desembolsillar

A colloquial regionalism, mainly heard in the Caribbean and parts of South America (Cuba, Puerto Rico, Colombia, Venezuela), meaning to take money out of one's pocket — often against one's will, or to make an unwelcome, forced payment.

• Tuve que desembolsillar para pagar la multa. — I had to shell out money to pay the fine.
• No quería desembolsillar tanto por ese arreglo. — He didn't want to fork out that much for that repair.
• Nos hicieron desembolsillar antes de dejarnos entrar. — They made us pay up before letting us in.

This is a regional colloquialism, not standard across the Spanish-speaking world — a learner outside those specific countries is more likely to hear pagar or the more general desembolsar instead.