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Awkward 1st times

Tell your awkard 1st times FJ

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Submitted: 04/10/2014
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User avatar #2 - charagrin ONLINE (04/10/2014) [+] (18 replies)
>be 16
>be at slutty girls house
>be about to lose virginity to slutty girl
>Slutty girl suggest doggystyle for first time and bends over
>ram dick in hard
>wrong hole
>6 inches deep
>slutty girl screams
>Slutty girl's older jock brother runs in
>leave slutty girls house with black eye and virginity intact
#3 to #2 - dildodude (04/10/2014) [-]
I think that counts
User avatar #44 - midgettitwank (04/10/2014) [+] (26 replies)
>Be 15
>With this girl for a couple months
>BIt of a slut, but had ******* issues, was touched by her mums bf etc
>I had taken care of her and **** , her other boyfriends had hated her apparently
>She had some black gang members as ex boyfriends
>black
>I was expecting her to feel nothing
>The time came to dance the dance
>She put the condom on for me because i saw that **** in the inbetweeners and it was cash
>We try missionary on her tiny bed
>It was **** , i probs wasnt doing it right
>20 minutes and meh
>She opens a karma sutra book thing and picks a random page
>We end up ploughing in her daddy's bathroom, on the counter. The "counter tap"
>This was alright actually
>Going for about 20 minutes, absolutely exhausted
>Sweating like a malaysian in an airport
>Not climaxing, she claims she had already had a few orgasms
>Change position to the cowgirl on her bedroom floor
>This is more like it
>10 minutes in we're going quickly
>about to cum
>Her kitten jumps and sits on my face just as I ejaculate
>I came looking at a kitten's penis
To this day I wonder if I am a gay furry
User avatar #15 - sexyhimself (04/10/2014) [+] (4 replies)
>
>
>
>

and that's my first time story
#34 - graknab (04/10/2014) [+] (14 replies)
Move over everyone, best story coming through;
>last summer
>mutual friend tells me the schools valedictorian is into me
>never been within 20 feet of her, she looks like a solid 6
>agree to a date, we go on a hike
>up closer shes more like a 3
>whatever, I already came this far
>walking down the trail, shes not laughing at any of my jokes and barely responds to my questions
>about to give up when she jumps on me and starts making out
>first kiss, but even I know that its bad
>like a cow with rigor mortis
>tell her we should move off the trail
>we go a ways into the woods and find branches laid against a tree, prolly some kids play area
>go inside, she starts sucking my dick
>drags her teeth along the shaft
>suggest we have sex
>"okay but I'm on my period"
> **** it, its already up
>takes off panties
>vag looks like osama bin laden, after he was shot
>put it in, **** for like 40 minutes, neither of us come (her because I suck, me for obvious reasons)
>get bored, she offers to give me a hand job
>not very good, I try to finish myself off but shes staring at me, so I don;t
>leave bloody condom in children's play area,walk back in basically silence
>she drives me to my car, kiss her goodbye, never talk to her again
User avatar #27 - connorjay (04/10/2014) [+] (4 replies)
Seeing as everyone is doing it:

>be 14
>be at gf's house
>she suggests sex
>both virgins
>I put condom on easily (because I practiced so I didn't look like a ******* idiot)
>Put dick in
>thrust for a couple of minutes
>she says it hurt her too much and to stop
>she finishes me with her mouth

We tried again a couple days later. Her friend told her to "grin through the pain of your first time". Probably lasted a minute. If that.
User avatar #28 to #27 - connorjay (04/10/2014) [-]
To this day my friends still joke about "using her tears as lube"
User avatar #33 - assassindash (04/10/2014) [+] (8 replies)
>Be 15
>Be at home with lesbian cousin's best friend's little sister.
>Shes 17
>Go to sleep
>Wake up with her on top of me
>Already penetrated
>Too tired to give a ****
>Gives ****
>came outside
>Made sacrifice to glorious leader the next day. Again.
User avatar #59 to #33 - shinigamizak (04/10/2014) [-]
sounds like you were raped bro, sorry
#38 - Ulric (04/10/2014) [+] (10 replies)
>be me
>be 15
>at gf house
>parents at some ****** antiques fair
>go go sexy time
>condom on, dick in
>last a decent time
> ******** .jpg
>pull out, condom broke
> ****** .jpg
>gf loses her ****
>super religious parents, would flay me if they knew
>all her tears and what-ifs
>desperately try to calm her (and myself)
>30 mins later gets her period

MFW all clear
#112 - manirock ONLINE (04/10/2014) [+] (8 replies)
>Be me, senior year at a tiny Christian high school
>Like 15 girls in my class
>Known them for at least 6 years
>All of them annoy the **** out of me
>Prom rolls around
>Don't ask anyone to go with me
>Decide to go anyways because I want to win prizes at the after prom
>During dance someone asks the DJ to play "smooth criminal"
>One of my favs, so I go out to the floor and breakdance
>I'm not anything special at it, but I have a few cool moves memorized
>Do them and then walk back to my table cool as a cucumber
>Fast forward to end of the after prom
>Friend, his date, and me decide to go back to my place to spend the night
>Friend's date is a sophomore
>They were just friends and not in a relationship
>We are all chilling in my living room watching South Park on DVD
>Friend runs out of cigarettes and goes out to buy more
>32% sure that friend's date had a crush on me
>Blurt out "Wanna get it on"
>Smooth Dylan, smooth, you nailed it
>She replies in a hushed tone "yeah"
>Super excited, freak out internally, mind racing, intensely confused
>Say "just kidding"
>No no no no what have I done?!?
>Fast forward five years, still virgin, living a life of regret
User avatar #32 - sinonyx (04/10/2014) [+] (5 replies)
23
virgin
don't give a ****
#49 - gux ONLINE (04/10/2014) [+] (7 replies)
Story time bitches.
>Be 14
> Friend says a girl in his class likes me (we were in paralell classes)
> Introduce me to her
> atleast a 7.5
> Being a beta fag at that point i didn't talk much to her
> She mistakes my faggotry for being shy
> A couple of weeks go by start talking to her a bit more
> Time for the school prom (it works diffrently here)
> Had a bottle of vodka hidden outside in the school yard (Most people hid their alcohol there)
> The night passes and after drinking most of the vodka i felt confident enough to talk to her
> Alphamodeengaged.jpg
> "It's hot in here want to take a walk with me?"
> She says yes
> after going out a bit on the schoolyard things are getting pretty heavy
> Were glued together like your asscheeks after a couple of hours down in the gym.
> Expanddong.exe
> About to have sex, **** yeah.png
> we decide to **** against a wall
> After about 10 minutes a teacher comes out (They were looking for people who snuck out drinking)
> Shines his flashlight at us
> I don't know what to do she just pulls up her pants and starts legging it
> Get caught with my pants down against a wall with a raging boner
> They call my über-christian parents
MFW i had to walk to the teacher lounge with a trouser tent and getting grounded by my parents
#26 - whycantiusecaps (04/10/2014) [+] (5 replies)
> Be 17
> Been in friend zone with girl for two years
> Best Friend
> Decided to give it a go (Thanks 50 shades)
> Never put condom on before
> Spend too much time dicking about
> Inside out and everything
> Mood goes

> Week later
> Try again
> All's going well
> Lay on top of her
> Try and get it in
> Try and get it in
> Try and get it in
> Give up, eat her out, go to bed

> Months of me giving her oral
> More months later
> Friends Birthday
> Hotel by the sea
> Get drunk
> Find hole
> Came in 30 seconds
User avatar #16 - crazycommando (04/10/2014) [+] (6 replies)
-be 19
-hanging out in marseille
-decide to chat up some school hottie i knew back in the day
-decide t chill for a bit
-alcohol n' ****
-get tipsy
- go back to her place
- **** for 4 hours straight
-couldn't bust a nut
-gave her an orgasm
-see opportunity, pretend to cum
-roll of her sleep because exhausted
wake up next morning trying to play it cool, while she thinks im really good at sex and i couldn't even cum to save my life....
#134 - Deavas (04/10/2014) [+] (1 reply)
This image has expired
>be me
>be 19
>have sex for the first time
>im 18 now

this story changes numbers every year
#261 - bloorajah (04/10/2014) [+] (2 replies)
>gf wants sexytime
>head over to her house
>shes having a party with a few of her friends
>we get drunk as all holy hell
>i mean really drunk, " im going to die in my sleep" drunk
>start talking in my native german
>so drunk i become a nazi
>gf takes me to her room
(what follows is my exact memory of my first time)
>gf takes me to her room
>too drunk to know what happening
>think about hitler
>wonder why hitler decided to kill jews
>go on crazy wikipedia click spree in my brain
>keep thinking of hitler
>hear gf say "that was great, *yawn*
>probably fall asleep
>wake up next to gf
>"ich heiße Hilter" written across my chest in permanent marker

pic related. mfw i lost my virginity thinking of hitler
User avatar #14 - banteringcat (04/10/2014) [+] (1 reply)
Went outdoors to ****
Find rock that will do
Her on bottom get ready legs spread
Can't find the ******* hole
Ended up ******* a rock for 2-3 minutes before she guides me in.

Seriously. WTF was wrong with me.
#80 - spokengro (04/10/2014) [+] (1 reply)
Well here goes nothing..
>Be 16
>Started dating this girl who I thought had friendzoned me
> *******
>Date for a few months, all good
>Then the day came..The Gods had blessed me and I began my ascendance into manhood.
>Go to bedroom, things start getting hot
>time to get randy.
>Start off missionary, pretty decent. Continue like this for a good 10 minutes
>She suggests we do doggie.
>Odin's beard.. this is pretty damn good... until..
> I slide out by accident and as i thrust forward my dick hits something (a bone or something but definitely not the vagina)
>Honestly felt like my penis had snapped
Good times
User avatar #4 - dabronydude (04/10/2014) [+] (17 replies)
this is a thing you know,
people who masterbated so much to the point they find sex less pleasing then rubbing
one out.
#13 - fuzzyjred (04/10/2014) [+] (3 replies)
>Be 17
>Get absolutely smashed with my girlfriend of one month
>Drinking all night, later on we make it to my bedroom.
>Lights are out
>Last thing I remember "Are you ready?"
>Wake up next morning on my floor with no pants on girlfriend is no where to be seen
User avatar #39 - vonspyder ONLINE (04/10/2014) [+] (20 replies)
Well if were all doing it...

>Be 17, Senior year of HS
>Meet 7/10 girl in public safety class (Im also a 7/10). We hit things off well
>Start to date for a few weeks but then She dumps me out of nowhere
>Tell her I wont mind as long as she has an understandable reason
>She doesn't tell me so I insist
>She informs me she has left me for a 24 year old. i try not to puke
>Lie to her and tell her im not mad (Wheels in head already plotting revenge)
>Tell her cruel truth: If he is 24 then chances are he is already seeing someone and is cheating on them with her (I know how guys think since I are one)
>Leave it at that and go join the army once I graduate
>Come back from basic and AIT buff as **** (Now am 9/10). Drive to her place unannounced
>Shes home and sees that I even lift. she starts crying
> says I was right and he was actually married with kids and was cheating on wife with her.I Ask if she wants to get lunch.
>Go to lunch at fancy ass place with cloth napkins and **** . make her pay for it.
>Ask if she wants the d (Of course she does, Im buff now and shes vulnerable)
> now for this to work Ive got to give just about the best sex a woman has ever had.
>Might be a challenge since ive never done this before, but ive seen enough porn.
>Get a room with great hourly rates and give her the Vampire Hunter D.
>Goes on for an hour. finally finish. Bitch is twitching and smiling uncontrollably afterwards
>Take her home, drop her off, leave,Wait about an hour
>Suddenly the disposable prepaid cell phone I got (for this wonderful act of revenge) starts ringing. Never answer. Throw phone away.
>Heard from her friend she couldn't stop crying and thinks she did something wrong.
>Fak u bitch you never get this D ever again. Had massive amounts of sex after that with all of her friends.
.
User avatar #36 - vondraco (04/10/2014) [+] (6 replies)
Am I the only one with a relatively normal story?..
I'm still with the girl I lost my virginity to, and that was over two years ago.
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