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5 months ago inmilfbyAnonymous

My friends mom

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I (m21 at the time) went to my family friends for a get together. We’ve been friends since we were kids and I’ve never thought of his mom (f42) in any sexual way until I saw her in a slim bikini.. it squeezed her chest and ass so tight I thought it would rip. I would estimate a DD for her size, slim figure with a cute face and lips that would make me have to adjust myself every bit and then. I always fantasized about her giving me head.. And after that moment, I began to deviate.

I’m not so bad myself. I’m 6’3”, 175lbs, athletic build, and an 8 inches hung. (Dm for pics)

I went over for a family friend gathering and decided to wear some swim trunks that gripped me a little bit once they got wet. I went in the pool to relax and thought of her. I waited until I was bulging and showing off a chub before she came out and offered me water. “Oh thank you Jane! But I can manage, I was just getting out.” As I stepped out, my heart started thumping. She looked, her eyebrows raised, and her mo... continue reading

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This naughty story took place last summer. Now, the pool season starts again and I think I will be able to have a great time again. I leave it here and I await your advice. I live in a not very large housing estate, about a hundred neighbors. And in summer I like to go down to the pool to sunbathe. The rules are that you can't go topless but usually a lot of people don't come and sometimes I found myself completely alone and take advantage of it. If I see someone coming I put on my bikini and that's it.

But one day when no one was there, I fell asleep on the lounger. When I woke up in the water there were a couple of guys. One of them was the couple's next-door neighbor and the other a visiting friend of theirs. I realized that they were looking at me sideways and I pretended to be asleep. They couldn't stop looking and laughing. In the end they got out of the pool and sat nearby. I took advantage of the situation.

\- oops! Sorry I fell asleep topless. - "It's okay," they s... continue reading

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So a few years ago, my best friend asked me to be a surrogate mother for her and her husband since she was unable to have a child. This involved me having sex with her husband for a couple of months before he got me pregnant. (We kept fucking after I got pregnant as well but mostly cause we liked it so much)

When I gave birth to a girl, I took care of the baby for a while whilst my friend induced lactation and could take over completely.

Fast forward to this Christmas and they asked me once again to be a surrogate. As you can read in the title, I am quite old so at first I wasn't interested but she is my best friend so I did consider it. By February, I was bouncing like a mad woman on her husband's hard cock. We fucked pretty much every day. He would often pick me up at work to bring me home and fuck me. Sometimes we didn't make it all the way and fucked in the car. Other times, we didn't even make it to the car and fucked on my desk.

I took multiple pregnancy tests and finally g... continue reading

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**Part 7- Endless Summer**

After the disappointing sex she had with my virgin friend, I decided that stepmother had waited long enough. She had been obedient after all and to be honest I was dying to get inside her pussy again. I had toyed with her emotions, played my game with her, and now it was time to have some fun.

We were going to be alone at the house all that week, my siblings at day camp and father away at work. This was going to be the perfect time.

I found her in the morning after she returned from dropping brother and sister off at camp that Tuesday. We met each other in the hallway and stopped, she leaned against the wall waiting for me to instruct her.

I made a suggestion.

“Hey lets hang out by the pool today. Get some sun, go swimming, what do you say?”

“Sure, that sounds like fun.”

She answered and turned to walk off toward the bedroom.

“Wear something sexy.”

I gave her a pop on her ass as she walked away.

She continued without acknowledgin... continue reading

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Part 5 - Homecoming

That last night away at college was wild. We threw a rager that went on all night. One last party before the summer. A lot of fun, tons of drinking, but boy I felt it the next morning. I was dreading having to pack up my shit and load into my car. I slept most of the day trying to recover.

I finally got around to packing up in the late afternoon. I was starving and got a bite on my way out of town, and headed back home. I was driving back to spend the summer at the house shared by my father, and stepmother. Back to the home I grew up in.

On my drive back I thought of all the fun we could have this summer. What new games we could play, she and I? How far was she willing to let things go? One thing was sure. I was gonna to find out.

I got in fairly late. Around midnight. The house was dark and quiet. I was careful not to make too much noise as I went upstairs. Still half recovering from the night before, I needed a good night slee... continue reading

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**Part 2 - A Bold Move**

So before we get back to the story, I want to tell you a little bit about my stepmom.

She is a total smoke show. My father married her about a year after he and my mother divorced. My mom was so fucking pissed... and jealous.

Mother went on and on about how he had married a younger woman, she was over ten years younger than my dad. My mom never forgot it, and I always got to hear her views on the subject. Sour grapes I guess.

When he married her she was like a trophy wife. Young, beautiful, light brunette hair, long and wavy. A real beauty. Pretty blue eyes. Like a beauty queen. Every man’s fantasy.

She and I were never close although I always thought she was sexy. Even from a young age. I was enamored by her. I think I got my first little boner looking and thinking of her as a kid. She never treated me bad, but she never treated me like a son either. She was more interested in starting a new family with my father. I was an af... continue reading

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Hi! I’m Evie! A small disclaimer: I am actually 43 currently, but wanted to use the age I was when this happened.

It all started at a holiday party my best friend, Olivia, was having at her place a couple years ago. Olivia and I went to college together, were roommates for the first couple years before I got married, and have been in the same city our entire adult lives. We are two peas in a pod! Her home is quite lovely, and large enough to host fairly large get-togethers. This one is no exception with a catered dinner, open bar, and plenty of room to mingle and talk amongst the small sea of people.

We also had kids around the same time - two for her and three for me - so they’re there too, all home from university for a few weeks before spring semester starts. Her youngest son is a track star at a college close by while her oldest, Kevin, has always been stupidly smart. Graduated high school early, already has a bachelor’s degree, and will have a master’s degree after the next se... continue reading

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I drop my kids off at elementary school.. lots of parents in the area walk there and you sort of see the same characters every day. Several smokeshows wearing yoga pants/ pajamas.. it's a milf paradise..

One mom early 20s bikes her kid in the back saddle.. by chance, one of the attachments fell off and i was there to help her fix it.

we started chatting and there was this immediate sexual tension.. shes got a banging latina body where you can sense she took an extra minute on her outfit to look right before heading out.

A few weeks pass and we casualy exchange greetings.. one day.. it started raining bad and i could see her from my car she was waiting under a an awning.. told her to hop in.

In the car sort of drying her self off.. she tells me her husband already went to work and offered me to come in real quick for coffee. seems completely innocent.

walking in.. she starts telling me how she's having problems with her marriage and so tired of her guy.. they "haven't been intimate... continue reading

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I was 19 at the time. Still in college, horny af like every late teens guy and perusing through OkCupid (actually a good dating site at the time)

I came across this 43 year old milf and we hit it off. After a couple days of texting, I coerced her into inviting me over.

She was a 5’2 thick brunette with some great titties that some of the best shaped nipples and areolas I’ve ever sucked on.

When she opened the door she hugged me and told me to be quiet and follow her. She led me up a staircase that led to a small hallway and had doors. Two on the left, one on the right, and one straight back.

As we walked past the door on the right, I heard a young man’s voice coming from the other side.

She took me to the one straight back and said she’d be right back. I heard one of the doors in the hallway open and she started talking to someone.

She came back and said “Thats my son, he’s 24” She must’ve noticed the slightly concerned look on my face

“Dont worry, he’s busy playing video games... continue reading

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About six months ago we had our twin daughters and sex has kind of been on the back burner, but last Valentines Day i gave my husband a sex coupon book that included a few coupons for his favorite things and a few for things that were kinkier than normal for us.

Today, my amazing MIL offered to watch the girls for the night so we could go enjoy the new Dr. Strange movie like real grown ups. After dropping off the girls we come home to get ready for our date afternoon when hubs tells me “Wear something easy access” and hands me a coupon for 1 full day of free use. We’ve never done free use before, but the idea was definitely exciting.

But before I had a chance to leave the bedroom I was bent over our bed and told not to cum. He pounded into me until I was panting and begging but he wouldn’t let me cum. It was a quick 10 minute fuck but it felt agonizingly long waiting for him to fill me full of his cum.

We made it out the door and all the way to the movie theater before he did a... continue reading

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a year ago inmilfbyAnonymous

Mom of my ex gf

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This happened years ago when I was still with my gf. Before I dive into the story I should tell some background information first.

My ex and her mom lived together and were very open with everything to the point where they shower where they both walk in on each other, my ex shared what toys she got and discussed our sex live with her mom even every once in a while where we had sex and she was talking to her mom about anything.

Now you know that this story was when my ex and I were together for about 6 months, but she began to have less interest in sex so when I took a shower there due the lack of sex I needed some relieve and took the matter in my own hand when her mom walked in on me.

Of course I immediately stopped, but she said: “you don’t have to stop, it’s completely normal to do plus I know you and my daughter have less sex, if you want I could give you a hand? I mean it’s better than your own hand right?”. Me not knowing what to say friendly declined since I am still with my... continue reading

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I'm a single, divorced mother who has an 18 year old son, his best friend Tyler (not his real name) is 19 and quite a handsome young man. Now this goes back about a week. Tyler came over to visit my son and hang out for the day and I was in kitchen getting lunch ready. Tyler came down stairs to get a drink and we had short chat. During the chat I could swear he was checking me out by looking at me up and down but at the time I didn't think anything of it so I put it out of my mind.

2 days go by and Tyler stops by again but doesn't stay long as he and my son went were heading out for the day. We were in the front room as I was cleaning it and he was sitting on the couch waiting for my son. Now I must admit what I did next was on purpose as I wanted to see if I was right or not about the other day. I went to the coffee table and started to clean it. I had bent down in front of Tyler in a way so he could see down my top, and lo and behold he was staring right down it. When I rose up he ... continue reading

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a year ago inmilfbyAnonymous

Caught by my friends MILF

To preference this story, inknow it sounds like something straight out of a porno but it did in fact happen to me. I have a few other adventures that I will share in time.

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It was summer and I had been out drinking with a few friends during the day, I had not drink as much as the others because I had to work the next day but was still a good few drinks deep. A couple of us ended up going back to one of our friends houses because it was close to the last bar (also because his mom was an absolute MILF). We arrived around 5PM so it was still warm, my friends mom (Victoria) was out by the pool so we decided to join her for a couple more drinks.

Everyone else grabbed the available sun loungers and seats around her after they had grabbed drinks from the fridge but I held back and asked her if I could get a drink. She smiled and said she would take a beer, so I grabbed 2 beers from the fridge and handed one to Victoria.

Now when I say Victoria w... continue reading

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a year ago inmilfbyAnonymous

I was seduced babysitting

[MF] I was seduced after babysitting

When I [m] was in my teens, I used to babysit for a friend of the family. She was a single mother in her early thirties. She was average looking, nothing special, but still had a great body despite having a child.

She usually went out a couple Friday's or Saturday's each month and paid really well. Often times she would call and ask if I was ok spending the night because she was too 'drunk' to come home. Yea, I knew she was hooking up and spending the night at their place, but I didn't care because on those night I usually made a few hundred dollars. Like I said, she paid really well.

One night she got back at her usual time, slightly after bar close. She wore a little black dress that left little to the imagination. You could tell she intended to get laid that night, but came home empty handed instead.

We were talking and I was giving my report as to how the night went, no sexual talk, just a parent talking to the babysitter. I was getting rea... continue reading

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n the earlier days of me exploring my darker side, I started with dogging. At first being watched by a group of doggers playing with myself or sucking Hubbys cock with the light on in the car.

There would be a few doggers with cock in hands and it wasn’t long before I was winding the window down and sucking cocks- what a thrill, the taste of strangers’ cocks, all stiff for me. My head half out the window with my hand and lips around their cocks. My pussy was sopping wet as I drained one cock after another. I swallowed unless they wanted to cum on my face, and later over my ass and wet cunt, with a rough fingering. I like the closer physical interaction.

It progressed to me sitting in the back of our hatch back, sucking cock, with my legs open allowing my cunt to be fingered, my tits squeezed, my nipples linked and pinched. It was all horny yet polite, if you know what I mean. It was always sexy with a laugh.

At some point it progressed to me getting a good fucking. A fifty somethi... continue reading

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My ex husband and I had been married 21 years and been together for 25. We have two kids together both 18 and 20. He cheated on me with an 18yo girl for a few months before I found out, the divorce was rough for me and I felt like shit since he was the love of my life.

A few days before Thanksgiving I decided to go to a bar for a drink, I sat down and ordered a Tequila. After a few minutes a man sat beside and told me how beautiful I look. Normally this wouldn’t work on me but my heartache left somewhat needing affection. We chatted for a bit, I didn’t expect much, but he was actually incredibly smart and funny. Since he was in town on business, I knew I’d never see him again and there was something inside me telling me to sleep with him. The chatting turned into flirting and then us kissing.

Eventually we went back to his hotel room and it didn’t take long for our clothes to come off. it turns out his dick was enormous, like way bigger than my ex. He had me on the edge of the bed ... continue reading

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a year ago inmilfbyAnonymous

High School Teacher

One Saturday night when I was in college I decided to goto the local club and have some fun. Maybe an hour after I got there I saw my old high school teacher walk in with her friends. She was wearing a black dress with black heels and had her hair and makeup at done, she looked amazing. I kept doing my thing, but then I saw at the bar getting a drink so I went over and started chatting with her and she was telling how the club scene it’s for her anymore but her friend really wanted to go. I asked her if she wanted to dance and she said yes, we finished our drinks and started dancing. It started off normal but as time went on it became more sexual. We stopped dancing and I asked her if she wanted to come back to my place as I lived closed by. She agreed which was a surprise to me and she went to tell her friends she was leaving and met me outside. We walked back to me place and as soon as the door closed we started making out and feeling each other up. She was stroking my cock thou... continue reading

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I’m a freshman in college and I go to a college that was local to were I was from.

I was on tinder swiping left . (Most weren’t my type so yeah) yesterday and I saw my old teacher and her bio said:

29 years old and wanting to rock a young person day. Jk. Unless😏

I said to myself “she has a husband, why is she on tinder” so I swiped right. And waited until she matched with me. And she around 5 last night to swiped right and said:

“Ian is that you?”

I said yes and we talked about life and I asked about her husband. And I found out that she got a divorced. And she joined tinder to live out the years she missed. So i said I could help her with that and we gave each other numbers and made plans to have dinner tonight.

I’ll give a update later

... continue reading

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So about 4 years ago I’d just broke up with my ex gf as she was going to uni (I’m from England). I decided I would go with her and her mam to drop her off at uni as like a final goodbye kind of thing. Anyways we had dropped her off and spent a couple of hours looking around after dropping her off. Her mam decided we’d go back the long way home to pass some time and I was fairly close with her so she was kind of sad it was probably going to be the last time we seen each other.

We stopped for a coffee and toilet break at a service station. We hopped back in the car and I told her I was feeling rather sad it was all coming to an end, she rubbed my lap and told me we’ll stay in contact regardless. Her small hands rubbing my lap were making me hard in my pants, my jeans were bulging like mad! I think she noticed but never said anything and just kept on driving. 3 hours into the 5 hour drive home she pulled over to stretch her legs and I noticed she was sorting her top out or rearranging h... continue reading

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After my break-up with Eliza, I was upset. I stopped going out for a couple weeks (except for my job). After that, I realized I needed to move on. I began to wake up at 7am and do some running at a park a few blocks from were I live. During my warm-up, I noticed a woman in her late 40's that was behind me. She was excercising, and she was very sexy. Petite and with a curvy figure. She had small breasts and wore yoga pants that were filled by her large hips and a big bubble butt. After weeks of just jacking off at home, I noticed that I didn't have sex in a while. Eliza and I were very sexually active, specially because we were living together. I got used to having sex almost daily because my girl had the same drive, and now I was single. I had not much to lose and a lot to look forward to.

\-Hey- I greeted her- Do you do this often? I'm new and don't know much about warming up for running.

\-Hi- she smiled-. Yeah, sure. Just follow me, I have been doing this for a long time. ... continue reading

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