What's the biggest sexual related risk you've ever taken?

[southern_gal]

Originally Posted by desiresmore

Oh I believe you can do it! Once you try a little bit and gain more courage - you might be surprised at what you'd be up for. You just need a few successes under your belt.

Practicing online doesn't hurt either. I'm sure many of us would love to give you ideas or help out!

That is the sole reason I joined recently. I have been here reading for literally years but decided to start posting and trying to peel back a few layers to get to the person that exists in my fantasies.

[desiresmore]

Originally Posted by southern_gal

That is the sole reason I joined recently. I have been here reading for literally years but decided to start posting and trying to peel back a few layers to get to the person that exists in my fantasies.

Fantastic! I look forward to getting to know more about you and seeing you grow. Feel free to PM me anytime!

[southern_gal]

Originally Posted by desiresmore

Fantastic! I look forward to getting to know more about you and seeing you grow. Feel free to PM me anytime!

Dear, a lady never sends the first pm. See even now I cannot release my inner tramp. Whatever am I gonna do?

[monkeyman057]

Lots of unprotected sex in my twenties. I got tested regularly though - I wasn't so much concerned about catching something myself, but was mortified of the possibility of transmitting something to someone else.

Sex in public - done it. I don't really see it as all that risky but it seems to be popular in this thread so I'll put it on my list.

I've had a blowjob while driving, thanks to my awesome wife. I don't see that as all that risky either, but w/e.

I guess it really depends on how you want to define the word 'risky'. What exactly does that mean?

[soflabbwlvr]

Originally Posted by southern_gal

I have not really taken even one risk in my life sexually. I have never had sex without the man using a condom before I was married. Nothing ever in public and nothing really risque. That is downright sad and simply must change. I am working on that.

I wouldn't call it "sad." Rather, I would say that you have an opportunity to broaden your horizons.

[southern_gal]

Originally Posted by soflabbwlvr

I wouldn't call it "sad." Rather, I would say that you have an opportunity to broaden your horizons.

Might as well broaden my horizons. So far all I have broadened is my butt.

[soflabbwlvr]

Originally Posted by southern_gal

Might as well broaden my horizons. So far all I have broadened is my butt.

Perhaps both could benefit from a little expanding.

[2981notrohrm]

Bareback sex with a guy in a bathhouse while the wife was out of town.

[TwilightJ48]

Had sex with my friends husband at work

[desiresmore]

Originally Posted by TwilightJ48

Had sex with my friends husband at work

That sounds like its worth a story post! Would love to hear the details on that one!

[NoMoreNoMore]

Hmm, okay, like someone else said, blowjob while driving. My first wife liked to do that. We also did it in her parent's den.

Had a relationship with a coworker. We used to meet down in the basement. She'd start up the check writing machine and we would go to it. I met her at her house a couple of times and we would go downstairs and enjoy each others company. Meanwhile, her husband was upstairs watching his shows. He no longer had any desire for sex so she turned to me. She had moved on to another job and I ended up somewhere else, but when layoffs started, she got me a job at her new place. We then did it in the elevator. Love in an elevator.....

[Somehowyou]

I have had a few rubbers break while sleeping with a few young female escorts. Once the rubber broke while having anal intercourse with a hot termas girl at a famous Rio terma (brothel).

A few years back I called a Latina TS after reading her ad on the Atlanta Craig's List. I went over to her nice suburban apartment and we hit it off. After talking for awhile we went to her bedroom and made love. It was torrid. I put her in the cowgirl position. After rubbing cocks with her, she went down on me and then we flipped over with me on top. I returned the favor and then spread her legs. I moved up to kiss her while humping in the general area of her ass. She grabbed some lube and put it in her ass. My cock went in without any effort or guidance at all. It was not even my intention. Before I knew it we were fucking in the missionary position bareback. I came buckets and then immediately regretted it. I pulled it out and she begged me to finger her ass while she masturbated to completion. I went into her bathroom and put antibacterial hand soap on my cock and it burned. Then I jumped in the shower. I told her we shouldn't have done that. She felt bad and said "It's just that you were so clean and so nice...."

We both got tested and we wrote each other after the fact. She wrote me and her letter said "Good news! I am still not HIV positive!" Since then she has left the game. She was completely passable and had a day job. I don't think escorting was the right job for her. I swore I would never have unprotected sex with anyone after that and I have been able to keep that promise so far.

[juani123]

Some of my more riskier actions would be sex in a Ferris wheel. she was wearing a skirt so it was easy. Back in high school me and my gf used to do it in the janitors room.

[LadyVer]

Sex with a stranger I met on a roadtrip in a hotel bar .Many moons ago.

[Aqualover69]

Sex in Ibiza with a girl from Greenwich Village. Too much red wine and sex without protection. Things she said after the fact about being tested in the past freaked me out ruined my holiday and I spent two days in bed worrying and feeling sick to my stomach.

Always used protection for one night stands after that.

That's what I consider risky. Everything else is just pure excitement and adrenaline rush.

Sex totally butt naked next to a tourist attraction at Uni at night with people walking past may be risky to some, I found it a rush more than risky.

[Arianthe]

Wild, kinky sex in a disabled toilet across the hall from police licensing headquarters. With a uniformed officer.

Also, sex in the stairwell of a public library, on multiple occasions.

[1Browneyedguy]

Fucking in a semi public area.....
Several times in a National Park... NOT in a tent either !

Several times in a natural hot spring. A few times kind of in the open... on a trail, etc

However I have also had sex with a previous GF in a nearby park while " picknicking " and once or twice in a car while parked in a mall parking lot, on a upper level.

[peebudy]

jerking off and pissing on myself in a Lit chat with my wife sleeping upstairs!

[timelegend]

When I served in the US Army in South Vietnam I visited the local brothel. When you first walk in the door you enter a parlor room decorated in French tapestries and furniture. The girls all sit around and you pick the one you want. She leads you down a narrow hull way with rooms down both sides with only a screen of beads for a door. I was led down to the last room on the right. I leaned my M16 against the wall and undressed all she had to do was slip off her dress and lay on the bed. The room was about 5x5'. I had just finished shooting a load when I heard screams and gunshots. I grabbed my M16 taking the safety off and stepped out of the room and there stood 2 freakin Viet Cong going room to room shooting at will. I emptied my M16 taking both down, after my knees and hands stop shaking I realized they had missed me by inches the wall behind me was full of holes. I still remember that sexual encounter as if it just happened yesterday.

[RjThoughts]

Having sex with a woman I met at a wedding reception in a small room that had been set aside for the bridal party, while her husband and daughter were outside the door talking.

[RawHumor]

Originally Posted by timelegend

When I served in the US Army in South Vietnam I visited the local brothel. When you first walk in the door you enter a parlor room decorated in French tapestries and furniture. The girls all sit around and you pick the one you want. She leads you down a narrow hull way with rooms down both sides with only a screen of beads for a door. I was led down to the last room on the right. I leaned my M16 against the wall and undressed all she had to do was slip off her dress and lay on the bed. The room was about 5x5'. I had just finished shooting a load when I heard screams and gunshots. I grabbed my M16 taking the safety off and stepped out of the room and there stood 2 freakin Viet Cong going room to room shooting at will. I emptied my M16 taking both down, after my knees and hands stop shaking I realized they had missed me by inches the wall behind me was full of holes. I still remember that sexual encounter as if it just happened yesterday.

I'd say you win! Wow.

[Somehowyou]

Enclosed is summary of this thread. The first one is my favorite. Samantha, Would you like to relive that moment? we could recreate that scene and you could dress like a schoolgirl in pigtails and I would give you a lolly! My we are a bunch of freaks arent we?

Originally Posted by samanthaswitch

I was at a friends house when i was staying over a few days. I was up late (I get insomnia some times) looking for a snack when I heard moaning from the living room. I snuck over to find her dad watching a porno on the tv. It was a hot one of two girls going at it and I was still wide awake so I tried to hide myself so I could watch but my own noises gave me away. He turned red and asked me why I was still up and I explained. We just sort of stared at each other for a minute and I leaned in an gave him a kiss (i'd known their family for years and always thought he was cute). I started rubbing him through his pants and he told me I should go back to bed but i could feel him responding so I kept kissing and whispered he didn't have to watch a movie to get off. It took some persuading but I wound up sitting on his lap on the couch letting him play with my breasts while I wacked him off and we watched the movie. Just as he came I heard a car in the drive and we had barely enough time to turn off the tape and slink away to bed before his wife came in. These days I try to avoid cheating spouses (it can get way to ugly) but well what can I say I was younger and dumber.

Originally Posted by Hans101

Made love to my sister and came inside her without any kind of birth control. Only happened a few times, and then only because we didn't have condoms but just couldn't stop ourselves.

Originally Posted by Bad_Old_Man

Riskiest was probably assuming my aunt was too old to get pregnant

Originally Posted by jasonmason

Fucking my stepmom, way back when, while my dad was asleep upstairs.

Hans, Bad old man, or Jason...which one of you are more twisted?

How about when Widow's hubby got thrown in jail for a DYI during role play session and Widow 123 became the bottom bitch? read on!

Originally Posted by widow132

There was also a time where my husband and I were playing me as the hooker and him and his friends as the johns and I was on the street with the pros and he failed to pick me up and I was at the mercy of a pimp for two nights while my husband was in jail. That was scary yet now it turns me on thinking of that episode in my life.

Originally Posted by NoMoreNoMore

Had a relationship with a coworker. We used to meet down in the basement. She'd start up the check writing machine and we would go to it. I met her at her house a couple of times and we would go downstairs and enjoy each others company. Meanwhile, her husband was upstairs watching his shows. He no longer had any desire for sex so she turned to me. She had moved on to another job and I ended up somewhere else, but when layoffs started, she got me a job at her new place. We then did it in the elevator.

Originally Posted by Arianthe

Wild, kinky sex in a disabled toilet across the hall from police licensing headquarters. With a uniformed officer.

Smallgirl that is hot! I love you you freak! Tell hubby and his dick will be hard a granite, I promise!

Originally Posted by smallgirl

in my bad and wild days i fucked hubbys best friend downstairs in our den while hubby slept upstairs in our bed...and i did not get caught either.

Originally Posted by RjThoughts

Having sex with a woman I met at a wedding reception in a small room that had been set aside for the bridal party, while her husband and daughter were outside the door talking.

Holy shit! How could she have sex with both her hubby and daughter on the other side of the door. Were either or both of you part of the wedding party?

Below is the absolute winner! thank you for your service sir!

Originally Posted by timelegend

When I served in the US Army in South Vietnam I visited the local brothel. When you first walk in the door you enter a parlor room decorated in French tapestries and furniture. The girls all sit around and you pick the one you want. She leads you down a narrow hull way with rooms down both sides with only a screen of beads for a door. I was led down to the last room on the right. I leaned my M16 against the wall and undressed all she had to do was slip off her dress and lay on the bed. The room was about 5x5'. I had just finished shooting a load when I heard screams and gunshots. I grabbed my M16 taking the safety off and stepped out of the room and there stood 2 freakin Viet Cong going room to room shooting at will. I emptied my M16 taking both down, after my knees and hands stop shaking I realized they had missed me by inches the wall behind me was full of holes. I still remember that sexual encounter as if it just happened yesterday.

[Dirtydak]

Biggest risk was with an old girlfriend in her loft with her parents downstairs watching tv if they looked up long enough we would of been caught with her bouncing on top.

[Somehowyou]

I have had lots of danger sex with friends and co-workers while husbands and wives were lurking about. I had sex with a gf in a parked car when my wife drove by us on her way to work. I have met prostitutes in countries where prostitutes were illegal. I have navigated many a crime filled street in a 3rd world country. Streets on the bad side of town trying to find the brothel. There is one certain experience that was quite a thrill I can share...

I was traveling on business in Europe. I was visiting a large European city. It was my first and only night in that city. I was pulling an all nighter trying to see all the tourist sites. I did not speak the language and very few people there spoke English. I was at the bus station at 2 AM and a slutty transsexual prostitute walked by me. I stopped her to ask directions. She did not speak English either. She seemed to know where I wanted to go and made a motion for me to follow her and so I did. We were able to communicate with broken latin and English and hand gestures. She stopped and pointed down a street in a general direction. It was clear that it was the end of the road for her. I tried to thank her and I gave her a kiss on both cheeks. She asked me if I was interested in having sex with her. My cock started to stir. I asked if she was a transvesti and see shook her head yes. I acted surprised and my cock continued to grow. She started the negotiation at 60 Euros and I negotiated for 20 Euros. I followed her down an alley. I thought I we would go to her room but instead she stopped in the alley. She leaned her back against the wall. She put one foot stiletto clad heel up against the wall and motioned for me to come to her. I remembered thinking "What? Are going to do it in a dirty alley?"

It was dirty filthy and wrong. I grabbed her and we kissed. She unbuckled my pants and unzipped my zipper and pulled out my cock. I pealed her un-cut cock out of her little panties and stroked her cock to hardness. I got down on my knees and gave her a few sucks for good measure. Then she turned around and stuck out her ass. I touched her ass with my cock and then pulled back. I had a condom in my wallet. I got it out and put it on. She said something akin to "Oh yeah" like that's not a bad idea. I placed my condom covered cock in her ass and started humping. The entire experience felt filthy , dirty, and wrong (just the way I like it). I came in about 3 minutes. She offered me some dried Wet Knaps or something. I grabbed them and wiped myself and tried to melt back into the streets.

In this particular country, prostitution is illegal and cops are know to hand out 500 Euro fines. I was warned about this. As I walked down the street within a minute I walked by two policemen. I am so glad I had the condom!

[CuriousKittyJen]

Originally Posted by IARainman

i'm fixed, want a load of my unleaded seed?

Mmm, sex and being filled without the risk of getting preggo. Never been with a man that is fixed. Could be fun. hehe