Hannah’s Anal Curiosity

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Ella Hollywood

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 lightning, 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. Ümraniye Escort “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, İstanbul Escort 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 sunglasses 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 breakups 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 Anadolu Yakası Escort 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 sightseeing. 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.”

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