What’s the strangest thing you’ve masturbated to?


Jack’s Answer

Without a doubt, it was an unkempt hobo in an alley when I was twelve.  He offered me candy and toys if I put on a really good show.  I kept up my end of the bargain, but he didn’t.  Jill says that I shouldn’t have been taking candy from strangers, but he was only asking me to do something I was going to do anyway.  Despite being burned at such a young age, I never lost my positive outlook.

Okay, all joking aside.  I don’t know that it was strange per se, especially when compared to an unkempt hobo, but in December 2000 I was spending the weekend with family about an hour and a half from where I lived at the time.  As a constantly-horny male in his early twenties, I was accustomed to masturbating before bed.  If I was home, I would have watched porn on my computer, or even put in a VHS tape.  Remember those?  But I didn’t have access to any of that.

This was almost twelve years ago.  The concept of porn on demand was pretty much unheard of, certainly nothing like it is today.  I had no laptop loaded with digital porn or erotica I had written.  I had no smartphone.  There was no YouPorn, no Twitter.  Bringing porn along with you on a trip meant packing a few adult magazines in your suitcase.  I should have just used my imagination, but because there was a television in the guest room, I figured I’d see if I could find some visual stimulation.  I flipped through the channels in search of anything even slightly titillating:  Bikini chicks in some hip-hop video on MTV.  Lingerie models on the runway.  Even a semi-attractive local newscaster.

But I’m pretty sure that when the music stopped, so to speak, I was watching a commercial featuring no one attractive.

Jill’s Answer

Probably Fringe, the Fox television series about Fringe Division, a branch of the FBI that investigates paranormal occurrences.  I’ve been watching it since it began airing in 2008 (just a few days before we started blogging), mainly because Joshua Jackson is in it.  He’s hot.  He was hot on Dawson’s Creek, too.

I don’t think I ever masturbated while watching Dawson’s Creek.  I don’t know why not, but I do know that I’ve masturbated while watching Fringe.  I wish I could go into greater depth and talk about a specific episode or even a specific scene that inspired me to do it, but I can’t recall one.  I just know that when Jack and I were separated, I would set the DVR to record it and watch it late at night.  I’m usually horny late at night.  As I said earlier, Joshua Jackson is hot.  I hope I don’t have to draw you a diagram here.

In my own defense, I would usually pause the show and masturbate, then resume watching after I came.  Given the nature of the show I can’t imagine letting it play and being able to relax enough to actually get off.

What’s the weirdest porn you’ve ever watched?

Jack’s Answer

Claire James’ scene in a film called Extreme Penetrations 4.  Claire James is a porn star who was active in the early-to-mid 2000s.  I first came across her using the nom de porn Eva Malone on a now-defunct site called Eva Loves Cum.  The site was mostly POV videos of oral sex, and I assumed it was run by an actual couple.  When I found out that she was a pro, I sought out whatever I could find.  Eventually I came across this scene on a streaming website.

In the scene, Claire is out for a walk in the woods when she encounters something that I can only describe as a dildo monster.  Picture some manner of rubber-suited creature from a Japanese monster movie, albeit with numerous dildos protruding from its surface.  It’s the sort of thing one might see in a nightmare brought about by overindulging in deep-fried food and porn immediately before bed.  The creature attacks Claire, who does a fairly decent job pretending that she’s being assaulted by something that doesn’t look ridiculous.  Soon Claire gives into Dildo Monster’s advances and reciprocates.  She takes three dildos in her ass, followed by a load of a synthetic semen-like substance in her face.

This scene was equal parts strange and silly.  I didn’t masturbate to it; if I had it would have undoubtedly been the answer to the previous question.  I didn’t even find it arousing, despite the best efforts of all concerned.  It was, simply put, too weird for me, not brilliant enough to possibly be intentional comedy, nowhere near sufficiently amusing to function as accidental comedy, and too close to hentai for my own personal tastes.  All I was left with was legitimate curiosity:  Who would be turned on by something like this?

Jill’s Answer

A porn film from the late 1970s called Pizza Girls, also known as Hot & Saucy Pizza Girls.  In it, John Holmes is the owner of a pizzeria who employs a trio of delivery girls.  They skate around town in sexy but dated ’70s fashions, delivering more than just pizza, something that I found to be a clever spin on the pizza delivery boy cliché.  Meanwhile, a competing restaurant plots to shut down the pizzeria by raping the delivery girls.

Wait, what?  Yes, you read that right.  This movie includes a subplot concerning a serial rapist known as the Night Chicken.  The Night Chicken rapes a couple of the delivery girls (off camera), though the lighthearted, carefree tone of the movie never really wavers.  The girls don’t seem all that upset over having been sexually violated.  I’m not sure if it would have been worse if the film had been fun and comedic one minute, then terrifying and disturbing the next, but as it is it’s pretty unsettling to watch one of the delivery girls tell the others that she was raped as casually as one might tell of missing the bus, then pull up her top to reveal handfuls of chicken feathers.

I’ve never been a fan of story in porn.  It’s distracting, and I’d much rather cut right to the sex than waste time explaining why the pool boy is fucking the bored housewife.  Who needs a reason?  Pizza Girls goes a long way in demonstrating why a story is not only unnecessary, sometimes it’s not even desirable.  On the other hand, the sex scenes are pretty hot, and it’s always exciting to see John Holmes’ enormous member, if not his sunken cheeks, faraway stare, and his standard-issue porn star mustache.

What’s the last thing you masturbated to?

Jack’s Answer

A couple weeks ago, while clearing out one of my email accounts, I came across a story an old girlfriend wrote for me.  It was the fictitious account of a hot foursome that sadly never became fact.   It was all the more exciting to read because she wrote it at a time when she was just coming out of her shell sexually.  She and I would eventually engage in occasional monogamous group sex with another couple, and though she was never comfortable or secure enough to open up our relationship, non-monogamy remained a fantasy of hers as long as I knew her.  The story represented the first time she voiced such an interest.

Last night, while Jill slept, I read the story on my phone.  It was the first time in nearly a decade that I read it, much less masturbated to it.  The story was as hot as it ever was – hotter, even – and I had no trouble immersing myself in the action.

Jill’s Answer

An amateur porn clip featuring a British blonde being gangbanged by several guys.  I don’t know its origin, but nothing seems to be off-limits for the young star.  She sucks multiple cocks at once, she’s bent, prodded, and maneuvered into every conceivable position, DPed, then TPed (triple-penetrated, not covered in toilet paper), and finally takes multiple loads to the face, mouth, and breasts.  I didn’t put this clip on intentionally, but as I was looping an entire folder of porn clips, this is the one that happened to be playing when I came.  It was pretty hot though.

At the same time, I was also fantasizing about watching two online friends of ours having sex.  In my imaginataion, they started with oral sex.  Then they did doggy style with her bent over the bed as he fucked her with long, deep strokes of his hard, thick cock.  When he came, he pulled out, and she turned around to take his cum all over her tits.  Needless to say, I came hard.