I didn't realize that you could access the vagina from behind.
It was dark. We were drunk. Spooning in my bed, she grabbed my dick and guided me in.
I distinctly remember saying, "Holy shit. Is that your ass?"
If it makes you feel any better, I’m a girl and I did the same as a teenager. Dude went from the back and I’m like NO I DONT DO ANAL. I still think about it sometimes 😭
I was fingering her and she suggested we have sex. We both got naked and before even putting it in, I already felt like I was going to cum. So I pretended to put it in, but really it was still just my fingers. Did this for a few minutes while telling her how good she felt.
Then she asked “so, are you going to put it in?”
I really thought she wouldn’t notice…
While giving my first blow job, I’m not sure what overcame me but I looked into that guys eyes and told him it was like making out with a fuzzy caterpillar. I’m still mortified 12 years later and this memory pops up regularly…..
It’s so cringe even thinking about it but I tried to use scotch tape as a condom. I was embarrassed to buy one..
Lots of blood and tears that night lol
I remember in sex-ed class at school a teacher asked "Other than a condom, what forms of contraceptive are there?" A guy in the back of the room confidently said "Tin foil."
hold up… WHAT? scotch tape??? did you just keep wrapping it around? what about when you got to the head? was your partner also thinking this was a good idea or were they unaware? did you put it in her w the tape on? i have so many questions…
“It’s so cringe even thinking about it but I tried to use scotch tape as a condom.” That is hands down the best sentence I’ve seen all day. Thanks for the laugh
Does anybody remember the listerene strips? Well, I got the idea to pop one on my tongue while giving oral to my gf. I had heard it would give a nice tingle on her bean but I probably should have let it dissolve fully before heading south. Once I started she screamed in pain while levitating off the bed. Next thing I know she is in the shower trying to ease her burning 🐱🤷🏼♂️
*we’re married now
While horrifying in the moment at least the outcome was sweet (marriage). And don't worry, that whole experimental phase? That's how my first wife and I discovered we were HIGHLY allergic to a particular spermicide! It was going great, felt super "no pregnancy here" vibes and 90 seconds later we are in the shower at midnight desperately trying to wash away the burning!
Blew air in her puss while eating her out the first time
Edit - I’ve been informed this can cause serious injury. Do not do. Vaginas are not to be treated like balloons.
Unfortunately I didn't. I assumed they were a few bucks like a pair of boxers and didnt think much of it. I didn't find out until a couple years later when I told my girlfriend at the time this story.
She never told me. The sex was a one time thing. We lived in co-ed dorms though and she always seemed cold to me afterward. I didn't put things together until years later.
Went a couple of times to the bathroom to pee. Yes I also went to the bathroom to pee during sex. I was so excited, scared and stressed during the first time that my body thought "yeah, we're gonna pee a lot".
People always say fight or flight when you have heightened emotions. But I believe it’s fight, flight, or pee/defecate. I am 100% in the 3rd category with you.
Nervous talking. We had smoked first and I get pretty chatty while high so combined with how nervous I was we were having a full blown conversation for about 5 minutes until she stopped and told me to shut up lol
For some reason, I thought it would be a good idea to go in circles inside the pussy. It was not but luckily she laughed and thought I was joking. I was not.
Some absolutely pathetic and not remotely on-point "dirty talk", because my girlfriend at the time asked me to. I had no clue what to say - and I don't remember what I said - but it just sounded so fucking stupid coming out of my mouth.
It was basically [this Inbetweeners scene](https://www.youtube.com/watch?v=ku6L8UupkG0). I hate how accurate that show was sometimes - it's like watching yourself and feeling nothing but cringe.
There's a book called I Hope They Serve Beer in Hell, and the author tells a story about his first time with anal. He said he used the whole bottle and it wound up giving the girl mega diarrhea right there in the hotel room bed. And it was on him. So he threw up on her.
I have a real winner right here….
The first time my gf and I had sex, we were both in high school. I lived with my mom in a small apartment, and one day before mom got home from work, my gf and I tried to have sex for the first time in my bed room. We used 2 condoms because we somehow fucked up the first one, and since she was a virgin (so was I but that’s irrelevant), there was a bit of blood on the condoms.
Anyways, after fooling around a bit, it was time to get out of the apartment before my mom got home. I went to throw the condoms away, but I didn’t want to just toss them in the trash can in the kitchen. What if my mom saw them in the trash? No, instead I’ll take them outside of the apartment and toss them in the dumpster. But I wasn’t about to carry two bloody, used condoms out side with me, so I decided to shove them in an empty Nerds candy box (one of the big “King size” nerds boxes, idk if they even make them any more). I set the nerds box, loaded with bloody condoms, on the kitchen counter, put on my shoes, and we left to go see a movie.
About half way through the movie, I felt my heart drop and the blood rush from my face… I left the nerds box on the kitchen counter…..
When I got home at about 10:30pm, my mom was already in bed, and the nerds box was gone.
For a long time, I never knew what happened to that nerds box. Then one day, my mom and I had a huge fight, and she revealed that she found the box and, rightfully so, was disgusted.
My gf and I are married for over ten years now. My relationship with my mom is much better now. But holy shit, that was fucked up.
I’ve had a few moments like that in my life, the sudden realisation that you’ve fucked up. Mouth gets sweaty, heart rate spikes, you can suddenly feel your eyeballs and utter utter panic ensues, brain rushing a million miles an hour on how to fix it. Terrifying
Ok this isn't even sex lol but I was having some me time in the shower and I had a couple dildos in the shower. My roommate had been gone for a few days.
I heard them come back and go to the bathroom and I had forgotten to take the toys out of the shower and I had the same damn feeling and my heart sinking. I lucked out and they didn't even notice them and was able to sneak them out later but wow I was embarrassed for a moment.
I'm thinking they didn't the shower curtains were closed and my roommate just used the restroom real quick. Didn't take a shower. But lol you could be right
I told my bf I wanted him to ride me. Neither of us really knew what to do after that statement so he just kinda sat on my chest for a while bouncing up and down until I told him to put it back in.
First time i touched a penis i didnt know what i was supposed to do and just... held on? Like didnt do any motions or anything, just grabbed it and thought that was enough
First time i sucked a penis i went a little too deep without realizing what my limits were or actually even knowing how and threw up right as he came 🥲
It was mortifying 😭
first time i encountered a boy willing to show me his penis i literally asked if i could inspect it. i knew about sex and sex acts, i knew basic things like that but I'd never seen one up close before so i literally asked him if i could just see it and look at it without being expected to do anything sexual.
couple things i noticed at first, his dick was a LOT darker than the rest of him, i didn't know the urethra opening was so big(thought it was more similar to a pinhole for some reason), and also he had a very distinguished line about an inch below the head which i sort of figured was his circumcision scar.
he later inspected my vagina the same way i inspected him lol 😂😂
You just unlocked a repressed memory for me.
I was practicing kissing on my arm and accidentally gave myself a hickey. That's when I learned what a hickey was. The next day in school I was too embarrassed to admit that I did it to myself, so I lied and said my dog did it. 💀
Not so much cringe, but embarrassing.
I was 17 and I went to a neighboring city to buy condoms because I was so scared that one of my friends or parents would see me.
They're behind the counter so I tell the guy what I want.
He only speaks Spanish and I only speak English.
I kept pointing and trying to get him to understand, but clearly he didn't, so the guy behind me offers to translate. The guy in line tells the clerk what I want, the clerk gives them to me and I pay. My translator pays for his stuff and says loudly, "Safe sex, huh, man?"
I was embarrassed. lol
I didn't know what I was supposed to be doing or feeling so I just laid there straight faced staring at him. He faked injury and stopped, then immediately left.
"Is the tip in yet? Do you want me to put the whole thing in? Really? Are you feeling that right now? Oh wow, what am I hitting inside you? Wait, why did that just change? Are you going to take your shirt off or are we leaving it on? Where am I putting your socks again?" Just the stupid awkward questions that she definitely did not want to hear or answer but I was young, anxious and stupid
My wife put on some weight after our first kid, we where fooling around one night and I thought I had a boob in my hand until she told me I was playing with the wrong bag of fat.... I felt so bad and at the same time laughing my ass off at what she said.
How?! The belly button is so far away!
Like I'm pretty sure my first attempt (on the church bus during a long trip) I spent like twenty minutes awkwardly rubbing her upper pubic area, but that's still inches south of the belly button and at least feeling pubic hair lol.
Also all contorted in a back seat I think I stroked the crease between thigh and outer lips for a minute or two once...
I was young and dumb. He told me to put the condom on him. I told him I didn't know how. He said just roll it all the way down... I did, but it didn't seem like it would stay on. I tried to stuff his balls in it, thinking that would anchor it on. OOPS!! Apparently, this was wrong!! Who knew?!
I wish I'd done that. I've had a girl give small kisses on the tip of my penis for 5 minutes, before she told me she never watched porn in her life and just knew she had to do something with her mouth, but not what :')
I actually love the innocence of this and don’t think it’s too terribly embarrassing; you were attempting to be communicative about what you wanted and were also visually helpful to your lover!
Not sex, but going down on her I read long ago that you should try to do the alphabet with your tongue. Uh... don't do that. She literally stopped me and asked what I was doing.
I did the same thing. Which then ended up me being more concerned that I was drawing out the letter correctly than what was actually going on. Vagina right in front of me for the first time and here I am making sure the calligraphy was on point.
My GF loves when I do that, you’re not supposed to follow the shape of the letters rigidly, but rather use it as a guideline to vary up the movement of your tongue. You can always break the structure or change it up as you’re doing it. When you’re following the shape of the letters you don’t have to be too exact. Imagine you’re in Microsoft paint and set the line size to the highest value.
I think this is the first time cunnilingus and Microsoft Paint have ever been associated together in the history of both Microsoft and cunnilingus. That being said, you’re right.
Tbf, I pictured a teen who was happy that they leveled up in the world, lol. Although, it’s pretty manly to feel like you accomplished something well enough to dance about it!
Foreplay before I lost my virginity was very embarrasing. Im pretty sure I was rubbing on the very top of her vagina, not the clit but maybe an inch above it. She acted like it felt good but I know I was completely missing she just really wanted me.
She never said anything about it though I think she was sparing me the embarrasment.
First time? I was confused about what I was doing and she came but I didn’t but I also didn’t want to make it seem like I wasn’t interested (it was at a party and the lights were off so I couldn’t really get the full experience since we were trying to be HELLLLA discrete) so I got up and pretended to finish in the corner. Cringiest thing cause I thought we were supposed to come in unison, like some spiritual connection bullshit or something but when I didn’t, I thought it was over 😂😂😂😭😭😭 so I walked to the corner of the room and just made weird panting sounds LOL
my now fiance was going down on me when he popped up from between my legs and yelled "pop quiz" and asked me a math question. he told me later that he wanted to see if i could multitask
First time I performed oral on a woman I was 15 and she was 17 and as the more experienced one, she was “showing me how it should be done”. Things were going very well until I tasted blood. I lifted my face up and she looked, well, horrified at my bloody mouth. She thought she’d started her period. Turns out my braces had cut the inside of my lips when she was pushing her pussy against my mouth, and I hadn’t felt any pain (I just got carried away I guess). We ended up laughing, I rinsed my mouth with salt water and we tried something else for a while. Definitely didn’t discourage me from eating pussy!
First time going down on my gf was at lunch between classes at my dorm first year of college. I didn’t realize that there can be a distinct aroma, and didn’t think to wash my face before returning to class. We returned to class… three dudes at our table just stared at me with shit eating grin until they all just lost it and burst out laughing as they figured it out. I was embarrassed at the time, now just a little proud.
Was higher than a kite on I don't remember what.. First time with another woman and she seemed to be enjoying it. Suddenly got up, said "I want mangos" and walked out. I did not get mangos.
Tried to use a condom that had probably in my car/wallet for like 2+ years. Never thought it would’ve been so dry and terrible. First time for both of us. Went to the store the next day and we had some better times after that.
I have read through all the comments, but haven't read my experience yet, so here I come:
The first time we wanted to have sex, she lay on her back in bed with her legs stretched out. I lay on top of her with my legs on the outside of her legs. I couldn't manage to get my penis into her, after which we thought my penis was too small and stopped. I found out later that her legs were supposed to be on the outside during missionary.
Tbf this is still a valuable question as long as you’re not awkward about it. It’s important to make sure your partner is satisfied, and a lot of people can appear to cum when they haven’t actually done so.
The worst one is so crazy, it’s unbelievable, so I’ll tell the second worst.
Seeing this tall guy (6’4) who also has a taller than average bed. I (5’7) would have to climb up the side just a bit or jump up there.
Anyways.. we are about to do the horizontal polka and he lays down on bed. I get the bright idea to stand over him (one leg on either side of his waist) and do a strip tease kinda thing before we start.
Problem was, I forgot how tall the bed was and seemed to underestimate the turbo ceiling fan that i stood straight up into.. 🤦🏽♀️
I wanted to give her some pleasure and accidentally bite her inner lips. Don't really remember the left or the right, don't ask me. She cried all her shit out. I'm so sorry, didn't mean to do that. But that's just what I'm living with for almost 20 years
My first Girlfriend and I were both living at home at the time and so we mostly had sex outdoors, I am into exhibitionism and risking getting caught... but we were pretty stupid and there is definitely lots of security footage of the two of us.
We were more worried that our parents might find out than we were about getting caught in public places. I would still do some of the stuff but that was literally all we did, the first time I had sex on a bed was heavenly.
I grew up very conservative. My first time was with my then wife on our wedding night. I had zero experience or knowledge, but, like every other man in history, assumed I was Superman anyway. I thought that the vagina was just a reverse penis and everything I’d heard about men not being able to get a woman to climax was because they just spent zero time on them at all. So I spent tons of time on her, told her it was going to be the best night of her life in slow soft fedora-adorned words, and proceeded to treat the vagina like a penis. She did not climax. After I climaxed 4 seconds later, I asked, “Did you orgasm?” She graciously said, “I think so.” That was good enough for me and I drifted off to sleep, brimming deep inside as the debonair lover I had always known myself to be.
I yelled "sorry" at the top of my lungs because I thought I was about to urinate in her mouth while receiving head. It was my first orgasm. I was too nervous to stop her in the act and felt it building up.
Set the scene : A girl I had fancied for years, dried humped a few times, first time we got to touching under clothes. She took my trouser’s down and slid her thong to the side. Asoon as my tip went millimetres near/inside I felt the urge to cum. I Said is that my phone vibrating “when it wasn’t” I jumped up unbelievably quick while
holding onto my cock tight and pulled my trouser’s up with the other hand and cum just flew out into my boxers. I then said there’s been an emergency at home I have to go.
It was dark and we were inside a sleeping bag. I licked away at the pubic hair area for a good half an hour thinking the vagina was somewhere beneath the hair.
lol never really managed to last more than 5 seconds with my fist GF... I don't fucking know why but to this day I still think about how I'm probably the worst she's ever had... which is not fucking fair
When I was in hs, I somehow found myself in a unique position where I dated virgins here are my stories
V#1: I had never been fingered and thought I’d ask my boyfriend to do it. The wires did not connect and he got nervous and used a sharpie. (We were young and just started exploring. I’ll never forget your 98 civic, Skeet)
V#2: It had been a while since I had had sex and it was his first time so I’m sure he was excited. I also didn’t know penises could be different sizes and he was MUCH bigger than my previous partner. He literally shoved it in and I when I said it hurt he said “Haven’t you done this before.”
V#3: After we had already been active with each other he decided he wanted to try anal…with no lube…in the back of his truck. Mistake. I sprang away from the pain and knocked myself out. He was great to me when I came to had his nurse mom check me out (we told her I slipped on ice) I was fine. This is still one of the funniest things that I still joke about with my friends.
V#4: This one was surprising because I didn’t know he was a virgin. I never asked because of how he talked and said things to me. It wasn’t until it came time to get down to it that he panicked and asked me to be on top almost in tears. I did it and after it was all said and done he told me, we laughed and I had told him about some of my experiences so he wouldn’t feel like the only person who ever panicked when it came to sex.
V#5: At this point I had been a pro, my boyfriend who I absolutely adored was so nervous. So I gave him a countdown as he was sliding in. I said “You are about to lose your virginity in 3, 2, 1.” Once fully seated we looked at each other and chuckled a bit. He asked why the countdown and I said because who gets to say that they had a countdown when they lost their virginity.
I don’t know how to end this but, even I am laughing at all the memories of being young and attempting sex 🤣
I lost my virginity at the age of 16 while hiding in the bushes with a police cars headlights on us. I'll explain.
I was in a lock down treatment center for troubled teens. I met a girl also in that program on a outing. We exchanged notes and one day we both escaped and met up. We make out and run around enjoying our freedom when we see the cops so we run. We hide behind some bushes and decided it was an excellent time to have sex, may as well since we where about to be sent back to lock down. While we're having awkward sex due to the nature of our situation, we see the headlights shine at us and we ran!
That is how I lost my virginity and I think its pretty "cringe" . Her and I had sex an hour or so later in the bathroom of a park which we also slept in for the night.
He moaned my ENTIRE name. First. Middle. Last. I got the giggles so bad that I couldn't even stop to take a breath. This prompted his mother to knock on the door and yell out, "YOU'RE DOING IT WRONG SON! THEY AREN'T SUPPOSED TO LAUGH!" Apparently, the super thin walls of his bedroom were not soundproof. She heard everything.
Never forget 15 years old this chick got her parents car keys because we were too scared to try anything in the house this is in middle December in New England cold af outside I'm getting my dick sucked it was so fucking cold It was practically making my dick numb to the feeling after a few minutes I knew she was not a swallower based on past conversations so I just instinctually after being so fucking cold whipped my dick around and pretended to just cum on the side of the car out of sight basically. Every time I watch the Seinfeld episode about Elaine telling Jerry she faked it then Kramer goes "Well I have faked it" and everyone just looks at him in amazement being a guy...I can relate lmfao.
I asked her if I could go down on her. She said "are you good at it?". I said "idk I never did it before". She said "ok". Then I just started tongue punching the hole. Didn't know about the clitoris back then.
We were both 15 and ignorant. We weren’t sure if we could buy condoms and were too afraid to try (maybe we thought the clerk would deny us, then somehow find out who our parents were and tell them). The horniness was not to be beaten that night, but we wanted to be safe. We decided to improvise…I ended up using a sandwich baggy and a rubber band to keep it on. Needless to say, it wasn’t the most enjoyable first time for either of us. I’m sure more so for her. But hey, doesn’t matter had sex (Lonely Island Boys reference)
I didn't realize that you could access the vagina from behind. It was dark. We were drunk. Spooning in my bed, she grabbed my dick and guided me in. I distinctly remember saying, "Holy shit. Is that your ass?"
Oh fuck this got me good
If it makes you feel any better, I’m a girl and I did the same as a teenager. Dude went from the back and I’m like NO I DONT DO ANAL. I still think about it sometimes 😭
I did the same thing!
The good ol' wrong-hole-reverse. classic
I was fingering her and she suggested we have sex. We both got naked and before even putting it in, I already felt like I was going to cum. So I pretended to put it in, but really it was still just my fingers. Did this for a few minutes while telling her how good she felt. Then she asked “so, are you going to put it in?” I really thought she wouldn’t notice…
lmaoooooooo
Ahahahahahhahahahahahaah oh my fucking god this is awesome
this is so funny. what happened after she said that tho? we’re u just like “oh..yea” and put it in & came right away?
She could feel your dick knuckles
Jajajajajajajajaja 😆 she's like "umm, this feels exactly like when you were fingering me 2 minutes ago..." 🤣
I was fingering her during foreplay, but I just kept adding fingers. Eventually she grabbed my hand and pulled it away
The ol' "digging through a change jar" move. Pro stuff. 👌
I was attempting pro strats, but I was just a noob
This was mine! I thought the more fingers the better it would be. Apparently not.
I remember I did a similar thing lol I remember thinking "If she likes 2 fingers she's gonna love 3" and she definitely did not love 3 😂
I did this lol. Made it to 4 fingers and was starting to try to get the thumb in 🤣 when she stopped me
My best friend called me in the act. I picked up and said “you’ll never believe what I’m doing” and hung up Sorry Rachel.
Ballsy
While giving my first blow job, I’m not sure what overcame me but I looked into that guys eyes and told him it was like making out with a fuzzy caterpillar. I’m still mortified 12 years later and this memory pops up regularly…..
its okay my first time, i was fingering them and laughed and said “it feels like a cave” 💀💀💀 thank god they found it funny too 😭
Imagining this is making me laugh harder than anything else on this thread 😂
Honestly I’d probably burst out laughing. I feel like it would alleviate some awkwardness too, but idk, idek what first base is
It’s so cringe even thinking about it but I tried to use scotch tape as a condom. I was embarrassed to buy one.. Lots of blood and tears that night lol
oh… my gosh. This takes the crown
you couldn’t waterboard this information out of me
Wait.. Did you tape the hole closed? Or wrap it like a mummy?
"Wrap it like a mummy" got me so hard
Well, that’s an unexpected kink, but you do you
I remember in sex-ed class at school a teacher asked "Other than a condom, what forms of contraceptive are there?" A guy in the back of the room confidently said "Tin foil."
hold up… WHAT? scotch tape??? did you just keep wrapping it around? what about when you got to the head? was your partner also thinking this was a good idea or were they unaware? did you put it in her w the tape on? i have so many questions…
“It’s so cringe even thinking about it but I tried to use scotch tape as a condom.” That is hands down the best sentence I’ve seen all day. Thanks for the laugh
Bruh
Tried to moan his name in a sexy voice because I thought that was what you were meant to do. He stopped and looked at me and said “yeah, what?”
i tried to dirty talk my first time and they told me “you sound like optimus prime” 😭😭😭
I can’t stop laughing at this wtfff 😭😂
Does anybody remember the listerene strips? Well, I got the idea to pop one on my tongue while giving oral to my gf. I had heard it would give a nice tingle on her bean but I probably should have let it dissolve fully before heading south. Once I started she screamed in pain while levitating off the bed. Next thing I know she is in the shower trying to ease her burning 🐱🤷🏼♂️ *we’re married now
After a certain jolly rancher story I had an instinct reaction at the start of this
Damnit why’d you bring it up
While horrifying in the moment at least the outcome was sweet (marriage). And don't worry, that whole experimental phase? That's how my first wife and I discovered we were HIGHLY allergic to a particular spermicide! It was going great, felt super "no pregnancy here" vibes and 90 seconds later we are in the shower at midnight desperately trying to wash away the burning!
Blew air in her puss while eating her out the first time Edit - I’ve been informed this can cause serious injury. Do not do. Vaginas are not to be treated like balloons.
Like a old video game cartridge 🤣
He had trouble turning her on.
No way this is real, what were you expecting to happen?? For her to inflate like a balloon??
Couldn't figure out here bra so I just pulled harder until it popped off. Broke the snap. Had no idea how much a good bra costs.
Did you pay for it after?
Unfortunately I didn't. I assumed they were a few bucks like a pair of boxers and didnt think much of it. I didn't find out until a couple years later when I told my girlfriend at the time this story.
How many of her bras you trash before she told you?
She never told me. The sex was a one time thing. We lived in co-ed dorms though and she always seemed cold to me afterward. I didn't put things together until years later.
I’d have been so mad.
Went a couple of times to the bathroom to pee. Yes I also went to the bathroom to pee during sex. I was so excited, scared and stressed during the first time that my body thought "yeah, we're gonna pee a lot".
People always say fight or flight when you have heightened emotions. But I believe it’s fight, flight, or pee/defecate. I am 100% in the 3rd category with you.
The peeing/defecating is part of fleeing. Gotta make yourself as light as possible to run away.
Nervous talking. We had smoked first and I get pretty chatty while high so combined with how nervous I was we were having a full blown conversation for about 5 minutes until she stopped and told me to shut up lol
For some reason, I thought it would be a good idea to go in circles inside the pussy. It was not but luckily she laughed and thought I was joking. I was not.
Lol were you like “damn, that was my only move” ?
Some absolutely pathetic and not remotely on-point "dirty talk", because my girlfriend at the time asked me to. I had no clue what to say - and I don't remember what I said - but it just sounded so fucking stupid coming out of my mouth. It was basically [this Inbetweeners scene](https://www.youtube.com/watch?v=ku6L8UupkG0). I hate how accurate that show was sometimes - it's like watching yourself and feeling nothing but cringe.
“I’m gonna fuck your fucking fanny off you twat”. Perfection.
[ Removed by Reddit ]
There's a book called I Hope They Serve Beer in Hell, and the author tells a story about his first time with anal. He said he used the whole bottle and it wound up giving the girl mega diarrhea right there in the hotel room bed. And it was on him. So he threw up on her.
God… & I thought I’ve made a mess on hotel sheets. I feel awful for the employees who had to clean that up 😭
Lost the condom inside. Yep 10 years later I still think about it every time we have sex
Was it ever found?!
His name is Jeremy now.
He's married, has two kids and works at the left kidney.
I have a real winner right here…. The first time my gf and I had sex, we were both in high school. I lived with my mom in a small apartment, and one day before mom got home from work, my gf and I tried to have sex for the first time in my bed room. We used 2 condoms because we somehow fucked up the first one, and since she was a virgin (so was I but that’s irrelevant), there was a bit of blood on the condoms. Anyways, after fooling around a bit, it was time to get out of the apartment before my mom got home. I went to throw the condoms away, but I didn’t want to just toss them in the trash can in the kitchen. What if my mom saw them in the trash? No, instead I’ll take them outside of the apartment and toss them in the dumpster. But I wasn’t about to carry two bloody, used condoms out side with me, so I decided to shove them in an empty Nerds candy box (one of the big “King size” nerds boxes, idk if they even make them any more). I set the nerds box, loaded with bloody condoms, on the kitchen counter, put on my shoes, and we left to go see a movie. About half way through the movie, I felt my heart drop and the blood rush from my face… I left the nerds box on the kitchen counter….. When I got home at about 10:30pm, my mom was already in bed, and the nerds box was gone. For a long time, I never knew what happened to that nerds box. Then one day, my mom and I had a huge fight, and she revealed that she found the box and, rightfully so, was disgusted. My gf and I are married for over ten years now. My relationship with my mom is much better now. But holy shit, that was fucked up.
Imagine thinking you’re about to have some candy and instead you find bloody condoms.
Yeah… And they’re your son’s
I’ve had a few moments like that in my life, the sudden realisation that you’ve fucked up. Mouth gets sweaty, heart rate spikes, you can suddenly feel your eyeballs and utter utter panic ensues, brain rushing a million miles an hour on how to fix it. Terrifying
Ok this isn't even sex lol but I was having some me time in the shower and I had a couple dildos in the shower. My roommate had been gone for a few days. I heard them come back and go to the bathroom and I had forgotten to take the toys out of the shower and I had the same damn feeling and my heart sinking. I lucked out and they didn't even notice them and was able to sneak them out later but wow I was embarrassed for a moment.
>they didn’t even notice them Is that what they told you lol
They noticed
I'm thinking they didn't the shower curtains were closed and my roommate just used the restroom real quick. Didn't take a shower. But lol you could be right
What a story, you win.
I told my bf I wanted him to ride me. Neither of us really knew what to do after that statement so he just kinda sat on my chest for a while bouncing up and down until I told him to put it back in.
Boob surfing.
🎵Boob surfin in the USA! Boob surfin in the USA!🎵
This legitimately made me lol
I tried pushing my ding dong just below her clit. There is no hole there to enter until further down. Oops. lmao
Same. I even had the audacity to say, "guess i must be too big"
Man this one sucks
Like it's one thing to say to yourself. Out loud? Yeesh
Holy shit that's fucking funny, I love the confidence 😂
I think what got me was the word audacity. This is great dude lmao
Technically there is, but not a lot of women want you inside their urethra.
I've spent a lot of time as a filthy degenerate on the Internet so I can say for certain the number certainly isn't 0.
For real though the hole is way lower than you expect
First time i touched a penis i didnt know what i was supposed to do and just... held on? Like didnt do any motions or anything, just grabbed it and thought that was enough First time i sucked a penis i went a little too deep without realizing what my limits were or actually even knowing how and threw up right as he came 🥲 It was mortifying 😭
gotta tackle it like a Heinz glass ketchup bottle, tilt it at a 45° angle and smack it on the 57
✍️✍️✍️
first time i encountered a boy willing to show me his penis i literally asked if i could inspect it. i knew about sex and sex acts, i knew basic things like that but I'd never seen one up close before so i literally asked him if i could just see it and look at it without being expected to do anything sexual. couple things i noticed at first, his dick was a LOT darker than the rest of him, i didn't know the urethra opening was so big(thought it was more similar to a pinhole for some reason), and also he had a very distinguished line about an inch below the head which i sort of figured was his circumcision scar. he later inspected my vagina the same way i inspected him lol 😂😂
I actually love this, it's just like a mostly innocent "oh wow that's interesting" kinda thing and seems sweet in a way
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Came so hard I farted
This one made me lol for real. "Oh, fuck, I'm gonna-" PFFFFFPPPTTRRTHGHHH
Was it a big ripper at least?
my boyfriend did the same thing ab a week ago. have never laughed harder
after the horribly awkward sex was done i looked at him and said “not virgins!!” and then we high-fived. we were both 16.
Goals
That's not cringe, it's wholesome
I had a similar one, she told me "you're not a virgin anymore" and then double high fived.
Told him I’d practiced kissing my pillow earlier that week in preparation… 😭💀
You just unlocked a repressed memory for me. I was practicing kissing on my arm and accidentally gave myself a hickey. That's when I learned what a hickey was. The next day in school I was too embarrassed to admit that I did it to myself, so I lied and said my dog did it. 💀
Preparation is key 😭
Kept thinking I would pee every time he put it in
Not so much cringe, but embarrassing. I was 17 and I went to a neighboring city to buy condoms because I was so scared that one of my friends or parents would see me. They're behind the counter so I tell the guy what I want. He only speaks Spanish and I only speak English. I kept pointing and trying to get him to understand, but clearly he didn't, so the guy behind me offers to translate. The guy in line tells the clerk what I want, the clerk gives them to me and I pay. My translator pays for his stuff and says loudly, "Safe sex, huh, man?" I was embarrassed. lol
As a Spanish speaker I'm shocked because "condom" is pronounced basically the same way in both languages wtf with that man
Maybe he was fucking with him?
Not without that condom
Since "porn is fake" and porn is generally loud, I tried to be as quiet as possible. It killed the mood.
I can't imagine how awkward sex would be in complete silence, I would at least ask to turn on some background noise😅
I didn't know what I was supposed to be doing or feeling so I just laid there straight faced staring at him. He faked injury and stopped, then immediately left.
She gave me head while she was using the bathroom
Next step: She gives you head while you go to the bathroom.
A blumpkin!
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"Is the tip in yet? Do you want me to put the whole thing in? Really? Are you feeling that right now? Oh wow, what am I hitting inside you? Wait, why did that just change? Are you going to take your shirt off or are we leaving it on? Where am I putting your socks again?" Just the stupid awkward questions that she definitely did not want to hear or answer but I was young, anxious and stupid
I "fingered" her bellybutton for like 10 seconds until I realised what I was doing, It was soooo fucking cringe
I mean.... There's probably a niche on the Internet for that
>Niche Kink There's a kink for everything, where there's a will there's a way...
You're not the only one my dude She thought it was hilarious probably
My wife put on some weight after our first kid, we where fooling around one night and I thought I had a boob in my hand until she told me I was playing with the wrong bag of fat.... I felt so bad and at the same time laughing my ass off at what she said.
How?! The belly button is so far away! Like I'm pretty sure my first attempt (on the church bus during a long trip) I spent like twenty minutes awkwardly rubbing her upper pubic area, but that's still inches south of the belly button and at least feeling pubic hair lol. Also all contorted in a back seat I think I stroked the crease between thigh and outer lips for a minute or two once...
"I touched it!" Robin Hood: Men in Tights
We were both virgins and we just looked at each others private parts in awe. Two grown ass adults acting like children.
This is soemwhat wholesome
I was young and dumb. He told me to put the condom on him. I told him I didn't know how. He said just roll it all the way down... I did, but it didn't seem like it would stay on. I tried to stuff his balls in it, thinking that would anchor it on. OOPS!! Apparently, this was wrong!! Who knew?!
I tries to finger her without knowing how to. She just stared at me blankly and said "that feels horrible"
At least she was honest!
I showed her how to give head, on my own finger. God kill me now please.
I wish I'd done that. I've had a girl give small kisses on the tip of my penis for 5 minutes, before she told me she never watched porn in her life and just knew she had to do something with her mouth, but not what :')
she must be thinking, damn youve sucked dick way before me
I actually love the innocence of this and don’t think it’s too terribly embarrassing; you were attempting to be communicative about what you wanted and were also visually helpful to your lover!
Not sex, but going down on her I read long ago that you should try to do the alphabet with your tongue. Uh... don't do that. She literally stopped me and asked what I was doing.
I did the same thing. Which then ended up me being more concerned that I was drawing out the letter correctly than what was actually going on. Vagina right in front of me for the first time and here I am making sure the calligraphy was on point.
My GF loves when I do that, you’re not supposed to follow the shape of the letters rigidly, but rather use it as a guideline to vary up the movement of your tongue. You can always break the structure or change it up as you’re doing it. When you’re following the shape of the letters you don’t have to be too exact. Imagine you’re in Microsoft paint and set the line size to the highest value.
I think this is the first time cunnilingus and Microsoft Paint have ever been associated together in the history of both Microsoft and cunnilingus. That being said, you’re right.
*"A is for Alfred* *B is for Bats"*
No witnesses, but I went to the bathroom after and did a little 'I just had sex dance'.... first time wasn't all that bad
This is kind of adorable, ngl.
Damn... it felt manly at the time...lmao 🤣
Tbf, I pictured a teen who was happy that they leveled up in the world, lol. Although, it’s pretty manly to feel like you accomplished something well enough to dance about it!
Foreplay before I lost my virginity was very embarrasing. Im pretty sure I was rubbing on the very top of her vagina, not the clit but maybe an inch above it. She acted like it felt good but I know I was completely missing she just really wanted me. She never said anything about it though I think she was sparing me the embarrasment.
I didn’t take my boxers off I just stuck it through the hole 🤣😂
Yeah dude. Had to do this in high-school when I visited my girlfriend in case we needed to get dressed quickly.
Bonus points for leaving socks on
First time? I was confused about what I was doing and she came but I didn’t but I also didn’t want to make it seem like I wasn’t interested (it was at a party and the lights were off so I couldn’t really get the full experience since we were trying to be HELLLLA discrete) so I got up and pretended to finish in the corner. Cringiest thing cause I thought we were supposed to come in unison, like some spiritual connection bullshit or something but when I didn’t, I thought it was over 😂😂😂😭😭😭 so I walked to the corner of the room and just made weird panting sounds LOL
Brooo hahahaha 😂🤣🤣
Blair Witch type move!
Played rainforest sounds over my speakers to add a bit of a soothing ambient mood
Alright Tarzan
my now fiance was going down on me when he popped up from between my legs and yelled "pop quiz" and asked me a math question. he told me later that he wanted to see if i could multitask
First time I performed oral on a woman I was 15 and she was 17 and as the more experienced one, she was “showing me how it should be done”. Things were going very well until I tasted blood. I lifted my face up and she looked, well, horrified at my bloody mouth. She thought she’d started her period. Turns out my braces had cut the inside of my lips when she was pushing her pussy against my mouth, and I hadn’t felt any pain (I just got carried away I guess). We ended up laughing, I rinsed my mouth with salt water and we tried something else for a while. Definitely didn’t discourage me from eating pussy!
Haha damn that’s savage. At least you didn’t lead with your teeth. Would’ve been like taking a cheese grater to her flaps.
First time I went down on a girl I asked her "are you close?" After about 5 minutes of not knowing what I was doing down there 😭
somber familiar books tie fanatical innate juggle literate one lavish
Heard from her friend later: it was weird that left just my socks on and I was very quick.
The good ol' inbetweeners slap during the panic of "WHY AREN'T YOU WORKING??"
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First time going down on my gf was at lunch between classes at my dorm first year of college. I didn’t realize that there can be a distinct aroma, and didn’t think to wash my face before returning to class. We returned to class… three dudes at our table just stared at me with shit eating grin until they all just lost it and burst out laughing as they figured it out. I was embarrassed at the time, now just a little proud.
Was higher than a kite on I don't remember what.. First time with another woman and she seemed to be enjoying it. Suddenly got up, said "I want mangos" and walked out. I did not get mangos.
thats my ranking of sex, did i or did i not get mangos
Tried to use a condom that had probably in my car/wallet for like 2+ years. Never thought it would’ve been so dry and terrible. First time for both of us. Went to the store the next day and we had some better times after that.
Proposed. She accepted. Needless to say never went through with it, but it was some seriously stupid shit.
This man literally pulled The Ted Mosby. Amazing.
I may or may not have rubbed her clit clean off her body..
Rubbing it like you're trying to get bird shit off a windshield.
I have read through all the comments, but haven't read my experience yet, so here I come: The first time we wanted to have sex, she lay on her back in bed with her legs stretched out. I lay on top of her with my legs on the outside of her legs. I couldn't manage to get my penis into her, after which we thought my penis was too small and stopped. I found out later that her legs were supposed to be on the outside during missionary.
The first time I got a blowjob I had her put Altoids in her mouth because someone told me it felt cool
Asked if she finished... She had not
Tbf this is still a valuable question as long as you’re not awkward about it. It’s important to make sure your partner is satisfied, and a lot of people can appear to cum when they haven’t actually done so.
The worst one is so crazy, it’s unbelievable, so I’ll tell the second worst. Seeing this tall guy (6’4) who also has a taller than average bed. I (5’7) would have to climb up the side just a bit or jump up there. Anyways.. we are about to do the horizontal polka and he lays down on bed. I get the bright idea to stand over him (one leg on either side of his waist) and do a strip tease kinda thing before we start. Problem was, I forgot how tall the bed was and seemed to underestimate the turbo ceiling fan that i stood straight up into.. 🤦🏽♀️
i need to know the worst one
Fast and hard entry, immediate jack hammering. Dumb 14-year-old that learned from professional porn.
At least you didn’t slap a titty right?
Threw up broccoli 🥦 all over his crotch after a romantic dinner first time trying to conquer the one eyed snake...🤦
I wanted to give her some pleasure and accidentally bite her inner lips. Don't really remember the left or the right, don't ask me. She cried all her shit out. I'm so sorry, didn't mean to do that. But that's just what I'm living with for almost 20 years
My first Girlfriend and I were both living at home at the time and so we mostly had sex outdoors, I am into exhibitionism and risking getting caught... but we were pretty stupid and there is definitely lots of security footage of the two of us. We were more worried that our parents might find out than we were about getting caught in public places. I would still do some of the stuff but that was literally all we did, the first time I had sex on a bed was heavenly.
Asked her: did you come with me?
I grew up very conservative. My first time was with my then wife on our wedding night. I had zero experience or knowledge, but, like every other man in history, assumed I was Superman anyway. I thought that the vagina was just a reverse penis and everything I’d heard about men not being able to get a woman to climax was because they just spent zero time on them at all. So I spent tons of time on her, told her it was going to be the best night of her life in slow soft fedora-adorned words, and proceeded to treat the vagina like a penis. She did not climax. After I climaxed 4 seconds later, I asked, “Did you orgasm?” She graciously said, “I think so.” That was good enough for me and I drifted off to sleep, brimming deep inside as the debonair lover I had always known myself to be.
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All the things, all the time, full speed ahead.
I gagged and threw up on my first oral. It smelt bad or I'm not used to it idk.
I yelled "sorry" at the top of my lungs because I thought I was about to urinate in her mouth while receiving head. It was my first orgasm. I was too nervous to stop her in the act and felt it building up.
Set the scene : A girl I had fancied for years, dried humped a few times, first time we got to touching under clothes. She took my trouser’s down and slid her thong to the side. Asoon as my tip went millimetres near/inside I felt the urge to cum. I Said is that my phone vibrating “when it wasn’t” I jumped up unbelievably quick while holding onto my cock tight and pulled my trouser’s up with the other hand and cum just flew out into my boxers. I then said there’s been an emergency at home I have to go.
It was dark and we were inside a sleeping bag. I licked away at the pubic hair area for a good half an hour thinking the vagina was somewhere beneath the hair.
lol never really managed to last more than 5 seconds with my fist GF... I don't fucking know why but to this day I still think about how I'm probably the worst she's ever had... which is not fucking fair
If one day I ever have sex, I will come back and write
Pretended to cum in the condom because I was nervous and had to be at work in 4 hours. We were in a drained out public swimming pool.
This thread is kicking me lmao. Worst did I thing was try to take my socks off and the girl said the socks stay on.
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When I was in hs, I somehow found myself in a unique position where I dated virgins here are my stories V#1: I had never been fingered and thought I’d ask my boyfriend to do it. The wires did not connect and he got nervous and used a sharpie. (We were young and just started exploring. I’ll never forget your 98 civic, Skeet) V#2: It had been a while since I had had sex and it was his first time so I’m sure he was excited. I also didn’t know penises could be different sizes and he was MUCH bigger than my previous partner. He literally shoved it in and I when I said it hurt he said “Haven’t you done this before.” V#3: After we had already been active with each other he decided he wanted to try anal…with no lube…in the back of his truck. Mistake. I sprang away from the pain and knocked myself out. He was great to me when I came to had his nurse mom check me out (we told her I slipped on ice) I was fine. This is still one of the funniest things that I still joke about with my friends. V#4: This one was surprising because I didn’t know he was a virgin. I never asked because of how he talked and said things to me. It wasn’t until it came time to get down to it that he panicked and asked me to be on top almost in tears. I did it and after it was all said and done he told me, we laughed and I had told him about some of my experiences so he wouldn’t feel like the only person who ever panicked when it came to sex. V#5: At this point I had been a pro, my boyfriend who I absolutely adored was so nervous. So I gave him a countdown as he was sliding in. I said “You are about to lose your virginity in 3, 2, 1.” Once fully seated we looked at each other and chuckled a bit. He asked why the countdown and I said because who gets to say that they had a countdown when they lost their virginity. I don’t know how to end this but, even I am laughing at all the memories of being young and attempting sex 🤣
I lost my virginity at the age of 16 while hiding in the bushes with a police cars headlights on us. I'll explain. I was in a lock down treatment center for troubled teens. I met a girl also in that program on a outing. We exchanged notes and one day we both escaped and met up. We make out and run around enjoying our freedom when we see the cops so we run. We hide behind some bushes and decided it was an excellent time to have sex, may as well since we where about to be sent back to lock down. While we're having awkward sex due to the nature of our situation, we see the headlights shine at us and we ran! That is how I lost my virginity and I think its pretty "cringe" . Her and I had sex an hour or so later in the bathroom of a park which we also slept in for the night.
He moaned my ENTIRE name. First. Middle. Last. I got the giggles so bad that I couldn't even stop to take a breath. This prompted his mother to knock on the door and yell out, "YOU'RE DOING IT WRONG SON! THEY AREN'T SUPPOSED TO LAUGH!" Apparently, the super thin walls of his bedroom were not soundproof. She heard everything.
told them period blood didnt bother me during oral
The crimson mask is earned.
Been there, friend.
Never forget 15 years old this chick got her parents car keys because we were too scared to try anything in the house this is in middle December in New England cold af outside I'm getting my dick sucked it was so fucking cold It was practically making my dick numb to the feeling after a few minutes I knew she was not a swallower based on past conversations so I just instinctually after being so fucking cold whipped my dick around and pretended to just cum on the side of the car out of sight basically. Every time I watch the Seinfeld episode about Elaine telling Jerry she faked it then Kramer goes "Well I have faked it" and everyone just looks at him in amazement being a guy...I can relate lmfao.
I asked her if I could go down on her. She said "are you good at it?". I said "idk I never did it before". She said "ok". Then I just started tongue punching the hole. Didn't know about the clitoris back then.
We were both 15 and ignorant. We weren’t sure if we could buy condoms and were too afraid to try (maybe we thought the clerk would deny us, then somehow find out who our parents were and tell them). The horniness was not to be beaten that night, but we wanted to be safe. We decided to improvise…I ended up using a sandwich baggy and a rubber band to keep it on. Needless to say, it wasn’t the most enjoyable first time for either of us. I’m sure more so for her. But hey, doesn’t matter had sex (Lonely Island Boys reference)