The planner and the charmer

 The planner and the charmer
by
joeberan
•03/24/2026•XL
The planner and the charmer

Lawrence felt dizzy and out of balance as he emerged from the phonebooth-sized box. Squinting and adjusting to the sudden brightness after the box's pitch black interior, he wobbled and fell forward onto a nearby bed. As he did the magnitude of what he'd done became obvious. The blankets against his soft skin. His body, jiggling in ways a man's body never did. He twisted about, looking back as his vision cleared, seeing the magnificent woman's body he now possessed.

"Damn! You might've come out even hotter than me!" Bobby tittered in a squeaky voice. Bobby was not himself either, but a pretty blond woman.

"Are you-" Lawrence attempted to clear his throat, but it did nothing to change the strange sound of his new voice, "Are you sure this is a good idea?" He felt so weird!

"Totally!" Bobby squealed, "We go over to Big D's like this and tell him we want to try his pool and he'll totally let us in! Then we just find an excuse to wander off, go for his safe, and BOOM! Priceless football memorabilia is ours! This job will feed us for a year!"

=====

Bobby was always the planner of the two of small time crooks. They'd been lucky enough that when Big D - football legend - moved in to the mansion down the street, he'd hosted a block party and invited everyone. Bobby and Lawrence had gone and immediately went snooping. Bobby not only found the safe, but the combination to it written on a post-it note in a drawer nearby! There were too many people around to rob the place that night, but Bobby had been planning a proper heist ever since.

The only problem was, the place had an intense security system and Big D's invite had been a one time only thing. Bobby had been trying and failing to find a way in for months without success, then he found that box...

He'd found in an alley behind a pawnshop. It was about the size of a shoebox, but it looked weird and shiny so he'd grabbed it. In doing so, it expanded from shoebox to phonebooth. It's ability to go between the two sizes was far from its only trick though. When it was expanded, if you touched it and thought about something, an image would appear on it. If you went inside it, you'd become whatever was in the image.

Bobby had realized how it could be part of his plan immediately. A little demo to Lawrence by turning himself into a blond woman - also part of the plan - and they were set.

=====

Big D let them right in - two hot chicks in bikinis, it was an easy decision, even if one of them did seem pretty nervous. He'd gotten called away on a phone call right after that, and had gone back into the house to take it, leaving Lawrence and Bobby - or Laura and Bobbi - lounging by his pool.

"This is so weird. Let's just go rob him now." Lawrence complained.

"Not yet, not until we know where he's going to be exactly." Bobby answered, "Try to relax. So you've got boobs and a pussy. Try to enjoy it."

"Enjoy it how?" Lawrence asked.

"Enjoy it like this." Bobby popped his tits out of his bikini and started playing with them, making Lawrence's jaw drop. "It feels really good..." Bobby smirked, then moved to the stunned Lawrence and popped out his tits too.

"Hey!" Lawrence said.

"-and this feels even better." Bobby slipped a hand into Lawrence's bikini bottom and started fingering him.
finger fucking in pool

"Oh fuck!" Lawrence gasped, still in shock, and overwhelmed by the sensations shooting through his body.

"Yeah, I gave this a try before I showed you what the box could do. Fingering my pussy was pretty awesome." Bobby explained, but didn't stop.

"Oh god!" Lawrence gasped, "Shit, what're- how-" Lawrence didn't know what to say, he just knew he didn't want it to stop. It was wonderful, and he could feel it building towards something even more wonderful...

"You're going to make me cum!" Lawrence muttered, desperate for it.

Then suddenly Bobby removed his fingers and tucked Lawrence's boobs back in his bikini, then fixed his own. Lawrence was about to complain when Bobby suddenly spoke. "Hey Big D! Laura here was just telling me what a fan she was of yours!"

Lawrence turned and saw Big D approaching, wondering how much he'd seen. He had a wry grin, but no more than he had when he'd first seen them.

"Oh yeah?" Big D plopped down at the edge of the pool, "What about it?"

Lawrence's head was spinning, his heart was still racing, and his pussy ached. It took him a minute to remember the plan. Same as always. Bobby made the plans and did the actual burgling and Lawrence was lookout and distraction. "Oh yeah, I remember your game winning pass in the Superbowl a few years back..."

Bobby stood back and watched as Lawrence chatted up Big D. Lawrence was always good at laying on the charm, which was a skill Bobby envied. As he watched now though, he realized it was flirting.

Lawrence was flirting a lot. Did he know that was what he was doing?

When Big D asked "Laura" if she wanted to come see some of his old jerseys, Lawrence agreed quickly.

Lawrence knew he was giving Bobby the opening he needed as he followed Big D inside. He was a little surprised when the jerseys were in Big D's bedroom. He was more surprised when Big D suddenly kissed him.

He was even more surprised when his body - still all wound up from Bobby's fingering - surged with desire and he found himself kissing back. Kissing back and letting Big D's hands slide across his tender body. Letting those hands remove his bikini and push him onto the bed and-
fucking in bed

"Oh fuck, YES!" Lawrence moaned as Big D pounded his pussy, any part of him that objected to it completely subsumed by the raw, primal need of his aching loins.

It was the best sex of his life. Lawrence came three times before Big D nutted deep inside him.

Finished and suddenly embarrassed, Lawrence made his excuses and left the thoroughly satisfied Big D as quickly as he could.

He found Bobby back at their place with the stupidest grin on his face, a tray of golden championship rings held just in front of his boobs. "Have a good time?"

"Oh fuck you." Lawrence was suddenly having doubts if this all had been worth it. He'd gotten fucked - literally - and loved every minute of it. That was going to haunt him.

"Don't sweat it. It's the box. It makes you super horny." Bobby explained.

"Can I please just get my dick back now?" Lawrence complained.

Bobby shrugged, setting the rings down and moving over to where he'd stashed the collapsed box.

Bobby tapped the box. Nothing happened.

Six hours of increasingly frantic banging on the box later and a bit of uncharacteristic crying, the two of them had to accept that it wasn't going to open again. They were stuck.

=====

Lawrence came back from his millionth trip to the bathroom of the day, plopping on the bed and feeling shitty as he stared down past his tits to the belly he thought for sure he'd never see from this angle.
pregnant

"How you feeling?" Bobby asked as he got ready for work, fixing his hair and putting on some makeup.

"Shitty. Sore. Angry. Horny. All the things." Lawrence complained. The months since the heist had been a whirlwind. When Bobby got his first period and Lawrence didn't, they'd known something was up.

"Well you've got a vibrator, might as well enjoy the fact that you're not working anymore."

"Oh fuck you." Lawrence grumbled.

"Hey! I am putting in A LOT of hours down at the club just so we have a place to live! Do you have any idea how many tips I have to get to support us working by myself? Do you have any idea what I have to fucking do to get those tips!" Bobby cursed.
stripper getting face fucked

Lawrence did know because he'd also been working as a stripper right up until he started to show. The stolen memorabilia had ended up being extremely hard to move, and they'd had to settle for a tiny fraction of what Bobby expected. Fully expecting to go back to being a man, Bobby had been a bit careless in the robbery and was caught on video. That money had all gone to setting up their new lives as women in a new town.

"You'd probably get more in tips if you'd just let some guys fuck you." Lawrence shrugged. After he realized he was pregnant, he hadn't been shy about letting other guys fuck him.

"So I can end up preggers like you? No thanks." Bobby shook his head. "At least your baby is not going to just be some rando kid. He's gonna be a cash cow! Once he's out, we're totally going to sue Big D for paternity!"

Lawrence just rolled his eyes. Bobby was always a planner, even if none of those plans ever really turned out.