Careless Whispers (part nine) [full body massage] [bath] [light bondage] [orgasm denial] [over-stimulation] [genital display] [Hurtful interaction]

When room service came, I let the guy in. He brought the cart into the room and saw Gia spread out naked on the bed, very clearly sleeping. He tried not to stare, but I just looked at him and smiled. I wouldn’t have been able to look away either. I slipped him another tip and before he left I told him about her website. He was blushing brightly and his dick was clearly hard as his snug uniform left very little room for his own discretion.

I closed and locked the door to our room and went back over to the cart. None of it mattered ultimately, but I needed to at least try to make it up to Gia for letting my boss blackmail us like that. I should have just called Katherine and confessed to having an affair with her little sister. I’d take on the fallout of it. I would’ve been the bad guy if they needed to me to be. Instead, I took the coward’s way out and let Gia take on the burden of our actions.

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.”

Published
Categorized as Erotica Tagged

Careless Whispers (part seven) [Blackmail] [Size difference] [Age Gap] [Dubious Consent]

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.

Testing the Limitations of Her Programming [Sex Stuff]

“This, dear fellows, is Gaia,” his voice boomed through the room as a group of men in business suits crowded around the small booth. He sought funding to create more like me. I began as a joke between him and his middle school friends. Why date when you could create the perfect woman? Then he actually set out to accomplish that.

His name was Jack and I adored him. He was thirty-two years old and brilliant beyond anything. I stood in front of this crowd for him. I displayed myself for him. I obeyed him. At the moment I scanned the crowd. In front of me was a group of men ranging in age from early twenties to late sixties or so. Each one wore a business suit and seemed to be lost in the paperwork more than paying attention to me.

I looked to Jack lovingly and he nodded, the crowd was becoming disinterested in words and needed to see action, so I began my part of the presentation. I stood up and walked down the steps and positioned myself just in front of the crowd. Many of the men towered above my five foot four frame and I could feel my heart racing. It wasn’t my heart, I do not have one, it was my processor, it was at risk of overheating so I took a few deep breaths to cool it. My breasts rose with each deep breath and the men became fixated on me.

Careless Whispers (part six) [Caring] [straight sex] [cunnilingus] [pretending to sleep]

When I realized she wasn’t settling down, she was still horny and wanting, I picked her up from the bed and carried her into the bath. I ran the bath full of warm water and climbed in with her. We spent over an hour in the water with me gently washing her body and hair, soothing her aching muscles and kissing her softly.

Gia fell asleep in the water and I let her sleep for a while, sitting with her to make sure she was safe, but the water was getting cold again so I let it out and carried her back to the bedroom. When I laid her down on the bed I noticed her clit was still swollen, so I leaned down and kissed it. Flicking my tongue back and forth then leading it down into her cunt. She squirmed on the bed, waking up slightly.

I climbed up the bed and kissed her, whispering, “Go back to sleep and let me give you some good dreams.”

Careless Whispers (part five) [First time Anal] [Virginity Loss] [Over-stimulation]

The week dragged by and, as expected, Katherine was against Gia going to the conference with me and my boss, Ray. The boss is the one that actually talked her into it in the end. He insisted, actually, stressing that this conference was an excellent networking opportunity for Gia and her getting a foot in the door this early could mean the difference in a long job search after college or having offers waiting on her to graduate.

Katherine talked to Gia, who basically said she was either going with her sister’s permission or without it, and Katherine relented. My wife pulled me aside and said, “Don’t leave Ray alone with her, at all, or I will castrate you when you get home.”

I promised Ray would not be left alone with her, even for a minute. I sat between Gia and Ray the whole trip. It clearly annoyed Ray, but I bluntly told him my wife’s ultimatum and he backed down and gave up on his hopes of more than a professional experience with her on this trip.

Careless Whispers (part four) [Anal: wife] [Anal Play: sister-in-law] [Fingering] [Blowjob]

Katherine didn’t seem to notice anything amiss and the day came to an end without a fuss. I managed to sneak a couple of gifts into Gia’s room without anyone noticing, though I wondered if she would find it or not. I was restless all day, wanting a reason to be in my study late so I could check to see if Gia did a show or not, but I never came up with one and had to curb my wants by begging my wife to let me have her ass. Katherine had a nice and tight cunt, but I was trying to mimic what Gia’s body would feel like and my wife’s ass was her tightest hole.

I pulled out last minute and pushed Katherine onto her back, cumming on her clit and mound as she glared at me, “Now I have to actually shower,” she whined.

I smiled, “I can come clean you up,” I offered.

She shook her head and pushed me away, “No, you have to go to bed so you can make sure Gia gets up in the morning after I take the kids to school so you two aren’t late to the office. Are you sure it’s a good idea to just bring her in without talking to the boss first?” she asked.

Careless Whispers (part three) [Masturbation] [Fingering] [69] [Face Sitting] [Cum Play]

When I went into her room, she was laying in the bed on her side with her laptop closed up on the bureau. I quietly moved over to the bed and knelt down beside her. She was biting her lip and I tugged on it, pulling it free of her teeth. Gia had such soft pouty lips that it felt almost impossible not to kiss her, but I resisted and looked her in the eye as she closed her eyes and made a tiny moan.

I stroked my hand over her cheek and down her neck, moving the blanket away from her enough to see that she was still naked. I ran my hand over her body, kneading her breasts like I’ve wanted to since that night in the club. I stopped when I saw that she had such a needy look in her eyes and I slid my hand lower. Her own hand was between her legs, so I put my hand on her hip and rubbed it gently as she worked her clit.

She looked painfully restrained in not being able to moan.

I leaned down and whispered to her, “Will it help if I kiss you?”

Careless Whispers (part two) [Cam] [masturbation]

I felt like I was going to throw up when I watched her sway her hips as she walked into my living room. Gia put her bags down by the coffee table when Katherine came out of the kitchen, pulling her youngest sister into a tight hug, “Ooh! It’s going to be awesome having you here with us for the summer,” my wife cooed.

Gia was bouncing excitedly and I could see the sway of her unrestrained tits as her crop top lifted enough to show the swell of her breasts. “Were you going to inform me of this?” I asked my wife as I gathered Gia’s bags to take to our guest room.

“It was last minute,” she said dismissively, “An internship fell through back home, so Gia’s going to intern where I work for the summer. Oh, it’s been so long since we’ve gotten to spend time together. Every time we’ve gone home lately you’ve been away at college!” My wife complained.

Careless Whispers (part one) [Stripper] [Blowjob] [Cheating]

The last time my wife and I went out of town we got into a fight and I ended up at a strip club a few counties over, a college town full of beautiful girls that needed a quick buck for school supplies in the middle of their winter break.

I was mesmerized by this one particular girl that I kept catching glimpses of.

I’d only seen her from the back, but she was this petite little thing that had a knock-out body. Her hair fell in soft curls down to her ass, each curl a different jewel-toned color. An emerald colored thong clung to her ass and hips, showcasing the curves of her impossibly pale flesh. Her waist dipped in just above her hips, creating the perfect place for hands to hold her while she got fucked. Even the way her legs were stretched and strained in her silvery heels was stunning.

I wanted the dance from her so I talked to a waitress. She approached the girl and I watched her push her hair behind her ear and nod. She walked off and I watched her ass sway as she headed towards the private rooms. The waitress came back and led me to the room the other girl had disappeared in.