Loading...
Light
Dark
Straight
Gay
Trans
Biz
Home
Straight
Gay
Trans
Business
Categories
Pornstars
Amateur
Hardcore
Porn Galleries
Editorial Features
Celebrity
TV/Movies
Sponsored
Politics
Fleshlight
Shop
Creators
The Gay List
The Gay List
The List
Business List
Porn Deals
LIVE Sex
XXX TikTok
Straight
Gay
Trans
Biz
Straight
Gay
Trans
Biz
Home
Straight
Gay
Trans
Categories
Pornstars
Editorial Features
Hardcore
Celebrity
Creators
Porn Galleries
TV/Movies
Amateur
Sponsored
Shop
Creators
The Gay List
The Gay List
The List
Business List
Porn Deals
LIVE Sex
XXX TikTok
cumshots
Tag
cumshots
How About Getting Some Wood in the Woods?
EDITORIAL FEATURES
October 12, 2011
BRIAN-O-BRIEN
This Video Is Like a Work of Art
EDITORIAL FEATURES
October 11, 2011
BRIAN-O-BRIEN
This Boy Is a Sex Slave For You
EDITORIAL FEATURES
October 11, 2011
BRIAN-O-BRIEN
We’re Having a Hot Headless Masturbation Overload
EDITORIAL FEATURES
October 7, 2011
BRIAN-O-BRIEN
Would You Hit Yourself in the Nuts?
EDITORIAL FEATURES
October 6, 2011
BRIAN-O-BRIEN
This Is What the Gay Porn Witness Protection Program Looks Like
EDITORIAL FEATURES
October 5, 2011
BRIAN-O-BRIEN
Now This Is What They Call Knocking Boots
EDITORIAL FEATURES
October 4, 2011
BRIAN-O-BRIEN
This Is the Sexiest Nerd in the World
EDITORIAL FEATURES
October 3, 2011
BRIAN-O-BRIEN
This Boy Is Rapidly Becoming Our Favorite Internet Masturbater
EDITORIAL FEATURES
September 30, 2011
BRIAN-O-BRIEN
What’s Love Got to Do with This?
EDITORIAL FEATURES
September 29, 2011
BRIAN-O-BRIEN
49
50
51
52
53
Popular on Fleshbot
Kinks You Probably Never Heard Of
July 30, 2025
BDSM
Muscle Footballer Stud Miguel Guerrero on OnlyFans!
March 26, 2025
BULGES
Underwear Lines & Jockstraps On Sports Guys: Happy Hump Day!
June 18, 2025
BUBBLE BUTTS
Ask Chad Sex & Dating: Throuples, Voyeurs, & Friends Divided
July 12, 2025
ANONYMOUS
Ask Chad Sex & Dating: Broke Asses, Hung Hoes, & Debbie Downers!
January 21, 2025
ASK CHAD WEEKLY
Categories
Pornstars
Hardcore
Editorial Features
Celebrity
Amateur
Sponsored
TV/Movies
Porn Galleries
Reviews
Bareback
Porn Deal of the Day
Men
Men: 40% Discount!
REDEEM NOW
Men at Play
Men At Play: 50% Discount!
REDEEM NOW
Trending Creators
Newest Adds
Featured
Free Accounts
Most Liked
VIEW ALL CREATORS
Newsletter Signup
Stay Updated on all Fleshbot Updates
Subscribe Now
Hey Chad,
I am typically a top and have limited experiences bottoming, and the reason is because it hurts too much. Every time I go through the same thing, clean out, hype myself up, poppers, lube, and try taking it slow. But the outcome is always the same, it hurts and I can’t enjoy myself and then stop him after a few minutes because it is too unbearable. How do I bottom without it feeling like I’m passing a watermelon?
Thanks,
- Novice Bottom
Chad,
There’s nothing that ticks me off more than a flake, and lately, I keep getting ghosted on the apps. I get tons of messages when I first log on but by the time I am ready, or the later it gets, the more likely they are to flake on me and then I end up finishing myself and going to sleep. How do I get a hookup to come through?
SOS,
- Night Owl
Dear Chad,
I am a little annoyed to have to even ask this but what is the policy on paying for dates? I recently went out with a guy for the second time now and I had to pay for everything BlOTH TIMES. He didn’t even reach for his wallet when the waiter brought the bill, or when we went to the movies! I feel like that’s so rude, like it should be his turn the second time right? Or do I have to say something about splitting the bill from the beginning?
Thanks,
- NotUrSugarDaddy
Stay In Touch
Live Sex
view more
AustinRex69
24 years old
ashttoncooper
28 years old
xxwankywaynexx
19 years old
TooDamnFire
33 years old
strongboyxl
23 years old
Spartacus77
43 years old