Both Providing
Amy and Cassidy were just arriving on a tropical island. For a vacation yes, but it was a work outing, so attendance was "heavily suggested." Not that they were complaining, getting to come here for Cassidy's work was great! It just came with a pretty large caveat. Amy had been doing Cassidy's work for him for... almost the entire time he had been at his job, so while it was "his job" Amy was the only one who knew what was going on. That's why they came together, but Amy had something else in mind to make the experience a little bit easier on the both of them.
"It's so... strange. It's like I can feel everyone's eyes on me." The two of them weaved in and out of crowds of tourists and their own co-workers to get to their hotel room. Cassidy and Amy had swapped bodies, so while Amy was dressed in a suit and tie, ready for a meeting coming up shortly, Cassidy was right at home at this tropical resort dressed in a sexy two piece. Everyone's eyes were on Cassidy, was Amy always looked at like this too? It was... a strange feeling.
"Haha! Yeah, you might have to get used to that." The two of them made their way inside their room and got away from prying eyes. Amy got her stuff together while Cassidy looked at himself in the mirror.
"Wow, you really are sexy..." Cassidy posed and then jumped when Amy laid one hand on his ass, and the other on one of his breasts.
"Don't I know it! Now you know what it's like." Amy laughed and let her boyfriend turned girlfriend go. Cassidy blushed and looked away, some small part of him disappointed that they didn't go any further than that, but the other part of him to scared to take that step so quickly, even if they had been sexually active for quite some time.
"Why do I have to be in your body, isn't this a bit far?" Cassidy shifted uncomfortably in his two piece while he remembered the looks he received from strangers and colleagues alike when he was outside.
"I was more of a man in the relationship anyways if you think about it. It'll be fun! I can be the breadwinner both in action and in person for a week, and you can... be super hot!" Well... she had a point, to some degree. Being a man was... fitting for her, to some degree. "In any case, I'll be back in just a little bit, gotta get some paperwork done and attend that meeting. Don't have fun without me, okay?" And just like that, Cassidy was left to wind down and think about the situation he found himself in.
---
Cassidy sat in silence as he thought about what they were going to do while they were here. He was going to be the woman in the relationship the whole time so... were they going to... do it like this? As he thought harder and harder about he couldn't believe the feelings that rose inside of him as he thought about his own dick. It wasn't like they hadn't had sex before, but getting turned on by his own body? He looked in the mirror and got a good look at his new pussy. He had seen it plenty before but from this perspective... they probably were going to fuck like this huh? The thought of Amy taking control and pulling his hair as they messed up the pristine resort bed... he reached down between his legs and began to rub when...
"What did I say about having fun without me?" Cassidy jumped and slipped his bikini bottom back on as Amy got back. She cracked a smile looking at the condition Cassidy was in, clearly about to familiarize himself with his new body.
"Uh, well, I, uh..." Cassidy looked up as he noticed the tent that Amy was pitching. Had he always been so large? It looked like a whole different beast from below and when her pants were off...
"Well I didn't say to stop!" Cassidy blew a fuse thinking about what sex was going to be like while Amy quickly ripped off everything she was wearing, revealing that Cassidy's own dick was pulsing, ready to go. "Let's get started, why don't we?"
---
In the few days that Cassidy and Amy had spent fucking like rabbits between work calls and beach visits, he had formed a completely new mentality around the whole experience. Being a woman was great! Amy provided for him, and he got to "provide" for her as well, it was the best! Being the one getting roughed up in bed, taking salty loads to the face, Cassidy couldn't get enough of it, he was an absolute cumslut. Not only that, he had become a hell of an attention whore too. The looks that made him uncomfortable yet horny before became his favorite thing in the world. The envy other people had for him and Amy, the thoughts that probably ran through those men's heads... it was intoxicating.
"So, I was thinking..." The two of them were making their preparations for going back home when Cassidy began to suggest something that had been on his mind for the past few days.
"That we stay like this? Forever?" Amy excitedly snapped back, clearly waiting for this moment to come.
"Wha- well, yeah, what do you think?" How did she- well, it wasn't so surprising, the two of them had never been happier. Cassidy shifted uncomfortably, realizing how selfish it was for him to ask this of her but... being a woman was perfect for him, he loved everything about it. And Amy seemed to love the power she now had over him in bed so...
"I think you already know what I think" Amy unzipped her pants revealing that she was in need of some love. Of course, Cassidy excitedly got down on his knees, more than happy to provide it.
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