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. I chose 'Guy fucks shemale'. There was a plethora of choices. I chose one, the tease pic showed a guy with a generous dong and a very attractive partner. As the vid played, they were obviously in a hotel room. The partner really looked like a woman, pretty makeup, big boobs, long blonde hair and, we soon see, was well hung.
Started out with her sucking on him to get him up. She did just an average job. No deepthroat, no sloppy spit drooling. Just an average blowjob intended only to get him hard. Then she got on hands and knees on the bed, and he started fucking her ass. Nothing spectacular but a bit odd to see her cock hanging down between her legs as he took advantage of her ass.
Then she lay on her back, legs high in the air, and started jacking off. Just slow strokes, massaging it. He was on the bed on his knees in position to fuck her ass again. First, he reached down and stroked her cock a bit, then had her tilt her hips up high and entered her puckered hole again. This time he was more animated and started stroking his cock in and out, going balls deep. All the while she was jacking herself off, her ample cock now hard. The guy noticed and pulled out of her ass and began giving her a blowjob. She was enjoying this and grabbed his head, thrusting her cock in and out of his mouth.
The scene then cuts to a role reversal. He's on his knees, laying across an ottoman. She starts by approaching his face, grabs his hair, pulls his head up into position and shoves her cock in his mouth, pumping it to get it hard again. Kind of kinky to see an attractive woman, big tits, long hair, nice makeup with a 9-inch dick fucking a guy’s mouth. Once she was erect, she straddles him from behind, forcefully spreads his legs and pushes her now hard cock into his hole. He cries out in pain, this only encouraging her.
She starts wildly pounding his ass showing no mercy. She keeps it up for a while as he continues to cry out from this painful ass fucking. Then she pulls out, strokes her cock a bit and shoots her wad on his butt, several squirts. For her finale she rubs her thick cum juice around and shoves her dick up his asshole again, pumping 6 or 8 more times.
Interesting, I thought. Odd to see a beautiful woman with a dick jacking herself off. And a woman, tits and all, fucking a guy in the ass. But being the kinky, horny bastard I am, I was OK with it. In fact, kinda turned me on.
I was still hard but still bored. Turned off the porn and lay back, closed my eyes, and started jacking off thinking about my missed opportunity with Trixie. She really was the cutest thing, sweet face, tiny bod, horny and craving sex. I remembered her giant clit, like a mini penis and her teeny tiny tight little cunt. I had so wanted to fuck it but passed, anticipating raunchy group sex later. Perish the thought - get back to Trixie's tiny cunt. I fantasized about visiting her RV, smoking a joint, getting drunk together. And having outrageous sex.
As the movie in my mind started, I was on the couch and Trixie was between my legs on her knees. She put my cock in her mouth and sucked it up hard. Then she showed off the skills that her old fart teacher had given her. She began absolute deepthroat, bobbing her head up and down, taking the whole cock in all the way. Up and down, up and down.
Then we were in her bed. We started out missionary, her body folded in half, her legs up by her head. She reached down to guide my dick into her pussy and as I pushed in, it wouldn't go. You sure that's not your ass baby? Nope. My cunt is really tight. Enjoy it. I pushed harder and, holy fuck! It was the tightest cunt I'd ever had. Wrapped my dick like a vice.
I was trying to pump it in and out, but it was SO TIGHT! Finally, it got naturally lubed up and slid in and out a bit more easily but shit! It felt so incredibly good and tight. I got to pounding it, but it never loosened up. She never got her slut cunt going. It just stayed wrapped tight around my cock the whole time.
All the while my eyes were closed as I was jacking off and fantasizing about this incredibly tiny pussy. Soon the feelings welled up and I shot a massive load, squirting 4 or 5 times. Wow. Sorry I missed actually fucking Trixie.
