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Hannah’s Anal Curiosity

Category: Anal Sex, Lesbian Sex
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Hannah finished packing her things.

The divorce was nearly finalized. The split was mutual, with no hard feelings. The 36 year old corporate executive closed the last box and stood in the bedroom she had shared with her soon-to-be ex husband. It was a sad ending to her fairytale life.

One by one she carried the boxes away to her car. It wasn’t as painful as she expected. She just didn’t find the right person.

Self-doubt crept in her mind. She thought about how much time she spent focusing on her career rather than her love life. Her job had always been the focal point of her life. Hannah was always a hard worker with an overly ambitious attitude. Her dedication to her career is what helped her climb the corporate ladder so fast.

With all of her things packed, she drove away. She didn’t have a permanent place to live yet, so she was going to stay with Stephanie, her best friend since childhood.

Hannah’s Anal Curiosity

The water boiled. Stephanie poured the water in two separate cups and made hot chocolate. After she finished stirring, she added marshmallows and brought the drinks to the living room.

Hannah was looking through the window of the apartment during the rainy morning. She turned her attention towards her friend, who was holding the drinks.

“Thank you,” Hannah smiled, gladly accepting the hot chocolate.

“This should make you feel better, especially on a morning like this. I added extra marshmallows because I know how much you like them, even though they’ll ruin our diets”

Stephanie sat down on a nearby couch. Both women were dressed down wearing loose clothing and sweat pants, with their bare feet curled onto the couches.

“You always know how to cheer me up.”

“That’s what friends are for,” Stephanie replied.

Both women took sips of the hot drink.

“I’ve emailed my real estate agent this morning,” Hannah said. “We should be looking at some apartments soon. So hopefully I’ll be out of here in a month or so, depending on how fast everything gets done.”

Stephanie shook her head. “No, I don’t want to hear about that. I want you to take all the time you need to recover. For moments like these, you need someone to comfort you. Don’t spend so much time with your work and house hunting. It’ll only give you more stress.”

“Thanks. But I don’t want to bother you.”

“Bother me? Are you kidding? I love having you around. It makes me feel like we’re college roommates again.”

Hannah smiled, “You’re the best.”

There was a brief moment of silence as the two friends enjoyed their warm drinks and each others company. The rain outside began to pour heavily. A bright flash of lightening, followed by the sound of thunder was enough for them to turn their heads and look outside.

“That doesn’t sound very good,” Stephanie noted.

“I know. Perfect for the moment right?”

Hannah gave a faint smile at her own sarcastic quip, but there was a hint of sadness behind her eyes.

“It hurts me to see you like this,” Stephanie replied in a heartfelt manner. “I just wish there was something more that I could do.”

“Please, don’t feel bad. I really appreciate everything you’ve been doing for me. I couldn’t ask for a better friend than you.”

Another flash of lightning and another loud crashing sound of thunder grabbed their attention.

“Yikes. It’s getting nasty out there.”

“I brought a bunch of old dvds with me,” Hannah replied. “Maybe tonight we can watch a good movie and forget about everything, including this lousy weather. It’ll be like old times; a movie, ice cream, and our blankets.”

Stephanie’s eyes lit up. “You know, I actually have a much better idea.”

“I’m not sure if I like the sound of that,” Hannah said with squinted eyes.

“How much time-off are you taking from work?”

“About 2 weeks.”

“Perfect,” Stephanie grinned. “How do you feel about Florida this time of year?”

Hannah gave a faint laugh. “How do I feel about it? It should be hot over there.”

“Exactly. Why should we stay in this dark & gloomy weather for the rest of the week, when we can just go to Florida instead? I know the perfect beach resort for us. My treat.”

“But what about your job?” Hannah asked.

“I have plenty of vacation days which I haven’t used yet. Things are usually slow in my office this time of year, so it wouldn’t be such a big deal if I was gone for a while.”

“I don’t know. I appreciate the gesture, but I’ve got a lot on my mind.”

“That’s the point!” Stephanie replied with enthusiasm. “You’ve been going through so much stress with the divorce and your career. It’s time to focus on yourself.”

“It sounds like fun. But I don’t know. I might be a little too old for trips like these.”

“Nonsense. We still look great. I don’t want our lives to become boring and mundane while we’re single and in our primes. We’ve worked hard for our successful careers, so we should enjoy ourselves once and a while. We’ve earned it.”

Hannah paused before finally giving a reluctant smile. “Fine. I don’t know how you always convince me to do these crazy things, but you’ve done it again.”

“Deep down, I can tell that you’re interested,” Stephanie smiled back. “It’s not hard to convince you.”

“Maybe,” Hannah shrugged.

“We better go shopping tomorrow and buy some new outfits. I’m sure there’s going to be plenty of handsome young men chasing after you in Florida.”

“Oh please. Sex is the last thing on my mind.”

“Why?” Stephanie asked. “Your sex life has been stale the past few months hasn’t it?”

“Yes, but…”

“Then what’s the problem? Maybe getting laid is the solution to all the stressful emotions you’ve been experiencing lately. At our age, we’re at our sexual peak. Enjoy it while you can.”

“You’re probably right,” Hannah replied. “A good orgasm is always good for stress release.”

“And when was the last time you had a mind-blowing orgasm? I’m talking about the kind of orgasm that made your toes curl.”

“I can’t remember.”

Stephanie nodded. “That’s the point I’m making. You desperately need a romantic evening with a hot stud or two.”

“Did you just say two?”

“I did.”

Hannah chuckled. “I’m almost afraid to ask, but have you ever been with two men at the same time before?”

“It’s a fantasy,” Stephanie replied in a coy tone. “I’ve never done it, but it’s something I’ve often wondered about.”

“I wish I didn’t just hear that.”

“Well, you asked. I’m just being honest. You must have other fantasies that you haven’t told me about, don’t you?”

Hannah shrugged. “Everyone has quirky fantasies to some extent.”

“Anything you want to tell me about?” Stephanie asked with an eyebrow raised.

“Some things are better off as secrets.”

“Now I’m dying to know,” Stephanie smiled. “Maybe if we’re lucky, we’ll both have a chance to explore our different fantasies in Florida. It’ll be our secret.”

“Maybe,” Hannah smiled back.

“I’m serious. Why not make this trip a chance to explore the things we’ve never had the courage to do before. We’re not getting any younger.”

Hannah thought for a moment. “You’re right. We’re not getting any younger. It might be nice to try new things at our age. Who knows.”

“Do you promise to keep an open mind during our trip?” Stephanie asked, raising her eyebrow again.



The next day. The two women spent the afternoon shopping, looking for new clothes to wear on their trip. Hannah sifted through a rack filled with small bikinis. She picked one up and examined it, unsure of what to think.

“Is this what modern women wear in public?” Hannah asked in disbelief.

“Apparently so. You’re making us look old.”

“We’re not exactly young ladies anymore.”

Stephanie shrugged. “That’s what this trip is for, isn’t it? We can feel young again. One last time.”

“As long as I can find a bathing suit around here that’s appropriate for a woman my age,” Hannah replied.

“You need to stop worrying about age and what other people think. Have you been to a beach or a resort lately? Everyone dresses like this. Even women in their 40’s and 50’s wear bikinis like this without the fear of being judged.”

“I guess you’re right.”

Stephanie picked out a bikini and handed it to her best friend. “Try this on. I think this color would like nice on you.”

“It’s a little small, don’t you think?”

“Do you want to get laid or not?”

“Keep it down,” Hannah whispered, looking around the store to make sure that no one heard.

“Relax. No one is listening to us.”

“I still think this bikini is a little small for me.”

“Nonsense,” Stephanie replied. “It wouldn’t hurt to give it a try. Remember, the purpose of this trip is to have fun and to explore new things.”

Hannah took the bikini and looked at it. “Fine, I’ll try it on.”

The two women picked several more bikinis from the rack and went to the changing room. Each of them went in separate booths, and they tried on the small bikinis. After they finished changing, they opened their booths and looked at each other’s scantily clad bodies.

“Oh my,” Stephanie said, looking her friend up & down. “You look sexy in that little thing.”

“You think so?”

“Absolutely. You’ve got a great body. And the color suits you nicely.”

Hannah playfully struck a model pose in the small bikini. “Thank you.”

“How do I look?” Stephanie asked, adjusting her bikini. “I think this one might be a little too tight for me.”

“I think you’ll have an easy time finding two guys to have a threesome with you,” Hannah said playfully. “That fantasy of yours shouldn’t be hard to fulfill.”

Stephanie blushed. “Thanks. I’m glad to see you’re finally loosening up. You’ve been really up tight these past few days.”

“Yeah, well, I’ve been under a lot of stress. Being around you has always been therapeutic for me.”

“That’s what friends are for. Speaking of which, you mentioned my dirty little fantasy, but you’ve never mentioned yours. So are you going to tell me what it is?”

Hannah smiled. “Let’s just finish shopping. We still have a bunch of stuff to buy.”

“Okay. I understand if you don’t want to talk about it. But remember, you promised to keep an open mind during our trip, so I expect you to have fun,” Stephanie replied playfully.


Several days later. The two best friends were laying on their lounge chairs on a Florida beach resort. Both of their bodies were covered in ocean water from their recent swim in the ocean, but it quickly evaporated because of the heat. They both wore their sun glasses while they rested and looked up at the clear sky.

“You know something,” Hannah said casually, still relaxing. “When you’re right, you’re right.”

Stephanie gave an amused look. “What do you mean?”

“This trip. God, I haven’t felt so relaxed in a very long time.”

“Neither have I,” Stephanie agreed. “This is exactly what I needed. What we needed.”

Hannah breathed a sigh of relief. “I’ll never doubt you again. I’m in heaven right now. Seriously, you’re a genius.”

“Is that another promise?”

“What is?”

“You said you’ll never doubt me again,” Stephanie replied with an eyebrow raised. “Is that a promise?”

The two friends looked at each other playfully, while still laying back on their lounge chairs.

“Here we go again.”

“I’ve been right about everything so far, haven’t I?”

“Are you trying to get me laid again?” Hannah asked skeptically.

“I’m trying to get you to relax. It’s been painful watching you so depressed these past few weeks. It’s not healthy for either of us. I understand that you’re going through a difficult time in your life, but there comes a point where you have to move on.”

Hannah flashed another skeptical look. “And that includes sex?”

“Precisely,” Stephanie winked. “Maybe you haven’t noticed, but there are two handsome young studs who are checking us out. They definitely look interested in scoring with older women. I can tell.”

“Having a threesome is your fantasy right? Please, help yourself.”

“Only if both of us have a turn.”

Hannah laughed. “You can go over there and talk to them if you want. I’m too lazy to move. The only thing I’m interested in right now is my tan.”

“Suit yourself.”

With that said, both of them continued to lay back and enjoy the hot weather.


Later that night. The two best friends had dinner at a lively outdoor restaurant. It was a hot night, and they wore short dresses and sleeveless tops which bared their skin. Drinks were on the table, and things were casual. Live music was playing in the background and the atmosphere was festive.

“I haven’t seen you this happy in a long time,” Stephanie noted while they ate. “It’s nice to see. I mean it.”

Hannah raised her glass. “Maybe all I needed was a few of these.”

“Well said.”

They both raised their glasses and made a toast before taking a drink.

“I couldn’t have done this without you,” Hannah said in a heartfelt tone. “Seriously, you’re the best. The past year of my life had taken its toll on me. My work schedule was hectic, and my marriage was falling apart. When the inevitable divorce came, I felt like my life had completely crashed. It was awful.”

“Horrible break-ups are never fun. You’re a strong woman, you’ll get through it.”

“I think I already have, thanks to you.”

Stephanie smiled, “You’re too flattering tonight. Enough with the drinks.”

“It’s from the heart. I’m not drunk, I swear.”

“Neither am I. And right now, I know exactly what I want.”

“What do you mean?” Hannah asked.

Stephanie leaned forward. “Remember those two guys we saw at the beach earlier? Well, they’re over at the bar checking us out.”

“Oh god, not this again.”

“You promised to keep an open mind, remember? We didn’t come here just to lay on the beach and listen to live music. We came here to have a good time, and to forget about everything. We came here to have fun.”

“I don’t know Stephanie. I know that I promised, but I don’t think I’m ready to be intimate with another man yet. I’m sorry.”

“Don’t be sorry,” Stephanie replied in a comforting tone. “It’s okay. I don’t want to pressure you to do anything you aren’t comfortable with.”

“What about you? Are you comfortable with, you know, having a threesome with those guys? I mean, hypothetically speaking, if everything was safe, would you do it?”

Stephanie thought for a moment. “It’s been a fantasy of mine for the longest time, but honestly, I would be pretty nervous if it actually happened.”

“Why don’t you go for it?” Hannah asked. “You’re right, we’re here to have a great time. Don’t let me stop you from enjoying this vacation.”

“Are you serious?”

“Completely,” Hannah nodded. “I mean, I’m not exactly encouraging you to go over there and screw them. I’m saying that if you want to flirt with them or hang out, don’t let me hold you back. I’m perfectly fine with spending the evening alone.”

“You wouldn’t mind?”

“Not at all. There are plenty of things for me to do by myself. Now go over there and talk to them. They look like nice guys.”

Stephanie thought for a moment. “Alright. I’ll go over there and say hello. Wish me luck.”

With that said, Stephanie used the table napkin to wipe her mouth, and then she walked over to approach the two young men.

Hannah watched as her best friend introduced herself to the men. The music was loud, so Hannah couldn’t hear what they were saying, but she could see that they were getting along just fine. Within moments, Stephanie was laughing and flirting with the young men.

Minutes passed, and Stephanie eventually returned to the table with Hannah.

“How did it go?” Hannah asked curiously.

“I’m meeting them for more drinks. It was pretty clear that the three of us know exactly what’s going to happen later tonight.”

“Wow. I didn’t think you would actually go through with it. Are you really going to do it?”

Stephanie smiled and nodded. “Like I said, it’s a long time fantasy. I’m not getting any younger, and I want to have a good time while we’re in Florida.”

“Wow. You’re brave.”

“You know, they invited you. Why don’t you come? I don’t need to have a threesome with those guys. We can share. Or maybe we can take turns having threesomes with them?” Stephanie asked suggestively.

Hannah looked surprised by the offer. “No thanks.”

“Are you sure? I’d prefer if you joined us.”

“I’m positive.”

“What are you going to do for the rest of the night?” Stephanie asked.

“Don’t worry about that. There’s plenty of things to do around here.”

Stephanie winked. “Have fun.”

“You too. I know you will.”

The two friends hugged and went their separate ways for the evening. Stephanie went to the bathroom and checked her appearance, before meeting with the two men afterwards. Hannah walked along the shore and listened to the different live bands, spending the rest of the evening alone.


Midnight. Hannah dragged her feet up the short flight of stairs. She was exhausted from a night of walking and sight-seeing. As she approached the large suite she shared with Stephanie, she heard a faint noise. Hannah put her ear on the door and continued to hear faint noises. The noises were sporadic, and she couldn’t tell exactly what it was.

She unlocked the door and cautiously entered. The noises became unmistakable. It was the sound of a woman moaning in pleasure. It wasn’t just anybody. Hannah knew it was her best friend. Her first instinct was to leave immediately, but instead of walking out of the suite, she slowly and curiously approached Stephanie’s bedroom. The moaning sounds became louder.

Hannah peaked in the bedroom and saw Stephanie completely naked on the bed, on all fours, with two other men in the room. A man was pounding Stephanie mercilessly from behind. Stephanie’s small breasts swayed back and forth while she was being ravished. Stephanie’s body was covered in sweat, which showed that she had been going at it for a while. The other man positioned himself in front of Stephanie, and she performed oral sex on him, which muffled her moans.

The two men had been taking turns with each end of Stephanie’s body.

Hannah’s jaw dropped. She had seen her friend naked before, but never in a sexual manner. She was too stunned to immediately leave, even though she wanted to. For reasons unknown, Hannah found herself becoming incredibly aroused seeing her best friend having steamy hot sex.

When the men switched positions, Hannah quickly left so that she wouldn’t be caught. She left the suite and went outside to clear her head. She needed a deep breath and her heart was pounding. She also needed relief. After catching her breath in the warm night, Hannah went inside the lobby bathroom and masturbated while sitting on the toilet seat. For the first time in her life, she fantasized about her best friend.


The next morning. Hannah woke up early. She barely slept. She sat on a lounge chair on the outside balcony with a cup of coffee in her hand, overlooking the view of the beach. Watching the ocean waves was meditative to her. Footsteps walked behind her.

“Mind if I join?” Stephanie asked.

Hannah turned to see her friend with her own cup of coffee. Stephanie was wearing a large tshirt, and her hair was an utter mess. She looked like a woman fresh out bed after a night of rough sex.

“Sure. It’s a beautiful morning. The view is gorgeous.”

Stephanie sat down on the balcony. “It certainly is.”

“You’re in a particularly good mood this morning,” Hannah smiled, already knowing the answer.

“I had a fun night. What can I say?”

“Anything you want to talk about?”

Stephanie gave a playful shrug. “I really hit it off with those guys. We went out for more drinks and a night of dancing. It was so much fun. Afterwards, we agreed to have some adult fun. At that point I felt so bad for leaving you out. So I invited them to our suite, thinking you would already be there, but you weren’t.”

“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.”


“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 achieved orgasms through anal sex?”

Stephanie nodded. “Powerful orgasms if there’s enough lube and preparation to make it comfortable.”


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.”


“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 peoples 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 the 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.”


“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.”



“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.”


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 & 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?”


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.”


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.”


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 it’s 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.


“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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