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Chandler’s got to have some kind of masochistic streak. On top of the already humiliating kink he has, that is.
It started that night with Susie. Chandler would be having a perfectly normal time right now, if not for that night. He still can’t believe she just ran off with his clothes. If he ever sees her face again, he’s going to do something awful. Not sure what yet, but it’ll be awful.
So, Susie. The night that she requested he wear her underwear, he may have discovered something unpleasant about himself. He told himself it was just because she was into it, and well, if a hot woman tells you to wear her panties, you wear her painties. Chandler wanted to get laid, okay? The awful thing is, that he didn’t entirely hate the experience. Not even after she left him in that stall. What a bitch, by the way. Seriously. Who does that?
Chandler sighs, looking down at himself. Specifically, he looks down to his hips. His hips that are currently wearing a pair of light blue lace panties and nothing else. The fabric is soft, comfortable. They’re only slightly more modest than the ones that he had on the night of the incident. There’s also a small black bow on the front. Very masculine. At the least the color choice is definitely better.
He’s not sure how his life came to this. He knows, ofcourse, but he just can’t believe it. Chandler Bing, standing alone in his bedroom, in lacy women’s underwear. If Joey walked in right now, he’d never hear the end of it. He hasn’t heard the end of it in general. That pink thong haunts him in the form of his roommate’s taunting.
Chandler pulls at one of the straps lightly with his forefinger. It’s stretchy, and snaps back satisfyingly when he lets go. He hadn’t actually planned what he’d do after he tried them on. He hasn’t even looked in the mirror yet. It’s as he’s turning around, that he spots the card that came with his… order.
He picks it up. Apparently, they included an extra item with his purchase. A gift for first time customers. Chandler doesn’t like that. “First time customer,” He scoffs, “Gee, I can’t wait to buy another pair of panties at a later date!” He ignores the slight twitch of his dick at that. He will not be making another purchase, dammit.
When he looks into the bag, sure enough, there’s another article of lingerie. He reaches in, slowly, and extracts it.
He probably shouldn’t be surprised. They had given him a matching bralette. Chandler would be incredibly surprised if it fit, given his general lack of breast tissue.
Only one way to find out.
Chandler takes the bra with him to his mirror, and then pauses. Is he really going to do this? It was one thing to buy the underwear, because he’d already worn them. He couldn't blame Susie if he put on the bra. His ego might not survive.
Oh, screw it. He gave up on having dignity or pride when he put on his current getup. He puts his arms through the bra, then slips it on over his head. It’s an embarrassing struggle for the first few seconds. When he’s managed to get it on his chest, he heaves a sigh of relief.
He looks at himself in the mirror. Inspects himself, if you will. The bralette is a bit loose in some parts, and a bit tight in others, but it fits better than Chandler expected. There’s a bow in between the uh, boob holding bits, that match the bottom. The panties fit weirdly on his dick, though it’s no worse than the thong was. He’d look better if he was shaved.
Still, he looks pretty decent. There’s gotta be dudes out there who look worse in women’s underwear. He’s not the intended model for these, yeah, but at least he isn’t Ross. Now that is an awful mental image.
Chandler hears the door unlock, and thinks ‘oh crap.’ before scrambling for his regular clothes.
“Chandler!” Joey’s voice rings through the door. Fuck, where did he put his pants? Where did he put his shirt?
He probably should have gone to lock his door first. Then he would have had all the time in the world. Unfortunately, Joey walks into his bedroom as Chandler is rummaging in his blanket for his clothing. He probably makes quite the odd sight, a man in lingerie just splayed across the bed.
“Cha…-?” He can see the exact moment Joey realizes what he’s seeing, because his voice drops off in the middle of saying his name.
“No way-!” Joey’s incredulous, just standing there with his jaw open, dumbfounded grin on his face. “Again?”
At this point, Chandler is aware there’s no point in continuing the search for his outerwear. He does however pull his blanket over himself. “Yep, you caught me! Now will you get the hell out of my room?”
“No way, man.” He repeats. “I can’t believe you’d put on women’s underwear again after the traumatic experience you had last time! And you even got a second piece!”
“Oh, right, that. I’d forgotten alll about it. Except that time I wasn’t wearing a bra, so really, it’s totally different.”
“So, who are you putting it on for this time?”
It occurs to him then, that Joey believes he’s been pressured into this by another woman. That’s a great excuse. Or at least it would be, but it’s on about second number 10 of Chandler trying to think of a plausible name that a look of sly understanding washes over Joey’s face.
“Ahh… I see. You just wanted to do this for yourself, huh?” Joey raises his eyebrows a couple times, and Chandler has to debate whether the prison sentence would be worth it to murder his roommate.
“Get out of my room.”
Because Joey occasionally has the sense for self preservation, he turns to leave, but not before leaving another comment. “You know, you could look worse.”
Chandler hurls a pillow at him, and Joey’s running out of the room like a cat faced with a spray bottle. God, that was humiliating.
It’s when he’s getting up to change that he notices his dick sticking out of his garment. He got hard while talking to Joey in lingerie.
Definitely gotta be some kind of masochist.
He stares at his dick. Sure, he could take a cold shower. But he’s already in the whole get up, and let’s be real, he didn’t exactly have pure intentions when he purchased it. It’s a little weird to jerk off now, after Joey’s discovered his little secret (on the first day of him having the secret, too. How is that fair?), but a man’s gotta do what a man’s gotta do.
The first slide of his hand over his cock is, quite frankly, delectable. You know, there’s something about wearing women’s underwear that really makes the whole experience more enjoyable. It’s probably a result of it feeling a little taboo. He rubs his thumb over the tip. Tightens his grip a little on the downstroke.
He wonders what he looks like right now. Chandler Bing, masturbating to himself in lacy blue lingerie. He just can’t stop thinking about how absurd it is. What would Joey say if he walked in again? Chandler grips himself with a little more force. Would he run out in fear? Would he say something about his eyes being tainted? Or would he close the door behind him? Would he take a step closer, acting fake surprised, as if Chandler had deliberately put on a show? Would he get nearer and nearer until his breath was ghosting across Chandler’s skin? Would he put his hands on Chandler’s waist and slide them up until he was cupping his chest through the lace of his bra?
It’s at that point in his fantasy that Chandler comes all over himself. He just did that. Chandler got off on the thought of his best friend and roommate walking in on him stroking his dick while wearing lingerie. What the fuck.
For a while, he stares up at the ceiling with a flushed face and then, to himself, says “I am so fucking screwed, aren’t I?”.