Incest/Taboo Hannah's Anal Curiosity

Later that morning. The two friends walked alongside the beach boardwalk after breakfast. They looked at the different shops and stands. The more they walked, the more they headed towards the festive side of the boardwalk. It was the kinkier side of the boardwalk which was usually visited by a younger or free spirited crowd.

They saw assortments of skimpy party outfits on display in front of one of the stores.

"We should buy some of those as souvenirs," Stephanie joked.

"Sure. We can wear them to work when Halloween comes around," Hannah joked back.

"Come on. Let's have a look."

"Why not? I'm genuinely intrigued."

They walked inside of the small boardwalk store and browsed through the array of sexy outfits and skimpy beachwear. Some of the outfits were meant to expose naked body parts. The deeper they walked inside of the store, the more adult rated items were on display.

In the back of the small store, there was a collection of sex toys displayed on the wall. There were several types of different vibrators, dildos, and other toys meant to be used anally.

"You should buy one of these," Stephanie said, picking up one of the anal toys.

"Very funny," Hannah politely smiled.

"I'm completely serious. This could be your first proper introduction to anal. There are instructions on these things."

"I'd rather not. But help yourself."

Stephanie's phone made a noise, and she checked her phone. "Excuse me for a moment."

Stephanie stepped outside and texted on her phone, while Hannah continued to browse at the various sex toys. Some of the objects were so strange that she didn't know how they were supposed to be used. A few minutes later, Stephanie came back inside the store with her phone put away.

"Was it those two guys?" Hannah asked.

"How did you know?"

"You're blushing."

Stephanie shrugged. "Yeah, it was them. They wanted to meet up again because they're leaving tomorrow. I turned them down."

"Why?"

"Because the purpose of this trip is for us to hang out together. Besides, those orgasms I had last night are good enough to last me another week. I don't think I need to cum for a while."

Hannah flashed a playful look. "Thanks for the details. But don't let me hold you back from having a good time."

"I still feel bad for leaving you alone last night," Stephanie replied with sincerity.

"Please, I insist. I want you to have a great time while we're in Florida."

"Are you sure? Maybe we could double date. I hope you change your mind about that. It could be a lot of fun. You might like it."

"I'll tell you what," Hannah smiled. "You go ahead and see those two guys again, and I'd love to hear all of the juicy details about it."

Stephanie smiled back. "You're full of surprises."

"Why? I'm just a little curious, remember?"

"I know. But what makes you want to hear about my experiences?" Stephanie asked with an eyebrow raised.

"Let's just say that I'm content living vicariously through your unique sexual experiences. Is that a good enough answer?" Hannah playfully replied.

Stephanie nodded. "Good enough for me. I'm still trying to get you to explore yourself on this trip. One step at a time right?"

"Well, you never know."

It was a lonely evening for Hannah. After having an early dinner with her best friend, she was alone for the rest of the night. She walked along the shore. She listened to the local bands playing. She watched the festive activities. Finally, when she was tired, she went back to the suite and fantasized about her best friend. It was a harmless fantasy, she told herself.

Hannah rested on the sofa in the small living room area. She turned the tv on, and found her mind wandering to strange places. Deep down, she felt herself envying Stephanie for having the courage to push her sexual boundaries to new heights. Hannah ignored the television and closed her eyes. Her right hand moved downwards and she began to touch herself sexually. Her hand caressed her stomach before slipping down beneath her panties. She touched her sexual area and rubbed. A moan escaped her lips. It was the perfect escape from all the stress she had been dealing with in life.

Before she could get carried away, the door opened.

Hannah snapped back to reality and pulled her hand away. She sat up straight and pretended to watch tv as Stephanie entered caring a small shopping bag.

"You're early," Hannah said.

"I know."

"Did you have fun?" Hannah asked.

"I did."

Stephanie gave a coy smile as she closed the door, removed her flip flops, and sat down on the couch next to her best friend. She put the small shopping bag down on the floor.

"Well, are you going to tell me about it?" Hannah asked. "You're home earlier than I expected"

"That's because we got straight to business. We didn't waste any time. They have to wake up early tomorrow, and I didn't want to keep them up all night."

Hannah was taken aback. "Oh..."

"You're giving me that look again."

"What look?"

"The look which shows that you're curious, but you don't want to be obvious about it," Stephanie replied. "Come on, it's just me, we can talk openly here. You can ask me whatever you want."

Hannah thought for a moment. "Did you do anal again?"

Stephanie nodded. "With both of them. It didn't hurt that much. Like I told you before, they're experts at this. When it comes to backdoor sex, experience goes a long way."

"I'm sure it does."

"It's a shame that they're leaving tomorrow. I really regret not pushing you enough to meet them. I'm positive you would have loved the experience."

"And deny your chance at having a threesome with two men?" Hannah replied playfully.

"Good point," Stephanie blushed.

"Don't feel bad. I wouldn't have agreed no matter what. Casual sex isn't my thing. I've never been comfortable with strangers."

"Do you think you're ready to try anal sex?"

"Excuse me?"

"Are you ready for anal?" Stephanie asked again. "You've made it clear that you're refusing to hook up with anybody, but what about your anal fantasy? Are you ready to give it another try?"

"I don't know."

"You promised, remember?"

"I know I did," Hannah nodded. "But I'm not interested in doing anything with strangers, or those two new friends of yours."

Stephanie raised an eyebrow. "Who mentioned anything about strangers?"

With that said, Stephanie reached in the shopping bag and pulled out a small sex toy, which was still in its plastic wrapper.

"What the hell is that?" Hannah asked, startled.

"It's the sex toy we saw in the shop earlier today," Stephanie replied, almost with a sense of enthusiasm. "I can't let us leave Florida without you experiencing something new."

Hannah gave her friend a playfully stern look. "So do you expect me to just shove that thing up my butt?"

"No. I'll help you with it."

"I'll pretend I didn't just hear that."

"I'm being completely serious," Stephanie replied. "If you're not comfortable with a stranger, then why not me? I can help make it feel painless. In fact, it's going to feel wonderful. Trust me."

"I don't know. This isn't exactly something that friends should be doing with each other. It's not like we're in college anymore where it's okay to experiment with weird things. We're both adults, and there should be a line drawn somewhere."

"Says who?"

Hannah paused for a moment. "That's just the way it is."

"Stop living by other people's rules. We didn't come all the way to Florida so we could act like rigid old ladies. We came here to have fun, and to get away from our busy lives."

"True," Hannah conceded.

"I'm not going to pressure you to do anything. I'm only offering because it's your fantasy, and because I want this trip to be memorable. Just promise me you'll think about it?"

"Fine, I promise."

"Good," Stephanie nodded. "Now if you'll excuse me, I need a long shower."

"I bet you do."

"Trust me, I do. You should have seen how sweaty I was after those two strong guys pounded my ass for nearly an hour."

Hannah was taken aback by her friend's lewd comment. By the look on Stephanie's face, she was only teasing to get a reaction out of Hannah.

"Nearly an hour?" Hannah asked.

"Yep. Nearly an hour. I came multiple times. You really missed out on a riveting experience."

"You really did it for that long?" Hannah asked again. "Aren't you sore?"

Stephanie nodded. "Want to see it?"

At that moment, Hannah felt her heart rate rising. Her friend's anus wasn't something she expected to see, but when it was offered, it caught her interest.

"I'd rather not," Hannah replied in shy tone.

"Come on. I can tell you're curious."

Hannah thought for a moment. "Fine."

A sly grin appeared on Stephanie's face as she slowly stood, and turned around. Stephanie put her fingers up her skirt and slid her panties down to her ankles, taking them off. Stephanie bent over and lifted the back of her skirt, revealing her naked rear end. As if the sight wasn't explicit enough for Hannah, Stephanie used both hands to spread her ass cheeks apart, revealing her gaping asshole, with cum inside of it.

Hannah's jaw nearly dropped, and her eyes widened. The lewd sight was just a few feet away from her face, then Stephanie pulled her dressed down and ended the show.

"Get a good look?" Stephanie asked with a grin.

"I did."

"Good. I'm glad the showers here have movable handles. I really need to clean my bottom. See you tomorrow morning."

With that said, Stephanie walked to her bedroom, with her panties in hand. The small shopping bag was still on the floor. Hannah couldn't resist, and she took a peek inside the bag to see a variety of small sex toys meant for anal sex.

The next morning. Hannah and Stephanie went surfing for the very first time. An instructor guided them as they rode the mild waves. The experience didn't last long. The two moderately fit women crashed in the water several times, and soon found themselves completely exhausted.

They thanked the handsome instructor and gave him hugs for the good time. They laughed and collapsed onto their beach blanket, still in their bikinis, completely worn out from the strenuous morning.

"Let's see if we can walk back to the hotel later," Stephanie joked.

Both of them laid on their backs, spreading their arms and legs apart.

"I'd be lucky if I can even make it off the beach. My gosh, my legs are painful."

"I know."

"Thirty minutes on the elliptical machine doesn't compare to this," Hannah added, still breathing heavy. "I'm way too old for surfing."

"Oh, stop mentioning your age. You've got a nicer ass than most of these women in their 20's."

Hannah looked at her friend to see if she was serious. "Thanks I guess."

"You're always second guessing yourself," Stephanie replied, turning to look at her friend. "You should really stop doing that. You're an amazing person, and a beautiful woman. Act like it."

"Is that why you've been pushing me to explore new things all week?"

"I've had an epiphany a few years ago, about life. Since then, I made a vow to myself to live life to the fullest. That's why I've been traveling a lot lately. I wanted to see new things. I wanted to experience new things. I want to feel liberated."

Hannah gave her friend an understanding look. "I've always admired your courage and lust for life. That's really a great quality to have."

"Thanks," Stephanie nodded. "I've always been that way. I know it's not for everyone. That's why I'm not going to pester you anymore about doing certain things."

"I've been thinking about that."

"You have?" Stephanie asked with an eyebrow raised.

"You're right," Hannah replied. "You've been right all along, about a lot of things. You were right about this trip. Coming here was the best thing that I could have done. I haven't felt this happy in a very long time. And you're right, that I should explore new things. I should stop being so closed minded and enjoy life while I have the chance."

"Are you saying what I think you're saying?"

Hannah nodded. "As long as you're gentle with me."

"I hope your legs have already recovered. Let's go back to the hotel."

The two friends smiled at each other and struggled to make it to their feet. Standing was tough after their first time surfing. But they managed to fold their beach blanket and carry their things back to the hotel.

By the time they got back to their suite, their wet bodies had already dried from the hot weather. They happily dropped their things the moment they got inside of the room. Their legs were still exhausted from surfing. There was a nervous tension in the room, and Hannah gave her friend an awkward look. They were still in their bikinis while they stood awkwardly in the living room.

"I'm all yours," Hannah said, relinquishing control. "You can do whatever you want with me."

Stephanie smiled, "Oh really?"

"Yes, really. Within reason of course. Nothing crazy or weird. I don't want you getting any funny ideas. Just do what we talked about."

"I wasn't expecting this, frankly. I've never been an instructor for anal sex before."

"Experience makes all the difference," Hannah replied. "Just look at the surfing instructor we had. He had lots of experience teaching, so it was a lot of fun. So let's hope that this turns out well because we're dealing with my anus here."

Stephanie laughed. "Okay. Let's get right into it then. Take off your bottom."

"What?"

"You heard me. Take off your bottom. You want a commanding instructor? Then take off your bottom. Let's get straight to the point."

Hannah paused. "It's been a while since we've seen each other unclothed."

"Nervous?"

"Obviously."

"How about this," Stephanie said, making an offer. "I'll remove my bottom first. Then you can try this whole thing on me, so you can see how easy it is. Afterwards, I'll do it to you."

"You want me to play with your anus first?"

"Do you have a better idea? I think this is a great way to get you to relax, and to stop being so nervous."

"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
​