,
a pillar of East Bay respectability. Wealthy. Widely admired for his
philanthropy. And, always, the very image of a devoted husband.
I learned that he wanted to do ‘this’ again – that he wanted to have
copies of some of his wife’s clothing made so I could wear ‘her’
During this last year he has escorted me several times to a fabulously
queer-friendly – and discrete — seamstress in San Francisco. Each
time I leave her apartment carrying an armload of outfits that are
perfect copies – well, maybe a little sluttier — of his trophy-wife’s size-
And on those evenings, our playing is always the same.
We go back to his house and I do my wifely transformation. And each
time it’s a different room where he pretends to ‘discover’ my little
secret, where he pretends his wife does things he’s only dreamt of for
years. Each visit is a time when he pretends to discover a new kink.
Our evening in his kitchen was the night he discovered he likes to
wear nipple clamps. Our visit to the sunporch was an opportunity
to react as though he was being date-raped, the living room, an
exploration of seeing just how excited he got as I ‘forced’ him to wear
a pair of adhesive breast forms.
The only other constant in all these visits is that I leave his house
before dawn. His bedside alarm rings at 4 a.m., we shower together
and I climb back into whatever sexy little outfit I’d met him at the
door with the night before. There’s always one last sucking off in the
house foyer and … that’s it til the next time he gives me a call.