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I enjoyed writing about my 1st m/m experience yesterday, but here's something more recent with a MILF that is definitely one of the sexiest life experiences I've had the joy of taking part in. This story took place late last June. I work in a pretty typical office, a 9-5 job, but on this particular Friday evening last June I was working a bit late. We had a fairly large project that needed to be wrapped up, and it was almost 7pm by the time my workday ended. My friend Tom also works there, and after we finished up for the day we decided to head down the street to our regular pub to wind down. The pub isn't anything fancy, but is where those that enjoy a pint or 2 in my office go to get their fill. It has barstools, tables along the wall, and a fair sized open floor that is either filled with tables or cleared as a dance floor. There are also some dart boards along one wall, and a back patio. On a typical Friday evening it would be half full, mostly filled with locals that live or work nearby. On this particular night, though, it was packed and the place was hopping! Tom and I arrived around 7pm expecting it to be a typical evening, but it turned out to be anything but. On this particular night, the teachers from a local high school had descended on the pub for their annual year end/retirement party. There were teachers of all ages there, and friends/family of theirs as well. Everybody there to have a jolly good time. Tom was super pumped up about this, because he is known to be a bit of a skin hound and immediately started sizing up the hot young teachers in the crowd. Tom makes a fairly regular habit of picking up girls at bars so this wasn't too surprising to me. We hung out for a bit with some other people that we know, and a couple of hours and several drinks later Tom was over on the opened up dance floor working his finest moves on a sexy teacher girl. I'm not one for big crowds and didn't really feel like getting in the middle of all that, so I just hung out on a barstool and chatted with the bartenders, which was pretty much the usual type of night for me at this place. Since it was so busy, most of the barstools were taken, but there was an empty one next to me for a little while. Eventually one of the teacher ladies sat down in it to order another drink. She wasn't a young one, and I didn't really notice her much initially. Once she got her drink she stayed on her barstool and started making small talk with me and the bartender closest to us. The bartender was a little too busy to keep chatting with us, so the lady teacher and I got to talking amongst ourselves. It was pretty standard small talk, starting with talking about how busy it was, the weather, etc. But before too long we got to talking about ourselves. I learned her name was Diane and that she taught special needs kids at the high school. She had 3 kids (2 boys and a girl) that were all in their 20s, and left her ex-husband 10 years earlier. She wasn't one of the teachers celebrating retirement that night, but at 58 years old she was looking forward to it in coming years. I enjoyed talking with her, but hadn't really had any sexual thoughts about her at this point. I of course checked her out, though. She was pretty much your average 58 year old woman. A little on the short side, and her days of having a tight young body were behind her. She still looked nice, though. A little extra padding, and nice big tits. She had dark hair and a cute face that showed her age, but didn't look bad at all. All in all, if we walked by each other on the street I probably wouldn't have noticed her, but I enjoyed her company here. She wasn't dressed to pick up men or anything, she had a fairly modest pants and button up blouse type of outfit on with just a hint of cleavage showing (she probably always did though, big tits and all). Nothing about her or our current situation made me think anything sexual would happen, and everything was pretty casual. I wasn't there to pick someone up (but also not opposed to that), so everything about our current situation was very laid back, relaxed, with no pressure or expectations. Just 2 strangers with a 28 year age difference enjoying each other's conversation. We had a few drinks together at the bar over the next hour or so, and at one point Tom came back over giddy about his apparent success with a girl. He was a horndog ready to get it on with his chosen girl and he loved every second of it. After he left, Diane got a good laugh over it and said something about how the young ones have all the fun. I paid her a compliment about how I'm sure she made the guys go wild at that age, and still could if she wanted to. She blushed and said I was too cute, but she's afraid her days of having the Toms of the world fawning over her are well gone by. She also said that as an old fart she knew why she left the dance floor to sit at the bar, but why wasn't I out there picking up girls like Tom? I let her know I was just looking to unwind, wasn't a big crowds kind of guy, and was really enjoying hanging out with her actually. I did say that while I didn't come here to pick up women, if one happened to fall in my lap I wasn't gonna complain! When I said that, I noticed she kind of perked up, I noticed a little smile creep onto her face and her eyebrows raised, and even a quick glance at my lap. She said something about how a girl would be lucky to have me, and if she had much more to drink she might get too tipsy and end up falling into my lap! I definitely picked up on her becoming more forward with me, and I was just fine with that! I decided I'd start hitting on her more openly too, and told her I'd have no problem with her falling into my lap, but if she didn't watch out I'd lift her onto it before she even had a chance to fall! "Oh my, you are too cute!", something like that, is how she would reply to my cheesy flirtations. But, I could tell she was getting turned on, as was I. We playfully flirted a bit more, until our drinks emptied. I offered to buy her a drink, and she said ok but that she had to go to the washroom and asked if I could watch her purse and save her seat. I did, and bought us another round of drinks. When Diane returned, she thanked me for the drink and for watching her purse. She then opened up her purse, put it on her lap, reached into her pocket and pulled her hand out holding something in her fist. She looked at me to check if I was looking, then with her hand over her open purse she opened up her palm to reveal a pair of black panties being dropped into her purse. Wow! Hint received! She was wearing pants, not a skirt, but I was definitely thinking about sliding them off to see what was under there. I asked her if she wanted to get out of here after our drink, and she just smiled and took a big sip while looking at me with come fuck me eyes. Now, I love MILFs. MILF porn is one of my go-to genres. But, I had never been with a woman over 50 before. I had been with a few women in their early 40s, but a 58 year old woman was a whole new adventure for me. And while Diane wasn't what someone would traditionally think of as hot, I was so turned on by Diane and wanted her so bad. Maybe it was the alcohol, maybe it was the comfort level we achieved with our conversation, but at that moment she was the sexiest woman in the world to me. Tom could have all the young hot sparkplugs, but right then Diane was mine. I had to have her, and the way she was coming on to me, I was quite confident she wanted a piece of me too. So, as we had our last drink, we both stepped up our game. She put her hand on my thigh and rubbed it up toward my now very hard cock, but she didn't touch it, which was driving me crazy! I told her I was going to fuck her like she's never been fucked before, and how much I wanted her juicy thighs around my head while I make her moan. Yeah, at this point we we definitely both knew sex was gonna happen. It was so fucking hot to have each other in the palm of our hands. We finished our drink and left the bar. We decided to get a cab to her place, which was on the other side of the city, about a 15 minute cab ride away. We were all over each other as the cab pulled up, kissing and fondling, just going wild over each other. The cabbie joked how any fucking that happens in his cab he gets to join in on, and clearly got a kick out of us in our horny states. When he dropped us off at Diane's house he wished us a fun night with a wink and a laugh. Diane and I kissed and fondled our way up her driveway and into her front door. When the door closed behind us she told me how she never does this and how long its been since she had been with someone, and that she just couldn't believe this was happening. We took off our shoes and she grabbed my hand and walked me to her bedroom upstairs. I noticed her house was fairly modest, not a huge house or anything but she kept it together nicely. Once we got into her bedroom she kissed me and pushed hard up against me, as my stiff cock push into her squishy body. I grabbed her ass to push her in even harder and we made out like mad for a few minutes. We stopped kissing and she started to unbuckle my belt while I worked on unbuttoning her blouse. I helped her quickly get the blouse off and saw her large, succulent, sexy tits bursting out of her bra. She took no time to reach behind her and unhook the bra, freeing he girls for my viewing pleasure. I grabbed them in my hands and fondled her tits, while she unzipped my pants and started playing with my cock over my underwear. I stepped out of my pants and took of my underwear, exposing my fully at attention cock. She grabbed it and started playing with it while I lifted my shirt off over my head. Then, with my cock in her hand, she walked me over to her bed and beckoned at me to lay down on it, which I gladly did. Diane then climbed on top of me and started grinding me with her pants on while we made out some more. I played with her tits more while she was on me, and then she slowly started kissing me down me chest, to my stomach, to just above my cock. With one of the sexiest looks I have ever witnessed, she said "its time" and took my entire cock into her mouth. My god, she might not have been with a man for awhile, but she certainly hadn't lost any skills. This was a world class blowjob, folks. She worked EVERY part of my cock and balls, sucked and licked all the right places, deep throated, everything. She even knew how to bring me close to cumming, then bring me down, and back again over and over. It was pure ecstacy! I wasn't going to stop her from blowing me, that's for sure, and she kept at it for a long time, clearly enjoying every moment of it. After sucking my dick for an eternity, she laid down next to me and wriggled out of her pants, and I reached down to touch her slightly hairy (in a "I shave it sometimes but haven't in awhile" way)pussy. It was SOAKED, and she moaned at even the lightest touch. I rubbed and fingered it for awhile before I made my way down under and started running my tongue up and down her slit. I then focused my tongue on her clit while I fingered her dripping pussy some more. As I continued this, her chubby thighs clenched harder and harder around the side of my head until they were very tight and she was just writhing in pleasure. Even though my ears were covered by thigh, I could still very clearly hear her moaning and screaming loudly. A screamer! YES! The intensity continued to pick up until she just exploded in orgasm while I ate her. Wow, it was amazing. It was like the pressure she had built up in her pussy in the past while all just blew up in my face. Needless to say I loved it! After she finished cumming, I got up on my knees and lifted her spread legs up to my shoulders, while rubbing my absolutely throbbing cock on her pussy lips. I then slipped my cock in, and felt an incredible warm wetness that I can only describe as a sensation of pure pleasure. I started out fucking her hard and fast while she kept moaning loudly, and I got so close to cumming pretty quickly that I pulled out so I could recover and last longer. I lowered her legs so we were in the missionary position, and when I dipped my cock back in, I slowed my pace. At this point the sex could best be described as love making. We were both absolutely filthy horny for each other, but at that moment I was more in love with her than anybody else before. Its corny to say this, but it was magical. I had never felt pleasure this great before, and I wanted it to last. We slowly fucked for a good while, both of us moaning in true joy. As she started to look like she was getting ready to cum again, she told me she wanted to get on top. So she did, and started riding me in a glorious, passionate rhythm. After a few minutes of this her pussy exploded again, and I then flipped her onto her back again and furiously fucked her until I was about to explode. She said "cum in me" and not 2 seconds later it was my cock's turn to explode, and I continued thrusting into her as the cum flowed out of me into her pussy. After the sex, we cleaned up our juices and spooned (I was the big spoon!). She told me I was welcome to stay the night, and I took her up on her offer. We shared her bed and slept naked next to each other for the rest of the night, and I woke up in the morning when she was getting out of bed. She put on a robe and said she was going to put on coffee and make some eggs and toast if I was interested. I put on my underwear and followed her into her kitchen. As she was getting stuff out of the fridge I walked up behind her and wrapped my arms around her, kissing her neck. That was all it took for round 2 to begin! She took off her robe and I dropped my underwear to the floor, and we got to kissing and fondling. She brought us over to the couch and this time we got right to the sex, as she climbed on top of me and sank her pussy onto my cock. She rode me for awhile, every bit as awesomely as the night before, and then I got her to bend over the side of the couch so I Could enter her from behind. She went to the side of her couch, spread her legs and held open her plump ass cheeks to reveal her wet gaping pussy and a nice, tight, sexy looking ass hole. I put my dick into her pussy again, and took over holding open her cheeks so I could enjoy her ass while I fucked her. After some fucking, she wanted back on top of me, which I gladly obliged to. She quickly came, and said she wanted to suck me dry. She sat on the couch while I stood up in front of her, and she took my cock into her mouth for another all-world suck fest. This time she didn't mess around with bring me up and bringing me down, and when I was obviously about to come she took my cock out of her mouth and jacked it off until I shot a hot load of cum into her mouth and onto her face. A true breakfast of champions! After that we had real breakfast, and got back to chatting, basically picking up where we left off last night before things became sexy. She told me how she wasn't really looking for anything serious, but had so much fun with me that she wouldn't mind doing it again. I was more than okay with that, and was pretty pleased with myself for having gotten a true MILF fuck buddy! We hung out at her house for a few more hours that day before I went home in the early afternoon, and yes before I left we had round 3, which involved just pussy eating and cock sucking. We texted a bit in the following days, not making any solid plans but just stuff like how much we enjoyed our time together. The following weekend she came to my apartment and we had some more sexy fun. We've probably had sex 15-20 times since then, getting together a few times a month. Usually we make arrangements to meet up (mostly when she is horny she starts texting me), but one time I actually ran into her at the mall. She was there with 2 other people, who turned out to be her older sister and Diane's daughter. Her daughter is closer to my age and would definitely be fun to fuck...but no, nothing happened in that department. When I ran into Diane with her people, we had a small greeting and Diane introduced me as one of her former students, later telling me that she didn't want to bring up us as fuck partners to her family, which I understood. I do wonder if they thought I was a special needs student though, but she used to teach just regular high school classes so maybe not. She did text me soon after the encounter to meet up for drinks, which we did, which then led to sex. I last got a text for sex from Diane just last weekend, and we continue to carry on with our fun with semi-regularity. I mentioned her nice tight looking ass hole earlier, and sadly my cock hasn't had a piece of that yet. She's never had anal sex and while I've expressed interest, she hasn't let me put my dick in there yet. But, I did get a finger in there a few times recently, so things are looking up! We're both quite comfortable with each other now so if things keep progressing as they do I should get that ass at some point. Her pussy and mouth are more than satisfactory in the meantime The moral of the story is, fellas, be nice to the older ladies and they might just be REALLY nice to you! DrFuxtable