The Day He Lost His Anal Cherry

Clarice's man, Jake, did not like anything to be near his asshole; he had a real phobia about it. Clarice had often told him of the fun she had when he stuck his finger up her ass, but she could not talk him into trying a little anal play himself.

He wanted to get over this fear. Jake had received some advice from a sex toy specialist and purchase a thin anal dildo and some lube. He got the package in the mail and decided the next day would be the day he would no longer be an anal virgin.

Clarice was in the shower. She loved marathon bathing sessions, so she was unlikely to get out of the water any time soon.

"Hi, Sweetie!" Jake purred as he stepped in the shower with her. He sat his sex toy and lube on the edge of the tub where Clarice couldn't see them.

"Have I told you lately how much I love and trust you?" he asked.

"Yes, as a matter of fact, every day."

"Well, I need you to help me with something," he reached behind and grabbed the dildo. When he presented the Anal Starter to Clarice, her eyes bugged open. "I want you to help me have fun with anal sex. You keep talking about how wonderful it is, and I love to watch you squirm with excitement every time I stick my finger up your ass. You have the best orgasms when I do that, so there must be something pleasurable about it. I don't want to be left out of the fun."

Clarice knew that the Anal Starter was perfect for Jake because it was small and slender. The sight of it didn't scare him into unconsciousness or cause his butt to pucker up defensively; as her previous attempts had done.

"So you finally came around," she said as she gave him a big hug. "I'll help you, and I'll be very gentle."

"I'll admit I'm very nervous."

"I understand that. Let's choose a safe word. If it's getting to be too much for you, just say "Kabuki". She took the dildo and the lube then nodded her head in approval. "Let's get started with the fingers first."

Clarice's hands reached out to Jake's ass. She knelt down in the shower, facing his crotch, his hard dick bobbing in her face. She massaged his tight ass muscles until they were loose and warm beneath her fingers.

She took the head of his dick into her mouth. She sucked only on his head, relishing the salty taste of his semen as some of it leaked into her mouth. His dick jumped as she sucked. She ran her right hand, covered with lube, along the crack of his ass.

"Is this okay?" she asked.

"Yes. Keep going. It feels good," he said.

Jake leaned forward, keeping his legs spread for easier access to his delicious ass. Her fingers, slick from lube, approached his asshole. She ran one finger just along the outside of it. Jake tightened briefly, but Clarice continued to run her finger around his puckered hole in slow, gentle circles, all the while sucking on his hard dick. She felt Jake's ass muscles relax. Once she knew Jake was completely comfortable, she slid the tip of her finger into his ass. He moaned and tightened up a little bit. She sucked on the head of his dick and slid her right index finger a little deeper into his ass.

"Oh, God, what have I been missing?" Jake moaned.

"You like it?" Clarice asked.

"Yes!" Jake said. "Keep going. But go slow."

She slid her finger into his ass about an inch. His muscles tightened around her finger. With his huge dick in her mouth, she slid her finger in and out of him. His dick grew harder the more she deeply she ventured.

"Don't stop," Jake moaned. "This feels wonderful."

Her slippery fingers pressed against his crack, and soon found his asshole. She inserted her index finger again, and felt the familiar tightening of his ass muscles. His dick grew even larger in her mouth, and she knew he was going to come soon.

She slid a second finger into his ass, and let his muscles close around her, getting used to the feeling. Clarice grabbed the lube, and squeezed a large amount of it onto the Anal Starter. When she felt that he was loose and lubricated enough, she slid the head of the dildo into his asshole, no more than half an inch.

"Is this okay?" Clarice asked.

"Oh, God!" Jake's ass tightened a bit. "Don't stop!"

She smiled. "I'll take that as a 'yes'."

She rubbed her slick fingers around his crack, and slid the Anal Starter in a little further and then slid it out, ever so slowly, not withdrawing completely. Each time she slid the dildo back in, she ventured a little deeper. He couldn't take the whole thing, and she wasn't going to push him to do so.

She sucked on his dick while she slid the dildo in and out gently. When she entered deeply, she rotated the toy in circles. It must have been the pressing against his prostate that made him shoot his cum in her mouth. She sucked down every last drop, not missing the slightest bit.

From that point on, at least once a week, Clarice and Jake enjoyed a little anal play in the shower. Jake was grateful that Clarice had taught him how much fun anal play could be.