When I was eighteen I got thrown in jail for sixty days for hitchhiking in Colorado with a very small quantity of pot in my possession.
I was so intimidated being slight, white and quite the prettyboy. There was two others sentenced to the county jail, their crimes much more serious.
We stood before the jailors the other two in briefs and boxers, me in cute tight white bikini underpants. They all were checking out my smoothly fresh boyishly cute body, I felt horrible.
He said loudly"Drop Um, bend over!" Watching the two drop their underwear,bend over, I reluctantly did the same. I was the first, with a gloved finger well lubed I squeaked in pain as he pushed it in fingering all around looking for contraband he enjoyed that I was so tight, saying so repeatedly. I was so embarrassed, mainly because I uncontrollably got an errection and everyone noticed.
Yes, I became the cutest boybitch in the county jail for those sixty days. None of it was brutal r**e, I was made love to and what was kinda forceful in the beginning became conscentual. I was kissed and petted like a girl and kinda liked it.
Two weeks before I was released, because I was a short timer I was given outside details and had to submit to a digital exam daily upon return.
The jailor noticed the difference right away. "I knew that cute twinkie ass of yours was gonna make everyone happy!" He said as he worked my boy'sass with multiple fingers. It got me excited, I couldn't help it, I'd been conditioned.
That's when it happened my first BBC, the jailors. I moaned "It's too big, please don't!" "you'll be fine sweetie, so fine." As he slowly worked it all the way in I realized that my boypussy was his for my last two weeks. It felt like the first time all over again!
I'm back with my girlfriend,
now my wife, different now for sure. I'm a pantyboy and still like an occasional fucking, still have a body like a high school freshman that attracts all it can handle.