Hannah's Anal Curiosity

"Fine," Hannah replied.

Stephanie smiled, "Great. I'll be right back. Don't move a muscle."

Hannah waited awkwardly in the living room. She had no clue what to expect.

A minute later, Stephanie came back to the living room holding the small shopping bag, with her bikini bottom removed. She was completely naked from the waist down. Her legs were tanned, but there was a bikini tan line around her crotch, which showed how white her skin was naturally. She was completely hairless as well.

"What's the matter?" Stephanie said, modeling her lower half. "You've never seen a woman's pussy before?"

Hannah looked down at the vagina. "Not yours. At least not like that. Did you shave it recently? It's so... hairless."

"I shaved it this morning. Now let's get down to business."

Stephanie walked to the center of the living room, bare bottomed, and put the small bag on the couch. She then put her knees on the couch, with her ass pointing outwards, and she leaned her body against the couch. Stephanie reached back with both hands and spread her ass cheeks apart.

"What should I do?" Hannah asked, unsure of herself.

"There's lube in the bag. Start with that. Put a nice big load on your finger and slip it inside of me."

Hannah searched inside the bag and found a small tube of lubrication. She opened the cap and squeezed a large amount of lube onto the tip of her finger, then she turned her attention towards her friend's anus. It was her first time looking at a person's anus up close. It was small and pinkish-brown. The hole looked tight, and Hannah wondered how anal sex was even possible.

She slowly and reluctantly pressed the tip of her lubricated finger against the entrance of her friend's anus. Nerves got the better of her, and her finger was almost shaking. Once she touched the delicate anus, she pushed her finger inside, and coated the anus with lubrication.

"Does it hurt?" Hannah asked, with her finger in her friend's butt.

"It feels fine. You have a soft touch."

Hannah's arousal grew as her finger was inside of her best friend's tight and warm anus. Feeling the tightness grip her little finger gave her a sexual rush. She pushed her finger all the way in, while imagining Stephanie being ravished by two other men. She wondered how Stephanie's rectum could handle two endowed men. She also marveled at her friend's naked backside and vagina.

"Okay," Hannah said. "I think you're fully lubricated now."

Stephanie turned her head to look at Hannah. "Good. Now take your finger out and slowly insert one of the toys."

"Which one?"

"Any. I can handle all of those."

Hannah pulled her wet finger away, and watched the small anus immediately close. She looked inside the bag and searched through the various sex toys, which had already been removed from their containers. A medium sized pink dildo caught her attention, and she took it out of the bag and looked at it further.

"I hope you like pink," Hannah said.

"Nice choice," Stephanie smiled.

"Let me know if it hurts."

"Absolutely."

Stephanie assumed the position once again, and she spread both of her ass cheeks apart with her hands. Hannah got down on her knees and stared deep inside of her friend's lubricated brown anus. Then she aimed the tip of the sex toy towards the small hole and pressed.

Hannah slowly but surely pushed the small pink toy inside of the tight anus. She watched in complete awe as the anus stretched to accommodate the foreign object. The sight peaked her curiosity. Seeing Stephanie's anus and vagina up close made her unusually aroused. She blushed watching the sex toy go inside of the rectum. Hannah watched carefully, as if the whole thing was a medical marvel. It was a side of human biology that she had never seen before. Before long, the sex toy was inside of Stephanie's rectum, with only the bottom handle sticking out.

"It's inside," Hannah said. "Does it hurt?"

"Does it look painful?" Stephanie replied, wiggling her hips.

"Of course it looks painful. There's an object sticking out of your rectum."

"It doesn't hurt. Watch, try pulling it out, and slowly stick it back in."

Hannah slowly pulled the sex toy back, which slid out easily because of the amount of lube. When she pushed it back in, the tight anus offered some resistance, and Stephanie gasped while holding to keep her body in place.

"Sorry," Hannah apologized. "I didn't mean to push that hard."

"It's okay. You're new to this. You can make it up to me by giving it a little kiss."

"You can't be serious."

Stephanie briefly turned to Hannah. "What's the matter? Afraid of kissing a woman's backside?"

"Why not?"

Hannah looked her best friend in the eyes, and leaned forward to kiss Stephanie's butt cheek. She planted several more kisses on the soft skin, while continuing to work the sex toy in & out of Stephanie's body. The grip from the anus remained tight, but Hannah began to notice her friend's anus begin to relax, making the penetration smoother.

While using the sex toy, Hannah noticed that Stephanie's vagina became wetter by the moment. The pussy in front of Hannah's face was beginning to glisten with clear fluids coming out.

"Are you aroused?" Hannah asked.

"What makes you say that?" Stephanie replied suggestively.

"I can see your moisture."

"Why wouldn't I be moist? You're doing a great job."

Hannah's eyebrow raised. "You think so? This feels good to you?"

Stephanie reached back and pulled the sex toy out of her anus. She stood up and looked Hannah in the face while holding up the sex toy.

"You still don't get it, do you?" Stephanie asked.

"Apparently not."

"You'll never understand unless you feel it yourself," Stephanie replied. "I think it's time to put an end to your curiosity."

"I don't think I'm ready."

Stephanie took a step forward, so that they were face to face, while still holding up the lubed sex toy.

"Of course you're ready. You had no trouble using this thing on me. It's always polite to return the favor."

"I don't know," Hannah replied apprehensively.

"Of course you know."

Stephanie put the sex toy down on a nearby table counter. Then she got down on her knees and wrapped her fingers around Hannah's bikini bottom.

Hannah looked down helplessly as her best friend began to pull her bikini bottom down. She could have stopped it, but deep down, she didn't want to. Before long, her bare pussy was exposed in front of Stephanie's face, and she lifted each foot so that Stephanie could toss the bikini bottom aside.

"What next?" Hannah asked.

"Now, I want you to get on the couch with your butt sticking out. Nice pussy by the way."

"Thanks," Hannah blushed.

Hannah assumed the same position her friend did just a moment ago. She put her knees on the couch, and leaned her body against the backrest. At that moment, she realized how vulnerable she was with her anus and vagina completely exposed to Stephanie. She could hear Stephanie opening the lubrication, then closing it.

"You have such a beautiful backside," Stephanie said in admiration. "I'm serious, it's gorgeous. Now I'm going to put my finger inside. Are you ready for it?"

"As ready as I'll ever be."

"Good. Relax. I'll go slow."

Hannah closed her eyes and felt Stephanie's lubricated finger press against her anus. It was a soft touch. It was a gentle touch. Hannah felt the outer ring of her small delicate hole being stretched by her best friend's finger. She felt uncomfortable and embarrassed, but aroused. The finger probed her tiny anus like a medical exam. The lubrication was being coated around her rectal walls. Hannah could tell that Stephanie had done this many times before with a doctor-like precision.

The finger was removed, then Hannah heard the noises of the shopping bag ruffling. An object was removed, but she didn't know which, or how big it was. Hannah was too nervous to turn her head and look. She put all her faith in her Stephanie's judgement.

"Just relax," Stephanie said in a soothing voice. "Allow it to go inside of you. That'll make the process much easier."

Hannah tried her best to relax her anus just as she felt a solid object being pressed against it. She held on tight to stay in place, and the object was slowly being inserted inside of her ass. A small gasp escaped her lips as she was being penetrated. Her anus was being stretched in an unusual way. It was a strange feeling. The deeper it went, the more she felt her rectum being stretched.

"Are you okay?" Stephanie asked.

"I'm fine. Keep going."

"It's going to feel good in a moment. I promise."

The sex object continued its slow insertion, until it was all the way inside of Hannah's rectum. Her asshole was stretched and it took her a moment to mentally and physically adjust to the foreign feeling.

"It's not so bad," Hannah said, getting used to the feeling. "I'm comfortable with this."

Unexpectedly, Hannah felt Stephanie plant a big kiss on her butt cheek.

"Glad to hear it," Stephanie said with faint sense of exuberance.

The small sex object was slowly being worked in & out of Hannah's inexperienced asshole. The feeling was powerful to Hannah. She didn't expect the penetration to go so smoothly. She didn't think it was even possible. Moment by moment, she was slowly becoming accustomed to the sex toy sliding in her ass.

When her anus was becoming looser, the object was suddenly pulled out.

"Are we done?" Hannah asked.

"No. We're just getting started."

Hannah remained still and heard the noises of the bag shuffling once again. She already knew what to expect. She already knew what anal penetration felt like. What she didn't know was how big the next sex object would be. Knowing Stephanie, Hannah realized that her limits were about to be pushed.

Once again, the tip of another sex object was being pressed against the delicate ring of Hannah's brown anus. It was slowly pushed inside. Hannah instantly noticed that the new sex toy was much larger than the last. It was thicker and caused her anal & rectal passage to stretch even further than what she was comfortable with.

"Oh..." Hannah gasped.

"Do you need more lubrication?"

"Yes."

Stephanie paused for a moment and opened the lubrication while the object was still in Hannah's ass. She squeezed the lube onto the sex toy and continued to push the object inside of the anal passage.

The object continued its journey inside of Hannah's rectum, but this time, with more lubrication to make the experience even smoother. Hannah felt her rectum being stretched to its limits. It continued to enter even further than the last object did. The stretching feeling continued until the long object was inserted all the way inside of her ass.

"Here comes the fun part," Stephanie said, almost in a mischievous way.

The sex toy was slowly being worked with an in & out motion. The lubrication made the sliding easier. Hannah's anus and rectum were slowly adjusting to the penetration as the motion continued. The size of the object was becoming less of an issue as it continued.

To Hannah's surprise, she felt Stephanie begin to lick her left butt cheek. It was done for no other reason than for sexual pleasure. The licking continued. Then the lickings became kisses just as Hannah began to feel pleasure from the anal penetration. Stephanie moved her kisses down to Hannah's pussy, which sent a rippling shockwave throughout Hannah's body.

"What are you doing?" Hannah gasped. "Oh my god."

"Just relax."

Stephanie put her tongue inside Hannah's wet pussy, while continuing to work the sex toy in Hannah's ass. Hannah closed her eyes and leaned her face onto the couch. She was enjoying herself. The anal penetration still felt uncomfortable, and slightly painful, but it brought her a strong sense of sexual pleasure in an unexplainable way. Feeling Stephanie's tongue inside of her pussy coupled with the newfound anal sensation was a potent combination.

Hannah's body showed signs of sexual life. She swayed on the couch, while trying to keep her body still. Her toes wiggled. The muscles in her lower back tightened, and she squeezed the couch tightly with both of her hands. The facial expressions on her face were continuously changing. Her nose wiggled, and her eyelids were rapidly moving. Her lips tightened.

Feeling Stephanie's tongue lick up & down her pussy was sending Hannah over the edge in a way that she had never felt before. It was the first time a woman had ever pleasured her like that. Feeling the big sex toy sliding in & out of her asshole felt even better. Her breathing became louder. She gasped loudly. She didn't care how lewd or depraved she sounded or looked. All she cared about was the intense burning feelings inside of her pussy and asshole.

"Oh my god," Hannah moaned. "I think I'm....I think I'm going to...I think I'm going to..."

"Cum for me," Stephanie said, taking her tongue away from Hannah's pussy for a moment. "Don't be shy. Just cum."

Hannah once again felt Stephanie's tongue being inserted in her dripping wet pussy. The sex toy was rapidly being worked in her small asshole. Her back arched and she screamed. She came.

*

The orgasm was so intense that Hannah awoke lying on the couch. She saw Stephanie above her, caressing her hair. There was a big smile on Stephanie's face.

"That...was...incredible..." Hannah managed to speak.

The smile on Stephanie's face turned into a grin.

"I could tell."

"Did I faint?"

"I don't know. But it only lasted a few short seconds. You'll be fine."

"I'm glad we did this," Hannah said. "I feel like a new person."

"Good. I have a confession to make."

"What?"

Stephanie leaned down and whispered in Hannah's ear. "I knew you were watching me fuck those two guys. I heard you come in. I wanted you to watch. I wanted you to see me. I was a little upset that you didn't join us. But I'm glad things have worked out. This is what I've always wanted."

Epilogue:

Ten months later. Hannah come home from work to her beautiful new apartment. She was dressed in a sophisticated business suit. Things were busy in the office and it had been a long day. She took off her shoes and tossed her purse onto the counter.

When Hannah made her way down the hall, she saw Stephanie in their bedroom, undressing. Stephanie had also just arrived home from work.

"Busy day?" Stephanie asked.

"Can you tell?"

"You look exhausted."

Hannah smiled, "You can always tell how I'm doing. Things in the office have been hectic."

"Well, I just may have the cure for that."

"You're making me nervous. I don't like the sound of that."

"You will," Stephanie replied. "Look what I bought on the way home from work."

Stephanie reached inside of a small shopping bag and pulled out a strap-on. It was still in its container. It was long and thick. It was far bigger than anything that was ever inserted inside Hannah's body

"After a day like this, I can handle anything," Hannah sighed.

"Anything?"

"Yes, anything."

Stephanie grinned. "Good. Now remove your pants. Get on all fours, on the bed."

Hannah unbuckled her belt and removed her pants. Then she removed her panties and socks, getting completely naked from the waist down.

At the same time, Stephanie methodically removed her suit and was completely naked from head to toe. She put on the strap-on, grabbed a container of lubrication, and walked behind Hannah.

Stephanie whispered in Hannah's ear. "Relax. You're going to enjoy this. I promise."

The End

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