Not long ago Mike sheepishly confessed to me that he had been masturbating while wearing a pair of his Sister's panties. This intrigued me so I asked him to let me see what he did. Going to her bedroom he returned, looking slightly embarassed, wearing a pair of wide legged pink nylon knickers, tented out by his rigid prick. I smiled reassuringly and putting my arm round his waist started to gently stroke his raging hard-on through the soft silky material. As I did so he began to tremble and gasp and urge his prick up and down in my hand. Obviously the effect on him was dramatic because almost immediately he spurted copius amounts of spunk into the briefs. Over the next few weeks he continued to rifle his Sister's wardrobe adding to the garments he wore. In addition to always wearing nylon or silk knickers he added a bra, which he padded with rolled up stockings, a slip and more recently a dress or blouse and mini skirt. He tried to get me to dress up as well but lingerie doesn't turn me on. My part in this always involved masturbating him through the panties or sucking his cock as it poked out of the leg opening. He rewarded me by masturbating or sucking me to an orgasm but often said that he wished I had a special fetish or kink that would let him give me the same pleasure.
Several weeks passed before it was again safe for us to meet. On reaching his bedroom we stood close together gently massaging each others rising cocks. After a few minutes he said that he had a confession to make. I immediately thought he had met a girl and wanted to end our relationship. Anxiously I waited to hear what he had to say. "You know how much I like dressing in silk and nylon, well that is not what I like to do best." I immediately thought he was going to say that he wanted to fuck but before I could ask what it was he continued. "I will have to show you." As usual he started to undress and motioned for me to do the same. He then started to put on the undies. He liked an audience and sometimes needed help with buttons or zips. This time he surprised me by stopping when he had only put on his bra and pants. Thinking he had finished I went to take him in my arms but he evaded me and left the room. When he returned, I could hardly believe my eyes, my heart almost stopped beating with excitement. Over his arm, neatly folded, he was carrying what I immediately recognised as a womans mackintosh. Shyly he handed it to me and asked me to help him put it on. I took the garment from him and carefully shook out the folds of the gorgeous material. It was of scarlet crepe silk lined with the softest pale pink rubber. For a moment I held it against my naked body and, while he watched in amazement I buried my face in the smooth rubber lining, inhaling the delicious aroma. Mark walked slowly towards me and turned with his arms out ready for me to help him put it on. Reluctantly I held it so that he could slip his arms into the sleeves. He shuddered slightly as he felt the cold rubber slide up his bare arms, across his shoulders and down his back. I pressed myself closely against him with my straining prick pressed hard into the silky cloth, while I reached round his body and slowly, one by one, fastened the buttons up to his neck. Then I passed the end of the wide belt through the gilt buckle and pulled it tightly round his waist. Lastly I placed the hood over his curls with the rubber lining against his cheeks.