Last summer after my college graduation, a fraternity brother of mine, Justin, hooked me up with a gig in his dad’s construction company. Besides great money, the job came with free accommodations at their family lake house — which Justin and I had all to ourselves! It was really the perfect setup for two cash-strapped and sex-starved young guys. “This will be a summer of beer, pizza, and pussy,” Justin assured me. “Trust me, dude.”

On my days off, I would bike into town to grab lunch and people-watch on the docks, which is how I first saw the most magnificent MILF of my life. I was halfway through a second beer when she emerged from one of the high-end boutiques along the promenade. She stood about five-foot-six-inches, with long blonde hair, a tiny waist, and a set of tits that had to be at least a double-D cup. She was wearing a long light blue maxi dress, but no bra judging by the stiff nubs poking through the thin cotton. She had the figure of Jessica Rabbit and this sexy, sensual demeanor.

I must have looked like an idiot gaping at her, because the gorgeous MILF caught me staring, tilting up her oversized tortoise shell sunglasses. But instead of rolling her eyes or looking offended, she smiled — if only for a second. Then, she got into a little silver Mercedes convertible and sped off.

This wasn’t the first time I had found myself attracted to a slightly older woman. In my freshman year, I had hooked up with my Spanish professor who was in her late forties. Ever since that first MILF, I’ve come to realize that mature women possess this raw sexual heat that girls my own age just don’t have.

When I returned home, I told Justin all about “the MILF in the convertible,” and how I had to have her. “Dude, what are you going to do? Sit on the boardwalk and wait for her?” He had a point, but we were in a pretty small resort town, so I kept up the hope that I’d run into her again.

One week later, I got lucky. Pro-tip: if you want a MILF, check the grocery store, especially the wine aisle. The tiny grocery store was the busiest place in town outside of the boardwalk, and my gorgeous MILF happened to pull in just as I was coming out of the store.

She got out of the car, wearing a navy sheath dress and strappy heels that showed off her amazing legs.

I was carrying a case of beer and almost dropped it when she looked me dead-on.

“Hey there,” she said.

“Hi!” I anxiously shifted the weight of the beer so I could properly shake her hand.

“Didn’t I see you before?” she said with a smirk. “I never forget a face I like.”

I smiled. “You got me. Boardwalk, last week.”

“Uh huh,” she nodded, “right when I came into town.” She brushed her sun-kissed brunette locks out of her face. “I’m Dani.”

“Steve.”

She smirked. “Got enough beer there?”

“My, uh, roommate and I share.”

“Well that’s very nice.” Dani smirked. “So, you’re living here?”

“Yeah, for the summer,” I replied. “I go to school.”

“Yes, I figured as much.” Dani poked me in the chest, pressing her manicured finger square in the university logo on my T-shirt.

I felt myself blush. I couldn’t tell if she was just playing a cat-and-mouse game with me, or was really flirting? In retrospect, maybe it was both. “What about you?” I asked.

“I’m here to relax while my scumbag ex moves out of our loft.”

“Oh wow,” I paused. “I mean — I’m sorry to hear that.”

Dani smiled and shrugged. “I’m much better off.”

And then, I don’t know what came over me. “You want to come over for a beer?” I blurted out.

Dani giggled, which immediately made feel mortified. But then she touched my arm. “How’s about we do that beer at my place, hmm? I don’t have any roommates.”

“Oh yeah, sure.”

Then, the MILF opened up her snakeskin clutch and handed me a business card. “Call me,” she said with an encouraging wink, before heading into the store.

I stood there for a solid 60 seconds just staring at the card before tucking it in my shirt pocket. I didn’t want to seem too eager, so I waited until the next day to call.

Dani answered on the first ring. “Is this what you call a follow-up? Or do boys your age play hard to get?”

I sputtered and laughed. “Oh — well, I apologize for the delay — ”

“I’m only teasing you, Steve.”

“Right,” I took a breath and mustered  my confidence. “So, what about that drink? Are you free tonight?”

“I could be.”

“Great! Did you want to meet somewhere?”

“I’ll text you the directions to my place. Seven o’clock?”

“Perfect.” I felt my dick springing to life a little just in anticipation.

“I’ll see you then.” She hung up.

I spent the next few hours finishing up some yard work, but I mostly just paced around the property fantasizing about Danni naked and all the things I wanted to do to her. By the time I pulled up at her place, I had imagined the night in my head 200 times over. 

Dani met me at the door, wearing only a black silk kimono. We looked at each other, and a split second later, she was grabbing my collar and pulling me into her arms. I kicked the door shut behind me as we moved into the living room, a torrent of kisses and caresses all melding together.

But then, Dani pulled back and playfully shoved me back onto the couch. She stood before me with a devious grin, slowly untying her robe as she spoke.

“Look, I’ll be frank,” she said. “My ex was pretty boring in bed, and it’s also been awhile — a long while.”

Dani paused as if gauging my reaction and then continued. “And on both of those notes, I’m looking for a man who not only wants to fuck my brains out, but a man who is adventurous. I don’t want any drama, or strings — just crazy fucking.” She pursed her lips and looked at me. “Do you think you can handle all that?”

I nodded eagerly. “Yes, ma’am.” My dick strained against my jeans, as the situation grew more and more exciting.

“Alright then.” Dani gathered her hair to one side. “And there’s one other thing… ”

“Yes?”

She smiled and turned around, letting her robe drop to reveal first her toned back and then her juicy, heart-shaped bottom.

I inhaled sharply as I took in the view. Dani peered over her shoulder, locking eyes with me. “I want anal. And I want you to worship my ass.”

“Wow, uh, yes. Of course!” I sputtered, literally on the edge of my seat at that point.

Dani turned around and giggled. The gorgeous MILF before me had the most exquisite body I had ever seen in my life — and she was standing mere inches away. Now, I’m not saying babes around my own age aren’t hot, but Dani was like 500 percent more “woman,” and the way she carried herself sent every one of my senses tumbling into animalistic overdrive.

As my earlier assessment had confirmed, Dani had full, soft breasts to balance out the bountiful curves of her booty, and a tiny waist I could have slipped my hand around with one scoop. She kept her pussy hair trimmed in a neat triangle above her lips, which were just exposed enough thanks to a little thigh gap. She was like porn-star or centerfold material — and somehow she wanted me — I couldn’t believe this was happening.

I must’ve been sitting there with my mouth open, staring like a complete fool, because Dani smiled and tilted her head: “Is everything alright?”

I cleared my throat and swallowed. “Oh yes, it’s never been better,” I chuckled. “It’s just… wow. You’re gorgeous.”

“Come on, let’s get you upstairs.” She helped me up from the couch — and from there, my hands never stopped touching her.

We made out all the way across the living room, to the bottom of the stairs. And from there, I decided to pull out the stops and offered to carry her — she loved that. However, once we made it to the bed, Dani took charge.

She grabbed me by the belt buckle while I wiggled out of my shirt. “I’m dying to see what this bulge is all about.” Her free hand traced the outline of my shaft.

I inhaled sharply as I heard my zipper go down–and then registered the sensation of her warm breath on my body.

Dani gently tugged on my dick, pulling it out so I was at full salute. “And how is it again that you don’t have a girlfriend?” She smirked at me and gave my dick another teasing tug.

I chuckled, but then she licked her bottom lip and lowered her mouth to my dick. From there, I entered into a state of oral paradise. Dani definitely knew her way around a man’s body–she knew just how to touch me, when to suck, when to lick, when to release for a pause and when to resume with more gusto. Her plump lips and probing tongue took me to the brink and back, over and over.

I did my best to hold her beautiful hair back while she bobbed up and down, audibly slurping as she swallowed my shaft. I could feel the pre-come oozing out of me already. “Wait — wait.” I said.

“Hmm?” Dani looked up at me.

“Sit on my face.” I grinned. “You wanted me to worship that ass? I mean, this is great, but I can’t really do my part with your ass so far away.”

With that, she shifted positions so we were in a proper 69.

I dove into her pink folds tongue first. I have always prided myself on good oral skills. I get so turned on hearing a woman moan in pleasure anyway, but knowing that I’m the guy taking her there definitely makes it even better. I plucked and stroked her clit with my fingers, while my tongue teased her opening for a bit.

Then, with a few soft kisses and some slow, lazy licks, I turned my attention to her puckered asshole. Dani’s rosebud was a slightly darker pink than her pussy, but still alluring all the same.

Up until then, I’d really never had a girlfriend who wanted much to do with playing “back there” — and maybe Dani sensed my hesitation a bit, because she really started to moan once I began to trace my tongue in ever-narrowing circles around her asshole.

Dani released my cock from her mouth with a pop. “Oh fuck, Steven! Yes, eat my ass!” Her juicy booty wiggled enticingly on my face as I was engulfed in the musky smell of her arousal. I slid two of my fingers into her gushing pussy and darted my tongue right in the middle of her ass, teasing all the sensitive nerves around the opening.

Even if it weren’t for the fact that Dani was moaning so loudly, I could feel her pussy muscles clenching down on my hands as her pleasure kept on building.

Dani squealed and glanced back at me again. “Put a finger in my asshole.”

I did exactly as she asked — and added a third finger to her pussy for good measure. I finger-fucked Dani’s holes in unison, while navigating through the haze of my own pleasure. It wasn’t long though before she came. Dani arched her back and cried out, looking up at the ceiling, while I got an up-close view of her pussy and ass spasming in orgasmic delight.

I withdrew my fingers after — but there was no time to waste with this insatiable MILF. Dani rolled over and kissed me again.

“Now, I have a question for you.” She whispered in my ear.

“What would that be?” I asked, cupping her beautiful breasts.

“Have you fucked a woman’s ass before?”

I hesitated for a second but then smiled. “Actually, no. I’ve never been with a girl who wanted to try, so I guess you’ll be my first.”

Dani’s face lit up. “Oh boy — I love it!” She stroked my poor, tormented dick again. “You stay so nice and hard too, I think this is going to be amazing. But first, I need you to help get me ready.”

“Sure, whatever you want.” I definitely wasn’t about to argue.

Dani reached into her bedside drawer and pulled out a little stainless-steel plug. I lay there mesmerized as she reached for some lube and coated it. “Slide this up inside my ass?” Dani smirked and got on all fours.

I gently swirled the plug around, teasing her a bit with the insertion. But then, it actually surprised me the way her ass just opened up and ate the toy, leaving only the flared outer edge visible.

Dani moaned and stroked her clit. “Oh yeah, that’s what I’m talking about… ”

With the anal toy in place, I had her ride me reverse cowgirl, so I could take in the thrilling view of my dick impaling her pussy while the toy stayed deep inside her ass. If she wiggled or moved in certain ways, I could actually feel it too — which was wild.

As we fucked in deep unison, I spanked Dani’s ass and wiggled the anal toy around. I had to keep my brain distracted by something after all — because if I were to lay back and just give in, the sensations would have quickly made me come — and I was determined to last for Dani.

And this is definitely one of the pros of being with an experienced, mature woman: Dani was really intuitive about gauging my arousal level. She kept me at a nice but very hot plateau while riding my dick. However, it was only a matter of time before she wanted me inside her ass — after all — that was her “bottom line” all along.

She dismounted my dick, leaving it thoroughly coated in her juices. “You can take the toy out now.”

Naturally, I teased her. Dani moaned and rubbed her clit as I let the plug come a little ways out before slipping it back in. I twisted it, tugged it some more, and finally, after making sure her opening was as aroused and open as possible, I pulled out the plug.

“Hurry, Steven.” Dani moaned. “I want you to take me from behind.”

She didn’t have to ask twice. I reached into the drawer, slipped on a condom, and lubed up. “Is this good?” I asked.

Dani smiled. “Like a pro.”

My dick felt harder than concrete as I bore down against her tight anal ring, but then the miracle happened where that tight bud opened right up and practically inhaled me. Before I knew it, Dani’s ass had consumed my entire shaft, and my balls were slapping up against her pussy.

Dani exhaled. “Just relax and go slow.” Perhaps she said this for her own benefit as much as mine, but that’s exactly what I did. I started with shallower thrusts where I didn’t pull all the way out and then gradually worked us into a rhythm of nice deep anal drilling. Beads of sweat poured down my brow and chest as the sensations built.

Dani continued to moan loudly, intermittently rubbing herself. I squeezed her ass cheeks and reveled in both the view of her asshole stretching around my cock and the sheer sensation of it.

And when I finally couldn’t take it anymore, Dani was right there with me. I grabbed her by the hips and pulled her close as I exploded — I wanted to be as deep inside her ass as possible when I came. As I felt a torrent of hot come rocket out of my dick, Dani’s ass muscles trembled and her body shook. I held her tightly as she climaxed again drawing the heat of her orgasm through me as well. She reached back and clutched onto my hands, balanced around her waist, as we both fell onto the bed in an exhausted pile. She turned and ran her nose across my sweaty neck, nuzzling and kissing me before flopping onto her back in exhaustion. We fell into a spoon position and dozed off almost immediately.

A few hours later, we woke up and went back at it. She drove me home afterward and let me add that the look on Justin’s face when her convertible pulled into the driveway was absolutely priceless.

Our affair lasted until I went back to school in September — and to this day it’s some of the most unforgettable sex I have ever had. Indeed, you could say it was a long, hot summer — and a very tight and deep one with Dani.