Chapter 9:

Cheryl’s Not a Shemale

I called the next name on the list, Cheryl, to see about doing some additional cleaning on the boat. She sounded kind of distracted or distant on the phone, like she was preoccupied with something. Nonetheless, I arranged to pick her up at the dinghy dock in the morning.

I had the day to myself and just wanted to chill. Cooked some food, straightened up a bit, then felt that unmistakable tingle down below. Pulled out my tablet and fired up my favorite porn vids. Started watching my ‘go to’ deepthroat vids. Yeah, nice but I had watched them hundreds of times. So, I switched to my fav anal vids. Lots of good ones including one slut, on the floor on her hands and knees, with multiple guys power slamming her ass, one right after another. Just brutally ramming their cocks into her gaping asshole. But I’d seen this one too, multiple times. I was hard, slowly stroking my cock but nowhere near an orgasm. I wanted to explore something different.

Hit the search key and typed in … let’s see … uh … hmmm …. I know! I’ve always been strictly hetero (the mere thought of kissing another guy revolts me) yet always fantasized about either fucking a guy’s ass or having a guy fuck mine. I’ve used a dildo on my own asshole but always wondered what it would be like to have someone else fuck it. I typed in “shemale”.

The options seemed endless with every possible permutation represented.