Awkard sexual encounters(an butt stuff) (1 Viewer)

Barf

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The year was 2006. I was just about to graduate from high school.

I was full of testosterone, malt liquor and dog barbiturates.

And I decided I loved all things opiate.

I could do no wrong, life was my bitch.

In walks John motha fuckn Davis,

You guys remember Waffle House?

Talk about Kennedy theories for day

I need a nap myself,

So this story will have to be continued at another time.
 
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Older Than Dirt

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Well, that was informative.

"Awkward sexual encounters"? Is there some other way humans have sex with each other, until they get used to each other?

Wait, did you kids invent some new kind of way?

Didn't think so; the only thing really even older than dirt is fucking and sucking.
 

Eng JR Lupo RV323

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Awkward butt stuff. Had a conductor girlfriend when I was an engineer. She had a huge collection of toys and we continued adding to her collection. We bought a translucent purplish pink butt plug. Standard shape, cone about idk 1½ at the larger end. Below that it got smaller and then flared out on the bottom as a stopper. It was for her but... I'm an adventurous guy. So one day she puts it in my ass and starts giving me oral. Pretty great all in all, until I felt like it was continuing to move further into my butt.
I guess my ass spokes relaxed or something and it was made of a firm gel type rubber so there was a little flex. The stopper felt like it was becoming more like a cone than a flat stopper, it kept going in deeper and I freaked out and started yelling get it out get it out! She was laughing so hard she could barely even work on removing it she just kept laughing and I was already picturing myself in ER explaining the situation to numerous medical staff. Fortunately she was able to remove it and everything was fine but I always think of that anytime I get the wild Idea that I might want something up my butthole.
 

Juan Derlust

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So I'm in the ER having the anal beads removed from my ass; putting one foot on the table, the doctor braced himself, grabbed the end with both hands, pulled with all his might... And I came like a motherfucker!!!



*Actually an old comic routine I heard once - not my own experience

- but it might've been!
 

Eng JR Lupo RV323

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Back in the day yahoo chat rooms were pretty active. I couldn't begin to guess what chat room I was in but I believe it had some sort of local connotation to it. Perhaps something as simple as "Fresno peeps" or some bullshit like that. There was a girl who went by the name Bad Kittytude. Her and I were having decent conversation and took it to the DMs. Exchanged phone numbers, I called her and we start chatting.

Just the usual boring shit, what do you do for work? Have you lived here your whole life, whatever the fuck I don't remember. She tells me she's a phone sex actress for work. I'd never met a phone sex actress, I didn't even know that's what they're called. I had so many questions. At some point she says "you should come over" and I'm like yeah on my way!

I arrive, knock on the door and she answers. I'm immediately engulfed by the delightful scent of cat piss. It's one of those houses, where you can be certain the person hasn't changed the litter box in several months or more. It's hard to breath in this motherfucker. But I'm a horny young man so I'm doing my best to breathe normally/resist gagging.

She's 6'2", just an absolute beast of a woman height wise. Not skinny, not fat. She's just a large woman, I guess you could say big boned. We start making out on her couch and she says "I'm working right now, like on the clock or whatever. So it's possible I'll have to answer a phone sex call. Is that something you think you could handle? Is it going to bother you or anything?"

I'm like fuck no that sounds kind of hot I'm curious to see how that plays out from this perspective. She says "Ok, but sometimes they get a little weird. I have to role play certain scenarios depending on what they want me to talk about. You sure it won't be too weird for you?" I'm like nope, I can't see how that would bother me at all it sounds hella interesting! She says "Alright, do you wanna go to my bedroom?"

I'm both excited and relieved. Hoping the stench subsides a bit, nope. Apparently the litter boxes are kept in her fucking bedroom! I'm dying, this house could gag a maggot. We start messing around on her bed, the phone rings and she sighs. "Hold on, I'll try to make this quick" she answers the phone.

I'm laying there beside her still sort of messing around, sucking on her tits and whatnot. She's got a daddy daughter roleplay. She's softening her voice, she's calling him daddy. Saying all this weird shit like "You'e not going to hurt me again are you daddy?" and whatnot. I slowly begin to inch away from her. Now I'm just laying there on my back waiting for this creepy shit to end. It takes about 7 minutes and she hangs up. We start messing around again, it's getting pretty raunchy and the phone rings again.

It's a fairly normal call this time, she's just talking nasty and I pretend she's talking to me as i continue to explore her body. The call ends and we get those panties off, we start banging and then she stops me and says "I have a thing.. something I like done to me. Are you open to different stuff?" I'm like yeah what's up hit me with it? She says "alright, here let me see your hand. I give her my hand, she clasps her hands around it and forms my hand in such a way that all my fingertips are touching each other, thumb is joined with them.

She says "Yes, like this. Basically make your hand like a duck" I'm like ok, I can do that. Then she guides my hand down to her pussy. She instructs me to start inserting my fingertips. She instructs me to slowly twist them inside her back and forth. "Mmmhmmm now use a little more pressure." I start to push them into her, my fingers are all about halfway inside. It's getting tight.

She begins to straighten out her entire body, arches her back and stiffens her legs while keeping them spread. She says "push harder" I push harder, my fingers are completely inside her now, my knuckles are held out. It's just way too fucking tight to push my knuckles through, she reaches down and starts applying additional pressure to my wrist, she's trying to get my knuckles past. I realize this bitch really wants me to try and get my entire fist into her vagina.

I kinda just figure at this point fuck it, give her what she wants. So I start pushing in real hard, my knuckles breach through and my entire fist pops inside. I can feel her cervix, it's actually rather fascinating to me. I've never felt things this deep in a vagina before. I've had a finger or two in but never an entire hand to explore with.

I'm just sort of lost in this fascinating moment where I'm checking the scene out with my fingers, seeing what else I can feel. She starts thrusting her body down onto my fist and exclaims almost violently "NOW FUCK ME!" I have a moment of confusion.. wait did we just do all this and now she wants me to pull my fist out and fuck her? No, she wants me to fuck her with my fist holy shit. So I'm just like whatever I'm already here wrist deep in this woman here goes!

So I just start punching the shit out of her insides. She keeps thrusting down onto my fist like she wants it harder. She yells "HARDER!" and I just start laying into this ladies guts. I'm punching as hard as I can punch while laying on my side. She starts having orgasms, it's pretty fucking incredible but also.. different. Then she sits up fist still inside her and bites the fuck outta my chest. Like borderline drew blood too fucking much man! I like some teeth action but she went way too hard. I slowly pull my fist from inside her once I think she's wore out and I just kind of slowly sit up, put my feet off the side of the bed, stand up.

Find my shirt, pants, shoes.. put everything on. Awkwardly lean over the bed, cover her with a blanket trying to make this moment any less awkward and then I just let myself out. I didn't have any desire to chase my fist down that hotdog hallway. There's no way my dick can follow an act like my fist just put on. She's all blasted out, opened up like she's just given birth. I just went home and kind of tried to forget it. She hit me up the next day "You wanna come over again?"

I can't remember what excuse I gave her but I never went back for more. My hands are fucking huge. I'm 6'2" 3hundo with a large man type build. My fists are about the same girth as the widest part of a 40 ounce of Old English 800. Aww man, those vanilla days. I wouldn't think twice if someone asked me to fist em nowadays.
 

Older Than Dirt

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There is that old story i've heard as a "true story" from about every EMT, and emergency room nurse, that i've ever known.

It goes something like this (maybe you've heard it too?; i will not tell it well):

Dude comes into ER wicked embarrassed.

After much hemming and hawing, he admits he might have got a Barbie doll caught up his ass during some sex play, and, of course, is finding it difficult to remove (due to the arms and legs being, um, flexible).

Everyone is having a good laugh at the poor guy's plight, when the Indian ER doc who has gone in the back to help him comes out , and says (in heavily accented English):

"You lot ought to be very ashamed of yourselves. You call yourselves medical professionals, and yet you are all too busy laughing at this poor patient with Barbie doll lodged in his rectum [holds her up in gloved hand] to help him, and none of you even care about his suffering ...

[moving his other hand from behind his white coat...]

"from Ken!"

[anyone reading this who has not done a google image search on "rectal foreign bodies" might find amusement in doing so; there are contests and what-not among ER staff]
 

Eng JR Lupo RV323

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First time with a new partner, we were having sex in a very spontaneous random moment where we're just hanging out with my dog on the bed and then partner is like hey can I fuck you? And I'm all sure!. So we get nakes, I'm on my back partner is riding me and we're maybe only 3 minutes into it and I notice my dog is literally right between my legs behind my partners back. Kaya has her muzzle right in the vicinity of my partners crack and it legit looked like she was gettin in there with that rim job action.

Startled I brought my heels up to Kaya's sides and pulled her back outta the crack and at the same time pulled my partners body close to me and said "Oh my god I'm so sorry, I think my dog just gave you a rim job" and in a very unfazed nonchalant tone partner simply says "sometimes that's just part of it" and keeps riding me. I nearly died, like what? In my mind I'm thinking "What do you mean sometimes that's just part of it my dog just made this a three-way.. also reminder.. she's a dog! And I think she just licked your butthole! That's never part of it!"

I was so stunned by the way partner said it I hadn't even gotten those words out yet but partner could see it on my face and knew what I said must have been misunderstood. So partner goes *wait, what did you just say?" And I repeat, I'm so sorry I think my dog just gave you a rim job. We both start laughing and partner's like ”no no, definitely not I would have felt that for sure. I thought you were saying something like about your dick slipping out" and we continued to laugh and have sex, it was certainly one of my most awkward sexual encounter I can recall. Turns out Kaya was just sniffin around, definitely the only time she's smelled/observed sex.
 

iamwhatiam

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Speaking of ER visits. I know an ER doctor and he gets a fair amount of people from time to time with stuff stuck up their butt. He was telling us of this couple that came in one time complaining of some pain in the area there. Can't remember if it was the dude or girl. So he takes an X-ray and can obviously see there's a vibrator stuck up there. So he goes in there and eventually gets it out, and then plops the thing right nonchalantly on the gurney table after he's done.

The couple got all flustered and embarassed, "OH MY GOD. DON'T JUST LEAVE THAT THING SITTING OUT THERE LIKE THAT. GET RID OF IT. GET RID OF IT". He almost told them 'Well, what's the big deal. It was just up your butt' but he kept quiet. lol
 

iamwhatiam

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Back when I used to turn tricks, I remember there was there was this older fella who was a foreigner I met on the main strip somewhere down in Key West. He sounded like he was from some eastern European country. Anyways, we get up to his rental flat....and start to undress and I start to making my way to his bed or the nearest couch when he stops me and tells me in his thick accent to, "Walk around and act like I've never been here before" or something like that.

I'm thinking to myself, "um....okay....shouldn't be too fucking hard as it's the first time I've ever stepped foot inside here dude, but whatever". So I'm walking around looking at stuff in wonder, checking out the pool table, admiring a painting on the wall, etc. Then I walk back over to him and start to go in to make out or whatever and he stops me again, "No. No. Walk around like first time here." So, I'm like "fuck dude...this is a weird ass kink, how long am I supposed to go about like this, but whatever....i won't judge" So I get up and continue walking around with this questioning look on my face, expressing interest in this or that, asking a question about this wall hanging, etc.

This goes on like once or twice more, before he finally tells me, "This too weird. Not working"...(Yeah, you're telling ME dude) .and proceeds to tell me to leave and hands me some money from his wallet. LMFAO. I leave his apartment and I'm just like WTF JUST HAPPENED?!?!?

Obivously, there was some kind of language barrier and he thought he was telling me to do one thing and I was misunderstanding him, but I can't for the life of me to this day figure out what the actual fuck he was wanting me to do. I'm sure, to this day, there is some old fuck back in Ukraine or Romania somewhere who is recollecting this same story, but a slightly didn't version of it.
 

Eng JR Lupo RV323

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I wonder if he wanted you to walk into the room again, as if you had never been in there. Like a porn scene, how a lot of those older ones would just be some random dude opening a door and walking in on someone as the funk music fades in. He probably just wanted to reset the scene? Idk. I sure love the idea of him pondering quite frequently what in the actual fuck you were doing. Like it just comes to his mind at least once a week, anytime he sees someone walking about curiously.
 

iamwhatiam

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Just remembered the time this girl brought me back to her home. I was sleeping on the streets then so I was all about a hot shower, meal, and kickin back inside watching some movies or whatever. We get to her place, and before long it's apparent that she wants to jump on my love stick. I tell her that unfortunately I'm gay and I don't think I'd enjoy it all that much....certainly not going down on you or fingering that weird alien cave of yours. *shivers*

I just remember her getting real upset....like not mad upset....but legit crying. And telling me how into guys who were guitar players she was, and how she liked me so much, she wouldn't be able to have my baby one day. EXCUSE ME?????? We just met like literally an hour ago. Hold up. Full STOP. Then she starts showing me pictures of this other guitar play guy who she had fucked once or twice and was all obssessed over but how the guy wouldn't return any more of her phone calls. (I wonder why???)

So, overly obsessed cringey guitar player loving weird girl.....if you, god forbid, happen to be on this website or ever read this. Take a hint, not a good way to attract a mate. People in general don't like to start talking about having a baby when they first meet you. Dial that shit waaaaaaaaay back.

Hmmmmmm.......shit, now I'm hoping I MYSELF don't end up on the awkward sexual encounters stories lmao
 

Juan Derlust

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Comedy is basically a willingness to dive in the deep end & the ability to spin ensuing misfortune into gold - 99 out of 100 folks on here qualify by that measure. Unfortunately, I take myself way too seriously...
 

Origen

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The story of the apartment drenched in cat odor reminded me of a similar experience. I met this guy online who was very much my type. When I got to his place he actually looked even better in person, but the apartment smelled horrible from his 5 cats. He got undressed and laid on his back, and spread his legs to take it up the ass. He had fetishized black men, so i was ever much his type,but I was so overwhelmed by the stench all but gagging and couldn’t get it up! I made some lame excuse and left. My clothes still stank from the cat piss later that night. How anybody goes nose blind to odor that strong is beyond me
 

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