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
ottimo-massimo
Filter results by:
Posts
6446
Author
ottimo-massimo
Curl Up In Bed With Coiled Up Photography
PORN GALLERIES
December 9, 2011
OTTIMO-MASSIMO
Fighting Tooth And Getting Nailed: Asa Akira Vs. Bobbi Starr
PORNSTARS
December 9, 2011
OTTIMO-MASSIMO
Is It Still A Booty Call If You’re Only Looking For Head?
AMATEUR
December 9, 2011
OTTIMO-MASSIMO
Rise Of The Planet Of The “Monster Gapes”
HARDCORE
December 9, 2011
OTTIMO-MASSIMO
Comrades In Curves: Phoenix Marie Vs. Kagney Linn Karter
EDITORIAL FEATURES
December 9, 2011
OTTIMO-MASSIMO
Nicole Ray Knows How To Properly Milk A Gentleman
HARDCORE
December 8, 2011
OTTIMO-MASSIMO
A Blowjob Without Bedroom Eyes (Or, The Case For Deadpan Dome)
AMATEUR
December 8, 2011
OTTIMO-MASSIMO
Archrivals Of Alt-Porn: Kimberly Kane Vs. Andy San Dimas
EDITORIAL FEATURES
December 8, 2011
OTTIMO-MASSIMO
How To Select The Best Place To Come On Your Wife
AMATEUR
December 8, 2011
OTTIMO-MASSIMO
“Put It In My Ass” Not To Be Confused With “Putin In My Ass”
HARDCORE
December 8, 2011
OTTIMO-MASSIMO
255
256
257
258
259
Popular on Fleshbot
Ask Chad, Dating & Sex: Cold Feet, Chastity, & Penis Pumps
May 18, 2025
ANONYMOUS
Hot Male Libra Celebrities Baring It All Pt 2!
October 16, 2025
CELEBS
Hot Male Libra Celebrities Baring It All: Last Call!
October 21, 2025
CELEBS
These Ones Are Out There! Gay Kinks Explained
February 6, 2025
ALTERNATIVE
Hot Policemen In Uniform Bulging: Things We Find Hot
September 15, 2025
BUBBLE BUTTS
Categories
Pornstars
Hardcore
Editorial Features
Celebrity
Amateur
Sponsored
TV/Movies
Porn Galleries
Reviews
Bareback
Porn Deal of the Day
Bareback Plus
Bareback Plus: 50% Discount!
REDEEM NOW
Reality Dudes
Reality Dudes: 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
jasonstromm
40 years old
NickMoss
25 years old
DORIAN_LEVRONE
28 years old
AXEL_STIVENS
27 years old
rahiancopper
24 years old
RaelGomart
34 years old