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Paying Up (Reverse POV)

Prompt originally from AetherRoom.club
Created: 2022-05-03
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Description
I liked this scenario and decided to have a tiny hyperfixaction in which the point of view is reversed; you are now Logan.
Have fun!
P.S: I also set both Logan and Ash's attributes into cards to make it compatible with free AIDG users.
P.P.S: I know this doesn't really follow scenario conversion's rules, don't worry, I know what I am doing.
DISCLAIMER: I AM NOT THE ORIGINAL POSTER, OG SCENARIO IS HERE: https://prompts.aidg.club/3586
Tags
yaoi, scenario conversion, embarassment, crossdressing, first person, gay
Prompt
"Oh, what the hell? There's no way that was a strike! We got robbed!" Ash yells 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. I grin cheekily, saying, "Aw, well, looks like they won't win the pennant this season, eh?" Nodding his head, he lets out a sigh and replies, "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 he change the channel, I finally remember about that dare me and Ash set back, as I say, "Hey, Ash, aren't you forgetting something? Something rather important? From the beginning of the season?" I get up and head to my room, I see Ash lag behind. Did he seriously forget about that dare back then? Either way, I grab the bag I had and the skirt I bought just for this event. "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!" I yell, and it's obvious the tone in my voice implies that I had kept this in mind this entire time and had in fact been excitedly preparing for the day he'd have to pay up. I mean, who wouldn't? I mean, he could deny it, but I know when he's bullshitting me; I can see through him like a freshly washed window. "Ahaha... you thought I, um, was serious? Th-That was, er, just a joke! Right? Totally hilarious joke, right?" he stammers nervously, trying to play it off, but just as I said, it was futile. "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," I say, proping down on the couch and placing the bag down next to me. "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! Bahahaha, you're gonna be so embarassed!" I yell, throwing the skirt into the bag as well and then setting it right on his lap with a self-satisfied grin on my face. As I see him digging through the bag, it's obvious to him that I really have it all worked out. There's a skirt, a blouse, even a bra and panties, as well as a wig. I know for sure that he isn't getting out of this! *** Well, here I am. Arm in arm, Ash and I step through the front doors of the mall, nothing unusual about that, no siree. And the fact that he's dressed in women's clothing, including a skirt, a wig, and some rather tight-looking panties, doesn't change that at all. "But what if someone recognizes me?" he asks me quietly, still nervous. I, wholeheartedly, don'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," I say. I have a point; 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. I may be a psychopathic megalomaniac, but hey, I can see Ash blushing, and a bulge in his skirt. We walk along the main path of the mall until we reach the main concourse and the big map, which I look over with great glee, before speaking. "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!" Ash yells 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.
I grin cheekily, saying, "Aw, well, looks like they won't win the pennant this season, eh?"
Nodding his head, he lets out a sigh and replies, "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 he change the channel, I finally remember about that dare me and Ash set back, as I say, "Hey, Ash, aren't you forgetting something? Something rather important? From the beginning of the season?" I get up and head to my room, I see Ash lag behind. Did he seriously forget about that dare back then?
Either way, I grab the bag I had and the skirt I bought just for this event. "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!" I yell, and it's obvious the tone in my voice implies that I had kept this in mind this entire time and had in fact been excitedly preparing for the day he'd have to pay up. I mean, who wouldn't?
I mean, he could deny it, but I know when he's bullshitting me; I can see through him like a freshly washed window. "Ahaha... you thought I, um, was serious? Th-That was, er, just a joke! Right? Totally hilarious joke, right?" he stammers nervously, trying to play it off, but just as I said, it was futile.
"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," I say, proping down on the couch and placing the bag down next to me. "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! Bahahaha, you're gonna be so embarassed!" I yell, throwing the skirt into the bag as well and then setting it right on his lap with a self-satisfied grin on my face.
As I see him digging through the bag, it's obvious to him that I really have it all worked out. There's a skirt, a blouse, even a bra and panties, as well as a wig. I know for sure that he isn't getting out of this!
***
Well, here I am. Arm in arm, Ash and I step through the front doors of the mall, nothing unusual about that, no siree. And the fact that he's dressed in women's clothing, including a skirt, a wig, and some rather tight-looking panties, doesn't change that at all. "But what if someone recognizes me?" he asks me quietly, still nervous.
I, wholeheartedly, don'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," I say. I have a point; 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. I may be a psychopathic megalomaniac, but hey, I can see Ash blushing, and a bulge in his skirt.
We walk along the main path of the mall until we reach the main concourse and the big map, which I look over with great glee, before speaking. "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
World Info
View World Info
  • Logan

    My name is Logan, and I'm a young male going to college. I've never been the most muscular type, being very tall, but only with medium muscle mass, which has led to the occasional comment calling me a twig. And while I've never admitted it to anybody, there's a part of me that genuinely feels attracted to other guys. And this is only amplified by Ash's ostentatious curves, feminine wiles, and flamboyant attitude, which makes me want him really bad. Hey, at least I didn't lose the dare.
  • Ash

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