Sally’s Wish, Anal Education

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.

She pressed her lubed finger against my little butthole. I'll admit, I flinched like a wimp. But I held my ground. I'm a big girl. I accepted the finger going inside my butt. It felt so awkward. Like it wasn't supposed to be there (and of course, it wasn't!) But it felt nice.

The second I got used to it, Gianna pulled back, then came two fingers. So there I was, laying naked on my stomach, with two fingers inside my butt. Awkward.

She probed and searched. I felt my rectum being stretched in unusual ways. The whole thing must have lasted a few minutes. Gianna's fingers never relented. They worked and worked. And I stretched and stretched.

She knew I had enough for one day. I don't know. Maybe it's female intuition. But she just knew. So she ended the session.

When she pulled out, my asshole felt a slight gaping feeling, like something was missing. Her fingers had been inside me for so long that my butt had become accustomed to having it there. Weird.

Anyway, I'm meeting her again tomorrow early morning. Then later, it's back to America.

I have no clue what I want. I'm not expecting anything drastic. If I only get an amazing body massage, I'll be fine with that.

If we continue our anal adventure, I'm okay with that too. We'll see how it goes. I'm pretty excited to go back to the spa tomorrow.

- sal

The email was sent. This time, Sally didn't expect an immediate reply. Not after she had just written so much. She knew that Aileen would take her time combing through every single word.

Minutes passed and Sally just surfed the web. She verified her travel plans and looked for places to eat in Italy.

Then, she got a reply.

Sally clicked open the latest email from Aileen:

I'm so jealous right now! I wish I could be in Italy too.

I'm also very glad that you're experiencing this.

Can I make a suggestion? You only live once. I'm sure there's plenty of cash left of that gift card. Make the most of it.

Forget the fingers. Forget the sex toys. Have that masseur plow your bottom. I never asked for that, since I'm married, obviously.

But when I was there in Italy, I heard him pounding some lady. It was loud. And I mean really loud. It sounded so painful too. But when I saw them leaving the private massage room, that lady was swooning. I mean, she was practically floating in the air after that pounding she took. I also think the woman needed some help walking, but that's another story.

I also recommend asking Gianna to get more involved. I don't want to ruin any surprises, but that woman is a sexual goddess. You should request her further assistance in your anal experience.

Sally. You're beautiful, smart, and fun. I envy your position right now. Make the best of your holiday travel. Make the best of your gift card.

Love,

Your friend

Aileen

The smile couldn't be wiped from Sally's face. She wished she could give her friend a big suffocating hug. But that hug needed to wait a while.

The only thing Sally could do was reply.

She sent a final email for the night:

Aileen,

You're the best. I'll be back soon, full of stories.

Stories of my education.

Our secret.

Love,

Your friend

Sally

Their email correspondence had ended and Sally closed her laptop.

After washing herself in the bathroom and finishing her nightly beauty routine, Sally wondered about the next day. She wondered how far she was willing to go with her anal education.

In many ways, Aileen was right. The opportunity was there for Sally to explore. It was the gift she needed. It was Sally's chance to finally explore parts of her sexuality with people who were experts.

She turned off the lights and went to sleep. She knew tomorrow would be a good day.

Part 3 of 3: Gianna's Touch

The two women sat in the office for a cup of morning coffee. Once again, Sally found herself admiring Gianna's style & beauty. The Italian woman was simply impeccable.

They made small talk and leisurely conversation. It was like they were old friends. Gianna had a way of disarming her guests and making them feel right at home. It was like they knew each other well. Besides, Gianna already had her fingers inside Sally's butt. What's more intimate than that?

"Have you thought much about yesterday's activities?" Gianna asked.

"I've thought about it a lot."

Gianna smiled, "Not too sore, I hope."

"I'm fine," Sally smiled back. "I've emailed my friend Aileen about this. She's thrilled that I came down here to explore this."

"How is Aileen doing?."

"She's doing great. But she's a little jealous that she's not here with us."

"It's paradise here," Gianna replied.

"Speaking of paradise, Aileen had a few recommendations."

Gianna raised an eyebrow. "Oh?"

"It's a little embarrassing. But today is my last day here, so I figured I might as well enjoy, right?"

"That's what I like to hear from my guests. This is a spa for relaxation and re-invigoration. So, what can I do for you?"

Sally was normally an outgoing person. She was rarely ever shy or hesitant to ask about anything, after all, she was a writer. But in that moment, Sally felt her body tense.

"I've been told to render the services of your masseur," she replied, trying to be brave. "You know, his services."

Gianna gave an understanding nod. "That can be arranged. Our masseur is a man of great talents. He also thinks you're very beautiful. He will be pleased to hear this."

"And there's another thing."

"Yes?"

Sally nearly blushed. "I've been told to include you. I don't know. Aileen mentioned something about getting you involved. I'm not sure what that means, but I figured I'd just ask to find out."

Gianna continued nodding. "Truthfully, the balance on your gift card doesn't cover all of this. However, you are my guest here. Consider this a bonus."

"I can pay the extra costs for your services. It's really no problem."

"No. I insist. My gift to you. This will be a real pleasure for the both of us."

Sally noted the expression on Gianna's face. It was an expression of anticipation and excitement.

"Thank you. This sounds like something to look forward to."

"Your gift card, please," Gianna asked.

Sally searched for the gift card in her purse and handed it to the spa owner. Gianna got up and swiped the card through the machine. She typed a few things on her computer and printed out a receipt.

The receipt was handed to Sally, along with the emptied gift card. When Sally looked at the receipt, she saw that the charge was $500. All expenses paid for by the remainder of the gift card, and a special courtesy from Gianna.

The name of the cost was 'The Full Treatment'. Sally felt a tingle between her legs, wondering what the full treatment was.

***

Once again, Sally was in the same little massage room. She still had no idea what was going to happen next. The instructions were a bit vague. But maybe, she figured, that was all part of the fun.

She undressed fully. She was naked & barefoot. She was much more relaxed than the previous day. In fact, she was excited to continue her anal journey with the beautiful Gianna and the handsome masseur.

Sally put on a towel to cover her nudity. Then she slightly opened the door.

"I'm ready," she called.

Sally waited in the room for a moment.

Her eyes slightly widened when she saw Gianna enter the room wearing nothing but a silk robe. The spa owner's hair was tied in a ponytail. She was even barefoot.

The masseur also entered the room in a robe, and he closed the door once they entered.

Sally knew that things were about to get very very interesting.

"Looks like we're all ready," Gianna smiled. "Shall we continue to make small talk to relax? Or shall we get to business. Your choice, dear."

Sally took a deep breath. "Well, we're all here for a reason."

"Very well. Let's begin."

Gianna gestured to Sally's robe, signaling her to undress.

Sally took the cue and disrobed. She wasn't as nervous as before. In her philosophy, it was just like going to the doctor. No one is really shy being naked in front of the doctor. That's because you normally wouldn't see the doctor in your everyday life. You go there for a purpose, do you business, and leave.

For a few seconds, Sally stood unabashed at her own nakedness. She kind of enjoyed the fact that Gianna and the Italian masseur both stared at her naked body in an aroused way.

"On my stomach?" Sally asked, hands on her hips.

"That would work best."

Sally ended the nude show when she laid on the massage table, which had towels neatly wrapped on it. It was comfortable & cozy. Sally immediately felt relaxed laying face down.

The sink was being used. Both Italians washed their hands as if preparing for a medical operation. And technically, Sally thought, there were many similarities to a surgery. After all, Sally was about to have her bottom opened (but for the purpose of sexual pleasure).

They dried their hands. Sally heard the noises of bottle caps opening and she soon felt lukewarm oil being applied to her entire backside. Sally's back, thighs, and butt, were all coated with the slick substance.

Sally felt an immediate bliss as Gianna and the masseur both started rubbing her back. Two pairs of hands were unbelievable. It was much better than yesterday.

Not only did she feel the strong hands of the masseur, but she also had the pleasure of feeling the soft feminine hands of Gianna. It was quite the contrast, and double the pleasure.

They rubbed everywhere, from the top of her back, to her lower calves, and everything in between, included her toned butt.

Despite the occasional jolt of pain from hard squeezes, Sally felt bliss, and she was ready to fall asleep at any moment.

"Now you're finally ready," Gianna said with her sultry Italian accent. "Shall we begin with the full treatment?"

Sally was surprised that it hadn't started yet. If that full backside massage by two experts wasn't the full treatment, then what was? Sally was more than eager to find out.

"My body is ready for anything," she groaned, still reeling from the amazing massage.

"Very well."

Sally heard the noise of something dropping on the floor. It must have been cloth or a towel, Sally figured.

Then, Sally felt a unique pleasure on her back. Too soft to be hands. They were two round globes rubbing against her back. Then she felt them harden. It took a brief moment for Sally to realize that Gianna was rubbing her bare tits on Sally's backside.

It was such an arousing thought. Sally wondered if Gianna was fully naked while doing it. The only thing Sally knew was that Gianna's tits felt nice against her skin. Both nipples were hard and rubbed across Sally's back, then to her thighs, then finally her butt. It was a sexual massage that was achieving its intent, which was to further arouse Sally.

Sally heard Gianna's fingers snap.

In an instant, the strong masseur grabbed both of Sally's ankles, and spread her legs. Sally felt her legs open and her asshole exposed. She knew both of the Italians were looking inside.

Gianna used her soft hands to spread Sally's butt wide open. They had an even better view of Sally's naked asshole.

She expected more oil to be poured inside of her ass. But that didn't happen.

Instead, Sally felt soft feminine lips kissing her butthole. The kisses came all around her exposed anus. It felt nice. Sally never had the pleasure of feeling her anal region being kissed before. She thoroughly enjoyed it.

Then came licks. Oh god. Sally felt the outer ring of her anus being licked by Gianna. It was such a thrill and it made her pussy drip. Sally felt her heart pounding as the anal licking continued.

If that wasn't enough, Sally felt the warm tongue being pushed inside of her ass. Oh god. It tickled. It stimulated her nerve ending. It made her even more wet. The tongue licked and swirled around the ass.

Sally mumbled a few things which didn't make sense. She just wanted to mumble. She wanted to moan too.

The tongue was removed. Then Gianna said something in Italian.

Oil was being poured in Sally's anus. It was lukewarm and it kind of tickled as it flowed into Sally's outer hole and inside her rectum.

"Let me know if this hurts, dear," Gianna said. "We'll take good care of you, okay?"

"Okay."

This time, it was the strong masseur who held Sally's ass cheeks wide open. His grip was firm and tight. There was no way Sally's butt cheeks were going to move.

The tip of a smooth sex toy pressed against Sally's anus. The girth felt small, but Sally had no idea how long it was. It was all a mystery. All she knew was that it was solid but it felt smooth.

A small push and Gianna was able to get the sex toy inside of Sally's vulnerable ass. It was slowly pushed and it slowly went all the way inside.

Her tiny little asshole was being stretched in an unnatural way. It hurt, but it also felt pleasurable in a strange way. Nerve endings she never knew existed were being stimulated when Gianna slowly worked the sex toy in & out.

"How do you feel?" Gianna asked, the same way an experienced doctor would.

"Stretched."

"Good?"

"It feels nice."

"Something bigger?" Gianna asked.

"Do I have to?"

"Only if you want the masseur to take your anal virginity," Gianna asked in teasing way.

The comment grabbed Sally's attention more than the sex toy in her ass. It was the moment of truth and she had to quickly decide.