What are the chances? I hadn’t seen Diana for over 40 years. We went to school together through our primary and intermediate years but the town we lived in only had single sex colleges and I only went there for a year anyway before we moved to another town.
I was overnighting in another city for work and had finished for the day and had gone back to my room, grabbed a shower and gone to the restaurant for dinner. I was sitting there looking at the menu when a lady walked in. She kind of looked familiar and she looked at me as if she was thinking the same thing. She sat at a table just opposite me and after a while I asked her have we met before. She said I was thinking the same thing and told me her name was Diana. That’s when it clicked. She ended up moving to my table and we had dinner together with an awful lot of catching up. We were both married with kids who had left home, she was working for a large retail chain and travelled quite a bit for her job. Ironically she had been to where I lived the week before and said she came most months for at least 2 days and a night.
We finished dinner and went to the hotel bar for a drink and carried on chatting. Diana admitted to me that she used to have a school girl crush on me, I said funny that, I had a crush on you for years. We both joked about it and said shame we hadn’t acted on it but we were both pretty young. We were getting a bit flirty by now truth be told. After a while I said I guess we should call it a night and she asked did I want to come back to her room. I was pretty sure what she had in mind so asked her what hubby would say and she said I’m not going to tell him and I’m sure you won’t. I replied definitely not and we headed for the lift. The lift door opened and I guided her in with my hand on her ass and the fact she didn’t flinch confirmed to me where this was headed.
As soon as the lift doors closed we were kissing and were hardly in her room and were naked on the bed. We pleasured each other, Diana came repeatedly from my fingers and tongue and when I finally entered her she was so wet and begging for my cock. We fucked in different positions and finally I came deep inside her fucking her from behind. Diana came again moments before I did. She lay down in the bed and I went back down on her eating her another orgasm.
We lay there cuddling and she admitted she had never cheated on her husband before but wasn’t feeling guilty at all. After a while we 69’d, I came in her mouth and she drenched me with her juices (and mine) cumming a couple of times. We drifted off to sleep before waking in the morning for a repeat of the night before.
Diana came to my town several times after that. She always arranged an early check in to her motel so we could spend a few hours together before she did some work. They were great times, finally getting to fuck my school boy crush even though it was 40 years late.