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Kinkiest real life experiences

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Got an extra room?

SandraMustard said:
We had two college age brothers staying in our place for a week. I gave one an impromptu blowjob (if you consider ten seconds oral contact a blowjob) and considered having sex with both of them.

Younger bro obviously told older bro what I did. Older didn't believe it and waited for a chance to ask me when hubby wasn't around. I offered him one and full sex. He wasn't interested in either because "you're too old." Fuck! First time I've ever been turned down. :mad:

He told me little bro is a virgin and terribly shy. If I take his cherry, it would be great. I said I'd consider it but I mentioned they'd have to be ready for my covered-only rule.

Last night they came in late (missed dinner), drunk as skunks. Sitting on the sofa watching the TV, little bro starts pawing me in from of my husband. I realize he could pass out, throw up on me, or any number of fails. It wouldn't be any good for me and not worthy of his first time. I made big bro put him to bed.

So, they left for home/dorm/whatever this morning. They were apologetic for their behavior and cleaned up the guest bedroom. But little bro is still a virgin and big bro missed his cougar experience.

I'm not a slut. I have standards for exercising my freedom.
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These poor boys missed out on an amazing experience.... im college aged... got an extra room? :) I still need my cougar experience ;)
 
darenCA20m said:
These poor boys missed out on an amazing experience.... im college aged... got an extra room? :) I still need my cougar experience ;)
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Nice try. I may not have gone to college but I've always kept my eyes open to notice details - like your username and join date. If you joined Literotica six years ago as a twenty-year-old, you should be twenty-six now (or soon). Are you a med student, Mr College-aged?

What's with the painted toenails avatar? Are they yours? Do you have a foot fetish?

Well, Dude, you're on the wrong coastline to visit me anyway. I'd suggest when you shop Wam-alart that you keep your eyes open for who's eyeballing you. :cool: Oh, and don't wear sandals, your toes might attract a lion.
 
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SandraMustard said:
We had two college age brothers staying in our place for a week. I gave one an impromptu blowjob (if you consider ten seconds oral contact a blowjob) and considered having sex with both of them.

Younger bro obviously told older bro what I did. Older didn't believe it and waited for a chance to ask me when hubby wasn't around. I offered him one and full sex. He wasn't interested in either because "you're too old." Fuck! First time I've ever been turned down. :mad:

He told me little bro is a virgin and terribly shy. If I take his cherry, it would be great. I said I'd consider it but I mentioned they'd have to be ready for my covered-only rule.

Last night they came in late (missed dinner), drunk as skunks. Sitting on the sofa watching the TV, little bro starts pawing me in from of my husband. I realize he could pass out, throw up on me, or any number of fails. It wouldn't be any good for me and not worthy of his first time. I made big bro put him to bed.

So, they left for home/dorm/whatever this morning. They were apologetic for their behavior and cleaned up the guest bedroom. But little bro is still a virgin and big bro missed his cougar experience.

I'm not a slut. I have standards for exercising my freedom.
Click to expand...

Don't take it personally, Sandra. I'm sure a cougar experience was not the goal when they went.on spring break. Spending all day at the beach with thousands and thousands of bikini clad coeds whet their appetites for younger pussy. They were too young and inexperienced to appreciate the refined charms of a mature woman.
I'm a man who has enjoyed the pleasures of all kinds of women, but at that age even I probably would have declined your offer--although years later I would eventually regret that decision. Once when I was in college drinking the night away at my local watering hole a woman who appeared to be in her fifties came on to me. I turned hDr down--I was looking for someone closer to my age. I still regret that decision. Many times I have wondered what pleasures she could have given me and what she had to teach me about satisfying a woman.
 
Much much to kinky to post in a public form but it did involve myself and a woman! Blushing, just thinking about it!
 
Kinkiest

In the early eighties my wife and i rented out a bedroom to a friend for extra money. After a night of drinking, wifey and i were buzzing and i knew our roommate would be home shortly. I asked her to strip off her clothes and lay face down on the couch with a pillow under her stomach so her cunt would be slightly exposed. She was to stay in position when our friend came in to excite him and see what he would do. I lifted the blinds slightly so i could go outside and view his entrance. When he opened the door and walked down the hallway glancing into the living area he turned pale. From my vantage point, i saw that he walked off for a minute but then I saw him poke his head around the corner to look. He must have convinced himself that she was asleep because he slowly crept to the entrance of the room and dropped his pants. He had a raging hard on and started flogging his cock. He inched closer to see her cunt crack. In no time, he shot cum all over the living room carpet. He brushed over the jism with his socked foot and hurriedly scampered to his room. I came in the house and grabbed my wife and we went in our room and fucked wildly knowing he had gotten off watching her beautiful ass.
 
One of...

Eating my cum out of my fiance's pussy straight after sex.

Drinking my fiance's piss while she sat on the toilet.

Tying my fiance up in a barn and taking her in a non-con roleplay while she was on her period, blood trickling down her milk white thighs as we fucked...
 
Years ago, my then wife and I were at a wedding reception. She brought me a wine glass full of her pee, and while I sipped her piss, she danced and flirted outrageously. The glass was refilled throughout the evening. Deliciously degrading.:)
 
recently,
my cousins car had died. so her bfs mom drove her to the store. I happen to be there getting some movies. she text me so we met for lunch. apperantly they are very close. so her bfs mom said she would drive. we get to the mall cause the food court offered most options. but my cousin gets in the back and gives me a bj while her bfs mom watches.
 
dade37 said:
recently,
my cousins car had died. so her bfs mom drove her to the store. I happen to be there getting some movies. she text me so we met for lunch. apperantly they are very close. so her bfs mom said she would drive. we get to the mall cause the food court offered most options. but my cousin gets in the back and gives me a bj while her bfs mom watches.
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WOW..what an adventure.
 
Yes it was. I came so hard. Those two would talk dirty all the time.
 
xdressslut said:
I would have to say getting all dressed up and going to the adult movie theater and having several guys trying to have theier way with me let's say several of them did just that!!!!:kiss: es Cheryl
Click to expand...

Well I did not dress in drag, but it was at a adult theater. Our theater we stand in the back if we wanted to play. Well on this night, I stood in the back and decided to do the full monty, I dress down to my b-day suit, srood over a seat and had guys go to town on my ass. Some fuck me so hard I thought my ass split!. Times, I had a cock in one hole and a cock in the other. Dont know how long it went on, but I know some one took 20.00 from my wallet while this was going on. If it would been 40.00, it still would of been worth it
 
Several years back I was out at a pub. A woman was flirting with me a lot and making comments about my kilt - asking the usual questions. She eventually asked me back to her place so she could 'explore'. We went in and she sat me down on the love seat. Her hands started on my knees as she looked me in the eye. They slid right up my thighs, under the kilt, till she had hold of my cock in both of her hands. She stroked me under the kilt till I was fully hard, then she pulled the kilt back and began sucking me like a pro. After about 10 minutes, I heard the door open. Her friend walked in and stopped when she saw what was going on. The girl sucking me never even paused. Eventually, her friend came in and sat on the couch across from us and just watched. Every once in a while I would see her touch herself a little, but she basically just sat and watched us till every drop was sucked out of me and swallowed. Once that was done, I walked over to her friend, lifted my kilt and asked her if she wanted a turn. She said she'd like to, but she was married and didn't think she should. I squeezed her breasts and said it was a shame, but that I understood. After that, I took off. Never saw either of them again.
 
SandraMustard said:
We had two college age brothers staying in our place for a week. I gave one an impromptu blowjob (if you consider ten seconds oral contact a blowjob) and considered having sex with both of them.

Younger bro obviously told older bro what I did. Older didn't believe it and waited for a chance to ask me when hubby wasn't around. I offered him one and full sex. He wasn't interested in either because "you're too old." Fuck! First time I've ever been turned down. :mad:

He told me little bro is a virgin and terribly shy. If I take his cherry, it would be great. I said I'd consider it but I mentioned they'd have to be ready for my covered-only rule.

Last night they came in late (missed dinner), drunk as skunks. Sitting on the sofa watching the TV, little bro starts pawing me in from of my husband. I realize he could pass out, throw up on me, or any number of fails. It wouldn't be any good for me and not worthy of his first time. I made big bro put him to bed.

So, they left for home/dorm/whatever this morning. They were apologetic for their behavior and cleaned up the guest bedroom. But little bro is still a virgin and big bro missed his cougar experience.

I'm not a slut. I have standards for exercising my freedom.
Click to expand...

Probably both wanking off thinking about you...for some time to cum
 
I met a woman at the mall in the grocery section on a slow tuesday morning. She was out there exploring and our eyes met. She was a pantiless exhibitionist and gave a me great show of her hairy crotch... we kneeled down next to each other trying to explore buying shoe polish... She was literally dripping and wiped her cum on to a small handtowel which I bought... i cam in my pants... I was 22 then and she was probably 35-40.
 
My wife's "cousin"(not actually related) who is about 15 years older than me has always commented about how good looking I am and has gave me some extra hugs. Anyway we were on hard times and my wife was ill and out of work. One day her cousin and mother showed up. Her cousin had bought us a big load of groceries out of the goodness of her heart. I was over joyed by her kindness. So while my mother in law was with my wife at other end of house myself and the cousin carried in and put up all the groceries. We put up the last thing in the back room and as told her how I appreciated it she came towards me for a hug to which I normally back up. I didnt this time. I hugged her tight and for a bit. She kissed me on cheek and as I turned my head she planted one on my lips. She pulled her head back and I smiled so she kissed me again. I opened my mouth and kissed her back. She immediately grabbed my ass as we kissed. I broke the kiss and started to step back when she grabbed my cock. I let her play with and she asked if she could see it. So I let her undo my pants and pull my boxers down a little. She stroked a few times and licked it. She winked at me and whispered in my ear and said that would be in her pussy one day. Hasn't happened but she gives me a wicked look every time I see her
 
One former partner of mine was INCREDIBLY good at giving massages, which was handy because I did (and do) a lot of physical activity (no, not just that). Anyway, one night after a stressful day of work he told me to lie down on the bed; I don't know what the heck the oil was he was using, but it smelled amazing - sort of lavendery - and all the tension just drained from me, and it's entirely possible that I even dozed off at one point while he took extra special care of my lower parts.

This went on for almost an hour, and I didn't realise just how much oil he had used on me until he slipped his cock into my arse and pounded me senseless; quite a mood change, going from blissful insouciance to wild passion with barely a second in between, but an amazing orgasm is an amazing orgasm. Don't know if I've gushed that hard since.

I should look him up some day ... :D
 
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rainbowdash30 said:
One former partner of mine was INCREDIBLY good at giving massages, which was handy because I did (and do) a lot of physical activity (no, not just that). Anyway, one night after a stressful day of work he told me to lie down on the bed; I don't know what the heck the oil was he was using, but it smelled amazing - sort of lavendery - and all the tension just drained from me, and it's entirely possible that I even dozed off at one point while he took extra special care of my lower parts.

This went on for almost an hour, and I didn't realise just how much oil he had used on me until he slipped his cock into my arse and pounded me senseless; quite a mood change, going from blissful insouciance to wild passion with barely a second in between, but an amazing orgasm is an amazing orgasm. Don't know if I've gushed that hard since.

I should look him up some day ... :D
Click to expand...

If not I can sub if you like?
 
My GF and I work in a club, and one day she was the first one to arrive, so a few days prior she asked me to come early so we could have some fun in the empty building.
She got there a little earlier than me, but we were still the only ones for at least an hour, so she pulled me upstairs and gave me a blowjob on stage, I fucked her in front of a mirror in the backstage and then ate her out in the kitchen and took a cheeky photo (pun intended) - see attachment.
 

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Having sex on the beach infront the Hilton, only to realize a guys on the balcony with binoculars watching , i gave him a show lol
 
The kinkiest things we did were probably watching my wife having impromptu sex with other guys through the cracks in bathroom stalls and night clubs. Did it several times with guys we just met at a club. Once with two guys, they took turns with her straddling one over the toilet while sucking off the other. Other times it was with one guy. Always attracted a crowd of me wanting to look too. Once we got caught by security and kick out out of the club, another time the guy's fiancé was brought in by another guy who he unlocked the door with a coin and swung it open while my wife had his big hard dick in her mouth. You should have seen the look on his face, lol.
 
walking hand in hand with my wife along a public nudists beach at one of the canary islands. About 90 % of the beach walkers were clothed. I was totally nude wearing my biggest metal cock cage, my wife topless with the key hanging visible between her tits. Got a lot of curious, interested, also outraged looks. Was so humiliating and alsovery arousing for me to be so on display. Made chastity beach real.
 
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