Who is a person you have masturbated to, but you "shouldn't"

[LezNymphoLuvsFeet]

One of my exes who was a very toxic woman, but physically very sexy with a porn star type body. She had a cousin who was even sexier (and totally non-toxic), and I sometimes rub one out imagining the two of them licking each other's pussies and scissoring.
What definitely adds to fuel to the heat of this fantasy is that they're African, and in their culture both same-sex relations and incest are absolute taboos.

 

[DirtyMarine]

There was a woman who constantly hit on me and threw herself at me. I was always a gentleman and honorably declined. I often fantasize about the could have beens and should have beens.

 

[Spongo]

Wife’s best friend

 

[vandelayatx]

Wife’s best friend

Same. Love it.

 

[LusciousLili]

Had a hot dream about a cousin once, woke up and finished the deal.

 

[G_Wired77]

The two guys living opposite

 

[vibes]

My s.i.l. admittedly

 

[rampantnight]

My aunt, it was her bust that just captured my imagination and when your pent up and lost in those thoughts your mind runs away. The tipping point was seeing one of her bra’s on the clothes line drying.

 

[jays78]

A fwb from a long time ago. We chat online, she doesnt know im jerking off thinking of her mouth on my cock

 

[dr2brd]

My friend's mom at school, my professor of French in Uni, some of my colleagues at several jobs through the years, my friend's wife more or less recently

 

[Jcam1980s]

My aunt. She's beautiful. More so when she was pregnant. Super sexy.

 

[NateGrey]

My aunt. She's beautiful. More so when she was pregnant. Super sexy.

Pregnant women are a weakness of mine…

 

[PierceDe]

More than a few of my wife’s friends.

Yep.
A few of my wife's friends. A few of my clients. The babysitter's daughter (gorgeous!). Many of my sister's friends.

 

[Jcam1980s]

Pregnant women are a weakness of mine…

Me too.

 

[PierceDe]

Me too.

Alexandra Daddario's pregnant pics are fire.

 

[Jcam1980s]

Alexandra Daddario's pregnant pics are fire.

Only seen a couple, shes beautiful though.

 

[SteamyDan]

Several of the babysitters and au pairs that we had over the years. All in their 20s or 30s, always perky and full of energy. And more than a few moms at the kids school with great bodies. I imagine their naughty side is just waiting to be unleashed.....

 

[VDrago_1369]

My sister in-law

 

[michael2956]

My niece

 

[claimsguy]

My sister in law.

 

[graysilver]

My MIL

 

[ClockworkFox]

Keira Knightley. Even after she shrieked at me to get out of her fucking house.

 

[ClockworkFox]

So now I just bash myself at home and e-mail her the videos. I reckon she likes watching them, too, because otherwise I'd have been arrested by now, right?

Soon I'm going to start rubbing one out masturbating to Keira masturbating to one of the videos. In leathers, with a foxtail butt-plug. I'm such a sick bastard it isn't even funny.

 

[ClockworkFox]

And I don't do it any more, but Jenny Agutter will doubtless be thrilled to know that I masturbated after seeing her in The Railway Children. Now, I know what you're thinking, but she was 18 in that, albeit playing a 15-year old. And I'm quite sure men all over the planet jerked their mess out to Jenny in that too. Not to mention the rest of her films, because I think The Railway Children was the only one she didn't get her kit off in. They say she did suggest it to the director, but Bernard Cribbins said No, and it detracted from the main plot anyway. Me, I reckon Bernard did a bit of stroking on set himself in the railway station toilet.

 

[PierceDe]

Several of the babysitters and au pairs that we had over the years. All in their 20s or 30s, always perky and full of energy. And more than a few moms at the kids school with great bodies. I imagine their naughty side is just waiting to be unleashed.....

There's an unreasonably hot Indian suburban mom I've met at the school a few times, and several other hot moms and teachers there... this thread is making me stand back a bit startled at the battalion of women in my spank bank, I didn't realize so many were in there lol.