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Boston

r/Bostonsissys

6,711 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 5 years ago
Also moderates: r/bostongayss, r/bostongoonbuds
u/Traditional_Bid_3139 Active
Added 1 year 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 Automatic-Context-87
2 minutes ago
25 [m4s] #everett - first time
M Unverified
in everett
to r/Bostonsissys by MAtossaway
1 week ago
Preview thumbnail for 54 [M4A] #Tewksbury - looking for a play partner and maybe more image
54 [M4A] #Tewksbury - looking for a play partner and maybe more
M4A Unverified
in Tewksbury
to r/Bostonsissys by NoPast6431
5 days ago
Preview thumbnail for 46 [m4s] #worcester - Release image
46 [m4s] #worcester - Release
M Unverified
in Worcester
to r/Bostonsissys by DB_View_3912
1 week ago
Preview thumbnail for 19 [m4m] #bridgewater - sissy looking for a top dtf image
19 [m4m] #bridgewater - sissy looking for a top dtf
M4M Unverified
in Bridgewater
to r/Bostonsissys by GrownGarden
1 week ago
19 [M4A] #Newton - fit tall guy looking for women, femboy/ sissies
M4A Unverified
in Newton
to r/Bostonsissys by NogamesJustFun
1 week ago
40 [m4t] #Boston - Looking for a spicy connection
M4T Man for Sissy
in Boston
to r/Bostonsissys by One_Quail_9342
2 weeks ago
31 [M4S] #Quincy - looking for sissy for car play
M Unverified
in quincy
to r/Bostonsissys by dad-lking-for-boy
1 week ago
58 [M4M] #Newton to Wilmington- Looking to train younger
M4M Man for Sissy
in Newton
to r/Bostonsissys by dad-lking-for-boy
1 week ago
58 [M4M] #Newton to Wilmington- Looking to train younger
M4M Man for Sissy
in Newton
to r/Bostonsissys by ttvdd
2 weeks ago
23 [M4T] #Boston - ive had a sissy fantasy for a while help me with that ;)
M4T Unverified
in Boston
to r/Bostonsissys by Sharp-Raccoon-6650
3 weeks ago
34 [m4a] #quincy - can host or travel for oral fun tonight/tomorrow
M4A Unverified
in quincy
to r/Bostonsissys by MaybeMaybeNot99999
2 weeks ago
32 [M4S] #Millis - Looking for partner for massage fantasy
M Unverified
in millis
to r/Bostonsissys by Educational_Text_263
2 weeks ago
28 [m4s] #northshore - need a smooth sissy
M Unverified
in Northshore
to r/Bostonsissys by Curi0usBoyyy
3 weeks ago
31 [M4A] #Northshore - feminize my virgin holes
M4A Looking for later
in Northshore
to r/Bostonsissys by Glittering-Age-6477
3 weeks ago
Preview thumbnail for 24 [M4M] #Boston - looking for a daddy to explore my fem side image
24 [M4M] #Boston - looking for a daddy to explore my fem side
M4M Unverified
in Boston
to r/Bostonsissys by Significant_Star3527
3 weeks ago
Preview thumbnail for 21 [M4T] #Boston - Who wants to be next? image
21 [M4T] #Boston - Who wants to be next?
M4T Unverified
in Boston
to r/Bostonsissys by jaysbbc27
3 weeks ago
Preview thumbnail for 27 [m4a] #Taunton - who’s near by and wanna fuck I travel image
27 [m4a] #Taunton - who’s near by and wanna fuck I travel
M4A Unverified
in Taunton
to r/Bostonsissys by ReasonPsychological4
1 month ago
Preview thumbnail for 25 [M4A] #SouthShore - it’s cold out help me stay warm image
25 [M4A] #SouthShore - it’s cold out help me stay warm
M4A Unverified
in SouthShore
to r/Bostonsissys by Baggaroo
1 month ago
Preview thumbnail for 22 [M4S] #Worcester - 8.5 BWC Curious gl guy looking for cute ts gf or femboy to have some fun. Swipe for surprise ;) image
22 [M4S] #Worcester - 8.5 BWC Curious gl guy looking for cute ts gf or femboy to have some fun. Swipe for surprise ;)
M Unverified
in Worcester
to r/Bostonsissys by Additional_Run_3567
1 month ago
20 [m4s] #Boston - Looking to have some fun
M Unverified
in Boston
to r/Bostonsissys by usemyfaceee
1 month ago
31 [M4A] #Northshore - Use my throat
M4A PM's welcome
in Northshore
to r/Bostonsissys by usemyfaceee
1 month ago
31 [M4A] #Saugus - train my throat tonight
M4A Looking for later
in Saugus
to r/Bostonsissys by Significant_Star3527
3 weeks ago
Preview thumbnail for 21 [M4T] #Boston - can I put this in your ass? image
21 [M4T] #Boston - can I put this in your ass?
M4T Unverified
in Boston
to r/Bostonsissys by this-account-is-junk
1 month ago
31 [M4S] #somerville - Hosting this weekend
M Man for Sissy
in Somerville
to r/Bostonsissys by chrondorondo
1 month ago
18 [M4M] #Beverly - I NEED SOME D ASAPPP
M4M Unverified
in Beverly