Hannah's Anal Curiosity

"They came to our suite?" Hannah asked, pretending she didn't already know.

"I'm sorry. I wanted to surprise you, in case you had second thoughts, but you weren't around."

"Luckily I spent the night roaming the beach and missed it. Threesomes aren't my thing. I'm a one-on-one kind of girl."

"That's too bad," Stephanie grinned. "It was quite an experience."

"Are you seriously telling me you had a threesome with those guys, in your room?" Hannah asked, pretending to be surprised.

Stephanie nodded. "I did. And it was the best set of orgasms I've ever had."

"Set?"

"I had a few powerful orgasms. By the time they were finished with me, I could barely walk, or even speak. It was that good."

"Sounds like I missed a good time," Hannah jokingly replied.

"It's not too late. Those guys are still around, and I have their number. Please, why don't you try it? I'm not going to judge you, if that's what you're afraid of. I'm never going to tell anyone. It'll be our secret."

"Thanks again for the offer. But no. Two guys at once isn't my thing."

"Fair enough," Stephanie nodded. "Threesomes aren't for everyone. I don't mean to sound crude, but not every woman was built to take a pounding from two endowed men."

"Endowed huh? I'm surprised you can even walk straight with what your vagina went through last night."

"Who said anything about vaginal sex?" Stephanie asked with an eyebrow raised.

Hannah was suddenly taken aback. "You had anal sex with those two guys?"

"And I loved every minute of it," Stephanie replied without shame. "The key is to use plenty of lubrication. Works like a charm."

Hannah's mind suddenly raced with images of Stephanie being ravished from behind, anally. It was a rousing thought, and Hannah tried not to let her imagination get carried away in the moment.

"Oh, that's interesting."

"What's the matter? You seem a little surprised."

"Can you blame me?" Hannah asked. "The thought of you doing, you know, that, with two guys is a little jarring."

"The thought of me doing what? Taking two big ones in my ass?" Stephanie asked teasingly.

"Basically. Yes," Hannah nodded.

"So you're fine with me having a threesome, but the anal part makes you uncomfortable?"

Hannah paused for a moment. "This conversation is really headed down the gutter."

"Was that a pun for my anus?" Stephanie smiled.

"Very funny. I think we should change the subject now."

"Why does the talk of anal sex make you seem so uneasy?"

"I'm not uncomfortable," Hannah replied. "I just think it's a little unorthodox, sexually speaking. Maybe I'm old fashioned, but I believe that sex should be a certain way in order for it to be special."

"Look, here's my philosophy on that: Sex is intercourse between two people right? So does it matter which hole is being used, as long as there's sexual pleasure involved for both people? The means to achieve a great orgasm don't really matter to me, as long as it feels great."

"So you've achieved orgasms through anal sex?"

Stephanie nodded. "Powerful orgasms if there's enough lube and preparation to make it comfortable."

"Oh..."

Stephanie's eyes squinted. "This is your fantasy, isn't it?"

"What makes you say that?"

"You seem so repulsed by it, yet you're also very curious. You have that look in your eyes, as if you're intrigued by it. Don't be shy about it, a lot of women are curious about anal sex."

"It's sort of a fantasy," Hannah admitted. "I've read articles about pleasure spots associated with anal sex, but I don't have any good experiences with it."

"What's stopping you? Anal sex isn't exactly a team sport. All you need is some lubrication, and a small sex toy which you can order online."

"I've tried it with my finger. It was way too awkward to be enjoyable."

"None of your previous partners have ever asked for it?" Stephanie inquired. "Your ex-husband was never curious about it?"

"Oh, he definitely was curious. I've had former boyfriends who've also wanted anal sex from me."

"What was the problem?"

"I tried it a few times in college, and each time was a disaster," Hannah replied. "It hurt really bad. I guess I'm just small down there."

"The rectum is supposed to be small. Did you try it with your ex husband at least?"

Hannah shook her head. "I'm a lifelong feminist. I've always felt that a strong relationship should be based on equality. If I let my husband stick his penis inside of my anus, that's an incredible submissive position for a woman to be in. I don't want to give up that kind of power in a committed relationship."

"Well if that's not old fashioned, then I don't know what is," Stephanie quipped.

"I know. But that's how I was raised."

"I've got an idea. Why don't you let one of the men I slept with last night take your anal virginity? I'll arrange for a private meeting. He's a total pro when it comes to anal sex. You would barely feel a sting. I promise."

Hannah shook her head. "I don't think that's for me."

"Why not? You promised to keep an open mind and have fun while we're here."

"I know. But I've never been comfortable with casual sex. I'm not judgmental with what people decide to do with their bodies. In fact I think sexual liberation is great. But personally, I need to feel a connection with someone before I can be intimate. If there's no connection, I can't get into the mood."

"Fair enough," Stephanie replied. "I completely respect that."

"So, now can we drop this subject and enjoy this beautiful ocean view instead?"

"If you insist."

The two friends leaned back in their lounge chairs while looking out at the view. The sun was coming up and it was another warm day by the beach.

***

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."