Incomplete - C(r)ossplay Photoshoot - WIP Crossdressing Story

(All characters in the story are 18+)

Benjamin sat behind his computer when he suddenly got a notification on his phone. It was a message from his (kinda) close friend Melissa.

‘’Hey Ben! Could you maybe help me? You’d do me a huuuge favor!’’

‘’What’s up?’’

‘’I was supposed to do a photoshoot today for a new cosplay I’ve made, but the person that was meant to help got sick.’’

‘’Oh you need a camera man? Think I could make some pretty alright pics.’’

‘’Haha, not exactly…’’

‘’Oh no…’’

‘’I need a model.’’

‘’Y-You only make female cosplays… don’t you?’’

‘’Yes, but, well, you see… I made the cosplay to fit the person that was supposed to help me and you’re the only person I know that comes close enough to fitting the outfit.’’

‘’…’’

‘’Pleaaaaaaase! I need to have these pictures before tomorrow!’’

‘’Why?’’

‘’It’s for one of my art classes!’’

‘’…’’

‘’Please! I promise I’ll do something in the future for you in the future as well!’’

‘’…Don’t tell a soul that I’m the guy in the girls costume, alright?’’

‘’OMG does this mean you’ll do it?’’

‘’Didn’t answer my question.’’

‘’Ofc I won’t tell them that it’s you! I’ll just say it’s the girl I originally asked, she isn’t in my class, so there shouldn’t be anyone to proof otherwise! Plus no one knows you in my class anyway! We go to different colleges also!’’

‘’Fair… alright, I guess I’ll help you. When do you need me?’’

‘’Now.’’

‘’Oh, alright, just give me like 30 minutes and I’ll be there.’’

‘’Thank you!!!!!’’

Benjamin sighed as he turned his phone screen off and leaned back in his chair.

‘’FINALLY!’’ he suddenly yelled. ‘’Man, I was starting to think she’d never put me in one of her cosplays!’’

Benjamin had a secret crossdressing kink.

He showered, putting it colder than normal to make sure he wasn’t dreaming. He tried to pull the big smirk of his face in fear of Melissa figuring out he actually doesn’t dislike the idea of crossdresser. Melissa lived within walking distance to Benjamin, around 25 minutes, however Benjamin being fueled by lustful excitement made the walk in just 10 minutes.

He took one final breath, trying to think of stuff that made him sad, like homework and politics, to come over as his usual, totally not into crossplay, self and then pushed the doorbell.

‘’Brrrrrzzzzttt’’ the bell rang announcing Benjamins presence.

‘’Huh? Already? … I’m coming!’’ Melissa said from inside as her footsteps drew nearer.

The door unlocked and their eyes soon met.

‘’Heeey Ben! Man, you did those 30 minutes real quick!’’

‘’Huh? Oh, yeah, thought I needed to finish something, but turned out I already uh finished it.’’

‘’Well, the more time we have the better! Getting you into the right shape might take a bit, hehe.’’ Melissa said with perhaps too much enthusiasm.

‘’…The right shape…?’’

‘’Uhuh, I mean, for one you’re flat as a board and you’re booty isn’t much better~’’

‘’W-wha?’’ Ben turned a bit red after this sudden… insult? ‘’The flat board thing is just true, but don’t go dissing my buns!’’ Ben tried to say in equal playfulness, but his embarrassment was clear to Melissa.

‘’Yeah, yeah, well get those buns into the room to the right, I’ve got everything set up there.’’

‘’Yes, Ma’am.’’ Ben replied as he entered her home, eyes moving to the right, wanting to get a peak at what Melissa had prepared as soon as possible.

To his disappointment a table was covered by a big white cloth, most likely keeping all the make up and cosplay hidden for just a bit longer. He tried to not show this disspapintment too much as he turned to sit on the chair next to the table.

‘’Oh Ben, one thing before you go sit in that chair…’’

‘’Huh?’’

‘’Strip’’

‘’W-what?’’

‘’Strip, undress, take off those clothes that aren’t my cosplay!’’

‘’… hehe… uhm… like… uhm…’’

‘’How else am I supposed to dress you?’’

‘’Y-yeah but… what about the uh… ya know…’’ Benjamin pointed downwards.

‘’Hmmm? Oh that’s what I got these for!’’ Melissa said joyfully as she pulled a black thong from under the white cloak on the table.

Ben turned red again and put his hand over his nose and hand, lowering the hand as soon as he remembered people only get nosebleeds when turned on in anime.

‘’Hahaha! Sorry Ben, I’ll tell you what the plan actually is now. Just strip down to your boxers, please. I first have to put some shapewear on you.’’

‘’Ah..haha.. right so I don’t have to wear that thong…g-good.’’

‘’Hmmm? Well you are still gonna wear them, but you’ll be wearing some shapewear under it, so you don’t need to worry about your manhood peeking out, haha.’’

‘’Ehehehe, yeah… So, uh, shapewear, you said that a few times but uhm, what is it?’’

‘’Oh just like some pants to smooth out your, ya know, lower bits, the bulge, make that all nice and not noticeable but also to add some volume to your hips and butt with some padding.’’ Melissa said as she grabbed a greyish colored pair of shorts made from a tight material with extra filling on the hips and butt area.

‘’Ah… that’s uh… Thicc.’’

‘’Yup! You’re gonna be quite curvy after this.’’ She said cheekily.

(Oh hell yeah, that’s so hot.) Ben thought to himself, again trying to hide his excitement.

‘’Soooo, I’ll leave you with that padded short for a few minutes and just give me a shout when you’re done.’’

‘’Alright, yeah, sure thing.’’

Melissa went to the room next over leaving Benjamin alone with his thoughts for bit.

He sighed again as he started by taking of his shoes and socks, moving to the shirt and eventually, his pants. He placed it all neatly next to the couch. His gaze then turned to look at the padding filled briefs, slowly reaching out to it with his hands. The tight material hugged his legs strongly as he struggled slightly with getting it on right, but the moment his hips and butt were in contact with the padding. He felt an immediate sensation of comfort come over him as he slapped new padded thick booty.

(Oooooh yeaaaaaah, I love this thicc ass!)

‘’Great, looks like you got it on perfectly on your own! Now your tummy and bulge are all nice and flat and the important parts nice and big!’’

‘’Huh?!’’ Ben turned as he suddenly heard Melissa unannounced. ‘’Uh, y-yeah..’’

‘’Now to make fix that chest of yours…’’

‘’Eh?’’

Melissa turned to revealed a grey vest with huge breasts attached!

‘’W-wow is that a… breastplate?’’

‘’Hmmm? Yes, actually, how did you know that?’’

‘’Huh? Oh no, I meant it like as uh… the armor, you know, a breastplate, but this one has uh, actual breasts. I was just making a pun! … S-so it’s actually called that? Haha, n-nice!’’

‘’Haha, yeah, alright, I’ll help you into this vest, basically it is head first and then you can slide your arms into the arm holes.’’

‘’Simple enough… I’ll follow your lead I guess, haha.’’

Melissa pulled the throat of the vest wide open so Ben could easily slide his head through, after some wriggling around he also successfully got his arms through the sides. Once the breasts were equipped Benjamin couldn’t help but stare at them.

‘’You want to grab them, don’t you?’’

‘’H-Huh? W-what? Haha… uhm… well… I mean…’’

‘’Go ahead, I don’t judge, probably the only time you’ll get to touch J cups!’’

‘’Holy hell, these are J cups?! I thought they were big, but, damn.’’

‘’Yeah, I thought it would be fun to make some clothes from a more ‘’uncommon’’ size. Hope it will give me some bonus point for the class, for the effort or something.’’

‘’You are definitely getting some bonus points from me, haha.’’ Ben said as he casually started to fondle the big silicon filled flesh mounts now attached to his body.

‘’I was planning to now shave you… but it seems you are already as smooth as can be!’’

Benjamin panicked a bit, as he had indeed shaved his body to look a bit more feminine even if not actively crossdressing.

‘’Oh yeah, I just do that for the heat, it’s pretty much summer, all that hair, just makes me all sticky and such, you know…’’

‘’Regardless, I’m not complaining. Guess we’ll just move over to the body painting!’’

‘’I’m sorry the what now?’’

‘’You noticed that padding and breastplate being grey I bet.’’

‘’Y-Yeah?’’

‘’Well, are breasts normally grey?’’

‘’No… they match the skin tone…?’’

‘’Ding, ding, ding! Guess I’ll spell it out, you’re gonna cosplay as a drow, a dark elf! So just sit there and be my pretty canvas will you?’’

‘’Uhm, al..right? This uh… will be easily removable right?’’

‘’Easy enough under a heavy shower, but hard enough so you don’t sweat it off.’’

‘’That’s fine, I guess…’’