Gurl, this isn't a LifeTime movie or Lindsay Lohan's Real Hollywood Story. Typically, kept boys live out their 30s and beyond in uneventful comfort. Remember, they were kept for their looks and personality. Dylan will still be an attractive, enough, guy in 10 years. His future probably includes another attractive partner with a normal job or a marriage to a wealthy man. Dylan will have connections that will land him a decent job in some creative marketing field, even without a degree. He might also follow the most popular path for former kept boys and become a real estate agent for the wealthy in NYC or LA.
If he starts taking hard drugs and selling that bussy on the streets then we might be closer to your predictions. But, it's the future so none of us know. I'm so entreated by his present escapades that I'd rather enjoy the ride.
The sugar daddy's POV.