Awkward Sexual Experiences

[buttpirate]

so me and this girl have been pretty tight for like two years now, one of those situations where dude is madly in love with the girl but ol girl is not really havin it like that. so over the summer we're kickin it alot because we both stayed on campus and shit, i drunkenly profess my love on several occations and subtly put in some friendzone elimination work.

so Das racist comes in to town and hes got this rapper from Houston, Fat Tony with him, I know some peeps who are cool with the dude from high school and me and girl end up smokin and drinkin wit Heems and fat tony. by now shes drunk as shit and super impressed by my ostensible connections. for a moment I was that Nigga.

so we're chillin at her crib and its like 4am. we in the same bed and shit and we get on some cuddle game, i should note that up to this point i was on the bitch route as a cuddle buddy for some time. but all of a sudden jesus comes down and gives me an in. she takes my hand and puts it over her left tit. oh glorius left tit that had been the forbidden kingdom for so long...at this point im activated all systems are go and ima get whats mine. I proceed to go from neck down to navel and make the most crucial error any man has made in history. i go from naval up to lips (i often do this to build anticipation in the girl) but this time it was a fatal error. full boner and all i hear the most crushing words a man could hear
"I cant kiss you,ahh this is too weird now"
i blew it. and then returned to cuddling like a bitch fully erect penis and all. I dont talk to this girl much anymore...

"cuddle buddy"?  you have zero chance of having sex with this girl, no not never

[BARACKOBAMA]

barack, in about 10 years I want to do your daughter. she's hot

permission granted, as long as you're American

[HairyCunt]

barack, in about 10 years I want to do your daughter. she's hot

You must be sad that they took the bestiality section off of motherless.com.

[jimi420]

A couple days ago my girlfriend and I were just watching Harry Potter and the Deathly Hallows pt 1 and out of nowhere she says "I want to sit on your face". I decline because I was really into the movie to which she just takes her pants off and plants her ass on my face. I start going at it because there's no way I can see the movie with her asshole blocking my eyes. Not 5 minutes into it and my dad walks into the room. She freezes up and just continues to sit there. I shove her bodily off my face onto the floor. I look at my dad and say "So... what's for dinner?" eh.

[oyolar]

Hahaha. Classic jimi.

[malibu hamish]

im not going to be able to top that one jimi but heres my story.

I was at this party and my friends girlfriend comes up to me and starts telling me how sheher friend wants to get down so i proceed to go talk to her. ONe thing leads to another and we go out to her car. While im fucking her i happen to look out the window and see some dude sitting with his front door open staring right at me. I have this petrified look on my face and the girl asks "whats wrong?" to which i reply some creepy fucker is watching she looks over and didnt seem to care one bit. Busted all over her car, went back to the party and continued drinking without her.


The dude was lurking really hard in his doorway.

[cancelled]

my friends girlfriend

damn, your a fucking tool

[jimi420]

Expand Quote

my friends girlfriend

[close]

damn, your a fucking tool

do you mean a real friend or just a dude  you've known and have kicked it with a couple times?

[weedpop]

I thought the awkward part of the story would be trying to decide whether or not to fuck your friend's slutty girlfriend. I guess "the Illusion" has no qualms about such things.

[malibu hamish]

I thought the awkward part of the story would be trying to decide whether or not to fuck your friend's slutty girlfriend. I guess "the Illusion" has no qualms about such things.

I must have miss typed. it was my friends girlfriends freind

[A.J.K.]

Expand Quote

I thought the awkward part of the story would be trying to decide whether or not to fuck your friend's slutty girlfriend. I guess "the Illusion" has no qualms about such things.

[close]

I must have miss typed. it was my friends girlfriends freind

[jgonzalez]

Expand Quote

so me and this girl have been pretty tight for like two years now, one of those situations where dude is madly in love with the girl but ol girl is not really havin it like that. so over the summer we're kickin it alot because we both stayed on campus and shit, i drunkenly profess my love on several occations and subtly put in some friendzone elimination work.

so Das racist comes in to town and hes got this rapper from Houston, Fat Tony with him, I know some peeps who are cool with the dude from high school and me and girl end up smokin and drinkin wit Heems and fat tony. by now shes drunk as shit and super impressed by my ostensible connections. for a moment I was that Nigga.

so we're chillin at her crib and its like 4am. we in the same bed and shit and we get on some cuddle game, i should note that up to this point i was on the bitch route as a cuddle buddy for some time. but all of a sudden jesus comes down and gives me an in. she takes my hand and puts it over her left tit. oh glorius left tit that had been the forbidden kingdom for so long...at this point im activated all systems are go and ima get whats mine. I proceed to go from neck down to navel and make the most crucial error any man has made in history. i go from naval up to lips (i often do this to build anticipation in the girl) but this time it was a fatal error. full boner and all i hear the most crushing words a man could hear
"I cant kiss you,ahh this is too weird now"
i blew it. and then returned to cuddling like a bitch fully erect penis and all. I dont talk to this girl much anymore...

[close]

"cuddle buddy"?  you have zero chance of having sex with this girl, no not never

At least he's touching an actual girl, Right? That's still kind of a win.

[malibu hamish]

Expand Quote

Expand Quote

so me and this girl have been pretty tight for like two years now, one of those situations where dude is madly in love with the girl but ol girl is not really havin it like that. so over the summer we're kickin it alot because we both stayed on campus and shit, i drunkenly profess my love on several occations and subtly put in some friendzone elimination work.

so Das racist comes in to town and hes got this rapper from Houston, Fat Tony with him, I know some peeps who are cool with the dude from high school and me and girl end up smokin and drinkin wit Heems and fat tony. by now shes drunk as shit and super impressed by my ostensible connections. for a moment I was that Nigga.

so we're chillin at her crib and its like 4am. we in the same bed and shit and we get on some cuddle game, i should note that up to this point i was on the bitch route as a cuddle buddy for some time. but all of a sudden jesus comes down and gives me an in. she takes my hand and puts it over her left tit. oh glorius left tit that had been the forbidden kingdom for so long...at this point im activated all systems are go and ima get whats mine. I proceed to go from neck down to navel and make the most crucial error any man has made in history. i go from naval up to lips (i often do this to build anticipation in the girl) but this time it was a fatal error. full boner and all i hear the most crushing words a man could hear
"I cant kiss you,ahh this is too weird now"
i blew it. and then returned to cuddling like a bitch fully erect penis and all. I dont talk to this girl much anymore...

[close]

"cuddle buddy"?  you have zero chance of having sex with this girl, no not never

[close]

At least he's touching an actual girl, Right? That's still kind of a win.

has there been stories of those weird mannequin people?

[nice weather]

yea the vitamin c should get the job done, not to worry

[The Human Condom]

Did you ever get tested solo?  Do you have a venereal?

[crackrazor]

yea the vitamin c should get the job done, not to worry

[Goblinshark]

Did you ever get tested solo?  Do you have a venereal?

I know this guy, he fucks with high school girls

[Chris Hansen is back]

What the fuck, man. I'm right here.

[Jackie Joyner Kersee]

What the fuck, man. I'm right here.

[solo]

Expand Quote

Did you ever get tested solo?  Do you have a venereal?

[close]

I know this guy, he fucks with high school girls

human condom..

i have yet to get tested.


factoring in some the math of there being 3 girls that i've definitely gone in uncondomed with...... and adding the possibility of what girl could have what based on how freely people fornicate these days leads me to....... not want to think about it any more... i think i'm good though. it's been a while and everything's normal lol.


and goblinbabydicks


the girl from the story was 22

and the other girl i dated for a while with the car was 20

oh, and the first girl i heemed was some bakery prodigy 19 year old


you make it seem so bad eric -_-
for the record, the girl who i brought over to the house the day i was painting has been out of high school for a while..

[Alan]

lol.

Oh yeah, lols for days.

[saucy ragu]

oh, and the first girl i heemed was some bakery prodigy 19 year old

I want to hear about this. And is there a video of her baking?

[solo]

Expand Quote

oh, and the first girl i heemed was some bakery prodigy 19 year old

[close]

I want to hear about this. And is there a video of her baking?

yeah i setup a hidden camera and filmed her fisheye when we'd have crazy sessions in the bakery. we'd make a real mess of the place after hours.

cake batter and genital juices everywhere.

[ice nine]

U also did a hit and run u piece of shit

[solo]

U also did a hit and run u piece of shit

fuck, hit and run is a dick move....

there was so much going on that i sort of blocked that part out .....

hope it's all good by now ...

[dkn]

i was about to lose my virginity

too nervous to buy condoms over the counter

so i went to a bathroom vending machine

things get heated and she opens up my purchase

...it turned out to be lube >_<

[dkn]

and once i dated a girl for two years

for valentines day she cooked me dinner

i chopped the habaneros cause i love spicy food

after i clean up the table i'm greeted by lingerie and candles

i start fingering her and she starts crying...

had i washed my hands maybe we would still be together

[jimi420]

and once i dated a girl for two years

for valentines day she cooked me dinner

i chopped the habaneros cause i love spicy food

after i clean up the table i'm greeted by lingerie and candles

i start fingering her and she starts crying...

had i washed my hands maybe we would still be together

my god dude. That's harsh.

[Hercules Rockefeller]

new post in awkward sexual experiences. okay.

its jimi. oh god oh god oh god i am excited.

he just responds to something.

disappointment, thy name be jimi.

[jimi420]

new post in awkward sexual experiences. okay.

its jimi. oh god oh god oh god i am excited.

he just responds to something.

disappointment, thy name be jimi.

Sorry to disappoint. I've had a dry spell as of late. Here's an oldie

When I was 17 I was dating this girl I'd had a thing for for a few years. She came over early one morning to pick me up for school. I sleep naked so she came in my room and there I was in all my black glory. She shimmies into the bed and we start making out and shit. That's when I take off her clothes and I lose my virginity. I've watched an absurd amount of porn so I wanted to try everything. I flipped her over and started going doggy on her and I look out my window and across the street at a home for mentally challenged people I see 4 of them just watching. I don't think she noticed but I did. I finished up and we left and as I walked out the door of my house they all just stared at me. I lost my virginity in front of mentally challenged people.