My Girlfriend's MILF

1

I
first saw her the summer after my sophomore year. Mindy Carson and I had been dating for three months by then, and although Mindy was in great shape and a true nineteen-year-old stunner, once I saw her mother I couldn’t get the older Ms. Carson out of my mind.

She was sitting on the porch when I stopped by to pick up Mindy. I parked my truck out front in the street, and when I saw Ms. Carson I had to gather myself for a moment before I could trust myself to get out of the car without displaying my hard-on for everyone to see.

She wore yoga-pants and a loose-fitting blue top that hung down off one shoulder, showing off the strap of a black sports-bra. She sat on a white-painted wicker chair, her legs up on a footstool. A tall glass of iced-tea sat on the white wooden table by her, the beads of moisture rolling down the glass like pearls in the summer heat. She wore large sunglasses, but she looked stunning in them, her dark brown hair going well with her full lips that seemed naturally red like strawberries from the countryside.

She smiled at me as I walked towards the porch-steps and stopped at the bottom of the stairs. I could feel movement in my pants, heat rushing to my head, and I wondered what the hell was happening.

But I knew what was happening. Ever since I first looked down the neckline of my home-room teacher Ms. Braddock’s pink blouse back in middle-school, I’ve been obsessed with MILFs. Ms. Braddock didn’t have particularly large boobs, and her bra was so loose that when she bent down I could see her large, pointy nipples up close and personal. The nipples were dark pink and looked tough and sturdy, and I remember wanting to take them in my mouth and suckle on them like a hungry child. It was all I could do to concentrate on the rest of the class, and the moment I had a free period I rushed to the bathroom and jerked myself off in the stall, my cum flying out of me and hitting the back wall as I gasped, my eyes closed, my mind filled with the images of those hard, ready nipples.

Since then I discovered that women who’ve given birth and breast-fed develop a certain fibrous toughness to their nipples, a toughness that feels intoxicating when you pinch them, tastes sublime when you suck on them, cause them to sit straight up as if at attention when you cum all over them.

So now I stare at Ms. Carson’s chest for one long moment, praying to see the outline of a nipple, those same nipples that my girlfriend Mindy and her older sister must have suckled on so many years ago.

Ms. Carson was divorced, I knew. Mindy said she had had a few boyfriends here and there over the past few years, but no one serious. She was happy on her own, Mindy had told me once. She likes being single.

I can see why, I think as I walk up the porch stairs to say hello. Ms. Carson must be in her early forties, and although I can see lines on her forehead and face, small wrinkles around her eyes and mouth, there is no doubt this woman is as beautiful as ever.

My breathing quickens as she leans forward to get up off the chair. I try desperately to catch a glimpse of some cleavage, but she isn’t showing any. Now she is standing up, and she smiles and takes off her sunglasses, and I swear I hear birds singing, bees buzzing, and the angels of sex and fucking blowing their trumpets in my eardrums.

“Hey, you must be Richie,” she says as she extends her right hand. “I’m Beth Carson.”

“Hi,” I say, shaking her hand, my gaze taking in the smooth skin of her arm, which is gently tanned. Her fingers are long, with short, well-trimmed nails. There is some loose skin on the underside of her upper arm, but in general she is very toned for her age.

“Hi,” I say again, still shaking her hand, only now realizing I have a huge, goofy smile on my face, the kind of absent-minded smile that is a clear sign that most of my body’s blood is gathering in my dick and balls, making them swell up and beg to be taken care of. “I’m Richie.”

“Yes, I know,” Ms. Carson says, laughing a little now. “Mindy’s sent me a few pictures of the two of you. You make a real cute couple.” She pauses, looking down for a moment. “Can I have my hand back now?”

I laugh nervously and let go of her hand. “Oh, shit, yeah. Sorry, Ms. Carson.”

She moves her head back for a moment and gives me a fake-indignant look. “Ms. Carson? What is this, the 1950s? Call me Beth. We’re all adults here, aren’t we?”

“Right,” I say. “We’re all grown-ups.”

She smiles at me for a moment and then walks to the front door. I shamelessly stare at her ass in those black yoga-pants. It is larger than Mindy’s, and perhaps not as tight, but ohmygod is it turning me on like fuck right now. I see no signs of a panty-line, so either she is wearing a thong the size of dental floss or she isn’t wearing any underwear.

This last thought fills me with the kind of desire that makes it hard to breathe, and I inhale sharply as Beth Carson gently leans forward through the open screen door and calls out to Mindy, telling her to come on out.

I want to come on out too, I think now as I can almost smell Beth Carson’s pussy through the thin Spandex of those yoga-pants. I imagine myself dropping to my knees, pushing her up against the side of the house, her ass in my face. I’d rip those yoga-pants right down the seams, bury my face in her ass and pussy, licking and sucking until she’s wet and helpless. Then I’d stand up and reach around for those hard, MILF nipples, savoring their tightness, reveling in the way they harden beneath my fingers as I pinch and pull at them. Then—

“Oh, hey, Richie,” comes Mindy’s shrill, nineteen-year-old voice, and I am broken out of my daydream.

I am hot and annoyed, and I feel my boxers wet with precum. My hard-on disappears rapidly as Mindy comes to me and grabs my arm and leans in for a quick kiss.

I think I see Beth Carson flinch a bit as Mindy kisses me, but I tell myself it’s just my imagination and wishful thinking. No way is this happening. No way am I going to get to fuck my girlfriend’s mom, my girlfriend’s MILF.

2

A
nd I didn’t get to fuck her—not that summer at least. No, that summer was hot and heavy with Mindy—after all, we had only been together a few months, and when you’re nineteen all you want to do is fuck and cum. So Mindy and I did just that all summer. Blowjobs in my truck. Fucking outdoors in the woods. Handjobs in the last row of the movie theater. I even took her in the ass for the first time, down in my basement, on the fourth of July while everyone was outside watching the fireworks.

But I can’t deny that I much preferred not to have to look at Mindy in the face when we fucked the rest of that summer. I asked for more and more blowjobs and handjobs, and when we fucked it was almost always from behind. I had no issues eating her pussy, and I loved her round, tight little ass, but the truth is that when I was fucking Mindy, I was thinking about Beth Carson.

This was especially true when I would play with Mindy’s tits. Now, Mindy had reasonably large boobs, and they were smooth and perky. But her nipples were light pink, small, and soft, and although they would prick up a bit when I pinched them or ran my tongue over them, I could not help but feel a desperate longing for the hard, tough nipples of a MILF, of my girlfriend’s MILF.

So I spent that summer fucking Mindy senseless, but often with my eyes closed, in my mind imagining that Beth Carson was the one taking my cock in her mouth or jerking me off in the darkness or screaming as I rammed her hard from behind.

My fantasies got more elaborate and frequent, and as August rolled around I began to go over to Mindy’s place more and more often, sometimes without even telling Mindy, hoping I’d run into Beth Carson all alone, sitting on that porch in those tight yoga-pants. Perhaps she’d be asleep in the sun when I arrived, and I’d stand over her, watch her for a while. Maybe I’d slowly pull the neckline of her top out so I could look down at her breasts, those MILF breasts that were all I could think of. Perhaps she’d wake up but pretend to be asleep still, moaning slightly as if in a dream, all but inviting me to put my hands on her, to reach down through her top, through her bra, to where those nipples were waiting to be pinched so hard that they turn dark red with desire.

But it was all just fantasy. Although I got to know Beth Carson a little better, we barely had a conversation that was more than a few lines. Mindy never invited me over for dinner or anything, and so I never got to spend more than a few minutes with the object of my desire.

By the time we were back at college, I found my fantasies getting more and more desperate. It was no longer just any MILF—it had to be Beth Carson, my girlfriend’s MILF. I’d wake up in my dorm room bed, Mindy asleep beside me under the covers, and I’d carefully sneak out of bed and head to the bathroom where I could take care of my morning erection with thoughts of Beth. This was getting to be an obsession, I knew. It was beyond just juvenile fantasy. I needed to have this woman. I needed her nipples in my mouth, my hard young cock in her soft wet pussy.

And so I decided to take matters into my own hands, so to speak. This was going to happen, one way or another. We’re all adults, aren’t we? Yes, this was going to happen. I was going to fuck my girlfriend’s MILF, no matter what, no matter how.

And I couldn’t wait until Christmas or Spring Break, and certainly not until next summer. It needed to happen NOW!

3

I
thought about it for the rest of that week as I jerked myself off three or four times a day, often declining sex with Mindy because I was so fucked out, so obsessed with my MILF fantasy. Finally, on Thursday, I realized I would have my chance.

Mindy was in a sorority, and she and her sisters were going on a three-day retreat this coming weekend. I guess she had mentioned it earlier, but I had forgotten about it, so when she told me I was ecstatic. It seemed like a sign from those angels of depravity and sex, a coincidence that I had to take advantage of.

So I kissed Mindy and told her I would miss her, and when Friday rolled around and she got into that dark blue university-issued van and headed off to the mountains or the woods or wherever the fuck their little retreat was, I ran back to my room, hurtling up the stairs two-at-a-time, and stuffed some clothes and my laptop into a backpack.

Within a few minutes I was in my truck, music blaring, my cock twitching with anticipation as I wondered if I would last the entire three-hour drive without pulling out my dick and jerking off all over myself.

But I held on, because I wanted to save myself for Beth Carson. Although I still hadn’t figured out how the fuck I was going to pull it off, I knew that failure wasn’t an option. This was going to happen, no matter what.