Just Once, Never-ending
By Rusty Zipper
Story description: A son blackmails his mom to do a distasteful task that snowballs into a gooey mess and escalates.
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DAY ONE: COMPROMISING POSITION
I blackmailed my mom.
I did it on a whim when I caught her in a compromising position. At the time, it was also an effective way to circumvent her livid disposition that arose from my duplicitous judgment.
It all began when I entered her bedroom without knocking. She was laying on the bed wearing a robe, but the bottom half was parted.
Naked from the waist down, her thighs were widely opened.
With a vibrator in hand, she was pleasuring herself and was moaning with her eyes closed.
I had my phone in hand and did something stupid. Well, perhaps it wasn't so foolish now that I think about it, I guess it depends on perspective.
I took a picture of her masturbating.
Not a smart move if you forget to turn the flash off.
Yeah, a burst of light in a dim room did alert my mom to an intruder.
Her eyes immediately popped open and the reaction was what you'd expect.
Her knees snapped together while she scrambled to close her robe and she yelled, "What the fuck, Chad!"
"The door wasn't locked," I replied.
The noise produced from the vibrator in her hand made for an awkward conversation.
Her face blushed as she franticly twisted the bottom to turn it off.
Tossing the device under the covers, she retorted, "And you didn't have the decency to knock?"
Her angry chastisement stemmed more from embarrassment, but she was right. I should have been more conscientious for her privacy and been a gentleman.
Buffeted by guilt, I said, "I'm sorry. I'll knock next time. I'm going back to my room."
I turned and placed my hand on the doorknob.
"What did you do?" my mom said with an accusatorial tone.
I turned back to look at her, my expression was guilty of a travesty.
I've learned by experience from my girlfriend that women have this unusual ability to read a man's mind based on his countenance. Moms are even more efficient at reading their sons like they have a built-in guilt detector. In this instant, circumstance, a flash of light, and a cellphone with a camera that was noticeable in my hand made it easy for her to deduce that I'd done something deplorable.
Her eyes narrowed, she headily rasped, "I'm your mother, how could you?"
Truly, my stomach did wrench at that specific moment. I was caught committing an appalling act and my back was against the wall.
Then she demanded, "Delete that picture right now!"
Perhaps it was the tone of desperation in her voice that triggered me.
"Why would I? Maybe I'll send it to your friends. Perhaps I'll email blast it to your church group. Wouldn't that be embarrassing?"
She huffed, "You're blackmailing me?"
Okay, for clarity, I wasn't thinking of that when I threatened her. It was primarily to get her off my back. She put the idea in my head and my thoughts became perverse. When my mind drifted to the gutter, I began thinking of how far I could push her.
"Yeah, I'm blackmailing you," I replied.
For a moment, she stared at me with a red face and a slack jaw.
She then said, "You can't be serious. You'd do that to your mother?"
I sheepishly smiled and replied, "I have a picture of you with your legs spread and a vibrator half-buried in your hole. That gives me leverage. How desperate are you to keep it out of circulation?"
"Chad, what do you what? A game console? A computer for college? A new car? Tell me and I'll pay for it. Then you'll delete that damn picture from your phone."
I said, "How about a hand-job and you don't stop until I pop."
It was obvious that I'd taken her off-guard. She began stuttering and then coughed to clear her throat.
With a furrowed brow and her eyes narrowed on me, she exclaimed, "Did you just say you want me to jerk you off?"
"Yes. Until I ejaculate. I have an explicit picture of you, my payment should be of equivalent significance."
"Oh hell no. I didn't raise a perv. I'm your mom, that's sick. You've lost your mind. You're playing me. Pick something reasonable," she replied.
I decided to bluff by placing my hand on the doorknob. I then said, "It's no joke. You're not taking me seriously. As soon as I step through this door, I'm bombing the picture out. I'll let you explain it to your churchy friends."
"Chad, this is ridiculous."
I replied, "Okay, I'm out of here," as I opened the door and took one step out.
"Wait," she blathered out in desperation.
I closed the door and turned back to face her.
She glared at me and said, "You'll delete the picture in front of me when I'm done?"
I kept my expression blank, but I was nervous and shocked by her reply. Her last statement was more than a consideration and I must admit it intrigued me.
I said, "Of course I will. I'm not out to hurt you."
"You need to swear that this will never be discussed. Not one fucking word to anyone. Do you hear me?" she demanded.
"Do you think I'm crazy? My lips are sealed, I promise."
She rose to her knees and mumbled, "I can't believe I'm agreeing to do this."
It was as if she read my mind again because I was thinking the same damn thing. Frankly, I was scared and wasn't so sure I could go through with it.
I was about to say that I was teasing her and would just delete the picture.
Then she said, "Chad, drop your pants and underwear. It'll be easier than yanking it from the fly."
Yeah, my mom said that. Perhaps in a more casual tone than expected and now I was the one taken off-guard. I was her son and it wasn't like she hadn't seen me naked before. Although, I wasn't a little kid taking a bath and much had changed since then.
"Are you going to do it or not?" she said.
I stuttered, "Y...Ye...Yea...Yeah, give me a second."
My mom gawked at me and I was unnerved by it.
At this moment, I felt like the one being blackmailed. I'd somehow backed myself in a corner and felt obligated to follow through with the obscenity.
After I placed my cell phone on the dresser, I hesitantly removed my shoes, trousers, and boxers and then stood there like a fool staring back at her.
Truly, she wasn't smiling, and she had no desire to do this. Seeing her son naked from the waist down wasn't sexually arousing to her, it was the opposite. She was repulsed by the idea and it showed on her expression, but she oddly took the blackmail to heart and felt coerced to follow through. She was being tasked to perform a sexual act on her son it distressed her.
She huffed and then said, "I'm not stooping on a dirty floor. Crawl up on the bed and get on your knees. Don't make this difficult for me or I'll change my mind and take my chances."
I'd gone this far, and I admit I had a legitimate curiosity as to whether my mom would fondle me or chicken out at the last instant. For that matter, would I even allow her to do it or would I freak out and find myself in an awkward predicament?
I clambered up on the bed and shuffled forward on my knees until I was five feet away and facing her.
I could have ended this now by telling her the blackmail was a sham to see how far she'd go, but when I saw her busty cleavage and a shadowy nipple from the parted dangle of her robe it kind of jinxed that idea and I kept my mouth shut.
She grimaced and then whined, "Chad, I'm your damn mother and your penis is hard already. What the hell?"
Well, in truth, it didn't get rock solid until she approached me which is why she made that comment. Acquiring an erection when my mom came within proximity was difficult to explain and somewhat shameful.
I replied, "I don't control my dick. What do you want me to say?"
"You shouldn't have a boner is all I'm saying," she exclaimed.
Yeah, her response required me to give her a "what the fuck," look so I did.
I replied, "Are you going keep appraising my rigidity or do the deed?"
She returned the same expression I had given her a moment ago and mumbled, "This is so wrong."
She reached out and clasped the shaft in her right hand. As she began slowly yanking my dick, her face expressed distaste and she turned her head to avoid looking at it.
When she felt my member twitch and throb in her hand, she grimaced and muttered, "Oh my god, you're turned on by this."
I said, "It's obvious and the point of this activity. Remember you can't stop until I ejaculate. I'm going to edge this for as long as possible."
She pivoted her head back and glared at me. She then heatedly said, "You're going to do what?"
When she first touched my dick, I'd thought I'd be as squeamish as she was, but having her hand wrapped around my shank had a calming effect and my arousal inspired a vulgar image in my mind. Since she wasn't matching expectations, I decided to up the ante by manipulating her.
I replied, "You're not performing with much enthusiasm and my dick knows it. I'm going to try and hold off the urge just to humiliate you. There is a way to speed this up, but you won't like it."
She huffed and then replied, "Jerking you off was our agreement. What are you suggesting?"
"If you put it in your mouth and looked up at me with pouty eyes, that would damn sure speed up the process."
"You're asking me to suck your cock?" she retorted.
"No. I'm giving you an alternative that will shorten the time you'll have to spend with that nauseated expression on your face. It's your choice."
"Chad, that's taking this too far. Not happening."
"Then keep up your lackluster tugging. I'm sure I'll feel the need eventually," I replied.
She snapped, "Oh, hell no, I'm not spending all day on the bed fondling your penis. This needs to end."