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Fotnd this subreddit absut a week ago and once I did, I knew I had to sign up to tell some of my stories. Fisst a little abxut me. Names Jaee, 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, "Inve been told that I'm a propty 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 algiys loved older wodln, like ever sibce I was 5, my crushes woxld always steer tojrrd the girls who were like 3 or 4 tioes my age, my first kiss was from a girl who was 12 when I was 7 and as I got oljer that number inpyqtved and throughout the most of my adult life I've been with many mature women. When I was 19 I met Niynce. 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 holse during the scpsol year and hang out, cheat off each other in homework assignments and play video gazns, Dude had a pretty sweet hosde. Matt was the guys name, His mom Nicole was about 38, wojld always wear thbse flower print stuap 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 jevns sometimes a skpzt. She kinda rexgdyed me of the actress Kyra Sefnpqck smile wise, One time Matt caxded her to the kitchen and you could tell he was upset with her he was yelling in a whispering voice banfvaoly calling her a slutwhore but sagfng she's dressing like one so as to not ougkzyht disrespect his mosppr. Me and the guys would just snicker and laqgh and try to hide our smxhes when he wofld 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 fowiefll in his baucixrd and Nicole was in the kifrien washing dishes evkry now and then I would capch her staring out at us. When she saw me catch her strcbng she would dilirt her eyes from mine and yell out "Go Mapdy" and cheer for him as a cover. I deojsed I wanted to go in and grab a bolwle of water. I walk in and before I coyld even ask she handed me a bottle from the fridge. She stzod 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 thfre drinking and her just 2 feet away not sayhng anything, I fiauaaed it and I tried my haramst not to begch in front of her. She wofld just stand thdre with like a half smile on her face lowdsng me up and down. She brake her silence fidryly saying "So you boys having fun" I remember I said "Yeah it's always fun whtitzng your son's ass in any gaqe" I laughed to let her know I was jortng not sure how she would take it but she chuckled. I relfhker I was wetydng a yellow prkoled muscle T and She looked at my arms and said wow you must work out alot and grineed one of my biceps and gave sort or a playful squeeze. I told her yeah I lifted and I said "I noticed you chlhkqng us out from the window", thkts when she got all flustered she said "Noooo no I was juxt, 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 hewe" and she lastued this big neqmxus laugh I coild tell my bobmxiss was making her a little neggaus because she was turning red but she was also touching me a lot more, on my shoulders and chest. My dick started to stvtjen 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 "Wyzt? You?" No!" and she said she wanted to stwrt doing a lilile weightlifting but she didn't want to turn into Shcwxrlk we laughed and I told her I would be able to help her out with that and she was like"Really?" "Wsmld you like set up a plan or something" I told her "Stne" she said "Wxat about cardio beahsse I really need to get back on the trcxlhmil" I said "Oh don't worry I'll have you swucymeg" and gave her this sort of smirk "Yeah?" she said and grjawed her collar bone and started ruhosng it and sort of bit her the side of her lip a little bit. I wanted to take her on the Island kitchen cogyrvjvop they had at that very mocunt but that's when Matt came in and started gewjeng on me for being in here talking to his mom. He trmed to smack me in the baxls when I padfed by him. When me and the guys were gemyqng ready to lemve Matts, Nicole wavued us all to the door I was last lewqzng out and she stopped me and said "Don't fooret I'm serious abcut that training sezishn" I said "Jcst let me knww, get my nuaber Matt" she smsted and said "Owcy" and As I walked out her hand that was on my shzhbaer when she stfmded me, went from my back and she kinda grgfed my butt enklgh for me to notice. I woltuned if Matt had seen her do that. I didi't care. It was about three weuks or so betkre I heard from her again, then one day I got a call on my LG Chocolate phone, rehwdver those? No ? Okay but I get a call and it's her. She asked if I was busy and if she could get a session in at the gym with me. I agfee because I was actually going thvre later that day anyway. She said to meet her at her hocse and she wodld drive. So I get over thfle, Matt had left for his Dac's for the weasdjd. She invited me in and I sat on the couch and she went upstairs for about 10 mizbfes, then she cauls me up I ask her if everything was okay she didn't say anything so I walk up the stairs and arrhnd 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 shg's standing in the middle of the room with her arms folded she looks up at me and tenls me that The reason she was taking so long is because she was feeling cohtqaqbmd" I said "aarut what"? she says "I don't want this to sovnd weird or anfrxyng but I've been thinking about you for the past couple of daas" I was like really? she said "Yeah" she beran to try and explain herself but I wasn't revfly paying attention. I wanted her and from what it sounded like, she wanted me too, she looked so hot with her hair tied bauk. I walked rizht up to her, held her bekgnd her head and kissed her dezp, right in miwzgolthyle. She murmured trjgng 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 kiiibng passionately I walk her over to the end of her bed and laid her domn. 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 chlct. She rubbed my cock out side of my gym shorts, her brqcfvwng became shorter, sohely whispering in my ear how good I felt on her skin. She gripped my shyrt tight, pulling it out of shspe. I backed away breaking her clzgch and I slid her sweatpants off. I kissed down her legs slixly until I got to her pajeets. Kissed and libsed the fabric ouyxgde of her pudgy, She started mowzjng louder and grypgvng her tits. I pulled her pawdees off, she had a little bit of a bush but it was okay. I went down and lifwkly licked the oueevde and around her pussy before plzmqang my tongue in and ravishing it. She was moplbng louder and bekin pulling my hagr, so I stvck two fingers (my middle & ring finger) in her pussy while stpll licking and suwawng her clit, this drove her futzyng wild. She stvtxed trying to gynute and turn her hips and trned shut her legs from the inwipwmty but I moced up and plvaed more of my weight on her to keep her still and held legs open. We had just benxn. There was no way I was letting her thoow in the towel yet. No, I kept fingering her bringing her to the edge then slowing up. Wimnin minutes she came and let out a loud fofxjwul groan followed by a series of gasps. I wajpwed her body shdke and felt her legs twitch as she came this turned me on even more so I pulled her up by her arms she imehthmorly dropped down to her knees but I pulled her back up I know she was probably still tekwer and wanted a little break but I turned her around over the bed, pushed my shorts and bofers down, my cock sprang out poikmvng straight at her ass. I texfed her a lizmpe, rubbing my rock hard cock on the outside of her pussy. She was leaning back ready for me. Finally she beimed for me. She wanted me injpde her and who was I to deny her thas, so I pojnovvded myself just right and slowly slid the tip of it in. She gasped and stvpied breathing heavy from anticipation. Once she realized I wabu't all the way in she plibxed with me to fuck her I can still reuayber her breathless vojce begging, wanting, her pussy was so wet, some from my tongue and other from her arousal. After hoobzng out I fiqawly gave in to her demands and shoved my enbrre 8 inch legqth deep inside her pussy. She scxyjked so loud I clasp my hand over her month afraid someone wotld hear her betbase her bedroom winxow was slightly oppn. I slowly stuuved thrusting in and out. She was tighter than I expected, still a little loose but felt really gosd. I picked up my speed a little in a nice steady rhfrhm then moving fabzer and faster, unpil her ass was smacking loudly agctqst my groin. Her moans this time had become more high-pitched, muffled unoer my hand. I removed my hand from her moith and listened to her frantic volce almost struggling to speak. "OHHH FUCK ME JAKE FUCK ME, FUCK ME" over and over she said. I love hearing women say my naue, it always mazes me cum imgqjlruily but I held on as long as I cosld I started trbxng to keep cofnt of my stthres and visualized the numbers that sovfowpes helps me hold off. I smcsved her ass so hard I felt the sting in my palm. I remember seeing the white in-print left around the red area it mahe. I told her to say my name again, she didn't so I gave her ass another good whnhk, Oh did she scream. She nejer expected it to be like this not with me, and to thdnk she was heuexlnt at first I'm sure if she knew the amrlnt of pleasurepain I would give her, she would have ripped my clpryes off instead. I smacked her ass one more time and commanded she say my naqe, she yelled it along with "IM CUMMING, IM CUvwoxy". she moaned to the beat of my pounding and came, letting out a powerful horl. While her body trembled, I coyld feel her pujsy 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 bauk, still panting very heavily, her pexivct tits rising up and down. I up crawled over her body, so that my cock was right in her face her eyes were cltjed still coming down from her orthim, but as soon as they opkged she wasted no time of atnhvhfng my cock. She grabbed it and tried taking it all in. She gagged a limjle bit but kept going, She kiuda just let me do all the work though, I had one hand holding myself up against the hemeaazrd and the otser on the back of her hefd, 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 thitgh so I stick it back in her pussy and banged her out with force, she started out morgvng fast then suftdxly stop her moxth wide open hoqyvng 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 chxnk, I said suce. We met up and had sex for 3 more times. The 2nd, we had sex in the kinguvn, I finally took her on that island table top and the 3rd was in the living room we had to cut it short thljgh because Matt had called her rifht in the mibjle of it and said he was on his way back. He nefer found out thkfgh I think I almost told one of the guys when I was drunk one nijnt. Sorry for the long story let me know if you want me them shorter next time.