From Madonna to Betty White: Mature Celebrities I Would Have Sex With

by: Gordon Lightfooted

Note: For the purposes of this post, I will consider “mature” to be over fifty. I may be leaning to the younger side, but, really, fifty is more than twice my age, means that there’s a near thirty year age gap, and makes most of them older than my parents. I feel like that’s a good starting point.

Also, I tend to hang out on the far end of the Kinsey scale. That said, I want to include women on this list, because sexy older women are a thing. So, you can acknowledge that I would not actually have sex with any of them. I know that. In fact, I’m not having sex with anyone at the moment, which is a conscious decision, so there’s really no point in throwing out the “but they’ve got ladyparts” defense.  Believe it or not, I’m not actually planning out any of these encounters, nor anticipating that actual sex will happen with any of them. I’m just saying, in some sort of fantasy world, I totally would.

1. Dennis Quaid

Pretty indisputable, right? He’s the epitome of the hot middle-aged guy. The wrinkles are there, but not excessively. The hair is only sort of greying. And he’s probably still got a six pack underneath those clothes, though it can’t hurt to check and make sure.

I remember my introduction to Quaid was that freaking Disney movie about baseball or something dumb like that. It was a mistake for my Jr. High school to show that movie with so many budding gays in the audience. I’m sure I’m not the only kid who spent the next month thinking of nothing else.  Dennis Quaid just sort of fits perfectly into that “your-friend’s-hot-dad” scenario, which I’ve always really loved. He seems a lot like the suburban father figure that you want to make horrible mistakes with that will possibly ruin his life.

And in fact, since I go to fancy celebrity school, everyone I know has class with his son (who bears a resemblance, I’m told) so perhaps there is a chance for me to negotiate that hook-up, and even if not, it’s only thirty years till the younger one’s blossomed into a beautiful older man.

Choice of Activity: I’ll throw thirteen-year-old me a bone here, and opt for locker room sex. Towels. Jockstraps. Shower. The whole nine. Have fun with that one, little buddy. And by the way, if you keep stroking that one chin hair you have, you’ll eventually pull it out. Caution.

2. Ira Glass

I had to google to make sure Ira was actually above fifty, and I have never been so happy to learn that someone is fifty-three.

I’ve always had a thing for soft-spoken nerd-boys. And while Ira may not be particularly soft-spoken, since he’s a radio host, he is indisputably a nerd. He works for NPR, for Christ’s sakes. Ira seems to be in that perfect middle-ground where he’s definitely nerdy, but still has a healthy sense of confidence and a good sense of humor. If any of you have listened to his recent audio sex tape with Terry Gross, you can back me up here.

Ira is living proof that the kid you wouldn’t talk to in middle school may very well grow up to be handsome, successful and out of your league.

Choice of activity: I have always wanted to have library sex with someone, and this seems like the ideal candidate. Hair-pulling. Tearing at each other’s clothes, all in the middle of thousands of books, late at night, praying security doesn’t find us. Hot.

3. Madonna

Yes, I told you there would be women. I did not tell you that, in some cases, I would be much gayer for having picked them than I would have been for choosing a man. But, she’s a legend, she’s pretty hot, and thinking about “Vogue” might be enough to help me get it up with a lady. Especially seeing the way she pushed the barriers of sexuality in the early 90’s when she was going through that Dita von Teese phase, I think sex with her would be a pleasurable experience, despite the presence of some elements I would perhaps prefer not to deal with.

Choice of Activity: Role-playing. I’m sure she’s got plenty of costumes, and as an aspiring director, she could probably enjoy coaching me. I want to recreate all of her videos from “Borderline” to the present, and end each one in a different lewd scenario. I’m really looking forward to “Like a Prayer”.

4. Kim Cattrall

Same thing I said about Madonna.

I would not need to grit my teeth to make it with Kim Cattrall for two reasons. The first is that she doesn’t bother me as a person, like Madonna does. There’s no fake British accent to contend with, nor a need to listen to her tripe about her film career.

Second, even though I wouldn’t be terribly into the act, I would want to hear her talk about it afterwards. This woman is a legend at talking about sex. She’s always hilarious when she does it. I’m sure she could come through with some excellent one-liners.

Choice of Activity: So I’d want to keep it new for her, to allow her to come up with some fresh material. I don’t feel like she’s the type to have ever been a Dom, and I feel like I could be a pretty good sub. Let’s go for it. See what you can come up with.

5. Walt Whitman

I can hear your protests already. Yes. Walt Whitman is dead. No, I am not saying I would have sex with a dead person. I like them older, but I have my limits. This one if conditional; if we could find a way to fix the whole “he’s dead” thing, without necessarily changing the “really old” thing, I’d be totally down. One, I love facial hair. Two, have you read the man’s work? Look up part 5 in “Song of Myself”. I’ll wait.

Yeah, that’s right. He wrote a poem about banging his soul. And it was totally hot.

Plus, look at that picture. The man had swagger.

Choice of Activity: Walt seems an ideal candidate for outdoor sex. I happen to know he has (had) a thing for armpits, so we could start with a little cuddling, nuzzling, et cetera alone in a field of grass, and then just let go.

6. Michelle Pfeiffer

This is perhaps the only woman that I would sincerely be into. You cannot deny it. She was a sexy woman when she was younger. She’s sexy now. I would even be willing to forget about Grease 2 to make this happen.

I mean, listen internet, she’s a stand up lady, and she still looks as fantastic as she did back in the day. Plus, she doesn’t look like she’s botox-ed her face to oblivion. Win. I don’t consider sleeping with women often, but when I do, it’s Michelle Pfeiffer

Activity of Choice: Are you kidding? She was a fantastic Catwoman. Bring out the leather, bring out the claws.

7.  Richard Gere

Duh. He’s dapper. He’s performed in musical theater. And I still haven’t seen American Gigolo, but the fact that he was in a movie with that title makes me a very happy person.

I mean, the white hair, the winning smile. And not that I’d be bringing him home to the folks, but if I ever needed to, he wouldn’t be a bad guy to do so with.

Activity of Choice: Even though it was never really confirmed, if he wanted to make a run to the pet store, I would indulge him in that.

8.  Betty White

I would not enjoy sleeping with Betty White at all. I mean, she’s a woman, And beyond the range of sexy old. One the skin starts to lose its elasticity and hang limply, I usually draw the line.

But, by God, if she wanted to have sex with me, I would do it. Because she’s a comedic legend. She was a Golden Girl. And I owe it to her.

Activity of Choice: Shut my eyes really tight and wait for her to finish.

9. George W. Bush

Why he was not one of the Sexiest Presidents? Look. He was awful as a leader of the free world. But he was a bit of a sex symbol. That flight suit picture with the huge bulge? All those vacation news stories that just happened to feature him with a cowboy hat? They knew what they were doing. The press played up the rugged tough guy image not only because it endeared him to misogynist men, but because it endeared him to middle-aged women.

And you know what? It worked for me too. I totally want to hate-fuck the guy. Like bad.

Activity of Choice: I want to ride on that horse with him, get good and sweaty, and then lie down somewhere and undress him down to his boots.

10.  Your Dad

Okay, look, I know this is uncomfortable for you. But your father is a very attractive man, and I feel like there’s really some chemistry there. Don’t look at me like that. I’m not gonna apologize to you for the people I’m attracted to. I’m sorry; I know it’s weird, but haven’t you ever been attracted to someone else’s parents? I mean, I’m not gonna do anything, I’m just saying, he’s quite handsome.

Choice of Activity: I’m thinking a quiet evening at home. We could make dinner in your kitchen. Snuggle up on your couch. Look at some of your old baby pictures.  Then, I was thinking of making out with him on your back porch and just taking it from there.

Gordon Lightfooted would rather not have his parents reading about his masturbatory fantasies. He’s real Gay, lives on the East Coast, and is currently engaged in the search for a Sugar Daddy. Serious inquiries please respond in the comment section.

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One response to “From Madonna to Betty White: Mature Celebrities I Would Have Sex With

  1. Gordon, you’re gross. W was not one of the sexiest presidents because he looks like a monkey. Cowboys are way hella sexy (speaking of, someone wanna cast Ewan McGregor in a Brokeback sequel that will actually make me cry?), but prep school babies who can barely sign their name putting on a cowboy hat and getting carted around a ranch to feel “rugged” are decidedly NOT. Also, big bulges are a big turn-off. Maybe you’ve got endless caverns somewhere in which to stick those giant members, but this lady’s parts have a sign outside that says “must be shorter than this to ride.” If you can’t wear a normal condom comfortably, you can just stay home, mmkay?

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