The MILF Chronicles by Looty

So when I first started this current job, I was really bummed out because it was a small office and really didn't have any talent. But later on during that first day, I met a this hot chick and a milf. I immediately wanted to fuck both of them.

As time went by, through my quick wit and vile humor, the Milf and I grew closer and closer. Soon we were eating lunch together every day and emailing back and forth, sometimes a hundred times a day. The flirting really skyrocketed.

On the day of the Christmas party, which was at another one of our offices, she asked if I could drive her to and fro. I jumped at the chance. Knowing she was married with two kids, I really didn't think I had a shot but dreamed there was an outside chance of something happening that evening. No luck. Oh well.

So the hot chick is getting married and invites a bunch of us. I bail on the wedding but the Milf was desperate for a ride there. So again, dreaming she'd make a move, I offer to drive her. Slight problem, this gay black dude who wants me weasels his way in on the ride. I pick her up first and on the way to get him he keeps calling her to give her directions.

She picks up the phone and tells Gay Black to "stop calling me I'm sucking Looty's dick", in a joking fashion.

So throughout the whole wedding, the Milf is texting me nonstop.

"Wish you were here"
"You should come"
"Just come I want you here"

You get the idea.

So towards the end of the wedding she texts me that she wants to meet up afterwards. Done. I already know how this is ending. Don't we all?

So Gay Black slithers his way into the plans and comes out too. They're getting out of the wedding at 12:30 so I meet up with Pink and we go bowling and crush some pitchers while doing so. I get shitfaced while there.

So the Milf texts me and tells me where to meet them. I drive drunk (which I don't condone kids) and meet up with them. Pink and I are both smashed, borderline sloppy. So we hang at this bar 'til closing, drinking beers and yucking it up. After that, the Milf says I'm too drunk to drive and we sit in my car for an hour or so. She massages my neck while sitting behind me.

So this all went down Friday night. Saturday goes by with no contact from the Milf. Sunday rolls around and I get a text from her that afternoon:

"Do you remember kissing me?"

Wow, she must be joking about this cuz she wants it to happen. Nice.

Me: Haha, very funny
Milf: No seriously
Me: Uh huh
Milf: You don't remember?
Me: It didn't happen
Milf: Now I feel like an ass.
Me: Why?
Milf: Bc you don't remember our kiss
Me: Didn't happen
Milf: I knew you were drunk but didn't realize you were that drunk

Wait a minute...she does not sound like she's joking. I may have actually kissed her! I panic and quickly go into damage control mode to try to salvage this into hooking up with her.

Milf: You really don't remember?
Me: I do, I was jk
Milf: It was really gentle and nice
Me: Yup
Milf: You don't remember
Me: Yeah I do
Milf: Then where were your hands?
Me: On your hips
Milf: Wrong!

Is this seriously happening?

Me: Kidding, on your face
Milf: No! You don't remember! Your hands were on my shoulders
Milf: Where were mine?
Me: My ass
Milf: No!

Fuck me. Why the fuck would I guess ass?

Me: I'm really sorry. I was really bombed.
Milf: I feel like an ass. Is this the first time you've forgotten about kissing a girl?

Yeah...first time this week.

Me: No. Don't take it personally, I was smashed.
Milf: I'm really upset.
Me: Me too
Milf: Why are you upset?
Me: Bc that's something I want to remember
Milf: Really?
Me: Yeah, I'm really hoping I get another shot at it
Milf: I don't know

This continues the rest of Sunday night. I get into work on Monday and it carries on throughout the day. After some major damage control and buttering up, she shoots me this email:

I may have some time to spare after work tomorrow. Would you want to meet up?

Yes and yes!

Tuesday couldn't go any slower. We get out of work and meet a couple of blocks away from the office on this street that doesn't have any houses on part of it. She gets into my car. We start going at it. Big makeout sesh. She rub my penis on the outside of my pants.

A forty year old woman who is married and has two kids is rubbing my penis.

Love it.

I reach for her pants but she denies me. So after about a half hour of making out and some heavy petting, she tells me she has to go.

Hello, Wednesday. She shoots me an email asking if I wanted to meet up again after work. Done. Same deal. Just some making out and some fondling. Our session ends and I go home. I get a text later that evening.

Do you want to meet tonight? I'll have some time after my kickboxing class.

I meet up with the mommy and we go at it. Ten minutes in and she's unbuckling my belt. She's feasting on my cock like it was the Last Supper. She moves down to my balls and goes to town on them. But it doesn't stop there. She makes her way under my balls to my grundel and absolutely works it over. What a go-getter. First blow job and she's covering all angles. I blast and we part.

This continues for two weeks. We meet up and she blows me a minimum of two times, every time. Now I've fingerblasted her but she said she won't have sex in a car. Go figure.

So she emails me one day telling me that her family is going out of town for some hockey tournament that her kid is in. She suggests that we go out for drinks and then go back to her house. Given the fact that her husband was a big time hockey player that was supposed to go to the NHL before his father got ill and died, and he gave the sport up, I figure it'd be smart to take as little risk as possible. For all I know this dude could be an absolute monster.

So I book a hotel room.

We decide to meet at the hotel at 5:15. That gives me a half hour after work to check in, jerk off, take a shit and air out my sweaty socks. What the fuck was I thinking? A half hour? I'm a fucking dolt.

I get to the hotel at 5. That leaves me fifteen minutes to prep. I text her to see if we could change that to 5:30. She tells me she's two minutes away. Fuck. Didn't get to jerk off or shit. Walking around with two loaded weapons before a date isn't exactly something I prefer to do but I've gotta bite the bullet this time.

We go to a bar down the street and after her first rum and coke she's buzzed. After the second she's drunk. After the third she's making out with my neck as we sit at the bar. Check please. I stop off to get some beer before hitting the hotel.

We get back to the room. We're going at it, tearing each other's clothes off. We start to fuck. It's awesome. She's going buck wild. Her husband probably hasn't fucked her in ages. We're hitting a nice assortment of positions. Going strong. Straight plowing it.

Next thing you know, McGruff is taking a bite out of crime, and when I say crime I mean my fucking arm. This isn't a sexy nibble or soft love bite. This is great white shark chomping the shit out of a sea lion. I'm fighting back tears as I continue to fuck her. A sharp stabbing pain is pulsating at the spot of the bite, where my shoulder meets my bicep.

I am in so much pain my dick goes soft. Un-fucking-real. Couldn't keep it up. So she realizes and chalks it up to me being drunk. We fool around for a little and I throw another rubber on, thinking I'm ready to saddle back up. Get it in and start pumping. My arm is going numb. Lose the woody. This cannot be happening. And it certainly could not happen a third time. Could it? Fucking right it could. So humiliated at this point but I'm pretty sure she still thinks it's because I'm drunk.

She starts to suck my cock. My dick plays Lee Harvey Oswald to her JFK.

So we take a short break and before you know it I'm playing the pussy lips piano and she's back to sucking me off. Blast again.

So then we got into a fight. I really can't remember what it was over. She gets dressed and says she's leaving. She tells me she's leaving again. She keeps saying it but isn't doing it. She clearly does not want to leave and I'm calling her bluff. I tell her to do what she's gotta do. I'm basically Scott Boras and my penis is Mark Teixeira in these negotiations. After some drama and yelling at me she gets back into bed and is making out with me.

Now I'm determined to fuck her again, and finish.

I start fucking her. She's gets into it quickly and is going crazy again. So as I'm drilling away, wouldn't you know, fucking Hannibal Lector over here bites my hand as hard as she can. I bite my lip hard. I feel like slapping this broad. She reads the anger in my face.

Milf: "Oh I can see you're mad. I'm really sorry. I got caught up in the moment."
Me: "Nah, I'm not mad. I just can't really feel much of my left arm right now."

I tell her I have to go to the bathroom. I get in their to survey the scene and check out the battle scars. My shoulder is lightly bleeding. My hand, which feels like was slammed in a door, has a perfect mold of her teeth in it (which by the way, as I type this, THREE DAYS LATER, I still have the imprints of her fucking teeth in my hand).

I get back out there and she blows me.

We wake up the next morning and we fuck twice. In between, she shows me a text message her husband sent her last night:

Way to turn your phone off while both of your kids are way, God forbid something happen to them. Your son just wanted to say goodnight to you and you don't answer the phone. Guess it would be hard to do that with your mouth full. The sad part is I don't even fucking care anymore.

Now the weird part is that she said he's never acted that way before. I wonder if this buffoon is catching on to her coming home late three times a week to suck on my bratwurst. The best part was, by the second or third blow job of the night, she not only worked my grundel over but started tossing my salad. She continued to do so on each one after that point. There wasn't any tongue penetration like Fish Taco did but she did go to down on the outside and surrounding areas. It was a delight.

I look at the clock. We've been in bed for 16 straight hours, doing nothing but fucking and drinking. I really don't even remember how many times I jizzed but I'd say it was at least six, maybe closer to 7 or 8. My dick was so raw the next day that I could barely stand up straight. At one point, when we went to get lunch after all of this, she asked in amazement how many times we fucked. I couldn't give her an answer.