I had my first gay experience when I was around nineteen years old. It was with a college friend of mine, who was about the same age. The encounter wasn’t much to speak of but I knew I wanted more.

Around the same time I was sneaking into my cousin’s room who was three years older than me. I could not help it but I had an uncontrollable need to wear her knickers. I used to get so hard my little cockette hurt! My cousin was so sexy, she had a perfect hourglass figure; the first time I saw her wearing a bikini I thought I wanted to be just like her.

Fast forward and I was in my mid-fifties. Call it a mid-life crisis but I was worried that if I did not have any fun soon that I would soon be too old to still perform well. Previously I did have a few gay encounters over the years and I’d carried on cross-dressing. My wife Kim was okay with my dressing but it really was not her thing. So I had tried a few online contact sites and had many brief exchanges but it was mostly all talk and going nowhere. That was until Rob answered and said he’d like to meet up.

I went to our agreed rendezvous, half expecting it to be a waste of time but happily, I heard a voice say, ‘Hi’ and there stood Rob. He was about 5’ 8, medium build, dark hair and was nice and polite. We were both very nervous but both determined to explore our fantasies and needs. A few days later I arrived at his lock-up garage with a bundle of lingerie carefully hidden. Rob was braver than me and got his hard cock out. Wow! I could see why he was so confident; his cock was lovely. I wasted no time getting down and worshipping it.

Oh! It was gorgeous, so hard, warm and veiny. It tasted so good. Just recalling that moment is getting me hard as I write this. His circumcised cock head and pre-cum tasted so good. I loved it. I stopped to get my breath and I asked if he still wanted me to dress up. Rob told me to be his slut and to quickly dress. I put on a black lacy g-string, a black padded bra, and a red suspender belt, and I rolled on my black nylon stockings. Rob wanted me then but I was not finished. I put on a black French maid outfit c/w white trim and a white apron.

“Ready when you are, big boy,” I called.

Rob was soon sucking my small uncircumcised cockette – ooh goodness, heaven! It was so horny and I loved it.

‘Oh god, Rob, fuck me please sir.’

Rob did not say a word, he pushed me over and roughly tried to fuck me. It hurt and I remembered I had brought some vaseline. So, I put some on my willing ass and some on Rob’s gorgeous cock and we tried again.

Oh god!

I loved it.

‘Fuck me’, ‘fuck my sissy ass.’

I was begging him. He fucked me slowly at first but as I started pushing back against his hard thrusts, he soon increased the pace. I loved it, I fucking loved it. He was stroking my stocking tops and somehow he managed to pinch my nipples too. He emptied his cock into me and I was his slut. I remember thinking at the time that I could take on a whole football team. I was so turned on and fuelled with lust.

We met a few more times whenever we could, until one day he said his wife was getting suspicious and it ended. I often walk by that old garage but I’ve not seen Rob since. I’ve had a couple of encounters in the last couple of years but sadly not quite as good as those days with Rob and his lovely cock.