Careless Whispers (part eight) [Anal] [DP] [Comforting/Encouraging]

When I got back in the room Ray was eating Gia’s pussy again, he stopped and wiped his mouth off when he saw me.

“Set the camera up here, facing the bed,” he said.

I did and he adjusted it to the angle he wanted it, right behind Gia, and pointed up at her cunt and ass when she was on her hands and knees. Then he looked at me, “Now you get undressed and lay on the bed there,” he said.

“What?” I asked.

“You lay down on the bed, she’s going to kneel over you,” he said, as if explaining it to a child.

“Why do you want me naked on the bed?” I asked.

“I want her relaxed and something tells me you in her cunt and looking at her is going to make her relaxed,” he said.

“She’s never done anything like that before,” I said to him.

He laughed, “Looks like I get to participate in one of her firsts then.”

Gia looked at me, “It’s okay Dean, I can handle it.”

I looked at Gia, “It’s going to hurt,” I said.

She nodded, “I know. I’d rather it be with you than someone else, though.”

I started unbuttoning my shirt and Gia reached out to me. I moved over to her and she took over undressing me. I didn’t want her to see that I was hard, but there was no hiding it. She slid my clothes off of me and she smiled when she saw me. I couldn’t look her in the eye. I laid down on the bed directly in front of the camera and she climbed over me. Ray hit record on the camera and came over to us.

He spread the lube on, and in, Gia’s ass with his finger. She kept her eyes locked with mine. I tried to break eye contact but she put her hand on my jaw and forced me to look at her, moaning softly as he pushed the lube deep into her ass.

Ray looked over her shoulder at me, “Relax her, Dean, or this is going to hurt her more than it needs to,” he said quietly as he coated the entrance to her ass in more lube.

I wrapped my hand around to the back of her neck and pulled her down so I could whisper to her, “I’m so sorry, Gia. I didn’t know he was aware of your show, it never even occurred to me that he might be.”

She nodded and smiled then kissed me slowly and deeply. My hand tightened on the back of her neck and I felt her gasp as Ray started working his cock into her ass. I rubbed her jaw and kissed her more passionately, trying to distract her from the slow thrusts pushing her closer to me.

He grabbed my leg and pulled me closer to the edge of the bed, then he grasped her hips and pulled her back to him, pushing his dick a little deeper. She cringed and cried out. I started working my fingers in her cunt and on her clit. My other hand clung to the back of her neck and guided her head back down to my shoulder.

I looked Ray in the eyes and he pushed a little harder into her, causing her to whimper softly. My lips were right beside her ear, “You’re so fucking beautiful, baby girl,” I cooed to her.

My fingers worked her cunt and her head rested on my shoulder and my lips were on her neck. I inhaled deeply as I fought the urge to murder my boss. The scent of her perfume, soap, and shampoo calmed me and let me focus my attention fully on her. She was biting into my shoulder and I didn’t stop her. She could leave a permanent scar for all I cared. I fucking deserved to feel as much pain as she was and I knew this was nowhere close to her experience.

Ray was breathing heavily and I felt her hand on my dick, guiding me up towards her pussy. I shook my head and pulled my hips down away from her. She stopped biting me long enough to get her lips to my ear, “Please fuck me, Daddy,” she whispered as she moaned.

I stopped resisting and let her guide my dick into her. I kept rubbing her clit, groaning against her ear, “Gia, let’s show Mr. Jones how to get my baby crying in the best way.”

I felt her smile against my neck as she gasped and nodded. Her pussy clenched on me and she started rocking her hips down onto me and back to Ray, causing him to grasp her hips as he groaned loudly. I looked her in the eye and watched her looking back to Ray as she moved her lower body against us.

She looked determined.

Ray’s hands moved up her sides until his hands grasped her tits and pulled her body back to him harder, making her moan and rock her body over us both more urgently.

My finger slicked her little clit back and forth and I pushed my dick up into her cunt faster. Her body trembled in pleasure as she whimpered and carefully moved herself to fuck us, meeting our thrusts in a rocking rhythm with her own hips. I put my free hand on her jaw and held her face toward me, so I could look into her eyes as she came on our cocks with a gasping moan and shuddering body. Ray grunted and moved his hands back down to her hips, thrusting hard into her. She yelped and fell forward onto me as he came deep inside of her ass.

Gia leaned down to me and kissed me hard then moved her lips to my ear and whispered, “Fill me up, Daddy.”

I grabbed her hips and thrust quickly up into her as she whimpered and rocked her hips firmly against mine, squeezing my cock and ensuring every last fucking drop of my thick creamy cum was inside of her cunt. She looked back to Ray, “Remember what I said?” she asked.

He nodded and pulled his dick from her then promptly lowered his lips to her cunt as she lifted herself, pulling my dick from her. I raised up and watched him licking and sucking my cum from her tight little pussy. His tongue teased her clit and made her moan then his lips moved up to her ass and continued cleaning and sucking cum from her as she maneuvered so she could kiss me while his tongue plugged her ass.

When he finished he got up and looked at us both, “Just remember, before she leaves, she’s mine again, so work on stretching her cunt so I can really fuck her.”

I lifted Gia off of me and retrieved our clothes, helping her get dressed before taking the camera and going back down to our room together.

When we got inside I pushed her up against the wall and looked her in the eye, “What did you say to him while I was out of the room?” I asked.

She smiled, “That I know he’s been boning his step-daughter on the side.”

“Wait, what? Why did you let him fuck you if you had something like that on him?” I asked, a little furious.

“Because I didn’t have proof of it. I told him if he left it at fucking my ass for now, and ate the cum out of me, both yours and his own, then I wouldn’t convince his stepdaughter to report him to the police. I lied. I told him I saw her crying when she left his office the other day and she told me he’d been blackmailing her into sex for years. He went white as a fucking sheet, so now I know that it’s true,” she said.

She leaned up on her tip-toes and kissed me then grabbed my shirt in her hands and tugged gently, “I’m still going to convince her to go to the cops. I’m going to wait until just before I leave, though. He’s not going to get a chance to fuck me again because I fully plan on helping her get proof he’s been forcing her into fucking him now.”

I grabbed her ass and started to lift her up but she winced, “Are you okay?” I asked.

She nodded, “Just hurt more than I expected it to. I’m due to stream again tonight,” she said sadly.

I smiled, “How about tonight I make things a little more special. Camera trained right on your pussy with me sitting out of sight, rubbing your cunt and making you cum over and over again, stretching your hole for them, letting them see just how quickly you go back to being a tight little thing,” I said.

She nodded, “I think I’d like that, just…can we stay in the room today? I don’t think I feel like being around people right now.”

“How about another bath with me?” I asked.

Gia smiled, “Yes, please,” she said sweetly.

“You stay here and get naked, I will be right back, baby girl,” I said. I reluctantly left her to go down to the lobby and requested some items to be sent up to our room. I paid for it all in cash with generous tips for discretion.

When I got back to the room, Gia was lying on the bed, naked, and very much asleep. I watched her sleep while I waited for her gifts to arrive.

Source: reddit.com/r/Erotica/comments/i40mjn/careless_whispers_part_eight_anal_dp