Landlord Benefits Pt 02

I wanted to thank Shygirlwhore for editing my story for me. If you find any errors, they are definitely mine and not hers.

I hope to continue this series as time permits. Please let me know what you think.

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Chapter 5

A few days after banging Jennifer and Melanie, I was out cleaning our pool. I heard "Excuse me," coming from the other side of our side gate. This is the gate nearest our little studio apartment that Melanie rents out. I looked over and saw our neighbor that lived on the property nearest the backside of the rental. Her name was Kelly, I knew that much, but her family really kept to themselves. We've talked maybe a handful of times in the past 6 years that they've lived there. She is married with two step children. Her husband Gary had one boy and one girl before they got married. Both of the kids are adults now. I estimated that she is probably about 10 years older than me give or take. She worked in town and liked to ride her bike to work. She was in decent shape for being 50 and up. I find it amazing how my taste in women has changed over the years in the sense that I can still see utter beauty in an 18-year-old girl as well as a 50-year-old woman. But when I was 18 that 50-year-old woman was not even close to being desirable. At any rate, she was looking good for her age. She reminded me a lot of Mary-Louise Parker from the series "Weeds" but with lighter brown hair.

I said, "Oh hey Kelly. How's it going today? Come on back." I motioned my head towards the gate.

She opened it and walked in. She was in, what I'd consider gardening clothes. I assumed she had been working in her backyard before coming over.

"I thought I heard you back here so I thought I'd come and say hello." She said. "I've been working in the backyard a lot lately on our new garden which gives me a lot of time to think."

"Oh yeah? What are you growing back there?" I asked.

"We figured we'd grow what we use the most in our house so we have tomatoes, bell peppers, jalapeño peppers, some basil, some oregano, and some zucchini. Although the tomatoes just aren't doing as well as we thought they would. There has to be something we are missing." She answered.

Honestly I found this conversation a bit strange. Not to be a jerk but what do I really care? She rarely talks to me or Jennifer, rarely waves as we drive past her house, but here we were.

"Sounds awesome. I hope it goes well for you. Can I help you with something?" I finally asked.

She was looking at the pool as I skimmed the bugs and leaves off the top. I could tell that something was on her mind.

"Is there somewhere more private we could talk?" She asked.

"Could you tell me what this is about?" I asked back.

"It's sort of something I think you'll want to keep private." She responded.

I was confused as heck by now. "Let's go to the loft above the garage. It is as private as it'll get." I motioned towards the stairwell at the back of the garage.

She nodded in agreement and we both headed up there. I let her lead the way. As I walked up the steps I stared at her beautiful ass. She kept it in great shape. I motioned for her to have a seat on the couch. I walked over to the bar and asked her if she wanted something to drink. As she was looking around at my all of my man cave decor, I had the foresight to turn on the camera by the end of the bar that I never moved.

"Just a water if it isn't too much trouble." She responded.

I poured her a glass of water and grabbed a beer for myself. I handed it to her and then walked over to my desk. Put my beer down, and turned around towards my other camera. I wanted to turn it on without her knowing. So I started making small talk and acted like I was looking at a few books. My body was hiding most of what I was doing so I didn't think she'd know anything was up. After getting that camera on too, I turned around and said, "So what's up? What needs to be kept private?"

She looked up at me, making eye contact and said, "I know you are screwing around on Jennifer. There I said it." And she let out a long breath as if she'd been holding it for hours.

I was a bit shocked. I wasn't angry because obviously my girlfriend knew everything. But I had no clue how Kelly knew.

"Oh and you know this how?" I asked.

"Well as I told you I've been working in the garden a lot lately. I heard you spraying several days ago and peeked through the opening in the bushes when you stopped at your renter's window. I saw everything!" She continued. "At first I was shocked. Then I realized the knowledge of what you were doing empowered me."

"Empowered you how?" I asked. Still sort of amused.

"Well, I'm sure you don't want Jennifer finding out. So it allows me to pretty much name my price." She responded.

"So you are blackmailing me?" I asked in a fake angry tone. "How much do you want?"

She sat there and took another sip of her water. She acted like she was thinking of a number. "I...it's not money. I... I sort of want...want to have sex with you. It's been so long since I've been laid and I was so turned on after thinking about you watching your renter dance for you."

I was blown away. "What? You've got to be kidding me!" I acted surprised and outraged. "And if I say 'no' then you'll tell Jennifer? What if I tell your husband that you are doing this to me?" I asked.

"You really think he'll believe you? How many times have we talked since we moved here?" She asked.

"You have a point." I acted like I was thinking about it. But I really wasn't. Not at all. "So if I agree, then what?"

"Well you will agree." She said pretty forcefully. She started unbuttoning her shirt. "You'll agree because I think you find me attractive and you wouldn't want Jennifer to find out." She got to the last button and pulled her shirt off revealing a pretty attractive set of breasts for a 50-year-old. She had what I'd consider a standard type of bra on. It was just black and had nothing special to it. I found it strange, though, that she obviously had this planned out yet didn't dress up more. I figured maybe she knew she would do it but just didn't know exactly when. And when she heard me outside by the pool she rushed over spur of the moment.

"I obviously have no choice in the matter." I acted defeated. "But I do find you attractive so I can make the best of this situation."

I walked over to her and bent over and kissed her on the mouth. She didn't hesitate at all. She opened her mouth pretty aggressively and reached down to grabbed my cock which was still inside of my pants. It was quite obvious that she did not have sex very often. She was like an animal that hadn't eaten in a long time. I reached around with my right hand and unhooked her bra. It fell to the ground as she stood up. We continued to kiss. I started fondling her breasts. Since they weren't huge, gravity really didn't negatively affect them too much. Seeing her topless verified how good of shape she was in for her age. I always thought that her ass was her best attribute but now that I'm seeing her tits and abs, it is a toss-up.

I paused kissing her. "You are super hot. Why aren't you getting laid more?"

She started to unbutton my shorts. "Gary just isn't interested anymore. It doesn't matter what type of lingerie I buy; he is always too tired. He gets home from work later than he used to and has odd appointments. I just assume he is getting it elsewhere." She answered without much emotion.

She got my shorts and underwear down to my ankles and grabbed my cock. She got on her knees and started licking the mushroom tip as it started to harden completely. She started working her tongue down my shaft and back to the tip. She stroked me in between licks. "I want you to unload into my mouth. It has been so long since I've tasted cum." She demanded.

I reached down and fondled her right tit while she gave me a blow job. She was definitely experienced in this area.

"She better be based on her age,"

I thought. I was getting closer to blowing my load. I mostly just wanted to blow my nut so that I could make her happy, and then hopefully bury my dick into her pussy. But I wanted her to continue to think she was in control. "I'm almost there." I exclaimed as I grabbed both sides of her head. A few moments later I started to unload a few days' worth of cum. She kept sucking until there wasn't a drop left in my dick. She looked up and stuck her tongue out showing me some of my cum. Then she closed her mouth and swallowed with a big smile.

She stood up looking quite pleased with herself. I asked, "Is my secret safe with you now?"

She laughed. "Oh we aren't done yet." She started unbuttoning her shorts. "I hope you have more in those nice big nuts of yours!"

I reached down to help her with her shorts. I pulled first her shorts and then her underwear down. I was greeted with a completely bald vagina. I took my shirt off so that we were both naked now. I sat her down on the couch and got on my knees. I spread her legs open and started to lick her baldness. I spread her pussy lips with my right thumb and pointer finger and started licking her tasty pussy. She immediately responded with some moaning. My tongue found her clit and started working it in a soft circular motion. She started moaning more and more as I worked out my tongue muscles. She grabbed my head and pulled it toward her pussy pretty forcefully. I continued to lap at it until she was in full climax. She moaned pretty loud as she had her first orgasm. This got me to full erection again and I didn't want to waste a good hard on. I got up a bit and started working my mushroom head into her very wet vagina. I worked it around the lips a little and got the tip wet and was in it in one stroke. She was surprisingly tight though. I think she has benefited from marrying someone with two kids rather than having some of her own. As I went deeper her moans got louder. I pulled her off of the couch and onto my body as I laid on my back. She started doing most of the work. I reached up and fondled both tits. I worked my fingers around her hard nipples. They were at least a half of an inch long. As she road me I alternated between grabbing her ass cheeks which felt like a 20 year olds ass and her hard nipples. She continued to work up and down. I thrust in unison with her downward motion. We started to increase our speed. I was getting closer to my second orgasm and I could feel like she was as well. She started moving much quicker. She put both hands on my chest as she started writhing almost uncontrollably. She yelled "Harder, harder," so I complied. I thrust into her as she came down on me. I grabbed her hips to help pull her down and push her up. I started cumming as well. I shot a few ropes into her as she continued to ride me to finish. Finally, she slowed down as her pussy muscles milked me dry. She laid on top of me with my cock still buried inside of her. We laid there for a bit just catching our breath.

"I think that takes your blackmail off of the table." I said and laughed.

After a few moments she responded, "Yeah it does. As fun as this was it can only be a one-time thing. I really just needed to get it out of my system. Plus I don't want to be like Gary and cheat all the time...this sure was fun though."

I laughed. "Yep it sure was. But I gotta tell you something. Jennifer knows about Melanie and me. In fact, it wasn't too long ago that I was boning them both right where you are right now." I moved her off of me and got up. I grabbed my laptop from my desk and double clicked the file on the desktop called "Fun." I slid the slider bar way to the right and turned it towards Kelly. Her eyes got super wide as she saw me screwing Jennifer in the ass as I fingered Melanie's ass.

"You could've just come over here and asked me to screw you and I would've happily obliged you." I said still amused and quite proud of myself.

"You filmed them? Wait, did you film us?" She asked still very shocked.

"You bet I did. So who is empowered now?" I asked as I winked at her.

She immediately got an evil look in her eye. "You better not tell Gary!"

"Or what?" I asked. "So you can blackmail me but I can't blackmail you? That hardly seems fair." I was still proud of myself for this turn of events.

She looked defeated. "So now what? I'm your little sex slave like you were mine? I come over at your beckon call?"

"I suppose it depends how important this is to keep from Gary." I replied. "Maybe you'll be more than just my sex slave. Maybe I'll come up with more that you can help me with." My mind was wandering to her friends. I hadn't seen many come to her house but assumed there had to be some MILFs in that list. My mind was thinking about her step daughter too. "It obviously is no secret that I like women and Jennifer is open to me having sex with other women. Believe me, I'll come up with ways you can help me."

I walked back to the bar and grabbed another beer. "Want another water?" I asked.

"No." She answered. "What do you mean that you'll come up with ways for me to help you?"

"How about you just get dressed and I'll let you know when I need to cash in." I answered. "Give me your cell number so I can get ahold of you whenever I want."

She gave it to me and then started to get dressed. She turned her body around so I couldn't see the front. All of a sudden she was acting shy. But her ass! Wow did she have a nice looking ass. Up until this point I hadn't seen it. I had only felt it. I walked over and got right up behind her and grabbed her ass cheeks with both hands. I whispered in her ear, "Don't worry. I'm only doing what you did to me. And I promise that you'll have fun."

At that, she got completely dressed in silence and headed out the door. I sat down at my desk very satisfied. I couldn't believe what just happened. I needed to watch some of the video and start planning how to use this to my advantage.

Chapter 6

I spent a few days researching and ordering some new equipment for my man cave. I wanted to set up some Wi-Fi and motion activated high definition cameras. I bought some hidden cameras because I felt like they would be best for my needs. I found a smoke detector camera that I placed right above the couch. I found a camera built into a clock to replace the one I had on the bar, and I got a camera that doubled as a tissue box to go on my bookshelf. All in all, I spent about a grand. But it was money well spent in my opinion.

I overnighted it all and set it up immediately when it showed up. After testing it thoroughly it was now time put it into action in some way. I knew that I could just call up Melanie or Kelly and have them here pretty quickly. So I decided to call up the neighbor Kelly. I had two reasons: first, I wanted to do her doggie style. I really did like seeing her super fine 50-year-old ass. Second, Jennifer and I were heading out to Vegas the next weekend and I really wanted Kelly to have her step daughter house sit for us. I really didn't want to pay her either so that was something I wanted her to figure out.

A few hours later I met Kelly up in the loft. She was dressed more for the occasion than last time. She had on a loose skirt and a spaghetti strap shirt. She definitely didn't dress her age. But she looked really good in this outfit.

I still hadn't told Jennifer about my first meeting with Kelly so I needed to keep this pretty short to avoid Jennifer catching us too. I knew I'd tell her eventually; I just didn't want to be caught in the act.

"How are you today, beautiful?" I asked.

"I'm doing ok. I was wondering if you were ever going to call. Did I wear you out last time?" She smiled.

"I had a lot going on at work and I didn't want to piss you off too much." I answered. "But I didn't want you to forget about our little agreement so I figured today was as good as any. Plus, I need a favor already."

"Besides making me cheat on my husband again?" She asked.

"Don't pretend to be so high and mighty." I raised my voice. "You are the one who started this entire ordeal. If it wasn't for you, we still would hardly be talking. Now take your clothes off!" I demanded.

She started taking off her top. "What is the favor?" She asked.

"Jennifer and I are going to Vegas next weekend and I'd like your step-daughter to watch over the place." I said as I watched her get naked. "Would you be able to get her to do that for us? Sorry I don't even know her name."

"It's Audrey." She responded now starting on her skirt. "I don't see why that would be a problem for her unless she is going to be gone with her friends that weekend."

"Well let's make it happen. I'm banging her step-mom. I might as well get to know the rest of the family." I smiled.

"No corrupting her though! She is a very good girl." She told me. "She is a 4.0 student even as a freshman at college. We don't need that changing. I'm pretty sure she is also a virgin so keep your hands off!"

She didn't have any underwear on underneath her clothes. She was now completely naked and my cock started to harden.

"Well she would have a nice pool to relax in and a house all to herself. It should be fun for her. Just no boys allowed." I said as I started taking off my shorts.

I motioned for her to twirl around for me to see her entire body. She truly was a beauty. I always noticed she was attractive, but it seemed like she was even more so today. For her age, she didn't have a single wrinkle that I could see. When I saw her ass my dick sprung a bit more.

I pulled her over to my favorite location which was the side of the couch and bent her over so her hands were resting on the arm rest. I licked my middle finger and reached down and rubbed her slit with it. I worked it around getting her nice and wet. I didn't want to waste any time so I spit on the inside of my hand, rubbed it all over the tip of my dick and started to go to work. I pressed it up against her bald pussy and was in it in no time at all. We both knew this was a 'wham bam thank you ma'am' screw so we made small talk as we were going at it.

"Can you have Audrey call me or stop by tonight?" I asked as I thought about her cute blonde step daughter who was about 20 years younger than me. "I'd like to get it lined up quickly if possible. This is sort of a last minute business trip... oh shit you feel good!" I exclaimed as I started thrusting deeper. "Your ass is like a 20-year old's. So hot!" I reached around and grabbed her left tit. "So hot!" I repeated.

"I'll tell her to stop, oooohhhh, by." She purred. "I don't need her asking how I have your number."

She matched my rhythm perfectly. She was a great screw. "So she is a virgin, huh?" I asked. "Is she saving herself or what?"

"Don't get any ideas! Ugghh." She responded. "I said I think she is a virgin. I'm not sure. She is just a good, uggggghhhh. Oh man that cock of yours fills me so good! Uh she is a good girl."

"You are so tight. You must be telling me the truth about not getting laid much." I told her. "I'm getting closer to cumming."

"Me too... go faster!" She said.

I grabbed both hips and started working her faster and harder. I could fill my orgasm just around the corner. She started backing into me faster and faster and at that very moment she let out a loud moan, I shot my first load into her pussy and load after load followed until she completely milked me dry. We both came off of our high and I dismounted.

"What a lay!" I told her.

"You aren't so bad yourself. Even a quickie with you is better than foreplay and making love with Gary." She put an emphasis on the word 'love.' "Honestly when you turned the blackmail thing around on me I wasn't sure I wanted to do this again, but I think I could get used to this so long as nobody finds out."