Blackmailer's Web Pt. 01

Dan, a bit caught off guard, glanced away, but then a small grin appeared on his face. "I think he wasn't and still isn't great at being a partner, you know, in every way."

She let out a little hiccup and nodded. "Yeah, you're right. He was bad."

"I wonder how often he made the whole process... enjoyable for you. If you know what I mean," Dan teased, earning a playful scold from her.

"Daniel! You're getting too personal now. I'm definitely not discussing that kind of stuff with you," she said, taking another sip of wine.

He glanced lightly at her neckline as she took a sip. At this time of year in early winter, the skin on her tits was especially pale, but that only made them prettier and more appealing. "Yeah, I'm sorry. I just can't imagine how you lived with him for so many years. It must have been very lonely for you."

"Yes, it was. And I hardly ever enjoyed the process. If that's what you wanted to hear from me."

Dan smiled and took a seat. "Hardly ever?"

"Maybe three or four times over all these years. He was always more concerned with pleasing himself than me. Typical Frank. Goodness, why am I even talking about this? You're taking advantage of tipsy Mom, you cheeky boy. I won't say anything more."

"Sorry, Mom. I just think you deserve someone better than Dad. You deserve someone who treats you well. I'm just worried about your happiness."

"Don't worry about me, focus on yourself, "she took another sip, her boobs slightly jiggling behind the nightgown. "So, have you found the right girl?"

"No, not yet. I'm looking for a pretty, loyal, and kind-hearted girl. Someone as amazing as you, but, well, it's a bit challenging."

"That's very sweet, Dan," Nancy blushed, appreciating her son's sentiment. She was touched by his words but also felt a bit uncomfortable.

"Listen, Mom. What if... you know, we made another video? We could make more money. Just one last video. Mom and Son."

She looked at him, mulling over his words. "Well, I..." her response was cut short as the front doors buzzed again. Jack stood beside her. He entered the room wearing his jacket and gave them a stern look.

"Mom, don't believe a word he's saying. He's just trying to deceive you. It's crystal clear to me."

"I have no idea what you're talking about," Dan replied.

"I can handle things on my own, dear. But thank you. Why don't you go change, and I'll take a short break. I think I've had a little too much wine," Nancy said, standing up with boobs forward. Her dress pulled up and Dan got a good look at her slightly pale hot thighs and legs before she covered herself and headed upstairs to the bedroom.

"Jack messed it up again," Dan sighed. "Was she going to agree or not?"

She'll agree one way or another. The last few weeks Dan had been taking money meant for the house payments, keeping it for himself. Their debt will grow and she would have to accept his offer on the video.

He had already put all the money aside, including the money for the bathroom video, to pay off all debts at once. "I'm still gonna get you, Mom. You can't escape me."

===

All night long he thought about the next step.

Step 4. Make her feel like a woman again.

This step involved the first serious intimacy. He'd been sitting on various websites, learning how to properly pleasure a woman with fingers. It was horrible; he couldn't imagine pulling something like that off with his Mother. And the step didn't provide the details of how to pull it off.

He studied everything until the wee hours of the morning, trying to figure out how to locate the G-spot and bring a woman to orgasm. "Yeah, it's going to be hard without practice."

He spent countless nights at the computer looking up every possible tip. And so the days and weeks went by.

"I can't give up," he pictured lovely Mom in her sexy purple nightie, pictured her coming to his room, ready to do THAT (despite his lust he still wasn't ready to say the s word, when talking about Mom). "We'll do it, Mom. We have to," he whispered falling asleep right in from of the monitor.

Someone was knocking on the door and he woke up. The morning light dazzled. "Dan, can you come downstairs? We have something important to discuss" said Nancy.

The bills kept piling up, and their Mother took a break from work to face the mounting debt. This morning she gathered them around the table and addressed the issue directly. "We're in trouble, boys. I had time to think and I keep wondering if going back to Dad might be the only solution to deal with everything."

Immediately, Jack responded, "No! We don't need him."

Dan, silently thinking that maybe Jack had some usefulness, agreed, "For once, I'm with Jack. We'll find a way to get through this, Mom," he gave her a meaningful look and she seemed to realize what he was up to.

Relieved by her children's support, Nancy sighed, "Fine."

Jack, determined to contribute, said, "I'll work even harder, Mom. For our sake." He planted a kiss on her cheek and left the room.

Dan, sitting quietly across from her, observed Nancy nervously fiddling with her fingers. "His money won't cut it for us... What was that you mentioned about the video?"

Dan yawned and smiled, "Video? Are you ready for a new one? It's going to be harder this time, Mom."

"How much harder? I already guessed you got us into a weird and gross venture. What you said about "exploring mother-son relationships" doesn't make sense. I'm not stupid and figured it out."

"First of all, Mom, I just want you to know that I'm not thrilled about what we have to do either. I assure you it won't affect or change our relationship in any way. We'll handle it, move on, and forget about it. I promise," Dan said earnestly, reaching across the table to hold her hand.

She only sighed tiredly and asked. "Just spit it out, Danny. What do we need to do?"

"We need to do a hand job video."

Nancy pulled her hands away in shock. "What?"

"But our faces won't be seen. It's only once and we'll get the money. We'll be able to pay off our debts..."

"Danny. Listen to yourself! That kiss between us was already too much for me, and now you're suggesting...suggesting this... I can't even bring myself to say it out loud."

"We can just do it and move on, like I said. We're not crossing any lines, Mom."

"It sounds to me like we're crossing some pretty huge red lines, Danny. This is over the line; I can't do that. We can't. I don't want to hurt our relationship."

"But you've already done it. That time in the bathroom. Did our relationship change in any way after that?"

Nancy gasped, covering her mouth in shock. "How can you even say that, Danny? I wanted to forget about it... I was drunk, and I made a mistake."

"We didn't do anything wrong, Mom. And it was insanely good. I enjoyed every second of your touch. It doesn't ruin our relationship in any w... Mom?"

She rose, leaving the room.

"Damn it. You fucked up, Dan. You fucked up so badly."

Chapter 7: "I KNOW, DAN". 5 MONTHS LEFT.

In the weeks that followed, Nancy seemed distant and preoccupied, growing apart from Dan and increasingly spending more time with Jack.

One day, Dan entered Jack's room while he was away, searching for the pregnancy magazine.

After a brief search, Dan finally held it in his hands. "He still keeps it in the same place where I found it last time. Moron."

Flipping through the pages, he discovered the very page Jack had been fixated on. The pages were sticky, which he found quite unpleasant. "Gross," he ran a quick glance over the text.

"The Best Days for Pregnancy. Women are most fertile at the time of ovulation (when an egg is released from your ovaries), which usually occurs 12 to 14 days before your next period begins. This is the time of the month when you're most likely to get pregnant. Aim to have regular intercourse during the woman's fertile window. Sperm can survive in the female reproductive tract for several days, so having intercourse leading up to ovulation can increase the chances of conception."

For some reason, the thought that apparently visited his brother's mind became interesting to him as well. A shiver ran through Dan's body at the mere thought of it. "Me and Mom? Pregnant? I'm not sure how far this is going to go and if she'll ever let me do it, but... How do I know if Mom is ovulating? Or what if she's already gone through menopause?" Dan rubbed his chin thoughtfully. If only Dan from the past could see him now.

A message from Blackmailer came through on his phone. "Tick-tock, Dan. Tick-tock. Time is ticking."

"I know it without you, asshole," Dan whispered, hiding his phone and magazine. And just in time.

"Dan," he turned around, feeling a sense of déjà vu as Nancy appeared in the doorway. "What are you doing here? Again?"

"Nothing. Just dropping by."

"Are you sure you're not taking anything without asking?" she sighed. "Sometimes I wish that your weird actions were due to money challenges rather than something related to our relationship."

He walked over to Nancy and hugged her tightly, feeling her soft boobs against his chest. "I'm sorry, Mom, for everything; for asking you to do...these things."

"It's okay, honey. I'm not mad at you."

"I didn't mean to hurt you. I just know how badly we need money," he turned, savoring the scent of her hair.

"I appreciate your help. We've received enough money already, and I understand your intentions were good, Danny. So I forgive y-."

Dan rushed and kissed her softly on the lips. Again. This time she tasted salty; he guided his tongue right into the depths of her sweet mommy's mouth and for the first time her tongue instead of avoidance - responded to the gesture. Their mouths melded together, sharing saliva. He was sucking on her saliva, engulfing his tasty Mom, his hands down her thighs, barely touching her ass. He moved up left hand up, gently caressing the underside of Mom's left breast, but right then, she paused and ended the kiss.

"Danny, wait... Can I ask you? Would you like to join me tonight and watch TV? I wanted to talk about something important. About us."

Slightly surprised and expecting a reprimand, Danny, licking off her saliva, said. "Yeah, sure, Mom."

===

They were sitting on the couch, as usual, watching her show.

"I wanted to ask you something, honey. I remember you said you took my picture to your room."

"Uh...did I? Yeah, I guess I did."

"And you said I looked pretty in it."

"Well...yeah?"

"I'm going to ask something important, Dan. Do you like me in terms of attractiveness?"

Dan, confused by this question, looked at his Mom, examining her dark braids, her ample pale bosom peeking out from the robe and bare seductive palm crossed legs.

"What are you talking about, Mom?"

"Do you like me as a woman, Danny?" she said seriously.

"No, of course, I'm don't, Mom."

"Don't think I'm some kind of fool. I'm not clueless. I can see what's going on, and I can imagine what you might be doing with my photo."

"I wasn't doing anything. Ew, Mom. That's gross."

"I'm very serious, Dan. I've noticed that you might have feelings for me that aren't appropriate, and it's important we address this before it affects our family. I think it would be helpful for you to speak with a therapist."

"A therapist? Mom, I thought we were just hanging out and watching TV!"

"Watching TV can wait, but taking care of your mental well-being can't. I'm genuinely worried about you."

"I'm not going to any therapist, Mom! I don't have any of what you're talking about. Close the subject."

"I found my stolen lingerie in your drawer, Dan. When were you planning to give them back to me?"

He felt his face flush with shame. God, how he'd gotten himself into this situation in the first place. "What? I didn't..."

"Don't make excuses. Jack told me he noticed you stealing it. I couldn't believe my ears, but then I found one of my panties yesterday while you were out. How could you do that, Danny? I'm suggesting a therapist for your benefit. It might not seem like a big deal now, but..."

"I don't want to talk about this. Gosh. It's just one big misunderstanding, Mom."

"What do you want me to do? How can I help you understand that this is for the best? Tell me?"

He suddenly had a gleam of an idea. "What do I want you to do? You'll do what I ask you and in return, I'll agree to your.... Request."

"Fine! What do you want? But please, no games, Danny."

"No games. I'll agree to see a therapist if we do the video; if you jerk me off on camera. Jack's is not home and..."

Nancy grimaced in shock. "No! I can't, Danny. Don't make me..."

"I thought you were worried about my health. Just one video, our faces won't be seen. That's it. I'll agree to anything you say. As long as it helps me."

She folded her arms across her chest grudgingly, turning off the TV. Her hands lifted her pale breasts slightly. "Will you promise to seek help if I...do...this?"

"Yes, I promise, Mom."

She sighed. "Okay... Bring the camera."

Dan could hardly believe what just heard. He ran off and came back, setting the camera in the right direction. "I'll cut out the extra noise so we can talk," he turned it on and took the seat next to her, she never moved, folding her legs and hands.

"You forgot... napkins," she said, sighing.

"Sorry," he walked back into the room with the napkins and sat down again. "I turned it on...we can get started."

"Get your...stud out. Quickly! Before I changed my mind," she whispered.

Dan pulled his pants down slightly and slowly, very nervously pulled his cock out. Nancy squinted at him, it was still flaccid. "I can't believe I'm doing this," she sighed.

He wanted to hold back, make it flaccid to convince her to show him her breasts, but he failed the moment her soft hand touched the shaft. "Ughhh," he couldn't resist the incredible sensations and immediately had a full-blown hard-on.

"Ohhhhhh, fuck, Mom," he barely held back a moan, her warm, soft hand encircling his immediately swollen cock.

"Watch your language. If I do this, it doesn't automatically make it okay for you to use strong language," Nancy whispered, moving her long, dark curls away from her face. She gently and carefully pulled the skin taut, it was a million times better than his own hand. His Mom was gently pulling the skin up and down, up and down. Dan had to hold back from cumming immediately. This was going to have to last longer.

"I'm doing this for you, honey," she skillfully used her right hand, her azure nail polish gleaming in the light, Mother's left hand gently rubbing and massaging his balls, delivering unimaginable bliss. She gently parted his scrotum, rubbing his balls while her right hand was actively thrusting in spurts, increasing in speed, then decreasing.

He gasped softly when precum oozed out at the tip. Nancy stopped, picking up the skin at the very tip, and with her other hand wiped the tip with a clean tissue. "Just like when you were little," she whispered, not realizing Dan heard everything.

He was breathing heavily, throwing his arms over the back of the couch, keeping his eyes on her face.

"Are you coming soon?"

Dan only nodded. While there was still time, he prepared to make his move. But he was hampered by the fact that her legs were crossed.

"Am I bigger?"

She smiled with the corner of her mouth. "Maybe." Finally, she parted her legs, spreading them slightly. He could see her breathing heavily as she gradually became aroused by the process. He slowly and stealthily reached for her, his hand advancing into Mom's panties. It was wet. "What the hell are you doing, Daniel?" she whispered.

"Making you feel good."

She wanted to move his hand away but froze. The touches of Dan's fingers stroke her like lightning, "Ughh, dear, please... don't..."

He touched her private area through the azure underwear, exploring Mother's sensitive part, his birthplace. It was a risk he was willing to take. "No, Danny! Stop it...No...Ohhhh."

How did she let it happen? How could she let her son touch her... pussy?

Dan fumbled with her vagina for the first time and began to move his fingers. "Ahhhh, how do you...," she wriggled on the couch, going through different stages of pleasure. Her pussy was so wet and cuddly.

He didn't stop, and neither did she. His balls were shaking from the movements of Mommy's hand, sometimes she squeezed his cock too hard unable to cope with the rush of pleasure. She rubbed his cock furiously, hitting his balls and lifting it up to the tip, milking her own son.

She threw back her head, closing her eyes. "Ohhhhhh, God...ahhhhh.... yeah, that's it." Her hand gripped his cock even tighter, squeezing out the remnants of precum, while her left hand cupped his testicles.

Dan could barely keep himself from stopping because of good she was jerking him off, because of his mother's blissfully soft hand. But he couldn't, he had no right to make a mistake. It was so damn painfully hard to resist and not to cum too soon.

He could see she was close. She shuddered, not noticing the shoulders of her robe falling down, half-exposing her tits. Damn it. He kept his gaze on her tits, the beautiful pink swollen nipples, boobs that quivered with every movement of her hands. It was impossible to hold back at this point.

"Oooooh, Danny!!!" Nancy squealed, closing her eyes and going through her first real orgasm in many years. His hand became extremely wet as her body shook under the strain of orgasm. "Ugh, ughhh, oh my God," she was shaking wildly from the overwhelming sensations coursing through the nerves.

It was about time. Going through heavenly bliss, she thrust even harder and harder, squeezing his dick with all her power.

This time he finally gave in. "Ohhhhhh, Mom, ughhhhhh, FUCK!!!!" he looked at her face, his cock in her hand shook and streams of cum flew out of the tip right onto the couch, her arm, wide spread legs, even her boobs. Dan's whole body was riddled with incredible sensations, pain, euphoria, mixed with a sense of heavenly bliss. He shook his legs and collapsed, completely exhausted and drained, his hand still in Mom's panties. She was still jacking his quivering hot cock, slapping his swollen drained balls. His cum was like lube on her hand.

"What have we...done?" She was breathing hard, not noticing that her dress was wet with bits of cum and drops were rolling down her exposed palm boobs under the dress inside the neckline.

"Enjoyed the process... And had fun."

She finally removed her completely cum-drenched hand and wiped it with a napkin. "No one ever touched me there...I can't remember when was last time when... How did... "

Dan remained silent, savoring his small triumph.

"Now I'm ready to go to a therapist, Mom. Anywhere you want to go," he turned around, watching the droplets of semen still dripping down her half-open breasts onto the dress. The droplets reached the aureole and disappeared right at the spot where her nipple was.

"I'll go. I need to make a call." Nancy stood up slowly, pulling on her robe.

Dan looked at his fingers. "Is that...blood?"