While I’ve had some great experiences,
My biggest missed opportunity was probably my Junior and Senior year of Highschool.
I didn’t have a car yet, and the bus actually took longer to get home than walking, so, that’s what I did.
On the street that intersected with mine, one of the elementary/middle school busses dropped off a couple kids right around the time I got there by walking.
The group consisted of 2 girls and one boy.
Over the course of these ‘path crossings’, light conversation would strike up.
The girls were clearly flirting, and one of them, a brunette was really cute!
Occasionally, she’d be there alone, or with the other *less cute girl.
They asked me several times to come play, but I turned them down each time, as I was a ‘highschool guy’.
The missed opportunities I’m referring to were on 2 separate occasions when the girls invited me to play truth or dare.
I have no idea why I turned them down (given my other experiences playing T or D).
I’ve often fantasized about what experiences I could have had with them.
I only lived a street away, and we ended up sledding together several times both before and after these T or D invites started.
Ugh!
If only I could have played T or D with them just once!
Just discovered my biggest missed opportunity
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NudeBaG
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- Jeepman89
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Re: Just discovered my biggest missed opportunity
It would be great to come up with a story of what could have happened with these 2 girls.
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justcantgetitup
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Re: Just discovered my biggest missed opportunity
During the school summer holidays when I was around 14 I had to walk to some shops about a mile away from my home to do an errand for my Mom. The block of shops abutted a long drive to a farmers field and as I was walking home I saw two teenage girls there, both bigger and older than me, a slim blonde and a slightly chubby brunette with large breasts. The brunette called out to me "Can I have your willie (penis) for my jar (vagina)?" I was a weedy kid who was often bullied so I got suspicious and fled. Almost certainly, I would have been stripped, hit and sent home naked and bleeding if I'd gone to them but sometimes wonder what delights would've awaited me if they had been on the level.
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