Taking Care of Family Pt. 02

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Tom learns secrets of his mother's best friend.
5.5k words
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Part 2 of the 11 part series

Updated 06/10/2023
Created 06/22/2021
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Chapter 2 - Helping Mom's Friend

After my first year in college, I came home to spend the summer with my mother. She looked and acted much more cheerful than I had seen her in years. I had secretly paid the two months of mortgage payments that she was behind and when she called to verify the monthly mortgage account statement, the company confirmed that she was fully paid up to date. Mom was confused by where the money came from, but assumed it somehow must have been part of her ex-husband's restitution directed by the court. With that news, she was finally able to start making headway on paying off the two credit cards she had been forced to max out before getting a second job that allowed her to buy food, gas for the car, and home utilities.

With her financial burden reduced, she was able to quit the second job and still have a bit of money left at the end of each month. Of course it helped that I was no longer living at home and adding to some of her bills. She had finally accepted that it was time for her to enjoy life more and had joined a group in our community that did volunteer work at a couple assisted living facilities and our local hospital. While she often felt sad for many of the people she met in those places, she could see how much they enjoyed her visits and help, and it made her feel better.

She came to me one morning as I was lying in bed trying to decide whether or not to risk jerking off my morning wood. Fortunately, I was on my side and my bed sheet and cover effectively hid my erection.

"Honey, one of my friends is having some personal issues and I thought perhaps you could help her out like you helped me last year," she said hesitantly. I shifted around slightly to look at her without giving away my hard-on that was quickly dissipating and hoping I would have time to revive it before it went away completely.

"What kind of help does she need?" I asked.

Mom looked uncomfortable. "I think it would be better if she told you herself," Mom answered.

"Okay. Just let me know when she wants to get together and tell me about it," I said with a large yawn. Mom thanked me and closed the door as I briefly considered whether or not to revive my limp cock or just get out of bed to shower and get dressed. I finally stretched and threw off my covers as I rolled out of bed and got ready for the day.

Mom was in the kitchen waiting and told me that her friend would like to get with me as soon as I was available. I poured myself a cup of coffee and asked, "Who is it?"

"It's Carrie," Mom replied. I knew Carrie and Mom had been best friends since elementary school and they had a lot in common. Carrie was a divorced working mom with two kids. She had a very good job that allowed her to work from home one or two days a week, but had been struggling to pay off debts that her ex-husband ran up on their joint accounts and even her personal credit cards before they divorced several years before. When Mom was going through her divorce, Carrie spent a lot of time over here trying to help her out and give some much-needed emotional support. She had a son who was getting ready to start high school in the fall and a daughter who was a year behind him.

Mom thought she was a very nice and compassionate woman who was always making time for others, but lately Carrie had been acting especially stressed about something. The previous day, she finally told my mother in confidence what was going on and asked for any suggestions on what to do. Mom immediately thought of me and offered to ask me to help. Carrie was concerned about my age and couldn't imagine what I could offer to help. Mom assured her I was very mature and had knowledge and skills that she thought would be helpful to the situation.

After finishing my coffee, I opted to skip breakfast and asked mom to let Carrie know we were heading over to see her. Carrie lived just ten minutes away and mom pulled into the driveway of a large home with a very well kept yard. Carrie was obviously looking out for us and opened the front door before finished going up the short steps to the front porch.

"Hi!" she said. "I'm so glad you could come over." She offered her hand and I shook it briefly, noting how small and delicate it felt in my hand. It had been several months since I'd last seen her and I was struck by how much heavier she appeared. She was average height and for the past few years she had slowly filled out into a softer, slightly plumper woman who reminded me of Aunt DJ. However, now she was certainly overweight and showed a noticeable muffin top roll over her waist. Carrie had a very attractive oval face framed by long black hair that went down to her shoulder blades. She had very large, bright blue eyes, a small, turned up nose, and a small mouth with thin lips. As I looked closer, I could see a tiredness in her eyes and lines in her face that made her look much older than she was. Despite her plump figure, her breasts were probably not much bigger than Mom's or Kacie's.

She closed the door and ushered us into a large, well-furnished living room that had a shelf full of pictures of her kids. Walking behind her, I saw her large, round ass moving in a figure eight pattern that I found pleasant to watch. She moved gracefully for her size and I found many of her features to be elegant-looking. As Mom and I sat down on the sofa, Carrie offered coffee which we politely declined. She sat down on a comfortable chair just to the right of me and moved up to the edge so that our knees were almost touching.

She looked over nervously at Mom and then back at me as she considered what to say. "I don't know what your mother has told you about my situation," she began.

"I haven't told him any of the particulars," Mom quickly interjected. "I thought it would be more appropriate for you to tell him as much or as little as you wanted to."

Carrie's hands fidgeted in her lap as she thought on how to proceed and I remained in neutral silence. Finally, she blurted out, "I'm being blackmailed and I don't know who it is or what to do about it!"

I looked at her and then at Mom before returning to meet Carrie's eyes. I could already see tears welling up in them.

"This isn't something you want to tell the police?" I asked.

"Oh, no!" Carrie said horrified. Mom placed her hand on my knee to caution me. "If the police got involved, everything would come out and I'd be ruined!" Carrie exclaimed.

"I see," I said, even though I really didn't know what was going on. "So, why don't you tell me what happened and why you and Mom think I can help," I suggested softly.

"Honey, once you hear about it, you'll know exactly why I think you can help," Mom said with confidence.

Carrie then proceeded to describe how someone had apparently gotten into her computer system and found several very graphic nude photos of her and threatened to release them to her company, her family, and people she knew. "They were made several years ago when my husband was around and suggested that I pose for nude pictures. I agreed and we both found it fun and exciting."

Carrie continued to wring her hands slowly and look down at her lap as she continued. "When we first started, Mike only took pictures of me posing in a manner that I thought would be tasteful, yet sexy and provocative. After a while, he convinced me to pose for racier shots and then pictures of us actually having sex. Back then, we... we... uh," Carrie squirmed uncomfortably. "I really don't want to get into the details, but we were involved with some friends and had some very private parties together. Mike and a couple others took pictures of us, uh... you know," she said. She looked at me with pleading in her eyes not to press for more information.

"I think I got it," I assured her. "And now someone has those pictures and is trying to blackmail you over them?"

She nodded miserably. "Yeah. I got an email containing three of the pictures and a demand for $25,000 or they will be sent to the head people in my company, to the newspapers, posted on the internet, and even sent to my kids and other family members."

"Do you have any idea who might be doing this? Could it be your ex?" I asked.

"I don't think it's him. He got the same kinds of demands and was sent pictures of him that should never see the light of day. He called me yesterday absolutely scared and mad. At first, he thought it was me trying to get more money from him, but I told him it wasn't me and about the email I got," Carrie replied.

I told her I'd help try to find out who was blackmailing her and recover all the pictures, but I had no idea how long it would take or even if I could do it. She immediately started crying and telling me how grateful she was. "Do you really think you can help?" she asked while wiping away her tears. "What would you do?"

"I need to look through your computer and see what I can find there before I can develop more of a plan," I said. "But don't worry. I'm not telling anyone about this or anything that I see or learn about, except you. Not even my Mom," I said with a glance to my mother sitting next to me. She just gave a brief nod in agreement.

Mom asked if I would be alright staying with Carrie while she left to take care of some errands. "You two are going to need some privacy. I really don't need to be here and would just get in the way. Why don't you give me a call when you need me to come pick you up?" she said to me.

"Sure, but I can walk home from here. It's not far," I told her.

After mom left, Carrie took me to her home office and showed me her computer. It was a pretty new iMac and I asked her, "How long ago did you take those pictures?"

"Before we had our kids," she said. "Why?"

"This wasn't the computer you had then. Did you transfer all the information from the old computer to this one?"

"I don't know. My husband took care of all that, but the pictures were supposed to have been deleted years before that," she responded.

She gave me the password and after logging in to her machine, I quickly found out there was no sign of the pictures anywhere on the hard drive. "The good news is, it doesn't look like anyone hacked into your home computer. We can do some things later to lock them out, just in case they did, but so far, it looks like a pretty clean system. When was the last time you actually saw the pictures on the computer? Were they taken with a digital camera or on someone's phone?"

"Mike used a brand new digital camera I got him for the previous Christmas. I don't think anyone used a phone," she said. "The last time I ever saw any of the pictures before this week was when I was pregnant with my first child and told Mike to delete them all. I couldn't bear the thought of our kids someday seeing us doing those kinds of things," she said pitifully.

"Does he still have that camera and the memory cards he used back then?"

"I don't know, but I'd guess so."

"Would you mind calling or emailing him just to check and see if he still has those things or if he ever made copies of any of the pictures?" I asked. Carrie wasn't thrilled about talking to her husband on the subject, but agreed that he would much rather hear from her than me.

As she went to get her phone, I started looking through the ransom email she received. I couldn't help looking at the three photos attached to it. One showed a much younger Carrie on her hands and knees with one man's cock in her mouth while another was fucking her from behind. Damn, she looked hot!

The second picture actually showed a larger scene with Carrie on her back on the bed with a man standing up against the end of the bed fucking her while two other men knelt on either side of her head and she apparently took turns sucking their hard dicks. The third picture showed Carrie wearing a strap-on dildo and fucking one of the men in his ass while two other women and a man watched from the side. I quickly closed the pictures before she returned and began scanning the email header.

It came from a common free email service and the sender probably thought that it hid his (or her) identity pretty well. However, one of the kids in my college showed me how to break down some of that protection and I started working through it.

Carrie returned and looked like she had just finished another session of crying. Her ex- apparently gave her a hard time and blamed her for everything happening to both of them. He did confirm that he still had the camera and amazingly enough, the same memory card he originally had. He didn't keep any copies of the photos that Carrie told him to delete and as far as he knew, they were gone forever, until now.

"That's the thing about the digital age. Nothing goes away forever once it's in the system," I said ruefully. Just then, a thought occurred to me. "What happened to the computer you used to have with all those photos?" I asked her.

Carrie stared at me blankly. "I don't know. In the trash? Like I said, my husband took care of all the technical stuff."

I went back to the ransom email, copied all the header information and sent a copy of just that data to my personal email. "I'm going to keep working on this using some tools on my home system," I told her.

"You didn't send a copy of the email to yourself, did you?" she said in alarm.

"No, no. Just the email header stuff. It shows the sender's email address, a respond to address, the various server IP address that it routed through. I'm not sending the body of the email or the attached files.

Carrie let out a long sigh of relief. I could see her eyes searching my face for any clues as to whether or not I'd looked at the pornographic pictures that were in it, but I returned her look with one of understanding and concern. And, I started to feel a little shitty about looking at them.

"Okay, as long as that's all you took," she said. She walked me back through the house and showed me out the front door. "Thank you again. I really hope you can help me soon. I'm supposed to transfer the money to them next Monday, after the banks open."

"Try and see if they will give you more time. Tell them you don't have that kind of cash lying around and need to liquidate some stocks or something," I suggested. She nodded, but didn't seem hopeful. I heard the door close behind me as I headed home. I couldn't stop thinking about the pictures in the email she got. Carrie looked much different back then and was definitely hot!

The next day, I called her and just said I was still working on the problem, but I had a couple ideas. I didn't want to get into any more detail on the phone and she was happy not to. The day after that, I managed a breakthrough by using a password cracker to gain access to the blackmailer's email account. As I looked through it, I saw the email that went to Carrie's ex and confirmed his story. Two of the pictures on it weren't too bad, but the third one showed him having sex with two other men and it was pretty nasty.

I called Carrie and then dropped by to see her a couple hours later when her kids were out visiting some of their friends. I explained what I had done and also that I found a ransom demand to her ex and one of the other men in Carrie's photos.

"You saw the pictures of me?" she asked in dismay and panic.

I admitted I did, but told her it was from the sent email on the blackmailer's account. I recognized her in one of the pictures they sent the man they were blackmailing.

Carrie looked absolutely miserable. "Who was it, do you know?" she finally asked.

"Not really," I admitted.

"Show me," she said. We went to her computer and called up the ransom note from where she had hidden it. As we opened each of the pictures, I could feel her shame and embarrassment growing.

"Right here. This was the guy. They sent him the same picture as they sent you," I said while pointing to one of the naked guys in the screen.

Carrie blanched. "Shit!"

"Why? What's the matter?" I asked.

"Don't you recognize him?" she asked in amazement. Seeing my blank look, she provided the answer. "That's our mayor!"

"Shit!" I said, echoing her comment. We looked at each other in disbelief that it could get much worse.

"What are you planning to do?" she asked.

I'm going to hack into his computer system, look around to see what else he's been up to, and figure out how to destroy all the data before he can stop me. Hopefully, nothing's been put on a backup drive or copied somewhere else for safekeeping," I told her.

"And if it is?" she asked in trepidation.

"Then you're fucked, and not in the way you'd prefer," I said in a weak attempt at gallows humor. Carrie gave a weak smile that vanished as fast as it came. "How long will it take?"

"That depends on how fast I can get him to open a file I sent," I said with as much confidence as I could muster. As I was leaving, Carrie gave me a lingering hug.

"I'm so thankful for all you're doing for me. I haven't slept well in days because of all the stress and knowing that you think you can help gives me hope," she said into my chest. I stood a little awkwardly and put my arms around her shoulders to comfort her.

"We're not out of the woods yet," I cautioned. "But it is looking up." I patted her back and then for some reason, I kissed the top of her head. I was immediately afraid I had way overstepped my boundaries, but she didn't seem to really notice. I let out an internal sigh of relief and just stood there feeling her large, soft body pressing up against me. When Carrie let go and stepped back, I could see she had been crying again and was wiping away the tears. "I'm sorry," she apologized. "I'm just a mess."

I tried to think of something to say that would ease her mind, but her phone rang and she let me out the front door before hurrying away to answer it. When I got home, I found a ping back from the Trojan Horse program that I sent the blackmailer indicating he had opened the email and viewed the embedded picture. "Gotcha!" I thought.

I spent nearly all of two days going through the computer on the other end of the email to Carrie and quickly found out what had happened. Apparently, the blackmailer had gotten a hold on the old computer she and her husband used almost fifteen years ago and either the hard drive wasn't wiped before they got rid of it, or the wiping program wasn't that good and someone managed to reconstruct most of the files. I managed to activate the camera on the blackmailer's computer, but saw a bare room with nothing to help identify it. After some additional checks, I determined that Carrie's old computer was in a small network containing several other PC's and one very large external hard drive that was used to back up data from one or more of the systems.

I couldn't be sure that erasing the pictures from Carrie's old computer would be good enough to shut down her blackmailer, and even if it would, someone would be bound to notice the lengthy hard drive activity and either shut down the machine or discover what I was doing before it was too late. That's when I had a flash and called one of my college friends. By the end of the day, he had sent me a small program that would do what I needed. He didn't tell me where he obtained it, but assured me that it was quite effective and easy to use.

I uploaded the program not only on to Carrie's old machine, but used the network connections to load it onto all the other PC's in the small LAN. Before starting the program, I started copying as many of Carrie's old pictures to an encrypted cloud server I used and held my breath that no one would show up in the room on the other side before I was done. Fortunately, I was able to get everything moved to my cloud drive before that happened and then I quickly launched the program I got from my friend.

I was told that once started, the program could not be stopped. Even if the computer was shut down in the middle of execution, it would automatically resume its work before anything else could happen as soon as the computer was turned back on. I received a short confirmation note when Carrie's old system was finished and then I called her to tell her I had good news.

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