This is a flashback for my Sissy Calendar caption "Miss June"
“One extra large package just for...” Jimmy announced as he stepped off the elevator. “...Oh! It's you...” He instantly dropped the act upon seeing that the only person behind the ShackUp Lettings reception desk was the stony faced and significantly overweight Matilda. The boring cow was the kryptonite to his charms and an instant buzzkill. While he loved flirting with the other receptionists, especially the long-serving Ellen, who even after all these years was still his favourite, there was just something about Matilda that stopped the Jimster dead in his tracks.
“Ellen's not here today,” Matilda stated flatly, watching the courier slide the parcel silently onto the front desk. He was unable to meet her eye as he fiddled with a handheld device for collecting receipt signatures. The scrawny man appeared completely dejected by her presence. “Ellen, was talking about you yesterday though actually.” She said suddenly, her voice uncharacteristically bright. Jimmy's head shot up to attention. “She was saying how you're always asking her out – and that she has said 'no' about a million times.” Jimmy's gaze dropped back down to his device. “She said you do absolutely nothing for her. Except...” Now she had the courier's attention. “Except...this one time about ten years ago you posed for a charity calendar. You were Miss June, I think. Ellen showed it to me. She still has it, you know? Just that month, of course. I can see why. You were very cute. She said she bought a joke book to keep the banter going between you two, but you weren't interested. She said you were embarrassed. It's a shame really – sounded like she was willing to make a go of it if you had been willing to embrace your feminine alter ego.” Matilda used her finger to scrawl out a signature on the electronic screen. “Hey, how about I talk to her? Maybe she would give you another shot? What do you say? Would Miss June be willing to bring out an early summer?”
Three days later and Jimmy was waiting in a booth at a local bar, his heart thudding in his chest. You could say a lot about the courier, but you couldn't say he wasn't punctual. The wig was the same one from ten years ago. He had left the offices in such a daze that day, he had forgotten to remove it on the way out. The rest of the outfit was new though. He had guessed the sizes and ordered online, yet the hot pink playsuit fit him like a glove. It had taken him four hours to get ready but it would all be worth it if it got him some action with Ellen. The makeup had been the hard part. All the YouTube tutorials in the world couldn't steady his hand as it held those tiny brushes, and he had left trying to walk in the heels until far too late – badly underestimating how much practice it would take to be able to stride confidently into the bar. Though again, this was just a means to an end. Once Ellen got to know him, he wouldn't need to bother with all this crap.
“There she is!” A confident female voice proclaimed from the opening of the booth. Jimmy instinctively took up a defensive position, his hands stretching wide and pressing back into the sofa and his silk stockinged legs sliding up onto the leather. “There's my date!” Matilda said matter-of-factly. “There's my Miss June!” She stood over Jimmy imposingly. “Come on, sweetie, let's go get a drink in you!” She licked her lips hungrily. “I have much to get in you by the time this night is through!”
