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Sissy

My roommate signed for my panties and I had to put them on

Sissy roommate ordered panties and a plug. Straight roommate signed for it by mistake, opened the box, made him wear them and fucked him on the couch.

He opened the pink thong like a letterMy roommate made me walk to him in them

18+ Adult fiction. Everyone in it is an adult.

adult sexual contentanal sexcrossdressinghumiliation-kink
humiliationanalcrossdressingplugged
sissy

the app notification says 6:47am. delivery confirmed—signature required—delivered by jacob j. which is my roommate’s first and middle name so that’s how i know exactly how badly i fucked up.

i work overnight at the sheet & shell on route 19. ten p.m. to seven a.m. sundays through thursdays. that’s the shift that pays extra and lets me order things to my apartment without anyone asking why i’m getting fedex boxes in the middle of the day. it’s a solid plan except when jacob decides to sign for my fucking package.

jacob is a plumber’s apprentice. he’s loud as hell, eats cereal at three in the afternoon like it’s a meal and not a snack, never remembers that he lives with another person. his shower schedule is a mystery. his music taste is inexplicable—like fifty-fifty between death metal and country. he leaves his work boots by the door and the laces are always untied. we’ve lived together for eight months and i think he’s asked me maybe four questions about myself, none of which went beyond “you want pizza?”

so when i came home at 7:12am that morning—stopped for coffee, my hands were already shaking—i found him on the couch holding a pink thong like he’d found a murder weapon.


the box was next to him, open. the amazon smile looking up at both of us like it was laughing.

“this has your name on it,” he said. not a question.

i couldn’t think of anything to say that wouldn’t make it worse so i didn’t say anything.

“open it in front of me.”

“jacob—”

“open it.”

he was still holding the thong. silk, size small, hot pink with a black lace trim. it was a nice one too. i’d spent extra on the rating algorithm to find one that would actually fit. underneath it in the box was the plug—rose gold, about 2.5 inches, a weight to it. i’d been saving for three weeks for that specific one because reviews said it had a nice curve. there was also a bottle of hybrid lube because i’m not an idiot.

“you gonna stand there or you gonna open it,” jacob said.

my hand was on the edge of the couch. i opened the box. pulled out the thong first, just the thong, held it.

“oh fuck,” jacob said. “no. you’re not—”

“i can explain—”

“is this what you—are you a—” he stopped. just sat there with the pink fabric hanging between us. then he put the other thong down and lit up a cigarette like his life depended on it. there was no ashtray so he just let the ash fall on his jeans.

this was the moment where it could have gone really bad. where he laughs or gets mean or decides he can’t live with me anymore. i’ve run this scenario in my head a hundred times and every version ends with him asking me to move out.

but jacob’s not complicated. jacob’s simple in a way that sometimes works out for the weird people.

“put it on then,” he said.

i thought i heard him wrong.

“what?”

“put it on. put the whole thing on. i wanna see.”

“are you serious right now—”

“you heard me. go put it on. come back out here.”

my legs felt like they weren’t mine. i went to my room and locked the door even though there was no point. took off my sheet & shell polo shirt and my black work pants and my already sweaty boxers. my hands were shaking so bad i couldn’t get the thong on the first try. second try i got my left foot in, then my right. pulled it up. it fit perfect. the back of the plug against my hole and i felt my cock try to get hard and failed because i was too fucking terrified.

i came back out into the living room where jacob was now halfway through his cigarette.

“walk,” he said.

“what?”

“walk across the room. i wanna see it.”

this is the thing about humiliation kink that nobody tells you—nobody, like this information is classified—is that it doesn’t feel bad. it feels like the walls are coming down. like your whole body is just. exposed. and you’re waiting for the impact of being that exposed and it doesn’t come, it just comes and it comes and there’s no fight. you just walk across the living room in a pink thong in front of your straight roommate at seven in the morning and your body goes somewhere that feels like falling.

i walked.

the carpet was rough under my bare feet. my cock was hanging out the sides because silk doesn’t compress anything. jacob watched the whole thing like he was watching a video he couldn’t quite believe was real.

“come here,” he said when i got to the other side.

i came back.

he reached down and undid his jeans and his cock came out—he sleeps in sweats, goes to bed in sweats, apparently just whips it out on the couch without ceremony. he was hard. thick, cut, the kind of cock that looks utilitarian, like it was designed for one job and one job only.

“you want this?” he said.

“i—”

“yes or no.”

“yes,” i said.

“good. get the lube.”

i got the hybrid bottle from the box. came back. he took it and squeezed it on his hand and stroked himself once, twice, getting it slick, and then he pulled the thong down just enough to expose my hole. two fingers went in without warning and i gasped. his fingers were thick and they found the plug and pushed against it like he was testing if i was already stretched.

“you put this in this morning?” he said.

“no. not yet.”

“gonna feel even better then.”

he pulled the plug out slowly. i felt it drag and it burned a little and then it was out and the air hit me and i was so empty it almost hurt. he set the plug on the armrest and looked at my hole like he was trying to solve a math problem.

“don’t move,” he said. and then he bent down and licked.

i made a noise. it wasn’t quiet.

his tongue was warm and he knew what he was doing, that was the thing that fucked me up. he licked slow, deliberate, tongue stiff and pushing at my opening, and he kept going until i was shaking and then he pulled back and jerked himself a couple of times and pushed inside.

the stretch was real. he was bigger than the plug and he was going fast and i grabbed the back of the couch to ground myself.

“this what you wanted?” he said. “this why you order the panties?”

“yes,” i said.

“you like me fucking you while you’re dressed like this?”

i couldn’t answer. he grabbed my hip and made me take more of him and that was answer enough.

there wasn’t much prep. he pushed all the way in and stayed there and my body had to just… fit him. had to figure it out. the thong was still on, just pushed aside, the elastic rubbing against his thigh. he was using me like i was a toy and i was okay with that, i was more than okay with it, my cock was leaking without even being touched.

“you’re shaking,” he said. it was an observation.

“are you—is this—” i couldn’t form the sentence. he seemed to understand anyway.

“you good?” he said. actual check-in. actual consideration underneath the roughness.

“yeah. yeah i’m—keep going. please.”

he kept going. picked up the rhythm. one hand on my hip, one hand on the armrest, and he was just taking what he wanted and i was just giving it and it felt like falling and flying at the same time. his breathing got uneven. he grabbed the back of the thong and pulled, using it as leverage, and the elastic bit into my hip and it shouldn’t have felt good but it did.

“come on,” he said. “come for me.”

i came without him touching my cock. just came from him inside me, from being this exposed and wanted even in this weird weird situation. felt it happen from somewhere deep and then he groaned and pushed all the way in and came too, his hips pressing against my ass, his fingers tight enough to bruise.

he didn’t pull out right away. just sat there breathing against my back. then he pulled out slow and grabbed a throw pillow to sit on and tucked himself back in his sweats like we hadn’t just. like that wasn’t just real.

“that plug back in,” he said.

i got it. cleaned it. slicked it with the lube. pushed it back in while he watched. it went in easy now, my body already open from him, and it settled in deep.

“wear that all day,” he said. “the panties and the plug.”

“at work?”

“all day.”

he turned on the tv to sportscenter and lit another cigarette. i sat down on the other end of the couch in my pink thong and my empty brain and my very full ass and my phone buzzed.

the deliversmart app. the notification i’d been dreading all morning.


jacob j. — how was your delivery experience?

⭐⭐⭐⭐⭐ rate your delivery

i looked at jacob. he was watching sportscenter like nothing happened. eating cereal at 7am on a thursday which is somehow worse than 3pm.

i clicked five stars.

the next notification came through before i could close the app.


thank you for your feedback! jacob j. will be notified of your satisfaction!

and then, before i could even think, jacob’s phone buzzed on the coffee table. he picked it up. looked at it. a smile i’d never seen before spread across his face.

“you,” he said. “are fucking unhinged.”

“i’m not—”

“yeah you are. i like it. don’t take the panties off till i say.”

he went back to sportscenter. his cereal got soggy. outside the window the sun came up over route 19 and the sheet & shell sign flashed its discount prices and my coworkers were clocking out and i was sitting on my roommate’s couch full of plug and humiliation and this weird feeling that maybe i’d found my person.

the amazon smile had fallen on the floor. i picked it up and tossed it in the recycling.

jacob was already texting someone about my five-star rating. he was laughing.

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