Sally’s Wish, Anal Education

"Fine."

"Are you sure?" Gianna asked with a purposely thick Italian accent.

"You only live once, right?"

"That's right my dear."

The sex toy was slowly pulled from Sally's rectum. It gave her butthole a slightly gaping feeling as it returned to normal size.

Before her anus had time to readjust, a slightly larger sex toy was pressed against her anus. More lube was poured. Gianna gave a slight push and the sex toy entered Sally's tender butt.

"Oh gosh," Sally gasped, her body reflexively tensing.

"Be still, my dear."

Sally tried her best to hold still. The strong masseur continued his tight hold on Sally's butt, to ensure that her rectum would remain open.

The larger sex toy was slowly being pushed. Sally felt the tight ring of her anus being stretched. She felt her rectum being stretched as it went even deeper. It went deeper than anything that's ever gone inside before.

Then slowly, it was pulled out. The movements continued slowly. In & out. Gianna knew exactly how to treat a tight little asshole like the one Sally had. The spa owner was a true professional at what she did.

"Things are progressing nicely," Gianna said. "Your body is learning to adapt. I can tell you're very tight and sensitive."

"I've never had anything so deep before."

Gianna gently pushed the sex toy all the way inside, causing Sally's muscles to clench.

"Don't fight it. Don't clench. Just relax. Let go. Trust me, Sally. I know what I'm doing."

The sex toy continued its in & out motion, while Sally fought the urge to clench her rectum.

Finally, the toy was pulled away after a few minutes. It was followed by another deep gaping feeling in Sally's butt.

"Are you ready to lose your anal virginity?" Gianna asked with a thick Italian accent, knowing that her accent turned Sally on.

"Only if you think I'm ready."

Gianna patted Sally's butt. "You're ready, dear. I've made you ready. Mentally and physically, you're ready to accept a cock. Relax and enjoy. He knows how to handle women."

There was a noise of a robe hitting the floor. As Sally laid face down on the massage table, she knew that the male masseur was also naked.

Her heart raced. She knew she was about to be anally fucked by the strong handsome man. Oh god. She wondered if she was truly ready for it. She wasn't sure. But she was willing to try it out. After all, she was on vacation and she wanted to try new things.

The man climbed onto the massage table, on his knees, right behind Sally's spread ass. He nearly mounted her from behind, with his cock pointed towards Sally's vulnerable and lubricated asshole.

"I'm going to get him hard for you," Gianna said. "I will also lubricate him at the same time. He will be ready for you."

As Sally laid face down on the table, she suddenly heard sucking & slurping noises fill the room. She knew right away that Gianna was sucking the man's cock. What better way to get a man hard?

The slurping sounds lasted for nearly a minute, followed by a loud 'plop' sound as Gianna pulled her mouth away.

"He's ready," Gianna said. "My saliva is warm. The temperature should feel nice. And he is throbbing hard for you. Are you ready?"

Sally questioned herself once again. She was nervous about being anally ravished. But she was also very wet and aroused.

"I'm ready."

"Hold still. Tell me if it hurts."

Gianna used her soft hands to spread Sally's butt cheeks apart. Then Gianna used her fingers to guide the hard cock towards Sally's anus, as the masseur lowered his body.

The hard cock pressed tightly against Sally's anus, at the guidance of Gianna's fingers.

Gianna said something in Italian, and the man gave a slow press against the anus. The man entered and the tip of his cock went inside Sally's tight little asshole.

The spa owner was right. Her saliva on the cock was warm and it felt nice. The sensation added to the anal experience. The stretching didn't hurt that much since her ass had already been prepared from the lube and sex toys.

He entered further. Inch by inch, the shaft of the thick cock went deeper in Sally's rectum. She squirmed and moaned. But she fought to remain still. It hurt. It ached. But it also felt amazing in a strange way.

She felt herself being stretched to capacity as Gianna continued to guide the cock inside of her butt. She knew there were a few more inches to go. And she was ready for it, she hoped.

"Relax dear," Gianna said softly. "Almost there. Almost there. You're doing wonderful, my dear."

Sally felt her ass being completely filled to capacity as the cock entered all the way. The masseur's crotch pressed fully against Sally's butt.

At that point, Gianna had already let go. Her fingers were no longer needed to guide the cock inside.

Gianna moved from the table and crouched down in front of Sally. It was the first that time Sally had seen Gianna naked.

The spa owner had a slender body. She was crouched down with her legs wide apart, showing the inside of her spread vagina. She had a dark patch of pubic hairs. Her chest was flat with very large dark nipples. Her chest was still covered with oil from the breast rubbing she did earlier.

Simply put, the Italian woman was a striking beauty. Just as Sally had expected she would be without clothes.

"You're doing amazing," Gianna said. "Look at me, relax dear."

The spa owner held both of Sally's hands as a loving gesture. They looked each other in the eyes while Sally's asshole was stuffed by the raging hard cock.

There was a look in Gianna's eyes which said, 'You can do this. You're a strong woman. You can do anything. It's going to be worth it."

It was a look which gave Sally confidence as the cock slowly began to slide out of her ass, and then thrusted back in.

Sally squirmed and her body struggled. She tried to hold still. She did her very best. Her face grimaced as her ass was filled by the raging hard cock. Her facial expressions tightened, all while Gianna tried to sooth her.

"Relax dear," Gianna said in a loving manner, rubbing Sally's hands in the process. "I know it's difficult. But you will have the beautiful gift of orgasm when this is done. I promise."

The two women held each other's hands. Sally squeezed tightly as the masseur went harder. Gianna squeezed her hands in return. They continued looking each other in the eyes as Sally made grimacing faces from the pain.

At that point, after Sally's asshole was ready, the strong masseur really started to go at it.

The thrusts were harder and far more intense. Sally's asshole was taking the pounding that she had fantasized about since college, but was never able to experience. Her tiny little asshole was finally getting the overdue fucking it long desired.

It was the final piece of Sally's sexuality that she had yet to experience. Her anal virginity was being taken away in spectacular fashion. All while Sally screamed and moaned while her ass was getting properly fucked.

The two women continued holding hands and making eye contact. Gianna continued her words of encouragement as Sally screamed in pain & pleasure.

"You're almost there," Gianna said, with lust in her eyes and voice. "You're almost there. So close. Don't give up."

The ass pounding continued and Sally's rectal nerve endings were being stimulated in a powerful way. Her rectum was stretched to capacity by the hard pounding cock. It was beginning to take its toll as the pain grew.

Gianna spoke in Italian to the male masseur. It was a brief sentence which Sally couldn't understand. But the masseur sure did.

He continued fucking the poor little asshole with expert precision, while reaching down with one hand, underneath Sally's thigh, to rub her sensitive clit.

Sally cried.

The masseur fucked her asshole and rubbed her clitoris in a circular motion.

Sally cried some more.

Her pussy was dripping wet and fluids were leaking.

"You're almost there darling," Gianna said, holding Sally's hands tighter. "I can see it in your eyes. Relax, my dear. Let it all out."

Gianna spoke Italian again to the masseur. He got the message and pounded Sally's ass with full force. He rubbed Sally's clitoris even faster, making the woman cry. It was all too much for a woman to handle.

"Oh god!!!" Sally cried, clenching her eyes shut.

Fluids squirted from her pussy and made a mess. Thankfully the towels were spread neatly across the massage table. More fluids gushed from Sally's pussy as the masseur's sexual ravishment continued at a relentless pace.

He continued fucking her ass. He continued rubbing her clit.

Sally continued clenching her eyes, groaning, while the fluids continued to seep from her pussy. Her back muscles were contracting. Her legs completely stiff. Her toes curled. Her jaw wide open. And her eyes clenched shut.

The two women held each other's hands tightly. Sally squeezed with a grip she never knew she had.

Then, it was over.

Sally collapsed and was nearly lifeless while the man gave a few more pumps in her asshole.

The masseur had cum inside of Sally's rectum. He was breathing heavily. Then he pulled out. His penis was in a semi-flaccid state, covered in his own cum, Gianna's saliva, and plenty of lubrication.

He laid on the massage table, right next to Sally, who still remained nearly lifeless.

"You did it, darling," Gianna said softly in Sally's ear. "You came."

Gianna ran her fingers through Sally's hair. She marveled at the peaceful sight of Sally in a state of pure bliss.

Then the spa owner bent down to give Sally a kiss on the forehead, then the cheek. The next kiss was on Sally's lips, which was enough to wake her up. They continued kissing on the lips.

Sally had been with women before. She was no stranger to a lesbian kiss. But there was something extra special about kissing Gianna. Maybe it was the fact that Gianna had soft sensual lips. Or maybe it was the fact that Sally had just received the orgasm of the century.

Whatever the case, it felt amazing.

The kiss ended, and Gianna smiled. Then Gianna stood to admire the handiwork of the masseur.

Sally's body was a mess, covered in oil and sweat. Her legs still spread. Cum and lubrication leaking from her asshole. Squirt was everywhere between Sally's legs.

The spa owner was always pleased when guests were satisfied. And by the looks of things, Sally was more than satisfied.

Gianna bent over the table and inspected Sally's asshole. It looks like a gaping messy hole. Well fucked and recently stretched.

The spa owner spread the ass cheeks once again, bent down, and gave the asshole a nice big lick, followed by a long suck.

Sally groaned.

***

It was an hour later by the time Sally left the spa.

She had just finished a warm bath. Her hair was nice and neat. Her make-up was freshly done. And her clothes had been pressed by the staff. She looked like a new person when she went outside with her sunglasses on.

Her last memory of the spa was giving Gianna a kiss on the lips. Then another. Then another. Until finally they embraced in a long tongue kiss.

While she walked down the street, Sally took out the phone from her purse. She needed to text Aileen.

She sent a simple message:

success!! i have so much to tell you. thnx for everything. best gift ever. next year, i'll need another gift card.

love,

sal

The message was sent.

Sally smiled to herself as she walked down the street with a slight limp in her step. It would probably be a few days until the soreness was gone.

The End

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