Caption Pic: The Traption (Patreon)

Found the artist as https://www.deviantart.com/sandcasket

So it contains crossdressing and traps! Not always my thing, but a story or a pic that’s just right can be fun. I found a request on a thread for a crossdressing boy who comes to comfort a guy who was recently dumped by the boy’s older sister. The usual “Maybe I can be your girlfriend” angle comes up. Not for everyone, but thought it came out cute.

“Hey, man! I heard what happened last week! I can’t believe my dumb sis dumped you like that. She doesn’t know what she’s missing, so don’t be down. You’re better than her ugly ass anyway! You were always super cool about it when I wanted to play video games or I just felt like talking when she was in the shower.  Soooo I thought you might like it if I borrowed some of her old clothes and dressed up like this! She hasn’t worn them in years, so they didn’t fit her big as anyway (teehee)! I bet you didn’t think I was into this kind of thing, did you? I make a pretty convincing trap, don’t I? I just wanted you to see you get a way better girl than she ever was… a girl like her own little brother!

“Doesn’t that sound fun?! Just letting me be your girlfriend instead? I won’t argue over nothing or call you names… except for when you want me to, anyway~! It would get her soooo pissed if she found out you were fucking her femmy little brother! It’d be the perfect payback! And I promise you’ll love it! I’ve been watching lots of videos online just waiting for my chance to make you happy and show you I’m the better girl than her. I learned how to twerk and lapdance and I’ve been practicing with my toys at home. I even spied on you two once a couple years ago, so I know how to go down on you just how you like. Oh, don’t be so shy! I wasn’t being a creep~! I didn’t know what I was doing at the time!

“So what do you say? You can call me any names you want. You can fuck me anywhere you like~! You can stick it up my tight girly ass! You can put it between my glossy lips and let my pretty little face go to town on your cock! You can rub it on my abs or chest and just leave sticky trail all over your new girlfriend! We can even just rub dick to dicklet… I know you’re way bigger than I am, and I thought it might be a little confidence booster if we just frotted a little to let you show off. 

“Orrrr you can have my favorite! I can tuck mine back and let me be your girly girl! Then you can just stick it between my juicy thighs and I can just flex my legs to pump on your shaft like you’re fucking my sissy boy pussy! I can get them really tight so you’ll just love it! Here! I even recorded this on my phone… see? I kept wanting to build up the nerve to send it to you someday. It’s why you can hear me whisper your name if you listen real closely. But see? I can take it as deep as you want that way while you pull my hair or play with my boi titties or just kiss these shiny pink lips… anything to make you as happy as I was hanging out with you. You were like the cool older brother that I never had… and now you’re like the cool older boyfriend I never had~! 

“You will!? Yessss! I can’t wait to see what you’ll do to me! I know it’ll be a lot of fun and sexy as hell! Teehee! Now come on! Don’t leave your girlfriend waiting! I bet you’re all built up from not having my sister around, so you can use up all that needy cum on me!”

A couple of days ago, you went through a messy break-up with your gf. The gf little brother comes to your home, to comfort you.