After a long night out, this is my first anal experience.

Helena and Damien stumbled into the extravagant apartment. After six months together, Damien was eager to openly discuss their first anal fucking.

They had fucked before but not the way he preferred it.

Helena was visiting New York for the first time. Damien took Helena away to impress with his penthouse apartment.

Although he hadn't been back in over a year, he had pictured Helena's perfect sex as a place to bury his dick since the moment he first saw her. This seemed the perfect location.

Perhaps he could even get her to try anal fingering. She'd been there before, but it was not something she had ever considered.

Helena took off her high heels and fell onto the couch. The brunette bombshell's ladyly curves were perfectly matched by her tight red dress.

It was already 2am, and they had been drinking at all the top bars in the city. He had to ask now if he wanted to.

He drifted across the couch, feeling the effects of the Bourbon in his system on his balance.

He leaned down and gave Helena a passionate kiss. Too many Pornstar Martinis.

This was the right time to propose their first anal encounter

Damien delivered his most passionate delivery.

In the past, it had never failed him.

She whispered, "I think you know, Damey," back.

Damien knew but wasn't certain that she did.

"I want to fuck your in the ass. Tonight."

He slightly backed away and looked at her, trying to gauge her reaction.

Helena licked her lips. Helena didn't seem to be opposed to the idea, but she was thoughtful.

As Damien waited for her reply, he felt like an eternity had passed.

"Okay. "It's about the time I had my first anal fisting," she said.

She pulled the dress down by moving the straps from her shoulders. In her black, lacy and fitted underwear, she stood there.

As Helena took off her last lingerie, Damien began to undress. He was a step closer and she locked eyes with him.

"Be gentle."

Slowly, she turned around and settled down on the couch. She was laying on her elbows on high arms and her knees were sinking into the plush cushions.

Damien took a moment to admire the floral tramp stamp on her lower torso. He was a fan of tattooed ladies.

He found the lube hidden under the sofa cushions.

Damien opened the Lube lid and took position behind Helena.

His pulse was beating against his neck. He was eager to have his first anal encounter with this woman.

He applied a generous coating of the lube to his cock, and was ready to insert it in Helena's tight sock.

She let out moans of anticipation, and the sounds only intensified Damien's desire.

He had his hands sore from the lube that he began to finger lightly. Helena was shocked but didn't stop.

Slowly, he extended his fingers outwards and added another.

Helena groaned, "Mmm...that feels nice."

"Are you ready for my big, fat dick honey?"

"Mm-hmm."

Damien could see the smile on her face. He was thrilled that she was enjoying it.

To make himself more space, he backed up. He stooped down briefly and spread Helena’s cheeks. He quickly gave Helena a quick, playful lick.

She jumped with excitement and giggled wildly.

"Stop making Damey wait!"

Helena was only seconds away from her first anal fucking

Damien glanced briefly at the ornate cabinet in a corner of the room. His anal toys were found inside.

He quickly considered going to get them but decided that he could not wait. He turned his attention back to the woman standing on her fours.

"You got it, baby."

He slowly moved his cock towards Helena, holding his dick in one hand. He mocked her by drawing the ends of his throbbing, erectile erection.

Helena's repressed excitement had reached fever pitch.

He smiled and leaned forward, pushing his hips forward. He nearly missed her outbursts of pained pleasure and his own guttural sounds.

Damien was taken aback by her red-hot insides.

He slowly increased the pace of his fucking. Although he wanted Helena's first encounter with an anal was a positive one, he also knew that it would probably be painful for her.

She begged for help from the sidelines, "Faster, Damey!"

He was taken by surprise when the unexpected request arose and an uncontrollable surge of arousal shot through his body.

He immediately switched up the pace, spanking his soft cheeks simultaneously.

"You. Don't. Have. To. Tell. Me. He managed to speak twice."

Helena clearly sensed that he was getting closer to Helena.

"Yeah baby, cumin my ass!"

The command accomplished the task.

Damien was soon delivering his hot payload to Helena. Her body clearly expressed appreciation for the experience by starting squirting simultaneously with him.

Damien had to wait until his dick stopped convulsing before he could help him.

After only a few seconds, his cock was out of Helena's mouth.

He sank into the corner of a couch and breathed hard, slipping around his shoulders.

Helena looked around, her legs shaking. Damien was shocked when Helena gave him a kiss on the cheek.

He placed her head on her chest. "You have wanted to do that for a while to me, haven’t you?"

"This would be an understatement."

Helena smiled. Helena smiled.

She stood, her legs unsteady, and began to walk toward the bedroom door.

She said, "When 'later is' is, it is up to you," without looking around.

Helena and her perfect sex disappeared into the darkness of Damien's room. Damien was eager to get up and go. He got up from the couch and was standing right at her tail.