Jack

 

 

Darlene was the manager to the cosmetics outlet attached to the warehouse where I worked.

She was in her late 30s, maybe even early 40s, but was drop dead glorious.

Jack was a scrawny kid just out of his teens, who drove part time for the company making deliveries.

He had the hots for Darlene just as we all did.

I never hit on Darlene but a number of the other warehouse employees did, and got rejected.

Jack was the only one she paid any attention to, inviting him into the outlet during breaks or after the warehouse closed its doors for the day.

She showed him around the outlet, let him sample perfumes and other things, and he followed behind her like an adopted kitten.

To say the least we were insanely jealous, and teased him merciless as to whether he got to first base, or maybe beyond.

He never answered the question, simply saying she was like a sister to him, with the rest of us thinking if we had a sister like her, we’d still want to fuck her.

The more it went on, the worse we got, so jealous of Jack a number of us stopped even talking to him.

None of us at the time took note of the small changes he was undergoing; maybe we didn’t want to; he dressed better if a bit oddly, wearing female slacks, jeans and flat shoes, rather than his previously grimy t-shirt, jeans and sneakers. He had even let his hair grow.

I began to suspect something when I saw subtle touches of makeup, eyeliner, shadow, and just a little pink on his lips. I also noticed that Darlene started to refer to Jack as Jackie.`

At one point, as he waited for us to finish packing an order he needed to deliver, Jack and I bumped into each other between some of the racks, where I asked him what the hell was going on.

“What do you mean?” he asked, seemingly legitimately baffled.

“I mean the girly clothes, the eye liner and god – the lipstick.”

“You don’t like it?” Jack asked. “Darlene told me you would.”

“What the fuck does this have to do with me?” I asked, perhaps a bit too harshly.

Jack’s mouth snapped shut; he walked away.

I went to talk to Darlene, who remained very aloof.

‘It’s not something I’m at liberty to talk to you about,” she said.

“But from what I’ve heard, you talk to him about me all the time.”

“I don’t talk to him about you, he talks to me,” she said.

“What about?”

“As I said, I’m not at liberty to day,” she said. “Maybe you should talk to Jackie yourself.”

“I did talk to him,” I said. “I get the impression that he’s dollying himself up to make himself more attractive to me.”
“Does it? Darlene asked.

‘Does it what?”

“Make you more attracted to Jackie.”

“I’m not gay.”

“Which is why Jackie came to me, asking me to turn her into a girl.”

“You can’t turn a guy into a girl,” I said.

“I can. Or at least someone as close as possible,” she said matter of factly, as if she had done something like this before, and from the smug look and that slight darkness in her eyes, I believed she had.

“What happens if you succeed and he finds out I don’t want him in that way?” I asked.

“How do you know you won’t,” Darlene asked, looking me straight in the eyes. “You haven’t see the finished product yet.”

I told her she was crazy and went back to work, doing my best to avoid Jack, though with business picking up, he got assigned to help us pick and pack orders, putting him within earshot all day, and leaving the scent of his perfume wherever he went.

Darlene apparently decided to up the anti. All subtly vanished. Jack came in dressed in a short skirt, stockings, and bright red lipstick, creating a huge amount of havoc among the other workers, who were either disgusted or more often, attracted, men who then found every excuse to get close to Jack whenever they could, while I did the exact opposite.

It got worse. Jack suddenly developed tits, and spoke in a voice so feminine I even sometimes mistook him for a girl.

A few of the crew were so upset about all this, they wanted to take Jack out into the woods behind the warehouse, and would have beaten him senseless had I not intervened.

I went back to Darlene.

“You’ve got to stop this,” I told her. “Jack is going to get hurt.”

“Jackie wants this,” Darlene said. “Besides, it’s too late to stop.”

“What do you mean?”

“Jackie has been taken hormones and getting other treatments,” Darlene said. “And she’s scheduled to go into surgery next week.”

“You really are crazy!”

“It’s what Jackie wants.”

“But it’s not something I want, so if he’s doing this for me, he’s wasting his time.”

“It’s not about you anymore,” Darlene said. “If you don’t want her, there are plenty of others who will.”

That’s when she told about Jack’s giving blow jobs and doing anal sex in the men’s room with the boys.

“If he gets caught, he’ll lose his job,” I said.

“It’s a risk we all take,” Darlene said. “I won’t ask her to stop doing anything that makes her happy.”

Due to the surgery, Jack was out of work for several weeks. I thought things would get back to normal when he got back, when the opposite was true. During her absence, many of the guys moped around, it felt like a wake.

When Jack got back, they treated him like a star. At that point upper management got involved, realizing they had a very pretty girl working side by side with a pack of overly horny men.

Jack got transferred to the outlet to work with Darlene, while each day at lunch or breaks the boys went over to outlet, brining Jack small gifts.

“You can’t tell me Jackie isn’t better off now than she was before,” Darlene told me sometime later. She’s never had so much attention.”

“I suppose not,” I said, although I still wished for the old Jack back, something that seemed to transpire when management hired Jack’s replacement, a kid as scrawny as Jack had been, but to my dismay, the new driver attracted Dalene’s attention.

 

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