Sex Advice Interviews with MILFs

Sex Advice From MILFS - Shannon

Shannon, 23

Are MILFS better in bed?
This MILF is.

Last week, my new girlfriend had me over to her parents’ house for dinner. Her mom is gorgeous. Is it bad if I fantasize about her mom when we’re having sex?
Not bad. Just weird.

I had a crush on my best friend’s mom growing up. Now that I’m an adult, it’s a full blown infatuation. I’m a good looking guy and she’s single. Would it be wrong of me to ask her out?
If you’re any kind of “best” friend, you should probably talk to your friend about it first. Then you can find out how he feels about the situation.

My boyfriend shaves his armpits when the weather’s warm. He says it cools down his body temperature. Is it weird that his summer grooming practice freaks me out?
No. It’s weird for a guy to shave anything besides his face.

I was looking for toothpaste in my boyfriend’s toiletry bag and came across a prescription bottle for Viagra. He’s only thirty and I’m worried. What’s going on down there that he’s not telling me about? Should I confront him about it?
If you’re really worried, then yes. You were just looking for toothpaste; it’s not like you were purposefully snooping through his things. Approach the situation gently. Try not to smother his manhood and explain your concerns. And make sure to tell him how much he turns you on – that always makes a man feel better.

My boyfriend is still friends with his ex-girlfriend. Should it bother me that they get lunch a few times a month?
It’s not something I would be happy about – or allow my boyfriend to do. Obviously, there are still some feelings between them, or they wouldn’t be meeting up.

I want to try anal sex. But I’m afraid it will be gross. Is there a way to guarantee a clean first time?
No experience in this, um, field. Sorry.

I’m a woman and made out with a girl for the first time last week. We were drunk, but I wouldn’t mind doing it again sometime with her. I totally like guys, but am confused about this new desire. Am I a lesbian or just experimental?
I think only you can answer that question. There’s nothing wrong with exploring your feelings and desires. Just be smart and safe. Most importantly: don’t be a whore. No one likes a whore.

This girl I’m dating – a self-proclaimed feminist – recently confessed that she likes being choked while having sex. I care about her and want to make her happy, but I’m a little weirded out. Should I go through with it?
You shouldn’t do something you’re not comfortable with, but if you’re weirded out, just tell her. If she has a problem with your decision, then just choke some sense into her! I’m kidding... kind of. I mean, you know she’ll like it.

Comments ( 27 )

The first woman is so cool and the second one is so awful. I guess sometimes age really doesn't matter so much.

aa commented on Aug 20 10 at 12:58 am

Shannon! please take a gender studies class or gain some life experience or move out of Jersey... you sound like a barbie doll.

mg commented on Aug 20 10 at 2:23 am

There's a strikingly obvious difference in sexual maturity between a woman Shannon's age and one of Denise's age. Shannon seems unsure and unknowledgeable about a lot of things, whereas Denise (and Gabrielle) have dispensed some solid advice. MILFs FTW!

Salacity commented on Aug 20 10 at 6:15 am

Wow, Denise is so beautiful. I hope I look that hot when I'm 45.

MissHayden commented on Aug 20 10 at 8:42 am

Side note, lots of talk about ass this week... I like it. I'm very fond of that area now because of an awkward...weird...embarrassing... experience in my earlier days (ok, I'll admit it - some air got let out during the act and I was MORTIFIED). Even though I'm too scared to go back there, I've always wondered if other people have positive experiences, and how they makes those experiences happen...

MissHayden commented on Aug 20 10 at 8:49 am

I wish more people were like Denise.

eso commented on Aug 20 10 at 9:22 am

Shannon needs to shut up. "Don’t be a whore. No one likes a whore." What? I love whores. Plenty of people love whores. 'Whore' is a word for a woman who pursues what she wants, sexually. I think that's great. Whores are great. Date them, fuck them, fall in love with them, marry them. Shannon hasn't even taken it up the ass yet. Why is Hooksexup looking to her for advice?

Jack commented on Aug 20 10 at 9:35 am

I love Denise!

Bealzebub commented on Aug 20 10 at 9:54 am

Wow, like wine, improves with age.

mponyboy commented on Aug 20 10 at 10:04 am

Jack lmao, that was an awesome comment :o)

Ilikejack commented on Aug 20 10 at 10:12 am

I don't care how many kids a woman has, she isn't a MILF unless she's over 35.

Another Jack commented on Aug 20 10 at 10:19 am

I agree that Shannon is definately a bad example of a MILF, but maybe she's on here on purpose... To kind of prove a point that just because you're cute and you're a mom, doesn't exactly mean you're a MILF. True MILFs aren't 23, they're older, wiser, more mature and more experienced. Like the other two...

Kristaandthetots commented on Aug 20 10 at 10:27 am

Agreed - I think a true MILF has got to be over 35, with a kid who is reasonably grown up. If you have a kid in your teens or early 20s and are reasonably attractive, you're not automatically a MILF. What makes a MILF different than all of the other 35+ women with kids is that they're still fuckable - and not just "moms".

tdc commented on Aug 20 10 at 12:07 pm

Wow- what a bunch of unattractive milfs. Not exactly Stiffler's Mom types...

ES commented on Aug 20 10 at 1:09 pm

Anyone else think Stiffler's mom is dreadfully unattractive?

ML commented on Aug 20 10 at 1:51 pm

@ES: what are you talking about?? These women are beautiful in very unique ways - maybe not the cookie-cutter blonde bimbo type that gets you going... Especially Denise. I hope I look that MILFy when I'm pushing 50.

Corabelle commented on Aug 20 10 at 1:55 pm

I'm in love with Gabrielle. Too bad I'm older than she is.

Kel commented on Aug 20 10 at 3:03 pm

Lol Kel.

Harold commented on Aug 20 10 at 7:52 pm

gabrielle is just classy enough, and just enough older than i am, that i think it'd be interesting without being too weird. aces.

iameurrapanzy commented on Aug 20 10 at 7:56 pm

Denise, totally hot. Shannon, not so much. I agree, 23 with a baby does not a MILF make. I'm proud of my MILFiness, and I'm 42. Rockin' it. https://adulter-us.com

LambChop commented on Aug 20 10 at 8:44 pm

Hey Hooksexup!!!! Please note the difference between this and the Talk to Strangers article week. The best, most mature and insightful advice came from folks over 30 - please, please, please quit wasting our time with all those immature, egotistical 20 somethings - give us more *real* content like that from Denise and Gabrielle!!!!! Thank you!!!

Stephanie commented on Aug 21 10 at 12:51 am

Denise seems like a good candidate to keep around, and help improve the quality of writing in this place...

JD commented on Aug 21 10 at 1:47 pm

Ok, everyone so far seems to really like Denise, but her advice about both the Viagra and the "is choking feminist?" thing are both a bit off. Viagra should not be taken recreationally, period, and should not be condoned b/c he's doing it "for your benefit". And what one likes in the bedroom does not negate one's political and social beliefs. Egads.

AH commented on Aug 21 10 at 11:54 pm

Racquel Welch is my favorite GILF of all time.

bearman33 commented on Aug 22 10 at 3:38 am

If it's a prescription bottle, why assume it's "recreational". Unless you believe all ED drugs for all people are recreational...

JD commented on Aug 22 10 at 2:58 pm

Like Denise I'm 45 and a mother, and can vouch her advice is the best Shannon? A 23 year old? Are you kidding me Hooksexup?

jj commented on Aug 23 10 at 8:54 pm

Sudden realization: There is no male equivalent to MILFs, is there? jill In Bed With Married Women https://inbedwithmarriedwomen.blogspot.com

jill commented on Aug 24 10 at 12:18 am

Shannon, 23

Comments ( 27 )

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