Anal Escort #1

This story is inspired by Thunder2Metal's works.

Lana had hired an escort who specialized in anal. This is their story.

Nancy didn't know what to think about Lana. She seemed so young, so naive - and yet there was something else about her... something Nance couldn't quite identify.

"Your asshole handled my fist pretty easily. But width is just one dimension, isn't it? Let's test your depth." Lana took the slink toy from the closet. It wiggled as she held it by the base. It was bright green and mostly smooth, but one side had round bumps like an octopus tentacle.

"Have you tried one of these before?" Lana asked, showing her the toy as she applied lube.

Nancy nodded. She wasn't too concerned. It was soft, thin, and quite flexible. As long as Lana didn't push too fast, she was sure her bowels could handle it. However, it was very long. She watched as Lana added more lube, stroking it like a cock.

"Turn over onto your back, and lift your legs. I want you to watch as I push it in."

Nancy did as instructed. She pulled her knees up, giving Lana access to her asshole.

Lana slipped the tip in. It went in easily, Nance barely felt it - at first.

"How does it feel so far?" Lana asked, never taking her eyes off the toy.

"Nice. The ones I have are just smooth. I've never tried one with bumps," Nance answered.

"Each bump is an inch apart, so you can tell how deep it is. That's six inches so far."

Nancy nodded. "I'm ready for more."

Lana pushed slowly. "Seven... eight... nine."

"Easy. Give me a moment."

Lana ignored her. "Ten... eleven... twelve."

"Ohh..." Nance groaned. "I said..."

"I heard you. I just don't care. Thirteen... fourteen... fifteen." Lana's eyes were fixed on the toy as it gradually widened, stretching Nance's asshole."

"Please. Just a moment." Nance was having trouble keeping her legs up. She was feeling the thick part of the toy now, she must be near the base.

"Stop begging. I paid, I'll do what I want. Sixteen... seventeen"

"It's starting to hurt. It feels... warm."

"Quiet. You'll make me lose count." She pushed past another bump. "Eighteen... nineteen."

"How... how many more?" Nance asked quietly.

"It's thirty inches long, so... eleven more? Math was never my best subject." The toy widened more; her asshole was stretched to the size of a tennis ball now. It was getting hard to push it in, but Lana persisted. "Twenty! That's impressive."

"If you're planning on going deeper, can you add some more lube?" Nance pleaded.

"More lube? Are you sure?" Lana asked, smirking.

"Please," Nance nodded.

Lana squeezed another dollop of lube and rubbed it around the toy just outside Nance's stretched hole. She pushed it in. "Twenty-one."

"It feels really... warm. What kind of lube is that?" She was struggling to hold her legs up.

Lana noticed and got a strap from the closet. She slid the looped ends over Nance's feet and pushed them up to her knees, then pulled the strap over her head. It held her legs up even higher and forced her head forward, forcing her to look at the toy. Nine more inches, and it got thicker with each one...

She watched as Lana twisted and pushed. "Twenty-two."

Nancy's asshole was as wide as an orange now, and starting to hurt. She'd taken larger objects before, but this seemed more painful.

"It's... burning," she whimpered.

Lana smiled. "'Yes, that's the lube. I mixed some cinnamon oil and Tabasco sauce in it," she explained in a calm, matter-of-fact voice. "It's going to get worse." She pushed another inch in. "Twenty-three."

Oh fuck she thought. What had she gotten herself into?

Lana pushed hard. The base of the toy flared wider. "Twenty-four. Not bad, just six more inches. But it sure gets thick, doesn't it? I bet it's as wide as a softball."

Nancy didn't respond. She was trying to hold back the tears. Her asshole was on fire.

Another push. "Twenty-five!"

"Please... I don't think I can take any more," Nance begged.

"We'll see," Lana responded. Her voice was so calm, so... clinical. She pushed again. "There, twenty-six. I knew you could take more. Do you want some more lube?"

Nancy couldn't answer - her mouth was clenched in pain, but she quickly shook her head.

Lana smiled. "Okay." She pushed again, putting her weight behind it. The toy went a little deeper. "Twenty-seven!"

Nancy's eyes were closed tightly.

"Do you want me to stop?" Lana asked.

Nancy quickly nodded.

"I'll stop... on one condition. I want to cuff you."

Nancy nodded. She could barely think straight.

Lana eased the sling over Nance's head, allowing her to lower her legs.

"Thank you," Nance whispered.

She attached cuffs around Nance's wrists and secured them behind her head. It forced her breasts forward.

"You have lovely tits," Lana observed as she tugged and twisted Nance's nipples. "I'm going to add some clamps."

She fished around in the closet and found a small length of chain with a clamp on each end. She secured them snugly to each nipple, pulling on them to make sure they were on tightly enough.

It hurt, but Nance ignored the pain. "Let's take the slink out now," She requested, trying to keep her voice calm and steady. She had felt like the one in charge when the session had started, but no longer. Lana had seemed so young and inexperienced. But somehow, the mousy girl was in control now.

"Sure, after we get it all the way in. Just a few more inches."

"You said you'd stop..." Nance whined.

"I did stop. But I didn't say for how long." She used both hands and forced the toy deeper. "Twenty-eight." Lana pushed again, but the toy didn't move.

"Let's try another approach." She pulled a tall stool over next to the bed. "Sit on this," she directed.

Lana helped Nance stand and turn around, and then lowered her stuffed ass onto the stool. Her ass offered some padding, but even so, her weight forced her down, pushing the toy in deeper.

"Twenty-nine," Lana noted. "So close! Just a bit more weight, I think."

She put her arms over Nance's shoulders and lifted herself off the floor like she was going on a piggy-back ride.

Nancy groaned as the widest part of the toy passed her sphincter and the final inch disappeared into her.

"There. I knew you could do it!"

She helped Nance stand and return to the bed, face down now.

"On your hands and knees, and I'll see if I can get it out." Nance struggled to her knees. "Err, I guess your hands are busy. Face down, ass up, that will work."

It wasn't easy, but with enough leverage, Lana managed to get the flared base past her anus. Once the flare was out, the rest was easy. Backing up, she removed the toy - all thirty inches.

"Wow. I've never seen a gape that big," she observed. "I bet I could fist you again and you wouldn't even feel it."

"Are you up for some ass-to-mouth?" Lana asked, but she didn't wait for an answer. She carried the slink to the other side of the bed, pushing Nance onto her side.

"Open up!" She held the slimy toy just inches from the woman's mouth. Nance opened her mouth.

Lana thrust it in, getting about six inches before it stopped. "Suck it clean," she ordered as she thrust it in and out, getting slightly deeper each time. Nance could taste the mixture of cinnamon and Tabasco from the lube, but it didn't mask the foul taste of her own filth.

She had given herself an enema before the session, of course, and that helped. But the slink had been deep in her bowels.

"That was exhausting, wasn't it? I think I need a snack. Do you want one? Oh, never mind, I guess you already have one." She patted Nance's cheek. "I'll be back in a few minutes. I expect that toy to be clean, understand? If you do as you're told, I may let you have a glass of wine."

Nancy nodded and began licking the long shaft.