People Shared Stories Of Their Best/Worst Sexual Encounters And This Is A Roller Coaster WIN And FAIL

by 1 year ago

Shutterstock / Markevich Maria

I can’t really put my finger on why it’s so interesting to read about the sexual debacles and conquests of others, but then again it took me half a lifetime to find the g-spot. Below, a ton of people shared their stories of the best and worst sexual encounters they’ve ever had and I wouldn’t say that this is ‘fun for the whole family’, if you get my drift, but these are pretty spectacular. Obviously, due to the nature of these stories some of them might be considered slightly NSFW so if you’re not up for reading that then head out now (via AskReddit)

Best: First time wife and I tried anal.
Worst: The second time we tried.
Anal is off the menu now.

Best: First time my wife and I ever came simultaneously.
Worst: I hooked up with a girl at a friend’s wedding. I was going slow and kind of working it in when she says “just go in as far as you can”. So I press my pelvis against hers, she trembles, holds me there a second, and then lets out a tiny gasp and then goes noticeably limp. She then says “What, you can’t cum?” “…What?” “Did you not get off?” “… Well, we just started and-” As she is kicking me off of her “Well, I guess I just know what I like. You can take care yourself now, right?”
I have never been with anyone so selfish. It’s how I imagined most girls in my highschool felt. 30 seconds and the whole thing was over. The most disappointing part was; she was soooooo hot.

Was in the hot tub with girlfriend. She sits on my lap and I manage to get my shorts down enough and her swimsuit aside enough to achieve penetration. Her mum come out to see us and sits down to talk while my girlfriend is “sitting on my lap”.
I splooged inside my girlfriend while looking at and talking to her mum.

Best: With a former classmate, nearly ten years after graduating and it was rushed and rough.. awesome.
Worst: Found out that he lived with his mom so we had sex while parked along a deserted road. Well, attempted to but his truck was rather small for both of us so he opened the passenger door and long story short.. I fell out head first..

Best: having sex right after going to the strip club together, it was pretty awesome.
Worst: last time I had sex with my ex, it was awkward and felt so forced.

This one’s a bit long but worth the read.

I actually have a singular best/worst sexual encounter.
My friends and I threw a kegger in the woods near our houses when everyone was home for Thanksgiving our first year at college. When the party was dwindling down it was just me, my friend, his gf, and her friend who will be referred to as Becky. Becky was a bit of a shit show but it didn’t stop her from having a good time. We walked back to get the keg and out of nowhere she pushed me against a dirt mound and started sucking me off. She’s clearly not 100% right upstairs, as most of my bud’s girl’s friends are, but I’m not complaining. I’m obviously having it. She then starts taking off her clothes trying to bang right then and there with our friends not 50 feet away without a condom. I’m obviously not having it. She lives a couple blocks away so I convince her that we just go there.
We get up to her room and pick right up where we left off. Becky was incredible. Easily one of the best lays in my life. She was the perfect sexual combination of a little bit chubby and a lotta bit crazy. We got done and laid there for a while trying to recollect what just happened before I got some weird grumbling in my nether regions. Oh yeah…yup…yup. I need to shit. Becky, being the cool gal she was showed me to the bathroom with no judgement. I said thanks, walked in, closed the door, and did my duty.
That’s when the doorknob turned.
Becky walked right in and starts watching me shit, giggling as she locked the door behind her. WHATTHEFUCK. I politely ask her “What the fuck are you doing?” and she just kept giggling, staring at me. Whatever. I take my time to finish while my poo-fetish voyeur is enjoying the show. I finish wiping and get up to leave and she digs her claws into my arm (I had marks for a few weeks) saying “NO STAY! It’s my turn!” I told her I was just going to get some clothes on since they were in the other room. For some reason she obliged and let me leave.
The moment the door closed behind me I bolted to the bedroom, throwing on every piece of clothing I can uncover. I can’t find my boxers but fuck it I’m out of here. Underwear is just extra weight at this point. As I run past the bathroom I hear the door latch go but I have no time. I don’t want to see how deep this rabbit hole goes. I hear a desperate “WAAAAAAIIIIIIIT!” and scurrying footsteps following me as a burst out the back door. I run down the street and dart into a driveway to hide in case she is still behind me. I wait there for a while panting from fear and adrenaline before realizing she’s not coming. I did it. I’m safe but it’s 3 am and now I have to walk 3 miles home. Fuck. At least I found my boxers lodged in my jeans so I managed to leave no man behind.
Later, she made sure to tell her friends that I was a dick and ditched her. When they attacked me for being a prick, I made sure to let them know about her little fetish and suddenly they weren’t so mad.
Good times.
TL;DR: Girls with weird fetishes have at least mastered the more conventional aspects of sex.

Best: waking up to a middle-of-the-night BJ
Worst: the sewage smell coming from one girl’s ass.

Worst that I can remember. Was having sex with my ex on the couch. I was seated and she was straddling me facing me. Thing is our couch was a hide-a-bed and I’d slid down so that my ass was pretty close the the edge. As she kept rocking back and forth, the cushion under my ass kept shifting, too. Before long the positions lined up just the wrong way and my balls slid off the front of the cushion and when we rocked forward again they got caught between the front of the cushion and the front wall of the hide-a-bed. Difficult to explain in words if you haven’t really seen old hide-a-bed couches. It hurt, but not so bad that I didn’t try to recover and keep going. But with every stroke they just got grabbed and squeezed again. Just couldn’t keep going. Shifting required explanation, explanation provoked laughing from both of us and sexy times were momentarily postponed while our sense of humor and my balls recovered.
TL:DR Couch ate my balls

Worst: He had talked himself up so much (that should have been my first clue), and then come time to actually have sexy times he had the worst breath I’ve ever smelled, he had horrible body odor (even though he’d just taken a shower), he kissed like he was an oxygen mask (whole mouth over almost my nose and mouth and he kept licking me), then he couldn’t get it up to fuck me, and when he finally managed to get it up, he apparently started thinking about his ex girlfriend and started sobbing. Never again.

Girl had a shallow vagina, and sex was awful so I decide to at least go down on her. We had just ate sushi and I guess the liquor in my belly wasn’t settling right. I get down to do my business, and it is hands down the stinkiest stank I’ve ever smelled. I hold my breath and dive in (the gentleman’s move). It smells so bad, and the sushi/whisky combo was so unsettling, I threw up in my mouth, quietly spit it onto the floor under her bed, and kept on going…

Worst: Guy was 25, admitted he was a virgin casually while nearly being undressed. Didn’t judge him. Didn’t judge him at all. Then he proceeded to get undressed. He had the tiniest dick. Started to feel really really bad for this guy honestly. But we still shared the bed, tried to make his first time worth it. Wasn’t good for me at all, he went down on there between my legs at one point like a fatty on a free buffet, but you know, it was his first time, we managed. Then the next morning he ran out, told me I was cheaper than a whore cause he fucked me for free. Pretty rich coming from a tiny dicked 25 year old virgin.

Worst: This weird german girl I brought home who kept trying to bite my nose and then texted me the next day accusing me of stealing her phone. FROM HER FUCKING PHONE!

My worst was losing my virginity on the beach. I was 16 and met this girl in an AOL chatroom. I picked her up in my AMC Eagle and, I hate to sound judgmental, she didn’t exactly look the way she had described (kind of like if you thought you were getting a VW Bug and got a VW Bus instead). But I was 16 and wanted to get rid of my virginity like it was a boil on my ass, so off we went.
Anyhoo, sex on a beach sounds like a good idea until you actually try it. Sand gets into places where sand does not belong, you can catch more than one type of crab, and even if it’s dark out you still run the risk of getting caught which makes you paranoid. All of those things were racing through my young virgin mind as I was gyrating terribly for about 30 seconds on top of this poor girl. I farted when I came all over her. It was awful.
We went to the same high school, but completely different social circles. After we banged, I felt so ashamed of the whole situation I vowed to avoid her at all costs. Not the most mature decision, but hey, I was a dumb 16 year old. Add to that, she had mentioned that she was really into Wicca and when I stopped talking to her she got mad and sent me an IM that she had put a curse on me. My life has been in a downward spiral ever since. Never lose your virginity to a witch on the beach.


Using the opposite hand feels so alien to me

Bros, these best/worst stories over on Reddit keep going on and on and on. If you want to read them all in the AskReddit thread you can click HERE to keep heading on down the rabbit hole.

TAGSAskRedditBest and WorstSexsex stories

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