Gay friend [36] and his bf [37] made a funny bet awkward

Not a question

I want to caveat this by saying, if I’m being homophobic or insensitive at all then I apologise and it’s not intentional.

I’ve been friends for years with them, other than one very drunk incident, there’s never been any stepping past the line of friends.

We bet on the World Cup, as my friends bf is Spanish, I had France (I’ve got loose family roots) and my friend has Argentina.

If I won the next time we go away on holiday (as part of a larger group) they’d cover my meals and drinks the entire time.

If I lost, I’d let them put a butt plug in me and leave it for 1minute.

As we all know France went out in semis, so we agreed before the final I’d pay up then we’d chill and watch the match.

I’ve never done ass stuff, and it freaks me out a bit, and they’ve known this for a while.

I stripped off, and made sure I was clean and smooth etc as per instruction.
They put it in slowly, it felt enormous and I couldn’t catch my breath as it was going in at first. It went in though. They laughed and I kind of laughed too, it was embarrassing and I got a bit hard. A lot of jokes were made at my expense.

After the minute timer went off they said I could take it out, but I legit felt weird and the sensation I didn’t feel able to (I know it sounds dumb).

They joked a lot about how I secretly liked it, and it started feeling humiliating. Eventually they said they’d help, but they got me to bend over instead of lay down this time.

And they kept pulling it a bit then letting it go back in, and it was for a while they kept saying how you have to be gentle but I’ve watched enough porn that people normally take them straight out?

I went rock hard and they gave me a lot of banter for that too. Eventually they took it out.

Posted Aug 4, 2026, 8:59 AM UTC

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