Freaky Fuckday

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The prep for anal was nearly as good as the real thing with the way Emily fucked his asshole using her fingers and rimmed his anus with her playful, agile tongue. The wantonness of Emily munching on his butthole never failed to make Chris tremble. She would pull on his cock until it hurt while her tongue penetrating inside his hole until Chris thought he had been driven mad. Chris's mistress made sure her bitch had an asshole that was wet, gaping, and begging for a good fuck before finally giving him what he needed by sticking her artificial cock inside him.

Chris was a true anal slut who could take the entirety of Emily's nine-inch shaft inside him. Emily sometimes liked to lay down perfectly still and watch Chris ride her strapon wildly and use it to fuck his own ass. She stared in awe at her anal slut as he slid his hole up and down all nine inches of her cock to swallow the entire shaft inside his rectum before shitting it out.

While Chris liked Emily fucking him in the ass like normal, he found the more fulfilling experience was getting fucked while he was dressed as a woman. Emily happened to love the sight of Chris's hairless, feminine body writhing as she penetrated him deeply. She couldn't get enough of the sight of Chris's shaved, erect penis flopping around while Emily pushed her strapon in and out of the hole adjacent to his cock. Emily demeaned Chris even more by calling his asshole her tight, little pussy and telling him she was claiming his hole as her own personal property. If Chris was really good while Emily fucked him (and he always was) she would offer to play with his 'clitty' until he came.

Emily creamed herself every time when Chris made himself her bitch and sometimes Chris ejaculated while being fucked without his penis even being stimulated. They still engaged in so-called 'vanilla' sex of course. But they enjoyed changing things up constantly and found that they achieved the strongest orgasms when they roleplayed as lovers with swapped genders. Chris still couldn't believe the same shy, demure girl who could barely look him in the eye when they first met was now spanking him and calling him dirty names while buttfucking him mercilessly.

Chris would never have believed Emily might be willing but eventually she overcame her reservations and allowed Chris to perform anal sex upon her as well. Lots of lubricant and preparation with fingers and tongue were required first but eventually Emily relaxed enough to allow most of Chris's penis to penetrate her anus. She couldn't take a cock up her ass the way Chris could though. She didn't have that kind of talent. But while being fucked in the ass was painful, Emily knew that if Chris could do it she could certainly take it.

Emily suffered for a bit while her ass became acclimated to the foreign object penetrating it, but eventually Chris's cock moving in and out of her rectum started to feel good instead of hurting and Emily pushed back against each of Chris's thrusts. Emily gave her husband the great privilege of finishing inside her rectum while her asshole clenched tightly around the base of his shaft. Emily felt weirdly proud of herself for taking all of Chris's cock inside her.

With the aid of Chris's fingers stroking her clitoris, the pulsing and pumping motions made by Chris's penis when he ejaculated stimulated Emily's anus so that she climaxed from having anal sex. She told Chris afterward that she only liked anal okay, but to be honest she rather enjoyed Chris's hot, sticky semen spurting inside her ass the same time rivulets of her own ejaculate leaked profusely from her slit.

Emily shocked Chris when she took his cock out of her ass, turned around, and went straight from having Chris's penis in her rectum to taking it in her mouth. Emily cleaned the flavor of her own ass off Chris's cock using her tongue and sucked him off until he came again. The whole time, Chris screamed Emily's name and declarations of his love for her. He had never seen Emily do anything this absolutely filthy and after Chris quickly finished in her mouth Emily just grinned at him and showed off the sperm resting on her tongue before swallowing his seed. Chris wasn't the only one who could act a total slut for their spouse.

Anal sex wasn't an act that Chris performed upon Emily often; he would much rather be on the receiving end of any anal experience if he had the choice. But it was nice to know that anal sex was actually an option when they both felt in the mood for something different. A few months ago, Chris never could have dreamed any of this would be possible.

Emily and Chris never told anyone else about the Experience. It was their own private secret that they wouldn't share with even their closest friends or family. Who would believe them, anyway? Chris and Emily sometimes wondered whether they were the only ones or if others had experienced the same phenomenon. How would you even broach that subject even if you did suspect it? All the happily married couple really knew was that the sharing of each other's minds and bodies in the most intimate fashion had saved their love lives, their sex lives, and their marriage.

While Chris and Emily had been together for nearly a decade and had made a home and life together, this was the first time in their long relationship that they felt like true partners. The Jennings knew each other and their bodies better than any other married couple ever could and they utilized this knowledge not only to deliver the most explosive orgasms to each other but also to understand and empathise perfectly with the other. They had become one body, one heart, one soul, and one love.

In about a year the Telegraph District project would be complete after the district had been completely refurbished. Emily would have far more free time once the project concluded and both she and her husband believed they would be ready then to take the next step in their relationship to conceive a child. They planned to attempt the feat of procreation several dozen times to ensure their efforts were successful.

When they were alone, Emily and Chris referred to each other with nicknames they derived following the Experience. No one else could possibly understand the layers and meanings of these references to each other. Before they fell asleep, totally satisfied after making each other orgasm multiple times and relatively sure in their assumption that they would wake in their normal bodies the next morning, Chris and Emily would kiss deeply and speak soft sentiments to each other.

"Good night, my husband," Chris would say with a little smile before he nodded off.

"Good night to you too, my wife," Emily would smile and whisper back before falling asleep in her true love's arms.

The End

*****

Thank you for taking the time to read my story! I hope you enjoyed reading it as much as I enjoyed writing it. Please provide feedback by commenting below or contacting directly by PM or email. Thanks again!

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AnonymousAnonymous7 months ago

Different and very good.

Things I liked:

1) Very well-written.

2) Fairly believable characters with realistic interactions and lives despite being fantasy.

3) Emily is NOT the standard and BORING Literotica porn stereotype female. She's not some super fit over 5'10 Amazonian with gravity-defying breasts and a stripper wardrobe who, of course, "doesn't look her age." I appreciate Emily being an "average" woman. It's refreshing and sexy. Wish more authors did the same, but most would rather write slutty porn bimbos.

4) Hot sex scenes.

What I didn't like:

1) Chris being so effeminate. How does he know how to select a coordinated outfit, style "his" hair, apply makeup, and pull-on pantyhose without any instruction? (Plus, the author seems confused what "pantyhose" are.) And when he comes home: he keeps on this super-femme outfit, puts on an apron, and starts cooking. Did June Cleaver swap into Emily? As the story progressed, Chris became gayer and gayer and gayer.

2) It would have been fun to see Emily enjoying a bit of Freudian excitement at "holding the power" and taking advantage. And Chris being more reluctant at engaging in all things "cock" in bed. Chris quickly tossing aside the prejudices/instincts of a life of heterosexuality was eyerolling. Emily doing a bit of coaxing to get Chris to let himself go would have been hotter.

3) Along the same vein, Emily instructing/ordering Chris on feminine things would have worked better than Chris instantly being able to do those competently on his own. For example, if Emily's meeting was so important then why didn't she tell him what she wanted worn rather than gambling on him picking something appropriate? That would have been hotter too.

Overall, a good and unique story that I enjoyed, but, as often with stories that I enjoy, did see room for improvement.

SinnerseekerSinnerseekerover 3 years ago
Different but great

Very good read. Must be one of the most unique stories . Thanks for sharing !

AnonymousAnonymousover 5 years ago
It really was a 6 star story!

I really wanted to give it the full five stars (because there is no way to give a higher rating) but a malfunction prevented that and what I imagine is a normal function of the page prevented me from upgrading the score. It was a wonderful story and one of the best and most engaging stories I’ve ever come across in Literotica.

AnonymousAnonymousover 6 years ago
Different... but highly enjoyable

A long but highly entertaining read. I wish my wife would read stuff like this (I don't think she's even heard of Literotica at all).

AnonymousAnonymousover 6 years ago
Loved the story.

The amount of detail was amazing and I loved the long build up. It felt very genuine and reminded me of why I like stories so much more. This is definitely my favorite story.

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