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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 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 lowelltwink
11 months ago
New sister subreddits r/bostongoonbuds & r/bostongayss
in Boston
to r/Bostonsissys by lowelltwink
1 year ago
December 2022 Update- NEW POSTING RULES! Please Read!
in Boston
to r/Bostonsissys by No-Cod3644
5 hours ago
Preview thumbnail for 42 [S4A] #Boston - Leather clad sissy looking for fun image
42 [S4A] #Boston - Leather clad sissy looking for fun
Sissy
in Boston
to r/Bostonsissys by No-Cod3644
5 hours ago
42 [S4A] #Boston - Leather clad sissy in boston city
Sissy
in Boston
to r/Bostonsissys by Sea-Guarantee-569
2 days ago
25 [S4A] #Cambridge - Looking for someone to make me their sissy
Unverified
in Cambridge, Boston, MA
to r/Bostonsissys by ttvdd
1 day 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
4 days ago
34 [m4a] #quincy - can host or travel for oral fun tonight/tomorrow
M4A Unverified
in quincy
to r/Bostonsissys by SufficientReveal1382
3 days ago
Preview thumbnail for 28 [S4A] #Medford - hosting in hotel tomorrow afternoon image
28 [S4A] #Medford - hosting in hotel tomorrow afternoon
Unverified
in medford
to r/Bostonsissys by bostoncdliz
1 week ago
44 [T4M] #Newton - AFTERNOON MONDAY 11/18 ONLY...CD bottom hotel hosting masc tops
T4M
in Newton
to r/Bostonsissys by cdMistress
6 days ago
Preview thumbnail for 32 [s4s] #Peabody - cd looking for other cd or sub guys for tonight image
32 [s4s] #Peabody - cd looking for other cd or sub guys for tonight
Unverified
in Peabody
to r/Bostonsissys by Educational_Text_263
14 hours ago
28 [m4s] #northshore - need a smooth sissy
M Unverified
in Northshore
to r/Bostonsissys by Curi0usBoyyy
1 week ago
31 [M4A] #Northshore - feminize my virgin holes
M4A Looking for later
in Northshore
to r/Bostonsissys by Kaylasweets25
1 week ago
Preview thumbnail for 33 [S4A] #Boston - I’m back 🖤 image
33 [S4A] #Boston - I’m back 🖤
Unverified
in Boston
to r/Bostonsissys by SweetSissyMA
5 days ago
Preview thumbnail for 58 [S4a] #Pembroke - south shore sissy image
58 [S4a] #Pembroke - south shore sissy
Sissy
in Pembroke
to r/Bostonsissys by Glittering-Age-6477
1 week 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 Frosty-Sense-2726
1 week ago
Preview thumbnail for 22 [S4M] #Boston - who can give me my first real cock? image
22 [S4M] #Boston - who can give me my first real cock?
Unverified
in Boston
to r/Bostonsissys by Significant_Star3527
1 week 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 dannyb3671
5 days ago
23 [S4M] #revereBeach - Sissy looking for guys to film with (no face required)
Sissy
in RevereBeach
to r/Bostonsissys by jaysbbc27
1 week 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 bostoncdliz
2 weeks ago
44 [T4M] #Newton - AFTERNOON FRIDAY 11/11 ONLY...CD bottom hotel hosting masc tops
T4M
in Newton
to r/Bostonsissys by Sea-Guarantee-569
2 weeks ago
25 [S4A] #Cambridge - Looking for someone to make me their sissy
Unverified
in Cambridge, Boston, MA
to r/Bostonsissys by ReasonPsychological4
2 weeks 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
2 weeks 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
2 weeks ago
20 [m4s] #Boston - Looking to have some fun
M Unverified
in Boston
to r/Bostonsissys by usemyfaceee
2 weeks ago
31 [M4A] #Northshore - Use my throat
M4A PM's welcome
in Northshore