Thanks for the feedback – here's the next part!
About four months after our motel tryst I was working a temp job and taking a short (25 minute) train trip to and from work. Waiting on the platform to go home one evening I saw my MILF sitting on a bench waiting for a train. I walked over, my cock hardening in my pants, and said hi. She lit up when she saw me, and I asked if she remembered me. She said, 'yes, the oral was incredible!'. We chatted and I got around to asking if she was interested in a round 2. She said she's think about it and email me. I was disappointed and figured she was letting me down gently. I went home and cranked one out before logging in. Don't miss those dial-up days!
She had emailed me saying she was interested, and we could go to her place the next Friday night. I was shocked and proceeded to be half hard for the rest of the week. In fact, I edged the rest of the week – 5 days – to build up a big load to paint her with.