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3
Anonymous
@confessions
27 Feb 2014 6:11PM
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I recently moved in with my GF after dating for two years. It took us a while to find a place in our price range, we wanted to rent a house, but had to settle for a condo.

Our landlord is a cougar MILF, recently widowed and owns her own business. Ive only seen her in business suits and its so sexy. Usually pencil skirt suits with high heels.

Right after we moved in we let her know about a few things that needed to be fixed. She was fine with it and said she would come over to let her maintenance guy in. I completely forgot to put away my bong.

I got a text at work of a picture of my bong reading "I think we need to talk" from my landlord. I wasnt sure what to do, but I told my boss that I was going to have to take a long lunch but I would work late to make up for it.

By the time I got home the maint guy was leaving and she was looking sexy as fuck in her suit but I was nervous that she was about to kick us out.

I'll spare you reading the whole convo but basically she said she would ignore the fact that Im smoking weed in her place if I was her bitch. I didnt really have much of a choice but I told her my GF couldnt find out. She agreed.

She likes having me come over to her place and as soon as I walk in the door we roleplay as mom/son.
She likes to spank me, tease me, stroke my cock, finger me, suck me off, make me eat her out, fuck me with a strapon, and if I cum in her before she tells me to she makes me lick it out of her. Sometimes she likes to just sit on the couch and watch TV while she breastfeeds me.

At first I hated this but I'm actually starting to love it all.
Im even starting to take control of the situation and initiate a lot of the stuff we do.

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Anonymous
@confessions
22 Dec 2016 11:55AM
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I confess, I fucked a secretary in our company. Sylvia is a smoking hot cougar. She has an incredible body for a woman her age and takes very good care of herself. She never had any kids, so I guess that makes it easier. She also has a very classy yet sexy way of dressing for work everyday.

She is as sweet as can be. Always smiling, eager to be helpful in any way she can. One of those positive spirits that, coupled with her stunning looks, makes you want to fuck her. And yes, I have masturbated in the men's room a time or two because looking at Sylvia got me so horny.

We have worked in the same company for 10 years, so we know each other pretty well and are quite comfortable with each other. Our interactions were always professional. I said "were".

I heard from other guys in the office that Sylvia is a crazy flirt. She was never flirtatious with me, maybe because I am one of the big bosses. And because sexual harassment lawsuits are so common, I have never wanted to cross the line into unprofessionalism.

Well, I decided I'd experiment a little. I started to compliment Sylvia whenever she came into my office with something. I had to sign expense accounts and she often prepared them for the sales guys, so her visits to my office were almost daily, though very brief.

I'd say things like, "You look amazing today.", or "That is a stunning blouse you are wearing." or "I love those glasses." and "That hair style looks great on you."

She loved the compliments so much she started walking in and asking, "How do you like this shirt?" or "What do you think of this neckless?" Eventually, her questions got to "Do you think this is sexy?" and "Do you think this is hot looking?"

Then one day she took those daily exchanges to a whole new level. As she was walking out of my office, she turns her head, looking over her shoulder at me with her hand on her hip and asks, "Does my ass look good in these pants? I'm not wearing any panties." I just about dropped my teeth. She walked out with a devilish grin on her face.

From that day forward, she started to get more bold in her approach to me. A few days later she is wearing a white, button down shirt that is sheer enough that you can see she is wearing a lacy bra. She walks into my office, puts the expense reports in front of me on my desk and asks if I can sign them right away, as she waits. I, of course, comply.

As I'm looking over them, she leans over placing her hands on my desk and asks, "Do you like my neckless?"

I look up, and her neckless is hanging perfectly in front of the cleavage between her breasts and I can see right down her blouse at those magnificent tits. I smile ear to ear and nod gleefully. She asks, "Do you like anything else that you see?" All I can say is, "Oh yes." She then says, "I wore this shirt just for you today. The lacy bra is a little extra I threw in for your viewing pleasure." I can't stop smiling. I can feel my face getting beet red. She then turns and walks out with that devilish grin on her face again.

Later that day, I have to leave the building for a meeting. As I step out of my office she says, "Are you leaving for the day?" I tell her yes and she follows me to the elevator. When the elevator door opens, it is empty and the two of us step in. When the doors close, she turns and plants a passionate, lingering kiss on my lips. The door to the elevator opens and she exits saying, "Have a nice day." with that devilish grin again. I am blown away and she is all I can think about for the rest of the day and night.

I'm an early bird and always get to the office by 6 am, way before anyone else does. It's my most productive time of the day before others start arriving by 7:30 am and fills up by 9:00 am. Everybody in the office knows my routine.

The morning after the elevator kiss, I'm in by 6 am as usual. About 6:15, I hear the unusual sound of another person entering the office. I hear the elevator bell. I hear the sound of footsteps on the hard lobby floor. I could hear some shuffling at a cubicle common to one arriving for work. I note that it is unusual so early but keep working at my computer that faces away from my door.

The next thing I hear is "Good Morning" in the sweetest, seductive tone. It is Sylvia at my office door. I turn around in utter shock. There she stands in my doorway wearing one of those wrap around dresses that is propped open by her hand on her hip as she leans on the doorway with her opposite shoulder. It was the most seductive, sexy pose. She is wearing the sexiest lace bra and panties. Her tits are huge. I am speechless.

Without saying a word, she walks in, closes my door, turns off the light, walks behind my desk, spins me around in my office chair, kneels down in front of me and starts undoing my belt and pants. By this time, my cock is rock hard. As soon as she pulls it out of my pants, she goes down on me. Once soaked in her spit, she draws back, unsnaps her bra at the clip between her tits, and starts giving me a titty fuck while looking up at me.

No words have been spoken. The only sound is heavy breathing and moans. Once done with the titty fuck, she stands, turns around facing away from me, lifts her dress to expose her ass, reaches around to pull her panties to the side, and lowers herself down on to my cock.

The sensation of her pussy fucking my cock was amazing. I've never seen a woman get so wet. My cock is quickly covered with her creamy wetness. I can't believe this is happening to me.

I whisper, "I'm going to cum, I'm going to cum." She quickly stands up, turns around, drops to her knees in front of me, looks into my eyes and says, "Cum in my mouth." Down she goes and boom, I explode in her mouth.

She took every drop of cum and kept sucking until I was drained. When it was clear I was finished and my cock already starting to soften, she stands up, straightens up her panties and bra, quickly closes the wrap around dress as if nothing had just happened, looks at me and says, "I like a certain kind of cream in my coffee. Now that I've had it, can I bring you a cup?" I nod in agreement, she turns to walk out, blowing me a kiss.

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Anonymous
@random
28 Aug 2015 11:21AM
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So let me tell you about how I got to know this cougar before I start my story.


I met this awesome girl when I first moved out of my house, I was couch surfing and what not but she was the first one to get me out of my comfort zone And into my more current lifestyle of not being bound to one thing or ideal or way of life what ever. Anyway I was with her for about a year before we split up up she had a boyfriend and a girlfriend and was messing around, by the way this girl is the healthiest hippy girl there is the reason is say that is by the age of sixteen she could look at any plant and tell you what it was and what it's used were. She wouldn't let me wear a condom so she could pleasure herself and not taste the latex or live I had a pregnancy scare towards the end of our first year together but it was that time I was still young and dumb and thought hey I would love to start a family, I realized that especially when I started looking at pregnant pornstars more often and for a while just got into that and that only. Any way about two years ago we split up after the second year of us being together it was about three or four months later I heard she was pregnant with some hawaiian asshole that still fucks her over on a day to day basis. Needless to say I was livid, anyway during this time I was in contact with her mom because she live 15 minutes away and she loved me I was really nice respectful and was good with her youngest daughter.

Anyway after all this I started talking a lot with her and one night she was at a reunion got really drunk and couldn't drive home so she called her daughter my ex but still best friend, and she called me to pick her up. Any way I didn't say no cuz I had nothing better to do I went picked her and her daughter up and drive them home, me and her mom were talking and having some tea and waited for the yougest daughter to go to bed anyway once that happened we started getting closer and I started twirling finger across her skin, and she didn't do anything, I started moving closer to those places that you wouldn't normally go for she's not the greatest looking mom but she does have her own beauty she is still really young at heart she acts like a young twenty year old when I talk with her, and (just so we are clear this lady's daughter, my ex, was 16 when I first met her and she was on the street for about a year when I met her. Her mom is pushing sixty which is how old my mom is turning,.) any who I started fondling her huge tits for a bit she looked at me with a really innocent look and I instantly saw her daughter there in front of me and thought this would be an awesome future wife. I kissed her once and she was kind of hesitant but she looked at me again and grabbed me and we started making out really intense like a lot of pent up passion; I hadn't been laid in like six months her I don't know how long, any aT it was intense she was wearing this button up under shirt one piece that goes under her dress and I couldn't figure it but before I could say anything she had already unbuttoned it. I got on my knees and started eating her out like I haven't ever eaten out before it was like an all you can eat buffet after smoking a quarter ounce with your homies, she was super bushy like she hadn't shaved or even trimmed in like a year. But I'm down there for about a solid 10 minutes when she squirt right in my face all in my mouth, I drank what I caught and looked at her in her eyes and she was super embarrassed I happened to ask the right question at the time and ask her if she's ever squirt before and to my surprise she said no, 😮 what!! Anyway I kept eating her out and fingering her I started pressing on her lower abdomen and hiring that g spot made her go crazy she squirt like 5 Or 6 times by the time I got done with my foreplay she looked at me when I had decided to stop and give her a break I for some reason asked her if she was wanting what I was wanting and she started undoing my pants which was the biggest fantasy of my life to have someone undress me the way I want to undress beautiful people on a regular basis. My Vick is rock hard she leans back and spreads her legs a bit and I start teasing her clot with my cock, she was soaking wet still so every pass I mad over clitoris made her shake like she was riding a sybian, after the first few passed I went for it and put it in. The sex it self didn't last that long maybe 10 minutes but it was hot she squirt all over my cock it was like a dream come true for a pervert like me. Milf my ex gf s mom at that after she got pregnant all my aggression was reappeared by one deep load in her mom. Before I started playing with her I asked her if she wanted to do this in the shower but she said no and that shed do when she wanted to clean up after wards so after wards she got up and the couch cushion was soaking and she went to the shower and I flipped the cushion and followed her in and took a shower with her before I went home, I had such a hard time leaving, and I have an even harder time forget and reliving that night when I jerk off it always gets me off. This was probably the best pussy I have ever had, (ahhh...top three) and it is the reason that I think I have a hard time connecting with women of my age. The last time I had sex was 8 months ago and she was a bbw into bondage and stuff but it was a very open relationship but she had the same body type as my ex's mom and she had the wettest pussy I've ever fucked consecutively in a regular basis but I still thought of my ex's mom while fucking her for three four hours straight. (by the way that was the longest time I had ever lasted and not cum, she was sore and just couldn't keep going so I stoped she sucked me off and I got to throat fuck her till I came, she's a swallower by the way,

Any way that's my white night story in my gf revenge story and in till recently we still wanted to get together again and do this, the one day I guess I got hammered and sent her a dick pic and the next morning got blown up by her, which is understandable. Because getibg an interested dick pic is a very innapropriate thing to do at the very least but it's also very threatening in a way. Regardless I was super ashamed and just didn't say anything to her after that and it's been radio silence. Should I get in touch with her and appologise and make up I know I was in the wrong but I mean that's something that she'll be reminded of about me that's what I've done and and all that but I mean we've fucked so do you think she's like super posses or just upset that I sent that innapropriate photo to her at the time. Eh I've just been really interested in some of the pervs in this site and this has been go to place when I get in motherless is the post board and read a few stories to see something new or hear a story or someone's sexual encounter. I've been a motherless member for a bit till I posted some of my ex gs pictures on here full name and area code and she sound out that it was me somehow and threatens to use me or send me to jail. Anyway I freaked out shut down my account and kept anonymous for for the rest of my motherless career in solo pleasure. It was x videos for basic poem at first then I started searching around and I heard one of my good friends that I wound up us being a huge crush on had an ameture porn video with one of her friends at the time and it got out up but that was when motherless was really no restriction poem that's when beastiality was still on here and after I found this place it was my porno haven, regardless now I'm living in Santa Barbara lonely as fuck and looking for fun down for trans or buff guys with big cocks and any beautiful women I'd like to fuck a black woman and get the experience with the right booty that slaps your groin when she's riding your cock and a girl who will fill a glass that I can drink with squirt. Someone who's down to get kinky. Like I'm a bit of a closet bi but that's due to the fact that I'm just not nearly attracted to guys as much as I'm attracted to stunning dimes. Which there are a lot of in Santa Barbara. Anyway anyone want to get freaky leave a way to get in touch your name your toe whatever Skype I won't ask for the phone number of post my info on here, and if you do send me your info after I get it I'll delete the comment. Or you can delete the comment. I'm down to host or if you want to get a hotel I get discounts at any minor in hotel for a night and both of the restraint hotels are 4 stars but are the top rated hotels in the world.

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Youngbbc513
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@hookups
02 Oct 2019 10:38AM
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Looking for older women into younger guys
I'm 20yrs old BBC
Please no one older than 50
I am into milfs and cougars nsa or I can be your boy toy I work two jobs and 420friendly
Smoking cant be a problem

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Sonikku92
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@confessions
04 Jan 2021 8:31PM
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I must admit that new year's was crazy, my neighbor is a smoking hot 55 year old cougar at least in my book, I'm always helping her when I can she's okay with me dressing as a girl and stuff, I went over to offer her some cookies I got invited in then... Mind you she's divorced and alone she asked to fuck me said I was adorable, I agreed it started out sucking her breasts which made me hard quick she was my first girl, she left the room a moment later like some crazy porn movie she had a strap on a big one told me to suck it so I did till she bent me over the couch pulled my skirt and away my panties I felt the to on my hole, she said take deep breath and then entered me finally I lost my anal virginity I moaned the loudest I'd ever moaned she jerked me while she fucked me silly, I came all over her couch she made me lick it up, then it was her turn it felt like hours on my knees the TV on as she sat there legs apart I ate her pussy her moans turned me on again I couldn't help it, she didn't notice but I placed my cock between her folds my first pussy she moaned again surprised her thighs held me in place I felt her climax once she squeezed me so hard till exploded inside her, after she said come by more often, feel free to walk on in if I please I don't know what this means but, hopefully it's a regular thing

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