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Boston

r/Bostonsissys

6,513 subscribers
A subreddit for sissy's and those interested in sissy's to meet people in the Boston area.

Part of the r/Bostongayss subreddit network! Please visit our sister subs:

r/bostongayss &
r/bostongoonbuds

Moderators

Updated Apr 9, 2024
u/lowelltwink Active
Added 4 years ago
Also moderates: r/bostongayss, r/bostongoonbuds
u/Traditional_Bid_3139 Active
Added 11 months ago

Notice: This subreddit is not actively monitored, so the posts here are only a small subset of what exists on reddit.

Browse by flair

Looking for later Looking for now Man for Sissy Woman for Sissy PM's welcome Sissy Verified Verified Unverified
New Top (24hr) Top (Week) Top (Month)
to r/Bostonsissys by xo10xo
1 month ago
Preview thumbnail for 25 [t4m] #boston - visiting and hosting this Thurs image
25 [t4m] #boston - visiting and hosting this Thurs
T4M Unverified
in Boston
to r/Bostonsissys by TransPantiesNylons
1 month ago
Preview thumbnail for 52 [T4A] #NorthOfBoston - Trans Sissy, 16 Months on E image
52 [T4A] #NorthOfBoston - Trans Sissy, 16 Months on E
T4A Sissy
in northofboston
to r/Bostonsissys by Sissyrosexx
4 months ago
Preview thumbnail for 22 [T4M] #Woburn - Sissy slut looking for a daddy image
22 [T4M] #Woburn - Sissy slut looking for a daddy
T4M Unverified
in Woburn
to r/Bostonsissys by sissyaznCDnweglnd
3 months ago
28 [T4M] #Boston - Passable fem Asian CDer hosting str8 guy
T4M Unverified
in Boston
to r/Bostonsissys by sissyaznCDnweglnd
4 months ago
28 [T4M] #Boston - Passable fem Asian CDer hosting str8 guy
T4M Sissy
in Boston
to r/Bostonsissys by latinax7
4 months ago
Preview thumbnail for 25 [t4m] #Boston - looking visting and hosting image
25 [t4m] #Boston - looking visting and hosting
T4M Unverified
in Boston
to r/Bostonsissys by Sissyrosexx
4 months ago
22 [T4M] #Woburn - Sissy slut looking for right now
T4M Unverified
in Woburn
to r/Bostonsissys by Sissyrosexx
4 months ago
22 [T4M] #Woburn - Sissy CD looking for morning fuckbuddy
T4M Unverified
in Woburn
to r/Bostonsissys by sissyaznCDnweglnd
5 months ago
28 [T4M] #Boston - Passable fem Asian CDer hosting str8 guy
T4M Sissy
in Boston
to r/Bostonsissys by Sissyrosexx
5 months ago
22 [T4M] #Woburn - Sissy slut looking for anyone around this fine morning
T4M Unverified
in Woburn
to r/Bostonsissys by Sissyrosexx
5 months ago
22 [T4M] #Woburn - Sissy CD looking for morning hookups
T4M Unverified
in Woburn
to r/Bostonsissys by Medium-Heart-2445
2 months ago
Preview thumbnail for 40 [T4A] #Dedham - seeking a Top image
40 [T4A] #Dedham - seeking a Top
T4A Looking for now
in Dedham
to r/Bostonsissys by Sissyrosexx
5 months ago
22 [T4M] #Woburn - Sissy slut looking for tomorrow
T4M Unverified
in Woburn
to r/Bostonsissys by RoleProfessional4902
7 months ago
Preview thumbnail for 27 [T4A] #Boston - Femboy / CD looking for FWB :) image
27 [T4A] #Boston - Femboy / CD looking for FWB :)
T4A Unverified
in Boston
to r/Bostonsissys by curious_sis232
8 months ago
23 [T4A] #boston - ladies man looking to be force feminized
T4A Sissy
in Boston
to r/Bostonsissys by curious_sis232
9 months ago
23 [T4A] #boston - ladies man looking to be force feminized
T4A Sissy
in Boston
to r/Bostonsissys by sissyaznCDnweglnd
9 months ago
28 [T4M] #boston - Azn cder hosting str8 guy for breeding
T4M Sissy
in Boston
to r/Bostonsissys by curious_sis232
9 months ago
23 [T4A] #boston - stud looking to be force feminized
T4A Sissy
in Boston
to r/Bostonsissys by SubmissiveScreamer
10 months ago
Preview thumbnail for 46 [T4M] #SouthShore - tall lean soft smooth exotic fem sissy looking for Big Srong Alpha Str8 M top image
46 [T4M] #SouthShore - tall lean soft smooth exotic fem sissy looking for Big Srong Alpha Str8 M top
T4M Unverified
in SouthShore
to r/Bostonsissys by SubmissiveScreamer
10 months ago
46 [t4m] #Weymouth - Submissive sissy looking to be used by rough str8 men
T4M Unverified
in Weymouth
to r/Bostonsissys by meuserme
11 months ago
Preview thumbnail for 42 [T4M] #Wilmington - sending me nudes will make my day and if your face is still attached will make my week😘😊 image
42 [T4M] #Wilmington - sending me nudes will make my day and if your face is still attached will make my week😘😊
T4M Unverified
in Wilmington
to r/Bostonsissys by BadInterest
4 months ago
Preview thumbnail for 33 [T4A] #Boston - Looking to Chat and Maybe Meet Someone Nice on a Lazy Sunday image
33 [T4A] #Boston - Looking to Chat and Maybe Meet Someone Nice on a Lazy Sunday
T4A
in Boston
to r/Bostonsissys by meuserme
1 year ago
Preview thumbnail for 42 [T4M] #Wilmington - little spoon image
42 [T4M] #Wilmington - little spoon
T4M
in Wilmington
to r/Bostonsissys by meuserme
1 year ago
Preview thumbnail for 42 [T4M] #Wilmington - guys who aren't camera shy! image
42 [T4M] #Wilmington - guys who aren't camera shy!
T4M
in Wilmington
to r/Bostonsissys by meuserme
1 year ago
Preview thumbnail for 42 [T4A] #Wilmington - too warm for layers image
42 [T4A] #Wilmington - too warm for layers
T4A
in Wilmington