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.

[+ Vegas_Millennial]

6 minutes ago, Wings246 said:

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?

You gotta get the lips in there too... Then everything starts touching everything... Combined with suction action and the gusto of eating ass like it's one's last meal at a time-limited all-you-can-eat buffet 🥳 

[Nue2thegame]

It helps if you can turn the butt inside out, too. 

[+ SirBillybob]

On 8/5/2026 at 7:33 PM, Vegas_Millennial said:

Well said. 

I still passionately remember my first time for each of those events described, and a few more!   Each first feels like popping a cherry 🍒.

My virginity was lost in a different order:  lots of groping 1, getting blown 2, fucking ass 3, blowing others 4, kissing 5, getting fucked 6, three-way 7, double penetration 8, orgy 9, being filmed 10, sex in the ocean 11, sex on the public deck of a cruise ship 12, watersports 13, bukkake 14, taking a penis with a Prince Albert 15, taking foot-long 16, saying "I love you" during sex 17, sitting on a rim chair 18,  poppers 19, getting fucked by my first HUGE cock (length and girth) 20,  my second hole reached by someone's tongue 21, taking four fingers at once 22, sex on the roof of a NYC apartment building during the day 23, successfully deepthroating my first HUGE cock 24, getting fisted (still working up to that one 🥳)

Because my list is a work in progress, I'm still a virgin in many areas. 😇 

Whew! I need a drink. Make it a double and make it schnappy 🍑

Keep them coming.

Maraschino cherry for garnish, if any can be located in the lost & found not beaten to a pulp. 

Edited Saturday at 07:57 PM by SirBillybob

[+ SirBillybob]

On 8/6/2026 at 6:05 PM, Nue2thegame said:

I was on my back and shot clear across the room.

Being the ball, noun not verb, seems risky no matter the starting position, although but a few metres is a meritorious canon.

Edited Saturday at 07:43 PM by SirBillybob

[+ SirBillybob]

The Prince Albert 15 appears to be a custom ring size order. Always a bridesmaid.

Edited Saturday at 07:43 PM by SirBillybob

[Nue2thegame]

On 8/6/2026 at 8:53 AM, PhileasFogg said:

By that standard, sides remain virgins.

 

Yes, and there’s a special place in the afterlife for them. 

[+ SirBillybob]

20 minutes ago, Nue2thegame said:

Yes, and there’s a special place in the afterlife for them. 

They are restricted to Virgin Mobile for Ouija contact. The rest of us dirtbags have more options including Fido. 

[+ PhileasFogg]

2 hours ago, Nue2thegame said:

Yes, and there’s a special place in the afterlife for them. 

Well, then I wonder where I stand as a bi-sexual….where side action is a gateway to expanded horizons 😉