Jessica's Anal Curiosity

She winked and nodded. "Okay. I believe you. Shall we get started now?"

"Sounds like a plan," he replied, extending his hand for her to hold. "Follow me."

Dave lead Jessica to his bedroom. Once there, her eyes surveyed the room. The bed was neatly arranged like before, with an open towel in the middle along with lubrication- nothing else.

"There aren't any sex toys on the bed," she asked with an eyebrow raised.

"Maybe we won't be needing them today."

Jessica smiled, knowing exactly what he meant. There was an obvious tension in the room, and she found herself becoming increasingly aroused.

"Is this because of that comment I made last night about wanting you to fuck me?" she asked playfully.

He playfully shrugged. "Maybe. Maybe not."

"That comment was during heat of the moment. I was masturbating remember? I don't think something like that should be taken very seriously."

"Well, I do remember that you were masturbating. But in my professional medical opinion, it sounded like you were serious. So I think I'm going to have to do something about that."

"Doctor's orders?" she asked, raising her eyebrow again.

"Yes, Jessica. Those are doctor's orders. But first, I'm going to need you to remove the dress."

A sudden rush came over her. She was very aroused, and her heart began to pound. Jessica lifted her yellow sun dress and pulled it over her head, tossing it to the floor. She wore a bra, but was naked from the waist down. She came to his apartment without any panties on, and he was admiring her almost nude figure.

"Will this suffice?" she asked teasingly.

"I'm afraid not. The bra must be removed as well."

She reached behind herself and unclasped her bra, tossing it to the floor. Her small perky breasts were exposed. They were upturned with pink nipples, which began to stiffen from sexual arousal.

"Looks like I'm naked," she said.

His eyes looked up and down. "If I had known you looked this good naked, I would have undressed you a long time ago."

"So what next?"

"I'll need you to assume the position on the bed. It's time for your exam."

She gave him a wink and climbed onto the bed on all fours. Once her body was above the towel, she rested her head on the blanket, and pointed her ass in the air. The sound of a bottle opening got her attention. Dave was opening the lubrication, and the anticipation was building.

Feeling his soft fingers against her anus sent a shiver down her spine. She could feel him apply a large amount of lubrication. He wasn't as gentle as before. After he coated the outside of her little hole, he pushed his fingers inside to coat her rectum.

"We're going to do something a little different today," he said, with his eyes on her ass. "So I need you to be more aroused than usual. Do you mind?"

"If that's what you think is best, go for it."

Without another word, Dave pressed his mouth against her vagina and began to lick. Jessica was caught off guard and wanted to shout, in a good way, but she held it in. It felt good. She loved the feeling of Dave's tongue running up and down her labia, and flickering around her clitoris. He licked as if he was waiting years to do it, and she appreciated the feeling. It had been a while since Jessica had a man pay that much attention to orally pleasing her.

Once he was done licking, he began to suck her little clitoris, and he sucked her labia inside of his mouth. His tongue went inside of her pussy and she groaned. All the while his hands rubbed & caressed her backside. He kneaded her ass like dough while he ate her pussy. When he decided she was aroused enough, he stopped.

Jessica's face was still on the blanket, and she couldn't see what was going on behind her. A part of her was disappointed when Dave stopped performing oral sex on her. But that feeling was replaced the moment he positioned himself behind her and pressed something against her anus. She knew immediately what it was. It was his cock.

Dave used his fingers to spread her anus and butt cheeks. Once her hole was spread, he used his fingers to guide his rock hard cock inside. The head of his penis entered, then he slowly pushed. He used his hands to hold on to Jessica's hips.

"Oww..." she gasped.

"Relax. The difficult part is almost over."

She felt him rub the lower end of her back as he continued to push his cock inside of her rectum. She had no idea how big his penis was since she had never seen it, so she didn't know how much further it would enter. It continued going down her rectal passage, and she felt herself being stretched by the hard cock.

Dave's hand returned to her hips and he pushed all the way in. His crotch touched her butt, and Jessica knew it was all the way in. He stopped for a moment. The delicate anus & rectum were given a chance to adjust to the foreign entry, and it was working. Every second that went by, the pain lessened, and she was becoming used to it.

"How do you feel?" he asked.

"Ready," she replied with her face on the bed.

The cock in her ass was still slightly painful, but she was comfortable enough to proceed.

Dave squeezed her hips tight and slowly pulled out, giving her a false sense of relief. The amount of lube helped his cock exit with ease, and once he was almost out, he slowly pushed it back in, filling her rectum once again.

"Ohh my..." she gasped.

Her asshole was beginning to loosen. Her sexual arousal was nearing its peak. She was ready to be fucked by him.

Jessica pressed her face harder onto the bed while Dave began to ravish her ass. She began to love the feeling of his hands squeezing her hips to hold her in place. She tried her best to keep her body still while he was slowly fucking her. His rhythm was slow, but his pace was increasing.

Before long, Jessica was getting her ass pounded and it was pleasurable. It was pleasure she had never felt before. Her moans became louder. The room became filled with sounds of her moans, the bed squeaking, the wet sound of a lubed cock going in and out of a small hole, and the rhythmic sound of his crotch slapping her ass.

"Oh god! David! Fuck me!" she yelled.

Her asshole was stretched and had adapted to having the large cock inside of her body. There was a powerful sexual sensation in her ass while Dave pounded her as hard as he could. It was intense, and unlike anything she had ever felt before. She was reaching her peak sexually and on the verge of a climax, which Dave was able to sense.

He reached down and rubbed her pussy furiously. Jessica screamed. She was being fucked anally and her pussy was being pleasured by Dave's fingers. The sensations were becoming too much to bear and she continued screaming from the intense sexual feelings.

"I'm cumming! Oh god!"

Fluids shot from her pussy and onto the prepared towel below her. It was as if being fucked in the ass opened the floodgates for her first squirt. She tried her hardest to maintain her composure while Dave continued pounding away at her tight asshole. She came hard. The fluids continued squirting onto the towel while Dave continued fucking her and playing with her pussy. Dave's fingers were dripping wet from her squirt.

The squirt eventually lost its power while he continued ravaging her asshole, but fluids were still dripping from her pussy like a leaky faucet.

It wasn't long until Dave began to grunt and moan. He fucked her even harder. Then he shot load after load of his own cum deep inside of her rectum. His cock continued plunging in-and-out of her ass. Each time his cock would pull out, there was more and more white stuff visible on his cock. His own cum was providing additional lubrication.

When it was all over, Dave collapsed on top of Jessica's naked backside. Their bodies were both flat on top of the bed. Their bodies were sweaty, and their sexual parts were covered in orgasmic fluids. They breathed heavily and stayed silent for a moment. His flaccid penis was still inside of her ass.

"That...was...unreal..." Jessica groaned from the bottom.

Dave kissed her face. "You were unbelievable."

"I think you finally got me to change my opinion on anal."

"So you liked it huh?" he asked, already knowing the answer.

Jessica turned around to lay on her back. Dave's cock was out of her asshole, flaccid, and dripping with cum and lubrication. He was still on top of her and they were face-to-face.

"Can't you tell?" she playfully replied.

For the first time, they kissed. Their lips pressed against each others, then again. Their tongues met and they shared a wet, sloppy kiss.

"I'm glad you liked it," he said in between kisses. "Because there are a few more tricks I'd like to share with you. I'm sure you'll enjoy them."

"Do they have anything to do with my ass?"

"What else? Your ass is made for pleasure."

Jessica smiled, "Now it is, thanks to you."

The End

Story by cutegirl3818 (Kelly)

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