How risky do you like to play?

Here is a thread that asked the question about places to put your suction cup dildo. The following is my reply:

Creative juices flowing upon reading this. Therefore:

Your back to the motel room door. The kind of motel with a big picture window next to the door and the door opens to the parking lot outside.

Bent over, hand on ankles, and the suction cup attached to the door. Opening and closing the door a few inches pushes and pulls the dildo. With the windows curtains strategically positioned, a curious person walking by could see the scene unfold as your partner slowly works the door. Eventually, the bystander could actually work the door from the outside for you, allowing your partner to participate in other activities.

Gotta be brave or crazy to pull this one off.
 
Risky play is something that I find little bits of included in stories or in people's occasional kink list, but I think maybe I find people that don't fully understand or play it safer than I do. Maybe I'm the weird one though. So, how risky do you like to play? There's so many levels of various risk of course. You have the public fun while trying not draw attention of strangers. I suppose the next level would be a professional environment, such as work, sports, school, etc. There are people you definitely wouldn't want to be caught with or by in those environments. I find it even riskier when there's a taboo aspect associated with it. Family or family friends, with people in the same house or even same room. The repercussions of getting caught seemingly higher.

So, what tier of risk do you like, if any? I'm just curious of course. I write on Literotica and have some stories I haven't published because the risk seems to be more than what people maybe like. I don't know. However, my rambling question is done. I look forward to hearing what people think!
I love taking the risks. I I understand the types of risks mentioned above and have indulged in all the tiers.
 
Nowadays, I’m mostly risk adverse and regret most of my wilder sexual exploits. In my 20’s, I was willing to tolerate a high degree of risk. Public sex, sex with strangers, sex with married women, sex with friends of my girlfriend, etc.

Spent most of my 30’s married to a wonderful woman who wasn’t particularly adventurous or a risk-taker in bed. Began to reevaluate my prior sexual history because it was something of an issue between us.

About a year after my wife passed away (I’m in early 40’s at this point), I slept with a married, very pregnant coworker. We were at a work conference and got together on the patio of the hotel we were staying in. We thought we were alone and didn’t realize otherwise until we were almost finished. No major repercussions - our audience was a bunch of strangers, fortunately - but it was a wakeup call for me. Nowadays, I am pretty solidly risk adverse when it comes to sex. I haven’t lost my sex drive - far from it - but, at my age, I’ll take dinner and conversation with a smart, sophisticated woman over any wild sexual shenanigans.
 
Nowadays, I’m mostly risk adverse and regret most of my wilder sexual exploits. In my 20’s, I was willing to tolerate a high degree of risk. Public sex, sex with strangers, sex with married women, sex with friends of my girlfriend, etc.

Spent most of my 30’s married to a wonderful woman who wasn’t particularly adventurous or a risk-taker in bed. Began to reevaluate my prior sexual history because it was something of an issue between us.

About a year after my wife passed away (I’m in early 40’s at this point), I slept with a married, very pregnant coworker. We were at a work conference and got together on the patio of the hotel we were staying in. We thought we were alone and didn’t realize otherwise until we were almost finished. No major repercussions - our audience was a bunch of strangers, fortunately - but it was a wakeup call for me. Nowadays, I am pretty solidly risk adverse when it comes to sex. I haven’t lost my sex drive - far from it - but, at my age, I’ll take dinner and conversation with a smart, sophisticated woman over any wild sexual shenanigans.
Excellent. I started a little late so I went very slutty for a while. I regretted lots of them. I just wanted to be loved.

It's a very bad idea to fuck around if you want to be loved. Doesn't matter if you're a man or woman. If you want a solid relationship and don't want to swing, hotwife, cuckold, cuckquean or hot husband, there's no point sleeping around.

I still haven't got my sluttiness out of my system, which I hate myself for, but I get much more turned on by an intelligent person who has a sex drive and is dominant too.
 
My first time having sex (and second, and third…) was with a married coworker whose much older husband (who also worked with us) wanted me to have sex with her. I didn’t at first until I knew her more, and was reassured that she wanted it, too. We were both in our early twenties. She didn’t want me to use a condom. I gave her all I had and sweated it out for a few weeks. I got lucky, and initially regretted the risk, but later was turned on by the whole thing.
 
Was mostly location-based risk for us. When we were younger, some outside locations, like hiking or balconies. Always when we visited someone and stayed over she would want to have sex. Some shared room risky times. But overall less as we got older.
 
I don't exactly have "partners" so for me, the tamer "risks" come mostly in the form of self-bondage up in the mountains behind my trailer or getting banged unprotected on the floor of the men's room by a bunch of dudes whose names I'll never know and whose faces I'll never see. I guess there's "risk" in "working" parties and retreats and stuff over long weekends, but I think some of the riskiest things I've ever done were obeying the commands of my online Master who loved compromising me by making me (not) wear or do certain things at work. I was a high school janitor at the time.
 
Risky play is something that I find little bits of included in stories or in people's occasional kink list, but I think maybe I find people that don't fully understand or play it safer than I do. Maybe I'm the weird one though. So, how risky do you like to play? There's so many levels of various risk of course. You have the public fun while trying not draw attention of strangers. I suppose the next level would be a professional environment, such as work, sports, school, etc. There are people you definitely wouldn't want to be caught with or by in those environments. I find it even riskier when there's a taboo aspect associated with it. Family or family friends, with people in the same house or even same room. The repercussions of getting caught seemingly higher.

So, what tier of risk do you like, if any? I'm just curious of course. I write on Literotica and have some stories I haven't published because the risk seems to be more than what people maybe like. I don't know. However, my rambling question is done. I look forward to hearing what people think!
For me it's outdoor sex.
 
I'm all for sex in public if it's not in people's faces. I'm not about trying to make anyone else uncomfortable. The risk of being caught is the thrill. Groping in public is fun too! I'd love to go skinny dipping. Sex on my porch swing, although my back yard faces an adjacent road.. unfortunately, my wife would never do any of this now... ☹️
 
I exposed my girlfriend on a beach with a boat being close to shore. I already had a boner, and got her to go to her knees to give me some licks while the guys on the boat were blowing the horn!
I've done the opposite. I've been naked and hard on my boat, with my lady, where we could be seen from shore. I have jerked off, and we have had sex. It's been a while, but is is fun to look back on.
 
Many years ago whilst working away on a contract I had an assignation with one of the girls in the office. Some weeks later she invited my wife and me to her house warming party. When we arrived she introduced us to her husband. The conversation was cordial, and when I asked her hubby what he did for a living he replied....POLICEMAN👮‍♂️👮‍♂️......I spent the rest of the night in 'imaginary' handcuffs.:sick::sick::sick:
 
Many years ago whilst working away on a contract I had an assignation with one of the girls in the office. Some weeks later she invited my wife and me to her house warming party. When we arrived she introduced us to her husband. The conversation was cordial, and when I asked her hubby what he did for a living he replied....POLICEMAN👮‍♂️👮‍♂️......I spent the rest of the night in 'imaginary' handcuffs.:sick::sick::sick:
 
Would getting it on at the drive-in count? It was even more fun when we were double dating. Or snorkeling in St. Andrews Bay off the Tyndell AFB golf course, I'd come up behind her, untie her bikini bottoms, use a little coconut suntanning oil and we'd get it on. We'd do the same on the back side of Shell Island sometimes.
 
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