***
"Dude, you look ridiculous!"
"Well yeah, what did you expect? This," Justin motioned at his face, then the rest of himself, "doesn't exactly go with this."
'This' consisted of the garment on his body, the secondhand prom dress serving as quite the contrast to the face above, which hadn't seen a razor in a couple weeks. The chest and armpit hair that showed further highlighted the discrepancy, though Justin had to admit that Cory had done a remarkable job of finding a dress that fit him so well. Why he'd bothered baffled Justin; for one evening of humiliation, any feminine garb he'd have found would have sufficed so long as Justin could have squeezed himself into it. In any case, wearing the dress for an evening beat paying Craig the $200 he'd otherwise have to for losing that bet. He really had to stop getting so into sports.
"Yet."
"Yet?"
"A bet with $200 stakes and you think you're going to get away with just wearing a dress if you're electing not to pay cash? The dress didn't set me back that much. Karen's on her way to help with the rest."
"Your sister Karen...?" Justin trailed off, confused until he remembered that she worked as a cosmetologist. "Nuh-uh, no way."
"$200 sounds mighty good to me. I'll call her off if you just pay up now."
"Dream on. What's a little war paint?"
"Hey, it's your funeral. Don't let me stop you from becoming a pretty pretty princess."
"I think I'm fairly safe from that fate."
"I dunno, Karen does like herself a challenge, though it does look like you're trying to do the minimum to fulfill the bet."
"I'm wearing this silly dress, aren't I?"
"Yeah, but you're not wearing the stockings I also laid out, so it stands to reason you're not wearing the panties, either."
"Why do you care what I'm wearing under this?"
"You're the one that lost the bet. That means you follow my terms, or you pay up."
"You're not going to get all weird on me are you? This isn't some attempt to satisfy some twisted fetish of yours?"
"You got me. I've always longed for your sweet...man...bit..." Craig dissolved to laughter, unable to finish. "No, I just want to see you uncomfortable, just a bit of amusement."
"What if it's awakened something in me?" Justin wiggled his eyes and gave Craig a look of desire, licking his lips.
"Dude, not funny."
"Seemed pretty funny to me. But fine, I'll go put on the other items. Don't want you accusing me of not living up to the terms of the bet."
Justin left and headed back into Craig's guest room. He cast a dubious look at the opaque stockings and the silky pink panties, then shrugged. At least Craig hadn't procured a thong, as Justin imagined those would not provide much by means of comfort or containment. After he'd removed his usual underwear and picked up the silk panties, his mind drifted to when his ex had convinced him to wear a pair of hers. That had lasted only fleetingly, Debbie's arousal overriding any further explorations at the time.
As he prepared to step into the panties, his vision blurred and he felt dizzy, falling to the ground, surprised to feel it harder and colder than he'd have expected Craig's carpet to be. When his vision cleared, he realized that he'd somehow left Craig's apartment. Instead, he now lay in a kitchen all too familiar to him, the kitchen in Debbie's house, a good thirty minutes away at the least.
"Justin?" Debbie's voice filled the air, full of confusion and incredulity.
"Ah, hi?" he replied, turning his head towards her and hoping his voice sounded just as confused as hers.
"How'd you get here? And what are you wearing? Are those my panties?"
"No, they're uh--Craig's--or mine, for the evening, I guess. I lost a bet."
"So he sent you here to sneak in and humiliate yourself in front of me and my new boyfriend? Why are they in your hand? Are you naked under there? No, I don't want to know."
Always with the questions. Justin thought, remembering in full the grating tone her inquires and nagging questions could take.
"New boyfriend? Ah, shit." he looked the other direction, saw an average-enough looking guy standing in the entryway. "I don't even know how I got here."
"Well, green looks good on you." said Debbie's new beau, with a lame smile.
"Um, thanks?" He turned his attention back to his ex. "He seems nice, good for you."
"He is, not that your opinion matters. I think you should go. This is just weird."
"Quite."
"You're the one in drag, in your ex's house, interrupting a nice dinner with your sneaking in."
"Fully unintentional, I was just about to put on these panties, then I remembered that one night, and the next thing I knew, I was here."
"Well, maybe you should think about going downtown and hanging out with some of the other sleazy trannies instead of trying to win me back with the memory of one night of experimentation."
Her words summoned up the image of that shady area in his mind, and moments later he felt the same dizziness as before and his vision blurred once more. When it cleared, he found himself leaning against a wall along the very street he'd just thought of, the prostitutes already working all staring at his sudden appearance and assessing him.
"What the hell?" found himself saying in tandem with one of those also on the street.
"Not gonna get much action looking like that, hun. Plus, you generally want to keep your panties on, at least until you get a John." another said, upon approaching him.
"Thanks for the tip, not really planning on staying, though. Bye!"
Justin closed his eyes and imagined Craig's guest room once more, wishing to return there once more. He thought he might have felt a vague dizziness through his clenched eyes, and when he opened them, he sighed in relief at seeing the familiar walls of the room in which he'd started. What the heck had all that been? He stormed to the door to accuse Craig of--well, he didn't know what, exactly. Reconsidering, he figured he might at least put on the other items as Craig wouldn't drop the terms of the bet just because of strange events. Or a break with reality, which might make more sense given the impossibility of what had just happened. Regardless, he kept his mind clear as he slid on the panties and stockings, then stepped back into the main room of Craig's apartment.
"...went to the other room not two minutes ago. There's no way he drove twenty miles in two minutes, much less disappeared like Houdini when you were speaking to him." Craig shook his head and set down his phone, then looked over at Justin. "Dude, you ended things with your ex at the right time. She crazy, thinks you were just over there."
"I think maybe I was."
"Say again?"
"I was about to put on the panties, then remembered a night with Debbie, then next thing I knew, I was in her kitchen, interrupting a date with her new guy. You friends with a time-traveller or something who sold you a dress with teleportation powers?"
"Nope, unless my friend at the thrift shop isn't telling me something. So that actually happened, and you still put on the panties and stockings before rushing out here?"
"With my luck, you would have declared me in violation of the bet, then I'd be owing you $200."
"Yeah, true enough." His phone buzzed with a text message. "Karen's still about ten minutes away. Let's test your newfound power of teleportation in the interim. Go zap yourself to the gas station and grab us a couple beers."
"You want me to shoplift? I've always seen myself as more of a hero."
"Dude, get us free beer, you're a hero in my book."
"Fine. Just this once."
Justin envisioned the gas station in question, but nothing happened. No blurred vision, no dizziness. He closed his eyes and tried again. Craig still stood in front of him when he reopened his eyes.
"Well?"
"Nothing."
"I doubt both you and your ex shared a hallucination, so we're clearly missing something."
"I still think it's entirely possible I just went crazy."
"Also a possibility, yes. But let's try and rule out the impossible before we do something settle on something so mundane. You said that you'd been about to put on the panties when you found yourself at Debbie's, right? So you had not actually put them or the stockings on?"
"No, I hadn't, but why would this be limited to wearing the dress by itself?"
"Dude, it's teleportation. Who knows what sort of crazy restrictions it might have?"
"Fair enough."
Justin stripped off the stockings and panties, then tried thinking of the gas station once again. This time, the blurred vision returned and he found himself standing in front of the cooler holding the station's stock of beer. He opened it up and grabbed a couple, then willed himself back and tossed one of the beers to a shocked Craig. It hit his chest and fell to the floor.
"I'm not drinking that one, just so you know."
"That. Was. Awesome."
"Yeah. So what now?"
"Well, shit, you could do just about anything now, dude. Anywhere you've ever wanted to travel is a blink away! I might have to ask my friend to hook me up with one of those dresses that I can actually fit into!"
"Because I'm sure these are quite easy to find. People are always teleporting to their engagements. Go for it, at the very least we'll get a laugh of how silly you'd look."
"Nah, you're right. This is probably a one of a kind thing. At least we know you won't be able to teleport away in embarrassment tonight."
"Wait, what?"
"Bet's still on, man. We're heading out to Crossroads, why'd you think I was having Karen come over to doll you up?"
"Pictures for your amusement?"
"Nope, to see you squirm." Craig gave a wide smile.
"I hate you."
"Hey, I got you something you can use to travel wherever you want whenever you want. You're welcome."
"You're also making me go out in public dressed as a woman, to a bar where I'm likely to be hit on by guys. Not to mention that no gift I ever get you in the future would even compare to something that allows the wearer to teleport."
"Hey, girls go to that club, too, and I've seen more than a few leave with a crossdresser on their arm."
"I'm not really one by choice, though."
"Hey, if it results in you getting lucky, who are you to complain? Besides, if you ever want to teleport, that's going to require crossdressing just by the nature of the garment that allows it, so in those times it will be by choice."
"Well, technically, yes. Let's just get tonight over with."
"Hey, at least I'm not going to have you go to an adult video store like that."
Justin frowned at the thought of himself dressed like this in among the dirty DVDs and sexual objects, then found himself actually standing there. He quickly returned his thoughts to Craig's apartment and reappeared there, though not before someone had the chance to whistle at him.
"Dammit, Craig!"
He just laughed, and Justin joined in moments later. It had been pretty funny. Even so, to prevent any further unintentional departures, Justin put the panties and stockings back on. As he finished, Karen arrived, knocking on the door. Justin took a deep breath and steeled himself for the night to come.
He also suspected he'd need to meet with Karen after tonight, as well, if only to learn from her so as not to embarrass himself by not fitting in on his certain to come future excursions.
"Well yeah, what did you expect? This," Justin motioned at his face, then the rest of himself, "doesn't exactly go with this."
'This' consisted of the garment on his body, the secondhand prom dress serving as quite the contrast to the face above, which hadn't seen a razor in a couple weeks. The chest and armpit hair that showed further highlighted the discrepancy, though Justin had to admit that Cory had done a remarkable job of finding a dress that fit him so well. Why he'd bothered baffled Justin; for one evening of humiliation, any feminine garb he'd have found would have sufficed so long as Justin could have squeezed himself into it. In any case, wearing the dress for an evening beat paying Craig the $200 he'd otherwise have to for losing that bet. He really had to stop getting so into sports.
"Yet."
"Yet?"
"A bet with $200 stakes and you think you're going to get away with just wearing a dress if you're electing not to pay cash? The dress didn't set me back that much. Karen's on her way to help with the rest."
"Your sister Karen...?" Justin trailed off, confused until he remembered that she worked as a cosmetologist. "Nuh-uh, no way."
"$200 sounds mighty good to me. I'll call her off if you just pay up now."
"Dream on. What's a little war paint?"
"Hey, it's your funeral. Don't let me stop you from becoming a pretty pretty princess."
"I think I'm fairly safe from that fate."
"I dunno, Karen does like herself a challenge, though it does look like you're trying to do the minimum to fulfill the bet."
"I'm wearing this silly dress, aren't I?"
"Yeah, but you're not wearing the stockings I also laid out, so it stands to reason you're not wearing the panties, either."
"Why do you care what I'm wearing under this?"
"You're the one that lost the bet. That means you follow my terms, or you pay up."
"You're not going to get all weird on me are you? This isn't some attempt to satisfy some twisted fetish of yours?"
"You got me. I've always longed for your sweet...man...bit..." Craig dissolved to laughter, unable to finish. "No, I just want to see you uncomfortable, just a bit of amusement."
"What if it's awakened something in me?" Justin wiggled his eyes and gave Craig a look of desire, licking his lips.
"Dude, not funny."
"Seemed pretty funny to me. But fine, I'll go put on the other items. Don't want you accusing me of not living up to the terms of the bet."
Justin left and headed back into Craig's guest room. He cast a dubious look at the opaque stockings and the silky pink panties, then shrugged. At least Craig hadn't procured a thong, as Justin imagined those would not provide much by means of comfort or containment. After he'd removed his usual underwear and picked up the silk panties, his mind drifted to when his ex had convinced him to wear a pair of hers. That had lasted only fleetingly, Debbie's arousal overriding any further explorations at the time.
As he prepared to step into the panties, his vision blurred and he felt dizzy, falling to the ground, surprised to feel it harder and colder than he'd have expected Craig's carpet to be. When his vision cleared, he realized that he'd somehow left Craig's apartment. Instead, he now lay in a kitchen all too familiar to him, the kitchen in Debbie's house, a good thirty minutes away at the least.
"Justin?" Debbie's voice filled the air, full of confusion and incredulity.
"Ah, hi?" he replied, turning his head towards her and hoping his voice sounded just as confused as hers.
"How'd you get here? And what are you wearing? Are those my panties?"
"No, they're uh--Craig's--or mine, for the evening, I guess. I lost a bet."
"So he sent you here to sneak in and humiliate yourself in front of me and my new boyfriend? Why are they in your hand? Are you naked under there? No, I don't want to know."
Always with the questions. Justin thought, remembering in full the grating tone her inquires and nagging questions could take.
"New boyfriend? Ah, shit." he looked the other direction, saw an average-enough looking guy standing in the entryway. "I don't even know how I got here."
"Well, green looks good on you." said Debbie's new beau, with a lame smile.
"Um, thanks?" He turned his attention back to his ex. "He seems nice, good for you."
"He is, not that your opinion matters. I think you should go. This is just weird."
"Quite."
"You're the one in drag, in your ex's house, interrupting a nice dinner with your sneaking in."
"Fully unintentional, I was just about to put on these panties, then I remembered that one night, and the next thing I knew, I was here."
"Well, maybe you should think about going downtown and hanging out with some of the other sleazy trannies instead of trying to win me back with the memory of one night of experimentation."
Her words summoned up the image of that shady area in his mind, and moments later he felt the same dizziness as before and his vision blurred once more. When it cleared, he found himself leaning against a wall along the very street he'd just thought of, the prostitutes already working all staring at his sudden appearance and assessing him.
"What the hell?" found himself saying in tandem with one of those also on the street.
"Not gonna get much action looking like that, hun. Plus, you generally want to keep your panties on, at least until you get a John." another said, upon approaching him.
"Thanks for the tip, not really planning on staying, though. Bye!"
Justin closed his eyes and imagined Craig's guest room once more, wishing to return there once more. He thought he might have felt a vague dizziness through his clenched eyes, and when he opened them, he sighed in relief at seeing the familiar walls of the room in which he'd started. What the heck had all that been? He stormed to the door to accuse Craig of--well, he didn't know what, exactly. Reconsidering, he figured he might at least put on the other items as Craig wouldn't drop the terms of the bet just because of strange events. Or a break with reality, which might make more sense given the impossibility of what had just happened. Regardless, he kept his mind clear as he slid on the panties and stockings, then stepped back into the main room of Craig's apartment.
"...went to the other room not two minutes ago. There's no way he drove twenty miles in two minutes, much less disappeared like Houdini when you were speaking to him." Craig shook his head and set down his phone, then looked over at Justin. "Dude, you ended things with your ex at the right time. She crazy, thinks you were just over there."
"I think maybe I was."
"Say again?"
"I was about to put on the panties, then remembered a night with Debbie, then next thing I knew, I was in her kitchen, interrupting a date with her new guy. You friends with a time-traveller or something who sold you a dress with teleportation powers?"
"Nope, unless my friend at the thrift shop isn't telling me something. So that actually happened, and you still put on the panties and stockings before rushing out here?"
"With my luck, you would have declared me in violation of the bet, then I'd be owing you $200."
"Yeah, true enough." His phone buzzed with a text message. "Karen's still about ten minutes away. Let's test your newfound power of teleportation in the interim. Go zap yourself to the gas station and grab us a couple beers."
"You want me to shoplift? I've always seen myself as more of a hero."
"Dude, get us free beer, you're a hero in my book."
"Fine. Just this once."
Justin envisioned the gas station in question, but nothing happened. No blurred vision, no dizziness. He closed his eyes and tried again. Craig still stood in front of him when he reopened his eyes.
"Well?"
"Nothing."
"I doubt both you and your ex shared a hallucination, so we're clearly missing something."
"I still think it's entirely possible I just went crazy."
"Also a possibility, yes. But let's try and rule out the impossible before we do something settle on something so mundane. You said that you'd been about to put on the panties when you found yourself at Debbie's, right? So you had not actually put them or the stockings on?"
"No, I hadn't, but why would this be limited to wearing the dress by itself?"
"Dude, it's teleportation. Who knows what sort of crazy restrictions it might have?"
"Fair enough."
Justin stripped off the stockings and panties, then tried thinking of the gas station once again. This time, the blurred vision returned and he found himself standing in front of the cooler holding the station's stock of beer. He opened it up and grabbed a couple, then willed himself back and tossed one of the beers to a shocked Craig. It hit his chest and fell to the floor.
"I'm not drinking that one, just so you know."
"That. Was. Awesome."
"Yeah. So what now?"
"Well, shit, you could do just about anything now, dude. Anywhere you've ever wanted to travel is a blink away! I might have to ask my friend to hook me up with one of those dresses that I can actually fit into!"
"Because I'm sure these are quite easy to find. People are always teleporting to their engagements. Go for it, at the very least we'll get a laugh of how silly you'd look."
"Nah, you're right. This is probably a one of a kind thing. At least we know you won't be able to teleport away in embarrassment tonight."
"Wait, what?"
"Bet's still on, man. We're heading out to Crossroads, why'd you think I was having Karen come over to doll you up?"
"Pictures for your amusement?"
"Nope, to see you squirm." Craig gave a wide smile.
"I hate you."
"Hey, I got you something you can use to travel wherever you want whenever you want. You're welcome."
"You're also making me go out in public dressed as a woman, to a bar where I'm likely to be hit on by guys. Not to mention that no gift I ever get you in the future would even compare to something that allows the wearer to teleport."
"Hey, girls go to that club, too, and I've seen more than a few leave with a crossdresser on their arm."
"I'm not really one by choice, though."
"Hey, if it results in you getting lucky, who are you to complain? Besides, if you ever want to teleport, that's going to require crossdressing just by the nature of the garment that allows it, so in those times it will be by choice."
"Well, technically, yes. Let's just get tonight over with."
"Hey, at least I'm not going to have you go to an adult video store like that."
Justin frowned at the thought of himself dressed like this in among the dirty DVDs and sexual objects, then found himself actually standing there. He quickly returned his thoughts to Craig's apartment and reappeared there, though not before someone had the chance to whistle at him.
"Dammit, Craig!"
He just laughed, and Justin joined in moments later. It had been pretty funny. Even so, to prevent any further unintentional departures, Justin put the panties and stockings back on. As he finished, Karen arrived, knocking on the door. Justin took a deep breath and steeled himself for the night to come.
He also suspected he'd need to meet with Karen after tonight, as well, if only to learn from her so as not to embarrass himself by not fitting in on his certain to come future excursions.
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