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🕑 Added 2021-01-13 19:15:36 +0000 UTCWednesday the following week, after a busy morning, trying to re-organise Mr Hopkin’s schedule, so he could free up his afternoon to play golf, Tammy entered the office breakroom to make himself a coffee and take a well-earned 5-minute break. He had barely stepped foot in the door, when he heard her voice, instantly knowing that he was not going to get much of a break after all, “Tammy babe, how are you? It feels like we haven’t seen each other in forever”.
“Oh, hey Jill, I’m doing fine, pretty busy, but fine, how are you? I heard you were feeling a bit Ill the last few days”? Tammy asked Jill, who stood over by the coffee machine.
“Oh, I’m feeling much better thanks, just a little tummy bug, all better now, hey, don’t work yourself to death hun, I told you before, work smart, not hard, a little smile here and there, a little flutter of those sexy lashes and you’ll have that boss, taking orders from you”, Jill said pouring herself a coffee, “by the way, did you want me to make you a coffee, while I’m over here”?
Tammy smiled, “eh, yeah sure, a splash of milk, and no sugar please”.
“Coming right up hun, why don’t you take a seat and I’ll bring it over, we can have a little catch-up, I’m dying to know what brought on the new look”.
Tammy smiled again, before strutting over to the purple lined sofa on the far wall, he tucked his tight skirt beneath his legs and eased himself down onto the sofa, feeling the velvety material rub against the back of his legs through his sheer black tights, sending a shiver up his spine.
As Jill pottered about in the makeshift kitchen to his right, Tammy placed his hands neatly on his knees, which were pressed together tightly in a very feminine manner to avoid showing his panties with his short skirt riding up rather high on his silky thighs. Sat there waiting he thought about Jill’s comment, more than just his hair colour had changed since the last time he had spoken to her, and it all seemed a bit of a blur.
After a miserable Saturday evening humiliated in front almost everyone he knew, accompanied by Maddison, the two had left the party early and taken a taxi back to Tammy’s house, It was late when they arrived but with Maddison’s help, he packed a bag containing some outfits he would need for work along with a few other essentials, before taking another taxi straight to Maddison’s. He felt a little guilty about not telling Monica before moving out, but he just couldn’t be around Sarah anymore, their relationship was just too unhealthy.
Waking up on Sunday morning, Tammy felt disoriented at first being in a strange room, but as his eyes adjusted to the morning light, they fell upon the figure of Maddison sleeping soundly beside him. He smiled, as she lay there, snoring quietly, he couldn’t help thinking how ironic it was, that for years he had dreamed of spending the night in Madison’s bed, but having finally made it there, they hadn’t had passionate sex like in his fantasies, but instead had just chatted and cuddled a little before falling asleep next to each other, like a couple of girlfriends.
After a light breakfast, Maddison asked if there was anything, he wanted to do that day, and only one thing came to mind, he wanted to get rid of the ridiculously girly pink hair, that sat tied up in a messy bun, atop his head, so with a quick call to her sister, he spent his second day in a row, in a beauty salon, getting the works.
His thoughts were interrupted by Jill, placing two mugs of coffee on the small wooden table in front of him, before sitting down to his right, “So, why the change”? she asked, “the lilac hair looked so cute on you”?
Tommy thought about how he should answer as he looked down at the wavy brunette hair cascading over his right shoulder. He kept telling himself, that he had gone back to his original colour to reclaiming a little of his old self, but that only told half the story, it didn’t explain why it now extended past his shoulders or why he had spent 45 minutes that morning curling it.
The truth was harder to admit, sat in the salon chair, he could have asked for any look he wanted, he could have asked Chloe cut it all off, but instead he had been drawn to a picture on the wall. The girl in the picture had looked so happy and sophisticated, and without thinking, he had asked Chloe to make his hair look just like hers.
It would have been hard for him to imagine a few months ago, that he would choose to dress and act like a woman but sat there next to Jill in his sexy office outfit, there was no hiding from it, some part of him liked looking cute and attractive. No one had forced him that morning to put on the revealing outfit he now wore, he could try and lie to himself, and make excuses like the little miniskirts and low cut tops, he had been wearing all week, were necessary as part of his job as a secretary or that he was dressing that way because Jill or even Mr Hopkins expected it of him, but the truth was, these days he really didn't care what anyone else thought of him, he had chosen his current outfit because it made him feel powerful and important. He had even chosen to wear towering heels every day that week, putting up with the pain and inconvenience, as strutting about the office, atop a pair of tall stilettos made him feel confident, he also liked the way they made him taller than everyone.
“I guess I just fancied a change”, he said wrapping his finger around on of the locks and giving it a twirl with one of his shorter but still long black nails.
“Well, it looks great, “Jill replied, “but being as pretty as you are, you could probably shave your head and still drive the boys wild”.
“Ha, yeah,” Tammy mumbled feeling awkward talking about men, leaning in to pick up his coffee mug from the table.
“Speaking of boys, anyone on the radar”? Jill asked probing.
“Err… no, no one”, Tammy answered rather bluntly.
“Really”? Jill replied surprised, “Well we can’t have that! That settles it, this weekend, we’re having another girls night out, I know last time didn’t work out as you’d hoped, but there are plenty of good guys out there, we’ll find you your prince charming, you’ll see”.
Tammy looked down at his wrist, at a watch he wasn’t wearing, “oh, is that the time, I better get back to work, Mr Hopkins is probably looking for me, can I think about it and let you know tomorrow”? he said standing up.
“Sure, thing hun, but there’s no need to worry, this time old Jill promises to look after you”.
Back home that evening, huddled up and cosy on the sofa, in a comfy casual outfit, glad to be out of his restrictive work outfit and tall heels, Tammy told Maddison about Jill’s suggestion.
“Do you want to go”? Maddison asked after he finished telling her the story of the encounter.
“Not really, I mean, I guess I feel a lot more comfortable with the idea of going out these days, now that I’ve done it a few times, but I’m not sure Jill is a person I want to be getting to close to”.
“Yeah, she sounds like a nightmare, just tell her you don’t want to go”, Maddison replied.
“I would but It’s not that easy Maddy, you haven’t met her, she’s like a dog with a bone once she gets an idea, she won’t give up unless I give her a good excuse”.
“Well, the offer to go to my cousin's wedding, this weekend, is still open, I know you said you didn’t want to go as you don’t know anyone, but to be honest neither do I really, I haven’t seen anyone from that side of the family in years, you could come and keep me company”?
There are only two parts left in Tammy’s tale, and this will be the last vote, so vote wisely as your decision will decide Tammy’s future.
1. Tammy finds a man he’s interested in at the wedding.
2. Tammy gets together with Maddison at the wedding.
3. Tammy doesn’t find love at the wedding but has a good time.
