Early Morning Dip
 

While on holidays in my parents place in Portugal. I always take an early morning swim in my speedos when its quiet. I can usually see a friendly neighbour of ours walking around his house and front garden in his speedos beside his family, watching me take a swim.
Once he sees me go for a swim, he goes back into the house and changes into board shorts before coming out and joining me as the only other person in the pool :(
He never takes those 10 extra steps into the pool in his speedos and always changes into board shorts before swimming. Plus I've never seen him swimming whenever I'm not in the pool in my speedos.

You may be plump SpeedoStocky but you can still be desirable and since you are staying at your parents holiday home you may be quite young. You enjoy swimming in your Speedos as you have every right to do, while he is happy to walk around his front garden some distance away from you. You are having an effect on him that he doesn't want you to see close to, so he covers up and wears something big and baggy. Be flattered but decide how you feel and what you want before suggesting he swims in his speedos with you as you may see a physical sign of his appreciation.

Thanks for your reply Torch. I'm not sure if I should suggest for him to wear his speedos too as then he knows I've been looking at him in his front garden. I may just continue to swim in the mornings and hope he gets the courage to wear his speedo to the pool

If you want to be a bit daring get a men's swim bikini with 1" sides or even a swim thong, something that you like the looks of and wear that. See if he "notices". If there's no one else around it's just between the two of you.

At the moment how do you interact when you are sharing the pool together, are you looking at each other above and below the surface or do you swim pretending the other isn't there.
When you finish do you sit or lie on the side of the pool for a while before leaving and get to chat to him ?

We normally just say hi as our paths cross when swimming and leave when we're done. But I might wait on the side of the line and chat to him when he's done.