The Whip Or The Vibrator Ch. 01

I heard more sounds in back of me. The bottle being popped open, what sounded like skin being rubbed. What was going on? Then I felt it. Duke's knees were between my legs. He'd picked me. He had just enough room to spread them a little, what with the confined space and the ankle chains. It was tight, but I figured later they'd designed their setup for this. I couldn't think like that in the moment.

This was exciting, and terrifying. I felt Duke's skin against my legs. His pants must have been down around his ankles. This was only the fourth man I'd felt against my skin in my entire life, and the first since my husband. It had been so long, that I'd forgotten what it felt like at all.

Duke lowered himself onto my body, crushing me into the mattress. I felt his cock rubbing against my butt cheeks. He grabbed my hair to pull my face up a bit, and caressed my cheek. His hand was slick. Was that something from the bottle? Lube, it was lube!

"We've both been dreaming of this moment, haven't we? Just like this."

He let go of my hair. I felt his body shifting back there. He grabbed my hips, pulled them back as much as the restraints would allow, which wasn't much. The chains on my wrists were pulled taut. Them I felt him lifting off my body and lowering back onto it.

His cock! I felt his cock! The tip was pushing down into my butt cheeks. His body pushed down onto mine as he put his hands back there to spread out my butt cheeks, and then he shifted a little to get just the right position, and his cock pressed against my asshole.

Oh God, he was going to butt-fuck me! No! I've wanted this for so long, but I don't want this.

With his cock in place, Duke put his hands back at his sides to push off me a little, and focus on getting his cock in there. Then he started pushing, slowly, just barely. It didn't hurt that he had gravity on his side. Wait, where were his fingers? He's supposed to finger me first!

"Yep, I know what you're thinking", Sado-Chick said. "He's supposed to finger you first, right? That's what you've been reading in all those stories and anal tutorials all these years. Sure, that's normally the way to do it, but it's not absolutely necessary. This way is more pleasurable to Duke. He'll just let gravity do it's job, take his time, and open you up slowly. It takes longer, of course, but we've got time. Unless there's somewhere you need to be, of course."

I tried to squiggle out of this, but there was no room for that, and Duke just pressed down tighter to keep me in place. I think he liked it. I could swear his cock got even harder. My anus started giving way. It hurt. It hurt like hell. I'd never had a single thing up my butt before, not so much as a thermometer or a suppository. I screamed into my penis-gag, really loud. Well, the gag kept me from getting much volume out. I screamed and screamed some more.

"You go ahead and scream, honey, as much as you want", Sado-Chick said. "I'm keeping a watch out. If anyone shows up, I'll quiet you down. So scream your brains out. It'll make this even more memorable for the both of you."

Duke moved his left hand up to grab my hair again as his cock continued to press down into my asshole. It was hurting more every second, but also feeling sort of good? I don't know. And then he stopped. He just held it there as he gripped my hair. He leaned up to kiss my cheek.

"Ah, this is a big moment for you, baby", Sado-Chick said. "He's got the tip in. How's it feel, Duke?"

"Ohhhhhh mannnn, it is so tight in there. I think she might hold the record for time to open up. Damn, but I love middle-aged virgin ass."

"I know. So hard to find these days. Well, honey, here's where the fun really begins."

And with that, I felt the pressure. He was pressing back down into me. With my sphincter just barely opened up, his cock was drilling down there, millimeter by millimeter. So slow, but God, it hurt like hell now. The pain was excruciating.

"Here" Sado-Chick said, "You won't want to miss this."

Sado-Chick was talking to Kit-5. She turned Kit-5's head to face me. I didn't really notice it at first as I screamed into my gag with my face buried in my mattress, but then the pain suddenly subsided. Duke was all the way in my ass. His cock had drilled down as far as it would reach. His body was completely pressed down against mine. I was sweating like a pig now. My body was slick from it. I twisted my face out of the mattress for air, and looked into her eyes. Kit-5 was right there, staring back at me.

Duke let go of my hair to push himself off me. I felt his cock being pulled out of my ass. Noooooo. I'd gotten used to it. I yearned for the fullness of feeling in there. Then he pushed back down, nice and slow. It just felt right to be filled up again. He did this a few more times, and then the fucking started.

Duke's grip on my hair kept my face facing Kit-5's. I stared into her eyes as the fucking went on. I tried to look away, but kept coming back to her eyes. She did the same. The feeling of being butt-fucked was uncomfortable enough emotionally to begin with. No matter the circumstances, there would have been a part of me unable to relax, to just ease into the moment. I'd been suppressed for too long. Even though my brain now knew that there was nothing wrong with anal sex between too consenting adults, my body had never had a chance to catch up to it. I still felt the shame of being taken back there, even though it was such a massive turn on as well. But to have to endure this moment with other people watching...

Sado-Chick just held her phone the whole time, filming us. She even yawned at some point. Kit-5's body was a part of this too. I was scrunched up against her, and felt the side of my body rubbing against hers the entire time.

What was Kit-5 thinking? What was she feeling? Fear? Of course. Disgust? Was she looking at me like I was some sort of cheap whore? I was just some middle-aged women she'd never even met before, and her introduction was to watch me take it up the ass for the first time. I couldn't help my arousal, I just couldn't. I was sure she could see it in me. She could certainly hear it. My screams had been replaced by new sounds. Was it cooing? What? I don't think I'd ever made sounds like this before. Well, I'd never made any sounds with a penis gag in me, that was for sure.

Compassion? Empathy? Did Kit-5 feel sorry for what I was going through? Sure, maybe that too. How about envy? Did she feel that too? Did she want this too? She must have on some level. She wouldn't have come to this airport otherwise, right? She wouldn't be in this van right now if she didn't want a stranger to tie her up and fuck her sweet ass until he came in it, and then make her suck him clean. Yep, she was turned on all right. I could see it now. Her body was also starting to sweat a little. Against all reason, she wanted that cock up her butt just as badly as I did. Her body was shifting. If she could have masturbated, she would have.

I closed my eyes. The fucking was getting intense. He was pounding the shit out of me now (pardon the expression, considering where his cock was doing the pounding). Oh God, had I taken a decent shit today? Yes, I had, right after coffee in the morning. Thank God for that. Hopefully there wouldn't be any mess back there. I didn't think he was using a condom, so Duke might have some mess to deal with regardless. Duke wasn't fucking to savor the moment and make it last. He was fucking to cum. I guess they wanted to get on the road. After the pounding reached jack-hammer levels, he stopped, just froze. I'm not sure what I felt back there, but after a minute of time being frozen, he collapsed onto me. Then he pushed back off of me, and got up. The Sado-Chick tossed him a towel and a bottle of hand-soap. I heard squirting, toweling off, and then his pants being pulled back up.

"How was it?" Sado-Chick asked.

"Heaven. Just pure heaven" Duke said, "So tight, just the right combination of fighting it and giving in. And thank God she had a decent shit today. No mess to speak of. I left a nice deposit of cum in her ass."

He leaned down to run his fingers through my hair.

"It'll give her something to think about on the drive, knowing what's swirling around in her ass the whole time."

Then Duke got up, crawled over us to the driver's seat, and started the van. We were off.

My journey had officially begun.