Found this subreddit about a week ago and once I did, I knew I had to sign up to tell some of my stories. First a little about me. Names Jake, I'm 27, 6"1' and just as guys like to say to make it sound like we're not the conceded bastards we really are, "I've been told that I'm a pretty good looking guy" I love it when people say that, it's like they're saying Am I handsome? I don't know. I'm just repeating what other people say. Anyways I've always loved older women, like ever since I was 5, my crushes would always steer toward the girls who were like 3 or 4 times my age, my first kiss was from a girl who was 12 when I was 7 and as I got older that number increased and throughout the most of my adult life I've been with many mature women. When I was 19 I met Nicole. Nicole was not my first older woman. She was a friend of a friends mom. Me and like 5 other guys would always go over his house during the school year and hang out, cheat off each other in homework assignments and play video games, Dude had a pretty sweet house. Matt was the guys name, His mom Nicole was about 38, would always wear these flower print strap tank tops with ample C cup cleavage showing, not a lot but just enough to let you know she had a pretty decent pair underneath, tight jeans sometimes a skirt. She kinda reminded me of the actress Kyra Sedgwick smile wise, One time Matt called her to the kitchen and you could tell he was upset with her he was yelling in a whispering voice basically calling her a slut/whore but saying she's dressing like one so as to not outright disrespect his mother. Me and the guys would just snicker and laugh and try to hide our smiles when he would come back in. He obviously knew what she was trying to do even though she would insist she wasn't. One day after me and the boys were playing a game of touch football handjob in the car his backyard and Nicole was in the kitchen washing dishes every now and then I would catch her staring out at us. When she saw me catch her staring she would divert her eyes from mine and yell out "Go Matty" and cheer for him as a cover. I decided I wanted to go in and grab a bottle of water. I walk in and before I could even ask she handed me a bottle from the fridge. She stood there watching me drink it as if she was waiting on me to finish so she could take a swig. It was pretty damn awkward for a moment with me just standing there drinking and her just 2 feet away not saying anything, I finished it and I tried my hardest not to belch in front of her. She would just stand there with like a half smile on her face looking me up and down. She broke her silence finally saying "So you boys having fun" I remember I said "Yeah it's always fun whooping your son's ass in any game" I laughed to let her know I was joking not sure how she would take it but she chuckled. I remember I was wearing a yellow printed muscle T and She looked at my arms and said wow you must work out alot and grabbed one of my biceps and gave sort or a playful squeeze. I told her yeah I lifted and I said "I noticed you checking us out from the window", thats when she got all flustered she said "Noooo no I was just, no" I said sarcastically "It's okay I'll let it slide this one time missy but from now on remember, my eyes are up here" and she laughed this big nervous laugh I could tell my boldness was making her a little nervous because she was turning red but she was also touching me a lot more, on my shoulders and chest. My dick started to stiffen and I was wondering if she would notice. She mentioned that she wanted to get back into the gym and I think I'm sure I gave her the o'ld "What? You?" No!" and she said she wanted to start doing a little weightlifting but she didn't want to turn into She-Hulk we laughed and I told her I would be able to help her out with that and she was like"Really?" "Would you like set up a plan or something" I told her "Sure" she said "What about cardio because I really need to get back on the treadmill" I said "Oh don't worry I'll have you sweating" and gave her this sort of smirk "Yeah?" she said and grabbed her collar bone and started rubbing it and sort of bit her the side of her lip a little bit. I wanted to take her on the Island kitchen countertop they had at that very moment but that's when Matt came in and started getting on me for being in here talking to his mom. He tried to smack me in the balls when I passed by him. When me and the guys were getting ready to leave Matts, Nicole walked us all to the door I was last leaving out and she stopped me and said "Don't forget I'm serious about that training session" I said "Just let me know, get my number Matt" she smiled and said "Okay" and As I walked out her hand that was on loading... my shoulder when she stopped me, went from my back and she kinda grazed my butt enough for me to notice. I wondered if Matt had seen her do that. I didn't care. It was about three weeks or so is it illegal to have sex in a car before I heard from her again, then one day I got a call on my LG Chocolate phone, remember those aren t pillows? No ? Okay but I get a call and it's her. She asked if I road head pics was busy and if she could get a session in at the gym with me. I agree because I was actually going there later that day anyway. She said to meet her at her house and she would drive. So I get over there, Matt had left for his Dad's for the weekend. She invited me in and I sat on the couch and she went upstairs for about 10 minutes, then she calls me up I ask her if everything was okay she didn't say anything so I walk up the stairs and around the corner I see a door open at the end of the hallway with a light on I walk down to it, when I get there she's standing in the middle of the room with her arms folded she looks up at me and tells me that The reason she was taking so long is because she was sucking dick in a car feeling conflicted" I said "about what"? she says "I don't want this to sound weird or anything but I've been thinking about you for the past couple fucking in public of days" I was like really? she said "Yeah" she began to try and explain herself but I wasn't really paying attention. I wanted her and from what it sounded like, she wanted me too, she looked so hot with her hair tied back. I walked right up to her, held her behind her head and kissed her deep, right in mid-sentence. She murmured trying to speak but didn't try to pull away So I moved from her lips down to her neck to where she finally said "Are you sure you want to do this? Was she serious? Still kissing passionately I walk her over to the end of her bed and laid her down. She lifts her arms so I could slide her top up over her head, I kissed around her neck again this time moving down toward her chest. She rubbed my cock out side of my gym shorts, her breathing became shorter, softly whispering in my ear how good I felt on her skin. She gripped my shirt tight, pulling it out of shape. I backed away breaking her clutch and I slid her sweatpants off. I kissed down her legs slowly until I got to her panties. Kissed and licked the fabric outside of her pussy, She started moaning louder and grabbing her tits. I pulled her panties off, she had a little bit of a bush but it was okay. I went down and lightly licked the outside and around her pussy before plunging my tongue in and ravishing it. She was moaning louder and begin pulling my hair, so I stuck two fingers (my middle and ring finger) in her pussy while still licking and sucking her clit, this drove her fucking wild. She started trying to gyrate and turn her hips and tried shut her legs from the intensity but I moved up and placed more of my weight on her to keep her still and held legs open. We had just began. There was no way I was letting her throw in the towel yet. No, I kept fingering her bringing her to the edge then slowing up. Within minutes she came and let out a loud forceful groan followed by a series of gasps. I watched her body shake and felt her legs twitch as she came this turned me on even more so I pulled her up by her arms she immediately dropped down to her knees but I pulled her back up I know she was probably still tender and wanted a little break but I turned her around over the bed, pushed my shorts and boxers down, my cock sprang out pointing straight at her ass. I teased her a little, rubbing my rock hard cock on the outside of her pussy. She was leaning back ready for me. Finally she begged for me. She wanted me inside her and who was I to deny her this, so I positioned myself just right and slowly slid the tip of it in. She gasped and started breathing heavy from anticipation. Once she realized I wasn't all the way in she pleaded with me to fuck her I can still remember her breathless voice begging, wanting, her pussy was so wet, some from my tongue and other from her arousal. After holding out I finally gave in to her demands and shoved my entire 8 inch length deep inside her pussy. She screamed so loud I clasp my hand over her mouth afraid someone would hear her because her bedroom window was slightly open. I slowly started thrusting in and out. She was tighter than I expected, still a little loose but felt really good. I picked up my speed a little in a nice steady rhythm then moving faster and faster, until her ass was smacking loudly against my groin. Her moans this time had become more high-pitched, muffled under my hand. I removed my hand from her mouth and listened to her frantic voice almost struggling to speak. "OHHH FUCK ME JAKE FUCK ME, FUCK ME" over and over she said. I love hearing women say my name, it always makes me cum immediately but I held on as long as I could I started trying to keep count of my strokes and visualized the numbers that sometimes helps me hold off. I smacked her ass so hard I felt the sting in my palm. I remember seeing the white in-print left around the red area it made. I told her to say my name again, she didn't so I gave her ass another good whack, Oh did she scream. She never expected it to be like this not with me, and to think she was hesitant at first I'm sure if she knew the amount of pleasure/pain I would give her, she would have ripped my clothes off instead. I smacked her ass one more time and commanded she say my name, she yelled it along with "IM CUMMING, IM CUMMING". she moaned to the beat of my pounding and came, letting out a powerful howl. While her body trembled, I could feel her pussy tighten on my dick. Once it seemed like she had calm down a bit, I pushed her up on the bed. She turned over on her back, still panting very heavily, her perfect tits rising up and down. I up crawled over her body, so that my cock was right in her face her eyes were closed still coming down from her orgasm, but as soon as they opened she wasted no time of attacking my cock. She grabbed it and tried taking it all in. She gagged a little bit but kept going, She kinda just let me do all the work though, I had one hand holding myself up against the headboard and the other on the back of her head, pumping her back and forward on my shaft. Soon I couldn't take it, I told her "I need to cum" She wanted me back inside her though so I stuck it back in her pussy and banged her out with force, she started out moaning fast then suddenly stop her mouth wide open holding her breath. I came inside her within the next few minutes She exhaled loudly in my ear as I collapsed on top of her. Needless to say we didn't make it to the gym that day. She asked for a rain check, I said sure. We met up and had sex in car for 3 more times. The 2nd, we had sex in the kitchen, I finally took her on that island table top and the 3rd was in the living room we had to cut it short though because Matt had called her right in the middle of it and said he was on his way back. He never found out though I think I almost told one of the guys when I was drunk one night. Sorry for the long story let me know if you want me them shorter next time. cougar_baitjake

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