r/sissy_caption

Pick one sissy

▲ 141 r/sissy_caption

Pick one sissy

u/Captionlife — 7 hours ago

▲ 62 r/sissy_caption+5 crossposts

Doesn't count if you're drunk ;)

u/SissyStoriesOne — 3 hours ago

▲ 52 r/sissy_caption

Isn't this every sissy's dream come true?

u/SissyWhiteboy000 — 3 hours ago

▲ 502 r/sissy_caption+7 crossposts

sissy bud likes to dress up like a girl.. 😳

u/mias2bad4u — 9 hours ago

▲ 557 r/sissy_caption+16 crossposts

u/BubbleButtSis22 — 9 hours ago

▲ 422 r/sissy_caption+20 crossposts

u/BubbleButtSis22 — 9 hours ago

▲ 132 r/sissy_caption+7 crossposts

Time for your next lesson 💜

u/Big_Kangaroo7795 — 7 hours ago

▲ 228 r/sissy_caption+9 crossposts

u/BubbleButtSis22 — 9 hours ago

▲ 751 r/sissy_caption+4 crossposts

She wouldn't even feel you

u/Loose_Theory8000 — 12 hours ago

▲ 264 r/sissy_caption+5 crossposts

Your Friend bet you to dress as a girl, but his HUGE COCK down your THROAT wasn't part of the bet! (Part 1)

u/BubbleButtSis22 — 9 hours ago

▲ 142 r/sissy_caption+8 crossposts

u/BubbleButtSis22 — 9 hours ago

▲ 976 r/sissy_caption+7 crossposts

Sissy Gets Manhandled By Real Man 😈🍆🍑 (Sissy Captions)

u/Suspicious-Cut5540 — 14 hours ago

▲ 121 r/sissy_caption+4 crossposts

Your friend always walks around with his HUGE DICK out! (Part 1)

u/BubbleButtSis22 — 9 hours ago

▲ 103 r/sissy_caption+2 crossposts

BIG DICK Friend takes your virginity (Part 1)

u/BubbleButtSis22 — 9 hours ago

▲ 2.1k r/sissy_caption+2 crossposts

soft fpov (weirdfish44)

u/Wooden_Kick_8599 — 20 hours ago

▲ 1.2k r/sissy_caption+19 crossposts

You spent years wondering why things never worked with girls, until you bought that toy and realized exactly what you were actually craving

u/secret_benefits — 22 hours ago

▲ 696 r/sissy_caption+5 crossposts

Sissy is not a choice 🤭

u/Roob_Uber — 22 hours ago

▲ 546 r/sissy_caption+1 crossposts

Better than a girl really 😱

u/Bottom4Shemales1 — 23 hours ago

▲ 3.1k r/sissy_caption+7 crossposts

Choose One, Cumslut

u/EliasCaptions — 1 day ago

▲ 818 r/sissy_caption+8 crossposts

We all need a friend like that sometimes

u/Purple-Cheesecake-11 — 1 day ago