Confess your strangest thought/fanatsy that has made you cum.

My fantasy is of fucking a man with a pussy. A female to male transgender who has under gone full top surgery and has been on hormone therapy long enough to have a full beard and extended clit. I want him to not have had any bottom surgery so that his pussy is still fully functional. I would also prefer him to be somewhat of a bear, nice and furry except for his pussy which I want shaved or waxed naked. That way we can enjoy oral sex with our bare genitals in 69 position before we fuck in missionary.

 

Many of my fantasies involve me being naked in a roomful of clothed people. After being put in that situation a few times I began to crave it.
The first time I was naked in front of three women they were kind with their comments, but that doesn't always happen. Girls in a group can become mean pretty fast.
My face always gets red despite the fact that I am really turned on, usually hard as a rock. Being limp is another level of humiliation.
Thinking of some of the times I've been naked for people always gets me off.

 

Plenty of seemingly strange fantasies I have masturbated to but by far the most are based on my SPH fetish. One such scenario features a work colleague whom I totally loathed. The sentiment was mutual. It didn't help ( at least from my side of the rivalry) that we crossed paths in a sports centre where we both had a membership through the company. He saw how tiny my penis is and I saw how much bigger he was.
I have fantasised often about having to watch and wank as he fucks girls I have had relationships with or fancied. I have even imagined me sucking his cock or him fucking me in front of them

 

A very tough tomboy bettered me in a wrestling match and wanked me while while her equally tomboyish friend pinned me down

 

In actual fact a tomboy named Michelle did better me in a wrestling match but only
pulled my pants down and laughed at my tiny penis.

 

It took a group of older girls but they stripped me, laughed and pointed them ran off with my clothes. I had to chase them down to retrieve my clothes so the first one had me buck naked running around the park till I caught her.

When having to wrestle my underwear off her, it was a full on match - except I was naked she was in short shorts and halter top. So, that’s when I did get excited and I did a little groping of my own till she handed them over.

 

Strangest thing? I dunno. If it gets me off, I don't think there's anything strange about it. Because if it drives me to climax, that means I've got something somewhere deep in my head that has a natural reaction to it of being extra turned on. So, inherently it's not accurate to call it "strange."

But for the sake of what I know you're really asking, I could say things that sound "strange" on paper might be comments my mother has made about how small my penis is and how quickly I cum. I get off to those sentiments no matter who's said them to me, but for obvious reasons, I'd imagine letting myself have an orgasm to the times it's coming from my mother would seem kinky to most people.

The reason I like hearing it from my mom as much as anyone else is because from her, I know she's just being honest and that she's not sugar coating what she thinks of it, but also that she's not exaggerating just to stick it to me either. I can trust it's not just honest but also not being said with any motive. There is also a part of it that turns me on because -- even though I'm not self-conscious about my size nor inability to last long when masturbating, it's easiest to enjoy hearing it from my mom because I have no reason for even the most subtle lingering impulse to feel like I need to impress her. And I can just enjoy the weirdness of being told that without being even the slightest bit self-conscious about it.

 

I can't give this post a like because of the harrowing subject matter but I also had to deal with a post rape situation when a female friend came to my flat after being raped. She lived in my building and was on her way home from a party. She excepted a ride from two guys who said they were headed in that direction. Not far from the flats is a small park. They made an excuse to pull up there saying one of them needed to pee. She said she could just walk home from there and got out of the car. However they grabbed her and dragged her into the deserted park and raped her. She did manage to flee so perhaps escaped any more violence or who knows what fate.
She wasn't hysterical when she came to my door more like in shock. Her clothing was very disheveled and obviously torn. She didn't want to report it to the police and took a while to convince her to do so. In the course of her description of the details like the guys themselves and of course the car she also confessed a very surprising and shocking detail. she didn't give details about the rape act itself but she said a great part of her trepidation about reporting it was to avoid any scrutiny and possible discomfort of interrogation and possible trial if they actually caught the guys. She most certainly didn't enjoy any of it but she actually had an orgasm while one of the guys fucked her. She said she was too shell shocked to struggle and thought she should just try to zone out as much as possible. She said it became like a kind of a blur - like it wasn't her body being abused.
I did manage to convince her that she needed to report it otherwise the bastards might do it again ( or maybe have gotten away with it before) She did have to suffer some q & a from the police and a rape consular but as far as I know they may never have bern apprehended. I haven't had any connect with her for a long time now and I have never passed on any details I was party to anyone who knew her nor given a name to anyone who didn't . I know that the rape of course predominantly would haunt her for the rest of her life but she was deeply troubled about the involuntary orgasm.

 

I don’t know if they qualify as strange
A couple of cousins
One of my friends mom
One aunt
One SIL
A teacher
Some of my sister’s friends
Coworkers
More …

 

I have imagined being bested in a fight by a guy in one of my work places who was the type who you know was probably bullied in school and is still very beta. After defeating me he pulls off my pants and wanks me in front of all the female employees until I cum. He also shows them how much bigger his cock is and makes me suck it.

 

I don't consider that strange at all. I would even
toss in a couple of nieces and a female social worker. I just never got up the nerve to act on the aunts, nieces, and cousins.