Gromet's PlazaTG/CD Stories

You Lost, Fair and Square

by Jackie Rabbit

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© Copyright 2022 - Jackie Rabbit - Used by permission

Storycodes: F/m; fpov; cd; reluct; X

This short story is much more about situation and subject, and less about plot, with this in mind I hope it still entertains. Getting to be the girl isn't ever losing though, at least from my biased opinion…

"…Why do I have to do it Jackie?" Roger whined.

"Because you won the poll we girls took, your height and size works for this too, and last but not least it was your girlfriend that bailed on us at the last minute." 

I was the official leader of the group - at least for the first phase - I had made the arrangements, had arranged for the small bus that would drop us off at the entry point, and I had the hiking charter to access the land we were to use in my name. Everything was arranged, but I should have known better than to include a boyfriend-girlfriend combo in the mix. Second year college students aren't known for stable relationships, so this one was on me, but at least all of us were friendly enough with each other.

The purpose was leadership training and exposure, not to necessarily teach leadership, but to reveal it. I had a working theory that leadership could perhaps be taught, but you had to start with something, and finding the people that had that "something" hidden in them was the trick. This was nothing new under the sun, even the Romans had their own programs a millennia ago that did much the same thing, although those had most certainly not been coed. I was leading for the start of this adventure, by design, as somebody had to get all the elements in one proverbial place, but I wondered if I would be at the end, one full week of isolation later. I suspected not, but that was the premise of the experiment after all.

"Doesn't this mean you'll be one man short then?" Roger persisted. He was right obviously, the group was chartered for six boys, men really, and six women, but finding another man that wanted to go coed camping wasn't all that hard. I already had a list of alternates to choose from in my head, where finding girls that didn't mind such things was the challenge. I had low expectations for Roger to emerge the alpha-male future-general officer here, but one never knows, and other that his whining - that I got the feeling was far more for my benefit that his - he was ordinarily a very likeable and easy to get along with guy. "Go along to get along" one could easily say, not exactly the working definition of leadership though.

Would the more alpha type guys have taken advantage of him on this trip anyway, and if so, what of his very pretty girlfriend Kennedy? I wondered. Her excuse was that this week was "her" week, and there was no way she was going on an extended backpack trip through the deep woods while trying to cope with that. I don't know if that was the truth, or if the couple had some kind of a spat instead, but when she broke the news to me I quipped that maybe her Roger should have to take her pink backpack in her place… to which she readily agreed for him, in theory. There was a list of what was supposed to be in it, and what wasn't, as well as the maximum weight; that as well was part of the experiment.

I had thought to perhaps spring this little twist up on Roger at the last second - with Kennedy's conspiratorial help - but that wouldn't have been fair to him, and I knew I had to feel him out first anyway. What if he had some kind of trauma in his early life or something, or some other kind of terrible life altering experience, and "making" him do this brought that up negatively? This was a human experiment in behaviour, but one had to remember that these were fellow humans first, and quasi lab rats second. This was the reason that to get along Roger and I were having breakfast together, and having our little talk privately.

"You signed up for this; told me you'd go," I reminded gently. Roger was a good guy, and while no alpha himself, he was dependable, and when he gave his word that meant something to him. He could bail on me too right now and I could still possibly make this experiment work anyway, but I also knew that I likely needed the dynamic that a young man like Roger would bring to the group, and he needed the extra credit participating would add to his grade. That was the other hook for my "volunteers;" they needed to be here, grade-wise. 

…I had thought it best to remind him of his commitment though, the honor of keeping your word, rather than using the negative motivation of his lacking academic achievements. One built him up; and the other reminded him of his failures…

"I did, but I thought that meant I'd be going as a guy, not in Kennedy's place, nor in her things."

I thought I had a pretty good ear for people, even at just barely twenty one myself, and unless I was mistaken Roger wasn't outright refusing to go along with my last minute outside the box gender switching plan, he was just reluctant. That likely meant that Kennedy had likely already planted the proverbial seeds; bless her devious heart. Going "as a guy?" That was a tell too, but in this context it possibly meant that pretending to be a guy was the act.

I grew up around very manly men, and a firm "no" from them was non-negotiable, it was in their very tone, in their DNA. That externally projected confidence and command left its mark on me early on, although how could anybody be so confident when all the facts simply weren't yet known? Those men in my life were right far more than they were wrong though, and this had caused me to wonder at how one gets intuition like that; and as a result here I am.

"But they would fit?" I clarified.

"They do fit, I know you talked with Kennedy, and I won't lie to you either."

"I know you won't, it's that kind of character that I need for this experiment to work. Patton was nothing without the men that followed him."

"'Lead, follow, or get out of the way,' I'm familiar with that quote from him, assuming we're talking about the famous WWII general."

"We are."

"I'm no great leader, you know that."

"I don't actually know that yet, but I do know that you have courage, and we've all signed the same NDA for this trip too, so what happens in the forest should stay in the forest. The only question is if you have enough courage to step out of your comfort zone here."

"Non disclosure agreement or not, my playing Kennedy on this trip will get out. I played a girl part in a high-school play once, the ribbing I got from that was pretty rough for a bit there."

"But you did it anyway?" This was news to me, and suggested that this wasn't very far from Roger's comfort zone at all.

"Yeah, for two reasons. One, this girl I was hot for was into theater, and two, the director told everybody that he forced me into it, after I read for the part to help out. I did this more as a joke, or at least that's what I told my friends. He didn't 'really' force me, and I didn't exactly read for that part as a joke either, I just wanted to see if I could do it, like it was my own personal challenge to myself."

"How did you do?" I asked, I was getting rather caught up into Roger's life, and here I thought he was more of a "set piece" as far as this little hiking trip was concerned.

"I did well in the play, but it was a supporting role, I wasn't the star or anything. As far as the girl, well… I'd rather not say, if that's okay with you."

"You know I'm curious now, I won't tell a soul, I promise."

Roger smiled, and I thought he was going to tell me he hit a backseat home run with her, that she was his first love or something…

"After our first dress rehearsal I was solidly in the friend-zone for life, the ‘girlfriend's zone’, amusingly enough. She actually wanted my dating advice on the track star jock of the school though, how should she approach him, what he might like to see her in, that kind of thing. He was actually a pretty good guy, and once I swallowed my pride and hooked him up with this girl, Lisa was her name. I had nothing to worry about from anybody in school, it was like having a big brother in school always watching out for me after that."

"That must have been really awkward for you. Do you ever talk with them?"

"Oh yeah, they're married, they even have a kid already, his dad owned a construction company or something, they're doing quite well. Some things are simply meant to be, and the Lisa thing was one of them. You have to understand, Lisa was just so far out of my league, she could have easily been a model, or an actress. And she was quite sweet too, a very good heart, we just didn't click with each other like that."

"And Kennedy?"

"She's out of my league too, but I make her laugh."

"And the costumes?" I prodded, trying to get the gender thing I was leading to back on track.

"Kennedy and I have a little game we play together, during hell week."

"'Hell week?'" I ask, as I'm not following him clearly, subject wise. What do hell week and costumes have to do with each other? I ask myself.

"Yeah, hell week, that's what I call it anyway. Three weeks out of every four Kennedy is the sweetest most wonderful girl on planet earth, but "that" week, look out. It's something genetic in her, the whole female side of her family is apparently like that, at least until they have kids! Her dad actually gave me a big hug when I first met him, he wished me luck. So anyway, I'm the official maid that week around the apartment, I wait on her hand and foot, full appeasement mode."

"That is so fricken’ sweet Roger, but to be just as honest, Kennedy didn't tell me specifically about that part, she just suggested that you might be up for what I had in mind, in very general terms. I was really asking about the play you were in, but I won't tell anybody about your sexy games with Kennedy either." 

"Of course. Well anyway, the girls all said I had nice legs, but I had to keep them shaved for the whole show. They gave me a crash course in walking and talking too, and I did both over the top flamboyantly, along with the mannerisms, almost as a joke. The joke was on me though, as after the first dress rehearsal the director told me not to change a thing. So while I did take some teasing early on, and I discovered that Lisa wasn't the least bit interested, I got a whole new bunch of people I could call my friends."

All the time Roger is telling me this, his right hand is flopping around and his head and neck are moving much like a woman's having an animated conversation with her girlfriend. His tone is even softer, more feminine, and except for the clothes that he's wearing, and his long unkempt hair, I swear that I could be having breakfast with a girlfriend. I don't know if he even realizes he's doing this though, or if just talking about this has brought back that other high school persona for him.

I have to also remind myself that he apparently gets to practice something like this every month, so it stands to reason that he's good at it. In my very limited world though, a guy dressing up as a girl means that he prefers guys, and experimenting with your sexuality while away at college isn't exactly unheard of either. That being said, I don't get the feeling that Roger is into other guys, but I find myself curious about this too. This is not to be judgemental, I just want to know for my own purposes.

"You do that very well" I told him, seeing if he understands where I'm leading this, seeing also how many hints Kennedy had given him as to what exactly I'm after.

"Thanks. Okay, if I tell you something else, can you promise me that it doesn't leave here?"


"My little female persona act makes Kennedy hysterical, so I bring out that female alter ego of mine all the time, when it's just her and I. Sometimes we'll even go a step further, and she'll dress me up in one of her old dresses and have me clean the apartment for her like this, during hell week. I cook, I clean, I give foot and back rubs too, I'm very servile when I'm in that persona, that mode."

"That's very hot and sexy, I wish I had a guy with that kind of humor."

"Not everybody would get it, and Kennedy doesn't exactly mind bossing me around either. She's awesome, don't get me wrong, but when she's having a bad week, her bad week, having me do menial stuff for her lightens the mood."

"So, you're willing to do this for me, maybe pretending to be Kennedy for our trip, in some form or another?"

"I don't think so, that act is for Kennedy only."

Roger had just told me that there were two reasons he played at being a girl; one was for a girl, and the second was because he was forced, although he really wasn't. The third reason he had alluded to was to see if he could actually do it; put on a convincing show in front of hundreds of paying audience members.

"You've done it on stage though?" I asked incredulously. Playing at being a girl for hundreds of people up on stage; pretending to be Kennedy for a dozen people in the woods. In my mind the one didn't equal the other.

"College is different," he told me. Even in this there was some wiggle room though, I sensed it.

Roger is just way more than I thought he was, I've allowed myself to underestimate him a second time, and I know that I have to stop doing this. Arguing the audience size of each is a logical argument though, and this is more a thing of passion. Roger had been passionately interested in his teen co-star in the play, Lisa, and that had in part led him to try something new. He was passionately committed to Kennedy, and that apparently led him to allow her to dress him up and use him like a tool.

I wasn't passionately interested in Roger, at least not at the moment with Kennedy in the picture, but I could still use him like a tool for my own purposes, giving him no choices, like his one time director allegedly did. Roger needed to be forced, it was simple, once I saw things clearly and thought about the situation critically for a few seconds.I just needed to ask somebody first…

"Can I make him do it?" I asked Kennedy in a quick text, right at the table as Roger watched me curiously.

"He responds best to harsh treatment and few options," she replied, like three seconds later. She was waiting for this from me, and I realize how much I'll miss her on this trip, that woman was a natural. I now have permission, but it's not lost on me as to who I had to get it from either. Kennedy owns Roger, but he's happily owned…

"NO SEX!" she adds, a few seconds later. I hadn't planned on that anyway, but with young people in the woods and away from society anything can happen. If that got out though, NDA and all, I'd be in serious trouble with the school though, so this wasn't my plan, although sexual inuendo and anything short of that was fair game.

"That wasn't my intention," I sent back, telling her that I was on the same page with her in regards to "her" Roger, but not going to the length to promise the actions of another either. One had to be careful with such things, it was one thing to promise you'd not do something, but a completely different one to promise another wouldn't.

"Here's the way of it Roger, I need you on this trip, and you've already given me your word. And, you're going to do this cheerfully, and you're going to be the very best woman you can hiking with us. Kennedy has already lent you to me and given her blessing on this, asking you was just an excuse so that we could get to know each other a little better over breakfast. Any questions at all?"

"No ma'am."

"Good, five properly dressed, at the cafeteria, it's going to be warm, so make sure you show some skin." 

"Yes ma'am, and thank you."

"Your welcome Roger, now that I have the measure of you I think we'll get along just fine. But, if we don't I'm sure Kennedy will tell me how she handles discipline in her home. One final thing, do you have a dressed up name that you use?"

"She calls me 'Buttercup' ma'am."

"See you tomorrow Buttercup…"


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