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About this blog

What happens when  you add Puberty,  Midlife Crisis and  Menopause to a cocktail of Testosterone, Prep and Freedom. You get a ball dropping, asshole opening, heart stuttering free-fall off the deep end. And a mighty fine mess in your pants. 

 

 

Entries in this blog

Balls Deep

Swing Low

Back Boards   0   HenryBravo  #confessions · 1 attachment 1h ago · 3 Views Today I answered a strangers request to join him and five friends for a bang session that would leave me, as he promised , a fully used whore. I paid an extravagant amount of money on an Uber, traveled an hour with my pussy getting wetter and my ass getting thirstier.  He answers  the door naked. Middle aged, and  balding with a bit of a tummy. The house is huge, the tvs are huge, the
UrBoyHenry

UrBoyHenry in Balls Deep

1
Balls Deep

Testing a Link-

This is a test of  my human broadcasting System. Hopefully the link to my video on Xtube works. Upfront this  is maybe not the audience for my amatuer masturbation videos. But it is my experience from a unique vantage point. Video making and sharing is in part a Fetish but mostly it is a safe and creative expression of my mascu;inity. It stands as my proof, as my witness to the control I have over my body and my life. And that sentiment can be  indentified in each our of connnections.  In t
UrBoyHenry

UrBoyHenry in Balls Deep

0
Health

Brick a Bottom: A Bottoms Bottom

The biggest challenge in my gender transition has been learning how to douche my ass. Not the surgeries and the internal bleeding , not the coming out over and over again, not telling my father or my son that I was planning on having a glorious BBC of my own.  No , the hardest thing,  is the mostly mental block to, cleaning the waste out of the trash bin so to speak. The humiliation aspect of being that trash bin for strangers starts right there. I'd be remiss if I did not say that the preparing
UrBoyHenry

UrBoyHenry in Health

3
Balls Deep

B-Day Bare-ly Adulting

Today I am 43. I don't look it that's for dam sure and I sure as hell aint mad at being carded. It is quickly becoming an asset to my own dark dementors. I like my men older. I lost my virginity at 14 to a beautifully hung military man. And my 1st Dom at 18 was 40 years my elder. But this strikes a darker streak, a primal need to be consumed by my maker, to be destroyed by my own creator. And the dark perverted child in me  finds it funny when disapointment and confusion spreads across  the
UrBoyHenry

UrBoyHenry in Balls Deep

0
Balls Deep

Gay Wad

My entire life has been centered around sex. I found porn at an early age  and it was the answer. The Answer. To Everything. And it has been gay porn from the very first sight of a rock hard, ass smashing dick. Didn't matter if that ass was attached to a woman, all I have ever saw were those long girthy  beautiful schlongs of the 80's porn scene. Soft core compared to the filth that makes my little t-cock throb now a days. I was envious of that Dick, those balls and I have not lost any of my fas
UrBoyHenry

UrBoyHenry in Balls Deep

0
Wetdreams

Wetdreaming

This ride is intense. At forty I am trying to navigate the most massive  shift in my life,  from a pussy licking , leash holding Dom  to a wiggly bottom cum slut. This story is beautiful, disgusting, epic and pathetic. Life on T is not a game for the weak, young,  old or untested. This is expert level shit here son. Most of you would  have begged mercy, screamed uncle, tapped out and be well on your way home to momma by now, and we haven't even started.  This is the game that says I get to play
UrBoyHenry

UrBoyHenry in Wetdreams

0

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