pathetic & failed attempts @ sexual relations

[nice weather]

How long into the evening until this thread popped up in your head?

[H8R part 4]

What did he say about it afterwards?

nothing really.  when we got outside i was like WTF!  i asked him why he/she didn't do or say anything and how i really didn't want to part of their love triangle or whatever the fuck.  if he wants to cheat on his wife, thats fine but i was like, why you trying to drag me into it?     
anyway, he didn't have much of a response so we were both kept it moving toward the subway.  i'm sure we'll discuss it further when i see him again.   

How long into the evening until this thread popped up in your head?

this and the awkward experiences thread instantly came to mind as soon as he mentioned 3 way. 
if it worked out i was going to post in the awkward experiences thread, if it failed i knew i'd be posting in this one. 
i wish i was posting in the other one, lol! 

 

[Donkey Lips]

Damn faster you seem to get invited to a lot of pig roasts man.

[H8R part 4]

i don't know where it comes from or what kind of vibe i'm giving off but i've asked a lot time, or at least what i consider a lot.     

the 1st time when i lost my virginity at the age of 13.  it was with 2 girls that were both 2 years younger than me.  they asked me to play truth or dare, which turned into just dare, which then turned into, you do this with her, then you do it with me.  i didn't know what i was doing at the time but i was pretty hyped on doing it!

next time it happened i was 17.  2 girls that were friends with each other both liked me and i met them at the same time.  i started seeing them both but they eventually tried to make me choose, i couldn't so they shared me for 2 months or so.  i thought i was the motherfucking man but it was only a matter of time before one of them got jealous and ruined it. 

next time was my next door neighbors.  they knocked on my fire escape window and asked me to watch them have sex and if i wanted to, i could join in.  i thought hard about it but opted out.  the dudes wife was hot but i had no desire to see her husband naked.  not to mentioned that i'd have to constantly see them since they lived right next door to me.  i can't tell a lie though, i peeped a couple times when i heard them getting busy...peep, peep, peeping tom over here!     
       
another time was this lesbian chick i was friends with and her GF.  they used to come by my store all the time and one night i hooked up with the lesbian chick.  she was 22, never been with a dude before, felt comfortable around me so i let her experiment.  she literally did everything you could imagine.   it was kind of awesome but then she invited her GF over the next night and it got really fucking awesome!     

then theres the vodka porn chick that went nowhere.
 
after that, my bartender and his GF asked me to join them but i had to decline.  his GF was super hot and we got along the second we met but it would've been really awkward.  i went to that bar 7 days a week so it wouldn't have been a good look, not to mention my bartender swung both ways, the dude straight up said, "i want to suck your cock".  it was a little weird after that.         

at that same bar these 2 girls took me to their place and had their way with me.  i knew this one girl for a while, i ran into her all the time at the bar, on the train, and random places downtown.  anyway, shes chillin at the bar with her roommate and we get to drinking and shit, next thing i know they're following me out the bar.  i asked them whats up but they didn't say shit, they just grabbed me by my hands and took me to their apartment.  i was naked, they was naked, we was naked!         
         
another time this girl i know and her gay friend wanted to hook.  its safe to say i passed.  i'm down to tag team a girl but i only swing one way.

then this last time with my homey and his wifes friend which failed. 

[saucy ragu]

Have you gotten laid more often by two women/three people involved more than one-on-one?

then theres the vodka porn chick that went nowhere.

Strangely, same. She works as a promoter for an alcohol distributer and used to do porn. We went to some shitty local pub in a snowed in, dead town. No vibes were happening but we were getting along well. Before we even left I settled on just being friends, I had been on a few dates recently that amounted to nothing so I could read the signs. Also, if she worked in porn and was into me, I'd like to think it would be apparent. I paid and drove her home, had a small conversation in her driveway, hugged, and I zipped home because I hadn't slept since I got back from SF that day. Possible "FFFFUUUUUUUU" moment though, I think she was going in for a kiss when we hugged goodbye. She tilted her head ever-so-slightly as I aimed my chin straight for the shoulder, and grazed my cheek with a kiss that felt slighted--as though it wasn't intended for my cheek but elsewhere. I thought about it as I drove home but resigned myself to my tired mind.

We've hung out a few times since; treated her to a flick, I crashed in her guest room for a snow storm & went hiking the next day then fishbowled an igloo, taught her to play Take Two/Bananagrams. She's supposed to be taking me to my first strip club but that might be a while if it happens at all, she's going to Costa Rica for a month. So yeah, I've put in a bit of work that's amounted to no action. It's whatever though because I'm at least having a good time, and not turning in at the end of the night pissed about it.

[Bobbito]

Have you gotten laid more often by two women/three people involved more than one-on-one?

Expand Quote

then theres the vodka porn chick that went nowhere.

[close]

Strangely, same. She works as a promoter for an alcohol distributer and used to do porn. We went to some shitty local pub in a snowed in, dead town. No vibes were happening but we were getting along well. Before we even left I settled on just being friends, I had been on a few dates recently that amounted to nothing so I could read the signs. Also, if she worked in porn and was into me, I'd like to think it would be apparent. I paid and drove her home, had a small conversation in her driveway, hugged, and I zipped home because I hadn't slept since I got back from SF that day. Possible "FFFFUUUUUUUU" moment though, I think she was going in for a kiss when we hugged goodbye. She tilted her head ever-so-slightly as I aimed my chin straight for the shoulder, and grazed my cheek with a kiss that felt slighted--as though it wasn't intended for my cheek but elsewhere. I thought about it as I drove home but resigned myself to my tired mind.

We've hung out a few times since; treated her to a flick, I crashed in her guest room for a snow storm & went hiking the next day then fishbowled an igloo, taught her to play Take Two/Bananagrams. She's supposed to be taking me to my first strip club but that might be a while if it happens at all, she's going to Costa Rica for a month. So yeah, I've put in a bit of work that's amounted to no action. It's whatever though because I'm at least having a good time, and not turning in at the end of the night pissed about it.

[Donkey Lips]

Have you gotten laid more often by two women/three people involved more than one-on-one?

Expand Quote

then theres the vodka porn chick that went nowhere.

[close]

Strangely, same. She works as a promoter for an alcohol distributer and used to do porn. We went to some shitty local pub in a snowed in, dead town. No vibes were happening but we were getting along well. Before we even left I settled on just being friends, I had been on a few dates recently that amounted to nothing so I could read the signs. Also, if she worked in porn and was into me, I'd like to think it would be apparent. I paid and drove her home, had a small conversation in her driveway, hugged, and I zipped home because I hadn't slept since I got back from SF that day. Possible "FFFFUUUUUUUU" moment though, I think she was going in for a kiss when we hugged goodbye. She tilted her head ever-so-slightly as I aimed my chin straight for the shoulder, and grazed my cheek with a kiss that felt slighted--as though it wasn't intended for my cheek but elsewhere. I thought about it as I drove home but resigned myself to my tired mind.

We've hung out a few times since; treated her to a flick, I crashed in her guest room for a snow storm & went hiking the next day then fishbowled an igloo, taught her to play Take Two/Bananagrams. She's supposed to be taking me to my first strip club but that might be a while if it happens at all, she's going to Costa Rica for a month. So yeah, I've put in a bit of work that's amounted to no action. It's whatever though because I'm at least having a good time, and not turning in at the end of the night pissed about it.

Whoa now. Why is there no pic posted of this promoter and former porn chick! If you're putting in work it's time to get paid. Plus I want to see what this chick looks like on the internet.

[H8R part 4]

Have you gotten laid more often by two women/three people involved more than one-on-one?

nah, this is over span of 35 years of which i was having sex for 22 of them.  it breaks down to being asked once every 2 years or so and its not like i did it each time i was asked.  i think its just from living in the city.  theres a lot of weird crazed freaky people up in this piece.

the vodka porn chick is some girl that said she wanted to drink vodka and watch porn.  i posted the story on the other page of this thread.


       
this one is really bad...
i met this chick at the restaurant i worked at while i was in college.  she was a waitress there and she was smoking!   i was pretty forward back then so i didn't hesitate in asking her out right away.  she told me she had a BF but i flirted with her all the time anyway, it was all in fun and i just didn't give a fuck.  it didn't take long before she broke up with her BF and she asked me if i wanted to hang out after work.  so we start chillin and pal'ing around all the time, everywhere, we were attached at the hips, 2 peas in a pod,we became the best of friends.   
so months into this shit(and i mean months!), we finally hook up.  we started kissing, she reaches down my pants and starts stroking my cock, i reach down her pants and start fingering her.  everything is going great, i'm finally hooking up with this chick but for whatever reason i looked at her and said, "i don't want to do this if it isn't going to go anywhere"....wtf did i just say?!?!?  everything just grinds to a halt, it was like i bumped the turntables in the middle of a house party.  shes says she likes me but she just wants to have fun.  this was just unacceptable to me so i stopped, rolled over and went to sleep instead. 
the next day we wake up and shit is obviously super awkward.  i didn't know what to do or say from that moment on.  we eventually stopped hanging out and i never got to hook up with her again. 
i want to say i blew it but that doesn't even begin to describe my stupidity.  this is probably one of the only regrets i have in my life.     
         

[saucy ragu]

Oh just admit you can be a softie. That's probably the best decision you ever made, you told her what you wanted straight up and stuck with it. I'm actually sorry that didn't work out for you.

[H8R part 4]

Oh just admit you can be a softie. That's probably the best decision you ever made, you told her what you wanted straight up and stuck with it. I'm actually sorry that didn't work out for you.

i'll be the first one to admit that i'm a softie, i was young and in love but theres no reason to feel bad for me, this happened 15 years ago.  i facebooked her today, shes 39 now, married, has a kid and still looks really good. 
     

[Beeda Weeda]

met some fairly good looking girl at a friends bands gig, about 7-8 years ago, she was tall, thin, with a good ass and huge tits, i was excited to say the least.
so I hang out with her, watch almost famous in her parents basement (she was younger than I)
so we are fooling around and I go to take off her bra to unleash these massive brasts, I can barely control myself,
then the dreaded happens.
I feel somthing on her back...wtf is this i think to myself "could this be a dried up raisin stuck to her skin?" then i realize its probably the biggest mole I have ever felt, and my facial expressions ruined it all, the session was eneded and we never spoke again.

no that awkward, but i wanted to rip the mole off of her skin.

[brownjenkin]

my last "2 year relationship" after the first few months....what a waste of time girls can be.

I feel you on this one. That is a straight ticket to feeling like shit. When it's sitting there day after day, but no access, and you feel like you've won the lottery when the panties drop. It's hard to let go of that time in the beginning when everything was awesome and your dick felt like it had the power of Greyskull.

[nice weather]

met some fairly good looking girl at a friends bands gig, about 7-8 years ago, she was tall, thin, with a good ass and huge tits, i was excited to say the least.
so I hang out with her, watch almost famous in her parents basement (she was younger than I)
so we are fooling around and I go to take off her bra to unleash these massive brasts, I can barely control myself,
then the dreaded happens.
I feel somthing on her back...wtf is this i think to myself "could this be a dried up raisin stuck to her skin?" then i realize its probably the biggest mole I have ever felt, and my facial expressions ruined it all, the session was eneded and we never spoke again.

no that awkward, but i wanted to rip the mole off of her skin.

HAHAHAHAHA

[Bobbito]

Expand Quote

Oh just admit you can be a softie. That's probably the best decision you ever made, you told her what you wanted straight up and stuck with it. I'm actually sorry that didn't work out for you.

[close]

i'll be the first one to admit that i'm a softie, i was young and in love but theres no reason to feel bad for me, this happened 15 years ago.  i facebooked her today, shes 39 now, married, has a kid and still looks really good. 
     

pix plz. kthxbye

[Philosoraptor]

[Stoeipoes]

deh was fannie

[Ronald Wilson Reagan]

Faster, you lost your virginity with my fantasy- two girls at once... both 11 years old.

[spool of cord]

some reallly awkward shit happened to me at a prom party in my senior year. I'm from a tiny town in NY right on the pennslyvania border, and everyone from both schools in both states wanted to throw a huge banger considering both school's prom nights fell on the same day. everyone got together and picked a rural ass spot in PA for the party. And it was a banger indeed! Generators, five kegs, a huge sound system, beer pong, $300 worth of liquor, probably two hundred kids, a monsterous fire, drunk kids trying to shoot deer in the middle of the night in the woods...basically some out of control shit. everyone from both schools got a long, but the PA chicks were for the most part considered to be the better looking bunch. my friend's little sister, who had moved to nyc to go to school a few years before, came up and everyone was trying to get up in her shit. she started acting the part of super slut, and people are pouring honey over her tits around the fire and licking the shit out of them. my memory is pretty hazy but what happened after was almost absurd...I remember seeing that and being disgusted, so I took off from the main fire. Two of my friends from PA got a hold of someone's limo for prom, and I went to check up on them and I open the door and they're in there along with probably two other couples going at it like crazy. they freak on me to get out. mind you its probably 7 am at this point and the sun is starting to get to me. this other chick is out walking around, real imbred looking type, the type of girl no one ever wants to touch not because she's that ugly, but because her dad and brother would get jelous over you stealing their ass for the night. somehow this girl gets me in a car with her, and even though I'm wasted off my ass i'm still grossed out. all of a sudden out of no where she starts crying and screaming 'I CAN'T DO THIS!' like I'm some serial rapist. I ask her what the hell she's talking about and she goes 'I'm a virgin! a virgin! this is horrible!' needless to say the thought that she thought we were gonna bone skeezed me the fuck out and I hopped right out of that car. I keep walking around and run into my friend's little sister, the honey-tits slut I was talking about before. Considering she was single, cute, and had the mystique of being a 'city girl' she was the hot commodity of the night. Out of no where she's all over me, telling me how great of a guy I am and whatnot. I figure what any decent guy figures and scramble to get her into an unoccupied tent. Now its good to know that this girl is a ballerina, really fucking small body. I strip her down and start fingering her from behind, I remember being mildly surprised that her ass wasn't getting in my way. Seriously every thrust of my finger she's going apeshit like its her nuclear holocaust orgasm. I was loving it. I kept that up for awhile and then flipped her over on her back. I remember being pretty pissed that her tits were smaller than mine when I saw em, I guess she was barely sixteen and wore a push up bra, but still! anyway I decide to go down on her. first time I went down on anybody before, and her puss was top rank. I did that for about five minutes then she started begging me to put it in her. she was still shaking from me fingering her earlier that I figured the sex was gonna be beyond amazing. so i'm putting my dick in her, she looks down, and sits right up and says 'Hey you're not wearing a condom, wow you're such a fucking asshole!'

Her saying that sobered me right the fuck up. it was pathetic. after that, she kept dry humping me (and moaning over that!) for probably half an hour, but I was so fucking pissed and bummed out that it didn't do much for me. looking back now I feel like keithanne the incest baby was probably in way more of a pathetic spot than I was, but still. I learned a valuable lesson that night, even if it makes you look like an asshole, always carry condoms in your wallet, shirt and pants pockets, have em all over your car...its just not worth getting into shitty situations over not having one.

[Chris Hansen is back]

Faster, you lost your virginity with my fantasy- two girls at once... both 11 years old.

A seat. Take it.

[Joe Pesci]

yo chris hansen you got any pathetic and failed attempts @ sexual relations with the ladies?

[TheFreshSC]

about a year ago, when i was still with my costa rican chica, i experienced quite an unfortunate scenario.
i met her through her younger brother, a cool enough kid i whom would skate with just about every day. i was attempting to maintain a friendship with him while still hooking up with his sister multiple times a week.
One night, she texts me telling me that nobody is home (a very rare occurrence in that household), and that i should come over. I had not yet railed at this point, so by the time i had purchased some "dong bags" with which to "knock boots," i was starting to get fairly anxious.
I ring the doorbell and walk inside. I walk upstairs to find her just exiting the shower. I walk into her room and she tells me to wait a second so she can put on her new stuff from victoria's secrret. i tell her that's not necessary, but she comes over and pushes me out of her room, smiling mischievously. So now i'm standing outside her room for a few minutes. She opens the door wearing some tiny black panties and a black bra, grabs my hand, and leads me to the bed, where she proceeds to lay on her back in like a limp fish. At this point, i was aware that this was not the most "fit" girl i had ever been with. She had a really nice body, but wasn't as proactive as i had hoped. I get on top of her, still fully clothed, and we start making out. I take off my shirt, and immediately we hear the front door opening downstairs. I look at her and see an expression of panic. Her father resembles some sort of cross between a bear and a viking, and although her parents liked me, i wasn't trying to get on his bad side (or die, for that matter).
Someone storms up the stairs and starts pounding on the door. I stand up, hastily put on my shirt, and go to her bathroom, while she puts on sweatpants and a t shirt to open the door. Her little brother, who saw my shoes in the entryway, saw that we weren't in the living room, and did what any good brother would do, came upstairs to protect his sister. After i hear that it's him and not her beast of a father, i walk out of the bathroom and casually say, "oh, what up dude!" The kid wasn't stoked, and i felt pretty bad.
And i never ended up doing any ripping or tearing with this girl.

Me and her brother are still good friends now, but things haven't been quite the same.

[Sniper Rifle]

For the last 6 months every attempt at a sexual relationship has been pathetic for me. Oh well.

[mandibleclaw]

yo chris hansen you got any pathetic and failed attempts @ sexual relations with the ladies?

fuck no, chris hansen gets what chris hansen wants.

he's chris hansen.

[Ronald Wilson Reagan]

Expand Quote

Faster, you lost your virginity with my fantasy- two girls at once... both 11 years old.

[close]

A seat. Take it.

I'd be offended if it didn't offer. You sir, are the king of creating and broadcasting pathetic and failed attempts @ sexual relations.

[Bobbito]

Last January I was visiting my buddy in NY for the first time since he moved to a new apartment. He had told me previously that he was living with two girls, one of them who happened to be a babe as a friend of ours told me from having visited. Anyways, first night I'm there, I was just casually chatting up this roomate of his which led to all of us pregaming a good amount before heading out to some kids house. Me and this chick were totally clicking because she was a very free spirit, especially under the influence and I finally found a girl who I could jam out to 3 6 Mafia with haha. So we kick it at this dudes house later and I'm making a total drunken fool of myself the whole time which didn't seem to phase this girl really.
 � � �Next day, skate a bunch then go back to my boys house and this time I brought back a bottle of whiskey because this chick had told me that's what she likes to drink. Pregame again then go out to some bars. End up at Lit which I'm sure everyone on here who lives in the city knows the place's reputation for a good ass time. This chick and I start dancing and instantly making out and touching up on each other; at one point I was just pushing my hands all over her and she pushed them right onto her luscious boobs. We eventually walk back to her and my boys place, I carry her drunk ass up 3 flights of stairs and we settle down on the floor of the living room with blankets, pillows cushions, some snacks, and Hulu.

And then I wake up still fully dressed on that living room floor by myself.............

To say the least, I blew it entirely because this would have been the hottest girl I'd have hooked up with in my 21 years of existence. The worst part is she got a boyfriend not too long after, then dropped him over the summer and I totally made a negative drunken impression on her that night shortly after she ended things with her bf, and then she moved back to Miami. She's now back in NY for the weekend but my cunt coworker won't cover just 1 day so that I can go down to the city and finish what I had started. I don't want to get ahead of myself and assume but when I texted her that I won't make it this weekend, I got a frowny face back so maybe she's still down but who the fuck knows. At this point its very much whatever since we live so far from each other, but it still bugs me to this day that it didn't go down like it should have.

edit: here's a pic since I'm sure someones going to ask

[saucy ragu]

and she pushed them right onto her luscious boobs.

AHAHAHAHA Bob is it bad I can tell you're drunk as you write this because of the way you wrote this? Ahahahahah "luchuss bewbs."

[Donkey Lips]

some reallly awkward shit happened to me at a prom party in my senior year. I'm from a tiny town in NY right on the pennslyvania border, and everyone from both schools in both states wanted to throw a huge banger considering both school's prom nights fell on the same day. everyone got together and picked a rural ass spot in PA for the party. And it was a banger indeed! Generators, five kegs, a huge sound system, beer pong, $300 worth of liquor, probably two hundred kids, a monsterous fire, drunk kids trying to shoot deer in the middle of the night in the woods...basically some out of control shit. everyone from both schools got a long, but the PA chicks were for the most part considered to be the better looking bunch. my friend's little sister, who had moved to nyc to go to school a few years before, came up and everyone was trying to get up in her shit. she started acting the part of super slut, and people are pouring honey over her tits around the fire and licking the shit out of them. my memory is pretty hazy but what happened after was almost absurd...I remember seeing that and being disgusted, so I took off from the main fire. Two of my friends from PA got a hold of someone's limo for prom, and I went to check up on them and I open the door and they're in there along with probably two other couples going at it like crazy. they freak on me to get out. mind you its probably 7 am at this point and the sun is starting to get to me. this other chick is out walking around, real imbred looking type, the type of girl no one ever wants to touch not because she's that ugly, but because her dad and brother would get jelous over you stealing their ass for the night. somehow this girl gets me in a car with her, and even though I'm wasted off my ass i'm still grossed out. all of a sudden out of no where she starts crying and screaming 'I CAN'T DO THIS!' like I'm some serial rapist. I ask her what the hell she's talking about and she goes 'I'm a virgin! a virgin! this is horrible!' needless to say the thought that she thought we were gonna bone skeezed me the fuck out and I hopped right out of that car. I keep walking around and run into my friend's little sister, the honey-tits slut I was talking about before. Considering she was single, cute, and had the mystique of being a 'city girl' she was the hot commodity of the night. Out of no where she's all over me, telling me how great of a guy I am and whatnot. I figure what any decent guy figures and scramble to get her into an unoccupied tent. Now its good to know that this girl is a ballerina, really fucking small body. I strip her down and start fingering her from behind, I remember being mildly surprised that her ass wasn't getting in my way. Seriously every thrust of my finger she's going apeshit like its her nuclear holocaust orgasm. I was loving it. I kept that up for awhile and then flipped her over on her back. I remember being pretty pissed that her tits were smaller than mine when I saw em, I guess she was barely sixteen and wore a push up bra, but still! anyway I decide to go down on her. first time I went down on anybody before, and her puss was top rank. I did that for about five minutes then she started begging me to put it in her. she was still shaking from me fingering her earlier that I figured the sex was gonna be beyond amazing. so i'm putting my dick in her, she looks down, and sits right up and says 'Hey you're not wearing a condom, wow you're such a fucking asshole!'

Her saying that sobered me right the fuck up. it was pathetic. after that, she kept dry humping me (and moaning over that!) for probably half an hour, but I was so fucking pissed and bummed out that it didn't do much for me. looking back now I feel like keithanne the incest baby was probably in way more of a pathetic spot than I was, but still. I learned a valuable lesson that night, even if it makes you look like an asshole, always carry condoms in your wallet, shirt and pants pockets, have em all over your car...its just not worth getting into shitty situations over not having one.

You from Waverly man?

Edit - Bob +1 for still getting at least some action with that chick.

[StabMasterArson]

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"dong bags"

[close]

"hey babe, want me to pick up a box of dong bags incase we decide to knock boots later?"

[heckler]

For the last year every attempt at a sexual relationship has been pathetic for me. Oh well.

[H8R part 4]

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Oh just admit you can be a softie. That's probably the best decision you ever made, you told her what you wanted straight up and stuck with it. I'm actually sorry that didn't work out for you.

[close]

i'll be the first one to admit that i'm a softie, i was young and in love but theres no reason to feel bad for me, this happened 15 years ago.  i facebooked her today, shes 39 now, married, has a kid and still looks really good. 
     

[close]

pix plz. kthxbye

this is her with her kid...

and a blurry webcam pic.....

Expand Quote

Faster, you lost your virginity with my fantasy- two girls at once... both 11 years old.

[close]

A seat. Take it.

i was 13 nothing illegal about it. 
this is a pic of one of the girls...

i tried looking for the other girl but it started turning into a easter egg hunt.