Tag: MILF

Olive Wood – Embarrassing Mom Parts 1 & 2

PART 1:
Avast ye! Your mother has arrived to boys’ night dressed like a pirate and ready to set sail. Although you’re humiliated, you agree to let her stay if she’s willing to play “bar wench” for the evening and sneak you refreshments. After several rounds of grog and encouragement from your flabbergasted friends, the night takes an unexpected turn when Mommy begs you to lose your virginity to her.

Time to hoist your mainsail and head below deck! There’s booty to be had!

PART 2:
Your embarrassing mother is back and thinks she can tag along to a cosplay convention in a slutty burger costume she found at the back of her closet. Though you attempt to refuse her, she’s determined to prove to you and your friends that she’s cool mom material, and takes your cock while your bewildered buddies spectate.

Olive Wood – Bad Mommy

Last night you drank a bit too much with Mommy and the two of you did some very bad things. Seeing how distraught she is as she grapples with what she’s done, you decide that the best way to help ease her guilt is to talk her into imbibing a little more. A few sips won’t hurt, right?

Sloansmoans – Mother-in-law Cleans Up After You

For “Zach”: I’m your mother-in-law, and my husband and I have come over the day after your wife (my daughter) threw me a giant birthday bash. I want to help out and clean up while my husband goes and watches tv nearby. Before I start, I check to see if my husband is looking and then pull up my thong above my jeans to give you a sexy view as I clean. I get to work cleaning while you’re sitting and doing some work, but it’s hard for you to keep your eyes off me. I find tons of pairs of sexy womens’ panties littered around the room as I start cleaning. With each pair I find, I come close to you and whisper about what kind of girl might have been wearing that pair. For each pair, I imagine a description of the girl and the sexy fun you and her probably got up to during the party. Then I return to cleaning each time and make sure my husband still hasn’t noticed me flirting with you. Eventually, I get too turned on thinking about what you did with those girls, and I need to suck your cock until you blow a massive load all over my face and tits. As I’m sucking, I talk about how amazing your cock is and how you deserve all of these girls… enjoy me, xo

Olive Wood – Mommy Gets Your Sloppy Seconds

You’ve finally slept with your girlfriend for the first time, but somehow you crave more. With your girlfriend sound asIeep in your bed, you tiptoe into Mommy’s room and ask for sex. Although sIeeping with Mommy is nothing new, the two of you have never before tried sneaking around directly under a guest’s nose. Mommy is momentarily apprehensive, but it’s not long before the scent of young pussy on your cock sends her over the edge and she can’t help herself from begging you to fill her up.

Sydney Harwin – Mommys Uncontrollable Pregnant Urges

You catch your mom all dressed up, pretending she’s going out on a “night with the girls” but you know her secret. You checked her phone and she’s been messaging this stranger on a ‘meet up for sex’ app and she’s going to a hotel to hook up with him tonight for a one night stand! Your mom ends up admitting that yes, she’s arranged sex with this randomer, but only because she’s incredibly.. how embarrassing.. horny due to being in the second trimester of her pregnancy. It’s normal, apparently.. and also has nothing to do with you. Did your mom just basically admit that she’s got the.. horn?! Holy fuck, how sexy.. well your mom means a lot to you.. she’s your mom after all.. and you can’t.. WON’T allow her to meet this guy.. it’s too unsafe out there for a lone pregnant woman at night.. maybe.. no it’s stupid.. well.. maybe you could offer her something a little closer to home.. something to satisfy her “uncontrollable urges” right here.. right now.. with you.. her son.. it’s not wrong if you both agree.. and you can see how desperately horny.. wet.. begging for cock your mother is.. theres just no way she will say no.

Bettie Bondage – Draining Help from Mom

She told you not to go snowboarding with Andrew–he’s such a daredevil and you always let him goad you into doing things you’re not ready for. This time? No exception. You take a nasty fall and break both wrists, only a couple months into the spring semester, then you need surgery, taking you out for the whole season! This is a huge issue, your mom says, given the unpredictable recovery and what it will mean for your performance. I mean, you can kiss that Duke athletic scholarship goodbye…

Sydney Harwin – Taboo Bloodline

We had to run away.. nothing left for us in the family home after your dad discovered our secret affair and my taboo pregnancy.. but now, on the other side of the country.. living as runaways.. alone at last with my son.. I break it off. We can’t continue this madness any longer. For both of our sakes this ends today.. but my son temps me.. controls me.. loves me a little too much.. and I just can’t stay away for long.. don’t have the strength to say no.. I.. WANT.. HIM.. and now we can finally be together in complete privacy.. away from the judging world.. a new family at last.

Sydney Harwin – Keeping My Son Out Of Trouble

You come home tipsy after being kicked out of a girls house for behaving.. a little inappropriate towards her. Your Mom is mortified that you would treat a girl in such a disrespectful way, but equally worried that you’ll get yourself into some serious trouble if you carry on going down this path in life. You don’t wanna listen to your whiney Mom, so go to leave to go find another girl, but your Mom refuses to let you out of the door, terrified you’ll make a fool of yourself, or worse.. so she offers you something to keep you out of trouble on the streets.. something sinful.. forbidden.. something no Mom should even think about allowing her Son to do.. she offers you HERself to save you from YOURself.