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This story begins when I was about 13 or 14. I was a thick boy with some baby fat on my six foot two inch wide-shouldered frame. Dark brown hair and glasses framed my clear complexion. I only knew my lips were full and nice because an older girl at school turned to me on the stairs one day. She spoke to her girl friend beside her and said, “Now those are kissable lips!” as she looked at me. I blushed and looked down; the moment and the girls were gone in a flash before I could think what to say. But I remembered. Another time in my painfully shy adolescence, a voluptuous classmate nearly gave me a heart attack when she ran onto the basketball court during intramurals and patted my ass in front of everyone! I never followed up with that flirt either, due to lack of confidence and my assumption that my fat body, plain-brown eyes, nerdy glasses and brown hair were just too unsexy.

I was still clueless about what girls were about, outside my fantasies based on what I gleaned from movies, TV commercials where women wore bras over sweaters, and National Geographic photos. I was lucky enough to find two old Playboy magazines, but they were of a vintage that showed impossible breasts and legs demurely crossed so no vaginal lips existed. I had discovered masturbation the year before when I found my older brother’s Playboy magazines in the basement, and furiously pumped my cock five or six times a day to keep the tension at bay. Everything seemed to find my cock straining to get released from my pants, sometimes causing great Catholic guilt and embarrassment.

This leads me to write about, in an ungainly fashion, Eric’s mother Mrs. Cohen (not her real name). Eric was my next door neighbor, handsome, Jewish, athletic and a genius. We chummed for years in the neighborhood after school. We went to different schools due to religion, but we didn’t care about that at all. Other kids made fun of him because of his looks (I later found out as a man he was gay), his brilliance, or his being a Jew. His family was the only Jewish family in a sea of Catholic homes. The houses sat all of 40 or 50 feet from each other. Eric’s parents lived with Eric and his autistic brother in one upstairs apartment opposite ours, with his grandparents in the downstairs apartment opposite my grandmother. His brother went to a special school, even on weekends many times. His father was a mean drunk who spent his time working or hanging out at the bars. It was an unhappy family, but somehow Eric and his mother always had a smile for me, and we got along famously.

One summer day a couple months before my story commences, Eric and I had been comparing each other’s penises behind some trees. No sex, just curious comparison. Later we were in his kitchen getting some milk when Eric mortified me by telling Mrs. Cohen, --his mother and my neighbor, “Mike’s penis is a lot bigger than mine.” I almost spit up, but she was cool about it and mumbled something about it being nobody’s business. But at that moment I noticed her as a woman and not just as “Eric’s mother.” Over the coming weeks I glanced at her during the usual comings and goings, and started seeing her in a sexual way. She asked that I call her by her given name, Martha, as Mrs. Cohen made her feel old, and she said I was getting big enough to call her by her first name. Martha was in her late 30’s, certainly no more than 40. She had dark wavy hair to her shoulders, a bit of a tummy after two children, but not fat. Her breasts were soft in appearance, full and jiggled a bit when she laughed. Her hips were wide but slid in a comely fashion into shapely legs and her ass was nice to imagine about under her skirts and pants. Martha, as I started to think of her, was coming into my fantasies more often.

Each summer Eric went to a Summer Camp for a couple weeks. It was during this time I was bored and given chores to do. As was her habit, Martha sunbathed in the small back yard abutting ours. I was cutting my grandmother’s small patches of lawn among her raised rock gardens. Only a hedge separated me from surreptitiously ogling Martha. She was alone in the back yard, with family all gone. She was lying a few feet from me on a folding chaise lounge. My sweaty body was pushing the hand mower and separated from my fantasy by only some low hedges. She wore a rather scandalous (for those days and that neighborhood) black bikini. She lay on her back with the top straps rolled down and the cups pulled as far off her breasts as possible for maximum exposure – though her nipples were covered.

Looking back, I’m sure she knew I was watching her. During a pause in my work she opened her eyes and said hi. After pleasantries she asked me to come and chat.

“Have a seat, Michael.” She said as she scooted to make room for me on the chair.

I was grateful to sit because I had a raging hard-on in my shorts. “How are you Mrs., er Martha.” (Witty wasn’t I?). We chatted about things I no longer remember, likely how Eric was and where was everybody (both houses were empty). As we talked Martha did not attempt to re-cover her breasts, but held a cup to one globe to hold it in place. As we spoke I saw her pussy outlined in her bottoms, with some dark hairs escaping from the sides. My dick was aching and throbbing in my summer shorts.

“Michael, I want you to know I let Eric know that telling me about your penis size was not cool.” I turned red as she added, “It’s OK not to talk about it, it is natural for boys to explore and be curious. But Eric shouldn’t have embarrassed you.” There was a pregnant pause and she asked if she should not have raised the subject. I mumbled no, looking down.

“Michael, you are a sweet boy, it is OK to wonder about sex.” “If you want to ask me anything, it’s OK.” I of course said nothing, but she asked if comparing my penis to Eric’s had satisfied my curiosity.

Feeling brave, I asked, “Why does Eric have no skin at the end and I do?” I thought, Oh! God, what did I just say? But Martha just took it in stride.

“Jews have a ceremony called a Bris, when a boy is young. All Jewish boys are circumcised. Gentiles don’t always have that done. But God made us all in his image, so it doesn’t really matter in the end I think.” After a pause, Martha asked, “Are you curious about anything else?”

Her openness was so different from my strict mother or the nuns at my school, I think I just felt comfortable that warm day. “Sometimes I touch myself and it feels good, but I’m afraid I do it too much or it will be bad for me.” She smiled, “Michael, most people touch themselves.” The ‘people’ nuance did not escape me. But I wondered how girls did it without a penis – I was so naive. She added, “Sex is special and hopefully loving when a man and woman can give great joy to each other, but when we are alone or have nobody in our life, playing with our private parts is a good way to feel better.” “How often do you masturbate?”

Oh God, I think I was turning into flames, I was blushing so hard, “Most days 3 or 4 times, I fibbed, but one time it was ten times.” She sucked in a little air and her breasts stood out with the breath.

“Well it seems everything works then!” She said, smiling, “Don’t worry about it Michael.” “What do you think about when you play with yourself?”

Now we were getting in uncharted territory. I wanted to tell her I hadn’t seen a pussy since little Annie showed me hers at 6 when I showed her mine at 5, nor did I tell her I dreamed of “my” Martha’s love box encased in dark hairy mystery. Instead, I said “Well I found a couple Playboy Magazines my brother left in the house before he moved out, so I look at them. Sometimes I think about girls I know.”

“Anybody I know?” she asked

“Once I thought about you.” Who the hell said that!? It wasn’t me, it couldn’t be! I wanted to die.

Martha looked at me, I think – my eyes were checking out the leaves of grass between my feet. I could feel her dark eyes on me. “Would you like a cool drink?” she asked as she tied her top.

I was saved! “Sure.” Maybe she didn’t hear me. Maybe she won’t tell my mother I’m a pervert. I could barely stand the conflict of guilt and extreme sexual tension.

We got up and Martha led the way to her back stairs. I followed her, looking at her ass wrapped so tightly in the bikini material flexing as she walked up the spiraling stairs. My cock was leaking and I looked down. A wet spot. Jeez, just what I need now. I tried to think of Carl Yastrzemski statistics; the Red Sox were the least sexy thing I could think of. No good, her ass kept waving at me saying ‘hi’.

In the kitchen, she bent into the cold refrigerator and asked if I wanted some lemonade. She popped up and poured two glasses. As she turned around I saw her nipples straining the black fabric. Her large C breasts were slightly sagged but full and the curves of her cleavage were directing my gaze to the two prominent nipples pointing at my chest.

After a sip she said, “Michael, you look uncomfortable. You can’t stand still and you have a pretty large erection – Don’t be embarrassed, please! I take it as quite a compliment.”

I was shy and speechless. She said, “Maybe I can help just a little.” And then she did the most amazing thing. She reached behind her, said, “Don’t tell anybody I did this.” and undid her bikini top. She lowered it and took the bra off. She stood there smiling as I soaked in every detail, every nuance. I took in the freckles in her cleavage, the quarter-sized areola. Her nipples were the size of my pinkie end joint and the whole thing was crinkled. Her breasts sagged only a little. There was one blue vein that made them so much more real than the faked ones in the magazines. I stood there numb and speechless.

“Can I touch them?”

“I don’t think we should do that Michael, but when you masturbate, it will be OK to think of me. I don’t mind. Do you think this will help until you get a girlfriend?” I nodded dumbly in response.

I don’t remember anything else about that day or how I got back home. I just remember staring at the most beautiful breasts I had ever (literally) seen. But the next day, I looked out my bedroom window, and Martha was across the way in her kitchen washing dishes in the sink. The kitchen windows were directly across from my bedroom windows. My shades were partly down and I could only see her from the waist up as I lay on my bed. She was wearing a plain white blouse with a couple buttons undone. I imagined I saw the swell of her cleavage. I felt so sexually aroused looking at the woman who said it was OK to play with myself. Looking at the woman who said it was OK to think of her.

Emboldened, I took off my shorts. My seven inch thick cock with sparse hair around it sprang above my small tight ball sack. I rubbed my legs and cupped my balls. Just then Martha looked across the space between the houses and saw me. She MUST have, because she stiffened and stopped drying the dish in her hands. I slowly stroked my cock, daring her to watch me. She stood there, silently. I stroked slowly, enjoying the feeling of my hand, thinking about Martha’s full breasts in front of me: imagining Martha washing dishes in the nude. I felt the pre-cum on my tip and spread it with my thumb. I felt my balls with one hand and stroked my cock, feeling the veins bulge. Martha put the dish down. If we had talked loudly, we could have spoken to each other, but we said nothing. She licked her lips. I saw her right hand go below the sink and her clothes rustled. I couldn’t be sure, but I think she was playing with her pussy, watching me beat my meat.

I groaned and then picked up the pace. It was my first cum of the day and I wouldn’t last too long. My cock throbbed in my fist and squirted thick ropes of cum up above my head, hitting the headboard. More cum spurted and hit me in the face and chest, finally dribbling onto my belly. I held my breath and electric tingles ran down my arms and legs; time stood still as I locked onto Martha’s eyes and tits. My legs had stiffened and toes curled. It was the best cum I had ever had.

Martha was watching me. I could see her frig herself by the movement of her arm, the rusting of her clothes and the jiggling of those magnificent tits. I lay there drenched in cooling cum all over my face and chest as I saw Martha support herself with one hand on the sink edge, and then her mouth opened in an O and she shuddered. A pause and she looked away, and then closed the shades of her window.

Nothing was ever said between us. Once more a few days later we had our mutual masturbation play on our private stage. But after that second time, although I tried to show myself on the bed, she closed the blinds in her kitchen window. Nothing ever again was ever said or done that was sexual between us. I have my suspicions she felt some regrets, but I don’t know. I felt lust, pleasure and thanks for this supportive woman helping me.

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I’m gonna share something personal today that is a major part of our lives. Me and Birgit haven’t shared an important news with you – we’re going to be parents. Yes, Birgit is pregnant since the first night in Ibiza. Weird, isn’t it? For many conservative people we might now seem officially the crazy ones, but it is our life and neither one of us see any problem with pregnancy and our common interest. Maybe you know that many pregnant women tend to be sexually more eager than usually.Like every...

True
3 years ago
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1st And Last Time My Chotu In A Pussy

Hello guys & gals, this is the 1st time I’ve seen a website like this where we can share our real life sex stories. I was browsing through porn sites yesterday (2nd Feb’15) and somehow reached this site, I was surprised and amazed with the stories,” THANK YOU; not sure how to ISS” and hope all the stories are real life. About me: This is Rakesh Cupid, athletic body type, working in a leading MNC and living in Hyderabad. I’ve stories from my childhood, even before the sperm production has...

Incest
2 years ago
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Hades Ch 01

Author’s note: This is my own retelling of a very common story, that of Hades and Persephone. This is my most favorite mythological love story. I’ve always identified with the transformation from innocent girl, Kore, to dark queen of the underworld, Persephone, and Hades is the ultimate strong male-love that. It’s more about passionate burning love than sex, though I plan on inserting more erotica into any further installments if there is an interest. Please feel free to let me know what you...

3 years ago
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Nights of Alsitor Hades Persephone II

Persephone gently pushed Hades away and stepped back, his hands reluctantly sliding from her flesh. She turned and walked toward the gate behind her. Still on his knees, he stared enthralled at the coxinant twists of her retreating buttocks. His callipygian captor paused and looked back at him and gave one word. "Follow." Hades scrambled to his feet and was fast on her heels, even as she retreated into a long, unlit tunnel. He followed her into darkness so thick he couldn't see his own hands,...

Fantasy & Sci-Fi
4 years ago
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Girlfriend8217s hot mom

Friends this is my first experience of sex, which turned to being an aunty lover all my life. This happened when I was 16 and in school. I am Amit, tall athletic body. I was a popular student in school because of sports. I am from a rich business family so I had lot of friends of both sexes. That time I had a big problem with the girls. The big problem was literally a big one – my cock is 9 inches and thick 4 inches. While the boys all were jealous of me I was getting nowhere with the girls....

3 years ago
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Telling Mom Im A Crossdresser Part 16 Hot talk With Mom

My night with Laci was amazing, It was like I could tell what she wanted and when she wanted it by instinct and she could do the same for me. All that weekend it was all I could think about as I continued on with a normal weekend. Nothing to special really just washing my normal and my Missy clothes as well as taking care of chores around the house. I went off with some friends at times to because even though I do have my Missy life I also like to keep my normal life as well.Eventually my...

Lesbian
3 years ago
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Archies Betty and Me HotdogChapter 14

For the rest of the week Betty and Midge continued with their 'job' of grooming Mr. Lodge's dogs. This left poor Cricket alone for most of these days. By Tuesday she got extremely bored and decided not to wait for the weekend before getting together with Pop's. She could be found every afternoon at the 'Chok'lit Shoppe' at the counter talking with Pop Tates. Every now and then they would disappear for fifteen, twenty minutes. And they would always use the same excuse, Pop's needed...

2 years ago
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Hot Pursuit of Mom

My Mom Tina, is 41 and attractive but difficult to get along with sometimes. She is medium height with long blonde hair and a beautiful face. Her Breasts are big, size 'D' and she loves to show off her cleavage. Her ass is nice to, a little big but in a hot way. The kind of ass you'd like to swat and watch jiggle for a second. She dresses to tease and not to please, she hasn't dated anyone in a few years now. My parents divorced when I was only 4, my Dad got frustrated with her selfishness and...

4 years ago
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Hot Massage For A Hot Mom

My name is David and I am 14 years old and I live alone with my 30 year old Mom. My Dad accidentally got my Mom pregnant so they decided to get married. From what my Mom tells me my Dad was a loving and proud father but he passed away in when I was a baby leaving my Mother as my sole parent. She did the best she could but her job as an elementary school teacher didn’t provide much for us. We made due though, we bought a one bedroom rancher out in the country, it was small but we liked to think...

2 years ago
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Hades Ch 04

Gifts of every decadent form began arriving at the estate of Kore’s foster family that morning. Fragrant floral arrangements, statues in effigy of the soon-to-be betrothed, sweets filled with nectar and honey and nuts, pastries piled high on Long tables, silk fabrics of every jewel tone hue imaginable. All of these had been streaming in for days, trumpeting the arrival of the prosperous Certese family. The servants worked for days cleaning, cooking and creating a fitting house to greet the...

1 year ago
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Archies Betty and Me HotdogChapter 10

After telling her parents the good news about the job, she returned to her private phone and gave a call to Midge's about it. Rrrrrinng! Rrrrrinng! "Hello?" "Hello Mrs. Klump. This is Betty Cooper. Is Midge there?" Betty answered. "Why hello Betty," Mrs. Klump responded. "Hang on I'll get her." "Hi Bets! What's going on?" Midge asked. "You won't believe this, but Mr. Lodge just offered you and me a summer job for eight hundred a week," Betty said cheerfully. "No...

2 years ago
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Banged Friend8217s Hot Mom

Hello friends, my name is Sid and I am from Pune. I am 21 year old. This story is about me and my friend’s hot mom Neena. Neena aunty is Umang’s mom. Umang and I have been studying together since our school time. But now he is in B.Sc and I am doing my B-Tech in engineering. This happened last month when I got the chance to fuck this hot mom. I was going for a small trip to Lonavala and wanted to check whether Umang would like to join. So I went to his home that afternoon. Ding dong, I rang the...

3 years ago
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Umangrsquos Hot Mom

Hello friends, my name is Vipul and I am from Mumbai. Basically I am a Gujarati and live in boriwali. This story is about me and my friend’s hot mom Neena. Neena aunty is Umang’s mom. Umang and I have been studying togther since our school time. But now he is in B.Sc and I am doing my diploma in engineering. This happened last month when I got the chance to fuck this hot mom. I was going for a small trip to Pune and wanted to check whether Umang would like to join. So I went to his home that...

3 years ago
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Hot bhabhi gangbanged during a photoshoot

This story is based on an episode from Savita Bhabhi comics, which you can read . Savita was dressed in a sexy saree that would grab any man’s attention. Ashok and Savita were invited by Bharat and other board members she sucked off yesterday. They made an offer that Savita could not resist. They were ready to publish a magazine for women like Savita who were into business. They wanted to do a photoshoot with Savita at her restaurant. This would boost the fame of her revenue, and she will be...

3 years ago
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22yo Bottom Get Plowed in the Hottub

Last Friday Kip and I had an awesome day snowboarding (blue skies no wind, although we could do with a little more snow). After riding until four o’clock, we rode down the run called Four O’Clock here at Breckenridge then we jumped on one of the local buses and went down to one of the local breweries for a beer. While sitting at the bar I checked some emails and Kip checked the online gay hookup app Grindr and saw that we had a message. Kip showed me the message and the photo of the very cute...

3 years ago
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Hottub Foursome

Last night (Friday night and St. Paddy’s day) Kip and I had a big night. No snow here and Spring Break crowds so we didn’t expect to be snowboarding early on Saturday morning. Some guys we know from Denver were up so it was 4 gay guys hitting the town!!! Kip’s sister was spending the weekend down in Fort Collins or Boulder or somewhere so we had the house to ourselves. 4 gay guys (Kip and I consider ourselves bi), pretty much unlimited speedo supply, a little bit of booze and a hottub – what...

2 years ago
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Friend mom

My Best Friend's Hot Mom Will Blake was my best friend. We’d known each other since middle school and now, the Summer after graduation, we were headed to be rommies together at college. I was at Will’s as usual. He was taking a shower and I was waiting for him to finish and we were going out – hopefully to nail some fresh pussy. When new conquests were on the agenda we went across town to hang in the other high school’s area. We knew all the k**s from our school, but the k**s that went to...

4 years ago
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Friend fuck my mom

Hello readers sameer here. I am back with another real story. This story is of one of my friend. His name is Sanjay. He have given me the information and asked me to write for him. Hope you all would like the incident. Sanjay is a 21 year old boy doing his graduation. His father is in navy and comes home once in a six months only for 15 days. His mother is a very sexy lady and very attractive. She is 40 years old, but looks like 35, her hair reach to her ass, every one who sees her would love...

Incest
3 years ago
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Hot Mom

I grew up in the sixties which was perfect for a young sex addict. Many girls and women did not wear a bra and if they did it was a sexy sheer bra, which allowed their nipples to poke out against their clothing. My hot sexy mom was one of these women. She never wore a bra or panties and my cock was always rock hard around her. My parents were divorced and I lived with thirty seven year old Mom. She never wore much around the house and I was always getting glimpses of her perfect perky tits, her...

3 years ago
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MY HOT MOM

My mom April was up to her neck in the hot tub with her head leaning back and her arms on the side sighing in pleasure and her pussy was feeling hotter than the water did As usual she enjoyed the freedom of being naked in her hot tub and the wicked feeling she had right now as she lay there. No one could see her as the nearest neighbour lived miles away from her here in the foothills. No one ever came near not even ramblers or hunters as there was no game to attract them and there was only one...

2 years ago
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Home Run Friend preys on hot mom

I had just gotten done with baseball practice and I was exhausted. It was a strenuous workout, and I was looking forward to getting a good night sleep. My teammate Jeff dropped me off at the foot of the driveway. I could barely step out of his dodge pickup truck I was so sore. We had lost two games in a row, so our coaches were pissed off and made us run like crazy.I told Jeff goodbye and limped up our short driveway. We had recently moved into a new subdivision where all of the houses looked...

2 years ago
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My Hot Mom

Hi mera name ravi he me mumbai se hu ye story meri aur meri hot mom ki he. Me 19 kahu aur mom 43 ki he par wo lagti 35 ki.Mom ka name ”hetal” he 36-32-34 fig he uska mast lagiti to hua yuki. Hum ghar me 3 log hi he . Me papa aur mom jab wo log so jate to me tv pe porn filme dekhta aur muth marth wo bhi pura naga hoke. To ek din me muth mar raha tha ki mom aa gai mi pura naga th aur land hila rahath. Mom muje aur land ko dekha rai thi par wo kuch boli nai aur chali gai. Fir to ye roj hota 10 din...

4 years ago
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From Masturbating In The Bathroom To Fucking My Friend8217s Hotass Mom

My name is Mohan Patel and i live in America. This story is about my best friend’s hot ass mom and this is a completely true story. So I am nineteen years old, and my best friend is a year younger then me and is eighteen years old. We both go to the same college. I have known my friend, who’s name is rajan, since i was three years old. Rajan’s mom, sapna aunty got married at a really early age and is only 39 years old. She is hot as hell. She could have been a model or an actress if she was...

2 years ago
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Friend8217s Hot And Needy Mom

Amit and Manjeet were best friends who had studied in a government school in a very backward village in Punjab. Amit was three years his senior but since they had been neighbors they had become friends at a very young age. Amit’s dad owned a huge farm so sent him to Delhi to study further while Manjeet was left alone in village with his widowed mother Uma, unable to continue his higher studies. Manjeet could not work in farms due to his weak body and underfeeding and hence he lost his job...

2 years ago
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Chaddi Me Haddi

Hi friends its Sumit Bang back with a new series of stories for you. After overwhelming support by all the ISS readers I owe a ton of thanks to them. This series is a story of a part of my sex life and as the story is little bit long so it will be presented in parts. I’m also thankful to ISS for providing such platform which helped me to get in contact fuck many girls and aunties. So coming to the story this story is about my friend vrush (name changed). Being in an engineering college I met...

1 year ago
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Hot Moms

Do you get a hard-on thinking about the lovely older women? Well, many subreddits are dedicated to MILFs or whatever, but here you only have moms… aka real MILFs, not just older chicks who look like them. So, if you are interested in seeing some older beauties who are considered to be hot and fuckable, you are welcome to browse through r/HotMoms/.There is not much else to be said about this subreddit; I think that is the gist of it. I mean, you are either into older women, or you are not,...

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