Part 1: Happy Hour
Carl was just finishing up his work at the National Bank downtown. Normally, he would just get in his car and drive home but this particular day had taken a toll. Refinancing, mortgages and loan defaults… pretty much all of the negatives of his job happened to have come in a flood to which he grudgingly worked through it all.
Relieved after exiting his work, he made his way to the bar just a block away and ordered a stiff martini to unwind. Not a frequent occurrence since, besides not being much of a drinker, he had a wife and a five year old daughter waiting for him when he arrived home. He, however, sipped his martini without even a wince as if he’s done it at the end of every day of his career.
Truly tempted for another stiff martini, Carl exercised his restraint, paid for his drink and exited the bar. On his walk to the parking garage, though, he encountered a pair of provocatively dressed women who he could tell were transvestites, albeit very beautiful and convincing ones at that. Normally, he would have given them a flirtatious wink and walk right past.
This time, given his slightly inebriated state, he stopped in front of the two noticing their lovely legs in pantyhose and striking high heels.
“Wow, I just love those heels!” he exclaimed, not to either one in particular, and succeeding with his “pick-up” line as the two transvestites looked back at Carl, utterly flattered.
You see, underneath the suit and tie of that nine-to-five day worker hid the other side of Carl, Carla by his (or shall we say, her) own naming, and her oh-so guilty pleasure of closet crossdressing. She loved it all: lingerie, pantyhose, dresses, wigs, makeup, you name it. She could wear them like a pro, or like the two beauties in front of her.
Acting out her own crossdressing fantasies, however, turned out to be quite the challenge. Carl’s wife, Amy, was a very conservative woman who was the type that would never deviate from the same missionary sex, over and over. That meant no toys, no doggie-style and definitely no crossdressing on the part of Carla.
Carla even went as far as to keep her entire wardrobe of women’s clothes, underwear, shoes and accessories in her secret rental storage space nearby where he worked downtown. There was no way in hell she would let Amy or his daughter catch her in the act at home. Unfortunately, this also meant her crossdressing was strictly kept to the confines of the storage where she would pose dolled up in front of the mirror installed on a wall and wank one out before she left.
Yet given Carl’s schedule at work and his duties at home, times where he could escape as Carla were few and far between. As well, his sexual frustration for his beloved fetishes often mounted day by day to the point where it completely obsessed his mind and he was likely to do something out of character, which really meant against the conservative nature of his wife’s wishes.
Take, for example, drinking a martini and chatting up a pair of transvestites…
Chelsea and Jenna introduced themselves to Carl while giggling in their flattery of his flirty comment.
“Oh, and I love men in suits,” Chelsea says while flirtatiously grabbing Carl’s tie and pulling it toward her.
Jenna followed her lead, gently touched Carl’s face and asked, “So like like us ‘girls,’ don’t you?”
“If you only knew,” Carl replied. “It’s my dream to look as gorgeous as the both of you.”
Chelsea and Jenna stared back at Carl, speechless but curious.
Carl, meanwhile, couldn’t believe the words that came out of his mouth. Then again, he couldn’t believe the two were flirting back at him which excited him like nothing ever before. Against all his instincts as the straight and narrow husband and father, he decided to see where this could lead.
“Can I invite you ladies for a drink?” he asks them.
Jenna didn’t hesitate,”Sure, let’s go to The Vine just down the street.” Chelsea silently agrees. No need to convince Carl.
The three then proceeded to walk The Vine bar, an easygoing place for all walks of life with Carl ordering his second martini and Chelsea and Jenna ordering each a screwdriver. Then, as if he were seated on a therapist’s sofa, Carl proceeded to tell his whole life’s confessions on his crossdressing fetish. Everything from stealing his mother’s pantyhose as a kid to her fantasies of trists with other crossdressers bound and gagged and, yes, even her secret storage stash located nearby.
Chelsea and Jenna, meanwhile, sipped their screwdrivers and listened to every last word. The both even offerred their support, telling Carl of their own experiences in crossdressing and eventually becoming full-time transvestites. Within a short span of maybe half an hour, Carl suddenly bonded with the two and felt a massive relief that he could finally express himself as Carla to someone other than herself.
Of course, there are more ways than one to express one’s self, as we would soon find out…
“Can we see your treasure trove?” Chelsea asked Carl, referring to his secret storage space (and possibly more). Jenna also looked at Carl waiting for an answer.
“Why… certainly,” Carl responded as he got up and paid for the drinks. The three then walked to his storage space just another block away. Coincidentally, it happened to be next door to the apartment building where Chelsea and Jenna lived as roommates (and occasional lovers).
Carla, unlocked the door and flipped on the light switch revealing her feminine mecca: a closet full of sexy dresses and high heels, a large drawer filled with lingerie and pantyhose and, on top, her makeup tray with a mirror hung on the wall right above it.
Jenna, instinctively started grabbing a couple of the dresses, an unopened pair of Wolford pantyhose, various bras and panties then a pair of heels that happened to catch her eye. Chelsea reached for a dress of her liking and held it directly in front of Carla.
“This will do,” she says approvingly.
Without a word, Carla sensed what was in store next. Sure, she had thought about it for a moment that he has a wife and child at home waiting for him, yet at that moment, she was finally free to be Carla which was exhilarating and definitely not something he was going to put an end to. Not right then anyway. She just went where the flow was taking her.
“Ok, time to go to our place dear,” Jenna says while walking out of the storage area. Carla turned off the light and locked up the door. Chelsea then reacheed for Carla’s hand, and held it, her chosen dress in the other. Then all proceeded to the apartment building just a few feet away, without even a protest on behalf of Carla.
As they entered the apartment, Seemingly coordinated, Chelsea races to make a round of drinks, a martini for Carla of course while Jenna gently places the dresses, lingerie and shoes nearby. Next, Jenna handed Carla a sexy matching black bra and panty set and the pair of nude colored Wolford pantyhose.
“Get dressed,” she firmly ordered Carla as she headed off to their bathroom and closed the door.
Carla couldn’t contain her excitement as she slipped into the pantyhose, then the bra and panties and then noticing she left a little wet pre-come spot on the crotch of her Wolfords.
“Oh my god, is this really happening?” she thought out loud to herself.
(to be continued)