I moved back home after college to look for a job and save some money. I didn't have a car just yet so whenever I would browse tinder or the other dating apps I always kept the radius really small. As a younger guy I was always into older women (who isn't?) so I didn't have an upper age limit in the search settings. Maybe I'd get lucky and match with a hot MILF!

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Sometimes when I would be watching tv I'd just swipe right on my phone, not even looking. I was laying in bed, checking my notifications when I noticed I had a new match. The picture looked really familiar so I clicked on her profile. The age said 41, her name was Jen, and I knew I had seen her somewhere before, I just couldn't figure out where. She had black hair, big tits, and was pretty busty. I thought to myself 'fuck it' and messaged her.

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Me: Hey there :)

Jen: Hey neighbor ;)

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It hit me right away. She lived a few houses down. I've seen her walking her dog before and a couple times around town. We'd never interacted before. I thought to myself 'is she married?'. I had never seen her with her husband if she had one, so I didn't worry about it and messaged her back.

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Me: I knew I recognized you!!

Jen: I sure recognized you :) You're a little young to be matching with me aren't you?

Me: Oh I don't think so :) What do you think?

Jen: Secret time: I love younger guys. What're you looking for on here?

Me: Nothing serious, just fun really

Jen: Me too.

Me: Good :) I have to ask, are you married?

Jen: Yes I am. To make a long story short, my husband is disabled/wheelchair bound. We agreed to an open marriage a long time ago. Sorry if that's weird, but it just is what it is.

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We messaged back and forth for a while before exchanging numbers and planned on getting some drinks at the local bar later that night. I didn't have a car to get there but it was only a few blocks so I walked over there when the time came. I got there first and waited to order a drink for when she arrived. After a few minutes Jen walked in. She was wearing jeans, and a black v-type shirt that showed off as much cleavage as it possibly could. Her tits were massive. She was busty so she had a really big wide ass too. She smiled at me and took a seat next to me at the bar.

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We ordered a couple drinks and chatted casually for a bit until she straight up started talking about sex. She had just joined the dating app game and hadn't met anyone yet. She asked if I had gotten laid yet using them and I said yes and shared some stories with her. We got onto the subject of kinks and I nervously told her a few of mine before asking her what she's into. I couldn't help but stare at her tits from time to time and I'm sure she noticed.

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"Honestly, this might sound weird but nothing makes me orgasm harder than anal," She said.

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I couldn't hide my smile when she said it. "I've never done it," I replied.

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"Oh really? Are you not into that?" She asked, looking a little embarrassed.

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"No no, I've just never had the chance! I'd do it in a heartbeat", I replied.

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"Maybe after this drink we can go back to your place and try it," She said with a devilish smile on her face. I stuttered my way through agreeing and I paid the tab. Thank god my parents were out on a date night.

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We took her car back since she drove there. I can't remember what we were talking about on the way but without saying anything or acknowledging it, she reached her right hand over and slowly rubbed my crotch over my pants as she drove.

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"Mmm I'm excited that I'll be your first," She said as she pulled up in front of my house. We got out of the car and walked inside. I asked her if she wanted anything to drink.

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"No I'm okay. Show me to your bedroom," She said with a smile.

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I took her upstairs, made sure my parents were still gone and led her to my room and closed the door. She immediately started rubbing my cock over my pants again and looked me in the eyes.

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"Will you show it to me?" She said with puppy dog eyes.

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"Of course," I stammered. I opened my belt and she got down onto her knees in front of me. I opened my jeans and she pulled them down to my ankles. She gave my cock another rub over my briefs. I was so hard that it almost hurt with the briefs holding my cock to the side like that. I started to pull the waistband down and my cock sprung out, only an inch or two in front of her face.

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"My my, thats a nice cock honey," she said as she took one hand and squeezed my shaft. I felt her other hand wrap around my balls and give it a light tug. She pumped it slowly once or twice before opening her mouth and pulling my throbbing cock into it. I groaned as she took half of me in, still pumping my shaft with her hand.

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Her pace increased quickly, and after a few seconds her hand left my shaft, and her lips were hitting the base of my cock as she swallowed my entire dick. Her hands gently wrapped behind my waist and pulled on me in motion with her sucking. I felt her spit drip down my balls as I felt the head of my cock pass into her throat. I could tell I wasn't going to last long so I tried to slow her down a bit by pulling my hips back.

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"Sorry, I just think I'm already getting close," I said, a little embarrassed.

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"Thats okay! I don't want you cumming before you get your big moment. Should we do it now?" She asked with that smirk again.

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"Yes please," I replied, returning the smile.

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Jen stood up and took her top off. Her tits were giant. My cock pulsed just looking at them. She didn't waste any time, and took her pants and panties off. Without saying anything she crawled onto the edge of the bed and bent over deep, with her face buried on the bed. She reached both hands back and pulled her huge ass apart for me. Her pussy was glistening and her asshole stared back at me.

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"Are you ready for me honey?" She asked

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I looked down at my throbbing cock, dripping in her spit and replied "Yeah are you?". She nodded against the bed. I stood right up against the edge of the bed, gripped the base of my cock and pointed it at her ass. I pushed the head of my cock against her asshole lightly at first, then a little harder. It felt like her asshole sucked the head of my cock into her and it felt so good. It was really tight around the base of my head. We both let out a simultaneous sigh and I grabbed her hips and pushed all the way in.

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"Fuck yes baby, that's right," She said encouragingly and out of breath.

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Hearing that only made me harder, and I started to thrust harder into her. She was really loud as I gripped her hips hard and fucked her ass harder and harder. I remember it being ridiculously tight and warm. I couldn't help but be loud too. My balls clapped against her pussy as I buried my cock in her ass over and over. I felt my cock stiffen more and more and could tell I was close to exploding.

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"I'm getting close," I told her in between thrusts

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"Good baby, cum all over my ass."

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I pulled on her hips as hard as I could and gave her one or two of my hardest pumps, pulling my cock out a millisecond before it started spraying all over. She held her ass open for me as I pumped out ropes of cum, hitting her cheeks, shooting into her open asshole, and dripping down her pussy.

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"Fuck yes baby, give me all of your cum!" She squealed. I stared at her cum drenched ass as my orgasm subsided. She giggled and sat up.

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"Did that feel good honey?" She asked, looking at my tired cock. I think I just nodded, I was on cloud nine.

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"Good. Next time will be even better," She said smirking. "I need to get home and take care of my husband, is it alright if I head out?".

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I nodded again. My parents would be home soon anyways. She pulled her panties back up over her cum drenched ass, squeezed into her jeans, and put her top back on. She gave me a kiss on the cheek and walked out of my room and back to her car. We met a few more times, maybe I'll write about those soon.

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Thanks for reading!