He squeezed his eyes shut, as if, not seeing her would somehow ward off what he knew was coming, as she reached over to the nightstand and grabbed the...squeeze bottle of lube.“Ryan, listen to me, this will hurt a lot more if you try to fight it; just relax and soon the worst will be over.”When she saw his rosebud begin to open, she slowly forced her strap-on into him. Just an inch at first, then two, and then she backed off a bit, and then four; soon she had given him all she had. She almost. She was perfectly middle aged, rocking the mom jeans and a vee neck shirt that perfectly showed off her c cup cleavage.She had shoulder length blonde hair and the most piercing yet kind blue eyes that I have ever known. She didn’t look much different from when I had seen her last. The typical soccer mom physique. In shape, but on the cusp of letting it go. No eighteen year old, but tight and firm in all the right places.She babysat me often as a child and I was always in love with her. Once,. More

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