He told Gia to get dressed up and told me to come up with a camera ahead of Gia so I didn’t know what she would be wearing. We did as we were told and I’d be lying if I didn’t consider trying to kill him before Gia got there. I was too afraid he’d get the upper hand and end up hurting Gia because I lost my temper.
When I got to his room he looked so fucking smug, “Decided to share?” he asked.
“No,” I said, “she didn’t feel like she had a choice.”
He shrugged, “But she did have a choice, she just made the easy one.”
Yeah, I wanted to fucking kill him. He made small talk and acted like it was the most fucking normal thing in the world. Then he laughed and looked over at me, “See, I’m even helping you keep your wife from castrating you. You won’t be leaving her alone with me at all, you’ll be right in the room, watching the whole time.”
I felt sick.
Gia knocked on the door and he looked to me, “Start recording as soon as I open the door,” he said.
I got up with him and walked over to the door, camera in hand. He pulled the door open and Gia was in a casual summer dress with her eggplant moto-jacket over it. The dress was simple, a white babydoll style dress that made her look way too young for my comfort. Her hair was pinned up, twists and curls carefully curated to look messy and a bit bohemian.
He put his hand on her waist as he guided her inside and closed the door behind her. She wore simple jewelry and her makeup was soft and natural looking. I was uncomfortable recording him with her looking like that. She reminded me too much of the sixteen year old her, the last version of her I saw before that night in the strip club. If not for her body and hair color remaining the adult version I knew, I would have grabbed her hand and pulled her out of there. She was twenty, I reminded myself. She would be twenty-one in two months.
I had no claim on her. If she wanted to fuck my boss, I couldn’t stop her. I could just do what I was told and record him with her to keep my marriage from falling apart.
Ray pulled her jacket off of her shoulders and I noticed she looked almost empty as I watched her expression through the camera. She let him kiss her neck as he stood behind her and she let him grope her tits through the thin white material of her dress. Gia said nothing as he guided her over to the big, floor to ceiling window in his room. I just recorded, gritting my teeth and trying to avoid clenching my fists and breaking the camera.
He sat in the chair facing the window and pulled her up onto his lap. His voice was gruff, “You are just a hot little slut aren’t you?” His hand trailed over her cheek and down her shoulder, untying the ribbon at one shoulder, then the other. He looked towards me and grinned as he pulled the top of her dress down to reveal her soft creamy breasts with hard pink nipples. She hadn’t worn a bra.
He looked back to her and put his hand on the center of her back. I wasn’t a small guy, but Ray made me look small. His hand nearly covered her back. He was seven foot one, over two feet taller than her, and he outweighed her by over a hundred and fifty pounds. She looked small next to me, but she looked like a god damned fairy next to him.
Her tits were a healthy handful with slight spillage for me and for him he could easily cup her fully. I recorded him fondling her, playing with her nipples, tugging and sucking on them. She looked uncomfortable as his hands slid up the back of her legs, lifting her dress with them. He pulled her down onto his lap by her hips and slid his hands further up her body, pulling the dress off over her head.
She had on a small thong and he ripped the sides to pull the fabric off of her. He groaned as he looked at her body. His fingertips touched on the small of her back when he placed his hands on her hips. He licked his lips and tipped her chin to look up at him, “I always thought it was camera tricks making you look so small,” he said.
His thumb moved down to her clit and started rubbing her, she glanced to me and he grabbed her jaw and forced her attention back on him, “No, sweetheart, you’re mine right now, don’t look to him for approval. Now kneel in front of me and put that mouth of yours to work. Get me nice and wet if you don’t want your cunt and ass to hurt,” he growled.
Gia’s hand trembled and she slid down his legs until she was on the floor in front of him. I’d never seen Ray’s dick before, so I didn’t know what to expect. Proportionately I wouldn’t be surprised if his dick was twice what mine was, and I wasn’t a small guy there either, but I was hoping things went the other way and his dick wasn’t proportionate with his overall size. I think she was scared too because she fumbled with his zipper a little.
When she got it down he lifted his hips and she pulled his pants and underwear down his thighs, uncovering his cock, which was hard as a rock. He was thicker than me, but he wasn’t double my size. Her cunt and ass were both extremely tight. It was a big enough difference that I was afraid he’d hurt her. I know what she was at or nearly at her limit with my cock and even half an inch difference in thickness could make it very painful for her, and he was probably a little more than half an inch thicker than me.
I looked at her and shook my head, wanting to beg her to not go through with it.
But she started stroking his cock, pulling his foreskin back and forth over the head. Then she took him between her lips and expertly started sucking him off. Her hands fondled his balls and rubbed the base of his dick as she started choking on him almost all the way down. She had to stop and catch her breath before trying again, determined to get him as tightly into her throat as she took me.
She was struggling with his thickness.
Her eyes watered, her stomach tensed and for a moment I thought she might throw up, but she fought through until she got her throat opened up and worked him in. He groaned and held her there, her fingers curled on his leg and I was about to intervene when he pulled her off of his cock roughly, the wetness of his dick leaving her throat made me cringe. She fell to the floor coughing and gasping for breath. He started to pull her up to him and she cried, “Wait,” her voice was strained and her cheeks were red, “please wait?” she begged.
He seemed annoyed but gave her a minute until she composed herself. She started to go back down on his dick, but he shook his head. He got up and led her over to the bed and sat her on the edge of it, “Open your legs up wide,” he said.
She did and he licked his middle finger and started rubbing her clit. She was wet already and he guided his finger over her opening, rubbing back and forth across her a little roughly until the tip of his finger pushed into her and made her yelp and pull back a little. I was still recording them.
Ray groaned and closed his lips over her cunt, tonguing her clit and working his finger into her. He pulled back and chuckled, “Christ she’s tight,” he said.
He looked up at her, “Hold yourself open for me,” he said.
She reached down and put her fingers on the edges of her hole and pulled her pussy lips open a bit. The pink spread excited him and he plunged his finger deeply into her, curling it in and rubbing along the front of her pussy as his tongue went back to her clit, pushing hard on the sensitive spot inside and outside until she grasped his head and pulled his mouth tighter to her. She came hard, a rush of fluid coated him and he hungrily lapped her up while he carefully pulled on her cunt and worked his other ring finger into her as well. She was whimpering and arching her back as she lay on the bed. I could see her little cunt being penetrated by two large fingers.
He wiggled them and alternated pushing in and pulling out with each one. Then he started opening her hole up by pulling and stretching her opening. Her gasps and squirming hips and legs made me uncertain if it felt good or hurt, but I know I was fucking hard as a rock while filming him forcing her cunt to open enough to take him.
He fingered her like that for a few minutes, her juices coated his fingers and her opening and I wanted to lean down and stick my tongue in her while he held her hole open, but I refrained and instead watched him do just that. His tongue darted in and out of her and she moaned and whimpered as it flicked around her internally. He looked at me and motioned me over closer. The camera picked up the sheen of her wetness on her softly reddened flesh and the audibly slick penetration of his fingers pulling and thrusting in her.
Then he stood up and positioned his cock at her hole. She cried out as his head pushed into her. Her hands were grasping the bed covering and her back arched as he fucked her hole with just the very head of his dick. Her body pushed in and pulled with each motion. Recording it and watching it were both horrifying because I loved her and intensely arousing because holy fuck was she stretched around just the mushroom of his cock head. The underside of his head was clearly visible through the shape of her skin as he pulled back and pushed in. Her cunt clung to the him and I wasn’t even sure he could pull out fully without effort.
Then he pushed himself a little deeper, his shaft was a little thicker than his cock head, into her and she screamed and tried to pull away. I moved to intervene and he looked at me sternly, “She’s fine, keep recording,” he groaned.
I looked to Gia, she was breathing heavily but she looked at me and nodded. Tears were streaming down her cheeks. She was not fine. But I didn’t intervene. I let him push deeper into her as her body shivered and she gasped. Her eyes got wide and more tears flowed from the outer corners. I know she was hurting and trying hard to make it look like unexpected pleasure rather than pain.
“Christ I’ve never had a pussy this soft and tight before,” He groaned with a laugh, “she’s actually hurting my dick she’s squeezing me in so tight.”
He pulled his dick from her and I noticed blood dripping down her. Her entire body was trembling slightly. I put the camera down and pushed him away from her, “Don’t fucking touch her again,” I yelled.
Ray laughed as he noticed the blood on his dick, “Did I break your toy, Dean?”
Gia grabbed my arm, “I’m okay, it’s fine,” she said, her voice was still strained and tinged with pain.
I turned my head towards her and said, “No. It’s not an option anymore, it never should have been an option to begin with.”
Ray smiled, “It’s fine, I got my dick in her mouth and cunt and I still get to tell Katherine you took her sister’s virginity on camera. Only now I get to tell her you let me fuck her a little too but her baby sister’s tight little body couldn’t handle my cock. Maybe I can show her the video so she knows you were recording me with Gia…saw her in pain and just kept letting me fuck her.”
Gia grabbed my hand and pulled me back to her, “Dean, stop. I said it’s fine. It only hurts a little, I’ll get used to it,” she said.
My brow was crinkled in worry as I turned to look at her. Her eyes were red, tears were drying on her cheeks and it was killing me. I kissed her and whispered, “I don’t want you to do this.”
“I know,” she said softly.
I cupped her cheek and looked her in the eyes, “I’ll leave Katherine if you don’t do this.”
She shook her head and looked to Ray, “Would you be satisfied just fucking my ass?”
Ray tilted his head slightly, “Wouldn’t that hurt more?” he asked.
She shook her head, “It’s better trained, like my mouth, from toys on the cam show,” she said as she glanced at me.
Ray nodded, “I can work with that, sweetheart,” he said, “but if we do it this way, I want another go at your cunt before you finish the internship. Maybe Dean’ll stretch you out some with a little more use. I know he’s not that much smaller than me.”
She nodded, “Okay.”
Ray looked to me, “I don’t have any lube here, I suggest you run back to your room and get some for her.”
I wasn’t supposed to leave her alone, but I nodded and put the camera down.
“And bring one of those tripods up with you,” he yelled as I headed out the door. I was gone for ten minutes max. I ran the whole way and the longest part was waiting for the elevator. If not for the alarm warning on the stairs, I would’ve just ran the whole way.
Source: reddit.com/r/Erotica/comments/i3xr7r/careless_whispers_part_seven_blackmail_size