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
gay advice column
Tag
gay advice column
Ask Chad Sex & Dating: Throuples, Voyeurs, & Friends Divided
ASK CHAD WEEKLY
July 12, 2025
ALEXANDER
Ask Chad Dating: Prideless Gays, Doomed Dans, & Porn Watchers
ASK CHAD WEEKLY
June 28, 2025
ALEXANDER
How To Handle Rejection, the Fleshbot Gay Way
LOVE AND DATING
June 10, 2025
ALEXANDER
Ask Chad Gay Dating: Corporate Cock, Dumb Guys, & Picky Petes
ASK CHAD WEEKLY
June 9, 2025
ALEXANDER
Ask Chad, Dating & Sex: Cold Feet, Chastity, & Penis Pumps
ASK CHAD WEEKLY
May 18, 2025
ALEXANDER
Ask Chad Gay Sex & Dating: Fresh Meat, Hungry 3somes, & Tacky TikTok
ASK CHAD WEEKLY
April 28, 2025
ALEXANDER
Ask Chad Gay Sex & Dating: Bestie Crushes, Financial Freddys, & Bad BFs
ASK CHAD WEEKLY
April 6, 2025
ALEXANDER
Ask Chad Gay Sex & Dating: Sad Sofas, Escorts, & Bad Gays
ASK CHAD WEEKLY
March 29, 2025
ALEXANDER
Ask Chad Gay Sex & Dating: Foreskin, Serial Dater, & Hung BFs
LOVE AND DATING
March 21, 2025
ALEXANDER
Stop Doing This During Sex! Chad Speaks
SEX TIPS
February 7, 2025
ALEXANDER
1
2
3
4
Popular on Fleshbot
Henry Golding’s First Nude Scene Plus Jon Hamm’s Return
May 11, 2025
BUBBLE BUTTS
The Art of the Hotel Hookup
January 29, 2025
ANONYMOUS
Will Anthony Bowens Become the First Gay AEW Singles Champ?
April 14, 2025
HOT CELEBS
This Muscled Tattoo Stud Has A Perfect Chest & Hot Adult Content
October 13, 2025
BIG DICKS
Nicholas Galitzine Reveal As He-Man, Thick Thighs Save Lives
June 17, 2025
CELEBS
Categories
Pornstars
Hardcore
Editorial Features
Celebrity
Amateur
Sponsored
TV/Movies
Porn Galleries
Reviews
Bareback
Porn Deal of the Day
Say Uncle
Say Uncle: 33% Discount!
REDEEM NOW
Fun Size Boys
Fun Size Boys: 52% 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
HayesWood
31 years old
Leo_Hot_049
23 years old
FloydC19
29 years old
HappyPirate69
41 years old
Cameros_Pierce
18 years old
vliamper
24 years old