Dirty Dolly's Pimp

I Pimp Out My Sister And Our Pops Doesn't Mind

This is my attempt to explain how it all came about; how I came to be dirty Dolly's pimp. I get thrill chills just remembering the events ...

Pops and I were doing the dinner dishes together. Dolly was out overnight at her best girlfriend's place. I wanted to talk to my Pops about a very important matter but I was nervous about broaching this particular subject with him. I wondered if I could be arrested for simply voicing an idea; a long held fantasy actually. I took a deep breath and went for it,

"Hey, Pops? You got some time to talk or rather to hear me out?"

Pops eyed me quizzically as he dried his hands on the dishtowel,

"Yeah, I got time, what's up, son?"

Now that I had his attention I wasn't really sure how to word what I wanted to say; what I wanted to propose. I went with blurting,

"I want to pimp Dolly out to my friends."

Pops was silent so long I wondered if he was deciding whether to punch me out. He finally spoke softly,

"I see. Care to elaborate and tell me how you thought of it and how you plan to carry it out? Does Dolly know what your plans are for her?"

I was well and truly stunned. Plans? So far all it was was a far-fetched idea that if I was honest with myself I'd been half-hoping Pops would shoot it down and tell me I was a sick, perverted, creep and to stay away from his baby girl. His wording made it sound like he wasn't thinking any such thing,

"Well, no Pops, she doesn't know. Nobody does; I've never said it out loud before. I guess I kind of expected you to freak out on me for even admitting that I want to do that to her."

Pops grinned humorlessly,

"Yes, well, I suppose if I was an honorable man I might have - but I'm not. Some of my own friends and even co-workers have made comments to my face and behind my back about what they'd like to do to Dolly or have her do to them. My lack of outrage at their crude language and allusions about my daughter surprised me, too."

My mouth hung open slightly in wonder,

"What're you saying, Pops? You'd actually let me?"

He answered with a question of his own,

"Do you mean to do this even if she objects, which I'm certain she will?"

I steeled myself for his reaction as I nodded resolutely,

"She won't find out until it's far too late to put the brakes on."

Pops eyes gleamed in immediate understanding,

"Date rape drugs then, hmm? How will you stop her from turning you in? Just playing devil's advocate here."

I was starting to feel the first glimmer of optimism that I might actually get to do it and get away with it,

"Blackmail her with naked pictures of herself until she participates seemingly willingly, then get pics and vids of her servicing my friends while lucid and unrestrained; she'll be hard pressed to prove she didn't consent. She'll cave, I know she will. She'll be my whore to pimp out to whomever I want - no plans to ever accept money for her services Pops; I just want control of her."

I held my breath fearing I'd said too much; gone too far. This wasn't just my Pops; it was her Pops too.

The way he looked at me I couldn't quite determine how he'd taken in what I'd said. He shrugged,

"So why tell me about it? Do you need something from me?"

I chewed my lip hesitantly,

"Sort of. I need you to either stop me now or look the other way when shit starts to happen; just in case it doesn't turn out right - I don't want to get you into any legal trouble, Pops."

He laughed out loud,

"I don't need protecting, son! Matter of fact I was thinking we could get further with it by working together. You mind if I'm a silent second in command?"

My eyes surely bulged,

"Pops! Are you serious? You want in on it? We're really gonna do this?"

My Pops nodded and grinned,

"As I said your friends aren't the only ones who'd like to have Dolly service them! I've no intention of taking charge or stealing your thunder - this is your deal, Adam, but yes I'd like to help you out however I can; including but not limited to finding new customers for Dolly to service. What do you say? Thirty seventy partners?"

If I hesitated even a second before eagerly shaking my Pop's proffered hand, I wasn't aware of it. I was beyond elated. Pops and I set to hashing out a detailed plan right away. Dolly would be completely blindsided and powerless to stop us; while I was about to become even more popular with my friends. The title of Dolly's pimp had a much nicer ring to it than that of merely Dolly's brother.

One thing we agreed on was that when it came time to blackmail Dolly, it was imperative she not know of Pops involvement in order to gain her co-operation ; the threat being that she must co-operate or the pics would be anonymously e-mailed to dear old Pops. We picked my best friend, Martin Alcazar, as our third co-conspirator in the plan to drug, undress, pose with Dolly in compromising ways, rape all her holes and record and photograph it all. Martin nearly creamed his shorts at the idea that he would get to undress and play around with Dolly's naked, unprotesting body.

We wanted to make it as easy, on ourselves, as possible, to get her naked. To achieve that, Pops threw a small pool party ensuring she'd be in her swim suit when the drug kicked in. Pops also wanted to cover our asses in terms of Dolly suspecting being drugged, so he invited her to drink alcohol (which she'd been pestering him to allow her to do at home, anyway, since she'd turned 19, even though the legal drinking age was 21). He faked her out though, by personally making all her drinks himself and simply flavoring them with rum baking extract. Dolly believed she was becoming tipsy. Then, Martin slipped Pops the date rape drug to put in her fourth drink and her tipsy feeling was no longer psychosomatic. Pops laughed good-naturedly and sympathized with her sudden fuzzy headed feeling and unsteadiness in standing, citing that sometimes booze can hit you like a ton of bricks like that just when you think you aren't that drunk. He asked Martin to help her to her room. We knew the drug was doing the trick when Dolly wasn't even coherent enough to object to being alone with Martin in her bedroom.

Martin returned to the party a few minutes later and covertly gave us the all okay. His all okay signal meant she was out cold and the cameras were in place. We'd tried to suggest he be the one to strip her without us being there but though he admitted that was tempting, he didn't trust himself to stick to the plan if he was all alone with her naked and unconscious. We completely understood.

Pops remained at the party as his alibi since the pics would be time-stamped, while Martin and I pretended to leave knowing we had friends who would gladly alibi us if need be. Instead of leaving, we broke into my Pops' bedroom at the side of the house. The party noises covered us. Then we snuck upstairs to my sister's bedroom. My stomach gurgled in nervous excitement that the wheels were finally being set in motion to make my fondest wish come true in short shrift. Martin and I grinned at each other and high-fived when we saw her passed out on her bed, in nothing but her sexy, yet entirely too modest bikini.

I got behind the video camera double checking the angle and that both a master and a copy tape would be recorded simultaneously. Martin changed clothes, put a mask over his face and slipped on a pair of blue latex gloves. I plugged in my brand new laptop next and adjusted the web-cam settings. We'd decided to also go live with the revealing and raping of her body. Already people we're logging in and cheering us on in text. The live feed was also being picked up and recorded by Martin's home computer, further serving as his back-up alibi. The theory being, in case Dolly remembered being alone with Martin briefly, that Martin couldn't be in two places at once; both molesting Dolly and be logged in at home just recording it like everyone else.

Martin gave the signal that he was ready to begin and I pressed record on the video camera. Martin decided to tease the viewers a little before getting down to business, running his hands all up and down her body, groping her tits through her bikini bra then rubbing and finally roughly gripping her crotch. The chat-room was a flurry of activity with encouragement, suggestions and impatient demands. I couldn't see his face but I knew Martin was grinning. He propped her up so that the viewers could get a good look at her face. I reached around the laptop screen careful not to block the web-cam or jar it's position, and I hit ctrl V to paste a previously typed block of text from the clipboard into the chat window. The text read,

"Hello, all you horny bastards! This is Dorothy "Dolly" Monroe - you can call her DD just like the size of her tits, or if you prefer Dirty Dolly! She is 19 years old and as you're about to find out - she's a true red head. We're live from the sexiest state in the U S of A - enjoy the show!"

The chat-room exploded in excited text. I noticed a few viewers excitedly claiming to know who she was and I hoped it was the truth. Martin gave in to the ensuing demands of the viewers without any further teasing. He got her bikini top off faster than I had expected he might and suddenly there they were; my sister Dolly's juicy 36 double D naked tits. Martin indulged chat-room viewers demands to grope them, pinch her nipples and squeeze the double D's tightly together creating even more incredible cleavage. I was on such a high, I barely remembered to take the digital stills with the camera in front of my face.

Viewers were soon demanding the promised proof she was a true redhead. Martin promptly obliged. It was a little trickier for him to get her bottoms off without obstructing the views for too long a time, but within moments she was completely nude. I took a peek at the current viewership numbers and grinned. Over four hundred people were tuned in and the numbers were rising. Martin unhesitatingly, spread Dolly's legs open. He moved her ankles up nearer to her ass and let her knees fall naturally apart. The position partially parted her cunt lips and her little man in the boat peeked out at us. The sight of my sister's goodies exposed, coupled with the knowledge that a lot of strangers were looking at her and lusting after her swelled my chest with a pride I'd never experienced before.

Martin had brought along a few props for the show which he began to use in conjunction with his own fingers. He held up nipple clamps questioningly and got a majority nod of yes from the viewership. None of his props were vetoed. Before long her nipples were clamped, she wore a ball gag, her cunt lips were more widely spread open and secured with clamps, there was an anal plug in her asshole and Martin was actively fucking her cunthole with a variety of things which included his fingers, a dildo, a light bulb, an empty beer bottle, and a hairbrush handle. Finally what we had hoped for happened; the viewers started to demand that Martin fuck all of her holes with his cock. He left the light bulb and ass plug in her but removed her ball gag. He turned her head toward his crotch, pulled out his hard dick and rubbed the head all over her face before slipping it between her still parted lips. He squeezed her cheeks together with one hand and began skull fucking her.

The chat-room was going wild. Martin was breathing rapidly by the time he stopped to move on to fuck her pussy. He repositioned her ankles over her shoulders and secured them to her headboard with nylon stockings. He removed the cunt lip clamps and the light bulb, gesturing to the viewers that her lips were not immediately returning to the closed position while he also showed off the glistening pussy juice all over the light bulb.

I adjusted the video camera angle to catch the action of his cock pistoning in and out of her cunt. My eyes widened when I saw blood on the base of Martin's dick. Martin stilled when he noticed it and looked at me. I had been spying on her monthly record-keeping of her period, so I knew for certain she wasn't on the rag and Martin really wasn't so well-endowed as to make her bleed. None of the objects he'd just used had a surface that could scratch her on the inside so we both realized at the same time that Martin had probably just popped her cherry.

The viewers apparently suspected the same thing. I carefully typed confirmation that the blood was indeed cherry juice. If the chat-room had been wild before it got really wild just then.

Martin got really excited by the knowledge she'd been a virgin and resumed jack-hammering her. It was a really exciting scene to take in. Every thrust made her tits jiggle.

After a few minutes, Martin slowed down and pulled out though he still hadn't cum. He removed her ass plug and loaded up both her asshole and his own cock with lube. Her asshole was still gaping slightly from the plug which made penetration easier for Martin. He didn't pump but a half-dozen times before he groaned in ecstasy and his hips jerked forward as his load of cum shot deep inside her rear fuckhole. He quickly pulled out so the viewers could see his cum continue to spew out his cock head and onto her cunt, her stomach and her tits. The viewers were loving it.

For the grand finale, Martin inserted his dirty dick back into Dolly's mouth, several times until with her reflexive involuntary swallowing she had cleaned off every last trace of cum, cherry blood and ass juice from his gradually softening dink. He then made a point of scooping some of his cum shot leaking from her gaping asshole, with two fingers and smearing her face especially her lips with it. Martin put a loose blindfold on Dolly, loosely secured her wrists to the headboard and loosened but didn't remove her ankle bindings. It was imperative that she awaken alone and be able to wriggle free without calling for help. I took another last capture of her with the digital camera. I stopped the video camera recording and ended the web-cam view.

The chat-room erupted in a mixture of protests for the show ending and gratitude for the show having been shared at all. I typed out return gratitude for their viewership and offered to upload for right click saving, the final still I'd just taken of Dolly naked, exposed, bound, gagged, freshly fucked in all three holes, and covered in cum. A large number of viewers patiently waited while I did that. Most of those exited as soon as I'd done so but a few even stayed long enough to profusely thank me once they had the still image on their own PC's.

Martin took off his mask and gloves and changed back into his other clothes again. As soon as I'd finished uploading the rest of the digital stills to a remote site that we'd set up in advance, I shutdown the laptop. We looked at each other, let out a victory yell and high-fived before finishing setting the scene we wanted her to find herself in, when she awoke. Pops had provided us with a generic typed note that read,

"Thanks for the graphic pics and videos of our intense fucking, dirty Dolly. I won't tell your Pops if you won't. ;) I'll be in touch. Sssssshhhh! Press play to view your copy of us fucking. I'll show you the pics later but only if you're very obedient. Wonder what your Pops would think if he ever saw them? Be obedient and he won't. Nefarious regards from your new boss - DDB! P.S. Keep an eye out in your in-box and spam folders for for an e-mail with attachments from an address beginning with "dirtydollysboss" and confirm receipt - or don't and hope like hell your Pops' e-mail account has excellent spam filters in place and that he doesn't check that folder."

I would have loved if the note had mentioned her virginity but we hadn't known about that when the note was typed out. I smiled to myself; there'd be other opportunities to rub that in her face.

The thought of rubbing something in her face gave me another idea. I dug through her purse and applied lip gloss to her cum covered lips, delighting in the knowledge there'd also be cum transfer back into the vial. I then squeezed her cheeks until her lips puckered almost like an opened mouth kiss, and pressed the kiss to the note itself.

Martin and I left her tied to the bed, naked and blindfolded, surrounded by all the props Martin had used on her and the copy of the tape in her vcr with the note propped against it. She would definitely notice it right away, the moment she got the blindfold off.

Now we just had to sit back and wait to see if I knew my sister as well as I thought I did. I was optimistic that I knew her better than she knew herself.

For a week we three took turns sending Dolly pics from that night from the e-mail address referenced in the note. Whenever she was out of earshot, Pops and I laughed about her jumpiness lately knowing full well the reason for it. The video had been multiply copied and distributed anonymously to my and my Pops' friends and colleagues. So far nobody was blabbing.

The site we set up contained her phone numbers and known e-mail addresses as if she had set the site up herself. The site was getting a lot of unique hits daily. Dolly's cell phone and private line rang constantly and sometimes her face would either redden or blanch as soon as she answered.

Pops feigned concern but Dolly always covered with a lame excuse and a phony little laugh. We knew she'd been to the site and was frantically scrambling, trying to figure out who had done all of this to her and how she could get the site removed without Pops or for that matter, anyone else finding out either. We heard through the grapevine that several guys had approached Dolly seeking confirmation that it was her in the chat that night as evidenced by the pics on the new website. She denied it of course, vehemently, but none of them believed her.

On the tenth day after her initiation as my whore, I sent her instructions from the e-mail we'd been using to communicate with her, that she was to meet a john and service him or suffer the consequences. Unbeknownst to Dolly the john was an old colleague of our Pops'. He gleefully reported back to us that she had obeyed to the letter. He gave us the name of a good friend of his to set her up with next, who'd be amenable to being videotaped and posted to the internet. Dolly delivered an outstanding performance.

Mere days after the new video had been successfully uploaded, I confronted her, pretending to have stumbled upon it while surfing. She tried to explain but by the end of it, I told her she was obviously a whore by choice and that if she wanted my silence, as well as that of this alleged mystery boss of hers, that it would cost her. She spat at me and tried to attack me but Pops interrupted. I threatened to spill the beans about why we were fighting but she stopped me and covered again. I agreed to her version of things in front of her but told Pops every detail later. We had a good chuckle over it.

As soon as Pops had left Dolly and I alone again, she wanted to know my terms for my continued silence. She freaked out when I told her I wanted all my friends to gang bang her while I watched/recorded it and that they were to have repeat access anytime anywhere. She told me to go fuck myself and I threatened her with showing Pops the video I'd discovered on the net.

We video taped her gang-bang party with my friends later that week, with her knowledge - complete with smiles into the camera and touching herself on request. We got rid of all evidence of our involvement in the drugged rape, including taking down the website and putting up a new one with the apparently consensual acts content. When we were sure there was nothing left tying us directly to her rape and blackmail, we cornered her at a party and forced her to watch her newest tape with us (which not everybody there had yet seen or even knew about). Her humiliation was complete and she was mine to control.