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

[tampdown]

Starting tackle for our regional champ champ's anointed girlfriend. We made out but it was too dangerous. Oh the shame!
Pancaked by a letterman, squirting out, beneath the bleachers.

 

[DoodyMonster]

Most often would be my sister in law. Regular fantasies (imagined and written) of her for the 20 years I've been married to her older sister. May have a number of AI pics and short vids of her I enjoy too.

Also on the list- a cousin, an x-gf, occasional hot coworkers over the years, and some old high school "mean girl" crushes that I still watch on social media.

My reply would be similar to yours with sister in law always #1.
I'm completely clueless about AI so really curious about how you get AI pics and short vids of her.......sound like something that would be really "useful" to me

 

[Martin_M]

Ex mil, been years since I split with her daughter, but for some reason she’s very much a wank bank favourite with an ever changing parade of fantasies ...

 

[bumpinthenight2022]

Stepdaughter, legal teen but still in high school. I pull her worn panties out of the dirty laundry and inhale them while I stroke, sometimes will lick her dried juices out of the fabric. Some of the hardest orgasms I've had in a while ... Knee-buckling.

And the worst part is she kinda flirts. She keeps begging me to kiss her "injuries" (she bumped her knee on the door, for example). I want to so bad, but it feels like a trap.

 

[Italianstud59]

My best friends daughter. Had the hots for her since I met her at 17. Mom and I friends for 50 years

 

[RodDavison]

It’s not so much of a “shouldn’t” these days. But I’ll never forget the first time I masturbated thinking about my wife getting fucked by another man. She had recently cheated on me. I was furious at first. But soon I was actually starting to become aroused by her tryst. So when I had the house to myself, I found myself in a marathon masturbating session. It was an important moment in our marriage. I now knew 110% that I wanted my wife to have sex with other men. It took many years for it to happen but now we’re in a hotwife relationship we’re both enjoying.

Totally get that. I'm the same way. The best masturbation I had was watching her fuck another man.

 

[OneEyedSteve]

My 19 yo stepdaughter. She's a massive tease, even sends me photos from the changing rooms when she's clothes shopping, asking my "opinion" on thing from bikinis to tight dresses and tops.

 

[HotwifeBrooksideKC]

(Covers eyes) a cousin

Who was your first sexual crush?

 

[OneEyedSteve]

Stepdaughter, legal teen but still in high school. I pull her worn panties out of the dirty laundry and inhale them while I stroke, sometimes will lick her dried juices out of the fabric. Some of the hardest orgasms I've had in a while ... Knee-buckling.

And the worst part is she kinda flirts. She keeps begging me to kiss her "injuries" (she bumped her knee on the door, for example). I want to so bad, but it feels like a trap.

I do the same with my stepd. Her scent is intoxicating

 

[JohnA1971]

My big ass wife getting fucked by my mate who has a big cock

 

[phunkyphresh]

my son's girlfriend. she's cute in the girl-next-door sort of way. they are both gym rats, so she's always posting pics from the gym all hot and sweaty

 

[ClockworkFox]

Do they have to be alive? What I want to know is, does Marilyn Monroe count? You might think it's pretty normal, but I mean Marilyn Monroe in the present day. I'm pretty sweet on Elizabeth Taylor, too. And I'll be getting the hots for Claudia Cardinale in a few years for sure. And you thought YOU were a sick bastard, eh? Get a load of ME. Or a load off me, maybe.

 

[AngelicYasmeen]

Oh I have thought of various coworkers I've worked with. A few bosses. Most definitely to husbands and boyfriends of friends I know.

 

[stiv837]

My mother inlaw.