Tag: crossdresser sex

Part I: Happy Hour

Part II: Happier Hour

“Don’t you look delicious,” Chelsea whispered to Carla, who just exited the bathroom.

“Oh really?” responded Carla, bashfully.

Jenna walked over from the kitchen with a stiffly made screwdriver in each hand and handed one to the both. She then took a quick glance at the sexy bra, panty and pantyhose ladened Carla and gave her a flirty nod of approval before returning to the kitchen for her own drink.

Meanwhile, Chelsea sat herself down comfortably on the sofa and motioned for Carla to join her, who did not hesitate to take a seat right next to her. Chelsea then began to caress the Wolford pantyhose covering Carla’s thigh.

“So you obviously like dressing up. What else do you like?” Chelsea asked with a grin then taking a large gulp of her screwdriver.

Jenna, meanwhile, sat herself on the other side of Carla and ran her hand through her wig, just to let her know she was there and also awaiting the response to Chelsea’s question.

“Well, for starters…,” Carla said beginning her lifelong story of the extreme lingerie and pantyhose fetishes and all the fantasies she had in them. She rambled on and on, nearly killing the sensual mood between the three. Luckily, the screwdrivers were keeping Chelsea and Jenna afloat, but just barely. That was until Carla got to the part about her fantasy being pantyhose bound and raped.

Chelsea’s and Jenna’s faces lit up.

“Well, we happen to like that too dear,” said Jenna, who got up clutching Carla’s hand and lightly pulling her towards her and Chelsea’s bedroom. Chelsea got up and followed them into the bedroom, drink in hand.

“Lie down on the bed,” said Jenna, to which Carla happily obliged.

Jenna then went to a drawer pulling out several pairs of worn pantyhose. Chelsea put her drink down, kicked off her stiletto heels then slipped out of her black minidress revealing a stylish black camisole, thong panties and, of course, her own natural shade of Wolford pantyhose underneath. She then grabbed a pair of the worn hose from Jenna and began tying up Carla’s legs wrapping them tight.

Chelsea took another pair of the hose and tied up Carla’s wrists behind her, then stuffed the last pair entirely into her mouth.

“Oh look, isn’t she so cute,” Jenna said to Chelsea with a wink. Carla was enjoying every moment letting out a girly whimper to communicate her joyously bound predicament. Jenna then slipped out of her own heels and dress revealing a more slutty blue shelf bra, exposing her “breasts,” a matching thong and the seemingly required pantyhose, her brand being Pierre Mantoux.

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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.

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