I was bored so I re-downloaded (for the millionth time, probably) Tinder and started swiping around. Tinder is by far the worst dating app—in that the people on there generally suck—but occasionally it delivered a good fuck.
I swiped through for a few minutes—almost exclusively left swipes—when I saw Ashley, and I audibly laughed when I saw her profile. She was 49 years old—not that there’s anything wrong with that, just that it was genuinely funny that she was swiping on people half her age.
Now, I couldn’t be sure she was real, but if she was, she appeared to be pretty hot. Blonde and curvy, her pictures showed some delightful tits and an hourglass frame. Plus, her profile said she liked to work out, and a picture that showed her arms appeared to confirm it. I was willing to give it a chance, it was amusing at the very least. So I swiped right.
And I was very amused when, a few hours later, I matched with Ashley and had a message: Hey cutie ;)
We messaged back and forth about something banal like our days—by now, I had a pretty good sense that she was, in fact, real. I still had no idea why she was chatting with a 27-year-old, but I didn’t want to ruin it by asking.
Frustratingly, she wanted to grab a drink before we did anything else—I wasn’t here to date, I just wanted to fuck her. But I could play her little game if need be. We met at a quiet wine bar in the West Village near where we both lived, and I hoped that anyone seeing us would think she was my mom’s friend or my aunt or something.
I still wasn’t 100% sure she was real, but she came in and damn if she didn’t look exactly like her pictures. She wore a leather jacket, jeans, and boots, and when she took off the jacket, I could see those large breasts of hers through her sweater. She was undeniably quite hot, especially for a woman her age.
We sat down and ordered wine and started chatting. Then I noticed the ring on her hand. “Uhh, what’s that?” I didn’t want to be a part of some marital drama.
“Oh this?” She looked down at it casually. “Me and my husband have an … arrangement.”
“Oh cool,” I said, honestly relieved. We had a couple glasses of wine and talked—a bit awkwardly at times on my end, I will concede. I heard about her workouts, Equinox of course, and quite intense. She told me that she’d worked for many years in the music industry, and I got to expose just how young I was—in that she was hanging out with rock stars and rappers like around the time when I was born. She laughed easily at that—she was completely in control of the situation.
We went our separate ways that night, with a promise to see each other again when we were free—which came a week or so later. It was raining, so she invited me over to her apartment, a gorgeous, huge one-bedroom in the West Village. I plopped myself down on the couch and marveled at it—they must be pretty damn wealthy.
“I hope you don’t mind I dressed casual,” she noted. I did not—she wore only leggings and a sports bra, her massive tits filling it up nicely. I wondered if they were fake, but that was another question I wasn’t going to ask. Her tiny waist indicated maybe. Her stomach with its pierced belly button was delightfully flat for someone who’d had a couple of kids—complete with some jiggle and some stretch marks but close enough for it to be impressive. She looked amazing, and she definitely knew what she was doing.
She poured us glasses of wine and sat down next to me, describing that evening’s workout. I didn’t care in the slightest, but she for some reason really wanted me to know how intensely she worked out.
She looked at my arms, bulging through my rather tight t-shirt, “You look like you work out a lot too.”
“Yeah,” I nodded. It’s one of my favorite things, and not being able to go to the gym is truly one of the worst parts of 2020.
She smiled at me, “I like that.” Things were definitely starting to heat up, even if I was nervous for some reason. I was in women’s apartments all the time, but this was different.
When she got up to refill our glasses, I started looking around, and I saw a box of tapes. “What are those?” I asked.
She looked over, “Oh, that’s are just some really old stuff. Go ahead and look through them if you want.”
“No kidding,” I laughed. They were tapes. But holy shit—in there, she had like demo tapes for Nirvana and the Wu-Tang Clan, before they were big. “These have gotta be pretty valuable,” I noted.
“Oh, it’s whatever,” she shrugged it off, sitting back on the couch. Well, never mind. I thought it was pretty freaking cool.
I sat back down next to her, and she looked me in the eyes, leaned over, and kissed me. She tasted like red wine. Before I knew it, she was on top of me, those glorious tits in my face. I grasped them with both hands, squeezing them hard.
She pulled her sports bra over her head and there they were—perfectly round, sitting high on her chest, beautifully veiny, perky nipples on large areolas. I immediately put one of her nipples in my mouth, and she moaned loudly in response, her hands pulling me in deeper.
She started to grind herself against me, feeling my hard cock in my pants. I could see a small wet spot on her leggings where she was becoming aroused. I grabbed her ass and pulled her tight to me as our tongues danced against each other.
She was aggressive—with her kisses, with her hands—she knew what she wanted and she was going to get it. I sat up and took my shirt off, and then I just lay back and let her kiss my neck, her hands running over my shoulders, down my chest and abs, grabbing my cock through my pants.
Ashley undid my belt and the button of my jeans, and pulled my cock out—as stiff as it could be for this sexy MILF on her knees in front of me. She looked down at it, stroking it. “Good, I was hoping you’d be big.”
She’d clearly been a slut for decades, so I presumed she’d had bigger. But as long as I met her specifications, I was happy enough with that.
“Stay there,” she said, standing up to pull off her leggings as I stroked my cock, watching her. As she disappeared into the bedroom, I still couldn’t believe I was in this situation. There I was, naked in a rich MILF’s apartment—she was twice my age! And she had a daughter who was in her 20’s—like, in another life, I’d be fucking her. Instead, I was only minutes away from filling up her mom. I wondered if she knew about her mom’s activities.
Ashley returned with a bottle of lube, dropping back down to her knees in front of me, lubing up my cock, and picking it up again with both hands as I lay back on the couch. “Give me this fucking cock,” she said as she pushed her curly blonde hair back and licked the tip, looking straight at me.
She licked it all the way up, from base to tip—one, two, three times—before taking it in her mouth and immediately showing her aggressive nature. She stroked me with both hands as she sucked, her head bobbing up and down frantically, her massive tits bobbing with it, her impressively large wedding ring shining in the light. She didn’t play around, she didn’t tease, as she took me in her throat, impressively far down.
She came up for air, stroking me with both hands, “You like how far I can go, baby? You like how deep I can take you in my throat?”
“Fuck yes,” I moaned.
She squirted lube on her tits and more on my dick. “You wanna slide that big cock of yours between my big tits?” She squeezed them together to emphasize her best feature.
Of course I did. And she knew I did. So she did know how to tease. She flipped her hair back again, wrapping her tits around my erect cock, and starting to slide it up and down between them. I’d never felt this before, and the combination of the visual and the softness of her breasts—perhaps they were natural after all—was simply astounding.
She held them tightly together as she bounced her whole body up and down, all while she teased me with more dirty talk. “You like my tits, baby? I want to massage that dick. You like watching it disappear in my titties? But you better not cum before you can fuck my pussy with this big cock,” she moaned.
“You’re so fucking sexy,” I told her as she stopped and stood up, picking up a condom on the table and tossing it to me. I put it on as she stood over me, her pussy glistening and ready. She climbed on top of me, her hand guiding me into her—even the condom couldn’t mask the warmth and wetness of her pussy.
She gasped at feeling me, her ass moving slowly up and down, feeling every inch of me, moaning with every movement. My hands grasped her ass hard, guiding her up and down on me, her tits pressed into my chest—I could feel their weight.
I slapped her ass hard, and she yelped in surprise. “Do it again, baby,” she commanded, and I did. She bounced her ass faster, her hips doing the work, those tits jiggling in my face mesmerizingly.
“Yes, yes, yes, give it to me, fuck,” she moaned as I pumped in and out of her. “Shit baby, oh god, use that pussy to make yourself cum.” She was so dirty with her words, and unlike most people who try it, it really fucking worked. Now we were moving together sort of symphonically—my thrusts from below meeting her bouncing ass in perfect rhythm, her face contorted in pleasure.
She bounced and bounced, her ass slamming hard into my body, my cock deep inside her, the apartment filled with the sound of her moaning and our bodies slapping together. I think she was trying to use my cock to destroy her body, and I didn’t mind at all if I did.
When she came to a stop, needing a rest, I stood up, picking her up and holding her in my arms. I put her down on the couch on her back and climbed on top of her, resting my cock at the entrance of her pussy, as if waiting for an invitation inside. I sat back on my heels, spreading her legs as I slid myself inside her again—I wanted to see her tits bounce as my thrusts shook her body.
And we both wanted me to use her pussy to make myself cum. With the view I had, I could see all of my shaft disappear inside her, her lips split open by its girth. I wanted her to feel my strength as I pushed hard into her, my hands gripping her side, holding her up—her body shaking with each thrust. Those perfect tits of hers bounced uncontrollably, and she held onto them, trying and failing to control them.
“Fuck me good, baby,” she moaned. “Give me that big cock. Give me your cum.”
I was getting close, I could feel the cum welling in my balls, my abs straining from the effort I was expending.
“Oh fuck, oh fuck,” I moaned as I could feel it filling my cock, ready to shoot into her.
I collapsed down onto her, her breasts pressing into me, the muscles in my ass providing the final few pushes, her arms pulling me in. With a grunt, I came, my cock twitching as I shot cum deep into her.
“God damn,” I grunted when I could catch my breath, pulling myself off of her. I immediately had a post-orgasm feeling of guilt—what was I doing? I’d just fucked someone who could be my mom. I looked down and the vision of her slightly allayed that feeling—her breasts glistening with sweat, satisfaction on her face.
“That was great,” she said. “I’m glad you came over.”
“Yeah,” I said, putting my clothes on, feeling weird about it again. The sex had been good, but it was definitely a what am I doing with my life kind of moment—basically, questioning whether I should be as slutty as I was being.
I got out of there as soon as possible, and neither of us texted the other again. But it did help me win a contest of who is sluttier with a friend of mine a few months later, so at least I got that out of it.
Source: reddit.com/r/gonewildstories/comments/j8v76u/fucking_the_married_milf_mf_m27_f49
?? excellent story telling! ?