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I had a friend in high school whose dad worked on the railroad. This meant that he was gone most weekends. His parents had divorced long ago and his dad had remarried a woman around ten years younger than him. They had two k**s together.

Blake and his stepmom, Jen, were very close and she would allow him to have house parties during the weekends his dad was gone. It was one of these weekends, which me and my best friend Collin never missed. Our parents knew we were staying at Blake's house, but had no idea about the parties. It was usually around one in the morning when the rest of the party had to go home. This would leave just me, Collin, Blake, and Jen there and we would always hang out until early in the morning.

This weekend was a little bit different. My friend Blake, who always was with a good looking girl, had a new girlfriend, who was with us. The five of us sat around and drank as usual, until Blake's girlfriend said that she needed to get home soon. Blake then left to give her a ride home.

Collin and I went upstairs to the sectional where we always slept when we stayed. We put in a movie and Jen decided to stay up and watch it with us. There was plenty room on the sectional and she sat in the curve of it, with me laying to her right and Collin sitting up to her left. She had changed out of the jeans she was wearing that night and had put on some running shorts. She was only about 5'8" but she had long, tone legs and I always loved to watch the outline of her calve muscles appear with every step she took. She had also taken out her contacts and was wearing a pair of reading glasses. Her shoulder length, light brown hair and green eyes were a perfect match for the glasses.

As she sat down she curled her legs towards my side and they stopped just shy of my head. The light scent of body lotion on her legs was enough to arouse me but when I looked up and saw her freshly manicured toes, painted a carnation pink, I had to make sure the blanket concealed my throbbing erection. After a while I was able to get myself under control and started watching the movie. I was pretty tired and it wasn't far into the movie when I dozed off.

I awoke to some whispering,"But what if Blake comes home?" "He is with Chrystina, he's not going to be home tonight." I heard Jen let out a little sigh, but didn't hear another word. I slowly opened my eyes and saw Collin leaning back on the couch. Jen's hand was under his blanket and I could see it slowly moving up and down. As I layed there watching I began stroking myself making sure not to be noticed.

Soon Jen slowly pulled back the blanket, I could see the outline of Collin's erection as the friction of the blanket pulled it downwards. As the blanket slid off of him, his rock hard cock sprung back to its usual position and they both giggled quietly. Collin had already taken off his shirt and Jen slowly kissed his chest as she made her way down. After kissing the head, her mouth opened and began to envelope his cock. Collin gasped in pleasure and his eyes closed as she worked her way down. Soon Collin opened up his eyes and began working his way up Jen's shirt. By this time Jen's feet were still by my head and her knees were resting on the couch. Jen's shirt rested loosely on her body and I could see perfectly up it from my position. As Collin tugged her bra both of her breast fell out simultaneously. They were a good handful in size, as I could tell from Collin's hand groping them. He squeezed her left breast firmly and then worked his finger to her nipple. I could see that it was already hard, but when the tv flashed brightly I could see that she now had goose bumps around her nipple.

I couldn't handle laying there any longer. I gently kissed the sole of her foot. She was startled and her head popped up and she looked at me. She must have seen the hunger in my eyes because she didn't speak; she gave me an inviting smile and went back down on Collin. I slowly kissed my way up her legs, making my way to her shorts. I pulled her shorts down to her knees. I was too anxious to take them the rest of the way off. I began teasing the lower part of her lips with my tongue. I pulled my head back and noticed a wrinkle of skin leading from the bottom of her pussy to her asshole. I knew from my limited experience that girls my age didn't like their asses played with, but I followed the wrinkle with my tongue. She moaned as I did this so I traced around her ass and worked my way back down. I then took her shorts all the way off as Collin took her top off. She was now able to spread her legs enough for my head to fit in between. As soon as my tongue reached her clit her legs began to shake and within a minute she came.

She then sat up in between me and Collin and began kissing me, while she stroked on both of us. She then took turns sucking, kissing, and stroking us as we both touched her all over. I wanted to be the first one inside of her, so I stood up and pulled her legs towards me, laying her on her back with her head in Collin's lap. Like every high school boy, I always kept a condom in my wallet. I got my wallet out of my pants and took out the condom. Jen's legs were spread apart and I sat in between them, taking the condom out of the wrapper. Jen sat up a little and gently grabbed the condom from my hand and set it on the floor.

By this time Jen was dripping wet and her hand guided me inside of her. This was my first time without a condom and I could feel every inch of her pink flesh as I entered her. After about a minute I knew I couldn't stay in her a second longer without cumming, so I pulled out. Collin was more than eager to be inside of her and didn't waste any time. I began kissing her and with Collin inside of her, Jen's legs began to shake again as perspiration rolled down her forehead. I put my dick back into her mouth and as she moaned it sent intense pulses through me. I couldn't hold any longer and I began to shoot my load. I came hard in three throbs. The first time my cock throbbed suddenly in Jen's mouth, I tried to pull it out but she grabbed my ass forcing me to leave it in. The next two throbs were much stronger than the first and I could feel my hot cum as it filled her mouth. She then pushed my cock out of her mouth, took a breath of air, and swallowed. Soon after this Collin pulled out of her and shot his load. Right when Collin pulled out Jen began to stroking him vigorously. The first shot landed between Jen's breast as the subsequent ones fell shorter and shorter making a trail to her pussy with the rest dripping onto her hand as she continued to stroke him afterwards.

Collin and I were very competitive with each other (in everything from school, to sports, to sex) and I knew his dick had made her cum and mine hadn't. I was hard again within a minute after cumming and as soon as Collin wiped his cum off on a blanket I was back inside of Jen. Even this second time around my cock was extremely sensitive, still not used to being without a condom. After a minute or so I turned Jen over and we began to have sex doggy style. My dick was in her far deeper than before and Jen buried her face in the couch to keep her moans down. Soon I felt her legs shake and I was glad because I knew I couldn't last much longer. As she came, the inside of her vagina gripped tightly around me. I pushed inside her as far as I could, burying my seed. I gave a few more pumps to make sure I got every last drop inside of her, then I pulled out.

To my suprise, Collin wanted to take her doggy style too and shortly after I pulled out he was back inside of her. By this time she whimpered,"Collin, I can't handle any more." Collin was the most selfish person I have ever met though and after she said that he went harder than ever. Luckily for Jen, Collin couldn't last much longer. I saw him give a final thrust, trying to get his cum deeper inside of her than mine. He then pulled out and Jen rolled onto her back exhausted.

We all just laid there for a while, taking in what had happened. Finally, Jen reached down and touched the stream of cum that was leaking out of her. She gave us a worried look and made us swear over and over again that, "This would be our secrete, because you know what would happen if anybody found out." Collin and I never mentioned it again, but I still stayed the night at Blake's house many times after that ;) (as I am sure Collin did too)










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Hi, Maddy here back again with another hot MILF fantasy story of partner swap. This happened after a 46-year-old MILF named Leela (name changed) replied after reading my previous story, A brief about myself, I am a 25-year-old handsome guy from Bangalore. I have a special attraction towards sexually attractive MILFs. I believe not in jumping in bed with all and will make out only if we connect well. I do treat women with great respect and make them be in their comfort zone. Coming to the...

2 years ago
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The Worlds First Futa Transformed Into a FutaChapter 3 Futarsquos First MILF

April 17th, 2047 “So, your boyfriend’s mom walks in on you naked on her living room couch, your new futa-dick hard and thrusting before you. That sounds ... interesting,” said Adelia Tash, the talk show host sitting beside me on the couch before her studio audience. The cameras rolled, the lights shining down on us, illuminating us for the entire world to watch as the interview was streamed across the internet. “Yeah,” I said, giving a soft chuckled. “But, I wasn’t hard. Yet.” I glanced out...

3 years ago
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Milf milf milf

Hi I'm jamie, I'm 15 years old, I live in at home with my mum,dad and sister. I'm 5'11 short black spikey hair, average body and a 9 inch dick. My friend Charlie also lives in addingham with his mother who's divorced. My story starts now, I was staying over at my mate Charlie's house. We played on the Xbox from 2-5 playing FIFA then Charlie's Milf mother called us for dinner. Jill ( Charlie's mother) was the most beautiful girl I had ever seen, she was 45 but looked in her late...

2 years ago
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My Girlfriends Mom is a MILF

I went over my girlfriend’s house to pick her up for our prom date. Her MILF mom Jackie met me at the door. She told me Becky was still getting ready but she needed to talk to me in private. She led me through her house and down to the basement. I enjoyed the trip since I could watch her marvelous ass sway as she walked. Jackie is in her early forties. She is shorter than Becky. She is 5’ 3” tall and curvy. She has great tits, 38DD cup and her ass is remarkable. She has piercing green eyes and...

4 years ago
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Dinner Date With a MILF

Background: After winning a bet with an entity in a dream, you are able to mind control whomever you please. Characters: Mrs. Busty: A 5'4" orange haired milf with H-cup titties, a luscious ass, and the best blowjob lips you've ever seen. After thoroughly dominating her, she becomes your 24 hour fucktoy. Mrs. Done: A 5'3''asian MILF, in her thirties, has watermelon tits, an ass the size of two medicine balls, black hair that went to her shoulders, and a very thick Chinese accent. Mrs. Blondy: A...

MILF
2 years ago
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The horny adeventures of sexy milf

The horny adeventures of sexy milf,Jackie Anderson sighed as she stood looking in the full length mirror after stepping out of the shower. It had been about a year since the divorce and her k**s were away for the summer with their father. Since she didn’t have them to help around the house, she had decided to hire two college students for the summer. They should be arriving any time to stay and help her keep the house and yard in order. She looked at her reflection and smiled. At 35 years old,...

4 years ago
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Katie The Hot Milf

Ashley Levy was Scott Nielsen’s girlfriend.  They had been dating for about six months.  When Ashley started bringing him around to the house, he seemed fascinated with her mother. Now Ashley’s mother was not your typical mom.  She was what most men called a “Milf.”  Katie wore crop tops with no bra which were always see through.  She wore tight yoga pants with no panties where you could see her camel toe.She would sunbathe with her bikini bottom but was always topless.  She had big breasts. ...

MILF
4 years ago
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Training the MILF Part 3 Owning the MILF

Susan arrived at Devon’s place filled with anticipation. He’d promised her a reward for being such a good girl. She giggled a little. No one had ever called her a good girl.She entered the training room, removed her long coat, and kneeled at his feet with her gaze lowered. She was completely naked and felt a mix of vulnerability and lusty need.“Look at my slut, ready for me,” Devon praised her. “You’ve come a long way in such a short time, my dear.”Susan kept her head down but nodded in...

MILF
2 years ago
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My First Milf

This a true story that took place my junior year highschool.I always had a thing for milfs, mature women , cougars and what ever name there is out there to describe a sexy older women. But up until this point in my life I never had the chance to have a sexual experience with one them. This soon will change in a few short weeks.I was t_een just getting ready to begin my Junior year in high school, I was having a really good time, especially with the ladies, I never was into cliques and all but...

1 year ago
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I Like to Dip Mine in Milf

Oh, the MILF. I had never heard the word before, but know it all too well now. I was just a broke college boy, looking for some extra cash. My dad suggested lawn care. He further suggested I look for work on one of the wealthiest streets in our city - Cherry Blossom Lane. His theory was the rich don't like to mow their own grass. Turns out Pops was right, but some of the residents needed more than just their lawns handled. Most of the lovelies on Cherry Blossom Lane were stay-at-home moms who...

MILF
1 year ago
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Fucking My Favorite MILF

Fucking My Favorite Blonde MILF Getting to know herI have several damn hot stories to tell about a very special woman I have been seeing for almost 6 years. I have already posted one I wrote, and one written by her. The titles of those stories refer to her as “My Favorite Milf ”. I had a few people tell me how they felt those stories, as well as any future ones I post about her, could be better if they new more about the real person she is. So here are a bunch of short tales that I hope you...

3 years ago
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Getting Lucky With A Bengali Milf

Hi everyone, I am Raj, age 24. I am in my final year of my MBA. Just like any young guy, I, too, had many fantasies of my own. I had many friends of my age who used to hang out with their girlfriends. I used to feel jealous as I never had any girlfriend. I was always attracted to older women around me, who we call Milfs. I fantasized about my college lady professors, any neighborhood bhabhi, or any other married lady. But inside, I always knew I would never be able to get one in my life. But a...

4 years ago
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First time with sexy divorced milf

This all starts a few years ago while I was working at a bar. A group of much older women came in drinking and generally just having fun. One of the 4 I caught motioning she thought I was hot while the others nodded their heads to agree. I was so turned on by seeing this, I had always fantasized being with a mature woman. Towards the end of the night I let them stay a little later while I finished closing. The one that had continue to gaze at me had the sexiest milf face, blonde hair, blue...

4 years ago
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Mrs Taylor THE MILF

This a 6-Part series. I hope you enjoy! And PLEASE comment below what you think as I love feedback! PART 1: Pure Anal with Mrs. Taylor SUMMARY: Luke is a student in college in California. He is on Spring Break. He is staying at his home for the weekend while his family is away on a cruise. He plans on taking care of the property for the weekend, then flying down to Mexico with friends for vacation. Everything is going according to plan until he meets his new neighbor...

4 years ago
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Thick Mickie the MILF

“Hello, how are you?" Jordan said, behind the camera.“Fine, how are you, sweetheart?"“Good. Good. We got a sweet one, do we? Would you mind telling the masses what your name is?” he said.“Sure. Mickie. Like the song, ’Hey Mickie,’” Mickie said, with a smile. “But, you’re kind of young, aren’t you?”“I know the song. You got jokes, do you? So, Mickie, I ask all the women that come here this. What made you do porn?” Jordan said.“Well, believe it or not... This isn’t my first time doing...

MILF
2 years ago
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The Dogooder MILF

Do-gooder. She has a hand in everything, teaching the kids, help seniors, fund raising, donuts and coffee and anything else. I am not sure when I started to be interested in her and certainly not sure why. She had that used to be hot look but was really forty and frumpy. But there was that smile and she was hands on. I remember the first time she put her hand on my shoulder, I got that feeling, tingling. Her hair is shoulder length but doesn’t do anything, it either needs to be washed...

2 years ago
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The Busy Milf

When summer happened, Grace Anderson gave her nanny time off.  She cancelled all her usual appointments to keep herself pampered.  She became a full-time mommy who cared for her kids.  She arranged daily activities and took the tots to the beach for the weekends.She cooked and cleaned and did all the chores that her hired staff usually did.  She played the role of mom for the summer.  Her husband got a kick out of his wife, who was usually pampered hand and foot.  She wanted her children to...

MILF
2 years ago
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Slutty Pierced MILF

Slutty Pierced MILF The caption that went along with her pictures read: I am a slutty pierced MILF who likes to show off sometimes. Her location was USA and her age group was twenty-two to thirty. There were five pictures of her. The first picture was of her standing in the shower, fully dressed, and taking her own picture with her phone in the mirror. That was when she got her full height in the picture. In the second picture she was wearing a lavender bra, pink panties, and facing...

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