Risky Business

[Bigboobbabe]

What is the riskiest thing you have ever done with a stranger? When and where?

 

[sub2femdom]

What is the riskiest thing you have ever done with a stranger? When and where?

Good luck with that, you are going to have a hard time getting people to tell a public forum what is likely to be their deepest darkest dirtiest secret. Even anonymity has it's limits

 

[roseburgsteve]

What is the riskiest thing you have ever done with a stranger? When and where?

i was in Corvallis Oregon over night for a job. i was extremely horny, i went on to a hook up app and ended up talking to a guy. after about 40 minutes of talking he was in my motel room laying back on the bed i was sucking his cock then i crawled up on top of him and rode him till i came all over his belly and he came in my ass. he got up right afterwards got dressed and left.

 

[willi1796]

i was in Corvallis Oregon over night for a job. i was extremely horny, i went on to a hook up app and ended up talking to a guy. after about 40 minutes of talking he was in my motel room laying back on the bed i was sucking his cock then i crawled up on top of him and rode him till i came all over his belly and he came in my ass. he got up right afterwards got dressed and left.

You did not even lick it clean?

 

[roseburgsteve]

You did not even lick it clean?

he was gone to fast

 

[willi1796]

he was gone to fast

Guess what a shame for him.

 

[Bigboobbabe]

I was getting dressed in a first floor hotel room and heard the landscaping crew outside my window. I stood there in bra and panties until one noticed. He smiled and made a gesture of rubbing his cock.
I took off my bra and he watched me rub my tits. I sucked on my nipples and he asked my room number.
He came into my room, played with my tits and I stroked his big cock. He shot his cum on my tits aa I fingered myself to orgasm. He washed up and on his way out he thanked me and told me Jesus must have sent me because that was exactly what he needed.

 

[roseburgsteve]

I was getting dressed in a first floor hotel room and heard the landscaping crew outside my window. I stood there in bra and panties until one noticed. He smiled and made a gesture of rubbing his cock.
I took off my bra and he watched me rub my tits. I sucked on my nipples and he asked my room number.
He came into my room, played with my tits and I stroked his big cock. He shot his cum on my tits aa I fingered myself to orgasm. He washed up and on his way out he thanked me and told me Jesus must have sent me because that was exactly what he needed.

thats totally incredible i love things like that

 

[willi1796]

I was getting dressed in a first floor hotel room and heard the landscaping crew outside my window. I stood there in bra and panties until one noticed. He smiled and made a gesture of rubbing his cock.
I took off my bra and he watched me rub my tits. I sucked on my nipples and he asked my room number.
He came into my room, played with my tits and I stroked his big cock. He shot his cum on my tits aa I fingered myself to orgasm. He washed up and on his way out he thanked me and told me Jesus must have sent me because that was exactly what he needed.

I would have liked that too

 

[Bigboobbabe]

After I cleaned up and dressed, one of his buddies knocked on the window. I assume he wanted his chance.

 

[Londonguy69]

After I cleaned up and dressed, one of his buddies knocked on the window. I assume he wanted his chance.

Did he get his chance?

 

[Bigboobbabe]

After I cleaned up and dressed, one of his buddies knocked on the window. I assume he wanted his chance.

 

[cliteatingman]

After I cleaned up and dressed, one of his buddies knocked on the window. I assume he wanted his chance.

And...

 

[beatingoff]

The argument in my head is this ; do I hook up with a complete stranger not knowing if I'll be taking home some infection /std, finding a crazy stalker, maybe even someone who would be physically harmful. Do I hook up with someone I know, that I can bypass all that other bullshit, but have to deal with seeing them from time to time out in public /work place/etc.

I've done the acquaintance hook up, went well, we went our separate ways, still see her,I still have a thing for her. She told me it was rare for her to have an orgasm, I don't think I ever gave her one. Would love another chance, but as I said we've moved on.

 

[savmitch1038]

On a long road trip, pulled off the side of the road and had sex with my girlfriend! We were literally right off the road.

 

[Bigboobbabe]

The argument in my head is this ; do I hook up with a complete stranger not knowing if I'll be taking home some infection /std, finding a crazy stalker, maybe even someone who would be physically harmful. Do I hook up with someone I know, that I can bypass all that other bullshit, but have to deal with seeing them from time to time out in public /work place/etc.

I've done the acquaintance hook up, went well, we went our separate ways, still see her,I still have a thing for her. She told me it was rare for her to have an orgasm, I don't think I ever gave her one. Would love another chance, but as I said we've moved on.

It's a tough decision. I am picky about who I lick and suck. Not as picky with stroking or them stroking to fun on my tits.
It's all about how risky or not risky transmission of disease would be.

 

[hardbiker82]

Had sex with a married woman in the bedroom right next to where her husband was sleeping. I didn't want to -- but she wanted it and so I played along.

 

[jackbird]

late 70's

Use to suck cock at a rest area on rt 2 in mass in the open. It was the late 70's gotten caught a few times to ended up sucking them to.

 

[carln3346]

Blowjobs in a public park. It was 'safe', but the whole activity of connecting with someone, getting the message across as to what we wanted, then actually doing it was still risky and exciting as hell

 

[sluttyjulia]

What is the riskiest thing you have ever done with a stranger? When and where?

I once fucked a guy I met in a coffee shop in the stairwell of a mall.

 

[Justfantasies]

When I was about 19 I visited a friend and his very cute mom came on to me big time. I ended up fucking her on her marital bed. Both my friend and his dad were in the house. Not sure whether they ever found out.

What made it doubly risky was that we used no protection whatsoever

 

[Followmenow6969_2]

What is the riskiest thing you have ever done with a stranger? When and where?

Out with my GF's and started dancing with some woman she started grabbing my bouncing tits so I slid my hand under her skirt and fingered her to orgasm right there on the floor and my GF's cheered me on lol

 

[EktachromeJP]

What is the riskiest thing you have ever done with a stranger? When and where?

i met her at her office and she sucked me off in the interview rooms just off the lobby. she just couldn't wait to have my cock in her mouth and my cum in her stomach.

 

[Texastuffbbc]

In college. I visited a university about 20 minutes away. Went to see A young lady I liked. Her roommate was there for the weekend. We strolled around campus and ended up on the steps of the main building. I sat 3 steps up and she sat between my legs. She unzipped me and sucked my dick in broad daylight. It was about 1 in the afternoon. What a rush and the thought of being caught. Hedges on both sides and we could see in front. Never even considered there might have been cameras. lol

 

[roseburgsteve]

the woman i play with every weekend last august went a bar to play a trivia game afterwards my girlfriend and her girlfriend stopped by because her friend wanted to meet me.it was 11 pm at night. my house is on a corner lot and she parked on the side street. while my wife was in bed asleep i went out to meet them both. we got to talking and fooling around. both the women where touching me through my pajama bottoms and making out. next thing i know my girlfriend bent down and sucked my cock. then her friend did. a car turned the corner and her friend got a bit nervous. but once the car was gone i bent my girlfriend over the hood of the car and fucked her and came in her. her friend was shocked and excited and kinda stood by us just in case another car started to turn. i was so turned on it didnt take but a few minutes for me to cum but it felt good. all the while my wife in the house sleeping and the chance of being caught on the street by passing cars.