Landlord Benefits

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 this story continues into a series if time permits. Please let me know what you think.

Chapter 1

I have no idea how this particular conversation even started but our flirting had gotten to the point of dangerous the more we conversed and texted each other. I was talking to this 30-year-old gal named Melanie, who rented a little studio apartment from my girlfriend, Jennifer and I. She let it slip that she would do anything for me if I bought her some lingerie. She was a gold digger apparently. She also knew that I was in a very serious relationship so she knew she wouldn't be getting tied down to anyone.

She had been renting from us for about a year and I'd mostly just seen her leave in the morning for work and come home around 5:30pm each day. She kept to herself which was fine with us. She kept such good care of her body that watching her coming and going was a pleasure. One time I was in her apartment fixing her leaky shower head and noticed all of her workout items. I had always wondered what she did in here by herself all day long with no computer or TV. Now I know. Doing some repairs in her apartment is how our flirting started. I remember asking her about the bumper sticker on her car that said: "I'm a tri-sexual: try me." That particular bumper sticker opened the door to many explicit conversations over a few months' time.

Today, we discussed what exactly she wanted from Victoria Secret and we agreed to have a prequel "show" to see what she looked like in her "older" stuff. She met me in the loft above our garage that I dubbed my "man cave." It had its own outside stairwell hidden from the street and was closest to her apartment. My girlfriend was at work at the time but we agreed it was the safest spot to meet anyway. She walked in with a robe on and without saying a word twirled around as the robe fell from her body to the floor. She had on a bra and semi see-through G-string panties. They did look old but still looked great on her.

As I looked from her flowing dark red hair, down to her smallish breasts that were trying to jump out of her tight green bra and down to her very fine ass I couldn't help but get rock hard in no time. I reached out and grabbed her ass and she jumped a bit, acted slightly offended, but then smiled. I told her I would place my order later on that evening. I asked if I could take her top off to see her tits but she declined. I could tell this was something she was a bit embarrassed about. She loved showing off that ass, but was reluctant to show off those tits.

"If I buy this lingerie for you, then I get to see you put it on from your birthday suit right?" I asked.

"That is the deal." She responded.

I looked at her from the front again and could see a nice, dark, and well-manicured rectangular strip of pubic hair through her panties. "Does the carpet match the drapes?" I asked with a smile.

She responded also with a smile, "I guess you'll have to find out."

She started walking out and I pulled her back in. I grabbed her ass and tried to kiss her. I was so turned on at this point. She pushed me away albeit reluctantly. "Let's just mess around a bit; nothing serious or too far...maybe just some heavy petting or a blow job." I pleaded.

She just shook her head and walked out.

"What a tease!" I thought. I was blue-ball angry! I pulled down my pants and beat off right there in my loft. I was hoping she'd change her mind, walk in and finish it for me but to no avail.

A few minutes later I texted her about her tits; I told her how much I wanted to see them and after some prying found out that a previous boyfriend told her they each were a different size and that made her self-conscious. I assured her that I'd only see their beauty and we left it at that.

The next day was Saturday and I had all of my normal chores around the property. We lived on the outskirts of town on a pretty decent sized parcel. The city was moving towards us but our property would be safe for quite a while. The downside to having a large property was the upkeep. It did not keep itself up so someone needed to mow, spray for weeds and bugs, trim trees etc. Today was bug spraying day. I had to spray the exterior of each of our buildings. I texted her, as I always do, that I needed to spray around her apartment so she could either leave for a while or stay in for a bit to let the spray sort of dry up. She knew the drill. I also texted her that if she opened her back window blinds, the one that was on the far side of her apartment and hidden by a row of trees, that she would see a welcome sight.

I slowly made my way around the apartment making more noise than usual so she would know where I was. As I came towards the backside of the apartment, her blinds went all the way up. As I pulled my pants down to flash her I noticed she was completely naked and smiling at me. I mean completely naked. I was able to verify that, indeed, the carpet did match the drapes. Her little patch of red pubic hair was showing and her two little size B tits were there in all their glory as well. She was looking gorgeous and I got hard again. She had a sucker in her mouth that I didn't notice until she pulled it out and started doing a little dance for me. I could faintly hear some music on inside and she was dancing to the beat. She has done this before. I stood there in shock but I admired what was in front of me. She turned around, bent over and stuck the sucker in her pussy and slowly worked it in and out. I was beside myself. I could see her asshole just staring at me. I mouthed for her to let me in the apartment but she just shook her head and smiled in a very teasing way. She turned back around and stood up and put the sucker in her mouth again and worked it back and forth in there as well. I was about to explode without even touching my dick. She rubbed her tits with her hands and then grabbed the sucker again and slowly put it in her pussy again.

"What a fricken tease!"

I thought. I couldn't believe my luck though. This little lingerie purchase was getting me all of this?

"I had better be deep inside of one of those three holes within a week."

I thought.

Just as I was contemplating my next move she grabbed the cord from the blinds and shut them. I just stood there wondering what next. I knocked on the window and she peered through the blinds and just waved at me and shut it again. Needless to say, I went into my loft and took care of business. This blue ball stuff is killing me!

I ordered her the lingerie and now it was time to wait. We exchanged several more texts over the next few days as we waited for the shipment to show up.

Chapter 2

I have to admit; I've felt a bit guilty about doing this to Jennifer. I hadn't cheated on her to this point but I sure wanted to. But one of the great side effects of the flirting that Melanie and I had going on is that it added a lot to my sex life with Jennifer. Did it really matter who I was picturing when I was banging my girlfriend?

"You sure have been a stallion lately," Jennifer told me one night when she got home from work. "Are you taking pills or something old man?" She teased. We were both 40 and it was always a joke between us that I'd have issues getting it up very soon. So far that was not an issue whatsoever.

Jennifer walked over to me as I was sitting on my recliner. She hopped on my lap and wiggled her ass a little. "You have more in that tank for me?" She asked as she wiggled some more.

"Well I'd say if you can manage to get me hard enough then I can muster up a thrust or two." I replied. I leaned my chair back and she turned around to face me. Jennifer was completely different than Melanie. She was sandy blonde. Very cute as well but her breasts were larger. She had a little bit more meat on her, but in a healthy way. She stayed in good shape just like Melanie did. One thing I did know is that she sucked my dick very well.

She pulled her shirt off and kissed me shoving her tongue into my mouth. She was a great kisser as well. She grabbed my cock as I started getting hard for her. She stood up off the chair and let go of my cock and motioned me to the bedroom. "Let's take a shower." She said. "I need to get work off of me...and I need to get you onto me." She smiled.

We both undressed as we walked to our walk-in shower. She turned the shower on and we kissed as we waited for the water to get warm. I reached around and grabbed both her firm ass cheeks. She had a super fine ass and I started getting hard again. She reached down and stroked my cock as she continued to kiss me. I lifted her up by the ass cheeks and she straddled my body as we kissed some more. We stepped into the flow of water and continued to kiss. As the water flowed down our bodies I couldn't help but think about Melanie. I felt a tinge of guilt as I was making out and getting ready to screw such a beautiful woman. I set Jennifer down and turned her around. I bent her over and started licking her wet pussy. Her beautiful body moved to my licks. I continued to lick her pussy zeroing in on her clit but not focusing 100% of my attention on it. I went down and in her hole and back up to her clit. This is exactly what she liked. I could tell she was about to cum as her body started moving more rapidly. I put a finger in her pussy as I continued to lick her clit. She moaned pretty loud as she came and her knees almost buckled.

We cleaned up a bit before it was my turn to get some pleasure. I never got fully flaccid as we washed up but was starting to get fully erect again as she grabbed the washcloth and started cleaning my dick and balls. She licked and stroked it in between washing. I couldn't stop picturing Melanie naked as Jennifer teased my dick with her tongue. I stood her up again and bent her over. Her hands were placed on the step we have in our shower. I was so turned on thinking about Melanie I didn't think I'd last very long. As I guided my cock into my girlfriend, I was thinking about that well-manicured red bush of Melanie's. I rammed it in thinking about Melanie's fine ass. As I started going in...and out...I was mentally replacing Jennifer's sandy blonde hair with Melanie's long red hair. I pulled on it a bit. Then I reached around and grabbed Jennifer's right tit as I thrust back and forth. I was remembering Melanie's asshole staring down at me while she put the sucker into her pussy. The memory had me staring down at Jennifer's asshole as I continued to thrust my dick into her pussy. I took my hand off of her tit and started working my wet right thumb into Jennifer's tight little ass. I've never done this to Jennifer but she didn't seem too phased by it. I continued to work it into her ass as I continued to thrust back and forth into her beautiful pussy. I was getting close and could tell she was ready for her second orgasm of the night.

"Stick it in my ass!" Beautiful Jennifer surprised me.

"Not now!" I could barely muster as I started to shoot my sperm into the walls of her pussy. I filled her up like I don't remember ever doing. As I shot loads and loads she started to cum as well. We both continued to thrust until we were both spent. When we were done I told her that I never knew it was an option but would love to screw her ass next time.

Chapter 3

The day had arrived! The package showed up at my work. Now I needed to plan the show.

I texted Melanie immediately. "When can we meet? I have something for you."

"I'm off at 2pm today." She responded.

"Meet me in the loft at 3. I can't wait to see how it looks on you." I replied.

I left work early. I owned a pool cleaning and maintenance service so I set my own hours. I had 7 employees that went out on pool jobs and one secretary/dispatcher. So my flexibility was pretty great.

I got home at 2:15 and didn't see her car yet. I took a quick shower. I really didn't know what to expect today but knew it would at least involve my renter and she'd be naked. The $90 plus shipping I had spent on her lingerie was nothing compared to the fun I was having. I was hoping that she'd use me as her sucker this time around but with her being so unpredictable, I just never knew what to expect.

I went up to the loft a little after 2:30 to prepare. I had decided, after weighing all of the pros and cons, to place a couple of hidden cameras in the loft to capture everything for my pleasure later. Once I had both of the cameras set up and recording, I just sat at my desk and waited. I kept looking at the cameras to make sure I had them hidden well enough. One I place on my bookshelf underneath a tilted book that rested on another. It was behind my desk and was facing towards the couch. The other I put at the end of my bar just behind a clock I had setting on it. I figured both would capture most of the room. I was starting to get turned on staring at the two Victoria Secret packages I had and thinking about what was coming next.

She walked in a minute after 3. "How was your day?" She asked nervously.

"It was fine. But ever since the package showed up I've had one thing on my mind." I smiled. "Go ahead and open it." I pointed to the one and moved the other to the side.

She looked at the package and started to open it. She left the gift totally up to me to choose. However, she did request that it be for both the top and the bottom so I kept it simple. I bought a nice black and lace push-up bra and black lace boy shorts. They weren't from the same collection but I noticed they matched perfectly as she pulled them out of the box. She looked at them and smiled. "I love them!" She exclaimed. "I've never had this nice of a bra before!" She came over and planted a nice kiss right on my lips. "Are you ready for me to try them on?" She asked.

"I've been ready since we first talked about this!" I could barely stand it anymore.

She was wearing the most I've seen her wear since we've been this up close and personal in the past several days. She had on her work uniform, but she definitely smelled like she took a shower after work and her hair was slightly wet. Her work uniform consisted of a polo shirt and black pants.

She slowly started taking her pants down first. "Take it all off first before putting the lingerie on." I demanded. Her pants hit the ground. I asked her to turn around as she took her underwear off.

"Can you bend over towards me as you pull it off?" I asked just hoping the camera behind me was at the right angle. Without saying a word she started to bend over as she pulled her underwear off. I was treated to the beautiful sight of her exclamation point and pinkish starfish. I wanted to be in one of those holes shortly. I wasn't sure which one though.

She finally stood up and turned back around facing me. She started taking her polo shirt off and didn't have a bra on. Her tits looked amazing on her body. Her ex was correct, one was slightly larger than the other, but that seems pretty normal to me. And they didn't look bad at all. They were very proportional to her body which is key in my opinion. I could tell she was nervous with her top off in front of me again. "They are beautiful. You are beautiful!" I said. And I was telling the truth.

She walked to the box that was on my bar top and took the boy short panties out. She slowly wiggled it up her body until it was perfectly fitted around her ass. She turned around, slapped her cheeks with both hands and asked, "How do they look?"

"They look like a million bucks on you!" I responded.

She turned back around and smiled. She grabbed the bra out of the package and started to put it on. I just sat there at my desk and admired the beauty that was in front of me. She wasn't naked anymore but I was bulging out of my shorts.

"And how does this look?" She asked as she snapped the bra on and settled it in place.

"Also a million bucks. You are one beautiful woman! I can't get you out of my mind!" I admitted. I got up and walked past her and sat on my couch.

"I can see you like it!" she pointed at my hard cock. She started walking over to me. "The question is- do you want more than just a show?"

"Of course I do! I'm not an impotent idiot!" I answered. I pulled her towards me and she got down on top of me straddling each of my legs. She was now facing me sitting on my lap. I pulled her head towards me and kissed her on the lips. She responded and opened up her mouth to kiss me back. I grabbed her ass cheeks with both hands as we continued to kiss each other. She reached down and got her first touch of my cock and she rubbed it back and forth from outside of my shorts. After a few minutes she slid off of me onto her knees. She pulled my shorts down exposing my large erection. She immediately started sucking my cock and it felt so great. She stroked me, and then sucked me over and over. Her beautiful red hair bobbing up and down on my cock was almost too much to handle. She was a master at sucking cock and I was about to explode. I pulled her up before it was too late and stood up. I took my shirt off and unlatched her new bra. I discretely turned her body so the bar camera would be getting the best view. I started sucking and licking on her right nipple as I fondled her left tit. She was breathing deeply now. I could tell she was getting turned on. I slowly moved her towards the couch and pulled down her new underwear once again exposing her beautiful trimmed pussy. She sat down and it was my turn to get on my knees. I started teasing her like she had teased me the last several days. I slowly ran my fingers up her inner thighs until I got close to her entrance and then I'd back away. I did the same thing with my tongue. As I got close to her pussy she would move her hips forward but then I'd just back off. She tried pulling my head towards her entrance but I fought it. After a few long minutes I finally lapped at her pussy. She tasted great. I used my fingers to spread her lips apart a bit and was able to zero in on her clit. I tried the same technique with her that I use on Jennifer; she seemed to like this. I worked her clit in a circular motion and could tell all of this build up was doing the trick. After a few moments she started moving violently and moaning pretty loud. Her juices started flowing from her pussy as I continued to lick. She finally let go of my head a bit so I could move and get some air. The look on her face was of pure ecstasy. I kissed her and gave her a taste of her own juices but it didn't faze her. She looked again at my rock hard cock and asked if I wanted to find another hole for it. I laughed and responded, "Let's get you bent over this couch and we'll see what it decides."

I helped her stand up and she knew the position. She went to the edge of the couch and placed each hand on the armrest and bent her body. I got behind her and started rubbing my dry cock in her pussy juices. I got it wet enough to start entering her pussy. She pushed back as I entered and we got into a good rhythm. She moaned and groaned as I continued to thrust into her. I would pull my cock out to the tip and then jam it back in a little roughly. This seemed to turn her on again. As I worked her pussy I licked my thumb and started to work it into her ass just like I did with Jennifer. I had no doubt this ass has been used before because she didn't say or do anything when I got my thumb in there. She just continued to groan in a good way. I continued to work it until I buried it completely in. The angle wasn't the best for any of my other fingers so I decided to just go for it. I pulled my dick out of her pussy and started to work it in where my thumb was. I used her pussy juice for my lube and it seemed to work after a little bit. As I entered she let out another deep moan. She started to finger herself with her right hand while balancing on the couch with her left. I was just hoping that the cameras were getting all of this! I rocked my dick in her tight asshole back and forth and she loved it. I knew I wasn't going to last much longer in this tightness. Luckily she started writhing again so I knew she was going to cum again. As she started to yell out I started shooting loads of cum into the walls of her ass. Our orgasms both seemed to build off of each other's and we were both moaning louder than would seem to be normal. Her ass milked my cock completely dry of all cum and we finally both started coming down from our high. I pulled out of her ass and glanced down at the temporary gape that I had made. We collapsed on the couch both naked and spent.