Author Topic: Awkward Sexual Experiences  (Read 464372 times)

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scorpion1001

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Re: Awkward Sexual Experiences
« Reply #1470 on: July 04, 2014, 05:15:36 PM »
i'd just use the condom at that point rather than deal with that stupidity

j....soy.....

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Re: Awkward Sexual Experiences
« Reply #1471 on: July 05, 2014, 07:22:12 AM »
Or have her finish you off manually with your dick outside a window,....

She may have accepted that..

ill_Murray

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Re: Awkward Sexual Experiences
« Reply #1472 on: July 09, 2014, 09:48:59 AM »
So let me set the scene for you guys.  It's a Saturday night, closing in on 1 am and here I am, sitting on the bed of a girl I had spent the last few hours chatting up.  As she does whatever pre-hookup ritual it is that girls do in the bathroom, I sit back in gleeful anticipation of the delightful sensations that I'm about to experience on and around my penis.  A few minutes go by, and she enters the room, a bit of a defected look on her face.  After a moment of silence, she informs she is just finishing her period, but had thought it would be over by now.  She then proceeds to do one of the most selfless things a human female can do when on her period and proceeded to go downtown.  2 minutes.  That's about how long the enjoyment of the fellatio lasted.  All of a sudden every good sensation turned to pain, I became extremely nauseous, vision fading...  I jolt up in the bed and quickly realize something has a hold of my balls.  I twist again and she releases them from her iron grip and sits back confused. 
"What the fuck was that?", I manage to whimper. 
"You didn't like it?", she replied confused. 
At this point I've now jumped rolled off the bed to collect my things. "No, why would any guy every like having his balls destroyed?"
She went on to explain how the only guy she had ever been with was really into some masochistic shit and she just assumed most guys were like that. 


This other time I fingered a girl at an Incubus concert and this incredibly convincing David Bowie look-a-like was creepily taking pictures of us hooking up. 
ill murray, can you remind me why you think im a kook

ttching!

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Re: Awkward Sexual Experiences
« Reply #1473 on: July 09, 2014, 10:06:37 AM »
This other time I fingered a girl at an Incubus concert and this incredibly convincing David Bowie look-a-like was creepily taking pictures of us hooking up.

Looks like he creepily posted them on the internet as well.

ill_Murray

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Re: Awkward Sexual Experiences
« Reply #1474 on: July 09, 2014, 10:44:06 AM »
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This other time I fingered a girl at an Incubus concert and this incredibly convincing David Bowie look-a-like was creepily taking pictures of us hooking up.
[close]

Looks like he creepily posted them on the internet as well.


Wow that kid actually looks like a really rapey version of me
ill murray, can you remind me why you think im a kook

SHAWN COMBOVER

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Re: Awkward Sexual Experiences
« Reply #1475 on: July 09, 2014, 01:50:24 PM »
put did you put her in a choke hold?
doublesteveburger: I'm gonna stick to being sad and skating with my poor friends.
busey: he's like an avenged sevenfold song come to life who wandered around living off energy drinks.

Jim and Dan

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Re: Awkward Sexual Experiences
« Reply #1476 on: July 09, 2014, 03:30:17 PM »
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This other time I fingered a girl at an Incubus concert and this incredibly convincing David Bowie look-a-like was creepily taking pictures of us hooking up.
[close]

Looks like he creepily posted them on the internet as well.

[close]

Wow that kid actually looks like a really rapey version of me

What in the godless fuck is going on here?

So much shit happening in this picture, it's literally an observational overload!

Is this what happens now in the "souper kewl EDM scene" or during like a David Guetta set?

What do you tell your friends? "Bro, I totes fingered this chick during the Kaskade set while peaking in the modified k-hole"...

That kid looks like a damn trailer park rapist, the chick looks like she might be part of "Generation Autism" & the kid on the right is totally looking at her vagina tan-line whilst enticing himself with a old-fashioned game of pocket pool...

EDM or whatever the fuck you want to label it as has to be one of the worst scenes out there.
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Re: Awkward Sexual Experiences
« Reply #1477 on: July 09, 2014, 03:36:58 PM »
She went on to explain how the only guy she had ever been with was really into some masochistic shit and she just assumed most guys were like that. 

the last thing you do with a girl like this is leave!!! she is obviously willing, but untrained. a dream girl if you ask me.

Jim and Dan

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Re: Awkward Sexual Experiences
« Reply #1478 on: July 09, 2014, 03:44:08 PM »
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She went on to explain how the only guy she had ever been with was really into some masochistic shit and she just assumed most guys were like that. 
[close]

the last thing you do with a girl like this is leave!!! she is obviously willing, but untrained. a dream girl if you ask me.

You don't feel an inherent guilt in manipulating a young woman to cater to your sexual desires?

I've had opportunities like that before & it always felt weird to me...

Roll for Rusty, Frip, Dapple and Tate



"My boiz better take my body, and boardslide me down the fucking bridge, in San Francisco"

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Re: Awkward Sexual Experiences
« Reply #1479 on: July 09, 2014, 03:55:55 PM »
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She went on to explain how the only guy she had ever been with was really into some masochistic shit and she just assumed most guys were like that. 
[close]

the last thing you do with a girl like this is leave!!! she is obviously willing, but untrained. a dream girl if you ask me.
[close]

You don't feel an inherent guilt in manipulating a young woman to cater to your sexual desires?

I've had opportunities like that before & it always felt weird to me...


Dear god no. If she's GGG, go with it. I suppose I'm down to reciprocate in all sorts of ways, but experimenting and trying new things is the best. You obviously don't want to do that with somebody who isn't into it, but if a girl is into it, why not?




you guys ever get the swallow and immediately brush her teeth girls? I've had that before. The girl would swallow, make sure I had melted into a pool of gooey happiness, and would excuse herself to the bathroom to brush her teeth then snuggle back in bed with me. At first I thought it strange, but that shit is nasty, and if that's what she needs to do to swallow, that's fine by me.
Are you a kook? If you would say this, the answer is “YES”
I quit skating for a time due to piling out

SHARPSHOOTER

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Re: Awkward Sexual Experiences
« Reply #1480 on: July 09, 2014, 04:02:30 PM »
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I think the rule with cumming in mouths during bj's is this:
If you don't warn her when you are going to cum at least the first time, you are a dick
If you warn her and she pulls away, she is a bitch.

One time a girl gave me a hand job, and told me to tell her when I was going to get off. I did, and she finished the hand job in her mouth. I wasn't complaining, but it was odd.
[close]

That's oddsome.
[close]
I've had that happen once, but I was 17 and the girl took it upon herself to hoover it down when I gave her the warning. I guess I didn't know that was even an option.

Most girls (in my experience) swallow. I've only had a handful of girls that I've ever been with that even hesitated at it, and only one of them flat-out refused, but for some reason she was fine with me cumming on her face...so...weird, but I'll take it.
[close]



I used to hook up with this girl, had sex a few times without a condom. Obviously she wouldn't let me finish inside her so I'd pull out but she wouldn't let me finish on her or anywhere close, had to like.. run to the bathroom or like blow it in the garbage can. I feel like that's fucked up idk she was Asian and really picky about everything
That's when you accidentally splooge in her face.

ill_Murray

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Re: Awkward Sexual Experiences
« Reply #1481 on: July 09, 2014, 06:19:27 PM »
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She went on to explain how the only guy she had ever been with was really into some masochistic shit and she just assumed most guys were like that. 
[close]

the last thing you do with a girl like this is leave!!! she is obviously willing, but untrained. a dream girl if you ask me.
[close]

You don't feel an inherent guilt in manipulating a young woman to cater to your sexual desires?

I've had opportunities like that before & it always felt weird to me...


[close]
Dear god no. If she's GGG, go with it. I suppose I'm down to reciprocate in all sorts of ways, but experimenting and trying new things is the best. You obviously don't want to do that with somebody who isn't into it, but if a girl is into it, why not?




you guys ever get the swallow and immediately brush her teeth girls? I've had that before. The girl would swallow, make sure I had melted into a pool of gooey happiness, and would excuse herself to the bathroom to brush her teeth then snuggle back in bed with me. At first I thought it strange, but that shit is nasty, and if that's what she needs to do to swallow, that's fine by me.


Sadly, not all the time.  I was hooking up with this one kinda freaky chick who enjoyed a little bit of pain.  Unfortunately, she felt I should see what it was like so one time as we're going at it she just winds up and full on, open palm slaps me across the face.  Turns out my previous assumptions regarding my feelings towards pain were pretty dead on. 


Also I've definitely had a few chicks who go immediately brush their teeth after swallowing but that was back when I was smoking cigarettes which I've read leaves splooge tasting even worse then I imagine it already does. 

Has anyone tried the Banana trick? You eat 1 or 2 bananas a couple hours before sex and the potassium lets you paint a fucking room.
ill murray, can you remind me why you think im a kook

Rumpleforeskin

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Re: Awkward Sexual Experiences
« Reply #1482 on: July 09, 2014, 07:59:55 PM »
I got called "daddy" for the first time, she was Asian too so I guess that makes it cooler.

ill_Murray

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Re: Awkward Sexual Experiences
« Reply #1483 on: July 09, 2014, 08:42:15 PM »
The first time a girl stuck her pinky in my butt... :o
ill murray, can you remind me why you think im a kook

Rumpleforeskin

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Re: Awkward Sexual Experiences
« Reply #1484 on: July 09, 2014, 10:38:21 PM »
Hell yeah, shit goes.

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Re: Awkward Sexual Experiences
« Reply #1485 on: July 09, 2014, 11:02:06 PM »
The first time a girl stuck her pinky in my butt... :o
MARRY HER
Are you a kook? If you would say this, the answer is “YES”
I quit skating for a time due to piling out

Matze

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Re: Awkward Sexual Experiences
« Reply #1486 on: July 10, 2014, 05:46:22 AM »
The first time a girl stuck her pinky in my butt... :o

MY SON!

ill_Murray

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Re: Awkward Sexual Experiences
« Reply #1487 on: July 10, 2014, 06:56:17 AM »
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The first time a girl stuck her pinky in my butt... :o
[close]
MARRY HER

I actually jokingly mentioned marrying her one time like "oh man that was so amazing, I could marry you," and she got way too stoked and started talking all this citizenship stuff. (she was from Russia) I guess they don't joke much in Russia because she did not find it the least bit funny.
« Last Edit: July 10, 2014, 08:57:44 AM by ill_Murray »
ill murray, can you remind me why you think im a kook

Rumpleforeskin

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Re: Awkward Sexual Experiences
« Reply #1488 on: July 10, 2014, 08:23:06 AM »
She's Russian too?  You're really out here doing things, my dude.

ill_Murray

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Re: Awkward Sexual Experiences
« Reply #1489 on: July 10, 2014, 09:02:18 AM »
She's Russian too?  You're really out here doing things, my dude.

I've been fortunate enough to do all my living in or right outside major cities. You never know who you'll meet.

And good for you on the Asian chick, they're definitely in my top 3 as well, especially trashier ones. 
« Last Edit: July 10, 2014, 09:08:05 AM by ill_Murray »
ill murray, can you remind me why you think im a kook

SodaJerk

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Re: Awkward Sexual Experiences
« Reply #1490 on: July 10, 2014, 09:34:20 AM »
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The first time a girl stuck her pinky in my butt... :o
[close]
MARRY HER
[close]

I actually jokingly mentioned marrying her one time like "oh man that was so amazing, I could marry you," and she got way too stoked and started talking all this citizenship stuff. (she was from Russia) I guess they don't joke much in Russia because she did not find it the least bit funny.
Well you did put a ring on her finger...

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Re: Awkward Sexual Experiences
« Reply #1491 on: July 10, 2014, 10:22:35 AM »
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The first time a girl stuck her pinky in my butt... :o
[close]
MARRY HER
[close]

I actually jokingly mentioned marrying her one time like "oh man that was so amazing, I could marry you," and she got way too stoked and started talking all this citizenship stuff. (she was from Russia) I guess they don't joke much in Russia because she did not find it the least bit funny.
[close]
Well you did put a ring on her finger...

+1

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Re: Awkward Sexual Experiences
« Reply #1492 on: July 10, 2014, 12:16:38 PM »
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The first time a girl stuck her pinky in my butt... :o
[close]
MARRY HER
[close]

I actually jokingly mentioned marrying her one time like "oh man that was so amazing, I could marry you," and she got way too stoked and started talking all this citizenship stuff. (she was from Russia) I guess they don't joke much in Russia because she did not find it the least bit funny.
[close]
Well you did put a ring on her finger...



wow amazing ^^^ *applause*

ill_Murray

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Re: Awkward Sexual Experiences
« Reply #1493 on: July 10, 2014, 04:36:51 PM »
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Expand Quote
The first time a girl stuck her pinky in my butt... :o
[close]
MARRY HER
[close]

I actually jokingly mentioned marrying her one time like "oh man that was so amazing, I could marry you," and she got way too stoked and started talking all this citizenship stuff. (she was from Russia) I guess they don't joke much in Russia because she did not find it the least bit funny.
[close]
Well you did put a ring on her finger...

She went for that stink ring fitting...behind my back.
 

ill murray, can you remind me why you think im a kook

Ronald Wilson Reagan

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Re: Awkward Sexual Experiences
« Reply #1494 on: July 13, 2014, 06:11:06 PM »
This is semi sexual at best, but last night was out with a girl at a bar, went out with her so I could have a smoke, she asks for one. I go into my pocket and pull out a box I feel in there. I pull it out and try to smoothly offer it to her, once it was too late, as I was trying to open the top flap, I realize its the box of condoms I bought for later that night. We hadn't actually fucked yet either...
She was cool about it though and made a joke "That's not the kind of smoking I came outside to do right now."
Are you a kook? If you would say this, the answer is “YES”
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ill_Murray

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Re: Awkward Sexual Experiences
« Reply #1495 on: July 13, 2014, 06:26:37 PM »
This is semi sexual at best, but last night was out with a girl at a bar, went out with her so I could have a smoke, she asks for one. I go into my pocket and pull out a box I feel in there. I pull it out and try to smoothly offer it to her, once it was too late, as I was trying to open the top flap, I realize its the box of condoms I bought for later that night. We hadn't actually fucked yet either...
She was cool about it though and made a joke "That's not the kind of smoking I came outside to do right now."


Did you still sex?
ill murray, can you remind me why you think im a kook

Ronald Wilson Reagan

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Re: Awkward Sexual Experiences
« Reply #1496 on: July 13, 2014, 06:53:46 PM »
Expand Quote
This is semi sexual at best, but last night was out with a girl at a bar, went out with her so I could have a smoke, she asks for one. I go into my pocket and pull out a box I feel in there. I pull it out and try to smoothly offer it to her, once it was too late, as I was trying to open the top flap, I realize its the box of condoms I bought for later that night. We hadn't actually fucked yet either...
She was cool about it though and made a joke "That's not the kind of smoking I came outside to do right now."
[close]


Did you still sex?
not last night. We went a little to hard on the booze and she passed out on the ride home. I think things are looking well though, she apologized a bunch of times about how she wanted me to come in, but was totally useless right now. We'll hang out again, I'm not worried. Worst comes to worst pukahontas is still around on that casual level...
Are you a kook? If you would say this, the answer is “YES”
I quit skating for a time due to piling out

yapple dapple

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Re: Awkward Sexual Experiences
« Reply #1497 on: July 13, 2014, 06:54:28 PM »
Not awkward to me, but maybe to you.
My type.


No lie.

sexualhelon

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Re: Awkward Sexual Experiences
« Reply #1498 on: August 11, 2014, 08:59:22 AM »
Long story short: Once I was hooking up with this girl and we were at that point where pants were off and foreplay was going down. She was on top, clothes were off, and my dick was between her butt cheeks. No condom was on yet or anything and out of nowhere she just goes for it - puts my dick in her butt. It was weird because she'd apparently gone into the bathroom to lube her butthole right before all of this.

get gnarly

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Re: Awkward Sexual Experiences
« Reply #1499 on: August 11, 2014, 10:15:08 AM »
My good male friend and I have a habit of having threesomes with girls we're fucking. Actually so far it's been girls I was fucking but its fine by me. There's a special atmosphere that takes place during a threesome, when everyone is on the same page and everything is in sync. This feeling of being in the moment is why we do these acts (also to bust a nut), but its usually really awesome. The last threesome we had didn't have any of these type of feelings involved, it just felt completely raunchy like we were filming a porno although that aspect wasn't all bad.

This chick is a 34 year old redhead with a nice body and a bob style haircut. Nipple rings, clit ring, I had fucked her before the threesome and knew she was a freak. My homie and I are both 22 so this was kinda a funny one from the get-go. After suggesting the idea of inviting my friend to join us after we had fucked a few times, I eventually received a picture message from her of the Eiffel Tower. I knew at that point she down and she proceeded to rent a hotel room. I showed up before my friend so I asked her a little about logistics. The most important question I had was does she like things in her butt, because my friend and I had done sort've "vanilla"y threesome stuff before but we wanted to get double penetration going. She says she loves things in her ass, so I text my friend saying dp is cool.

My friend shows up and we shoot the shit for about half an hour before we start hooking up. We all get naked, we all are getting into it. She starts sucking my homies dick while I fuck her, then we switch and my homie starts fucking her and I proceed to choke her out forcefully with my dick. That was a little awkward but not bad. Then I decide its time to get this double penetration going to I lay down and have her fuck me. My friend grabs the lube and lubes her asshole. The thing with double penetration that is the most difficult is the amount of legs involved. Her on top of me leaves almost no room for my friend to fuck her doggy style in the ass. ALMOST no room, and he proceed to fuck her in the ass. So we have both our dicks inside this chick and I experience another awkward moment when I can feel him in her asshole while inside her vagina. We had never touched eachothers' dicks, assholes, or bodies whatsoever before besides whats necessary to make things happen. I got over this anxiety quickly and we fucking tore her up in the dp position for a while. We all have an orgasm and it  was pretty great.

After chilling for an hour and watching tv, I go to the bathroom and come back to them hooking up. I'm hyped because I've never fucked a girl in the ass and figured doing it with my friend in a chick's pussy is a great time to start. Things get going, etc, and I'm behind her with him inside her. I go for it and my dick slips in there pretty easily due to the half bottle of lube I used. It felt alright but sort've felt like I was jerking off with two fingers. And a few time, my dick would just shoot right out of her asshole like sheshitted it out which was funny. Like an all in or all out scenario.

I didn't enjoy fucking her in the ass so much so I stopped and laid down while she sucked my dick. My friend starts fucking her in the ass HARD, really fucking hard, and she's struggling not to moan in order to suck my dick. This is where it got the most awkward of the night. Looking up at my friends face while he's hurting this girls asshole with his dick, and seeing this 30 something year old redhead suck my dick, on top of what had already gone down that night, I LOST it. I started laughing harder than I've ever laughed, like Tim and Eric were right there narrating what was going on. I just couldn't stop, and the fact I knew this is one of the worst times ever to be laughing made it even harder. I think in acting they call this corpsing, but anyways it lead my friend friend laughing a little bit too and the chick giving me a dirty look as she sucked my dick. I grabbed a pillow and basically had to choke myself out in order to stop laughing. After a little while, my friend was over it and so was I and we all stopped. The moments after we stopped were also very awkward. What do you say to someone who you just caused so much pain and embarrassment? This wasn't my ideal threesome but I am glad I had that experience of it being like a porno.

TL;DR I laughed very hard during a funny threesome. Sorry this was very long and not super awkward, but it was a very abnormal and awkward experience overall for me.