[M]y encounter with 2 milfs and an old fling over the course of 24 hours (all separate) PART 1 | 2016

I am going to make this a 3 part series, outlining the events of a 24 hour period I experienced this past summer in which I had encounters with 3 different women. I apologize for how long of a read this will be, but I like to give a lot of background and description

I'm 26 and I work oil and gas, I'd also like to think I'm a pretty good looking guy, your typical "all american" type, 6'3" 230 lbs, play football/hockey/baseball and did some modelling in my late teens but I'm also extremely introverted and so meeting people isn't my strongest suit. At the time of the soon to be described events I was about a month out of a 2 year relationship that ended very poorly, so I turned to internet dating just so that I could easily get some attention.

After registering for my profile I began searching for women in my area, I have a thing for older women so I filtered my search to only show women close to me that were older than 40. I began messaging the women who piqued my interest, one of whom was a 43 year old divorced mother of 1 that worked as an artist (she was a lead animator for a cartoon and had been commissioned by some pretty famous people). We had instant chemistry and quickly exchanged phone numbers so that we could begin texting more conveniently.

Over the next 2 weeks our conversations became far more frequent and much more open, I learned that her and her husband split because he refused to keep up with her physically and she developed an "I only live once so enjoy it" mentality because of it. She also expressed that she had been with a guy much younger than her before and that it ended badly (which also soured her on the idea of giving me a shot). Our conversations never fizzled though, and it was becoming more and more clear that we had a curiosity we were both eager to itch.

Late one night I was driving to Burger King (my cheat night is Whopper Wednesday) and my phone rings, I look down and notice it's Jenny (not her real name), I pick up and her immediate greeting is "I just wanted to know if your voice was as sexy as I imagined", I laughed and asked "well, do I pass?" as she lightly giggles and responds "big time". We wound up talking for 2 hours, during which time I mentioned that I had a hockey game the next night, she perked up and proclaims "Id love to come watch you!!!" We had never really discussed meeting, but now that it was on the table I definitely allowed myself to get a bit excited. We ultimately decided that she would come to my place to hang out first, if it wasn't working she could leave before my game and if it went well she said she would love to "hang out after my game and see how things go".

The next day goes by quickly, which was great considering how nervous I was. Finally, I get the text from her which read "on my way :)", it instantly made me hard and I continued doing the nervous run around my place to make sure everything was perfect. Finally around 7pm I hear a knock on the door, I open up the door and see a woman much more beautiful than I was expecting (we had exchanged photos but they did her absolutely no justice). She looked like a younger version of Susan Sarandon with brown hair. She was wearing a cute sun dress that revealed she was incredibly fit, she had amazing legs (she was about 5'9) and what looked like high B low C cup tits. We exchanged an awkward hug, she let out an "mmmm you smell nice" and I responded by complimenting her on how beautiful she looked. She came in, sat on the couch and we began talking comfortably as if we had been friends for years. During the course of our conversation she began holding my hand, which turned into her relaxing her head on me and then putting her legs across my lap, I was getting increasingly nervous and slowly getting hard, so I excused myself to start getting my hockey gear ready...

I came back out and said "so? what's the verdict?" she asked what I thought and I said "Id love it if you came to hockey so that I got to spend more time with you, what about you?" As I was saying this she walked up to me, kissed me and said "I'd love nothing more". While I was in the dressing room at hockey I got a text, I checked and noticed it was her, at first I thought she was texting to say she changed her mind and was leaving but nothing could have prepared me for what I was about to read. "Im kind of turned on by the idea of you getting kicked out of the game and coming to see you alone in the shower", she knew I was a bit of an agitator on the ice and frequently got tossed from games for fighting, this only made me want to get kicked out even more. I responded with "I'll see what I can do, if that doesn't work though I've got a great shower at home we can use ;)" (smooth, right? not).

I didn't get kicked out of the game and as usual I waited to get home and shower, I excused myself and told her to make herself at home while I cleaned up. While in the shower, I heard the door open and close, I popped my head out just in time to see her undressing. Without saying a word she grabbed me, pulled me out of the shower, propped herself up on the counter and pulled me close to kiss her. My mind is racing wildly at this point, I'm rock hard in a steamy bathroom, soaking wet and naked, making out with this beautiful 43 year old woman. She slowly starts exploring my body and made it quite obvious that she was not only going to take her time, but she was going to enjoy every minute of it.

She would only lightly graze my cock at times, but did so in a way that let me know she was deliberately ignoring it. Slowly she began to pay more attention to it until she was eventually softly and slowly jerking me off, until she decided she wanted to have a bit more fun. We switched spots, I leaned against the sink as she knelt down in front of me, slowly and passionately kissing and sucking around my belt line, hips, thighs, everywhere but my cock. Most of my extensive sexual history has been with young women who are eager to get the goods and get off, not this one, she knew what she was doing and that was making me want her more and more. By the time she finally pressed her lips to my cock i was sweating and moving anxiously just dying to feel the warmth and wetness of her mouth around me. As she had previously, she maintained a slow, passionate pace and continued to softly tease me. She would slowly build up to what I thought would be her going absolutely crazy on me, but just as I thought she would go nuts she would instead go 80-1 just to tease me.

By this point, I couldn't take anymore so I grabbed a fist full of her hair and slowly forced my cock down her throat, we did this for a minute or 2 slowly and passionately until the pace quickened to a light thrust, from that it turned into me full on fucking her face. Her hands found my ass and she grabbed my ass to force more of me into her mouth, as she released me and let out a slight gag she looked up, smiled and said "that's what I was waiting for!"

I stood her up, tore her clothes off faster than I thought was possible and sat her on the counter with her legs spread. I positioned myself between her legs and slowly kissed downward, stopping at her tits to lightly suck, nibble and blow on her nipples. There was no way I had the patience to tease her the way she teased me, I laughed and said "Im sorry, but I cant wait I just have to taste you", she smiled and started to say something but I didn't care to hear it and while she was talking I buried my face in her pussy, I'm assuming what she had to say wasn't very important either because her words were replaced with loud moans almost immediately. This woman tasted AMAZING, I wouldve tongue fucked her pussy all night if she let me. She came within about 3 minutes, afterwards she pushed me away and when I looked up at her confused she replied with "how are you so young but so good at that?" I laughed and she said "Ive never met a man who could use his mouth like that, wow" while she was still gasping and letting out frequent "wow"s she gets up, grabs my cock, looks me in the eyes and says "bedroom, now".

We get to the bedroom and she pushes me on my bed, climbs on top of me, looks me in the eyes and says "I had planned to tease you more and make you beg, but if your cock is half as good at its job as your tongue is then I need to fuck it, right now". She slowly traces my cock up and down her pussy, eyes closed and moaning, I can tell she is getting carried away with teasing herself so I wait for her to line me up perfectly while she teases herself, I grab her hips and quickly give her all of me. Her eyes go from sealed shut to wide open and her breathing stops as she yells out "holy fuck!" When I notice how good that was for her I immediately pull out and start tracing my cock up and down her pussy again. She looks at me puzzled and I smirked as I said "sorry, you were in the middle of teasing and I got distracted, I promise it won't happen again!" She looked at me and as serious as I'd ever seen her she says "it'd better fucking happen again, now fuck me!"

I lift her up a few inches above me so that shes almost hovering over me, this way I can fuck her from the bottom and thrust up into her with a lot of force, she loved it. It seemed her hands couldnt run through her hair or down her body fast enough, I was fucking her as hard and as fast as I could, my hands with a firm grip on her hips thrusting her down onto my cock to meet with the force of me thrusting up into her, it wasn't long before she was cumming again.

After she calmed down, she grabbed my hands and placed them on her tits as she said "I want you to play with these while I fuck you", who am I to say no? I dove head first into her request and began playing extremely rough with her tits, lightly slapping them, pinching her nipples and just groping them with a rough ferocity. She was grinding her hips hard and fucking me like I'd never been fucked before, I was getting close to cumming when she noticed, stopped, laid on her back and said "there's no way you're cumming until I know I'll hate walking tomorrow, now get over here and fuck this pussy until it hurts". I climbed in between her legs, slowly gave her the head of my cock and leaned down to kiss her as I began thrusting. I decided to tease her and only give her the head of my cock, but continued to thrust and tease her like I was going to give her all of it, this drove her CRAZY. After a few minutes of this I picked up the ferocity of my thrusts, my kissing became more passionate and every hand movement became more rough and deliberate. Her requests for all of me had now turned into full on screams, I decided to see just how badly she wanted me...

She kept asking for all of me, I leaned in and softly whispered to her "I really need to hear that you want it", this put her over the edge as her hands immediately grip my back, her nails into my skin and she squeezes her legs around my hips harder than I thought possible forcing me into her as she literally screams "I need you to fuck me, right fucking now". This was during the summer and so my window was open, Im sure anyone within a flew blocks heard it, but this only turned me on more. I began fucking her as hard as I could and the way she moved her hips, the way her tits bounced and the screams she was letting out were only working against my ability to last longer. It was when I realized how close I was that she grabs the back of my head, kissed me deeper than she had previously, looked me in the eyes and said "Im going to cum, I want you to cum at the same time", I began thrusting her, harder and harder, her screams picked up, her muscles started tightening and then she begins screaming "Im cumming, I'm cumming, im cumming!" This sent me over the edge and I blew what I still to this day consider one of the biggest loads I have ever had inside of her.

I collapsed beside her and we laid next to one another breathing heavily until she rolled over, smiled and said "Im looking forward to the rest of our night together". I laughed and asked "what do you mean?" She smirked at me and said "I still have tits, an ass, a stomache and a face that I need you to cover in cum, so when you're ready we're going again". We fucked about 6 more times that night and once the following morning, it was the last time I saw her as she was clearly also interested in dating but unfortunately I wasn't quite there yet...

Once again, I apologize for the length and if it kind of seems like I rambled at points. If there is interest in the next part of this story, I'd be more than happy to post it!