Uptheraaaaa NSFW GIFs and Nudes - Discover Unknown Content

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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 1 month ago

11

Pegged by your sister

r/SissyCaptionStories

u/uptheraaaaa Captions Enjoyer 3 months ago

2364

Asking your roommate for sex advice

r/SissyCaptionStories

u/uptheraaaaa Sissy_dream 3 months ago

167

Bailey Jay is the goat

r/transandsissyporn

u/uptheraaaaa Mindless_Gooner BaileyGoat 4 months ago

163

It’s just an experiment

r/SissyCaptionStories

u/uptheraaaaa Sissy_dream 3 months ago

951

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

u/uptheraaaaa TimeForFun 1 month ago

874

Letting your mom use your hole isn’t gay, it’s the hormones!

u/uptheraaaaa Captions Enjoyer Miss_poizon 2 months ago

2162

Zoey Taylor fucking his throat

r/transandsissyporn

u/uptheraaaaa Draethas Zoey Taylor 2 months 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