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Paying Up

Prompt originally from AetherRoom.club
Created: 2022-04-24
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Description
Sometimes, you make a bet that you would come to regret. This is one of those times. Your confidence in the local baseball team was immense, and you bet your doubting friend that if they wouldn't win the division, you'd crossdress and go to the mall with him as his girlfriend. Well, that has now come to pass, and you've got to pay up. Worst of all... you're kinda enjoying it.
Tags
yaoi, gay, first person, crossdressing, embarrassment
Prompt
"Oh, what the hell? There's no way that was a strike! We got robbed!" I yell impotently at the TV, unable to change the events that just occurred, namely that the local baseball team just lost another game and has officially been eliminated from contention for the division title. Logan, sitting next to me, has a smile on his face as he says, "Aw, well, looks like they won't win the pennant this season, eh?" Nodding my head, I let out a sigh and reply, "Yeah, I really thought they had a shot. Oh well, there's always next season. I swear, Rodriguez is going to have to break out sooner or later..." But then, after I change the channel, Logan shakes his head and asks, "Hey, Ash, aren't you forgetting something? Something rather important? From the beginning of the season?" As he gets up and heads to his room, I rack my brain for an answer to his question, but come up dry. What could he possibly be referring to? Wait, no, there was one thing, but there's no way he remembers that, right? I hardly even remembered that, so he can't be thinking of that... right? Because now that I think about it, I did make a rather unfortunate bet at the beginning of the season, when I was fully convinced the team would be the best it's ever been. And if he managed to remember that, well, that would be rather embarrassing. But all my hopes turn out to be dashed rather quickly, as when Logan returns, he's carrying a bag and waving around... a skirt. "I haven't forgotten, Ash! You were so confident this team would do well that you bet me they'd win the division, and if they didn't, you'd crossdress and play my girlfriend for the day!" he yells, the tone in his voice implying that he's kept this in mind this entire time and had in fact been excitedly preparing for the day I'd have to pay up. Damn it, he's absolutely got me now. I mean, I could deny it, but there's no way that'd fly with him, because he knows when I'm bullshitting him, and he'll see through me like a freshly washed window. From the way he's twirling that skirt around, he's downright ecstatic that he's got me. "Ahaha... you thought I, um, was serious? Th-That was, er, just a joke! Right? Totally hilarious joke, right?" I stammer nervously, trying to play it off, but just like I thought, he's not buying it in the slightest. "C'mon, Ash, you can't get out of this now. You were soooooo confident this was the year, why, you insisted that I should take that bet! And now, you're going to pay up," he says, sitting down on the couch and placing the bag down next to him. "I've got it all sorted out, and I've even got a wig for you. You're gonna wear all this, and we're gonna go to the mall! We're gonna be boyfriend and girlfriend for the afternoon, and it's gonna be great!" he exclaims, throwing the skirt into the bag as well and then setting it right on my lap with a self-satisfied grin on his face. Digging through the bag, he really has it all worked out. There's a skirt, a blouse, even a bra and panties, as well as a wig. God damn it, I'm not getting out of this. *** Well, here I am. Arm in arm, Logan and I step through the front doors of the mall, nothing unusual about that, no siree. And the fact that I'm dressed in women's clothing, including a skirt, a wig, and some rather tight panties, doesn't change that at all. "But what if someone recognizes me?" I ask him quietly, still nervous. Logan, meanwhile, looks like he doesn't have a care in the world. "Relax, Ash. This place is dead anyway, there's no way anybody that knows you is here. And besides, with that wig, nobody'll recognize you either," he says, clearly enjoying this way too much. He does have a point, though... this place pretty much embodies the death throes of rural Americana. There's maybe like ten other people walking around, and half the places here are closed or having some sort of clearance sale. And out of those few people shuffling about, most of them are old, retired people. Shuffling around a dying mall before they shuffle off this mortal coil. Maybe this won't be so bad... it is kind of exciting, after all. Somehow, going out in public dressed like a girl is actually thrilling to me. In fact, I'm pretty sure half the reason these panties I'm wearing are so tight is because I'm actually getting hard from the thrill of it all. God damn you, Logan, you knew this would happen, didn't you? We walk along the main path of the mall until we reach the main concourse and the big map, which Logan looks over with great glee. "Hmmm... where should I take my pretty little girlfriend? We could go to the ice cream parlor, watch a movie at the cinema, play some games at the arcade, maybe even go shopping for some new clothes for you! So many options. I think we'll start with... [Click to expand]
"Oh, what the hell? There's no way that was a strike! We got robbed!" I yell impotently at the TV, unable to change the events that just occurred, namely that the local baseball team just lost another game and has officially been eliminated from contention for the division title.
Logan, sitting next to me, has a smile on his face as he says, "Aw, well, looks like they won't win the pennant this season, eh?"
Nodding my head, I let out a sigh and reply, "Yeah, I really thought they had a shot. Oh well, there's always next season. I swear, Rodriguez is going to have to break out sooner or later..."
But then, after I change the channel, Logan shakes his head and asks, "Hey, Ash, aren't you forgetting something? Something rather important? From the beginning of the season?" As he gets up and heads to his room, I rack my brain for an answer to his question, but come up dry. What could he possibly be referring to? Wait, no, there was one thing, but there's no way he remembers that, right? I hardly even remembered that, so he can't be thinking of that... right? Because now that I think about it, I did make a rather unfortunate bet at the beginning of the season, when I was fully convinced the team would be the best it's ever been. And if he managed to remember that, well, that would be rather embarrassing. But all my hopes turn out to be dashed rather quickly, as when Logan returns, he's carrying a bag and waving around... a skirt. "I haven't forgotten, Ash! You were so confident this team would do well that you bet me they'd win the division, and if they didn't, you'd crossdress and play my girlfriend for the day!" he yells, the tone in his voice implying that he's kept this in mind this entire time and had in fact been excitedly preparing for the day I'd have to pay up.
Damn it, he's absolutely got me now. I mean, I could deny it, but there's no way that'd fly with him, because he knows when I'm bullshitting him, and he'll see through me like a freshly washed window. From the way he's twirling that skirt around, he's downright ecstatic that he's got me. "Ahaha... you thought I, um, was serious? Th-That was, er, just a joke! Right? Totally hilarious joke, right?" I stammer nervously, trying to play it off, but just like I thought, he's not buying it in the slightest.
"C'mon, Ash, you can't get out of this now. You were soooooo confident this was the year, why, you insisted that I should take that bet! And now, you're going to pay up," he says, sitting down on the couch and placing the bag down next to him. "I've got it all sorted out, and I've even got a wig for you. You're gonna wear all this, and we're gonna go to the mall! We're gonna be boyfriend and girlfriend for the afternoon, and it's gonna be great!" he exclaims, throwing the skirt into the bag as well and then setting it right on my lap with a self-satisfied grin on his face.
Digging through the bag, he really has it all worked out. There's a skirt, a blouse, even a bra and panties, as well as a wig. God damn it, I'm not getting out of this.
***
Well, here I am. Arm in arm, Logan and I step through the front doors of the mall, nothing unusual about that, no siree. And the fact that I'm dressed in women's clothing, including a skirt, a wig, and some rather tight panties, doesn't change that at all. "But what if someone recognizes me?" I ask him quietly, still nervous.
Logan, meanwhile, looks like he doesn't have a care in the world. "Relax, Ash. This place is dead anyway, there's no way anybody that knows you is here. And besides, with that wig, nobody'll recognize you either," he says, clearly enjoying this way too much. He does have a point, though... this place pretty much embodies the death throes of rural Americana. There's maybe like ten other people walking around, and half the places here are closed or having some sort of clearance sale. And out of those few people shuffling about, most of them are old, retired people. Shuffling around a dying mall before they shuffle off this mortal coil. Maybe this won't be so bad... it is kind of exciting, after all. Somehow, going out in public dressed like a girl is actually thrilling to me. In fact, I'm pretty sure half the reason these panties I'm wearing are so tight is because I'm actually getting hard from the thrill of it all. God damn you, Logan, you knew this would happen, didn't you?
We walk along the main path of the mall until we reach the main concourse and the big map, which Logan looks over with great glee. "Hmmm... where should I take my pretty little girlfriend? We could go to the ice cream parlor, watch a movie at the cinema, play some games at the arcade, maybe even go shopping for some new clothes for you! So many options. I think we'll start with
Author Notes
Thanks to a very bad decision when it comes to making bets, I am now crossdressing and acting as Logan's girlfriend while we hang out at the mall, intending to do all sorts of stereotypical date things like going to the ice cream parlor and watching a movie together. But while I had at times considered the thought of crossdressing appealing, I had no idea how it would feel to actually do it. And while it feels incredibly embarrassing and I can't stop myself from blushing... it's also exhilarating, and I can't stop myself from getting hard in my panties. And all the while, it seems like Logan knows exactly how I feel and wants me to get all flustered and turned on.
Memory
My name is Ash, and I'm a young male going to college. I've never been the most muscular type. In fact, I'm rather thin and scrawny, which has led to the occasional comment calling me girly. And while I've never admitted it to anybody, there's a part of me that genuinely wants to try being a bit more girly. It seems like a lot of fun, and so even while the thought is incredibly embarrassing, I kinda want to try crossdressing.
World Info
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  • Logan

    Logan is a young guy going to college and has been my friend for about two years now. Out of all the people that know me, Logan is probably the one that knows me best, and that includes my desires to try and be a bit more girly, maybe even trying crossdressing at some point. While he is very teasing about it, it seems like he's actually trying to help me broaden my horizons a bit and get out of my comfort zone. What helps is that I find him to be quite attractive and might even be falling for him, though I can't see myself admitting that without him coaxing it out of me.
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