It all started the day before Valentine Day. Paul was heading off at the end of his shift to clock out while friend David clocked in and Tony was heading for lunch. Paul heard the two guys talking and complaining. "What's up, guys?"
"Was talking to the front office." David complained. "The girls get to dress up in normal clothes while if the guys want out of their work uniforms it has to be suits and ties."
"I came to work at this store because it didn't require suits to be worn." Tony said. "When complaining to the office about how unfair it is, I was told by the supervisor I could always wear a dress if I have such a problem with the dress code tomorrow."
"Like you could stand wearing a dress a heels for a whole day." Their co-worker Millie chuckled as she passed by in her sexy shift and tall ankle-boots.
"Sounds like a challenge to me." Tony said as the three made themselves a bet - the one who could last the longest without complaining would get $100 from the other two.
That night David and Tony made a stop in the women's department of the store and bought themselves complete outfits. They noticed it was weird that the mannequin in the red Valentine teddy looked so much like his former co-worker Missy. The one that often teased the boss about his bed partners and had volunteered to join him on more than one occasion. Paul, on the other, hand was a closet cross-dresser and preferred if this sort of thing were to ever happen. He pressed a concealed switch in his walk-in closet to reveal a hidden chamber filled with women's clothing.
The night Paul did his finger nails so that they were ready when he went in the next day. After a bath and shaving his legs, Paul picked out a Valentine-red silk blouse with a black mini skirt that barely went below the hips, jet-black hose and black loafers. A flip-style wig finished his disguise. He thought about his co-workers. 'They probably don't know how to dress up but shoud be comfortable at work.'
He was right as he saw them at the office the next day. David and Tony both had shoulder-length blonde wigs. Tony wore a white blouse with a red ankle-length skirt that had a slit all the way up the side. He had nude hose and black six inch heels on. David looked as stunning in a rose pattern, suntan hose and black two inch heels. The three had no problem showing up dressed that way at work since their boss was openly gay and proud of it. However Dave and Tony were more than a little embarrased but wouldn't let something like that stand in the way of winning a quick hundred bucks.
"I can't believe you did it." Millie teased as she smiled at the three while dressed smartly in her off-white fuzzy sweater, black slacks and comfortable sneakers. "I am a girl and wouldn't come to work like that. I much prefer blue jeans and work boots to dresses and heels. You look like a bunch of cut-rate hookers..."
"I will not have you teasing the employees." Eric, the manger said, with a sly grin. "For that you can work the first shift at lover's lane. The Valentine express lane." This was always the busiest location in the store.
"Yes sir." She sighed and took her drawer to the register and signed in. As time went by, Paul grinned as he noticed that it wasn't long before David had removed his heels and stood in his stocking-clad feet behind his register while Tony kept shifting his feet uncomfortably. Tony complained about his toes while David griped again that his ankles and knees hurt as he kept shifting lifting one leg up at a time to give himself some relief. Whenever Millie came around he had to put them back on again, because staying fully dressed was part of the bet.
"I'm sure your Valentine will love the roses." Paul said as the man in a red bow tie, white shirt and black suit smiled at him and handed over a crimson red flower, along with an elegant satin lingerie ensemble.
"You tell me, my cute little Valentine." The man said as Paul stared in disbelief. He didn't know if he should feel flattered or not, and rung up the items. As he started to put the flower into the bag along with the purchase, the man said "That is yours." as Paul blushed under his makeup. He accepted the flower gracefully as well as the promise of a date after work. The group of friends met at their usual watering hole, where Paul collected the hundred dollars from their little bet. Tony also won, but Dave had gotten caught bare-footed and had to hand over the money to her.
"I can't believe you're going out with a guy." Millie teased as she closed her purse, finished her beer, and headed out. "You guys are so keen on wagering, you should bet on if he'll marry him or not."
"Why not." The braggart bgrinned and figured on a sure thing. "If we lose we'll even be your bride's maids. Ha!"
After taking a shower, Paul changed into a green sweater, black blazer and skirt with suntan hose and open-toed shoes. He thought of giving himself a polish since his toes were showing but figured there wasn't time. He wasn't use to getting ready, as a girl, for a date.
A wonderful night of dinner and dancing lead back to Paul's apartment. A kiss goodnight left Paul with the feeling of butterflies in his stomach. He loved how the man tasted and had to tell the man the truth before he lead him on any more.
Much to Paul's surprise, the fellow didn't care, and said he had suspected all along. The millionaire was even willing to finance Paul's sex reassignment surgery if he'd marry him afterwards. Paul accepted, never feeling so happy in his life. He was even given pairs of special panties that forced him to pee sitting down and feel like he was all woman as the hormone replacement therapy began to reshape his body causing him to become curvy. Time passed, and Paul had never been more at ease with himself or, soon, herself.
After a week in the hospital during which the operation took place, and a short recovery, the two were married; sure enough Tony and David were Paula's bride's maids. The reception was everything she could have dreamed of and afterward they flew to a secluded island paradise on her new husband's private jet. Paula went to bed clad in only a pajama top while her husband wore only the bottom, for only a short time as it turned out. Paula soon found it would be the last night she ever wore pajamas, period. The two sleeping naked was so much more sexy and romantic. They found themselves to truly be soul mates, forever to be in love.
While Paula was on her honeymoon, the manager asked Millie to stay work after to talk about her behavior during the whole thing and how badly she had treated her sensitive co-worker. She sat nervously before the boss while he held a conversation in hushed tones on the phone with one of the foreign-based stores.
"What are you going to do?" Millie asked as he finished the call. "Fire me?"
"Not exactly; just give you another kind of job." The manger said mysteriously as he stood up and raised his arms overhead. Suddenly, a magic wand appeared in his right hand and his suit transformed, changing into a long flowing wizard's gown. Complete with pointed hat. Feeling fear, Millie jumped up to run. As she stood. however, her body froze in position with a snap of his fingers. She could not resist as her arms posed themselves in front of her body before stiffening into place. She found she could not utter a word as her vision blurred when her eyes changed to glass and her skin to hard plastic. Within seconds, Millie had become a mannequin. "You're working overseas in display, now." Her wizard/boss chuckled, surveying his handiwork. "Yes, and a great improvement I must say." Millie said nothing.
With the wave of the wand, a pair of scaly lizard-like demons appeared, stepped up to the motionless girl, and took her apart. She was crated and shipped to Europe and the store's branch there. There she was reassembled. The magic kept her alive to see, hear and especially to feel pleasure - just up to the point of orgasm - at the touch of the clothing and particularly that of the people who dressed and undressed her. She learned across forever that it wasn't right to judge others. If you did so, you had best be ready to pay the price.