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
calamitous
Filter results by:
Posts
1984
Author
calamitous
Van Darkholme, Spencer Reed, Patrick Rouge, Drake Jaden, Tyler Saint, & Nick Moretti (Bound Gods)
EDITORIAL FEATURES
February 17, 2010
CALAMITOUS
K.O.
February 16, 2010
CALAMITOUS
Well, There’s London And That’s France, So This Must Be…
February 16, 2010
CALAMITOUS
Who Wears Short-Shorts?
February 16, 2010
CALAMITOUS
Anything Would Be Hotter Than A New Yorker Right Now: Ba-Dum-Ching!
HARDCORE
February 16, 2010
CALAMITOUS
Andy Newtown & Elias Mathews (Dirty Boy Video)
EDITORIAL FEATURES
February 16, 2010
CALAMITOUS
Pre-Wedding Anxiety or A Waiter Standing Over A Pot of Clam Chowder?
February 15, 2010
CALAMITOUS
Rock N’ Roll Iconography
February 15, 2010
CALAMITOUS
This Man’s Butt Could Snap You In Half
February 15, 2010
CALAMITOUS
Skinny Love
HARDCORE
February 15, 2010
CALAMITOUS
83
84
85
86
87
Popular on Fleshbot
Grindr Fails: Golddiggers, Construction Guys, & Dirty Bottoms
January 22, 2026
ANONYMOUS
Throwback Thursday: On This Day, January 8th: A Trans First, Bowie’s Birth, and Milk Takes Office
January 8, 2026
CELEBS
Oscar Nominated Lead Actors and Their Skin Scenes
January 24, 2026
CELEBS
Muscle Guy on Muscle Stud Action: Happy Hump Day!
February 11, 2026
BULGES
Jordan Starr: The 2026 GAYVNs and the Future of Creator-Studio Unity
January 5, 2026
BIG DICKS
Categories
Pornstars
Hardcore
Editorial Features
Celebrity
Amateur
Sponsored
TV/Movies
Porn Galleries
Reviews
Pop Culture
Porn Deal of the Day
Guys in Sweatpants
Guys in Sweatpants: 89% Discount!
REDEEM NOW
Maverick Men Directs
Maverick Men Directs: 85% 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
kavethekake
30 years old
BoyHot_Mio
23 years old
jackwesker
23 years old
Max_Steell
18 years old
ChocolateBrum
39 years old
SexEntendido
42 years old