Anal Pleasure – Chapter 1

My journey into the delights of anal sex began a decade ago. I fantasised about my then wife and I having a threesome with another woman. My wife just thought I wanted to fuck someone else. She couldn’t understand I wanted to see HER with another woman. I even bought a strapon dildo for her to use but she wasn’t interested at all. The toy got filed in a drawer. Sometime later we were making out on the bed when she said she had to go to the toilet. Several minutes later she came back naked wearing the strap-on. “Strip” she demanded. Then I got in the doggy position and had my first anal experience.

I am not embarrassed to say I enjoyed it. She did it once more. I loved being pegged. She was less impressed, mainly because I hadn’t discovered “flushing” so the result was, shall we say, rather messy. After the divorce a couple of years later I discovered a shemale website. I was fascinated by the sight of chicks with dicks. Some looking really attractive. Of course, being porn, these shemales had large cocks which also got my lust working in overdrive. Finally I decided to at least try it. So began my journey for real.

I had worked in Thailand and having returned home I was visiting twice a year to catch up with friends. I was in a place called Nana Plaza and noticed a bar with Ladyboys (Shemales). One looked very fetching. I won’t use names, I will call her “A”. I had done my research and learned about douching (I do it regularly now). Saved the mess experienced after my strap-on adventure.