Author Topic: Awkward Sexual Experiences  (Read 462885 times)

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pugmaster

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Re: Awkward Sexual Experiences
« Reply #2160 on: September 27, 2020, 08:03:41 AM »
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oh fuck, oh man, oh shit. the other night i hooked up with a heavy goth chick and while we were doing 69 she squirted so much pickle juice down my throat. gnarliest fucking moment of my life. threw her off me and could not get hard again for the rest of the night.
fucking RIP
[close]

As a BBW fan myself, I have had mixed experience with squirters. In some cases everything is hunky dory.  In other cases it is straight up urine.
[close]

She didnt even cum, just channeled the great fucking flood into me. im fine with squirters but it was like swallowing a blast of salt water swimming in the ocean- fucked me up yo.

That is in no way, shape, or form shalom.
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Re: Awkward Sexual Experiences
« Reply #2161 on: September 28, 2020, 12:23:34 AM »
new sheets feel great- am i right

mynameisnotjeff

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Re: Awkward Sexual Experiences
« Reply #2162 on: September 28, 2020, 07:28:39 PM »
new sheets feel great- am i right
Silk or anything smooth like that sucks. It will have you slipping everywhere. Once I hurt my knee skating and thought I was going to blow my ACL out.
Nothing I do deserves more than an iphone camera.

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Re: Awkward Sexual Experiences
« Reply #2163 on: October 20, 2020, 06:27:11 AM »
I'll bite...

I had recently broken up with a long term girlfriend. Despite knowing her and I would never work out(she resented me for cheating, lots of trauma between us, blah  blah blah). I was on a big kick of trying to fuck chicks. Made a tinder, the whole nine. Anyway, I'm downtown in the city and listening to this great jazz band play and see this chick staring at me. She was darker skinned, a little thick but really put together. I ended up growing the balls to chat with her, she was obviously thirsty, we talked and then had a couple drinks and then I asked her to come back to my place.

Honestly, I'm very sexually experienced but I really prefer to have some rapport with the person and when I don't I get pretty nervous. I was shaky with her and obviously nervous but we started hooking up. Went over to the bed, fucked around and I just couldn't get it up. I found her so unattractive with her clothes off and she had told me all this fucked up shit. Like she was mid 20's but had three kids and her ex threw her down the stairs when she was pregnant so the one kid is regular now. I hate kids and never want to have them but it really fucked with my head and I just couldn't fuck her. I ended up walking her to her car and the worst part was that some good looking Puerto Rican guy came up and like obviously oggled at her and said some shit like I hope he's treating you right and obviously I wasn't lol.

It was a total mess but I felt like I had to redeem myself so I texted her after like a week and she came back over and honestly her pussy was so gross smelling. I fucked her for a little but just couldn't bust. Ended up walking her home and she was talking about how she wanted someone who would take care of her kids and shit and I played along but obviously the night was dead.

It was a fucked situation. I went home to lay in bed and I could smell her still and I started dry heaving, then crying because of how much of a mess my life was at the time.

Luckily I had some good tail a month or two later. Ended up hooking up with some girl I always wanted to hook up with and she had told me she wasn't going to cum because of all the wine we drank, then I made her cum eating her out from behind. It was cool. Except she had forgotten to take her seizure medication and ended up having one at work later, calling me up after it was done to fuck her again, but her pussy was too swollen from the night before and she asked me to stop. So, I guess that was kind of another awkward sexual experience too but at least I didn't want to puke or cry afterwards.

Grind King Rims

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Re: Awkward Sexual Experiences
« Reply #2164 on: October 20, 2020, 12:42:54 PM »
Shit happens man. All you can do is try to laugh! Good story

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Re: Awkward Sexual Experiences
« Reply #2165 on: October 20, 2020, 06:57:41 PM »
Was hooking up with a BBW who had a tattoo of a stick figure pushing a lawnmower on her bush.

When I noticed, I half laughed, half wondered why anyone would go that far with a joke and entirely lost my boner. Anything that causes thought during sex destroys my concentration.

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Re: Awkward Sexual Experiences
« Reply #2166 on: October 20, 2020, 07:33:15 PM »
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Well lads, it's been a while, so the old boy Grind King Rims will regale a tale of a huuuuuge fucking mistake.

When I was about 20/21, I was staying at home in the countryside with my family. I was still deeply closeted and hated my gay sexual urges. My go-to wasn't Grindr, but Craigslist Casual Encounters. I got in contact with some sketchy old guy from a few country towns over. All of these towns have populations of hundreds of people, not thousands: as rural as it gets. I can't remember the details of chatting with this guy, but somewhere along the way he mentions that he has a fantasy of being a schoolmaster and getting with a guy in school uniform. I offered to wear my old school uniform, but thank Christ almighty he said it wasn't necessary because my dumb faggot ass would have done it.

I ended up ordering a rural taxi bus to get me over there. My family was suspicious as to why I was leaving suddenly in the night, and even the taxi driver was wondering why I was getting a taxi to a tiny remote village. When I met the guy, he was shorter than me, maybe 5'3" and from what little I could see on the side road with no street lights, he was absolutely disgusting. He looked like the Yellow King from True Detective , but shorter. I was too uncomfortable and inexperienced to just say, "Yeah this isn't happening man, I'm not into it." So instead I went with him down a country road to the shed where his family kept the cattle, where he had a tiny cot, a 12" TV/VHS combo playing porn (he apologized for only having straight porn). He had a tiny disgusting penis. We 69'd for about a minute, maybe less, before he said really casually, with almost no inflection in his voice, "Don't worry, I'm just cumming there." and came in my mouth. I got the same confused, suspicious taxi driver to take me home immediately, less than a half an hour after he dropped me off I'm sure.

It's probably the most disgusting and unpleasant sexual experience I've ever had. I remember feeling like I had volunteered myself to be molested. I don't think I jacked off or felt sexy for well over a week after and I've never told anyone about it until now.
[close]

This is incredibly depressing. Being made to think your most basic urges are wrong leads to some fucked up shit. Thanks for sharing.
Damn man. This is how so many serial killers first victims were killed. I am seriously at a loss and can't stop smiling about how creepy that is.

Not by you if that makes sense, but what you had to go through. Thank god you are still alive.

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Re: Awkward Sexual Experiences
« Reply #2167 on: October 23, 2020, 10:38:55 AM »
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Well lads, it's been a while, so the old boy Grind King Rims will regale a tale of a huuuuuge fucking mistake.

When I was about 20/21, I was staying at home in the countryside with my family. I was still deeply closeted and hated my gay sexual urges. My go-to wasn't Grindr, but Craigslist Casual Encounters. I got in contact with some sketchy old guy from a few country towns over. All of these towns have populations of hundreds of people, not thousands: as rural as it gets. I can't remember the details of chatting with this guy, but somewhere along the way he mentions that he has a fantasy of being a schoolmaster and getting with a guy in school uniform. I offered to wear my old school uniform, but thank Christ almighty he said it wasn't necessary because my dumb faggot ass would have done it.

I ended up ordering a rural taxi bus to get me over there. My family was suspicious as to why I was leaving suddenly in the night, and even the taxi driver was wondering why I was getting a taxi to a tiny remote village. When I met the guy, he was shorter than me, maybe 5'3" and from what little I could see on the side road with no street lights, he was absolutely disgusting. He looked like the Yellow King from True Detective , but shorter. I was too uncomfortable and inexperienced to just say, "Yeah this isn't happening man, I'm not into it." So instead I went with him down a country road to the shed where his family kept the cattle, where he had a tiny cot, a 12" TV/VHS combo playing porn (he apologized for only having straight porn). He had a tiny disgusting penis. We 69'd for about a minute, maybe less, before he said really casually, with almost no inflection in his voice, "Don't worry, I'm just cumming there." and came in my mouth. I got the same confused, suspicious taxi driver to take me home immediately, less than a half an hour after he dropped me off I'm sure.

It's probably the most disgusting and unpleasant sexual experience I've ever had. I remember feeling like I had volunteered myself to be molested. I don't think I jacked off or felt sexy for well over a week after and I've never told anyone about it until now.
[close]

This is incredibly depressing. Being made to think your most basic urges are wrong leads to some fucked up shit. Thanks for sharing.
[close]
Damn man. This is how so many serial killers first victims were killed. I am seriously at a loss and can't stop smiling about how creepy that is.

Not by you if that makes sense, but what you had to go through. Thank god you are still alive.

Hahahaha, good, I'm glad it made you smile. I tried to write it with a bit of humor, because it's behind me now, but yeah, that was so fucked, hahaha.

Mesteezo

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Re: Awkward Sexual Experiences
« Reply #2168 on: October 27, 2020, 11:07:14 AM »
I used to play pop warner football as a kid, and for the first half of my first season I was a center. That means I had hands up against my balls and gooch because I was the one hiking the ball to the quarterback. It was never comfortable, always awkward especially on game days where the whole crowd is watching my no-no zone get diddled.

Obviously it's not a sexual act, but it was the first time I had my erogenous zone touched by another person. Playing offensive line fucking sucks, I switched to D-line after and got to hit kids as hard as I wanted  :)


For reference...

Owen

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Re: Awkward Sexual Experiences
« Reply #2169 on: October 29, 2020, 01:46:48 AM »
I used to play pop warner football as a kid, and for the first half of my first season I was a center. That means I had hands up against my balls and gooch because I was the one hiking the ball to the quarterback. It was never comfortable, always awkward especially on game days where the whole crowd is watching my no-no zone get diddled.

Obviously it's not a sexual act, but it was the first time I had my erogenous zone touched by another person. Playing offensive line fucking sucks, I switched to D-line after and got to hit kids as hard as I wanted  :)


For reference...


I don't really know anything about American Football but this sounds a bit... gay?
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Re: Awkward Sexual Experiences
« Reply #2170 on: October 29, 2020, 03:09:47 PM »
Oh, one time a guy ejaculated blood onto my chest.

ihatejulio

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Re: Awkward Sexual Experiences
« Reply #2171 on: October 29, 2020, 04:46:27 PM »
Oh, one time a guy ejaculated blood onto my chest.

Probably from sacking the rail.

 ;)

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Re: Awkward Sexual Experiences
« Reply #2172 on: October 29, 2020, 05:29:12 PM »
Oh, one time a guy ejaculated blood onto my chest.
please tell me he was singing/ grunting this when it happened:

Impish sausage is definitely gonna blow up as a euphemism this year

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Re: Awkward Sexual Experiences
« Reply #2173 on: October 31, 2020, 05:06:21 AM »
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Oh, one time a guy ejaculated blood onto my chest.
[close]

Probably from sacking the rail.

 ;)

Nice, hahaha.

Nah, he put it down to some dodgy herbal supplement that he took right before. Some libido enhancer shit. It was really fucking weird, but I thought it was funny. It was the first time I got with him, he's ended up being a good friend and fuck buddy for the past 5 years. He said it never happened before and it's definitely never happened with him since. He gets bummed any time I bring it up, but I think it's so gnarly and funny.

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Re: Awkward Sexual Experiences
« Reply #2174 on: October 31, 2020, 05:10:07 AM »
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Oh, one time a guy ejaculated blood onto my chest.
[close]
please tell me he was singing/ grunting this when it happened:


Napalm Death >>> Cannibal Corpse (for me)

But I appreciate the post all the same <3

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Re: Awkward Sexual Experiences
« Reply #2175 on: October 31, 2020, 05:20:43 AM »
Of course ND are better than CC; ND has political lyrics/ basically invented grind, CC just happened to find a medical dictionary. Either way, he came blood!!!!

Impish sausage is definitely gonna blow up as a euphemism this year

matty_c

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Re: Awkward Sexual Experiences
« Reply #2176 on: October 31, 2020, 06:48:25 AM »
lego sword in urethra selfpwn
you know how you don’t remember shit from childhood well I remember that

not fucken doing that again that was sketchy

still tho, I walked through the storm with my head held high cause I’m not afraid of the dark
listen to cosmic psychos

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Re: Awkward Sexual Experiences
« Reply #2177 on: October 31, 2020, 07:22:48 AM »
I'm afraid of heights but an ex gf was really into graffiti and getting up on dodgy roofs and climbing etc. I didn't want to embarrass myself and chicken out when she invited me to hang on a nearby rooftop so I went along with it. Anyway we had to make our way across this sketchy skinny little beam to cross over to the spot and I legit shed a tear or two making my way across. I was trying to hide it really hard once we reached the other side and she asked what was wrong as I was trembling and couldn't make eye contact. I just blurted out " i'm so happy when i'm with you " and started making out with her. She was wearing these leather gloves and ended up jerking me off with them. The post fear orgasm was fantastic.
I've had a glove fetish ever since and i'm not as scared of heights anymore. Conquer your fears everyone.

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Re: Awkward Sexual Experiences
« Reply #2178 on: October 31, 2020, 08:22:34 AM »
I'm afraid of heights but an ex gf was really into graffiti and getting up on dodgy roofs and climbing etc. I didn't want to embarrass myself and chicken out when she invited me to hang on a nearby rooftop so I went along with it. Anyway we had to make our way across this sketchy skinny little beam to cross over to the spot and I legit shed a tear or two making my way across. I was trying to hide it really hard once we reached the other side and she asked what was wrong as I was trembling and couldn't make eye contact. I just blurted out " i'm so happy when i'm with you " and started making out with her. She was wearing these leather gloves and ended up jerking me off with them. The post fear orgasm was fantastic.
I've had a glove fetish ever since and i'm not as scared of heights anymore. Conquer your fears everyone.

God damn, boy called an audible last minute and succeeded.



I salute you sir

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Re: Awkward Sexual Experiences
« Reply #2179 on: October 31, 2020, 08:51:11 AM »
I'm afraid of heights but an ex gf was really into graffiti and getting up on dodgy roofs and climbing etc. I didn't want to embarrass myself and chicken out when she invited me to hang on a nearby rooftop so I went along with it. Anyway we had to make our way across this sketchy skinny little beam to cross over to the spot and I legit shed a tear or two making my way across. I was trying to hide it really hard once we reached the other side and she asked what was wrong as I was trembling and couldn't make eye contact. I just blurted out " i'm so happy when i'm with you " and started making out with her. She was wearing these leather gloves and ended up jerking me off with them. The post fear orgasm was fantastic.
I've had a glove fetish ever since and i'm not as scared of heights anymore. Conquer your fears everyone.

This is the beautiful love story that could singlehandedly save Penthouse Forum <3

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Re: Awkward Sexual Experiences
« Reply #2180 on: October 31, 2020, 08:01:20 PM »
In 2012 was living the dirty kid life, traveling the states, clipping bud, sleeping outside or on a couch, getting hammered and having a blast. I was also really into yoga and on a celibacy kick. I'd decided that after having sex with too many of my female friends and changing the dynamics of relationship I needed to stop fucking for a while. Then comes Halloween. I'd met this girl from Eugene at a squat, we kinda hit it off, took off into the dunes and made out for a while. There was a party that we made it over to and drank fireball whiskey. We weren't really getting along but I invited her back to a friends house where I had a hammock strung up out back. Somehow we both fit into the hammock and started making out again when she starts rubbing me off. I'm like "woah, hang on a second" and we both end up getting our pants down to the ankles and fucking. Man, I'll never forget how silky that pussy felt after living the drunk monk life for a year. Of course, I bust my nut in under a minute. I go to get up out of the hammock and with my pants around the ankles step barefoot into a big piles of dog shit. Stinky stinky dog shit. Drunk, dark, half naked and stinking like dog shit on Halloween.

We didn't get along well at all but ended up traveling for the next few months, banging like 5x a day, wherever we could. Amtrak trains, alleys, garages, grow scenes, cars, my childhood bedroom, the side of the freeway. Shit was awkward, every single time, because as soon as we were done it was like "again? really?"

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Re: Awkward Sexual Experiences
« Reply #2181 on: November 01, 2020, 04:09:59 AM »
Thread has picked up recently. Good posts, gang.

matty_c

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Re: Awkward Sexual Experiences
« Reply #2182 on: November 01, 2020, 06:08:08 AM »
This isn’t really a sexual experience but whatever, so there’s this pretty girl lives on same floor as me and she’s always super friendly, my dog likes her too
anyway I was coming home the other night, absolutely fuck eyed and I got off the train and was walking through the station. I did a tremendous burp and I remember thinking fuck that stinks. Shit comes into focus for me and it’s fucking her and her friend coming right at me walking through the miasma of what came from my guts
I swear to god it made the air shimmer
She looked so disappointed honestly I’d have been better off if I shit myself in front of her

I had been drinking rum punch and I had polished off one of those charcuterie boards earlier so yeah it was a fucking seedy burp
I could almost hear her vagina clang shut
listen to cosmic psychos

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Re: Awkward Sexual Experiences
« Reply #2183 on: November 02, 2020, 05:11:36 AM »
Of course ND are better than CC; ND has political lyrics/ basically invented grind, CC just happened to find a medical dictionary. Either way, he came blood!!!!

No doubt. But remember Jeff did the cover art for scum and that bill was the guitarist for the b side.


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Re: Awkward Sexual Experiences
« Reply #2184 on: November 04, 2020, 06:40:44 AM »
Most of my sexual encounters are awkward but I’ll go with the time I took a Xanax and drank a forty....

I grew up in a small town in Texas called palacios, there isn’t much to do, it is a coastal town so there was a sea wall and a couple other small Rinky dink places to skate, so  not much to do if your a kid unless it’s party. Anyways I was a little more inexperienced with pharmaceutical drugs when I was younger and a friend of mine gave me yellow football, to which I ate without thinking twice, how could something so small do anything to me??? So we hear about this party this girl is having at her and her boyfriends place, the dude is gone with his parents to some funeral or something of that nature. We get to the party and it’s already getting crazy, the pill I had taken started working and I began to feel a little loose and more talkative, I’m usually not one to spark up conversations or anything but I became quite the babble mouth. Someone had purchased a 12 pack of forties and someone handed me one not knowing that the pill and the forty is really gonna make this quite possible one of the most embarrassing nights of my life, I’m about 150 on a good day, so one forty is already gonna make me feel some type of way but you add a benzo in the mix...whew I’m fucked, the girl who was hosting this party had always had a thing for me and we always were flirty but she always had a dude and I’m kind of a stickler for being faithful, we end up kicking it talking about bands or some shit movies or whatever the fuck I go on about, this is where things get blurry... we end up making out and messing around or whatever, and things end up happening so we go look around for an empty bedroom at this house her and her dude were renting, she didn’t wanna go into their bedroom but there two more in the house, the first one is occupied with some people doing coke so we go to this other one and I remember walking into one door and seeing like two more on the other side of the room, like the double doors that open up together, and I was like man three doors into this one room wierd (this come into play later) so whatever we get down to business start fucking and whatnot, she pretty loud and even though there was a party I was still concerned about someone hearing, I didn’t wanna get caught up, so we switch positions and I start smashing her from behind, smacking her ass and she’s moaning and shit just having a good time, then I hear someone at the big double doors “you hear that?” BOOM they slam open and the entire party is looking at me smashing this chick from behind buck naked, I guess those door opened up into the living room and this room was an office the converted to a bedroom, anyways I continued to fuck this chick as the party watched for a good 15 seconds with no concern..because of the Xanax, the person who opened the door shut it... and we finished up, but so now every once and awhile when I go visit my hometown someone usually brings up the time in high school the entire school saw my stroke game....but I never had a problem getting women the rest of the time I was in school, so I guess it started out as an awkward story but ended up a positive story..... getting girls out of high school was a lot harder come to find out
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Re: Awkward Sexual Experiences
« Reply #2185 on: November 04, 2020, 02:57:47 PM »
This isn’t really a sexual experience but whatever, so there’s this pretty girl lives on same floor as me and she’s always super friendly, my dog likes her too
anyway I was coming home the other night, absolutely fuck eyed and I got off the train and was walking through the station. I did a tremendous burp and I remember thinking fuck that stinks. Shit comes into focus for me and it’s fucking her and her friend coming right at me walking through the miasma of what came from my guts
I swear to god it made the air shimmer
She looked so disappointed honestly I’d have been better off if I shit myself in front of her

I had been drinking rum punch and I had polished off one of those charcuterie boards earlier so yeah it was a fucking seedy burp
I could almost hear her vagina clang shut

Hahaha amazing.
Bro those charcuterie boards are good shit, thats my take away from all this.


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Re: Awkward Sexual Experiences
« Reply #2186 on: November 09, 2020, 03:52:37 AM »
This isn’t really a sexual experience but whatever, so there’s this pretty girl lives on same floor as me and she’s always super friendly, my dog likes her too
anyway I was coming home the other night, absolutely fuck eyed and I got off the train and was walking through the station. I did a tremendous burp and I remember thinking fuck that stinks. Shit comes into focus for me and it’s fucking her and her friend coming right at me walking through the miasma of what came from my guts
I swear to god it made the air shimmer
She looked so disappointed honestly I’d have been better off if I shit myself in front of her

I had been drinking rum punch and I had polished off one of those charcuterie boards earlier so yeah it was a fucking seedy burp
I could almost hear her vagina clang shut

I burped inside a girls mouth this summer

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Re: Awkward Sexual Experiences
« Reply #2187 on: December 08, 2020, 02:43:39 PM »
I was hanging out with this woman who I think is the cutest lady ever... she had to quarantine for a few weeks due to someone she is close with getting covid. The day she was free from quarantine we spent the day touring the city, shooting with my super8 camera, and then we went back to my place for dinner/movie.

After starting the movie and we go straight to making out. As mentioned above, I'm super into her and we couldn't hang out due to covid for a couple weeks, so I eagerly go down on her in the dark, we fool around, finish up and get ready to hop in the shower. We flip on the lights and there is a good amount of blood on the sheets... fuck, her period started a little early.

Usually, no big deal, toss the sheets into the washer, rinse off, and move on with the night. However, considering we weren't super deep into a relationship, I'm sketched out that I went down on her at that time of the month... seems like a little too much bodily fluid contact (I didn't even do that shit with my ex who I was with for nearly a decade).



As for a more traditional awkward experience, in HS my gf and I had no where to make out. So we'd usually fool around at her community pool (I can't believe we never got arrested), the park, a parking lot, wherever. One night there were people at the pool so we move to the adjacent park. Eventually, I'm on the bench and she is kneeling in front of me... and this old guy walks up and barks, "Hey, you kids!..." She takes off running and I'm running after her with my dick flopping around.  Luckily, the old man did not put much effort into the chase and we were able to escape.
« Last Edit: December 08, 2020, 03:37:59 PM by TheLurper »

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nevrwasben

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Re: Awkward Sexual Experiences
« Reply #2188 on: December 08, 2020, 02:55:29 PM »
I was hanging out with this woman who I think is the cutest lady ever... she had to quarantine for a few weeks due to someone she is close with getting covid. The day she is free from quarantine we spend the day touring the city, shooting with my super8 camera, and then we go back to my place for dinner/movie.

Start the movie and go straight to making out. As mentioned above, I'm super into her and we couldn't hang out due to covid for a couple weeks, so I eagerly go down on her in the dark, we fool around, finish up and get ready to hop in the shower. We flip on the lights and there is a good amount of blood on the sheets... fuck, her period started a little early. Usually, no big deal, toss the sheets into the washer, rinse off, and move on with the night. However, considering we weren't super deep into a relationship I'm certainly sketched out I went down on her at that time of the month... seems like a little too much bodily fluid contact (I didn't even do that shit with my ex who I was with for nearly a decade).
What’s done is done, if she’s as cool as you are hoping just chalk it up to bad timing and keep hanging out w/her. Maybe she’ll even “owe you one”

Manny Fapuiao

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Re: Awkward Sexual Experiences
« Reply #2189 on: December 08, 2020, 04:16:39 PM »
Back in freshman year of high school, my first gf and I would sneak around and get frisky in stealthy locations. One of these locations was the roof of a theater nearby her dad's house. This particular day she was giving me a bj, which was quite enjoyable until my wiener hit the bracket of her braces in the back of her mouth. Having never experienced such a profoundly painful sensation, I lost all bodily control. Ended up peeing a whole lot in her mouth and we didn't talk for a few days.
I've had a better understanding of what is happening around me while smoking Salvia as a passenger in a moving vehicle than reading your post