What / When is considered loss of virginity for a gay man?

[Nightowl]

45 minutes ago, ShortCutie7 said:

Strangely enough, that was the only time I have ever enjoyed bottoming… for some reason my first time didn’t hurt, but every time I bottomed after that first time was painful and I was uncomfortable for hours if not days after. 

I hear ya.  I like the idea of bottoming and enjoy it when it’s slow and careful but when it’s the pile-driver technique that causes me to wince with every thrust, I can do without.  Loved your story though. We should all have an introduction to gay sex as erotic as that. 

[samhexum]

The first night of his prison sentence?

[Wings246]

11 hours ago, Vegas_Millennial said:

It was an ecclesiastical being:  an Angel 😇 

BulgingAngel

This reminds me of Yoshi's signature tongue attack: it lets him stretch his long tongue out to grab items, swallow enemies whole, and turn foes into eggs.

[nate_sf]

On 8/6/2026 at 10:14 PM, Wings246 said:

I'm amused, amazed, intrigued, and puzzled all at once when I read this, but am I reading this right?  The word here is "tongue," correct?  Is a normal, average human tongue long enough to achieve this goal?  Is this even anatomically possible?  Did you lose your virginity #21 to a chameleon or an alien?   😆

 

 

[Wings246]

For @Vegas_Millennial and anyone else who's experienced in the tongue & 2nd hole Holy Grail:

 

Now, all jokes aside, I’m genuinely curious about how this is physiologically possible.

The distance from the rectosigmoid junction (2^nd hole) to the anus is typically around 6 inches.  The Guinness World Records has documented unusually long tongue protrusion of about 4 inches beyond the lips.  The math is not mathing???  Did you meet someone with a >6-inch tongue?  Or, is it more about the technique & eagerness than the physical measurements?

Please enlighten & educate me, for I’m still pretty ignorant.