A week had passed and the two mothers where again working combined shifts at the hospital, because of covid they were sleeping in a converted dormitory so Sam knew he had a whole week end with Simon alone. His mother was only too grateful that Sam volunteered to look after the boy, and also she'd noticed some changes in him lately, he was showering more and his room was cleaner and he washed up and laundered his own clothes. When she asked Simon about this he simply said it was Sam's idea so she nodded and approved of their friendship, and was glad the older man took a interest in the boy.
Man and boy had had their tea and washed up and we're relaxing watching TV, it was a pleasant July evening and the windows were open.
'I've bought you something Simon, it's upstairs on my bed.'
Simon looked at him wondering but quickly went upstairs and into the room. There on the bed carefully laid out was a blue 50's style full dress and attached petticoat plus underwear. With a sharp intake of breath he picked up the garments and held them to his cheek. The dress appeared to be satin and rustled when Simon held it to his cheek. Best of all a small bra with silicone falsies inside and a pair of satin panties.
Sam went to foot of the stairs and shouted up 'Shower first!' which startled Simon but he undressed quickly and dived into the shower, he spent a whole 12 minutes washing every where, hair, bottom and penis all got thoroughly washed and rinsed. Back in the bedroom he toweled off and stared at the garments, his heart was beating quicker and his hands where shaking but he was certain this was meant to be. He pulled up the panties tucking his small package inside and put the bra on all the while looking at himself in the full length mirror, next the dress and petticoat, he struggled with the zip but finally managed it.. He combed out his long hair and smoothed the clothes down and was startled to see how girl like he was, only 5' 3" and of slender build and although he was 19 he looked younger, indeed he looked better than most of the girls in his small friendship group.
'Hello Susan, you look lovely' and she nearly jumped out of her skin as she hadn't heard him come up, turning they flew into each other arms and embraced and kissed, Sam forcing his tongue into her mouth till she relaxed and played back and forth with him. He reached round and up under her dress and down the knickers till he found the little balloon knot of her anus and circled it with his index finger.
'Good girl, now across my lap please' and as though in a daze she did, he took the little tube and pulled down the panties to squirt a good measure up her anus and smeared some around the outer area. 'Now lie down' and she did and gazed into his eyes as she felt his hardness, quickly he rose took off his shorts and underpants and tee shirt and lay back down.
'Are you sure you want this Susan?'