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Boston

r/Bostonsissys

7,106 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 lowelltwink
1 year 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 bostoncdliz
6 days ago
44 [T4M] #Somerville - bottom at Main St. Video booths
T4M
in Somerville
to r/Bostonsissys by bostoncdliz
2 weeks ago
44 [T4M] #Burlington - Your slutty valentine...CD bottom needs cocks @ Marriott TODAY 2/14 AFTERNOON ONLY
T4M
in Burlington
to r/Bostonsissys by bostoncdliz
3 weeks ago
44 [T4M] #Newton - CD bottom needs cocks @ Marriott TODAY 2/6 DAYTIME
T4M
in Newton
to r/Bostonsissys by Careless-Editor7421
3 weeks ago
Preview thumbnail for 50 [M4S] #RI #Pawtucket - Any sissies into heavy smoking, heavy make-up, & getting bred? image
50 [M4S] #RI #Pawtucket - Any sissies into heavy smoking, heavy make-up, & getting bred?
M Man for Sissy
in Pawtucket, RI
to r/Bostonsissys by MaybeMaybeNot99999
3 weeks ago
32 [M4S] #Millis - Looking for partner for massage fantasy
M Man for Sissy
in millis
to r/Bostonsissys by bostoncdliz
4 weeks ago
44 [T4M] #Newton - CD bottom needs cocks @ Marriott MONDAY 2/3 DAYTIME
T4M
in Newton
to r/Bostonsissys by Extreme-Particular45
1 month ago
Preview thumbnail for 23 [S4M] #Boston - Feminine Twink looking for curious/manly daddy image
23 [S4M] #Boston - Feminine Twink looking for curious/manly daddy
Sissy
in Boston
to r/Bostonsissys by bostonbutt4u
1 month ago
Preview thumbnail for 28 [S4A] #Boston - Ready to pound me, taste me, or share me? Message me if you host or open to meeting at a hotel. Iā€™m Non-passable, I wear a mask. image
28 [S4A] #Boston - Ready to pound me, taste me, or share me? Message me if you host or open to meeting at a hotel. Iā€™m Non-passable, I wear a mask.
PM's welcome
in Boston
to r/Bostonsissys by bostonbutt4u
1 month ago
Preview thumbnail for 28 [S4A] #Boston - Ready to pound me, taste me, or share me? Message me if you want come by my hotel tonight. Iā€™m Non-passable, I wear a mask. image
28 [S4A] #Boston - Ready to pound me, taste me, or share me? Message me if you want come by my hotel tonight. Iā€™m Non-passable, I wear a mask.
Sissy
in Boston
to r/Bostonsissys by Able-Chef-8060
1 month ago
Preview thumbnail for 20 [s4a] #Boston - Cross dresser looking for friends! image
20 [s4a] #Boston - Cross dresser looking for friends!
Sissy
in Boston
to r/Bostonsissys by Sensitive-Rock-8713
4 weeks ago
36 [m4m] # Waltham -looking for daddy
M4M Unverified
in Boston
to r/Bostonsissys by Sensitive-Rock-8713
4 weeks ago
36 [m4m] #waltham
M4M
in waltham
to r/Bostonsissys by Joshcrayn1
1 month ago
Preview thumbnail for 23 [S4A] #south - just a fat ass sissy looking for a daddy or dom snap joshcrayn1 image
23 [S4A] #south - just a fat ass sissy looking for a daddy or dom snap joshcrayn1
Sissy
in South
to r/Bostonsissys by bostonhockeystuff
1 month ago
Preview thumbnail for 33 [M4M] #Salem - hung chub looking for fems, ts, twinks, swallowers, u host image
33 [M4M] #Salem - hung chub looking for fems, ts, twinks, swallowers, u host
M4M Unverified
in Salem, OR
to r/Bostonsissys by Extreme-Particular45
1 month ago
Preview thumbnail for 23 [S4M] #Boston - Feminine twink looking for curious/manly daddy image
23 [S4M] #Boston - Feminine twink looking for curious/manly daddy
Sissy
in Boston
to r/Bostonsissys by GrownGarden
1 month ago
19 [m4s] #newton - college dom looking for sissy
M Man for Sissy
in Newton
to r/Bostonsissys by bostoncdliz
1 month ago
Preview thumbnail for 44 [T4A] #Waltham Courtyard-available for use Friday 11am-5pm image
44 [T4A] #Waltham Courtyard-available for use Friday 11am-5pm
T4A
in waltham
to r/Bostonsissys by exodusplus
1 month ago
Preview thumbnail for 39 [M4M] #Randolph - I hope youā€™re wearing layers because baby, itā€™s cold outside. image
39 [M4M] #Randolph - I hope youā€™re wearing layers because baby, itā€™s cold outside.
M4M Unverified
in randolph
to r/Bostonsissys by bostoncdliz
1 month ago
44 [T4M] #Newton - Slut CD bottom for use @ Marriott 1/23-1/24 THURSDAY&FRIDAY AFTERNOONS
T4M
in Newton
to r/Bostonsissys by Alarming_Reindeer_16
1 month ago
Preview thumbnail for 34 [M4A] #Boston - Looking to meet for drinks 1/29 image
34 [M4A] #Boston - Looking to meet for drinks 1/29
M4A Man for Sissy
in Boston
to r/Bostonsissys by open_sub
1 month ago
25 [S4A] #MA - Bi/bicurious and looking to explore feminization through chat (femme people preferred)
PM's welcome
in Massachusetts
to r/Bostonsissys by bostonbutt4u
1 month ago
Preview thumbnail for 28 [S4A] #Boston - Ready to pound me, taste me, or share me? Message me if you want come by my hotel tonight. Iā€™m Non-passable, I wear a mask. image
28 [S4A] #Boston - Ready to pound me, taste me, or share me? Message me if you want come by my hotel tonight. Iā€™m Non-passable, I wear a mask.
PM's welcome
in Boston
to r/Bostonsissys by Consistent_Chart6370
1 month ago
31 [S4A] #Boston #RI - Sissy looking for friends
Sissy
in Rhode Island