One of my favourite rides in a S&M sort of way was when I was about 15. I left my house in Liverpool to ride to a place called Rivington Reservoir which was a trip of 60miles there and back. Being at school I had little money to spend in those days so I got £1 off my dad and set off. I got to Rivington and stopped in a cafe for a can of Coke and a Mars bar. When I left to go home I decided to extend my journey by taking in the climb of Winter Hill - about 2000ft - and looping around back onto my original route. It was the first time I'd climbed Winter Hill. I got to the top and started the decent, which was a very quick and very smooth road. After about 2 miles I came to a junction with a road which would let me get back home, but across the junction the road continued to descend so I followed it, thinking that I'd be able to find another road to get back to my route home.
After the descent I had another climb and then a descent into a valley. I headed up the valley aiming in the rough direction I needed to go, but no roads turned directly in the direction I needed so I continued riding up the valley. I ended up a town called Blackburn and ended up doing 100miles+ possibly even 120.
I didn't eat anything else due to lack of money from the 30mile point and I finally bonked about 10miles from home and took over an hour to cover the last 10 miles which was pretty flat. I was out for something like 12hours on that single pound.