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My First MILF

Another great story from a loyal reader. Enjoy! It was what I would call the greatest spring of my life. I had my drivers license. I had a cool car. I had a great job at the country club. And I had two hot girls that I was fucking on a regular basis, sometimes both in the same day. I thought I was a Casanova and knew everything. There was this couple that I would do stuff with and caddy for, Daisy and Walt. Daisy was a sweet heart and fun to talk to and very classy, Walt was rich drunk and...

mall milf

As we all know the malls are failing, so I thought why not go to the local mall and see how bad it is, it was just before the stores open up when I got there about 10 am, walked inside to the main concourse was walking along taking notice of the stores that had closed up there was a couple of anchor stores left and one was about to close it's doors.I walked the whole 1 mile length and started down the side isle checking out the shops I turned back towards the main concourse and saw this nice...

My Teacher the MILF

My senior year in High School was anything but uneventful. My schedule wasn't very tough as I only had 3 classes. In my last class of the day I was a "Teachers Assistant" for a math class. The teacher Mrs. Brown was an attractive lady in her mid 40s. To say she was a MILF would be an understatement. She had told me that she put all her tests on a flash drive so that she could just keep them handy whenever she needed to have them printed I could print them off the computer. Sometimes she would...

Black Step Milf

Step MilfI've been living with my step mother for about two years now. We've lived in the same house together ever since my dad pasted away. This is the story of the first day that I hooked up with her....First off let me paint you a picture. My step mother is about 5'6, black, with dark hair, double D's, a big chunky ass, thick thighs, big luscious lips, a pretty thin waist (she has a little belly on her but she is far from fat), and a very pretty face. People say that she kind of looks like...

Redhead Cum Slut MILF

Megan Fox drove down the country road just outside of Hardintown and she felt her body become more aroused as she anticipated what was about to happen. Megan also had a small twinge of guilt as she focused on finding the right country rode turnoff.She was excited by the thought of removing the costume of her being a straight laced mom and wife but she also felt guilty about the lie she lived with that same family. Then the reality hit her again: "I'm a slut! An extremely perverted slut!"It had...

My First MILF

My First MILFPart 1When you grew up in a conservative small rural community in the mid-west back in the 1960s, it was not unusual to reach high school graduation without being initiated into the practical realities of sex. None of my friends had had sex. Petting or copping a feel was a big deal. One of my friends claimed to have felt his girlfriend's tits a few times, but I was more than a little suspicious about that. One of the girls in my class was rumored to have been "ruined" by a...

I lost my virginity to a teenage Milf

When I was in high school there was this girl who I met in my sophomore year, we talked a bit and we became friends. Everyday I sat by her in lunch and I actually liked her, but I found out later she had a boyfriend and she was later pregnant with his k**. I didn't see her that much in Junior or Senior Year, but I still said "Hi" to her once and awhile but we kinda lost contact with each other for awhile. I saw her at graduation with her sexy black dress she had, I talked to her and asked her...

Rough blowhob with black milf

So it was about 11 o'clock at night I was sat down my local industrial estate in my car, smoking a joint. Somewhere it was quiet were I could relax. When I heard someone approaching my car I could hear it was a woman straight away from the sound of her heels. She tapped on my window and asked me what I was doing? She then asked me if I had any money for a taxi home as it was a 3 mile walk. I told her that I didn't have any cash on me, she looked at me and said well can you give me a lift i can...

The Lifeguard and the MILF

For four years of my life I was a lifeguard on a popular beach in New Jersey. At eighteen years old, I had experienced quite a few girls, had done what I thought was a lot of stuff and I was feeling very sexually accomplished. A few weeks into the summer, a family started coming to the beach daily and setting up near my stand. They had two small kids that would play at the water's edge all day, giving me occasional glimpses of a hot mom bending over, kneeling, etc.One day, she caught me...

MILF

Cheating slutty milf

This story is about how I seduced a 39 year old married milf off a dating website. This is a genuine story and I will be recording and taking pictures the next time we meet up. This happened last year so I was 23 and she was 39. I had a girlfriend and the time but I wanted Kate's pussy too bad to miss out. Kate is 39 , married and has 4 k**s, she lives relatively local to me so it was quite easy to meet up.We got talking over a course of a few weeks , exchanged numbers and started to flirt more...

hand drawn comic Fucked by a Black MILF

true story about a lady in my neighborhood , I had an encounter with a few wks ago: I illustrated it into a comic.Okay, so there’s this library by my house that I have to walk to, to use internet and emails and stuff. I go there pretty much every day. And actually I used to always fantasize, that I’d meet some horny MILF or horny single lady, along the way, who just stays in her apartment all day and wants a lover to help her get off. This never happened so I kinda just gave up on it and lost...

The Morning Milf

This is a story of fiction, although I wish it were non-fiction. First Timer-be gentle.There she was, where she usually is on Monday morning, right out front of the school. I'd see her almost every day if I were lucky enough to catch her. I would offer to drop off my nephews at school just to catch a glimpse of her when she dropped her boys off. I'd watch her Corolla pull up to the curb, from a distance to avoid being too obvious. It was truly a sight to see. She was an older woman, but a sexy...

MILF

Cumming in Brad s MILF

Brad was a good friend of mine, we had been friends for about five years or so. I often just slept at his place after we went out partying or anything like that. She had been divorced for about two years and had really gotten into shape after the divorce was final. One night, Brad and I came home after midnight and Brad passed out drunk onto the couch. So I quietly went upstairs to go into his room to sleep. I saw Brad's mom, Sara, was still awake, the light in her room still on. I opened the...

MILF

First time with white milf

I had just graduated from high school a cople weeks before my aunts 30th biryhday, my aunt was turning 30 I believe an of course I went to the party. Me an my aunt was pretty close not best friends but not distant ones either. So the party ended up taking place at my aunts friends jazz house she was like my unofficial stepmom I call her that because her an my dad dated awhile an she was nice. Anyway I arrive at the party an not too long after I notice my stepmoms friend whom she invited because...

The Pregnant Neighborhood MILF

My name is Sandra, and my husband Ed and I are thirty-four years old and live in a nice suburb of Houston with our one-year old daughter. Ed is gainfully employed in the banking industry, and although I also had a good job as a systems analyst, I was able to quit when our daughter was born.We met in our senior year in college and have had a picture-perfect marriage for the past eleven years, at least until seven months ago when I got pregnant with our second child. That second pregnancy, coming...

MILF

My First and only Milf

The following is a true story. I have been carrying it around in my mind for years. Married now with a family, it is something I have shared with nobody and it just feels good to get off my chest.Admittedly I was naive. A small town boy at a major midwestern university living on my own. Being a mechanical engineer is all I had wanted to be. I wasn't a genius by any stretch of the imagination, thus school didn't come easy for me. Studying and going to class was all I cared about. But then...

Sexy Ali the northern MILF

Just wanted to share possibly my greatest sexual experience from when I was young with you all. When I was only 19 I got to know this uber sexy older woman; blonde, petit and busty. She was like Debbie Harry in her prime. She was 36 and was old enough to be my mother, she was confident, slim and busty and in her sexual prime and oozed it from every orifice. She epitomised the term MILF. I got to know her through a friend who worked with her, and before I knew it we were flirting over the...

Santa the Elf and the MILF

Last year I performed as Santa Claus at two Mexican super markets. I enjoyed hearing the children’s wishes for Christmas and spreading a little joy. At this one appearance I was joined by an elf. I had to drive to the elf’s home and pick her up. She was 19 years old and did not drive. To give her an added level of protection her older companion joined us. The older companion’s name was Amy and the elf was Lisa. We had two stops to make. Both were markets in a small chain of family owned stores....

First Time

Ooty Trip And A Milf

Hello. Rahul here. I am going to tell you about a story which happened when I was vacationing in Ooty. I and my girlfriend planned for the trip. Somehow I had to go alone in the end. She had some last minute business trip and had to cancel. Since I had booked the resort and I thought of going and spending some alone time there. I reached the resort and I was relaxing for a bit over there. The first day I checked out some famous places nearby alone. After my short trip in the evening. I was...

Shreya Aunty 8211 Part 2 Fucked The Sexy Milf

Hello ISS readers.Welcome to the story. This is the continuation of a story named Shreya aunty – Part 1.Read and enjoy. I was surprised and I still said that I will sleep in the hall itself. She insisted and took my pillow and kept on the bed. I was happy but somewhere inside I was afraid too. She slept beside me turning away from me and I can see her lower back between her shirt and track pants. Her butt cheeks tempted me through that track pant. I waited for a long time to make sure that she...

My First Time With A MILF

We were in our last year of school and my friends and I had this band. It was me, Jerry, Pete, and Bart and we were pretty good. We played country and folk music. We were invited to play at this benefit folk concert in a nearby town for a weekend. They were going to put us up in a hotel and feed us. We were pretty pumped about the whole deal. We got there on Friday afternoon and found our spot on the lineup. We were playing right after these older ladies who did some fiddle stuff. They were...

Sex With A Sexy Big Ass Bangalore Milf

Hello Dear readers. This is CrazyRocky again with a new story. Enjoy the story guys. This incident happened in Bangalore. Although I am from Delhi but currently living in Bangalore. So any horny ladies aunties and lonely women particularly from Bangalore, in need of some adventure do mail me- . This amazing incident happened a few weeks ago in Bangalore. I have a habit of working out and going to the gym and swimming. As a daily routine, I go to the gym for a workout but my time is not fixed....

What a Hot MILF

Ive always loved sex I cant get enough sex, I fix cars in my spare time i have quite alot of female customers, but there is one that ive been interested in for quite sometime. i normally pick her car up fix it and take it back to her and she brings me home. I have always flirted with her but nothing ever happened till one night i was drunk and i started to text her. shes with someoneand she has k**s.Anyway she was very flirty in her replies so i said the next time your car needs fixed im going...

Part 24 Sex With Neighbour MILF

After Vani, I had given up having sexual intercourses with other females. I had restricted myself to only my wife and occasionally with my wife’s permission, some kind of non-vaginal penetrative intercourse with Vani. It therefore came as a complete surprise to me that I was seduced by one of my neighbours in Mumbai and I fell flat for her. Pranitha is her name and she is basically a Mangalorean. She is now 57 and a voluptuous woman. A housewife, whose husband works in Pune and visits her once...

Young IT Guy Fucked Bangalore MILF

Hi..To brief about myself..Me Ranadip, a matured Bengali IT guy staying at Bangalore..My age is 29, height 5’9″..Waiting to hear from you at Coming to the story, there lived a single mom Kavita in the same building as of ours. Aged about 38, he was really a Bengali bombshell with a figure to die for 38-30-36. She was a bit plumpy being the mom of 2 children and I always had my eyes on her curves. Once I returned late night after a party with friends and found she was also waiting for the lift...

Gratification Of A Milf

Hi. I’m Aniket. I am living in Delhi and presently working as a consultant. The sex story happened 5 years ago when I was new to this city and had just enrolled in Delhi University. I was not doing well in my studies back then and was very miserable at that time. Being an outstanding academic all through my life, this average performance took a toll on me. It was during those frustrating day that a beautiful milf Shruti came to my life. And it was so sudden and wonderful that even now I wonder...

Indian Milf

This is the story of when i got with a milfIt was the day before the wedding of my mate Jay. I was at his house for the pre-wedding ceremonies. Wasn't the most exciting thing in the world, however i thought id waste time chatting up random girls, thought id might as well shag a few while i had a chance. Anyways i ended up talking to one woman, Alpa. she was tall, thin but a lil curvy with nice 36d looking tits. she was also 42 years old i Started talking to her and she told me she had 2 k**s,...

I met a MILF

Fucking a woman who is much older than you can be very exciting, this guy tried the hot MILF’s pussy and he really loved it…I had been attracted to her since I saw her for the first time: she was walking down the 9th street by my side: she was 32 and I was 18 at the time. So I didn’t even hope to have a slightest chance to make it out with such a gorgeous milf! At that moment I thought she was the sexiest and horniest mature lady all over the planet, and that the cock fucking her was the...

The Hooker and The Milf

So usual boring ass sunday night at work polishing glasses, smoking the occasional cigarette and serving the odd customer a simple drink....same shit different day...9 pm and i am dreading the next 5 hours of doing fuck all and waiting to go home plus....a bit of a hangover from saturday night shenanigans is not helping my cause....The minutes slowly tick by and usually when i am hungover i feel the need to a cuddle and sex more so than when i am sober....so as i am clock watching i am...

Slave To A Lonely Milf

Hello everyone ! Well for a start, this is the very first story I’m posting here which is about how I met a real milf ( in her 40’s ) online, which finally led to fulfilling her fantasies of domination. For an introduction, I’m an entrepreneur by profession and a pretty successful one ( I guess, have closed VC rounds lol ) but yes as every individual has their own personal life away from the professional, so do I. I love getting dominated by women and being their slave. I like to be a dirty...

My Debut T20 With Milf

It happened six years ago but I remember the sex very well as if it happened yesterday because it was the first time I had sex. I just joined in it company after graduation and got myself a pretty girl. She stayed in an apartment with her friend. Since I drop my girl in her flat after office, I have to visit her apartment very often but nothing happened ever between us because I thought my girlfriend is more orthodox kind of girl and then she won’t allow me to fuck her before marriage. Whenever...

My first milf

Introduction: This milf was full of surprises Every word of the following story is true, the woman I shared this experience with was absolutely wonderful, both in and outside the bedroom, and still is to this day.I'm Stan, 22 and a white college student 6'2 155lbs, short brown hair, pretty tan, and athletic. She's Lori, 45, around 5'8 a bit on the chubby side but hwp, black, a beatuiful round ass, gorgous smile, and what I would later find out to be 36DDs. her personality is what always caught...

Giglo Service To A Milf

Hi dosto main sachin ek bar fir se apni nayi story le kar hazir hu. Meri pichli story iss reader ki chudayi ko apne bhut pyar diya main uske liye ap sab ka dhanyawad karna chahta hu. Jo log mujhe nhi janta plz meri purani kahaniya pade. Aur main sachin hu punjab ka rehne wala hu aur gurgaon main job karta hu aur part time ek therapist bhi hu Aur agar meri yeh story pasand aye plz mail me at aur agar kisi ko bhi meri service chahiye jarur btaye mujhe travel main koi problem nhi hai aur main...

Mom the MILF

Daddy tells mom that the pool guys should be here sometime today, to fix the pump. Mom said that will be good, so we can have that pool party we have every year. Daddy slapped mom on the ass as he gave her a kiss before going to work.I came up stairs with just a tshirt and my thong undies on, mom told me I needed to get dressed cuza the pool guys were coming over. I told her that I was just getting a drink, then in the shower for work.Mom came downstairs to put a load of wash in and seen me...

Online Sexting To Bedroom With Milf

Hi everyone, I am Robin Dcosta and I am gonna tell you a true story which happened to me just a few months back.It involves how I had a fun sex chat with a milf and later fucked the living daylights out of her. I am a good looking 26 years old with a good job and nice bank balance. I am 6 feet and weigh 68 kgs with a ripped body. My cock is 7 inches long and 3.5 inches in width. Mature ladies and aunties looking for a good time can contact me on or kik – cuteguy0103. Full privacy guaranteed. I...

Mistaken As Playboy Leads To Fuck A Mature Lady Milf

Hi guys, how are you all… This is Sachjo from Gandhinagar.This is my third sex story. I am writing my real story, this incident happened in October first week.I am a software developer in an MNC age 23 living in Gandhinagar.The story is between me and a mature lady who thought I am gigolo. She is from Ahmadabad and from a decent family. Mai 2nd ocotber ko ahmedabad gaya hua tha shaam ka time tha mere freind ke yaha se jab wapas nikla to 9 baj chuke the aur higway pr tha meri cab ka wait kr rha...

Cheating With 56 Years Old Milf

Hello everyone !! It’s Mayank , 26 years old married guy from Gurgaon .This sex story is about my extra-marital affair.Before my marriage I was on many dating sites and used to chat and meet many ladies !! Now after an year in marriage with all excitement gone.One day sitting in office I opened my all old accounts.Most of which were fake and started chatting again.But this time cos I was married and could just do it in free time at office I was not succeeding in meeting anyone. Then one day...

My First Time With A MILF

We were in our last year of school and my friends and I had this band. It was me, Jerry, Pete, and Bart and we were pretty good. We played country and folk music. We were invited to play at this benefit folk concert in a nearby town for a weekend. They were going to put us up in a hotel and feed us. We were pretty pumped about the whole deal. We got there on Friday afternoon and found our spot on the lineup. We were playing right after these older ladies who did some fiddle stuff. They were...

Night At The Hotel 8211 Britain MILF

Hey all! Devil here with a New Trilogy. In this one all the events take place at the same place with different people. All the characters of the Story and the Story itself is completely imaginary. Please mail me all your comments, suggestions and feedbacks Coming to the Story… This is Susheel’s Story. A 30 Year old Businessman who has come to Mussoorie on a Business Trip and meets this Older Lady at the Dinner. Read on to find out how events turn up leading to intimacy between them.. In...

My First MILF

I was in my mid twenties. Just having moved several states away I was in a pretty long and unbearable dry spell. I hadn't gotten laid in months. I just wanted to fuck. So I headed out to a bar that I had heard was good for hook ups. I got there and saw that the pickings where pretty slim. Any girls that looked to be about my age were already paired with a guy. But there was one hot woman by herself at the bar. I walked over and we chatted a bit. Her name was Lisa. I found out that her and her...

MILF

[/image]hi my name is sarah im a 41 yr old milf or so im told.. i have 2 sexy 2osomething daughters..my eldest Carmin is staying with us until her and her boyfriend get a flat..last saturday afternoon.. i thought the house was empty.. so i decieded to have a shower..i shaved my pussy.. as i do...i then heard moaning from carmins room i slowly opened the door..carmins boyfriend Steven was naked with his cock up my daughter.. and here was i naked watching.. i felt horny watching his big cock...

Door to Door Cable TV Sales Milf

Waking up kind of late this Saturday morning, I was leisurly going through my morning routine of coffee and cigarette. I was glad to have the house to myself and I sat quietly sipping my hot beverage. I heard a car door out front and I partially stood up to get a view through the picture window of the street a few feet away. I see somene getting out of a older model mini van, and my first thought, no lie is I wonder if its a sexy woman. Moments later as they come around the ront of...

Me Fucking a Milf

This Milf is all alone and she can’t get the young neighbor out of her sluttish mind, she decides to turn to him under the pretence of fixing her laptop, but things get so wild…Request for assistanceVivienne liked her neighbor’s son. He was 18 and so sweet, so cute. She wanted to try him.John was sitting at his computer reading porn stories and thinking of some older woman to fuck. He had a huge erection and was masturbating while reading.Vivienne knew John’s mother went to work, the night...

Sexual Encounter With Hot MILF

Hi Am Munir.I am a regular visitor of the ISS site. I go through all stories published here. Some of the stories are really entertaining and some of the stories are really fake. It could be understood the way the stories are narrated which one is real and which one is fake. Anyways I have been mulling over writing a story for ISS since a couple f days after reading the experiences of so many people on ISS site and inspired to write my story. The story may be a little lengthy and some readers...

Incest

The Milf

My little sisters best friend came to me one day in the summer. The weather was hot and so was she in her own way but I knew for now she was off the market. She wanted me to help her mum as their pc had broken down. Her mother was a single parent and must have been a young mum in her day as she was still only about 36. Being the man that I am I accepted nad went round to help her mother with the pc, not expecting anything out of the ordinary to take place.I knocked on the door and there was no...

Party MILF

Hubby was working away from home (as usual) so I'd arranged to go out with a friend for a few drinks and a meal.She had invited me to stay over as she stays a good distance from me. I told my s*******n year old son that I wouldn't be home.After the meal we decided to go to a club. Club was really lively but after a couple of drinks my friend began to feel unwell. We got a taxi and dropped her at her flat. After seeing she was OK and in bed I decided to take a taxi home.The house was rocking...

My best friend s mother is a MILF

My name is Eric, I'm 19 years old. My best friend Dan is 19 years old too. We have been best friends since we were four years old. My mother and Dan's mother, Cheryl, are very good friends too. Cheryl is an attractive 40 year old women, she has blond hair and a great slim body. Dan and his mother always have had a real good connection, so sometimes she hangs out with us. Dan and I always have sleep overs. We had one last month at Dan's house. When I stayed there it was a hot summer day. It's...

MILF

Meeting the milf

We'd only ever talked on the Internet and now I find myself sat outside her house, walking up the path wondering what I might find on the other side. Knock on the door, she answers 5'4 short blond hair, black silk dressing gown on. She invites me in. We sit chatting on the sofa, my mind is racing, all I can think about is weather she has got that new underwear on under that gown she was telling me about? And are they stockings I can see? We chat for hours. Then she gets up and locks the back...

MILF

Incubus Succubus MILF

Incubus: Hot Succubus Mama By Bud A sequel to the Incubus storyline I wrote. This includes anal birth as a fun impossible concept, much like a lot of the story so far. -*- At the end of a grueling year of learning all sorts of ways to service her master, Cum Slut was now fully submissive to him. Though in the back of her mind, when the year was fully up she was in control again. She would mourn her lost love and part with Gomorrah, who had harmed her by taking her love from her....

My Fantasy I wish I d meet this MILF

My fantasy: I wish I knew this MILF telling a story like this. She claims a woman is never too old for sex. Here is the story she wrote."I’m about to turn to 60, yet it looks like if my hormones have shoot forth again making me gush with enthusiasm, love and affection. Despite I’m a widow I still attract males who constantly would court me. I like to read erotic stories as well as seeing pics and videos at your site. Yesterday was Saturday, and I still have memores of my first rendezvous with a...

Mature

Got MILF

Well I guess I should start off by describing myself... I'm 5'8, slender, long legs, long blond hair, and nice little B-cups. It was a Friday night and I was ready to party. My friend Jaclyn called me up and asked me if I wanted to sleepover that night, and of course I said yes! At about 7:00 I arrived at her house wearing a tank top and denim mini skirt. We ordered pizza and watched a movie and at about 8:30 her mom, Alicia, came home from work. Alicia has always been attractive to me...

MILF

Next door milf

I'm going to start with an older one from my teen years and my next door milf neighbour. I was 18 and she was 36 with 2 k**s who I baby sat for sometimes. Albeit searching there house for porn and finding Polaroids of Sarah which i happily kept for wanking material. Sarah had split from her husband, she had known me since I was 11 and she had great tits and I wanked over her many many times. I was 18 with a stunning girlfriend and on this occasion we were at my house and Sarah had been up...

50th Birthday surprise for Miss Milf

50th Birthday surprise for Miss MilfIt was my birthday, so I’d taken the day off work to do some retail therapy followed by a few glasses of wine with the girls from work at lunchtime. I got a cab into town and headed for the shops, the sales were still on so I was looking forward to getting some nice bits. I was picking up dresses and tops without realising the time, I had to rush to the till to pay without trying them on or I’d be late at the wine bar, as I was about to pay, I spotted a...

Lupe The Colombian Guesthouse MILF

I want to tell the tale of how I got involved in the amazing sexual exploits of Lupe, my uncle’s second wife, when I stayed at their guesthouse, on the Pacific coast of Colombia, in South America. But I must give you some background first.I had graduated from university here in London and had then taken a year out travelling around the world. On my travels across Europe and Asia, I had pursued my passion for photographing the natural world. I had set up a website and posted updates almost every...

MILF

Missy The MILF

I envied Jimmy, since his mom is the coolest. She’d let us get away with almost anything when, we were kids. Her name is Missy, I always called her Mrs. T. She was short, pretty, and a little curvy. She had shoulder-length blonde hair, and wore these red rimmed glasses. She looked a lot younger than the late forties she is.It seemed like Mrs. T worked all the time. But Jimmy and I never used that as an excuse to do whatever we wanted, whenever we wanted. She always seemed to know what we were...

MILF

Jaq the milf

It was a Sunday afternoon back in 2009. Jaq realised that she had the attention of our son's friend.The afternoon was very warm, friends and family had arrived for an afternoon barbeque and drinks. The last guest to arrive was Mark. Mark was the friend of our son, Max. The drinks were flowing and everyone was having a great time, including Mark. Every time I looked for Jaq, Mark appeared to be nearby.Later in the afternoon Jaq and myself were in the kitchen opening some more wine. I mentioned...

MILF

Bumble Dating App Got Me A MILF

Hey! This is my first ever ISS story and it’s about from a dating app. I am a 19 year 5ft 7 inches guy with a sculpted build based in Delhi. I am going to talk about my recent experience with you all. I downloaded Bumble (a dating app) to see what’s it about. I was bored by the cringe or uninteresting Bios of 18-19-year-old girls. So I switched to 40+ yr old. To my surprise, there were 10-15 women, and 8-9 were pretty cute. I swiped right on them as they were ‘verified.’ I had stopped opening...

Edging Sex With A Milf

This story of edging sex is a much shorter version of what I generally post. After a lot of feedback, I wanted to share something about what happened with no previous context. I hope you enjoy it. This happened about a year and a half ago or so, just before the pandemic hit the city of London. I am working in a corporate IT job with really flexible hours. I met a woman on the Ashley Madison app who surprisingly was not fake. We started the initial chat and quickly caught on. We were desperate...

Small Town Guy Big City MILF

Hey everyone, this is Anonymous writer. I’m writing my first story here, and it’s a real one. It happened when I was 19. I’m from Jamshedpur, Jharkhand, a small yet developed city to some extent. I’m a sportsman playing all sports. I’m a national player, and I’m quite athletic. I’m 6 ft, a bit on the darker side and always have been popular in my school and the state. Yeah, I had a couple of girls in my life. But I was in a serious relationship for 2 years. I and my gf had so much fun! We had a...

The Office MILF

When the side door opened and out walked the sexy MILF office chick. Long black hair, glasses, purple blouse, black pants holding an umbrella. She walked away and had a phone call and just when I was about to go back inside she yelled for me to join her under the umbrella. She asked how my day was going and we complained about the rain and then she got to what she really wanted to ask me. Do you know who I could borrow $100 from till Friday? She asked softly. I was busy staring down her...

How I Met Your MILF

One of my coworkers was a tall older Korean mother. Most the Asian girls I've known tend to be really short, so when I meet a tall one they always catch my eye. Even though she was a fair bit older than me and a mommy, we still got along really well, working together on several projects but the most physical we'd ever gotten was one of us leaning over the other shoulder to see a computer screen better. That happened a lot, but I have always been hoping for something much more. Then there...

Old Enough to Be Your Milf

"I'm old enough to be your mother." I said to the kid who had just offered to buy me a drink. It was true that I was in the bar in hopes of perhaps meeting someone. But not to rob the proverbial cradle, and literal too. The youth who had boldly seated himself next to me and who was coming on to a woman twice his years bore an uncanny resemblance to my son at that age. "Actually, you bear a striking similarity to my mom." He said in quick reply. I was not thrown off by this, "OH? Do you...

MILF

It had been a hot summer afternoon when it all really began. Ryan's buddies had come over to play video games again as usual. I had heard them yelping and hollering down in the basement family room, making a racket only the way teenage boys can. It seemed like my teenage years were so very far behind me now, but I felt glad that Ryan was having such a great time with his friends. He would start dating soon and then things would change, so I held onto every moment for dear life. Soon the noise...

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