Alright, so this actually happened about a month ago, but I decided, “I guess I’ll post it.” As you can tell by the title, I had an encounter with a MILF, and let me tell ya: It. Was. Awesome. (And kinda weird, but mainly awesome.)
So, I’m a 19 year old dude who managed to land two of his stepsisters, a fact I still find rather hard to believe, and as such, I am much more confident after such encounters. Being in college and doing all that “adult” stuff has its perks in itself, like having a great group of friends who have houses to hang out at when we’re bored. Now, one of my friends, not a good friend, but good enough for us to say, “Sup bruh.” and be cool, was having a get together in which were going to play some Cards Against Humanity, watch some stupid movies, and have a good time until we either passed out or went home. The Gathering started at around 4:00PM, and then we were going to order a shitload of pizzas and wings and pig out at around 6:30. Now, because I am a guy who enjoys getting to places early so I don’t have to wait in a stupidly long line, I applied the same principle for this Gathering, and arrived 30 minutes early so I could park on the driveway. (Because parking on the street just generally seems to suck.) I locked my car and walked up to the front and door and knocked. Now, remember how I said we were 19-20? Well that technically means some of us still live with our parents, which isn’t a bad thing by any means, especially in this case, but let’s just say I wasn’t expecting his mom to answer the door. She had long and flowing strawberry blonde hair, and was wearing a very tight fitting athletic top that showed off her cleavage which had been clearly operated on (but it didn’t matter) and a pair of very lovely black yoga pants that showed off her nice ass and camel toe. I quickly scanned her and she let me into the house asking how I was and about college, so I made some small talk with her to pass the time. Turns out her husband was out of town for the week and she was just sitting around the house with nothing to do. Note: after about five minutes of her talking I sort of went into “autopilot” as the song “Stacy’s Mom” by the Fountains of Wayne began to play in my head, because, she definitely had it going on. Of course then she asked me something semi-interested and I snapped out of my daze, and said “Huh? Say again.” “Do you have a girlfriend coming over tonight? I know (let’s call this guy Johnny) Johnny does, and a few others mentioned it. Just curious.” She was leaning into the counter, as were in the kitchen, giving me a wonderful view down her top, and me regretting it not being a costume part so I could have shades on and act like the T-800 and “only state facts”. “No ma’am, I do not have a female acquaintance coming over. Nor was I aware we could, if we’re being honest.” She subtly raised an eyebrow at me, and nodded, her hair moving like a gentle breeze had swept into the room. I glanced at the clock and saw it was almost time for the others to come over, and excused myself to use the bathroom.
The Gathering started and sure enough some of the dudes had brought over their girlfriends, which I knew most of them so it was all cool, but me and the two guys who didn’t, sort of stuck to the “Currently Single Corner”, of the basement. The pizzas came and everyone sprinted up to get a slice, and I remained in the basement, mainly because SAW was on and wanted to continue watching, and because I hate waiting for food while looking at it, and because I wasn’t really hungry at the moment.
After watching the third movie in the series of progressively bad films, and playing some Cards Against Humanity for around 15 minutes before someone started complaining of how vulgar it was, one of the single guys went home. Soon after, the other single guy left, leaving me as the lone survivor in a pack full couples. After a few more minutes one of them got up and went into the bathroom together, and got busy. This prompted everyone else to excuse themselves to different parts of the house to do something similar leaving me to my own devices. Naturally, I made the executive decision to go and get food, as one does when they’re alone and somewhat horny. I went upstairs and found the remains of the pizza and some wings, and nuked them. While I was waiting Johnny’s mom came downstairs and asked where everyone was. Me, trying to be subtle as the somewhat clandestine doings of my friends, indicated they were… busy. This was promptly interrupted by a very load moan, coming from the basement. Johnny’s mom rolled her eyes and gave a heavy sigh and said, “You crazy kids.” When my pizza and wings were done, I pulled them out and began eating, and unfortunately for me, got a ton of pizza sauce on my shirt, which forced to exclaim, “I hate Pizza Hut.” Johnny’s mom gave a giggle at my situation, walked over to me, a paper towel in hand, and then the music started to play in my head. As she helped me clean myself up, I noticed she had taken off her wedding ring, and the fact that her breasts were much better up close. The music suddenly stopped, and she asked again if I had a girlfriend, to which I again said “No.” Then, she asked the big question: “Do you have a place to sleep tonight?” Now take in mind, she had her hand on my chest, and the other on my shoulder, because cleaning someone’s chest is apparently a lot more difficult than I previously thought. In my mind were two scenarios: me and her in bed, and me on a couch in the basement. On the off-chance she meant us together, I said, “Unfortunately no.” She gave my shoulder a squeeze and asked, “Would you like to stay with me?” Needless to say, I was somewhat taken aback, my thought process of, ‘Oh shit it worked.’ taking me more time to register than it should have. I casually asked, “I can stay here?” She looked into my eyes and repeated, “Yes. With me.” Of course, I responded with, “That would be lovely.” She then took one of my hands and began to lead me upstairs to her room.
When we got into her room, and she got very handsy, I asked her if it was okay, because consent is the most important part of any sort of sexual encounter, she was already breathing heavy, “My husband is out of town, and he’s sleeping with his coworker. Somehow I don’t think he or I cares. Do you?” I breathed a minor sigh of relief and responded by taking off my shirt and pulling her closer. She wrapped and arm around my neck and pulled me in for a kiss, and when our lips touched, she came back for more. Before I knew it, we were making out, and she was grabbing my now, very hard, cock. She took off her top and her breasts fell out, so round and firm, her nipples hard from the pleasure. She pulled my shorts down and pulled out my cock, her eyes growing wide and she gently caressed it with her hands. Before I knew it she was on her knees, her lips just touching the very tip, her tongue going in circles around the head, making me even harder. She began to blow me, deepthroating and using her hands with such expertise and experience it was hard not to cum right there in her mouth. She stood up and put her arms around my neck, embracing me in another kiss. (It was at this point I became aware that her lips were just around my dick, and I thought for just a second; “Yknow what? That’s kinda weird.” But then I remembered I was getting sex and said; “Eh, hygiene schmigene.”)
We walked over to the bed and she laid down, her yoga pants soaked through, as I pulled them down she moaned and began to finger herself. Then she grabbed my head and pushed me into her pussy. As my face was buried in her crotch, all wet and warm, I also realized that she had previously had a child and that I was literally eating out the pussy birthed the guy downstairs having sex with his girlfriend. I then thought, “Well, I guess I can brag about fucking his mom.” And stuck my tongue into her, causing her to push my head in even deeper. As I made out with her dripping vagina, she gyrated her hips and keep pushing, making me go deeper and deeper into her. She began to moan louder and louder, and she began to get wetter. She then let go of my head, and I came up, my face wet with her juice. I began to slowly kiss up her body, from her pussy up her stomach, getting to her firm tits and kissing and biting her nipples, causing her to squeal with pleasure, until we were face to face again. My cock was just above her clit, and I gently rubbed her pussy lips against the head, teasing both her and myself. She said, somewhat breathlessly, “Do it.”
I look at her again, for what must have been the the third time in a night full of disbeliefs, and said I didn’t bring a condom. “So? Just fuck me.” And again that song played in my head as I began to force my way into her. As my cock, hard and throbbing made it’s way into her pussy, I began well aware of a few things: 1) How surprisingly tight it was. And 2) How deep I could go. I leaned back and pulled her towards the edge of the bed, standing with legs on my shoulders and pounding her. Going so deep that her ass was hitting my thighs with a loud clap every time. I began to go faster and faster, her moans growing louder. I leaned over, putting her legs back and grabbed her tits, so firm and hard and kept fucking her. My god she was so tight. It felt amazing.
I pulled out, not ready to cum yet, and she ordered me to lay down on my back. I did and she mounted my cock, sliding herself down to almost all the way to the base, her ass hovering just above me and she began to bounce up and down. I slowly thrusted my hips and she worked her magic, until she finally just sat all the way down on my and leaned over, her hair and breasts in my face. I grabbed her ass as she rode me, her face and body the essence of pleasure and ecstasy. This was happening, I was fucking a hot MILF. Her moans got louder and louder until, I think, she came. (I honestly can’t tell because statistics say a majority of women fake it. But this felt very real.)
I began to feel like I was going to cum. I told her, and she got off my dick and immediately went to her knees, mouth open her beautiful eyes up at me as I stood over her with my cock in hand. She grabbed it with me and I let go, her mouth again wrapped around it and she sucked me off until I came. When I did, she opened her mouth for me and then swallowed all of my cum, before popping my dick back in her mouth to get every drop. She stood up and after it was done and gave me a long kiss. (Again, I then realized I had just ejaculated into this woman’s mouth a few seconds ago, and thought, “Does this count as one of those gay moments?”, but quickly dismissed the thought and embraced her.) Grabbing her ass and moving up her back until I was in her hair.
She pulled away, breathless, “That was amazing.” She said. Her eyes full of wonder, her nipples still hard and her body covered in sweat. “Well, I’m glad you thought so.” I responded. “Just don’t tell, yknow, your husband. Or your son. Or how about, I dunno, anyone?” She gave a little laugh and kissed me again. Making the ‘lips are sealed’ motion, she then climbed into bed and got under the sheets. I followed her, and she laid her head and hand on my chest as I put my arm around her, stroking her hair. She whispered to me, “Thank you.” I waited a second and responded, “No. Thank. You. That. Was. Awesome.” She playfully slapped my chest before closing her eyes. I did the same shortly after making sure I was still in bed with her. I was.
The morning came and she gave me some good head to send me off, and her number. She said the next time her husband was out of town she’d give me a call, and I thanked her again for her hospitality. As I got in my car, and drove off, I asked Siri to play me a song, and let me tell ya, I don’t care if I woke up the neighborhood with the sound of “Stacy’s Mom” at 7:00 AM. I had just fucked a MILF, and hopefully, I get to do it again.