What is the*naughtiest*adventure that you ever experience before?

handyGiraffe's Avatar
About 10 years ago I was moving furniture to San Antonio that I purchased at an Estate Sale near Tyler...I was on the back road direct route between there and Austin when I had a problem with my trailer wheel bearing ....it was very hot...the road was two lanes and I creeped to the very next place with a large enough parking area and shady trees...a country church...with one mini van parked in the parking lot.....

It was still 100 degrees...I repaired the axle/bearing and got very dirty and sweaty and greasy in the process....I had taken my shirt off...and used their outside water spicket to get a drink of water earlier..while I was doing that....a hot well built young lady in her late 30's to early 40's stepped outside what appeared to be a annex building adjoining the church and asked if I needed anything...she was wearing shorts and a T-shirt showing a nice curvy MILFy body. Wow....I thanked her explained to her that I was repairing my trailer (which she could clearly see) and asked her if when I finished could I use their restroom to clean up and change and she said "Sure!" to just let her know when I was finished. She told me that she was there practicing her music for Sunday...giggled and said that it was a break away from family duty and kids for a couple of hours that she looks forward to every week during the summer months---I explained that I was still several hours away from San Antonio...didn't want to get back in my truck greasy or nasty..LOL..she said no worries just knock...shortly after that she reappeared with a glass of ice water....I was on my back laying next to the trailer and she walked up and stood next to me...her shorts were a baggy..and the way she was standing I could clearly see that there were no panties in use and a clean shaven kitty was slightly covered....yummy. {I am thinking...must be a gentleman...stop looking....coulding stop...ahemmm....}...she said she had some ice water...clearly saw me looking at her legs and up her shorts and knew exactly what I was seeing....and didn't move away ..she stood there and let me drink it in....and I sat up and gratefully downed the ice water....she said if I needed more to let her know...and smiled and walked back to her building....(I am thinking clearly music practice was not the only thing she wanted to practice..or am I just being stupid and making more out of what I had seen than was really there...)

Anyway, when I got finished I knocked on the door...she opened it and pointed out where the restroom was...I could not help but notice that her nipples where showing through the T-shirt..hard as two thumbs sticking straight out...again, could not help but linger while I looked...and she giggled again..........I thanked her broke myself away from the view and went down the hall and took a standing sink bath...in a few minutes I was finishing and there was a knock on the bathroom door and before I could answer..the door slowly opened...there was "Miss Music" standing in the door and I was standing with nothing on...she stepped in quickly and closed the door and without saying anything glanced at the little giraffe and slowly approached....getting down on her knees she gently cupped mini G and then began slowly licking all around the area from my navel to mini G and around my thighs--- and----- then started an excellent BBBJ with plenty of wet sloppy sucking on the balls and awesome eye contact....she continued stroking me and licking and mini G got harder and harder.

After a very few minutes of that I told her that I was going to cum if she continued..and she slowed down...backed off...asked If I wanted to see her boobs to which I replied Oh yes Mam...she slowly....pulled off her top...looked at me for my reaction and seeing my appreciation she stood up...I licked her nipples which were rock hard and erect...told her how beautiful she was..she said that she had never done anything like this before...but that she was horny and she needed someone to show her some appreciation even for just a few minutes....she said she could tell from how I looked at her in the parking lot that I thought she was hot and she wanted me to lick her all over.......

I asked her to take her shorts off which she did.....and in the process revealed a shaved kitty that was irresistable to me...she leaned agains the sink with her legs splayed open as I slowly licked and then found and slowly and softly licked her clit and lips until she started to get wet......she started to moan and I asked her to straddle my face rcg....and she did and I started licking and sucking and tasting her ...her pressing down harder....I lifted her and began licking and rimming her while slowly and deliberately fingering her G spot...and then returning to her clit.... as she got wetter and wetter and moaning louder and then she had an extended moaning "O" just drenching on my face as she finished....ummm awesome..

Recovering she quickly leaned into 69 with me softly licking up her wetness and caressing her with my tongue...she squirmed and looked back and said I want you to cum in my mouth when you are ready....and she began to take me down her throat until she had mini-g all the way into her throat and tightly holding her lips around me ....slowly sliding her lips all the way from the base to the head with a bit of tongue action on the tip until I could not hold it and then I had to go and exploded cim....and she went to town until she drained me.....and I began to lick her and probe her pussy with my tongue and rock her clit... until as I was completing she had another smaller "O" and we both collapsed into an incredible explosion of unexpected....on the complete sly...in the most "naughty" of locations.....awesomely mutual oral sex.... before we got up kind of shy and she dressed we gave each other our mutual phone numbers and then I headed on down the road to San Antonio.......I know where she is...LOL and she knows where I am..but we have never made contact again......

Since that time...69 has been my favorite kind of sex.....I think I found more of an appreciation for it just because this adventure was so unexpected-- I love the taste of a hot woman anyway...I can never get enough of it....and I have never had another kind of "stumbled upon" sex adventure as I did that day....
oldtiger's Avatar
While not my naughtiest ever, it is in my top 5, and happened last week.

I'm at work, chatting with a former FWB, a dancer here in SA. She's telling me about how she's not feeling well. I offer to pick up some OTC stuff for her, and swing by after work.

I get to her apt., go in and check on her. I also am introduced to her new roommate, a co-worker of hers. After diagnosing what sounds and looks like a minor bout of sinusitis, I sit on the couch and we start conversing. Somewhere along the way, RM asks how we know each other, I look to FWB, because I don't want to say anything she hasn't disclosed. SO FWB chimes in and says, "this is the guy with the huge dick".

I wasn't sure what to say, and then RM aks if it's true. I respond it is, and then she asks if she can see it! Being the gentleman I am, I accommodate and pull out the cub, who at this point has been paying about half attention to the convo. RM says it is the biggest she has ever seen, and I explain he does get bigger. She proceeds to stroke the cub and give me a handjob!

I am loving this, the cub is fully into the convo, she's doing a great job, FWB is sitting across from us watching. I start leaking, and her handjob becomes a nice slick rub.

Then, all of the sudden, RM jumps up, yells "Oh shit! I forgot my BF is on the way!". I'm start trying to stuff the cub back in my shorts, she freaking out wiping precum off her hand on the couch, FWB is laughing her head off. Sure enough boy friend walks through the door about three minutes later! I'm the epitome of cool up at this point, look up and nod and continue the conversation with FWB without missing a beat.
Had many great ones.... here are two...

#1 While flying to Germany to be stationed, I was in my twenties and I was flying with a beautiful young lady that I had already had relations with about a year prior at our previous duty station.. It was her and I and the "Mile High Club".. I was much smaller then. LOL

#2 Got a great BBBJ at the end of the Santa Monica Pier one late evening when I was in college!! Woot Woot!
Sonya Playmate's Avatar
Guys HOT HOT naughty adventures...Me so horns lol
shooter1a's Avatar
I posted this in a similar thread about two years ago.
It is similar to Mslovesbj's.
40 years ago, well in 1977 actually, I was shooting a "Girl in The News" and decided to take the photo on the overlook atop the Tower of The Americas. When the YL and I got on the elevator I noticed it was being run by an old friend. He said that it was almost time for his afternoon break and there was very little traffic (Jim's Restaurant was closed for remodeling) and it wasn't tourist season so we could take the elevator up and I could drive
We stopped about 50 feet short of the overlook and she dropped her hotpants (that was a style so old that MSN has never heard of them) placed her very very fine ass against the glass wall overlooking downtown San Antonio.
When we got back to ground level and turned the elevator back to its controller he started laughing at the butt smudge on the glass. That story followed me trough my newspaper career.
The Executive Editor called me into his office the next week and told me that he was not going to ask me if the story was true because he didn't want me to lie to him and if it was true then he would have to fire me but to never ever have sex in the Tower of The Americas elevator. As I walked out of his office I heard him under his breath say "Way to go." CK was a cool dude.
One that is always a nice fantasy but doesn't work in the real world is sex on the beach. Too much sand and too many Mosquitos.
AngeLisa's Avatar
If u been to north star mall then you seen the bigg boot!!! I had a girl0n girl treat there about a yr ago.... 2dresses. Was waiting for my ride and I ended up tasting a beautiful mixed chick, I felt lucky because she was a V. So she said. I'm like we on the boot tho!!!!
Sonya Playmate's Avatar
If u been to north star mall then you seen the bigg boot!!! I had a girl0n girl treat there about a yr ago.... 2dresses. Was waiting for my ride and I ended up tasting a beautiful mixed chick, I felt lucky because she was a V. So she said. I'm like we on the boot tho!!!! Originally Posted by me_jucci
mmm girl on girl...
Seducing and nailing a priest - a HOT priest. Originally Posted by Tara Foxx

There's a special place for you in Hades!!!
1. Senior year of HS. We used to have half days then a dance in the gym for special occasions. I observed a junior I was fucking leave and I followed her to her locker. I had her on a staircase. I don't know if any of you attended Catholic school to understand the ramifications of us getting caught.

2. Freshman year of college. I was in the Student Hall on Friday night during Homecoming weekend. Came across my jump off in the building. Pulled her in the staricase, went to the third floor and had my way with her.

3. I lived in Connecticut at the time. My roommate told me about a strip club. Went one night & met a bombshell. We talked about dating. Went home & told my roommate. Come to find out he met her couple of nights before. To make along story short, we dicked her down!!!!

I can go on & on. I've had sex with parents in the next room, kids in the same room, gangbangs, MMF, MFF, swing clubs, strip clubs, parks, woods, basements, cars, pools. I'm a fucking pervert!!!!!
GentlemanCaller007's Avatar
If u been to north star mall then you seen the bigg boot!!! I had a girl0n girl treat there about a yr ago.... 2dresses. Was waiting for my ride and I ended up tasting a beautiful mixed chick, I felt lucky because she was a V. So she said. I'm like we on the boot tho!!!! Originally Posted by me_jucci
Damn jucci! Risky business. 410. Cops are driving up and down that stretch all the time. I like a little danger but that's just cRaZy!!
Gotta admire it though. Good for you! Livin' la vida loca!
GentlemanCaller007's Avatar
I kinda like sand up my ass...but, I'm kinky like that! (lol) You should try *pop* rocks mixed with a little mint...fun, fun, fun!

I'll have to think about which one(s) to share...be back later! Originally Posted by Likinikki
Catching up on my reading and started at the beginning this time. Nikki you are SO clever and funny!!! This made me cry! *pop* rocks...WTF?

Ok, so my cRaZiEst: I also had a GF once who thrived on public adventures (miss her). We both worked on the Riverwalk for awhile... So one night we go to what was then Fat Tuesdays. We get some drinks. We notice that the upstairs section is closed off. I notice the wheels turning in her head and the look in her eye. Oh God...

So we sneak upstairs while no one is looking. The top floor is empty. We go to one of the balconies overlooking the Riverwalk and watch the people walk by while enjoying our drinks. Once the buzz settles in and we've "scoped the situation" she says, "Fuck me! I want you inside me right now!" Then she hikes up the back of her skirt and juts out her ass. Her ass is bullet-proof, amazing and impossible to say no to. So I start doing her doggie while she holds the bars of the balcony. I am trying to be as discrete as possible (because as anyone knows, there are riverwalk cops that constantly and randomly wandering around down there). So I'm while constantly looking around. No one seems to notice us. Then...

I hear noises to my left. Turns out the friggin MANAGER'S office is right on our left AND he has a window facing our balcony!!!! WTF!!! But, his blinds were drawn so...
I keep going. So this guy can come out at any minute. Dozens of people are walking by below (but no one ever looks up). EXCITING!!! After I'm like 1/2 way to 3/4 of the way done this guy walking over the bridge on the street level notices us, and just stops, throws his arms over the bridge railing and stares at us. F'n Ass!!!(I'd do the same. Lol) So F him! I keep doing it for another 5 min or so until I start freaking out because he's been staring so long (drawing attention to us). There are bike cops street level and all we need is for one to see this idiot gawking up at the sky and look up to see what the hell he could possible be staring at standing on the bridge.... Then get on the walkie and cop-swarm. The hell with that. So sadly, I had to abort and take the conclusion somewhere less crazy!

GOOD TIMES! Damn I miss being 20-something.
Naughtiest experience ever...hmm. That would have to be the multiple sessions I had with a Mom and Daughter duo at my apartment complex in Houston, almost 20 years ago. They were not pros, just a couple of saucy girls who liked to play, and I got lucky. And yes, it was mom-n-daughter at same time a couple of times. We carried on for about a month until they moved away, out of state. Unforgettable!
shooter1a's Avatar
While it does not top my elevator experence it was fun and envolved some of you.
About three years ago, while we were having our socials at a very secluded and private location, I had brought a newbie provider to intorduce. She was well recieved altho no longer a provider so I will not name her. After the social starts breaking up about 9pm, she and I are making out in my SUV around the corner from the frount door. Well the van was a rocking so no one started knocking and we did the deed. As I unloaded, bare I am ashame to admit, I look up and 7 or 8 of our brothers were standing by the car and cheering us on. She and I stepped, jaybird bare, out of the SUV and bowed formally. This was before the fracus in Houston made our socials so politically correct.
tst888's Avatar
On the beach and it totally sucked! Sand up my butt, etc. Never again! spring break + alcohol = stupid ideas lol Originally Posted by Pepper_Springfield
Yupper, I grew up in Calif. Know the feeling but got good at keeping the sand out. Heheee