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
love and dating
Tag
love and dating
Ask Chad Love and Dating: Facials, Bad Dressers, & Single Guys
ASK CHAD WEEKLY
May 23, 2024
ALEXANDER
Ask Chad Love and Dating: Load Takers, Douchey Besties, & Prudish Peckers!
ANONYMOUS
May 2, 2024
ALEXANDER
Ask Chad Love and Dating: Porn Boyfriends, Balding Boyfriends, & Gassy Ass
ASK CHAD WEEKLY
April 24, 2024
ALEXANDER
Ask Chad Love and Dating: Cheaters, Straight Guys, & Bored Besties
ASK CHAD WEEKLY
April 14, 2024
ALEXANDER
Ask Chad Love and Dating: Sleepovers, Mama’s Boys, and Party Poopers!
ASK CHAD WEEKLY
April 7, 2024
ALEXANDER
Ask Chad Love and Dating: Kissing Karens, Dog Days, and Low Libido
ASK CHAD WEEKLY
March 30, 2024
ALEXANDER
Ask Chad Love and Dating: Grindr Fails, Drag Queens, & Quick Dicks!
ASK CHAD WEEKLY
March 22, 2024
ALEXANDER
Ask Chad Love and Dating: Bisexual Boyfriends, OnlyFans Addicts, & Closeted Hookups!
ASK CHAD WEEKLY
March 15, 2024
ALEXANDER
Ask Chad Love and Dating: Office Sex, Slutty Besties, & Lace Underwear!
ASK CHAD WEEKLY
February 20, 2024
CHAD
Ask Chad Love and Dating: Nosy Neighbors, Broke Bitches, and Almost Threesomes
ASK CHAD WEEKLY
February 5, 2024
CHAD
1
2
3
4
5
Popular on Fleshbot
For the Love of the Harness: Kink & Fashion
April 1, 2025
BDSM
OnlyFans Users Could Face Prison In Sweden!
May 22, 2025
BREAKING NEWS
Major Grindr Changes for 2025: Here’s What’s Cumming
January 24, 2025
ANONYMOUS
Out Olympian & Hottie Dan Jervis Announces Retirement
February 21, 2025
CELEBS
Actor Brandon Flynn Is Giving Us More Bulge!
July 23, 2025
BULGES
Categories
Pornstars
Hardcore
Editorial Features
Celebrity
Amateur
Sponsored
TV/Movies
Porn Galleries
Reviews
Bareback
Porn Deal of the Day
Next Door Taboo
Next Door Taboo: 67% Discount!
REDEEM NOW
Hung Young Brit
Hung Young Brit: 87% 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
Photo1960
65 years old
VanVelckan
32 years old
sttewartdmateo19
19 years old
Erickblake
27 years old
MaxKaiden
22 years old
LordDominik
36 years old