Fooling Around With The Landlady

When my wife's at work I fool around with the landlady. She's 50 and not really attractive but she has a hot body that she knows how to use. I'm 28 and said by the ladies to be good looking and have a sexy body so that's probably why the landlady hit on me. Because I like cougars I got it on with her. Now I fool around with her every day while my wife is working. I don't have to work. My wife makes enough money to support us and it's kinda cool to be able to hang around and not have to bust my butt on some job or take any crap from some lame boss. Prudes would probably call me a cheater. I'm no cheater. It's not like I've betrayed my wife with my love. This thing with the landlady is just about two people having some harmless s** together and not about any love. If my wife knew about me fooling around with the landlady she'd probably get the wrong idea and think I was betraying our love. It's not like that. I'm just having a little fun and giving an old cougar some hot morning delights and there's nothing wrong with that.



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  • Humans are not meant to be monogamous. My wife and I have an open marriage and enjoy recreational s** with several friends. No jealousy and lots of fun.

  • I had a tenant that took very good care of the property but failed to pay on time. One day I went with my wife to try to collect and both my wife and I noticed how he stared at my wife. The next month my wife asked me to let her collect the rent herself. It was great. He paid in full and on time. From that day on my wife is the official collector.

  • I just started renting this room and the landlady (owner of the house) and I are almost same age. I am in the process of a divorce and she is a single mom. We got along right away and it’s one of those things that you’d know right away that in time it could lead to some physical attraction and longings. We started getting comfortable talking, texting each other and one night we both were willing and tested the waters. It was one of the best s** I’ve had in a long time and it could grow further but I feel not ready

  • My wife is the landlady. We have several rental properties in the inner city. Our tenants are not good payers. My wife has very good people skills so she took charge of collections. She visit with every tenant about once a month. Sometimes I drive her and wait outside while she does her job. Sometimes is quick but sometimes it takes her longer so I drop her and go run some errands to pick her up later.

  • I was a very shy student. My landlady, a chubby widow of 63, got me over it by teaching me everything to pleasure a woman. I didn't regret it a moment.

  • Been ther, done that, my landlady was early sixty, a buxom woman who was eager to please a young 19 year old student in those days. Never too tired and never said no to a h****, hungry young man like me.
    After study I've spend another year with her untill I found a job in another town.
    She must be ninty something today.

  • My chubby landlady, a hispanic widow of 66, seemed to be as much hot for a young student, as I was for my landlady, when I moved in with her.
    It was in the second week she asked me to join her in her bedroom and i. The five years, I lived with her, I never sleeped in my own bed.

  • My landlady is 65 and very plump. When she goes out I raid her soiled underware basket in the bathroom. She wears xxl pantygirdles and the gusset is something to die for. They are so crusty from her dried juices. When I rub the tip of my c*** on them I c** right away. I know she changes them evey 5 days and the stench is so sexy. The back end has light brown skidmarks. Same goes for the gusset of her pantyhoes. Her bra's smell of sweat as these don't get changed for 5 days. I pump them with my seed I'm sure she knows. I hope she catches me and puts me over her knees for a good spanking.

  • I had a landlady I wanted to f*** so bad. She always wore clothes that hid her smoking hot body and was too proper to get anything going with. I always wondered if under all that prudishness she was a wild woman in bed. I regret I never got any of that.

  • My landlady is no one I would ever want to fool around with. She is in her sixties and unattractive to me.

  • How how h**** it would be if you've tried. I did and my landlady was awaysome!

  • Closest I ever came to s******* a landlady was when I peeped in her window and saw everything. I was too chicken to try anything and she had a big bad looking husband. He looked like a freakin' gangster.

  • When I was in high school (loooooong ago) I lived with my mother in a four-plex owned by another lady tenant. I used to help out around the place doing maintenance and such, and one day I was in the yard with her working on some azalea bushes and she sent me into the house to get a bucket. I went to the wrong closet by mistake and came across a box of s** toys that included the four biggest d***** I have ever seen in my life before or since. The thought of her using those monsters on herself drove me wild with desire for her so I tried flirting several times after that but I never told her what I saw and she never responded to my flirting so nothing sexual ever happened. I still think about her to this day and I wish I could have done her.

  • Man, that is hot. I would have felt the same way. Cool to have seen a bit of her hot sexuality. Often you can't tell how wild in bed a woman might be. She sounded like a firecracker.

  • This is my fantasy. I want to do my landlady. She wears tight pants and low cut blouses and is so hot. I saw her bend over once and oh my god her t*** looked soooo good. She is too damn proper to fool around though. I think she might have some lesbian in her, she pays more attention to my wife than me. I swear I saw her checking out my wife's body a couple of times. I joked with my wife once about a three way with the landlady, but she was not into that idea. Sometimes a guy just cannot win.

  • I would like to do my landlady's hot daughter who is a student at a big name college. She is so f****** stuck up she will not even say hi to me. But she has nice t*** and a sweet ass. I have seen her naked. Her room is in the landlady's house across the street from my apartment. Thanks to some good binoculars I got a great view of her undressing when she came home one night late and probably had been drinking with her snooty college girlfriends. I keep hoping she will forget to close her blinds again. So far no luck.

  • You ain't no player. A player would have gotten that by now.

  • You are right. A player I am not. I don't have the b**** to try harder to get with her.

  • STFU you G******* loser and get a job. No self-respecting man lives a life like yours. Either straighten up find a means to support yourself or go jump off a bridge. Guys like you are pathetic and a disgrace to real men everywhere.

    I'm assuming your dad or whatever male figure you had in your life as a child is dead or a low life slob like you. That's the only two possible reasons why he hasn't slapped the ever loving s*** out of you.

  • Been there done it. Married it.

  • I wanted to bang a landlady I had once. She had a hot body, but didn't want anything to do with me. You can't win them all.

  • When I was 18 I stole some candy out of a candy store. I coulda bought it but it was way more fun stealing it.

  • Suck ... my ... t*** ... B******!

  • You f**king a**holes are ruining Confessipnpost. Post your crude fake s*** somewhere else!

  • Suck it p**** boy!

  • I am 18 now, about 2 years ago I watched a friend self suck himself , it appeared to be so easy and hot. His p**** was no bigger than mine , but he was good at bending down . So When I am alone I have been experimenting and have found it to be safe and fun and not really hard at all . So many girls lost their virginity to idiots and so many get pregnant , stupid b****** know all about birth control, so do the guys , you have to assume they want to be pregnant with some ignorant ass. Now I have all the s** I want without even dating . The girls say I am good looking , but I am not about to touch those stupid b****** . Nothing wrong with dating but frankly I refuse to go out with many of the whores in my area . I don't think a single one is a virgin , and for sure they are so stupid . Self sucking his hot and easy and fun , why did I wait so long to try it ?

  • The meatspin poof hates that s***. Says it's not the same as sucking foreign c**** and getting shagged.

  • that meatspin vid is the total bomb!

  • Is that all you got?

  • I got the hots for my landlady's daughter. My landlady is in her sixties. Her daughter is in her forties and still a looker. One time I had to see my landlady about something and her daughter answered the door. I could tell she had no bra on. She didn't do it on purpose. She has no interest in me. It was nice though knowing she had no bra on. From what I could see her t*** looked nice and full beneath her blouse. The landlady's daughter only visits about once every three months and stays a few days. I wish I could say I slept with her. At least I got a nice view. Women look so hot when they don't wear their bras. Ever notice how in their homes they are less guarded about what they show? I love that.

  • This just in for Oooooo THE WRITING POLICE. Taaa daaa:
    I'd like to see things from your point of view but I can't seem to get my head that far up my ass.

  • My next door neighbor is driving me crazy. She undresses at night in front of her bedroom window without pulling down the shades. I am 90 percent sure she is doing it on purpose. I am careful not to let her see me looking in case I am wrong. I don't think I am. But who knows? I have seen every inch of her luscious body. Her t*** are perfectly proportioned for her petite body. Her ass is to die for. She looks a little like Reese Witherspoon except she has brown hair. I would so enjoy getting some of that. But there are two problems. She is married and her husband is a cop. He works nights, which would give me free time to play with her, but he is big and muscular and looks gangster mean. No way would I mess with him. I am just a student he would crush in seconds. Because of the threat of him kicking the s*** out of me or worse, I have to be content with just watching his gorgeous wife's nightly shows.

  • I'm pretty sure she does it on purpose too. Ever since I saw Porky's, I've kept my blinds at least a little open. Don't ruin it by saying or doing anything about it. I HATE it when it is shoved in my face.

  • Hahaha

  • I totally admire what you're doing, and I'm reeeeeeeeally envious, too. I've never had anything like your situation, but several years ago, my wife and I moved into this condo right after we got married and it was owned by this married couple. The wife was hot as h***, and even tough I never got her, I did have an affair with her best girlfriend the entire time we lived at that condo development. That woman (58 and married) was the nastiest f*** I've ever had: nothing was off limits with this b****, just like your cougar. To this day, she was the only woman I've ever been with who went ass-to-mouth. And she did it without even being asked: she just loved how filthy it was. And she also asked for regular golden showers. Naturally, I obliged her on both counts. :) We kept the affair going even after my wife and I moved out, but eventually we had to end it because she and her husband moved out of town. The b**** was amazing.

  • your right its not cheating because its not love between you and her. thats a really great point.

  • But good as you and the landlady are together, isn't it just possible that your relationship with her could BECOME love???? Is it possible that it already is?

  • My landlady is a hot piece of cougar tail and I wish I could get with her even half as good as you are with yours. H*** even ten percent as good as you! She is nasty but I haven't been able to get on it yet partly because my wife is in my way. You go!!

  • OMMFG! This is one of the sexiest things I've ever heard or read. I totally love how overheated and hungry and wild and nasty the landlady is, and I love the fact that she's so willing to give you anything and everything ALL THE F****** TIME. That is a real woman you've got there and I really do hope you never lose her. I suppose that means I'm encouraging you to be careful you don't get caught by your wife, but honestly, the more I think of it, the more I think winding up with the landlady full-time, and your wife entirely out of the picture, is your best-case scenario. That's for sure the one I'd pick. But no matter what happens, dude, YOU ..... ARE ..... THE ..... MAN!!!!!

  • sooooooooooo f****** sexy!!!!!!!!!!!!!!!!

  • Is the landlady really as hot and nasty as she sounds?

  • You know it, brah!

  • How is a woman like a condom?
    Both spend more time in your wallet than on your pecker.

  • Just a couple questions if you don't mind..... Of the two of them, which one has the better p****? Your wife or the landlady? And which is the better overall f***? And which one do you f*** more often? Thanks! Signed, an Envious Fan.

  • The landlady is no looker compared to my wife, but what she lacks in looks she makes up for with her hot curves (and bigger t*** and longer nipples than my wife and her ass is still breathtaking and she has mindblowing bedroom skills and she even has s** toys!!!). My wife is conservative compared to her. She finds oral s** disgusting, unfortunately. The always h**** landlady is like a guy's dream of the perfect woman for having s** with. The first time she approached me, I didn't want to fool around with her. I had morals and didn't want to get caught by my wife. But, when the landlady said she would do anything I wanted to do in bed and winked at me, she got my attention. All day I kept thinking about her doing anything I wanted and all the things I wanted to do with her hot bod. The next day she approached me wearing a robe with nothing on under it. When she flashed me and put her hands on me I was too weak to resist her. And, wow, she was like a s** starved wildcat who hadn't been with a man in years. I had to go back for more and more and more. I know what I'm doing is risky, but I'm hooked on my landlady's hot s**. Besides, you only live once and might as well live life to the fullest.

  • i know you do the landlady when the wife is at work but do you ever find yourself wanting her at night when your in bed with your wife and so you get up from bed and go get the landlady in her bed? and while your wife is at work do you ever f*** the landlady in the bed you share with your wife at night? another fan.....

  • wife dont like oral s** either, so i get it head from chicks at work

  • You are living the dream doing two ladies night and day. I salute you, Super Stud!

  • hot as h***

  • Keep it going.. i am hooking up with some chicks at my work and i dont feel bad about it cuz its just s**, so if you can get some p**** from this lady, dont stop

  • "I don't have to work"? You are a lazy useless m***********. I doubt you know much about what your wife is doing. I hope she's f****** around too. Useless p****.

  • Hear this, thou Amalekite dog, for you will be pursued into the mountains by s**-mad baboons!

  • My, my, my. What an extraordinary coincidence that this person's writing is the same as the OP. Could this be one of the nefarious MEOW's many masquerades? -The Writing Vigilantes

  • I sure wish I had a guy here to give me a hot sexy massage right now. I am h****, wet and naked as I sit at my computer with no man to massage me and take care of my needs.

  • Oh, Baby! I'm all in. Where you at???

  • This confession made me wet.

  • Sweet. I wish I had a thing like that. That way if the wife wasn't in the mood, I'd tap the landlady. Because you have your wife out all day working, you will probably be able to keep your double dipping going on for years without her finding out. But, don't make the mistake of telling her what you are up to. Don't ruin a good thing.

  • The Difference Between Small B****** and Large B******
    Women with big b******

    ..can get a taxi on the worst days
    ..have a neat place to carry spare change
    ..have always been the centre of the arts
    ..make jogging a spectator sport
    ..can keep a magazine dry while laying in the tub
    ..usually can find leftover popcorn after a movie
    ..always float better
    ..know where to look first for lost earrings
    ..rarely lack for a slow dance partner
    ..have a place to set their glasses when sitting in an armless recliner

    Women with small b******

    ..don’t cause a traffic accident every time they bend over in public
    ..always look younger
    ..find that dribbled food makes it to the napkin on their lap
    ..can always see their toes and shoes
    ..can sleep on their stomachs
    ..have no trouble sliding behind the wheel of small cars
    ..know that people can read the entire message on their t-shirts
    ..can come late to a theatre and not disrupt an entire aisle
    ..can take aerobic class without running the risk of knocking themselves out.

  • she sounds like an incredibly hot piece. enjoy!

  • I had an eight-year affair with an older married woman that my wife worked for at her job, and it was the best s** of my entire life. I would never have ended it, but her husband got transferred to another city, so we had to stop. I went to see her a couple times in the following year, but by then she had begun a relationship with an even younger guy who lived in that area and who could give her the service she needed so she didn't need me anymore. I've looked for another older gal here where I live and have been with a few but nobody who was nearly as good as Cheryl or who was nearly as discreet. I hope yours last forever.

  • I lived with my landlady when I was 19yo. Coming home early one day I surprised her when she was nude. I couldn't look away, it was the first female bar none I had ever seen in the bollocky. She said now you've seen my bare bottom, I 'm going to look at yours. Thinking I was about to lose my virginity I tugged my undies down quick smart. All I got was a bare bottom spanking

  • Wow. You are the Man. I wish I could get away with messing around with two women. I envy you. You are living life to its fullest. I don't even dare try that for fear my wife would catch me and make my life a living h***.

  • Seriously, Dude, the landlady should give you a break on the rent for your services rendered. If you're any good at fiddling around with her, she should cut your rent in half, at least.

  • You keep believing those delusions right up until your wife leaves your ass when she finds out.

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