Loading...
Light
Dark
Straight
Gay
Trans
Biz
POWERED BY
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
boston
Tag
boston
Queer Fall Calendar – What To Do This Fall In the North East
EVENTS
September 27, 2023
TOMMY
Hey Gurl! with Jordan Jayro: Fena Barbitall Talks Topping, Botox, & Wigs
PODCAST
July 31, 2023
JORDAN JAYRO
MLB Stud Creates Queer Playlist for Game in Honor of Pride Night and We CANNOT ‘Calm Down’
SPORTS - ATHLETES
June 22, 2023
TOMMY
Grindr Fails: Boston Creampies, Fisting, And Tall Bottoms
GRINDR FAILS
May 18, 2023
JORDAN JAYRO
White Trash Wednesday Returns With a Smoking JO, a Self-Facial, and a Straight Boy BJ
AMATEUR
July 27, 2022
HANK ORSO
Take a Load Off: The Best Gay Escorts & Gay Massage in Boston
SPONSORED
November 11, 2016
FLESHBOT
Our Exclusive Interview With That Most Devious Of Mammals: Deviant Otter
PORNSTARS
September 12, 2014
VINCENT-THRICE
Straight Dudes Jerking Off! (Well, Sorta)
PORNSTARS
October 29, 2007
JONNO
Popular on Fleshbot
Grindr Fails: Foreskin, Guys on the DL, and Roleplay
May 5, 2025
ANONYMOUS
Hot Men In Speedos
June 16, 2025
BUBBLE BUTTS
Hot Male Taurus Celebrities Showing It All Off!
April 21, 2025
BUBBLE BUTTS
Confidence In the Bedroom Is Sexy, Get Over Yourself! Chad Speaks
January 27, 2025
ASK CHAD WEEKLY
Dylan Tides Gets Close with Dear Old Daddy for Carnal+
February 10, 2025
BAREBACK
Categories
Pornstars
Hardcore
Editorial Features
Celebrity
Amateur
Sponsored
TV/Movies
Porn Galleries
Reviews
Bareback
Porn Deal of the Day
Badpuppy
Badpuppy: 50% Discount!
REDEEM NOW
Family Dick
Family Dick: 50% 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
MalconStonne
28 years old
reganjhonson
26 years old
RickDiesel
28 years old
GreenDylan
28 years old
AlexGrey77
24 years old
chuppa
60 years old