Kinkiest real life experiences

Status
Not open for further replies.
Kind of a tossup between 1) my aunt licking me all over, 2) watching my sister in bed with her adult son, and 3) a group fest with a bunch of bikers and mamas.

1 and 2 must have fun overly exciting for you. Id love to hear more about both of those.
 
I have a few and each time it got kinkier.

first one was I was dating a girl we were both 19 at the time. I fucked her in the field in the middle of her dorms at lunch time. got a lot of cheers, a few laughs, and a few watchers.

one time while at a public event, there was an incredible hot couple of girls in front of us, well the crowed got really tight, I accidently brushed one of the girls ass. well she pushed back into my hand a few minutes later. so I was like the hell with it, straight up grabbed her ass, and felt her ass for about 20 minutes then ventured a little lower further in, ended up rubbing her pussy a little that way for a minute or two. as I was doing this she whispered to her friend, and then she shuttered. I had stop then and she whispered to her friend again. her friend looked backed at me with a huge smile.

Years later, was at a friends bbq, and the neighbors were over too. well the lady went back home to watch her show, her daughter stayed. it was around midnight so I walked the daughter home. After a few minutes of talkting to the mom, we endedup fuckign on the couch. little did I know she had her watch us.

another time, I fucked my cousins wife in their backyard while he was sitting in a chair drinking his beer.
 
Last edited:
my second ex wife would dress in cut up clothes that showed her pussy and nipples and wear them indoors
in front of her son, that was a turn on.

She sounds like my kind of woman... did that turn on her son as well? Anything more to that story?
 
Kinkiest real-life experience was probably going out to the bar with a friend and his wife (and a couple of their friends), "walking her out" when it came time for her to plead one drink too many and go home early... and then taking her back to my place and fucking her.

Which was actually a really terrible horrible no-good very-bad decision in a whole lot of ways, but I won't lie, the sex itself easily ranks in my top ten romps of all time. We eventually broke off the affair but I'm still friends with her... him, not so much, and they're not married anymore.

(Not to give the impression that I did this all that often, but come to think of it, one of my other best romps involved cheating, too -- although it was me cheating instead of her, that time. Luckily that situation didn't involve marriage, thank Christ.)
 
Here's a reader's digest version.

I met Dena when I was on a photo assignment. I was taking pictures of a theater group for a couple of friends. Dena had a very butchy side to her and she was bi. Because my friends were gay she assumed that I was and the fact that I'm androgynous added to her false conclusion. Dena was very attracted to me and when they assured her that I was not gay she let them know that she had an attraction for me. They stopped by a friends studio I was using to look at proofs and they brought Dena with them and they let me know she was interested.

Dena and I began dating. I liked her butchiness and her manly mind. I felt comfortable being with her. Our talks eventually turned to sex and sexuality and she opened up to me about being bisexual and having a thing for fem boys. I was never completely comfortable being androgynous but I would be less comfortable being macho.

I opened up to her about why I looked so feminine and my anxiety about it. You see, I was born with a slight abnormality where my testicles were un descended and a never had complete puberty. Basically I am a pseudo hermaphrodite for lack of a better term or perhaps have partial AIS. I have a small but mostly functioning although my ejaculate is clear. I have very little body hair and facial hair. I was worried that my lack of size would be a problem for Dena but she told me the same old tired line that women tell men who have small ones. "It's not the size but how you use it." She went on to tell me that she usually could not cum from intercourse anyway. That was not entirely true.

After we became boyfriend and girl friend Dena considered me both male a female and Dena had that same thing which in her case seemed to be dictated by where she was in her menstrual cycle. When she felt girly I would use a strap on on her and she would orgasm several times.

One afternoon when we were playing dress up she said, were going to take this to the next level. We had done anal play with her fingers and toys in me because sometime I needed that to orgasm. Dena had a way of caressing my mind. I guess because she could see thing with both a male and female brain this came naturally to her. She made me up like a proper lady. I was wearing shorts the kind with an elastic band women's sneakers and a powder blue T-shirt with a bra. She invited her friend Jolene over. Jolene had seen me enfem and the fact is I pass even without make up and women's clothes.

Jolene, Dena and I talked in a very academic manner about my androgyny. Jolene had majored in biology and her brother was a pharmacist. She was fascinated by my situation because she had a cousin who was intergendered. Dena had me show my genitals to Jolene to satisfy her scientific curiosity. I was getting really aroused as I slipped out of my shorts. I was blushing and getting erect. Jolene asked Dena if she could touch my genitals and Dena agreed. Jolene's touch turned into a fondle. Jolene smiled, made a graceful exit and gave us both a wink.

Dena was dripping wet and ordered me to tease lick her clit. She was on the cusp of her male side. She began talking to me like a macho man in the throes of lust. She called me a hot fucking little whore. She ordered me to the bedroom and ordered me to lay across our raised California king bed and wait. She came into the room wearing an 8" long and strap on that was way thicker that the average cock. She gave be about 15 minutes of analingus interrupted by a few swats with her bare hand. Then she said, "This is going to the next level slut." and then she eased her fingers well lubricated into my ass. Followed by the strap on that we had named big Ben.

More later
 
The kinkiest thing that I recall doing when I first started exploring sexually happened when I got to my first overseas assignment… translation…. Far from any watching eyes. Nothing was off limits and I went for it!
Two of my favorite men in the world lived in the dorm right across from mine. They were roomies. We shared a lot of long winter nights playing cards, listening to music, and drinking.
One particular night we were getting pretty crazy, and our card game turned into Spin the Bottle. I remember I was the first person to lose all of my clothes, and this just turned me on so much, being naked in front of two very hot and semi dressed men, who were sporting two of the biggest hard on’s I remember seeing. My friend Ben came up behind me and began kissing my neck and caressing my breasts… pinching my nipples just the right amount, to make me even juicier than I was already. Kellan approached me from the front, and immediately began to simultaneously French kiss me and finger fuck my pussy. I was literally gyrating on his hand, and he wrapped my legs around his waist while I leaned back against Ben, and slid his gorgeous hard 9 inch cock into my tight pussy. The stroking was intense and Ben squeezed my nipples while Kellan fucked me harder than I have ever been fucked before. He pounded me to the hilt and threw his head back and let out a yell that was heard on both floors of that dorm. No guessing what we were about in that room.
After Kellan emptied himself inside of me, he set my legs back on the floor. Ben turned me around and said “now it’s my turn.” He led me to the bed and I said I wanted him to fuck me from behind. I LOVE that position, especially if my head is on the bed and my ass is way up in the air… Ben was more than happy to do that. I climbed up on the bed, spread my knees wide and offered him my open and wet pussy and ass. He leaned over and began to lick me… I quivered with excitement and sensitivity… my fucking from Kellan had only whet my appetite and had made me so horny that I could have come with the air blowing across my clit. I moaned low and long and begged him to fuck me… He slid his thumb into my ass, and stimulated me like that for a while and soon after, my clit was coming all over him… my pussy clenching, he slid his steel hard cock deep inside of me and set me off on a roller coaster of orgasms that lasted the whole fucking….
It was a long cold winter night that night. We spent the rest of the night with me switching back and forth between the two of them… I loved each and every position we tried. I think when I was hanging off the top bunk and Kellan fucked me hanging on to my spread legs, that was pretty intense. The oral sex was so fantastic, it would set off an episode of fucking that had all of us wrung out dry by the morning. It was hot and sexy to be sleeping with both of them, but not together. Ben and Kellan were straight. They just had learned how to share and play nice..
To this day, I still can recall that night with them… and it still has the power to make me come just reliving it and especially now, writing it down… :devil:
 
The kinkiest thing that I recall doing when I first started exploring sexually happened when I got to my first overseas assignment… translation…. Far from any watching eyes. Nothing was off limits and I went for it!
Two of my favorite men in the world lived in the dorm right across from mine. They were roomies. We shared a lot of long winter nights playing cards, listening to music, and drinking.
One particular night we were getting pretty crazy, and our card game turned into Spin the Bottle. I remember I was the first person to lose all of my clothes, and this just turned me on so much, being naked in front of two very hot and semi dressed men, who were sporting two of the biggest hard on’s I remember seeing. My friend Ben came up behind me and began kissing my neck and caressing my breasts… pinching my nipples just the right amount, to make me even juicier than I was already. Kellan approached me from the front, and immediately began to simultaneously French kiss me and finger fuck my pussy. I was literally gyrating on his hand, and he wrapped my legs around his waist while I leaned back against Ben, and slid his gorgeous hard 9 inch cock into my tight pussy. The stroking was intense and Ben squeezed my nipples while Kellan fucked me harder than I have ever been fucked before. He pounded me to the hilt and threw his head back and let out a yell that was heard on both floors of that dorm. No guessing what we were about in that room.
After Kellan emptied himself inside of me, he set my legs back on the floor. Ben turned me around and said “now it’s my turn.” He led me to the bed and I said I wanted him to fuck me from behind. I LOVE that position, especially if my head is on the bed and my ass is way up in the air… Ben was more than happy to do that. I climbed up on the bed, spread my knees wide and offered him my open and wet pussy and ass. He leaned over and began to lick me… I quivered with excitement and sensitivity… my fucking from Kellan had only whet my appetite and had made me so horny that I could have come with the air blowing across my clit. I moaned low and long and begged him to fuck me… He slid his thumb into my ass, and stimulated me like that for a while and soon after, my clit was coming all over him… my pussy clenching, he slid his steel hard cock deep inside of me and set me off on a roller coaster of orgasms that lasted the whole fucking….
It was a long cold winter night that night. We spent the rest of the night with me switching back and forth between the two of them… I loved each and every position we tried. I think when I was hanging off the top bunk and Kellan fucked me hanging on to my spread legs, that was pretty intense. The oral sex was so fantastic, it would set off an episode of fucking that had all of us wrung out dry by the morning. It was hot and sexy to be sleeping with both of them, but not together. Ben and Kellan were straight. They just had learned how to share and play nice..
To this day, I still can recall that night with them… and it still has the power to make me come just reliving it and especially now, writing it down… :devil:

Wow, that is an incredible story, you should think about writing it up. Amazing, thank you for sharing.
 
The way this year started (described in Post #465), the whole year promised to be kinky. But I've only had sex with my husband since New Year's Day. What happened today may change that.

I met a couple of college kids (brothers) on Spring Break. They messed up and have nowhere to sleep except their car. I invited them to stay with us for the rest of the week.:devil:

Things started off innocent. I met them at Walmart. Most breakers buy lots of beer, candy, and pizzas or microwave food. These kids standing in line had four cases of beer and two blankets - no food. That's when I struck up a conversation and learned their predicament.

They are terribly polite and well mannered. They insisted on giving us money for the food we've prepared for them since they had money for lodging they couldn't get. They're gone most of the day except today because it rained.

They're so young, I didn't believe the one was old enough for college so I checked his ID. He's eighteen alright; not old enough to drink the beer his brother bought for him but that's not my concern. His older brother (claims to be twenty-two) is doable but the young one scares me. He is so baby faced and has so little pubic hair.
 
ROTFLMFAO. I bet you even blushed :eek:)

No, I handed him a towel. :D

It would be fun to give the whole story in one line answers but I won't. I wanted to disclose this experience, but at the same time I don't. I could get flamed, a grandmotherly woman corrupting a young man. [ Chargergirl, this young man is 18, I checked his ID ]

Hubby and I went for an early walk instead of a long bike ride because we knew the rain was coming. The kids went to the beach anyway. They're here for spring break and that means drink.

Hubby and I went shopping just as the rain came. College kids don't care, they stay out in it. We were playing Cribbage when they came home, wasted from their barley-brew lunch, they're clothes soaked. The Beach Patrol chased everyone off because of lightning. We offered to wash/dry their clothes.

The oldest showered first. He called out that his brother would need a towel. I went to get some from our closet. I expected to hand one thru the door but by the time I got there, I could see the older one passed out, face down on the bed, wrapped in a bath towel.

I thought I'd slip into the bathroom and leave the towels before the younger one finished but my timing was perfect. :eek:

I'm not shy and a voyeur, so I looked right at his cock. Then I handed him a towel. Noticeably drunk, he slurred, "Thanks." He started drying his hair but stood there with his cock waving around, watching me watch it.

I turned around and closed the door. When I turned back, he grinned and nearly fell, stumbling out of the tub. How do you catch a naked drunk? He kind of leaned into me so I just propped him up.

He was dripping all over my flour so I grabbed another towel and helped dry him off. I was doing his legs when his cock hit my face (deliberately, I bet). His cock looked painfully hard. I didn't even look up at him. I grabbed his cock and put it in my mouth. He came in 10 seconds.

I picked up his clothes. I went into the bedroom to get the older one's clothes (I tried to peek under his towel but nothing showed.) I started a load of laundry and then went back to playing cards with my husband.
 
hi

My ex bf and I watched stealth, his dad and mom do anal sex. We were so horny after watching,he did me threetimes anal that night.
 
That's a great idea! With my customer service experience, let's pitch it on Shark Tank together! :D

Why are we always getting involved in business ventures together? Wasn't I going to be your social secretary at one time? (Collecting fees at the door I remember)
 
No, I handed him a towel. :D

It would be fun to give the whole story in one line answers but I won't. I wanted to disclose this experience, but at the same time I don't. I could get flamed, a grandmotherly woman corrupting a young man. [ Chargergirl, this young man is 18, I checked his ID ]

Hubby and I went for an early walk instead of a long bike ride because we knew the rain was coming. The kids went to the beach anyway. They're here for spring break and that means drink.

Hubby and I went shopping just as the rain came. College kids don't care, they stay out in it. We were playing Cribbage when they came home, wasted from their barley-brew lunch, they're clothes soaked. The Beach Patrol chased everyone off because of lightning. We offered to wash/dry their clothes.

The oldest showered first. He called out that his brother would need a towel. I went to get some from our closet. I expected to hand one thru the door but by the time I got there, I could see the older one passed out, face down on the bed, wrapped in a bath towel.

I thought I'd slip into the bathroom and leave the towels before the younger one finished but my timing was perfect. :eek:

I'm not shy and a voyeur, so I looked right at his cock. Then I handed him a towel. Noticeably drunk, he slurred, "Thanks." He started drying his hair but stood there with his cock waving around, watching me watch it.

I turned around and closed the door. When I turned back, he grinned and nearly fell, stumbling out of the tub. How do you catch a naked drunk? He kind of leaned into me so I just propped him up.

He was dripping all over my flour so I grabbed another towel and helped dry him off. I was doing his legs when his cock hit my face (deliberately, I bet). His cock looked painfully hard. I didn't even look up at him. I grabbed his cock and put it in my mouth. He came in 10 seconds.

I picked up his clothes. I went into the bedroom to get the older one's clothes (I tried to peek under his towel but nothing showed.) I started a load of laundry and then went back to playing cards with my husband.

Loved it Sandra, thanks for sharing.
Yes, a B&B with BJ sounds an excellent idea. You should consider migrating to New Zealand, such enterprises are lawful here, in fact you'd probably be eligible for a Govt grant.
 
Kinkiest experience that wasn't

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.
 
Status
Not open for further replies.
Back
Top