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
Articles
Everybody Can Appreciate A Good Pair of Boobs
PORNSTARS
November 3, 2009
CALAMITOUS
This Is The Best Vacation Ever
PORNSTARS
November 3, 2009
CALAMITOUS
The Pleasure Principle
HARDCORE
November 3, 2009
CALAMITOUS
Naked Clowns Will Either Give You Boners or Tears
PORNSTARS
November 3, 2009
BRIAN-O-BRIEN
It Looks Like It’s Time To Teach Pornstars How To Name Themselves Again
PORNSTARS
November 3, 2009
BRIAN-O-BRIEN
Takin’ Toy For A Ride (Dirty Boy Video)
EDITORIAL FEATURES
November 3, 2009
CALAMITOUS
Pirate’s Booty Trailer
EDITORIAL FEATURES
November 3, 2009
LUX-ALPTRAUM
We’re In Love With Everything About These Thugs
PORNSTARS
November 3, 2009
BRIAN-O-BRIEN
Sweet and Raw: Jerry, Nick and Thomas
BAREBACK
November 2, 2009
FLESHBOT WRITER
The Rats And Children Follow Me Out Of Town
PORNSTARS
November 2, 2009
CALAMITOUS
2505
2506
2507
2508
2509
Popular on Fleshbot
February 13th Roundup: The Best of the Butts, Bulges, and Beefcakes
February 13, 2026
BIG DICKS
Football Butts and Bulges: For the Love of Sports Guys
February 13, 2026
BUBBLE BUTTS
The Dylan O’Brien Nude Gay Sex Scene We Deserve
January 25, 2026
CELEBS
Thick DILFS Who Are Packing Major Meat & Heat
January 3, 2026
BEARS
Gay Group Sex Done Right: The Chad Way
January 31, 2026
ASK CHAD WEEKLY
Categories
Pornstars
Hardcore
Editorial Features
Celebrity
Amateur
Sponsored
TV/Movies
Porn Galleries
Reviews
Pop Culture
Porn Deal of the Day
Staxus
Staxus: 25% OFF
REDEEM NOW
Sean Cody
Sean Cody: 40% 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
Alexx_North
24 years old
schnneider18
23 years old
NoirWarden
34 years old
jarethh
18 years old
Darwin_mayo
22 years old
LeoSantoro22
22 years old