djyak
MILF Loves To Please
- Joined
- Nov 4, 2003
- Posts
- 2,517
What's the biggest sexual related risk you've ever taken?
- Thread starter SgtSpiderMan
- Start date
Oh such a tease...my imagination is running wild. Does your husband know what happened?
lilsarah91
Literotica Guru
- Joined
- Mar 15, 2013
- Posts
- 2,877
Biggest sexual related risk I've ever taken? Probably the three Craigslist Gang Bangs I've set up. And I'm probably gonna set up another this Summer
Cindykay
Experienced
- Joined
- Dec 17, 2012
- Posts
- 35
sex in a public area
my boy friend and I were at a lake in the bed of his pick up truck. Things got going pretty heavy and we covered up with a old wool blanket and started our sexual pleasure. there were lots of cars driving around and then we had the sheriff's pickup pull up along side of us. I did not mention it was 95 degrees AND we were covered up with a wool blanket! we pulled our clothes on as best as we could as he watched, thenn he just shook his finger at us and to us to leave....we could have been arrested! What would my mom ,dad and church friends say!
my boy friend and I were at a lake in the bed of his pick up truck. Things got going pretty heavy and we covered up with a old wool blanket and started our sexual pleasure. there were lots of cars driving around and then we had the sheriff's pickup pull up along side of us. I did not mention it was 95 degrees AND we were covered up with a wool blanket! we pulled our clothes on as best as we could as he watched, thenn he just shook his finger at us and to us to leave....we could have been arrested! What would my mom ,dad and church friends say!
DirtyAllie
Really Really Experienced
- Joined
- Apr 12, 2014
- Posts
- 381
Yup, that's what my tattoo is for
He does still play in leagues, I play on one of his teams, its a lot of fun.
Been married thirteen years last month, proof opposites attract.
sexlover66
Literotica Guru
- Joined
- Jan 18, 2009
- Posts
- 1,168
Would be with my first wife...we hadnt seen each other in a few weeks because issues...but the second day i was back we took the kids to the lake...it was nice out and we were getting hot and heavy and went over into secluded area by the lake and fucked our brains out....the kids were all nearby and a couple of boats passed by on the lake itself...it was a huge thrill
Jaxpantyguy_
Really Experienced
- Joined
- Dec 2, 2013
- Posts
- 187
Snuck into my stepsisters room at night, carefully pulled the covers down and her nighty up and gently played with her pussy, was first ever and came just from touching her, thankfully she did not catch me as I know she would have told our parents
Eilan
Absent(ish)
- Joined
- Jan 24, 2005
- Posts
- 10,431
Josh Duggar posts on Lit?
Jaxpantyguy_
Really Experienced
- Joined
- Dec 2, 2013
- Posts
- 187
For years I also would steal her panties from the hamper and masturbate with them, I loved when they were fresh worn and her scent was fresh, sometimes I would lick the sweet spot and get it good and wet and it was just like having her juices, This was a way of life for a few years and even included her sisters panties when she got a little older, All this fun went on until I got into high school and got my drivers license so no longer spent as much time with my father and the stepfamily
DavidLynn46
Experienced
- Joined
- Jun 10, 2015
- Posts
- 39
mmm
having sex with a coworker in the officer during business hours...
having sex with a coworker in the officer during business hours...
Now that would be a hell of lit story
Teechurgye
Literotica Guru
- Joined
- Jun 15, 2011
- Posts
- 601
Sex with a student, just an hour after she graduated.
FWB situation with a good friend from college (she's married).
Lots of public places.
FWB situation with a good friend from college (she's married).
Lots of public places.
therearenowords
Really Really Experienced
- Joined
- Jan 12, 2013
- Posts
- 392
Had sex with a married teacher while on a school trip. Although he was taking a bigger risk than me...
So many to choose from:
Had sex with a gorgeous black flight attendant in the Miami Airport Hotel with the curtains open. I was fucking her doggy style and happened to look out the window. The air traffic control tower was not too far away and there were several guys out on the balcony watching us with binoculars. I waved and one of them waved back. We put on quite a show once we knew they were watching.
Picked up a pretty Puerto Rican hooker on 79th Street in Miami and ate her previous customers creampie out of her pussy. Did the same with a black hooker a couple of weeks later.
Sucked a lot of anonymous cocks and swallowed lots of cum through glory holes in the early 80's. Also had a lot of unprotected anal sex during the same time frame.
Got fucked in the ass by four guys in succession in the parking lot of a gay bar in Ft. Lauderdale while a crowd of about a dozen other guys watched. Would have had more but a cop drove by and broke up the party.
Had sex with a gorgeous black flight attendant in the Miami Airport Hotel with the curtains open. I was fucking her doggy style and happened to look out the window. The air traffic control tower was not too far away and there were several guys out on the balcony watching us with binoculars. I waved and one of them waved back. We put on quite a show once we knew they were watching.
Picked up a pretty Puerto Rican hooker on 79th Street in Miami and ate her previous customers creampie out of her pussy. Did the same with a black hooker a couple of weeks later.
Sucked a lot of anonymous cocks and swallowed lots of cum through glory holes in the early 80's. Also had a lot of unprotected anal sex during the same time frame.
Got fucked in the ass by four guys in succession in the parking lot of a gay bar in Ft. Lauderdale while a crowd of about a dozen other guys watched. Would have had more but a cop drove by and broke up the party.
Tenn99881
Really Experienced
- Joined
- Oct 11, 2014
- Posts
- 102
At the pool
My wife and I lived in an apartment in the south with a huge swimming pool. Tons of people would swim or lay out on the weekends. My wife and I had a few too many margaritas and I am laying in a lounge chair and she gets on top of me. She starts french kissing me and the next thing I know she has my hard cock out of my swim trunks, pulls her bikini bottom to the side and slides my dick in her cunt. She rides me in front of everyone. It didn't take me long to bust a nut. After she got up, i looked around and no one was gawking. I dont know if we became invisible but it happened and i know someone in the crowd noticed.
My wife and I lived in an apartment in the south with a huge swimming pool. Tons of people would swim or lay out on the weekends. My wife and I had a few too many margaritas and I am laying in a lounge chair and she gets on top of me. She starts french kissing me and the next thing I know she has my hard cock out of my swim trunks, pulls her bikini bottom to the side and slides my dick in her cunt. She rides me in front of everyone. It didn't take me long to bust a nut. After she got up, i looked around and no one was gawking. I dont know if we became invisible but it happened and i know someone in the crowd noticed.
I answered a Craigslist ad for a woman who was setting up a gangbang. I came by later in the night when no other guys were there and got to have her all to myself. The risk was I fucked this complete stranger bareback and finished in her pussy.
leather_spitfire
Jess
- Joined
- Jun 23, 2012
- Posts
- 1,703
a tale of when my leather addiction got the better of me...
my mothers best friend had a fuchsia pink leather biker style jacket. the moment I saw it I knew I had to be nude inside it. I had to feel it against my skin and smell the unmistakable aroma. the moment I decided I could wait no longer, I went to her bedroom whilst everyone else was outside. it was a bad time to do it, I knew that, but I just couldn't wait any longer. I knew that jacket was there and I needed to be with it NOW! so I stripped completely and pulled the jacket out of the wardrobe. it was everything I hoped it'd be. it fit so well, I zipped up all the zippers and fastened all the buckles. I was overwhelmed with the desire to pleasure myself and it was whilst doing just that I was discovered. my mothers best friend caught me in her bedroom wearing nothing but her fuchsia pink leather jacket and approaching an orgasm.
I knew it was a risk but I was powerless to resist that jacket
my mothers best friend had a fuchsia pink leather biker style jacket. the moment I saw it I knew I had to be nude inside it. I had to feel it against my skin and smell the unmistakable aroma. the moment I decided I could wait no longer, I went to her bedroom whilst everyone else was outside. it was a bad time to do it, I knew that, but I just couldn't wait any longer. I knew that jacket was there and I needed to be with it NOW! so I stripped completely and pulled the jacket out of the wardrobe. it was everything I hoped it'd be. it fit so well, I zipped up all the zippers and fastened all the buckles. I was overwhelmed with the desire to pleasure myself and it was whilst doing just that I was discovered. my mothers best friend caught me in her bedroom wearing nothing but her fuchsia pink leather jacket and approaching an orgasm.
I knew it was a risk but I was powerless to resist that jacket
secret_passion49
Really Really Experienced
- Joined
- Jul 21, 2012
- Posts
- 320
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leashedbottom
Really Experienced
- Joined
- Jul 12, 2015
- Posts
- 135
i was running an ad on phone chat line, looking for an older, experienced Dom to meet with on a regular basis, and was getting a lot of responses from men who said they were into all the things i am into but, every time i hooked up with one it was always a disappointment. i was giving a lot of blowjobs but that was it, and i was about to take down my ad. i was on my bed naked and stroking my dick while i listened to responses in my mailbox.. the usual " I am a master...blah blah blah"... erasing them when i got to number 11 and heard a deep coarse voice say "Get naked, on your knees and call..." ending with a phone number.
i dot know what it was about that message but i listened to it over and over after writing the number down. i stared at that piece of paper for a long time, laying on my belly and slowly rubbing my really hard dick on the bed. i was trembling and my mouth was dry when i dialed that number with a shaking finger. It rang once and i hung up, then dialed it again, remembering this time the directive i had been given and getting on my knees.
It again rang once and was picked up.. the voice on the other end said that if i wasn't naked and on my knees to hang up then silence... i waited and after a few seconds and the voice spoke again this time telling me that if i hadn't followed His command i was wasting my time and His... i stuttered a whispery 'i am'... He was silent for a few seconds and said that if i wanted to be considered to be His boy i had to get up after i hung up and drive to the address He gave me... i was to do this without getting dressed and to not bring any clothing with me, to park up under the carport, enter the house through the side door and put on whatever was on the table by the door.
It was dark out so there was less risk of being seen as i went out to my car, completely naked and drove to His house, a twenty minute drive to His neighborhood and another fifteen minutes to find his house. It was pitch black under the carport but i pulled in, got out of my car, looking all around and walked to the door... i was extremely nervous and shaking bad, but my cock was rock hard... i went into the house and there was the table and on it was a cockstrap which i put on... i walked into the living room and there was a tall slender man with light red hair sitting in a La-Z-Boy chair, sipping a whiskey and listening to jazz. He was wearing black lounge pants and had a crop laying across His thighs... and there was a Cat-o-nine on the end table between His chair and the sofa.
He motioned for me to stop in the middle of the dimly lit room. i stood there for a long time while He casually sipped His whiskey before He motioned with a finger for my to turn around. i did a low turn, trying hard to stop trembling... there was something about Him that had me shaking, even more than i already was from the whole situation... After coming around to face Him again He motioned for me to kneel, which i did... putting my hands behind my back... He stood up then and began circling me slowly, dragging the tip of the crop over my chest, shoulders, sides then my stomach lower back and hips... then my butt cheeks and thighs and finally my stiff cock and balls before using the crop to get down on all four.
He tapped me on the shoulder and i dropped down to my elbows, then He pressed the crop against the insides of my thighs, directing me to spread my knees further apart and in effect spreading my butt cheeks wide. He tapped my right cheek with the crop then walked over and traded the crop for the Cat and came back, dragging the leather strands over my head, back and ass, letting it fall between my buttocks and dragging it back to my shoulders. i was a wreck by then especially from the feel of the Cat brushing the underside of my balls and my asshole. The Cat lifted off me and for the longest time He just stood there... then He brought the Cat down hard on my ass...
For the rest of the night i was whipped, spanked... over His knee at one point... He put nipple clamps on me, then used the Cat on every inch of my body... He took the clamps off and pulled me to Him and began chewing on my nipples... i reacted by raising my hands and He grabbed them and told me never to do that again... and i didn't... Then He put me on my knees and stripped off His loungers, revealing a huge cock and low-hanging balls and told me to suck it. i gorged on that cock and balls like never before... i have loved sucking cock since i was 13 but never wanted it as much as i did then... He fucked my mouth, gagging me with cock... then He put me down on all four again and filled my ass with His cock and fucked me hard and mercilessly... When He was ready He pulled his cock from my well-reamed asshole and shoved it on my mouth as He let loose a flood of creamy jizz which i eagerly gulped down.
He then told me to go... and that i wasn't to call Him, He would call me... if He was interested...
It was just before dawn and i still had to make it home without being seen... i left with a sore and tender ass, a well-reamed asshole and a belly full of His cum...
i never heard from Him again
i dot know what it was about that message but i listened to it over and over after writing the number down. i stared at that piece of paper for a long time, laying on my belly and slowly rubbing my really hard dick on the bed. i was trembling and my mouth was dry when i dialed that number with a shaking finger. It rang once and i hung up, then dialed it again, remembering this time the directive i had been given and getting on my knees.
It again rang once and was picked up.. the voice on the other end said that if i wasn't naked and on my knees to hang up then silence... i waited and after a few seconds and the voice spoke again this time telling me that if i hadn't followed His command i was wasting my time and His... i stuttered a whispery 'i am'... He was silent for a few seconds and said that if i wanted to be considered to be His boy i had to get up after i hung up and drive to the address He gave me... i was to do this without getting dressed and to not bring any clothing with me, to park up under the carport, enter the house through the side door and put on whatever was on the table by the door.
It was dark out so there was less risk of being seen as i went out to my car, completely naked and drove to His house, a twenty minute drive to His neighborhood and another fifteen minutes to find his house. It was pitch black under the carport but i pulled in, got out of my car, looking all around and walked to the door... i was extremely nervous and shaking bad, but my cock was rock hard... i went into the house and there was the table and on it was a cockstrap which i put on... i walked into the living room and there was a tall slender man with light red hair sitting in a La-Z-Boy chair, sipping a whiskey and listening to jazz. He was wearing black lounge pants and had a crop laying across His thighs... and there was a Cat-o-nine on the end table between His chair and the sofa.
He motioned for me to stop in the middle of the dimly lit room. i stood there for a long time while He casually sipped His whiskey before He motioned with a finger for my to turn around. i did a low turn, trying hard to stop trembling... there was something about Him that had me shaking, even more than i already was from the whole situation... After coming around to face Him again He motioned for me to kneel, which i did... putting my hands behind my back... He stood up then and began circling me slowly, dragging the tip of the crop over my chest, shoulders, sides then my stomach lower back and hips... then my butt cheeks and thighs and finally my stiff cock and balls before using the crop to get down on all four.
He tapped me on the shoulder and i dropped down to my elbows, then He pressed the crop against the insides of my thighs, directing me to spread my knees further apart and in effect spreading my butt cheeks wide. He tapped my right cheek with the crop then walked over and traded the crop for the Cat and came back, dragging the leather strands over my head, back and ass, letting it fall between my buttocks and dragging it back to my shoulders. i was a wreck by then especially from the feel of the Cat brushing the underside of my balls and my asshole. The Cat lifted off me and for the longest time He just stood there... then He brought the Cat down hard on my ass...
For the rest of the night i was whipped, spanked... over His knee at one point... He put nipple clamps on me, then used the Cat on every inch of my body... He took the clamps off and pulled me to Him and began chewing on my nipples... i reacted by raising my hands and He grabbed them and told me never to do that again... and i didn't... Then He put me on my knees and stripped off His loungers, revealing a huge cock and low-hanging balls and told me to suck it. i gorged on that cock and balls like never before... i have loved sucking cock since i was 13 but never wanted it as much as i did then... He fucked my mouth, gagging me with cock... then He put me down on all four again and filled my ass with His cock and fucked me hard and mercilessly... When He was ready He pulled his cock from my well-reamed asshole and shoved it on my mouth as He let loose a flood of creamy jizz which i eagerly gulped down.
He then told me to go... and that i wasn't to call Him, He would call me... if He was interested...
It was just before dawn and i still had to make it home without being seen... i left with a sore and tender ass, a well-reamed asshole and a belly full of His cum...
i never heard from Him again
MilkFountain
Literotica Guru
- Joined
- Mar 13, 2005
- Posts
- 1,481
My wife danced naked under a full moon in the park
Under a full moon on a hot August night, while I waited in our camper van, my wife danced naked in a clearing in a park in Mill Valley, California. I watched through the curtains of the van. Suddenly, headlights flooded the area from a car we hadn't seen parked under trees on the far side. She ran back to me in the van. Soon, the car's lights were doused. The car didn't move. We guessed that it was some guys parked, drinking beer, and that they were even shyer on seeing her than she was on being seen.
My wife (and I!) were horny as all get out. I suggested she sneak up on the car to see who was in it. She asked what she should do if there was guys alone. I said that depended on her.
I accompanied her. We were both barefoot, creeping along in the dark beneath the trees until we got to the car. I was dressed and she had on panties and a long pullover shirt that covered her bum. Ten meters before we got to the car we heard the voices of young men, excitedly talking about what they had seen of my wife. I asked her if she wanted to go. She nodded. I kneeled down and pulled off her panties. All she wore was the shirt as she asked me for the second time if I was "Sure?" As she turned to go, I grabbed her arm and pulled her close to whisper in her ear that before she made any move to get in, she should talk to them through a rolled-down window to see if she felt safe. I squatted down behind the car, my back to the bumper.
She went around to the driver's side window. I couldn't hear what was said as she talked with them. Then I heard the car door open, heard and felt the car shift as she got in, and I listened. I heard muffled voices, occasional words, including introductions and nervous questions, and then silence. Without any continuity the car shuddered against my shoulders, a car spring creaked, and then more silence; sometimes there was a faint rhythmic shifting against my shoulders. Then, after about ten minutes I heard a guttural grunt, followed by a one-syllable giggle from my wife. After that I waited a long time, never hearing the kind of cry from her I've heard so often in the heat of her being penetrated but over the period of more than an hour, I did distinctly hear a number of deep-voiced "Yes, Now, I'm comings and Oh Gods."
Back with me in the van she said she had sucked off the four of them at least twice, she thinks more.
Under a full moon on a hot August night, while I waited in our camper van, my wife danced naked in a clearing in a park in Mill Valley, California. I watched through the curtains of the van. Suddenly, headlights flooded the area from a car we hadn't seen parked under trees on the far side. She ran back to me in the van. Soon, the car's lights were doused. The car didn't move. We guessed that it was some guys parked, drinking beer, and that they were even shyer on seeing her than she was on being seen.
My wife (and I!) were horny as all get out. I suggested she sneak up on the car to see who was in it. She asked what she should do if there was guys alone. I said that depended on her.
I accompanied her. We were both barefoot, creeping along in the dark beneath the trees until we got to the car. I was dressed and she had on panties and a long pullover shirt that covered her bum. Ten meters before we got to the car we heard the voices of young men, excitedly talking about what they had seen of my wife. I asked her if she wanted to go. She nodded. I kneeled down and pulled off her panties. All she wore was the shirt as she asked me for the second time if I was "Sure?" As she turned to go, I grabbed her arm and pulled her close to whisper in her ear that before she made any move to get in, she should talk to them through a rolled-down window to see if she felt safe. I squatted down behind the car, my back to the bumper.
She went around to the driver's side window. I couldn't hear what was said as she talked with them. Then I heard the car door open, heard and felt the car shift as she got in, and I listened. I heard muffled voices, occasional words, including introductions and nervous questions, and then silence. Without any continuity the car shuddered against my shoulders, a car spring creaked, and then more silence; sometimes there was a faint rhythmic shifting against my shoulders. Then, after about ten minutes I heard a guttural grunt, followed by a one-syllable giggle from my wife. After that I waited a long time, never hearing the kind of cry from her I've heard so often in the heat of her being penetrated but over the period of more than an hour, I did distinctly hear a number of deep-voiced "Yes, Now, I'm comings and Oh Gods."
Back with me in the van she said she had sucked off the four of them at least twice, she thinks more.
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