What's your craziest sexual experience thread?
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Rajaah
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That's funny, I went to my hometown for a few days recently and while I was there I saw two different girls I used to date (coincidentally, wasn't there to see anyone). One of them is a blimp now and has a kid. The other one is in great shape and hotter than before, but married now. So I guess it can go in all different directions. Either way I know what you mean about the additional acquisitions when you see an old GF.
Also I once got caught boning in a tent during a get-away with a bunch of folks, sort of. Someone was rustling around outside our tent so we tried to keep it down, then the next day this guy who didn't like me was telling everyone about it (presumably it was him rustling around). My GF and I denied it. The whole thing was a bit creepy actually.
Caeden
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There’s one I see almost every time I’m in. She’s unbelievably cute even now with her being probably 39 or 40. But she went from Grade A spinner to really flabby in the past 20 years. I’d still watch her blow me. Not in front of her husband of course.
She’s also the only one I see if I go home that still flirts a little. I wish I’d totally sealed the deal rather than just spunking on her nose in a car.
Another I only kissed and fingered on an overnight school trip because she was too goodie to go further was flipping hot as fuck by the time we got out of college and still is milf material. I missed the boat on her. Dumped her for my ex and my ex, while cute, was starting to suffer from too much tanning skin and had started dying her hair blonde from brunette when we split at 30. At the time, my ex ran rings around her and was fun to toss around.
Rajaah
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In the regret department, I left a pretty great girl to get back with my ex. A couple years later it didn't work out (again) and I tried to reconnect with the girl I missed the boat on, only to discover I was blocked by her on Facebook which probably means "stay away, don't bother". Or maybe not? I don't know because I didn't ask.
And speaking of school, I've got another regret: I had a massive crush on a girl in 4th/5th/6th grade. Massive. Maybe my first crush. She looks like Linda Hamilton in the first Terminator, did then, still does now. I never told her that I liked her, though I did go out of my way to be around her like a beta orbiter. In 5th grade I had a birthday party and invited the whole class. She showed up, and when she was there she indicated that she...liked me. I mean, no uncertain terms, thought I was cute and wanted to tell me on my birthday. I basically told her to F off with that nonsense and walked away. What the fuck?
...I was a total idiot in the past, I think this thread has determined that.
It gets better though. I kept having a crush on her for the rest of elementary school but she avoided me after I was mean to her, then I didn't see her anymore after that. I didn't regret this too much because over the years, people told me that "relationships from elementary school never last anyway"
I looked her up on Facebook and talked to her there. Apologized for being mean to her and she barely remembered it. She's still a super hot MILF at 36 and is now married to... drumroll... another guy from our class who she started dating over the summer after 6th grade ended. She asked him out on the last day of school and he wasn't an asshole to her like I was, presumably. She said they were hot and heavy by high school and moved in together at 18 and it's been steady ever since. I eventually asked her to get a coffee with me and she stopped answering my messages. Really did just want to talk more but oh well.
Point is...it was like looking through a Butterfly Effect portal at what my life coulda been.
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Void
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Not quite the same thing, but before I decided to shave my head (mid 20's) I used to get my hair cut at the local Supercuts, and I always got "Cherry." I mean, I feel like that had to be her real name, because why fake it at a barber shop? Anyway, if you're a dude back before the age of cell phones you always put your arms on the arms of the chair, with your hands over the end sort of gripping it. Twice before I had experienced her putting her crotch right up on the top of my hands (under the bib thing though) almost the entire haircut, so this time I figured I'd go palms up. And she was wearing a skirt this time as well, so there's absolutely no way she wouldn't notice that it was my fingers and not the arm of the chair.
Three funny things happened that day. First, she was quite obviously beginning to show being pregnant, but I was terrified of asking and being wrong, so I completely ignored it the entire visit. She probably thought I was retarded. Second, she ground it out on my upturned fingertips so hard that it was actually kind of painful (the arm of the chair was metal). Third, when I'm contemplating whether or not I ask her out, despite her being pregnant, because I figure maybe she's DTF from the raging hormones...a guy comes in while she's doing my cut and gets introduced as her fiance. While she's squatting on top of my hand with her twat. It was under the sheet so you couldn't see, obviously, but if you thought about it for a second you'd have to see that my arms were up and had to be somewhere near her cooter. I was probably imagining it, but it felt like she got a little extra hitch in her giddyup, so to speak, from having him there while she did it. I'll admit, I was too much of a pussy to do much more than wiggle my fingers a little, even before dude showed up. Not that I thought I could get all up in there somehow, but yeah, I mostly froze.
Of course it did nothing but give me a raging boner with no relief, which was awkward when I had to stand up, and I'm positive she didn't climax either, but I could definitely feel that drenched pussy through all 3 layers (panties, skirt, bib), and it was fortunate she had a busy print on her skirt because I'm sure there would have been a noticeable wet spot otherwise. Of course I tipped her bigly.
Went back once more, they told me she had moved, and then I started shaving my head soon after and didn't need a barber, so I have no idea what happened to Cherry.
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This story doesn't belong here but it involves a barber shop, sorry for the derail.
Back when I was around 10 or so my brother and I went to a local barber shop ran by some really nice old dude. His buddies would always come in to hang out and what I soon found out was they also came to look at porn. The barber had a ton of playboys lying around the waiting area and these guys would just sit around chatting while starring at titties. So naturally I was curious and wanted to steal one for research. My bro and I devised a plan to grab one of the magazines and toss it into a backpack while he wasnt looking. Sure enough we got caught. Dude just said we were too young for them and put them all away. That's my pathetic non crazy story, my apologies.
Back when I was around 10 or so my brother and I went to a local barber shop ran by some really nice old dude. His buddies would always come in to hang out and what I soon found out was they also came to look at porn. The barber had a ton of playboys lying around the waiting area and these guys would just sit around chatting while starring at titties. So naturally I was curious and wanted to steal one for research. My bro and I devised a plan to grab one of the magazines and toss it into a backpack while he wasnt looking. Sure enough we got caught. Dude just said we were too young for them and put them all away. That's my pathetic non crazy story, my apologies.
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I was on vacation with my parents, we were staying in one of those shittier hotels with two beds in one room. I was 17, horny as fuck. Wokeup early AM from a sex dream and started jerking it, rolled off the bed to finish off and shoot my load on the hotel room floor. Finished, then went to climb back in bed and saw my dad was sitting by the door of the hotel, awake, reading news paper. He did not see me, but holy fuck awkward.
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Caeden
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oh god
I may have told this story here but I had a very odd experience with the girl that swore I knocked her up. We were screwing in a bed in her house. Supposedly home alone. Her older sister burst into the room (no door locks). I was ready to pop. I jumped off her and rolled over but it was too late. Her sister screams. My gf screams. And my dick pops off and I try to catch it. I hear an “oh my god” and her sister runs away. My gf chases after her to stop her from tellng on us. Very backward christian family with a few over 20 girls that were still virgins. Poor dad had almost all girls.
I just wiped the cum on the bed sheet.
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Rajaah
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I once went over to see a girl on Halloween when her parents were out and she was home alone. Midway through an uncharacteristically loud boinking session, we heard noises downstairs and realized they were home early. She stopped me and made me get dressed really fast because apparently she wasn't allowed to have me over for some reason. As she was ushering me out of the house we saw her parents standing in front of the door glaring at me. They didn't say anything, just glared. She and I didn't last much longer after that. Still don't know what the fuck was going on in that family.
SeanDoe1z1
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One girl back in HS (AIM days) was desperately trying to get me to sneak into her place and fuck her. Actually semi-proud of myself on this one...
I didn't go.
Why? Not because she wasn't hot, 10/10 chick that I probably would of blew my load over and over. I didn't because she was living at her uncles / aunt out of her home state because she was shipped off to stay out of trouble.
The dude was a US marshal, home, and no doubt would of fucking owned me trying to sneak into his house. A little bit of survival instincts there.
inb4 faggot
i dont have anymore crazy stories, i'm boring white bread. definitely saw and heard of a lot trains in the military, dont let your daughters join up.
I didn't go.
Why? Not because she wasn't hot, 10/10 chick that I probably would of blew my load over and over. I didn't because she was living at her uncles / aunt out of her home state because she was shipped off to stay out of trouble.
The dude was a US marshal, home, and no doubt would of fucking owned me trying to sneak into his house. A little bit of survival instincts there.
inb4 faggot
i dont have anymore crazy stories, i'm boring white bread. definitely saw and heard of a lot trains in the military, dont let your daughters join up.
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I may have told this story
GF in high school. One day my mom was supposed to be at work. Her bathroom had the shower in a separate little room, it was a stand up and had a built in bench. We spent a pretty long time in their. Apparently my mom came home in the middle, started to walk into the bathroom and saw our clothes in the outer room and walked away, then spent 10 minutes calling my name to get me to realize. Which of course I couldn't hear with the shower running and face between gfs legs. When I realized all I could do was laugh. My Mom couldn't even tell at me because I just kept laughing about it
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Izo
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Could she be the one? The one whom actually likes dick pics and is not shy about it. The unicorn.
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Izo
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Onoes
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Ohh man, that reminds me of a story! So I'm 15 and have been dating a girl for 6 months, my first real serious girlfriend. We end up having sex on my 16th birthday (I bought her a ring and proposed to her right after because I was a fucking idiot and thought we were soulmates) and we both loved it and were like "We should do this ALL THE TIME!". The only problem was, my parents were super conservative, she wasn't even allowed to come to my house unless my parents were there, and even then, living room only. Her mom was cool, but her dad was this cowboy up manly dude. Always had boots and a cowboy hat, handlebar mustache , pistol on his hip, the whole thing. I think he was a realtor or something, but he wanted it known he was a bad ass cowboy.
Anyway, she lives maybe 3 miles from me, and so what I would do was wait for them to go to bed around 10:30-11, go out my bedroom window, ride my bike to her house, climb in her bedroom window (removing and replacing window screens at both houses lol) and we would make out/fool around until 3-4am, and then do it all again to go home. I was getting like 1-2 hours of sleep on most days. The other factor was that she had a twin sister who was her opposite (my gf was the bad one, her sister was a bookworm) and they shared a room. So, her sister basically hated us, and when I came over she would put a pillow on her head, and occasionally bitch at us if we kept her up and pissed her off. About 95% of the time we would just make out, do hand stuff, and some oral, she was super hesitant to have sex with her sister like 8 feet away, but occasionally we would, and just try to keep it quiet.
So, one night, we can't help ourselves, and start fucking... and keep fucking... and fucking. For some reason I just couldn't get there, and we were at it for a couple of hours, and her sister was very aware and pissed off, we were both drenched in sweat and I'm sure the room reeked of sex. All of the sudden we see the kitchen lights turn on outside their room (just around the closed door frame) and we panic. I jump out of her bed and tiptoe/run butt naked past her sister and into her closet. A second later her bedroom light turns on. I hear her dad go "Whats going on in here? I heard something!" and my girlfriend is pretending like she just woke up like "Uhhh what? I think I was having a nightmare." and he just doesn't buy it and starts asking her sister what is going on.
This is the point I realize that my shoes, and all of my clothes, are on the floor next to her bed. Was pretty sure I was going to die. He was going to see my stuff, or her sister was going to crack, or he may look outside and find my bike. Then out of nowhere the nerdy sister screams "DAD! GO TO BED! I've been trying to sleep for hours and she keeps moaning in her sleep and now your in here with the lights on and I'm going to kill both of you! BOTH OF YOU SHUT UP AND LET ME SLEEP!!!"
And it's silent, followed by their light clicking off and the door closing and several more minutes of silence before I peek out, and my gf is just crying in her bed, and her sister said something like "Get the fuck out of here and if you ever do this shit again I'm telling him everything". I got dressed and slunk out of there. We broke up a couple of weeks later over dumb shit.
I think that was the last time we had sex, but maybe its just the most memorable.
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This isn't something I did, but I did watch it happen. I once watched an entire country spend 5 months mask debating. They were doing it in stores, on TV, even in churches.
That was freaky as shit.
That was freaky as shit.
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Izo
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Caeden
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So you laugh but a nurse I dated right before meeting my wife loved a dick pic. But only if it had cum running down it. I obliged once. I owed her one. She was the one that let me cum in her mouth after fucking her on some trails on the Blue Ridge Parkway. To this day the one and only dick pic I’ve ever sent. That was after our phone sex session I think I mentioned in this thread. She was working as a travel nurse admin and had a private office and fingered herself for me on the phone. This was right around when FaceTime first came out I think.
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