Incest/Taboo Sally’s Wish, Anal Education

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Sally's Wish​

Sally updated her wish list at the very last minute. It was an annual thing her friends liked to do. Instead of having to buy everyone a bunch of gifts, each person would be secretly assigned to one person.

They were all career oriented adults, so the price limit was $300. Not too high. Not too low.

Her wish list was fairly basic. Even though she prided herself on being a sassy & sophisticated woman, she had most of what she wanted anyway.

So she picked a few travel essentials: crime novels, music, and travel wear.

Fairly cheap items. She expected a gift card to make up for the rest of the $300 limit.

When it was time to exchange gifts, Sally got everything she wanted at the little get-together between friends. Thriller novels. A few things to keep her warm. And she also got a gift card worth $250.

It was a gift card for a spa in Italy, where Sally was expected to travel soon as a travel writer.

"I look forward to it," Sally smiled at the party, holding up the gift card for everyone to see.

The anonymous friend was revealed to be Aileen, a married housewife who was friends with Sally since high school.

"I know you'll love it," Aileen smiled back.

The little gathering continued with everyone else opening their gifts.

A few days later. Sally packed her things at night. She had already attended another party with family. Now that the holiday season was nearly over with, Sally could concentrate on her job, which was to write about a new Italian adventure during the winter time.

Her phone rang. It was a call from Aileen, which kind of surprised Sally, because Aileen was a family woman. She always spent her nights with her husband and kids.

They made small talk for a while and Aileen sent her regards for the trip.

"You're actually going to use that gift card, right?" Aileen asked.

"Yeah, of course."

"I mean it Sally, I know how your apartment is. You get tons of gifts and presents and you toss them in a pile which will soon be forgotten."

Aileen was right. With a packed travel schedule like the one Sally had, her place was a mess and she had small items stacked everywhere. Most of the items were stuff she bought during her travels, or gifts from fans of hers.

"Do you really think I'll pass up a trip to the spa?" Sally replied.

"Good point."

"Especially during winter. This place better be good."

"Believe me, it is," Aileen replied. "Rick and I spent our honeymoon last year in Italy. We went to that very same spa."

Rick, of course, was Aileen's dear husband. And Sally detected a sentimental feeling in Aileen's voice.

"It must have been a nice honeymoon."

"Definitely. Let's just say it spiced up our love life, especially after, you know, having kids."

That caught Sally's attention. The typically prudish Aileen was never one to talk about her sex life.

"Sounds like one hell of a massage."

"It's more than that. They offer other services too, you know."

"Aileen, whatever you called me for, just say it. I know you better than you think. Just be frank."

There was a brief pause on the phone.

"Rick and I, you know, explored anal fantasies at that spa," Aileen said in a soft and shy tone.

It more than grabbed Sally's attention.

"Well aren't you full of surprises today," Sally replied.

"Actually, the surprise was meant for you. I didn't want to mention any of this in front of the others, for obvious reasons, but I know it's your fantasy too."

"Are you talking about that conversation from back in college?" Sally tried to scoff. "I appreciate the sentiment, but that was such a long time ago."

"So you're telling me that you don't think about it anymore?"

"I'm not saying that either."

"If I had the courage to try this, then so should you," Aileen said with a sudden newfound courage.

In a direct way, Aileen was right. Aileen had always been the quiet book smart girl of the group. Sally had always been the outgoing one.

Sally quickly looked around her bedroom and found the gift card next to her bed. She was planning to take it on the trip and use it. She looked at the gift card from a much different perspective now.

The spa wasn't simply a place for rest & relaxation. It was a place for sexual satisfaction. Anal satisfaction, to be exact.

"What is this place?" Sally asked, looking at the card.

"The one place in Italy which you shouldn't write about. It's a lovely little spa which offers secret services. Promise me you won't write about it?"

"Promise. I wouldn't want to ruin a good thing."

Aileen breathed an unnecessary sigh of relief. "Show them that gift card. Then mention my name. They know me."

"Really? Are you a regular there?"

"Long story," Aileen said, brushing off the question. "But they're professionals at what they do. Trust me. If they can get me into it, they can get anyone into it."

The absurdity of it all finally came sinking in. After a long day, Sally wondered if she was really having this conversation.

Sally shook her head briefly. "I'm sorry, what exactly are we talking about? How did we get from a gift card, to a spa, to anal sex?"

"They're a spa which provides anal services. You know, they teach people how to enjoy it. They help couples expand their sex life. They work wonders."

"It certainly sounds interesting."

"You have no idea. Again, secret, remember? Don't tell anyone. And please don't write about it."

"Aileen, I always keep my promises."

"Well, then my work is done. Have a good night. And enjoy your trip to Italy."

Sally couldn't help but smile. "Goodnight."

"And keep me updated on your private adventure. I'll be checking my phone for email updates while you're over there."

"Will do. Have a good night."

After the call ended, Sally couldn't help but smile to herself, thinking how crazy life could be sometimes.

The trip to Italy was exactly what she had expected. She had been there a few times before, after all. But never in the midst of winter.

She enjoyed the sights and sounds and beauty of a cold Italy. She brought her laptop everywhere and wrote about the experiences.

In the back of her mind, she wondered about the place Aileen had recommended. The place where Aileen had finally stopped being so prudish when it came to sex. If that spa could make Aileen open up to anal sex, then they must be good at what they do.

It wasn't until Sally finished her work that she was finally able to look up the place. It was in a fairly secluded area near the shore. The building was small. Two stories. And it was wide.

Sally entered, not knowing what to expect.

The spa was a mixture of the very old and the very new. The structure looked as though it was made of clay. Old antiques and paintings decorated the walls. But at the same time, the latest computers and furniture were being used.

A few guests strolled around the place. Most seemed to be foreigners. Some wore bathrobes as they leisurely strolled around.

Sally was greeted by a young Italian man who spoke with a thick accent. Then she handed the man her gift card. He looked at the gift card and told her to wait.

After a few moments of waiting, a tall slender brown skinned woman came to the reception area. She was graceful and elegant in every way. She was dressed in a casual, but stylish, loose fitting Italian outfit.

Sally took note of the woman's beauty. Deep down, if Sally could look like anyone else, she would want to look like that Italian woman.

"I'm Gianna," she smiled, extending her hand. "Pleasure to meet you."

They shook hands. The woman seemed to be more fluent in English than Sally had expected. It was clear by Gianna's confidence and assertiveness that she was the owner of the spa.

"I'm Sally. Pleasure to meet you too."

Gianna smiled, "The pleasure is all mine. So, you're here because a friend wanted you to have our services."

"That's right. A gift from my friend Aileen. She said that you'd remember her."

Gianna continued smiling, "I never ever forget a client. We take great pride in our work here. Yes, I remember Aileen. Such a lovely woman. Amazing husband too."

"I'd have to agree."

"Why don't I give you a tour of our facilities?" Gianna asked. "We can talk and get to know each other better. That way, we can find out exactly what your needs are. Okay?"

The sultry Italian accent in Gianna's voice had Sally swooning. Sally wasn't a lesbian by any means, but my god that accent was hypnotic. So was Gianna's beauty. It was a further reminder why Italy was one of Sally's favorite countries to visit.

"Sounds great," she smiled.

The tour was fairly basic since the spa was rather small. There were open rooms for massages. Spa treatments. Saunas. The usual things.

There were also various sculptures & artwork of the naked female form. Classy artwork. It gave the spa a much more erotic feel to it.

And there were also private rooms for private treatments, which Sally wasn't able to see since they were occupied.

Afterwards, the two ladies sat down in Gianna's small office for a cup of coffee. They made small talk while they drank.

"Tell me," Gianna said. "Your friend has sent you here. Why?"

Sally knew where the conversation was headed. But she didn't feel comfortable discussing the anal thing right away. It was too embarrassing for a first time meeting.

"Maybe because I travel a lot, and she knew I was coming to Italy. I'm a travel writer."

Gianna nodded. "A writer. We have much in common then. I love the various forms of human expressions."

"Absolutely."

"Speaking of human expression, let's discuss how we may help you."

Gianna took out a small binder and placed it on the table. She opened it and slowly flipped through it. Each time she turned the page, she described exactly what services the spa had to offer, along with the prices.

Everything was discussed in a professional manner, and Sally was impressed by the depth of knowledge and care which Gianna showed.

In the end, it was understood that Sally's gift card had enough money for two appointments. But of course, Sally could always pay for extra appointments on her own.

"Have you got any ideas so far?" Gianna asked.

That was the moment when Sally finally decided to open up and enjoy her trip to the fullest extent.

Sally briefly tensed her body. "Actually, I had something else in mind. You see, my friend Aileen bought me the gift card with the understanding that I would explore certain things. Things which don't appear to be in anything you're showing me."

There was a smile on Gianna's face and a gleam in her eyes. The owner of the spa knew exactly what Sally was talking about, and it was finally time to stop pretending.

Gianna got up and went to a cabinet where she grabbed another binder. Then she sat back down.

"This is usually for couples," the owner explained. "I figured you weren't interested in this. Forgive me."

"No worries."

"Is there any special reason for your interest?"

"Well, it's a long story. My friend wanted me to experience this and I was a little embarrassed to ask you earlier."

"There's no need to explain yourself. Let's have a look."

Gianna opened the binder and flipped through the pages and pictures. The images were fairly explicit, but in a tasteful way. The explanations from Gianna along with the explicit pictures in the binder were all discussed in a professional manner. Everything from vaginal stimulation, oral sex techniques, erotic massages, and everything a couple would need to have a happy sex life.

The discussion was so casual, that it felt like a doctor's appointment.

That was another thing which Sally enjoyed about the Italian people. They were frank. Passionate. Open. And they were in touch with their sexuality, without shame.

After everything was explained, the two women looked at each other. Gianna gave a patient look, which showed that she was more than willing to wait if Sally needed more time. But Sally already knew what she was there for.

"I want the same treatment as my friend Aileen. Do you still remember what she was here for?"

A smile grew on Gianna's face. "I never forget a client's wish. Especially my American clients, who can be so much fun in different ways."

"Was Aileen fun to work with?" Sally asked out of pure curiosity

"Oh yes. I enjoy shy women who learn to be adventurous. It reminds me of finding the right oyster, taking time to open it, finding the perfect white pearl inside. Shining bright and beautiful."

Sally was strangely aroused thinking of her close friend being compared to an oyster with a pearl inside. Only instead of a pearl, there was anal satisfaction.

"Interesting analogy," Sally nodded. "So how does this process work?"

"Depends on the needs of the woman. If she's shy, hesitant, and timid, we go a little bit slower. We take our time to ensure maximum comfort."

Things sounded so smooth with Gianna's tender voice and Italian accent. It made Sally ready for anything.

Sally shrugged off any hint of embarrassment. "How would it work for anal?"

"Slow and steady. Plenty of deep tissue massage first. That always makes a woman relax. Everytime. Then while she's laying on her stomach, we spread her legs, after the massage. And we take things slow."

"Is that what Aileen did?"

Gianna nodded. "While her husband watched and observed. He penetrated her when she was ready."

The revelation left Sally taken aback. Once again, she found herself being aroused at the thought of her close friend's sex life. Who would have thought? The typically shy and prudish Aileen being sodomized in front of a beautiful Italian woman.

"I think I'm ready for something like that. Obviously without the penetration part."

Gianna raised an eyebrow. "Anal without penetration?"

"Well, I don't have a partner. That's what I mean."

"We can provide a partner."

Sally sat up straighter. "This is getting a little confusing. How would this approach work since I don't have a partner with me?"

"We have many options. Our masseur could use something inside of you. A small toy. A medium size toy. Or maybe even a large toy. If you're in an adventurous mood, maybe you will accept his manhood inside of you. If none of that appeals to you, then maybe my fingers will."

The tone of the conversation had turned far more sexual. All while Gianna maintained her cool European composure and sexy confidence. God, Sally only wished she could be that cool and confident in her own personal life.

"Do I have to answer that now?"

"Any time you'd like. We're certainly in no rush. Don't forget that you're in Italy. We have much slower clocks here."

"That's one of the things I love about Europe."

Gianna smiled, "What's your interest with anal stimulation? You seem so hesitant. But you're so curious, like a kitty."

"Long story. But Aileen bought me this gift because she knew it was a fantasy of mine."

"There's nothing wrong with this kind of fantasy. Embrace it. Be the woman you are. A beautiful woman with her own fantasies."

God, there was Gianna with her cool confidence again, Sally thought to herself.

"If it was only that simple."

"Ever have anyone play with you there?" Gianna asked with her accent.

"My butt? I've tried it with past lovers. No success. For years, I came to the conclusion that butt-play isn't for me. My backside probably wasn't built for it. But if it could work for someone like Aileen, then I'm sure it could eventually work for me."

"You seem to have a fascination with anal. Why?"

Sally tightened her lips and thought for a moment. "I've always thought of myself as an adventurer. Ever since I was young. When I was old enough to become sexual, I considered myself to be adventurous in the bedroom. I'll be honest, I kind of slept around in college. And later in my adult life. I've tried about everything there is to try, except for this."

"And you feel that anal sex is the one thing you haven't fully explored. Like you're missing pleasures of the human body."

God, this woman is good, Sally thought.

"Exactly. Aileen was my college roommate. We've talked about this a long time ago. That's why I was surprised when she bought me this gift card for the holidays and had me come here."

"A pleasant surprise, I'm sure," Gianna noted. "It's nice to have friends like that, who care about you and your needs."

"You're right."

"Do you have any problems down there? Anything making it difficult?"

Sally shrugged. "Just the size. I guess I'm just small in that area. It feels tight and I can't enjoy it."

"Fortunately, we know what to do. The anal cavity is adaptable. But it must be done with love and care."

Once again, there was a confidence and coolness to Gianna. She knew exactly what to say and how to act. God, that woman is perfect, Sally thought enviously about the Italian spa owner.

Anal Education

The room was small. The walls looked like they were made of flattened clay. There was a sink and a few supplies. There was a chair and a table. There were towels and moisturizers. Most importantly of all, there was a massage table in the middle of the room where all the magic would happen.

Sally undressed. She removed everything neatly and orderly. Being well dressed was something she prided herself on. And she made sure to handle her expensive clothes with great care. She folded everything neatly and placed them on a table.

She picked up the towel and wrapped it around her body. Frankly, she wouldn't really have minded if anyone at the spa saw her nude. She had a great body and she knew it. Hours of yoga and spinning classes were to thank. Her arms were toned and so were her legs. Her breasts were small and perky, with nice light brown nipples, which easily hardened with any form of arousal.

Perhaps her greatest physical gift was her backside. She had a nice round butt. Most of it came natural. She came from a long line of women with nice butts. But a lot of it came from hard work and a disciplined exercise routine.

"I'm ready," she said towards the half-opened door.

The door was thin and the people on the other side heard it. With a towel wrapped around her body, Sally sat on the massage table.

She became a little nervous when the door opened, and Gianna entered with a handsome Italian man.

Gianna gave a pleased look when she saw Sally sitting with only a towel on. If Sally didn't know better, she'd say that Gianna had the hots for her. So did the man, who made no attempt of hiding his interest in Sally.

"This is your masseur," Gianna said, gesturing towards the man. "He has the best hands in all of Italy, in my opinion."

Sally shook the man's hand.

"I think I might have to agree," Sally replied.

Gianna closed the door.

"Shall we get started?"

"We should."

"Remove your towel," Gianna said. "Lay on your stomach."

Without shame, Sally flung the towel away. Her fully nude body was briefly displayed for the two Italians to observe. The view of Sally's breasts and shaved crotch ended when she laid on her stomach. Her bare backside pointed straight up.

"Let's begin," Gianna said.

The spa owner snapped her fingers and the masseur went to work, arranging his assortment of oils and lubricants.

Moment later, Sally heard a bottle cap open. Then she felt a lukewarm substance being poured across her back. It went all the way from her shoulders down to her butt, even to her thighs. The feelings of the oily substance made her skin tingle.

Then the massage began. Gianna was right, Sally thought. The man had incredible hands. Just incredible. Within moments, Sally felt her back muscles being squeezed and pressed in various ways. The hands were strong and the fingers knew exactly where to press.

It was a mixture of pain & pleasure.

Sally felt her muscles being pressured in ways she had never felt before. And Sally was a woman who prided herself of being a veteran of spa treatments. Never had she felt anything like this.

Time flew by and Sally enjoyed her full backside massage. Her shoulders, the middle of her back, lower back, and thighs were all being rubbed & squeezed. Everything except for her naked ass, which she figured would come later.

After a while, Sally couldn't help but loudly moan & groan.

"I think it's finally time," Gianna said with her sensual Italian accent.

Sally was pulled out of the mental relaxation and was reminded of why she was there in the first place.

"What happens next?" Sally asked, still face down.

"That's up to you. You never gave clear instructions."

The back massage continued and Sally thought about how far she was willing to go.

"What are my options?" Sally asked.

"You seem timid, so we'll start slow. Here are your options: The fingers of the masseur. Maybe a small sex toy. Or my fingers."

Sally thought for a moment. Each option sounded intrusive, but in a dirty kind of way, which was very arousing.

The choice was pretty easy.

"Your fingers, please."

"Excellent. I love being the first to enter."

Sally's heart raced. "I like that you have slender and gentle fingers. I'm sure it will feel easy."

"I have a soft touch. You're in good hands, Sally. But first, you need a bottom rub."

Gianna snapped her fingers. Suddenly, the masseur brought his hands down to Sally's bare ass. With his strong hands, the masseur squeezed and pressed Sally's butt. It was like the masseur was kneading dough. In fact, Sally was entirely convinced that the male masseur was actually a full time bread maker, and giving massages was his part time gig.

The hands continued to squeeze and massage Sally's butt, which started making her even more aroused. Who knew that the female bottom could be such an erogenous zone? Sally was finding that out firsthand.

"You're ready," Gianna said.

Sally could hear the Italian spa owner walking over to the sink to wash her hands. The water ran and Gianna cleaned herself. When the water stopped, Gianna used a towel to thoroughly dry her hands.

Then there was the sound of Gianna opening a bottom cap. Then the sound of something being poured. Sally knew exactly what she was hearing. She heard Gianna lubricate her own fingers before the anal penetration.

The strong masseur spread both of Sally's legs apart. Then he spread Sally's butt cheeks apart. It was the moment of truth. Sally felt her anus being so exposed and vulnerable. She suddenly became self-conscious over the fact that the spa owner and the masseur both had a clear view of her little brown hole.

It was slightly embarrassing, but Sally took comfort in the fact that they must have seen plenty of butt holes. It must have been no big deal to them, just like doctors are immune to nudity because they see it so much.

"Relax my dear," Gianna said in her soothing Italian accent.

Sally's eyes opened wide as she felt the lubed finger press against the delicate ring of her anus.

That night. Sally was in her quiet hotel room. She sat comfortably in bed with the laptop resting on her thighs as she sat upright. At that hour, she knew her friend Aileen was also in front of the computer.

She sent an email entitled: An Education

Aileen,

The trip to Italy so far has been amazing. I'm loving the sights and sounds as always. But you already knew that I would.

You're probably wondering whether or not I've been to the spa. Well, I have. And I have to say that your gift was probably the best I've ever gotten. I have another appointment tomorrow. My last before I leave. : (

This has been an education for me.

talk to you soon,

- sal

The email was sent. Sally knew she would get a response soon. So she surfed the internet for a while. She also put the finishing touches on her travel writings. Everything looked great so far.

In typical Aileen fashion, a swift response was sent.

Sally clicked open the reply email:

Is that it? Details! Details! Details!

Aileen

Sally smiled to herself. It was the sort of response she expected. It reminded Sally of how Aileen was during college. Every time Sally had gone on a date, Aileen would wait patiently by the door until Sally arrived back to the dorm, curious about every single detail.

She typed her response:

Well, it's kind of a long story. I'll tell you the details when we meet for lunch.

But....I can tell you that Gianna is a very sweet woman. The masseur is also handsome as hell. After some discussion, the three of us were in a room together. I was treated to the best massage ever.

Then, the time came. I was given my options, and I chose Gianna's fingers (nice, thin, and delicate). My legs were spread. She lubed up. And that was my day!

With a quick click, the email was sent, and Sally was still smiling to herself.

She could imagine the impatient look on Aileen's face reading the email. It made Sally feel young again, teasing her friend over dirty little details of sex. But not just any sex, this time, it was details of anal play.

Within a minute, the reply came.

Sally clicked open the email:

Details!!!

How did Gianna's finger feel? Did it hurt? Were you comfortable? Most importantly, what will you be doing tomorrow?

Even more importantly than that, aren't you glad you have me as a best friend?

Sally smiled more. How she wished she could be back in America having hot coffee, sharing all the details with her friend.

But, that wasn't the case. They were half a world apart, and they needed to communicate through email.

Sally replied:

Yes, I'm glad I have you as a best friend! And we need to be on each others wishlist from now on. Until forever.

To your question, Gianna has a nice touch. Correction: A perfect touch.

That woman must be a sorcerer or something. Her skin is like olive oil. Soft silky and smooth. She knows exactly what to do. What angle. What pace. ect...

She's skilled at playing with a woman's ass (if that's even a compliment).

After that amazing massage I had, my ass was ready for anything. But, I wanted to start slow and small. Gianna's finger was the perfect gateway to anal pleasure for me.
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