Awkward Sexual Experiences

[lilboosie]

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not yet, but this could lead to an awk sexual encounter

i matched with someone who just moved in with her sister. we are planning on hanging out.

got a match this morning and in my head i think she looks like the girl im supposed to hangout with(ill call her kim) . it was a joke in my head but my eyes finally wake up and i see what looks like the same bathroom. ok could just be similar layout. nope its the same exact one. the curtain and lights confirmed it aha. its kims older sister.

i had planned to ask kim if it was her sister, but ..... what if i just see what happens. a risky move. probably should be in the tinder thread but ill use this a place holder cause i think things might get awkward. considering posting screen grabs (no faces) to get some confirmation

[close]

I’m hooked already. Go on and take the risky plunge, lb.

the balls already rolling. its still early here so i will have to wait till tonight probably to get some development

[DaleSr]

not yet, but this could lead to an awk sexual encounter

i matched with someone who just moved in with her sister. we are planning on hanging out.

got a match this morning and in my head i think she looks like the girl im supposed to hangout with(ill call her kim) . it was a joke in my head but my eyes finally wake up and i see what looks like the same bathroom. ok could just be similar layout. nope its the same exact one. the curtain and lights confirmed it aha. its kims older sister.

i had planned to ask kim if it was her sister, but ..... what if i just see what happens. a risky move. probably should be in the tinder thread but ill use this a place holder cause i think things might get awkward. considering posting screen grabs (no faces) to get some confirmation

I've kissed two different sisters before. It was fun

[lilboosie]

@DaleSr at the same time? or

[DaleSr]

@DaleSr at the same time? or

Nah was seeing one on and off but shit faded away. Younger sister and i matched on tinder like a year later, we went out and she was talking mad shit about her sister. We made out in the parking lot and she was a way better kisser haha

[lilboosie]

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@DaleSr at the same time? or

[close]

Nah was seeing one on and off but shit faded away. Younger sister and i matched on tinder like a year later, we went out and she was talking mad shit about her sister. We made out in the parking lot and she was a way better kisser haha

damn and she was shit talking her sister. did you worry about saying the wrong name?

[DaleSr]

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@DaleSr at the same time? or

[close]

Nah was seeing one on and off but shit faded away. Younger sister and i matched on tinder like a year later, we went out and she was talking mad shit about her sister. We made out in the parking lot and she was a way better kisser haha

[close]

damn and she was shit talking her sister. did you worry about saying the wrong name?

Nah my lips were busy making out with her, i wasn't trying to use my words while we were kissing

[lilboosie]

OK the older sister is messaging back. We have reached a new development

This is at the same time the other sister is messaging me.

I think I crossed the point where there's gonna be a good outcome from this. Or..

[Frank]

OK the older sister is messaging back. We have reached a new development

This is at the same time the other sister is messaging me.

I think I crossed the point where there's gonna be a good outcome from this. Or..

i suggest the two sisters engage in hand to hand combat to decide who's getting the date

EDIT: or maybe settle it with a competitive round of mario kart

hand to hand combat just sounded badass, but is probably a bit much to expect this early in the development

[lilboosie]

Expand Quote

OK the older sister is messaging back. We have reached a new development

This is at the same time the other sister is messaging me.

I think I crossed the point where there's gonna be a good outcome from this. Or..

[close]

i suggest the two sisters engage in hand to hand combat to decide who's getting the date

EDIT: or maybe settle it with a competitive round of mario kart

hand to hand combat just sounded badass, but is probably a bit much to expect this early in the development

My ideal situation would be something like Brett micheals rock of love. Like a date with both where I'm trying to get to know both at the same time on a date. But they are sisters so I think they would just agree to drop me.

[BALARGUE]

Expand Quote

Expand Quote

OK the older sister is messaging back. We have reached a new development

This is at the same time the other sister is messaging me.

I think I crossed the point where there's gonna be a good outcome from this. Or..

[close]

i suggest the two sisters engage in hand to hand combat to decide who's getting the date

EDIT: or maybe settle it with a competitive round of mario kart

hand to hand combat just sounded badass, but is probably a bit much to expect this early in the development

[close]

My ideal situation would be something like Brett micheals rock of love. Like a date with both where I'm trying to get to know both at the same time on a date. But they are sisters so I think they would just agree to drop me.

pornhub considers there is another ideal situation

[Turtle Boy]

Expand Quote

Expand Quote

Expand Quote

OK the older sister is messaging back. We have reached a new development

This is at the same time the other sister is messaging me.

I think I crossed the point where there's gonna be a good outcome from this. Or..

[close]

i suggest the two sisters engage in hand to hand combat to decide who's getting the date

EDIT: or maybe settle it with a competitive round of mario kart

hand to hand combat just sounded badass, but is probably a bit much to expect this early in the development

[close]

My ideal situation would be something like Brett micheals rock of love. Like a date with both where I'm trying to get to know both at the same time on a date. But they are sisters so I think they would just agree to drop me.

[close]

pornhub considers there is another ideal situation

I need daily updates of this story

[Sativa Lung]

Not really funny awkward but I'm currently being sexually harassed by a woman I work with. She's in her 50s so like 15-20 years older than me but would have probably been a smoke show in her younger days (her 20something daughter is a solid 8/10) and I'm guessing she's not used to men not being interested in at least fucking her.

Its pretty much your standard "oops I tripped and grabbed your ass to steady myself" or trying to rub my shoulders or back kinda shit along with just basic attention seeking behavior. It honestly reminds me of the way girls would act in high school when they liked you but were too embarrassed to ask you out.

I'm not going to report her because it doesn't really bother me - on some level I probably enjoy the attention if I'm being totally honest with myself - and I really think its at least somewhat down to her not knowing how to handle someone not being interested. Most of the dudes we work with are old horndogs who would kill a puppy to get in her scrubs.

I've told her it aint happenin but I could probably communicate it more clearly and bluntly. I've also thought about telling her I'm gay but I don't think she'd believe it as I had a thing with one of her (much younger) former co-workers years ago when I was still just a patient and not working at the hospital yet. I'm also a bit of a greedy amoral scumbag so I've considered offering it up for a price. She's been an RN for decades and her only kid is grown and out of the house, so I'm sure she's got a fair amount of income she could spend on "entertainment". I've done far worse to pay my rent in the past and I don't think she wants anything beyond a thorough dicking.

[lilboosie]

Don't have an update. Am/was supposed to meet up with the younger sister this weekend.


But slap I got in a pickle. I hooked up with someone. Who made it seem like it was an open relationship. It isn't.

I should have confirmed before and not during.

What have I gotten myself into.  I'd be lying if it wasn't great. But that hit like a sack of potatoes.

This probably sounds like bs but I wish it was.

[Dr-Feelgood]

Not really funny awkward but I'm currently being sexually harassed by a woman I work with. She's in her 50s so like 15-20 years older than me but would have probably been a smoke show in her younger days (her 20something daughter is a solid 8/10) and I'm guessing she's not used to men not being interested in at least fucking her.

Its pretty much your standard "oops I tripped and grabbed your ass to steady myself" or trying to rub my shoulders or back kinda shit along with just basic attention seeking behavior. It honestly reminds me of the way girls would act in high school when they liked you but were too embarrassed to ask you out.

I'm not going to report her because it doesn't really bother me - on some level I probably enjoy the attention if I'm being totally honest with myself - and I really think its at least somewhat down to her not knowing how to handle someone not being interested. Most of the dudes we work with are old horndogs who would kill a puppy to get in her scrubs.

I've told her it aint happenin but I could probably communicate it more clearly and bluntly. I've also thought about telling her I'm gay but I don't think she'd believe it as I had a thing with one of her (much younger) former co-workers years ago when I was still just a patient and not working at the hospital yet. I'm also a bit of a greedy amoral scumbag so I've considered offering it up for a price. She's been an RN for decades and her only kid is grown and out of the house, so I'm sure she's got a fair amount of income she could spend on "entertainment". I've done far worse to pay my rent in the past and I don't think she wants anything beyond a thorough dicking.

It would weird me out to see a grown ass older woman acting like a high school chick who seeks attention in that way....If you dont mind me asking why dont you just put one through her and call it a day? I mean respect if you dont wanna sleep with her but if shes fairly hot, why not just knock one out and move on it

[ra the weak man]

so i met this girl on a dating site. and we've got a lot in common, past delinquency, drugs and traveling. i really wanted it to work. ol girl was my same height and i'm not a little man. i was taken aback and made jokes to my ex that 'i've got a tranny gf' but i didn't think she was.
so we hung out a few x , i'd pick her up an hour away from me and we'd hang out a bit, making out but nothing too sexual. anyways, she'd disappear all the time and she told me she had seizures. i'm thinking 'yeah, seizuring on another nigga's dick'  right?
so 3rd time we hang out after talking for like 3 months [super flowery whenever we talk but it's like missing days in between] and she's got chores so i drop her at the bank and hit the skatepark. then i drop her at her house and she says wait at the beach down the street. i'm waiting an interminably long time and ready to go home. she says 'walk down the street to another beach, secret spot' so i do and she shows up, big ol titties in a tube top and a knapsack. so she wants to pick up beach glass or whatever, i just wanna get my crazy dick wet. or have a fight and go home. i'm exasperated.
and my ex's mom died, i gotta drive her to pack up her mom's shit in the am.
so we make out and w/ a towel over my ass, i'm fingerbanging her on this beach but it's a private beach unless someone is on the sidewalk above us. or looking out the windows of the nearby homes. but it feels private. i got her off and sucked some tit but i barely put the head in and she goes 'we should go to such and such. i've never wanted to fuck someone in a car as bad as i have now. i've never had fingers feel this good before. or i've never said that and meant it.'
i'm like this broad's running fast and loose w/ her talk but yes, i want to fuck her in the truck. i says 'i gotta pee on the beach first' so we take turns cause she also has to pee on the beach.
comes back after taking 10=15 minutes to pee and tells me 'actually i took a shit. but you're cool, i knew you wouldn't mind. i buried it'.
oh boy, i'm about to fuck a girl w/ turd on her ass. suffice to type, analingus will not be thrown down tonight.
so we are driving along the coast and she's all happy to be there hanging out the window 'hello bbbbbb' [name of the town] and glitching out trying to tell me a story. just keeps repeating lines. anyways, we finally park somewhere and she tells me wait behind the vehicle while seh must be drinking booze and monster but i can't see. idk what she's doing at the time.
so we finally start making out standing near the bumper, i told you she was a big woman. and i'm not a tiny man. so the 2 of us are not fitting together easily in coital embrace inside the vehicle. i'm fingering her w/ a amouthful of tit and seh's going 'oh fuck, oh my god, oh fuck, oh my god' over and over. and kind of spinning around. so i'm hanging on. people are driving 100 yards away on the rd [it's dark now] and it's in between embarassing and/or it feels a little rapey. she won't sit still. finally got her against the vehicle and trying to put it in, my crazy boner went down. not completely but i can't be doing everything and it's all one sided. she has to pee so i let her go, fucking find her shaking in the grass.
hail seizure!
so i help her find her home and she starts glitching bad all the way home. like swinging for the fences, whirling her head arouind, just acting a donkey. it seems autonomic but it's still annoying. get her home, she drops all this beach glass on the floor. her mom's like 'waht happened' i said 'seizure' but the mom has experience w/ this and said 'no not a seizure.'
so the cops come and the girl stops moving crazy as the cops enter the room. how bizarre!
they're taking her to the ER for the night, girl is pissed i'm not going w/ her [gotta help my ex move her dead mom's stuff] and the cops say it's a caffeine OD of all things!
dont drink Monster kids.

[Uncle Flea]

Almost everyone I used to fuck for a place to live thinks I'm there ex.

Oh I used to date the ass flea. I'm like oh yeah i remember that (no)

It very uncomfortable that they want to fuck more with out payment. That's definitely not happening

[ra the weak man]

Almost everyone I used to fuck for a place to live thinks I'm there ex.

Oh I used to date the ass flea. I'm like oh yeah i remember that (no)

It very uncomfortable that they want to fuck more with out payment. That's definitely not happening

how much to bone the flea?

[Nosferatu]

Not gonna quote the whole thing but +1 for monster seizure story.

[Mark Renton]

I have plenty cos I use Tinder a lot but they won’t top my mate’s experience.

I can’t remember it properly cos I was perma fried at the time or maybe I tried to erase it from my memory or both but it goes something like this.

He had joined this app where to get more visibility you had to get good ratings / reviews.
He goes into this dodgy council flat to shag this 50 something yo lady and the place is filthy as fuck she’s also missing some teeth.
He’s grossed out and can’t shag her so they settle for a bj. He keeps hearing weird noises, he cums and then she casually opens these curtains behind which there are a few cages with rats, but like big sewer boys.
He freaks out and dips as fast as he can. Gets his 5* review.
The end.

[Idk]

A girl came over to hook up. After a round I was going at it doggy style when a terrible pain started in my right leg. I tried to power through it but then I got the worst cramp in my calf. I was in so much pain I tried to step with my leg to help the cramp but my leg was so tight I couldn’t touch the floor. The whole time the girls just watching me while I’m just wincing uncontrollably. I end up falling on the bad and just moaning til it went away. She then gave me a blow job.

[Yonnycage]

My last ex was absolutely disgusting with hygiene. The first time we boned I had to get outta the car and dry heave cause of the smell but I told her it was cause I ate some bad Mexican food. Fast forward a few months and me having to have talks with her about seeing a gyno and she chalked it up to a “ph imbalance” I’m like no way your pussy smells like a Manhattan dumpster in the middle of July cause you’re too acidic and she finally admitted that when she gets in the shower she doesn’t wash just stands in the water for a while. Sex was weird as shit too she wanted me to pretend like she was 11 years old and I was punishing her for not doing her chores.

[Mean salto]

Real awkward maybe doesn't even count as sexual experience but typical teenager daytime movie date. I think I was about fifteen I think the movie was rat race anyway I'm dressed super spazed like Tom penny in that old es team photo. I have like a 4xl hoody on and size 42 king gee workpants that are super thick material with Scotch guard so theyre crazy rigid like can stand up by themselves. I also probably only needed a size 32 at the time. Anyway we sit down and I immediately notice I have the most gigantic pants tent. Like that curb episode but 10x bigger. I don't want to draw attention to it to fix it and it's dark so I'm just like whatever. Anyway as things go we're making out the whole movie and she keeps like touching my chest then stomach then stopping over and over like every minute. Then one time I look when she does it and she isn't stopping but jerking off the big stiff amount of pants material I have bulging on my lap. In my head now I'm complete panic mode. Wtf am I supposed to do? Whip out my penis? Redirect her to where my penis actually is? Then with what she's been grabbing she's going to be expecting a full Pringles can which I don't have.
Fortunately the movie ended and our session was over. Soz the story goes nowhere it's just part a of a derpy start to sex life

[PuffinMuffin]

Real awkward maybe doesn't even count as sexual experience but typical teenager daytime movie date. I think I was about fifteen I think the movie was rat race anyway I'm dressed super spazed like Tom penny in that old es team photo. I have like a 4xl hoody on and size 42 king gee workpants that are super thick material with Scotch guard so theyre crazy rigid like can stand up by themselves. I also probably only needed a size 32 at the time. Anyway we sit down and I immediately notice I have the most gigantic pants tent. Like that curb episode but 10x bigger. I don't want to draw attention to it to fix it and it's dark so I'm just like whatever. Anyway as things go we're making out the whole movie and she keeps like touching my chest then stomach then stopping over and over like every minute. Then one time I look when she does it and she isn't stopping but jerking off the big stiff amount of pants material I have bulging on my lap. In my head now I'm complete panic mode. Wtf am I supposed to do? Whip out my penis? Redirect her to where my penis actually is? Then with what she's been grabbing she's going to be expecting a full Pringles can which I don't have.
Fortunately the movie ended and our session was over. Soz the story goes nowhere it's just part a of a derpy start to sex life

Hahaha, this is hilarious. Makes ya wonder how Polar Big Boys got their name.

[h00man]

Real awkward maybe doesn't even count as sexual experience but typical teenager daytime movie date. I think I was about fifteen I think the movie was rat race anyway I'm dressed super spazed like Tom penny in that old es team photo. I have like a 4xl hoody on and size 42 king gee workpants that are super thick material with Scotch guard so theyre crazy rigid like can stand up by themselves. I also probably only needed a size 32 at the time. Anyway we sit down and I immediately notice I have the most gigantic pants tent. Like that curb episode but 10x bigger. I don't want to draw attention to it to fix it and it's dark so I'm just like whatever. Anyway as things go we're making out the whole movie and she keeps like touching my chest then stomach then stopping over and over like every minute. Then one time I look when she does it and she isn't stopping but jerking off the big stiff amount of pants material I have bulging on my lap. In my head now I'm complete panic mode. Wtf am I supposed to do? Whip out my penis? Redirect her to where my penis actually is? Then with what she's been grabbing she's going to be expecting a full Pringles can which I don't have.
Fortunately the movie ended and our session was over. Soz the story goes nowhere it's just part a of a derpy start to sex life

lol hell yeah Rat Race!

[IUTSM]

I used to get pretty wasted at least a few nights per week when I was in my 20s and would end up at the dive bar at the end of my street. I was generally one of, if not the youngest person in there by at least 15 years, usually a bit more. I was a young dude with tattoos and older broads would often enjoy the flirt or whatever. Definitely had a few awkward experiences over there.

One night I'm chatting it up with this lady Kim. I'd seen Kim around a bunch and know that she's this older biker chick. She's on one this night telling me her old man, this dude named Bobby, was outta the picture because he was smoking crack again. I'm like "ok" and just looking at her very exposed chest. So she's buying me shots of wild turkey 101 and we're just having some laughs til last call. Well, we get booted from the bar and I'm like "adios. I'm walking home." and she says "oh, honey, come smoke a joint with me at my car." We start smoking some funky old person weed (weed was often pretty rugged at this point) and low and behold we start making out against the car. It was a Chrysler 300, white. She's pressing those big old biker boobies against me and I'm sprung. She says she's gonna give me a ride home, so we hop in the car and start making out some more in the front seat and I'm thinking "fuck it dude. just go for it" and I'm going for the button in her pants, hands going in, mind you it's like less than 30 seconds in the car, and then

WHEEEEEEEEEEWHEEEEEWHEEEEE
and I jump up all WHAT THE FUCK!!?!?!?! and she's laughing and says "that's my pet pig. forgot it was back there." that lil piggie probably saved me from some lifetime friends, right there.

[DaleSr]

I used to get pretty wasted at least a few nights per week when I was in my 20s and would end up at the dive bar at the end of my street. I was generally one of, if not the youngest person in there by at least 15 years, usually a bit more. I was a young dude with tattoos and older broads would often enjoy the flirt or whatever. Definitely had a few awkward experiences over there.

One night I'm chatting it up with this lady Kim. I'd seen Kim around a bunch and know that she's this older biker chick. She's on one this night telling me her old man, this dude named Bobby, was outta the picture because he was smoking crack again. I'm like "ok" and just looking at her very exposed chest. So she's buying me shots of wild turkey 101 and we're just having some laughs til last call. Well, we get booted from the bar and I'm like "adios. I'm walking home." and she says "oh, honey, come smoke a joint with me at my car." We start smoking some funky old person weed (weed was often pretty rugged at this point) and low and behold we start making out against the car. It was a Chrysler 300, white. She's pressing those big old biker boobies against me and I'm sprung. She says she's gonna give me a ride home, so we hop in the car and start making out some more in the front seat and I'm thinking "fuck it dude. just go for it" and I'm going for the button in her pants, hands going in, mind you it's like less than 30 seconds in the car, and then

WHEEEEEEEEEEWHEEEEEWHEEEEE
and I jump up all WHAT THE FUCK!!?!?!?! and she's laughing and says "that's my pet pig. forgot it was back there." that lil piggie probably saved me from some lifetime friends, right there.

SSOOOOOOOOOME PIG

[Nosferatu]

I used to get pretty wasted at least a few nights per week when I was in my 20s and would end up at the dive bar at the end of my street. I was generally one of, if not the youngest person in there by at least 15 years, usually a bit more. I was a young dude with tattoos and older broads would often enjoy the flirt or whatever. Definitely had a few awkward experiences over there.

One night I'm chatting it up with this lady Kim. I'd seen Kim around a bunch and know that she's this older biker chick. She's on one this night telling me her old man, this dude named Bobby, was outta the picture because he was smoking crack again. I'm like "ok" and just looking at her very exposed chest. So she's buying me shots of wild turkey 101 and we're just having some laughs til last call. Well, we get booted from the bar and I'm like "adios. I'm walking home." and she says "oh, honey, come smoke a joint with me at my car." We start smoking some funky old person weed (weed was often pretty rugged at this point) and low and behold we start making out against the car. It was a Chrysler 300, white. She's pressing those big old biker boobies against me and I'm sprung. She says she's gonna give me a ride home, so we hop in the car and start making out some more in the front seat and I'm thinking "fuck it dude. just go for it" and I'm going for the button in her pants, hands going in, mind you it's like less than 30 seconds in the car, and then

WHEEEEEEEEEEWHEEEEEWHEEEEE
and I jump up all WHAT THE FUCK!!?!?!?! and she's laughing and says "that's my pet pig. forgot it was back there." that lil piggie probably saved me from some lifetime friends, right there.

Then what happened?

[PAWL]

That’ll do pig that’ll do

[Mark Renton]

@IusedToSkateMore great story man so hilarious haha.

Damn that car must have stank like crazy. Leaving a pig in your trunk while you get drunk at a dive bar is some nutter shit.

Kinda curious how the pig was, was it like in the movie "Babe". I can't believe he didn't unload a lot of shit in the trunk or something. Poor little thing.

[IUTSM]

@IusedToSkateMore great story man so hilarious haha.

Damn that car must have stank like crazy. Leaving a pig in your trunk while you get drunk at a dive bar is some nutter shit.

Kinda curious how the pig was, was it like in the movie "Babe". I can't believe he didn't unload a lot of shit in the trunk or something. Poor little thing.

I don't really remember how gnarly the car smelled, it was actually a kind of nice car for what it was. I've known numerous people who have small pigs for pets. they're fairly hygienic I guess. Regardless, it was just a weird, weird moment, man. I've got crazy stories from that bar.