Crossing Boundaries With Kat

Shari and I have been married for almost 6 years and this is both of our second marriages. I'm 46 and Shari is 50, but we both look much younger than our ages. Shari is a gorgeous blonde with big fake tits and a tight little ass. I'm tall, bald and in pretty good shape myself.

Shari's 3 sons are all adults now and 2 of the 3 have moved out and started lives with their girlfriends. Shari's oldest son and his girlfriend just bought a house down the street from us. Her middle son, Ken and his girlfriend, Kat live out of state with their 2 year old daughter. The youngest son still lives with us and is trying to get his life going.

We don't get to see Ken, Kat and our grandbaby as often as we'd like. They usually come down and spend the holidays with us, but that's about the extent of seeing them.

Let me start by saying that I'm pretty much a closet pervert, so I've fantasized about everyone in my life. Friends, co-workers, my step mom, friend's wives, family, etc. Kat is no exception. She's 26 years old, but not anything to look at. She tries to look nice, but frankly, she's pretty ugly. In my eyes, she not attractive by any means. She's average height and weight, long brown hair and blue eyes, but she has small tits and a big dumpy ass. Not in a good way. However, that doesn't keep me from wondering if she is a good cock sucker or flirting with her a little bit when I get the chance.

This past Christmas, Ken and Kat came to our house and spent a couple days with us. One night, Kat and I were sitting in the living room watching TV while everyone else was cooking in the nearby kitchen. Kat and I made small talk about the show we were watching while the loud kitchen conversation behind us was going on.

One of the characters on TV joked about not getting laid now that he's married. I laughed and rhetorically said, "Isn't that the truth."

Kat smiled and asked, "Is that true about marriage?"

I asked, "What? You mean, no sex after you marry?"

"Yeah."

I said, "It's true. Once the man says I do...the wife says, I don't have to anymore."

Kat said, "That would suck. I don't ever want to get married then."

I just smiled.

A few minutes later, Kat got up off the couch and began walking past me. I said, "Yep. Marriage is pretty much about jerking off."

Just as Kat began breaking the threshold to the kitchen, she stopped and said, "I'd watch that."

After she walked into the kitchen and joined the conversation, I got a little twitch in my pants as thoughts entered my mind about what it would be like to let her watch me masturbate. I silently asked myself, was she serious? Would she really want to watch me? I knew I would love it, but how do I ask her? How would we pull it off without getting caught? All these questions entered my mind, but I put them aside and enjoyed the rest of the weekend with everyone. But, it didn't keep me from looking at Kat a little differently now.

After the holiday, Ken and Kat took the baby back home. A few days later, I received a text from Kat. "Hey. Thanks again for the hospitality. Have a happy new year. I'm on Skype quite a bit so hit me up sometime."

At first I couldn't figure out why she told me to find her on Skype, but then it hit me! Maybe Kat really does want to watch me jerk off!

About a week went by since she texted me, but I spent that entire week thinking about showing my cock to my daughter in law. Well, she wasn't technically my daughter in law, but she is the closest thing I have to one. One night when Shari was at work, I pulled up the Skype website and joined. I got the camera and microphone configured on my computer and began looking for Kat. I quickly found her and saw that she was currently online!

I sent her a request which she accepted within seconds. Her picture popped up and my heart began to race, but I played it cool. The camera was focused closely on her face, which reminded me that she was not exactly Miss America. Nevertheless, we both smiled and asked how each other is doing.

Kat went on to tell me about how the baby was doing and her busy day taking her to routine doctor's appointments and then to get ice cream. After a few minutes of small talk, I was trying to gain enough courage to ask if she was serious about seeing my penis. But then she asked, "Do you want to say hi to the baby?"

I paused for a moment said, "Sure!"

Kat reached over and brought the baby into sight. I talked to them both for a couple minutes and then Kat put the baby down. We wrapped up our conversation and I was just about to click out when Kat said, "I'll be home alone tomorrow. The baby takes a nap about 2pm if you want to talk then."

I said, "Tomorrow is my day off, so I'll see what I can do." With that, I smiled and ended the Skype session.

I sat at my computer for a couple minutes and realized that Kat was completely serious about watching me masturbate. In fact, she was making it happen. She's the one that told me about Skype and to find her on it sometime and then just made herself available to me tomorrow at 2pm. She was playing it cool and not stepping too far out of line to explain her way out of it, but now I was completely intrigued by my perception of her naughtiness. I have known her for a couple years now and never once got a hint that she was a dirty girl.

I woke up the next morning and spent the first part of my day with Shari before she had to go to work. We went out to breakfast and ran a couple errands, but my mind was on my upcoming Skype session with Kat. I couldn't wait to see how far this was going to go. When we got home, Shari quickly got ready and left for work about 1pm. As soon as the door shut, I jumped into the shower and freshened up my manscaping, shaved my balls and put my favorite gold cock ring on. I figured it wouldn't hurt to put a little jewelry on it for Kat. I have to say my package looked quite impressive, clean and thick.

I put on a t-shirt and pair of basketball shorts. The clock hit 2pm and just as I sat down to my computer, I got a text from Kat. "I'm online."

I quickly logged on and there she was, smiling from ear to ear. The camera looked like it was further away from Kat today than it was yesterday. I could see her face and the top part of her white tank top. It looked like the tank top that Shari and I bought for her at Christmas.

I said, "Hi. How has your day been?"

"It's been good. The baby has been cranky all day, but thank God she's asleep for a little while."

I asked, "Are you wearing the top we got you for Christmas?"

"No. This is just a wife beater I wear around the house."

Kat reached up and moved her camera down to show me the shirt. She was wearing a standard white "wife beater" shirt and it was obvious she wasn't wearing a bra. Her tits were about a small "B" cup, but her hard nipples showed clearly through the thin cotton and her areolas were really big and really pink. I wasn't sure if she was aware of how exposed she was, or did she? She moved the camera back to her face and smiled. I think she knew exactly what she was doing and I sure as hell wasn't going to tell her to cover up.

After some awkward small talk, Kat began opening up to me.

"Can I tell you a little secret?"

I said, "Yes, of course."

"You told me that married people don't have a lot of sex. Well, Ken and I haven't been having much sex either, and we aren't even married yet."

I asked, "Why do you think that is?"

Kat went on to tell me how Ken is working a lot and she's left at home all day with the baby. When Ken gets home from work, he's too tired to do anything but take a shower and go to bed. Kat said she needs some companionship, but she only gets Ken for 2 days a week and he's usually more interested in spending his days off with the baby. She said she rarely gets alone time with Ken.

I explained that relationships are not easy and that both partners have to make time for each other. I suggested she talk to Ken and let him know how she feels.

She asked, "I don't mean to be intrusive, but do you and Shari have sex?"

I said, "Yeah, we have sex but not frequently at all. We are both getting older now."

She asked, "Your libidos have disappeared?"

"No. My libido is still raging, but I think Shari's interest has diminished."

Kat asked, "So, how do you handle that? Do you have a girlfriend?"

I laughed. "No girlfriend for me. Like I told you at Christmas, I do what every other monogamous married man does. I jerk off."

Kat smiled in silence for a moment. "I don't know why, but I think it would be hot to watch a man play with himself."

I was right! She really does want to watch me jerk off! My heart started racing, but I kept it cool.

I asked, "Ken hasn't let you watch him?"

"He has, but it's been so long ago. I really enjoyed it when it happened."

I asked, "What did you like about it?

"I don't know. I thought it was really fucking hot to see how he made himself cum."

I said, "Shari likes to watch me too. I think it's a primal thing with women or something."

Kat then gave me a little smirk and asked the million dollar question, "Maybe you can show me?"

I got a huge smile on my face.

"You really want to see me masturbate?"

Kat put the tip of her index finger in her mouth and nodded yes. Her naughty look sent blood to my crotch and I could feel my cock ring getting tighter as my cock grew in my shorts.

I said, "To be honest, I've been thinking about it since you said something at Christmas. I'd love to show you, but I'm afraid it will get back to Ken or Shari."

Kat looked straight into the camera, pulled the top of her tank top down and let her left breast fall out of her shirt.

"This is our little secret. Plus, I went first so if anyone gets in trouble, it's me." Her little titty was definitely not picture perfect, but it was young and mine to look at now.

I giggled and said, "You showed me yours so I guess I have to show you mine now."

I pushed away from my desk and made sure my body was visible to Kat. I pulled the front of my waistband up and took a peek at my circumcised meat inside my shorts. My cock was so hard now that the veins were engorged with blood and my cock ring was tearing into the underside of my nut sack.

I looked up at the screen and asked, "You really want to see it?"

Kat nodded yes.

"How bad do you want to see it?"

Kat said, "Just show me."

I extended the front of my waistband further and let the head of my cock out for Kat to see. My cock was fully hard and looking great. I watched Kat lean in toward her computer to take a closer look.

She quietly said, "Keep going Daddy. I want to see all of it."

Wait. Did she just call me Daddy? Oh my God, that was so fucking hot and kinky! I was so turned on by her naughtiness that I almost blew my load right there! It wasn't long before pre-cum began making its way up my shaft and started pouring out of my cock head like a faucet.

I lifted my butt off the chair and pulled my shorts off. My cock was standing straight up on its own and continuing to leak juices down the sides of my shaft. It was an amazing feeling after two weeks of anticipation to sit there with my thick meat fully exposed to Kat for the first time.

"Wow Chuck! You have a beautiful penis!"

I said, "Thank you."

"Take your shirt off and get closer to the camera."

I stood up directly in front of my computer so Kat could get a closer look while I removed my shirt. I have to say, I was pretty proud of how thick and veiny my meat looked at this moment.

"I love your cock ring!"

I said, "Thank you. I wanted to wear some jewelry for you."

"You're leaking. Do you usually leak a lot?"

I said, "Only when you call me Daddy."

She said, "Daddy?"

I didn't know what to call her, so I said, "Yes baby girl?"

"I wish I was there to taste you."

I instantly and uncontrollably grabbed my meat and wrapped my hand around my veiny shaft. Oh fuck! Kat is a fucking sex freak at I was loving it!

I stayed standing in front of my computer and looked down to make sure my cock was in full view so she could see me. I slowly slid my grip up and down my length while I watched her face intently. More and more pre-cum oozed out of my cock head with every slow pass. Kat was now rolling her exposed nipple between her thumb and index finger with one hand and the other hand was out of view.

I said, "Take your shirt off."

Kat instantly ripped her top off over her head and threw it behind her. She was now sitting in front of the camera with both of her little tits out for me to watch while I gave her the show she asked for.

I asked, "What bottoms are you wearing?"

Kat pushed her chair back to show me that she was wearing loose full length pajama bottoms.

"What do you have on underneath?"

Kat said, "Nothing Daddy."

"Go put on your favorite pair of panties for Daddy."

Kat darted from the computer and came back in 20 seconds flat wearing nothing but a little pair of pink cotton panties. She sat back down in the chair and began pushing forward toward her computer.

I said, "Stay back there. I want to look at you for a little bit."

Kat pushed her chair back away from the computer and spread her legs slightly. I could see a slight camel toe and her clit through her panties. I have to say, her nicely trimmed pussy was more impressive than I expected. She started playing with both tits now while she stared at my cock.

"I love your panties."

"Thank you Daddy. I bought them for you yesterday."

Oh my God! She knew exactly what to say to get me excited! I slowly increased the pace on my hard cock and watched as she moved her right hand down and began rubbing her pussy through her pink panties.

"Sit back in the chair Daddy. I want to watch you make yourself cum."

I quickly moved back to the chair and spread my legs so she could get a good look at everything I had to offer. I gripped my cock again and stroked at a medium pace. I was so turned on by breaking this taboo, I knew it wouldn't be long before I came. I closed my eyes as I enjoyed the moment and felt the head of my cock become insanely sensitive, the indication that I was close to reaching orgasm.

I heard a slight squeak from the computer and opened my eyes. I couldn't believe what I was seeing. Kat now had her hand inside her panties and was thrusting her fingers into her pussy with the look of lust on her face while she watched me. As wrong as it felt to be doing this with my daughter in law, it also felt so right at the same time. We were two undersexed people enjoying each other, without crossing any physical boundaries.

I said, "Kat, you're going to make me cum if you keep doing that."

"Cum for me Daddy! I want to watch you cum."

Oh God, I can't handle it when she calls me Daddy. I leaned my head back and started jacking off at full force. I grabbed onto my ball sack with my free hand and squeezed as hard as I could. I instantly felt the semen rushing up my cock shaft like a freight train and arched my back just as it reached my cock head. I let out a loud groan and began spraying cum into the air, shot after shot and continued jerking at the same pace over and over again, semen landing back onto my body.

As my orgasm subsided, I slowed my pace and eventually released my grip. I looked around at the mess I made all over my stomach and the carpet surrounding my chair. I took a couple deep breath to regain my composure and looked up at Kat.

Kat was now sitting in her chair spread eagle with a huge smile on her face and both of her legs up on the chair arms. Her face was flush red and there was a clearly visible wet spot on her panties.

She broke the silence and said, "That was beautiful to watch."

"I'm glad you enjoyed it."

She said, "You're a heavy cummer Daddy."

I said, "I haven't cum that hard in years."

"Thank you for cumming for me."

I said, "Keep calling me Daddy and I will cum for you anytime you want."

There was a short pause.

I asked, "Will you cum for me now?"

Kat pointed down to her wet panties and said, "I already did."

Just as I was about to ask her to make herself cum again, I heard the baby crying in the background. Kat looked away from the computer and nervously said that she had to go because the baby woke up. I watched as she darted from her computer and out of sight.

I wondered if we would ever have this opportunity again and took a deep breath before clicking out. I sat at my computer for a while, reliving our kinky taboo Skype session. Here I was, just masturbated with a woman who I wasn't really physically attracted to, but the fact that she is my daughter in law made it so hot. We both crossed some serious boundaries, but I didn't really care at this point. Would she masturbate for me next time?

Will we both be able to keep this a secret? How awkward will it be next time she and Ken are at our house?

I couldn't answer any of these questions, but It wasn't long before I was hard again and finishing myself off for a second time.