Hiring Some Help Online – My gf, Lisa, and I have been going out for over four years. Starting about two years ago, I became fascinated by the idea of cuckoldry. Through stories on this blog and elsewhere, I would learn about various forms of cuckoldry and daydream about Lisa becoming a domineering cuckold mistress. However, I felt that it was wrong to somehow try to manipulate Lisa into becoming something that she wasn’t already. Consequently, I never revealed my cuckold fantasies to her and we’ve had a pretty vanilla relationship for the past couple years or so I thought.
Overwhelmed by my fantasy, I scoured online for services which could give me a taste of the cuckold lifestyle that I would never have with Lisa. About a year ago, I stumbled upon a site for an online mistress who catered to men’s cuckold fantasies. There was a catch though. In order to make the fantasies feel real, she had a consensual blackmail policy with all her slaves. The way it worked is that the slave would pay her money and in exchange, she would send him humiliating tasks that emphasized various aspects of cuckoldry. If the slave could not accomplish the task or tried to cheat, she would reveal some incriminating information about him online or directly to his friends or spouse.
I knew it was risky but I was also eager to experience the excitement this arrangement would provide. To begin, I called her and received details on how everything would work. To start, I had to fill out a document providing all personal information for myself and Lisa. My online mistress knew Lisa’s phone number, where she worked, where she lived… I even had to include a picture of her. All information about myself had to be verified with copies of my driver’s license and tax forms. There was no way I could fake it. As the final nail in the coffin, I signed a very official looking contract that committed myself to the whole arrangement for 6 months.
As material for blackmail, I had a recorded webcam session with my mistress where she made me strip, describe my humiliating fantasies, put on a pair of Lisa’s panties, etc… If I ever failed to complete one of her tasks, I would risk having this video sent to Lisa or posted online for all to see.
Each time I received a task from my mistress, I was extremely excited. For the first couple months, the tasks we’re quite humiliating and I had to send pictures of myself completing these tasks as evidence to my mistress. The worst one was when she made me buy a dildo and send pictures of myself putting it in my mouth and ass. All the tasks became further blackmail material for my mistress.
For the fourth task, my mistress ordered me to send her more information about Lisa including her work schedule and any naughty pics of her that I had. Some of those pics are attached. I was very hesitant to do this but my mistress quickly pointed out that if I did not do as she said, she would send all the blackmail material directly to Lisa and even call her to explain how pathetic I am.
On the fifth month, I did not receive a task at the usual time from my mistress. I called to see what was wrong and she told me that she had be working hard on a present for me and that my task would have to wait for two weeks. As punishment for my lack of patience, I was not allowed to have sex with Lisa or jerk off for the next two weeks. It was awkward a couple times avoiding sex with Lisa but I don’t think she picked up on anything strange. At the end of two weeks though, I was extremely excited but also very worried about what task my mistress had in store for me.
When I finally received her email, I was floored by what it said.
Thank you for all the information and pictures of Lisa. This was extremely helpful when crafting this month’s task. Since you are too much of a sissy coward to tell Lisa about your cuckold fantasies, I thought I should help her find a real man without your direct involvement. I’ve taken all the information you’ve given me about Lisa and posted an ad online. In the ad, I say that I am a close friend of Lisa who wants to help her get some. I say that her boyfriend (you) is pathetic and cannot provide her true sexual satisfaction. Consequently, I need an attractive pick up artist to try to get her to cheat on you. I received over 50 responses.
For each guy who responded, I sent them your naughty photos of Lisa and told them when and where she would be at work. The only stipulation was that they could not tell Lisa about this ad or the arrangement. Also, if they were successful with Lisa, they would need to send me proof.
And would you believe it, with two weeks and over fifty guys trying to pick up your girlfriend, one of them actually succeeded. His name is ______. This is what he looks like (pic). He is way more buff and handsome than you and his cock is 4 inches longer than yours. I bet Lisa will enjoy that.
As proof of his success, he send me a voicemail left by Lisa on his phone. Listen (mp3). She was apparently thrilled to meet him at her store and has agreed to meet him for drinks at his house tonight. At the end of the message, she also mentions that she’d love to see his hot tub. I wonder why she said that?? She must want to get naked in it with him!
So what’s your task… your task is to go to this address _______. Don’t park right in front like an idiot. This is his house. You should see when Lisa arrives there tonight and better yet, when she leaves. Report back on this experience.
I parked around the block from his house at 8pm. It was a really nice house and I was surprised he lived there alone. Around 9pm, Lisa pulled up. She parked right in his driveway. She knocked on his door and was immediately let in to the house.
At this point, I was nearly hyperventilating with a mix of dread and sexual excitement. This was exactly what I wanted but not how I ever imagined.
Lisa did not leave to get back into her car until 1am. She spent 4 hours at his place and her hair was wet and she was wearing different clothes when she left. I didn’t know what happened inside that house but I could only fear the worst.
Two weeks later, my mistress sent me her final correspondence noting that our 6 month contract was up. She said that she was very happy knowing that I got exactly what I wanted.
Lisa and I continued to go out for another few months but we eventually split apart. It became increasingly apparent that she was seeing someone else though I never brought it up and I’m pretty confident she never thought that I knew anything.
I’m currently looking for another online blackmail mistress to lead me on another wicked adventure but haven’t found anyone yet.
mahmiss21 @ gmail.com