Uptheraaaaa NSFW GIFs and Nudes - Latest Feed

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Created

05/30/2025

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R/transandsissyporn

You finally gave in. Your roommate always expressed how feminine you look, he wanted to fill you with his hot cum… but it’s not gay

u/uptheraaaaa TimeForFun 2 weeks ago

11

Your boss brought you into his office to fire you. You told him you’d do anything to keep the job

u/uptheraaaaa TimeForFun 2 weeks ago

874

Bailey Jay is the goat

r/transandsissyporn

u/uptheraaaaa Mindless_Gooner BaileyGoat 3 months ago

163

Zoey Taylor fucking his throat

r/transandsissyporn

u/uptheraaaaa Draethas Zoey Taylor 1 month ago

284

Your sister takes such good care of your cock, hopefully your wife doesn’t find out

r/Incest_Captions

u/uptheraaaaa KT 2 months ago

1665

You didn’t wake up at 6:30… ;)

r/SissyCaptionStories

u/uptheraaaaa Nottaboocaption 2 months ago

683

Pegged by your sister

r/SissyCaptionStories

u/uptheraaaaa Captions Enjoyer 2 months ago

2364

Asking your roommate for sex advice

r/SissyCaptionStories

u/uptheraaaaa Sissy_dream 2 months ago

167

It’s just an experiment

r/SissyCaptionStories

u/uptheraaaaa Sissy_dream 2 months ago

951