I loved my job as a part-time pool maintenance man, or pool boy as everyone loves to call it. I just finished high school and enrolled in night classes at the local junior college, that don't start until September. Having night classes will allow me to work my part time job during the day. I loved going from beautiful house to beautiful house, cleaning and t...
Part 1 - The young man Barry was in his early fifties. He stood about 6ft-1, and weighed nearly 300 pounds. He had brown hair going to gray, and green eyes. In his youth, he'd been considered handsome. Barry was also very lonely. He was struggling to cope after the loss of his wife nearly five years ago. His wife of 25 years was a companion he sorely misse...
I was just horny. All of the time. I just wanted to fuck someone in the worst way. 18 years old, never had a date. Too skinny, too weird. I wore my hair long, not a very hairy body, not very athletic. Just a skinny kid who didn't get any attention. Lot of church girls in the bible belt but they weren't very interested in me. I guess. It didn't seem like anyo...
Please read A Crossdressers tale part 3 before moving on to this story. *** I slipped out of the sticky lubed up rubber, rinsed it and hung it on the rail to dry. Knowing full well I'll need it over the weekend. A quick shower and I jumped into our very large queen sized bed and began to nod off. Soon I was disturbed by someone squeezing in at the side of...
Dear Literotica Readers: Some random thoughts, in no particular order, about my story that don't seem to fit into my narrative but should help you know me better, which should help you understand the themes of my transition stories... Thank you to all of the people that have left me positive comments. I haven't been writing the stories for public approval;...
Chapter 05: Porn Star It was a beautiful sunny Sunday afternoon, so Jeannie put on a yellow string bikini and went outside to get a suntan. Jeannie used to suntan topless, but she'd recently discovered that men seem to really like tan-lines, so she was wearing a bikini top that had small triangles of fabric which really only provided enough coverage to hid...
My journey into the wonderful world of open and exhilarating sex started out very slowly. Like most men, I seem to be constantly aroused and ready. This unfortunately is not quite the same for all the women I know. My wife and I initially had some great and almost regular sex. Like most cases though, this started to wane and almost became non existent. The...
Chapter Three: Another Exciting Night as Sissy Slut Wannabe. Well about a week has gone by since I bought the dildo, wrist cuffs, ice lock and the lubricants at the adult sex shop. Dressing up as a sissy maid or a sissy slut everyday at home and learning how to use the dildo first with my mouth and trying out the flavoured lubes for added pleasure, but most...
Day One The rain was pouring down; the endless sheets caused deep puddles on the shoulder of the highway. I had already been driving for four hours and staring through the rain was really starting to bother my eyes. Up ahead in the road I saw a poor hitchhiker just soaked to the core, the way the rain was coming down it was hard to guess how long she had be...
It felt like I had flushed $199 down the toilet. For almost five months, I had been a paid member of an adult matchmaking site. Yet so far, I had only one meeting to show for it. When I divorced my wife six months ago, I promised myself that I would no longer suppress my bisexuality. Cocks of all shapes and sizes danced in my dreams those first few months...