Betting On My Family - Cover

Betting On My Family

Copyright© 2016 by Bartleby T

Epilogue: Because My Editor Demanded It

Coming of Age Sex Story: Epilogue: Because My Editor Demanded It - Ben is out of sorts after moving to idyllic Orange County with his family and is coerced into the illegal and dangerous sex trade. As a crisis at home ensues and difficulties at work intensify, Ben’s family and a motley crew of co-workers are forced to make difficult choices before their new fairy-tale existence comes crashing down around them.

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   mt/Fa   ft/ft   Mult   Teenagers   Blackmail   Coercion   Drunk/Drugged   BiSexual   Heterosexual   Fiction   Humor   Incest   Group Sex   Anal Sex   Double Penetration   First   Oral Sex   Prostitution  

Dear Diary, I’ve finally seen it all. I realize that I’ve been saying that a lot lately, but I think that this series of events takes the cake.

I’d thought that sleeping with my own step-son would be the most shocking thing that I’d ever take part in, but the most shocking part of it was how much I enjoyed myself. I could never tell it to his face and retain any sort of parental authority, but I have to admit that Ben fucks like a damn stallion, and in a perfect world free of taboos, guilt, and bigotry, I’d have him filling me up each and every night.

Sometimes get a little wet when he walks around without a shirt on. It’s so embarrassing. If he only knew what I was thinking, I’ve no doubt he’d be eager to drop the rest of his clothes and take me in every room of the house. God knows, I’ve dreamt about it. Jesus, this is unhealthy. Maybe I should seek therapy.

His young tight body is beautiful, as much as it weirds me out to admit it. And his penis ... Christ almighty, I fucking love his penis. Clarence had always been a good lay, but his son’s intensity surprised me and his long thick HARD cock just hits my spot in ways that I didn’t think were possible. And he fucked me so hard, and so many times ... I’d never seen such stamina.

The bet was naughty. I knew it wasn’t necessary but I couldn’t help it. At the time, it was the only way I could justify letting that sexy young stud pound on me for 8 hours. Good Lord, I need help. But so often, I just need dick a lot more. But that’s old news news. I’m getting off track here. There are plenty of earlier entries about my longing for the forbidden cock, and how that forbidden cock made me feel warm and tingly each time it pumped me full of cum and ... STOP IT.

So. I’ve already described the details leading up to our standoff with Dana and how I was forced to take charge and kick out the boys. I’m sure Ben was disappointed that we never got to have our scene. God knows I was at the time. But it needed to happen this way.

It was better for Ben to take his stand, and it was better for me to finally get a little closure over what happened between us so long ago. And it was better for Bridget, surprisingly. I might need to worry about that girl’s proclivities down the line and who she chooses to venerate. She seems almost as enamored with Dana as Dana was once enamored with me, and look how that turned out. It’s too early to say whether her feelings are a good or bad thing though, and I need to start letting her make her own decisions. At least I think so. I wish I was more sure about these things.

Strangely enough, I think the person who benefitted most from this was Riley. That girl really had some pent up rage for her mother. Gorgeous girl, that Riley. Such poise. I can see why the girls like her. Her beautiful young form makes me ache in remembrance of how I used to look that way, but I don’t think even I had a body like that at sixteen.

She’s not as buxom as my daughters, but she’s one of those girls that just has perfect symmetry. From her cute perky breasts to her surprisingly toned little butt, there is just no flaw about her. She’s even more beautiful than Dana was around her age but they’re obviously family. So much that I couldn’t help wanting to get a little bit more familiar like I was with her mother. Definitely need to seek therapy...

Once the boys left the room, Riley snatched away the metal cock that Dana and I had named after Clarence back in college. I couldn’t believe she still had the thing after all these years. I knew that I should probably assert some level of control but Riley seemed on the warpath, and she seemed so fierce in her nudity that I didn’t want to interfere ... and I kinda wanted to see what would happen. Dana scoffed at the prospect but she seemed to acquiesce a bit after I threatened to chain her to the bed.

She didn’t acquiesce enough for Riley though. We still ended up chaining Dana to the bed. Victor’s twisted sex rooms were already equipped for the task and Dana didn’t feel the need to fight against the four of us. Pity that. It could have been more fun that way. Riley wasn’t after fun however. Riley seemed after vengeance.

Before Dana could lodge any serious protest, the young girl climbed onto the bed and straddled her mom, sitting on her stomach while she adjusted the strap-on to her liking. Dana seemed pretty put off by it, but we couldn’t hear what she was saying due to the ball gag. Oh right, didn’t mention that part. Riley was only too eager to utilize all the gear available to restrain her mother which went beyond just the chains. And I thought my family had issues.

I almost started to get flashbacks seeing her strapping on that chrome dick. She looked so much like her mother once did in that moment. Even if I did most of the fucking in the relationship, it always gave me pleasure when Dana bent me over our dorm room desk and blasted me from behind. I can still hear the creaking of the wood scraping along the linoleum floor, and I remember the thumping from the people who lived below yelling at us to shut up. I only screamed louder when they complained. And Dana, as result, would give it to me even harder. Memories...

Riley was cut from the same cloth. I don’t know what was happening between them, but her anger was pretty evident as she pried her mother’s thighs apart, and slipped Clarence home. She didn’t take it slow or give Dana any time to adjust, she just screamed “How do you like it!” and rammed her hips home and started taking her mom like I’ve so often taken Lexi - hard, rough, and fast. Like me, Riley seemed the dominant type. Maybe she can take care of Lexi in Pittsburgh when Ben needs a breather. I can’t imagine Lexi would turn her down. I don’t know if I would either.

It wasn’t over quickly. Victor told us shortly after that this was sufficient to fulfill our end of the bargain. Riley was a minor and if he was looking for dirt, there was certainly nothing more damning that a video of her being taken by her own daughter. But his words didn’t stop Riley, if anything, she was just getting started. At one point she even leaned forward and started to choke Dana as she wailed away at her pelvis. Dana’s face went so red, I was almost forced to intervene. I hate to admit that I got pretty wet watching it. I’ve always been attracted to Dana, and this was like watching a young Dana go nuts on an older Dana. But Riley knew how to work that dick better than her mother ever did. Definitely the dominant type.

I couldn’t tell if Dana was cumming or not, but there was certainly a lot of flailing legs, clenching of muscles, and screaming into gags going on. It was difficult to tell if they were of pleasure or pain. The two sensations have always been rather intertwined in our cases so I imagine that it was a bit of both, but even I didn’t know what to think when Riley pulled out and spit on the chrome cock like so many male actors do in movies. Beads of perspiration were apparent on her face and her breath came heavy as she pushed the cock down an inch and lifted her mother slightly by the butt-cheeks. The the screaming began anew as Riley started fucking her mother up the ass.

And to think I was wet before.

This continued for another ten minutes, a rather long time, until finally Riley’s hips started to slow, the little sex bunny running out of juice. She slapped her hips home a few more times, much harder than necessary and finally announced. “Fuck it, I’m done” before rolling off the bed to the side and unsnapping her harness. But she didn’t untie her mother. Instead she tossed the cock to Bridget, who had taken position on a couch and was actively masturbating to the sight. “Here, go nuts,” Riley said, before stomping off and out the door. Dana rolled her tired-looking eyes. Kids these days...

Normally, I would have chastised Bee, but with everything that had been going on, one daughter fingering herself was laughably tame in comparison. I had her fuck her step-brother for crying out loud. Besides, she probably didn’t even realize what she was doing with those drugs inside of her.

Oh, the drugs...

That whole afternoon after Dana and I squared off was a tense one. I was very VERY upset with her about how she casually used my daughter to trap a known rapist. I’ve since calmed down, because Dana’s judgement is always fucking terrible, but I was angry enough at the time to want some revenge of my own. In addition, ever since Dana had arranged me to get gang-banged by frat boys, I’d been waiting for a chance to even the scales. I took up Clarence from a giggling Bridget and strapped it on myself. Dana needed a little more punishment, and I wasn’t going to give her a spanking. Well ... not only a spanking.

I felt a rush of nostalgia as I crawled back onto the bed, and Dana pulled at her chains, begging me to remove the gag. I did so, because there was nothing that she could say to stop me regardless. She didn’t try to stop me though, but instead glanced from her handcuffs to the steel dick I was about to impale her with and chuckled. “Just like old times, huh?” she said.

“Not quite” I replied, and lowered the cock down to her asshole again. Dana and I had never done anal in college, but when you when you want to put someone in their place, there’s no better hole to punish than the ass. It’s just so dehumanizing, despite how wonderful I think it feels.

Dana’s screams on my go around were definitely pleasurable, but I gave it to her hard enough that she would feel it the next day. God knows I was still feeling it myself after Ben fucked like four loads into my ass the night before. Jesus, it makes me blush to see remarks like that written on a page, but whatever. What’s done is done.

Maybe Dana and I both belong in jail, maybe not, but I definitely gave it to her like she was my prison bitch. Riley had been faster and more energetic, but I lengthened my thrusts to make sure all eight inches of that cock were up her ass before withdrawing. And I hammered her for a good half an hour. I had almost as much pent-up aggression as Riley.

Eventually though, the woman below me ceased to seem a monster and instead looked like that young mousy shy girl I fooled around with in college. I’m usually not one to get lovey dovey, but I was emotionally strained from the past 24 hours, and I soon found myself laying on top of Dana, kissing her and squeezing her breasts while I slowly worked that big metal dick in and out of her asshole. It was pretty hot. I got even more excited when I turned to the side to see Bridget still frigging herself with a desperate look on her face. I no longer wanted to chastise her. As messed up as it was, I wanted her to join in.

We slowly got to talking. This was the point when we decided on the daughter swap. Dana was sure that Riley would be better off without her for the time being, especially as it was still up in the air how she was going to take care of Georgio, or whatever that fuck’s name was. She didn’t want Riley anywhere near that, and she certainly didn’t want her in her employ at the time. It was an easy decision on my part. I knew Riley had already become friends with the rest of the kids and she would be happier with siblings for a change.

Letting go of Bridget was harder, but there was something in the way she looked at Dana that told me that I needed to let her go and let her find herself. Later, after I’d stripped off the cock, I was surprised that Bridget wanted a turn as well, and then I knew it for sure. She didn’t fuck Dana. She made love to Dana. Seeing the two of them go at it plucked at my heartstrings even more, as Bridget has always looked nearly identical to me at that age. It was like watching myself experimenting with Dana all over again. I knew what I would have wanted if I was her. I knew I had to let her go.

When Sid finally shut off his camera, it was a like a spell had been broken and everything suddenly felt surreal, foolish, and unbelievable. Riley had been gone for a while and Bridget gave me a hug before taking off, saying that she would die if she didn’t find some snacks soon. Dana still sat on the bed, finally unshackled, massaging her wrists and looking uncharacteristically sheepish. She was looking at the spent chrome dildo beside her and rubbing her thumb across the etching at the base which read “Clarence.” And then, she surprised me.

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