Written by Rob

18 Sep 2008

My neighbour, Brian is in his early 60’s, and a quiet, private chap. A few nights ago, while I was modelmaking in my shed, Brian called by to return some paintbrushes, and commented on a box with women’s clothes next to the bench. I mumbled something about a forthcoming ‘vicars & tarts’ party, and how my wife was buying clothes for me in the local charity shops. To diffuse the situation, I laughed that wearing high heels was difficult to master, especially in a tight skirt; with that, Brian wished me good luck and left.

Five minutes later, there was a knock at the door, it was Brian again; he was slightly nervous, and asked if he could try walking in heels, as he’d often wondered what it was like. He closed the door while I rummaged through the box, to find a pair of 3’’ heels that I thought would fit him. He sat down, removed his shoes and socks and put them on, while I joked that I’d tell his wife Judith, which made him blush as he stumbled about. To make him feel more comfortable, I found a pair for myself, removed my shoes to reveal black stockinged feet, and put on my heels; while doing this, I noticed that he was trying to cover his erection with his hands. I made a comment about it, and nervously admitted to him that I’d been wearing tights to keep myself warm in the shed on cold evenings for several years, and that I had an enormous erection the first time I tried on heels, and that I often masturbated in front of an old mirror in the corner. I suggested that if he wanted to ‘relieve’ himself, I’d go back into the house for 10 minutes, he thought that was a good idea. I gave him 20 minutes, and by the time I went back to the shed, he’d gone.

A few days passed, and one evening I was in my shed, when I heard a knock at the door, it was Brian. I invited him in, and over a cup of tea and a drop of whisky, we discussed the other evening, and how it turned him on. I suggested that if he ever wanted to ‘dress-up’ and have a wank in private, he was always welcome to use my shed. Actually, he said, he was wondering if I would be interested in dressing-up with him, and that we could masturbate in front of each other. Naturally, I agreed, and suggested that if he wanted to try mutual masturbation anytime, that was fine with me. As there was no time like the present, he asked me if I had those heels at hand as he wanted to try them on again; by the time I had found them, he had stripped off his shoes and trousers to reveal that he was wearing a pair of black tights, and sporting a fine erection, penned in by the tights. I wasted no time in taking off my trousers, underneath, I was wearing tan tights. Brian sat back on a chair and started to stroke himself, I lowered the waistband and took out my cock, slowly wanking it while watching my neighbour pleasuring himself. He took out his cock, pulled back his foreskin, and was slowly rubbing the pre-cum around the head. He stood up, and walked over, and we embraced, kissing each other passionately, out tongues entwined, our cocks rubbing against each other. He reached down to my cock and started wanking it, slowly at first, then building up until I spunked on his leg. I took him in my hand and returned the favour, all the while French kissing. He ejaculated up my stomch. We held each other for what seemed like ages, it was our first bi experience, and a moment to treasure.