Author Topic: Awkward Sexual Experiences  (Read 462926 times)

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SpankerChief

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Re: Awkward Sexual Experiences
« Reply #2070 on: March 28, 2019, 04:36:05 AM »
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my elderly mum whom I am estranged to just detailed a daunting and cringeworthy tale of doing coke bumps off my dad's dick.  I was trying to be as nice as possible but she is hard of hearing so I spent most of the time making fun as I didn't want to hear a single sentence. sooooooo awkward.
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I remember this episode and how weird is that? It is like dejvu am I right? sniiiiiiiifffffffffffffffffffff
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WobbleHeadBob

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Re: Awkward Sexual Experiences
« Reply #2071 on: March 28, 2019, 04:38:19 AM »
Mascot costumes are real expensive, are furry ones cheaper??

sex toys are mad expensive, if anything i reckon furry costumes would be even pricier

i went to a fetish themed club night once and there was a dude walking around in a head to toe latex batsuit, complete with dildo bat ears and a plastic batdong that was fucking yuge.

Owen

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Re: Awkward Sexual Experiences
« Reply #2072 on: March 28, 2019, 05:37:59 AM »
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my elderly mum whom I am estranged to just detailed a daunting and cringeworthy tale of doing coke bumps off my dad's dick.  I was trying to be as nice as possible but she is hard of hearing so I spent most of the time making fun as I didn't want to hear a single sentence. sooooooo awkward.
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I remember this episode and how weird is that? It is like dejvu am I right? sniiiiiiiifffffffffffffffffffff

Seems like you were born to relive boner sniffing
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Re: Awkward Sexual Experiences
« Reply #2073 on: April 18, 2019, 08:20:24 PM »
This isn't my story but read this in a facebook group the other day and it reminded me of this thread so thought it was worth the bump:



Throwaway account because my wife follows my regular account here. My (28m) wife (26f) and I have admittedly had very vanilla sex throughout our 3 year marriage. We had our first kid a year ago and it seriously slowed down our sex life. However, a little under a month ago she approached me about “trying new things”. She has been hanging out with a group of moms in our neighborhood and one of them told her that she and her husband tried pegging and it completely transformed their marriage. My wife told me that she wanted to try pegging as well to “spice things up”. At first I thought it was a joke, but soon realized she actually wanted to peg me. I had never done assplay before and had always lived by the philosophy that the anus is solely an exit, but my wife made it clear that this was important to her so after a few days I obliged.

That next weekend, she pegged me and everything was surprisingly enjoyable. Additionally, the week following the pegging was one of the best weeks we’ve had together since the birth of our child. We were back to our old sex life, doing things like having sex before work and even waking each other up with head. However, that next weekend she told me she wanted to peg me again. I was slightly confused as to why this last week of sex wasn’t cutting it for her, but I agreed.

This is when things took an extreme turn. During this second pegging while my wife was inside of me, she grabbed my hair, craned my neck to the right, and pressed our foreheads together. I had never seen her take control like this and thought it was very hot until she looked me in the eye and whispered “I want your shit”. I pulled my face away and asked her to repeat and she said “I want you to shit on me”. I pushed her off of me and asked her if she was joking and she started crying. I felt like a fucking dick because she thought I was kinkshaming her. In a way, I was because I thought the request was far too extreme. I ended up leaving for the night and stayed with one of my close friends, but didn’t tell him what happened.

After that incident, my wife and I hardly talked all week unless it related to our son. At the end of the week, I asked my wife to talk about what happened. She told me again that she wanted me to shit on her and that it meant a lot to her. I thought it was sickening, but she claimed this was her deepest, darkest kink. I couldn’t understand how and why my shit excited her, but she insisted that she has always wanted this.

We fought about this for about a week and after watching some scat porn and reading articles by people who also shared this kink, I tried to put myself in my wife’s shoes. I told her that I will shit on her if that is what will turn her on. She was so happy and even though I was still completely nauseated by this desire, I wanted to satisfy her.

That brings us to tonight. We were having sex for the first time this week when I (regrettably) confessed to her that I had to take a shit. She perked up with a smile, sensed my discomfort, and began stroking my hair and whispering encouraging things to me. I still really didn’t want to go through with it, but since I had promised her I pulled out and we ran to the bathroom.

She got into the bathtub and I hung my ass over the side of the tub. I started pushing, but unsurprisingly found it very difficult to successfully shit on my wife. I turned my head around to see my wife staring up and smiling at me waiting for me to finish. With enough time, I was finally able to get a turd to start coming out. I could hear my wife breathing heavier beneath me as my asshole started opening. However, before the turd was able to drop on her chest, I felt a sensation around my asshole.

I turned around and saw my wife - the love of my life, the mother of my son - attempting to catch my turd in her mouth as it fell out of my asshole. I was horrified that she would try to do this, and tried to pull the shit back into my body so she couldn’t receive it in her mouth. Seeing what looked like an attempt by her to eat my shit brought me close to throwing up.

As I clenched my buttcheeks together to try to stop the shit from reaching my wife, the clenching cut off a very small piece of my shit and I heard it land somewhere beneath me. I was too scared and disgusted to look at my wife to see what she had done with it, so I ran to the other bathroom to clean myself. As I was sitting in the other bathroom thinking about how I will ever be able to look my wife in the eye again, I heard footsteps approaching. My wife lightly knocked on the door. I didn’t respond and was on the verge of throwing up the more I thought about what just happened. She walked away and then I got a text from her thanking me for fulfilling her wish and asking me to come to bed.

I’ve been sitting in the living room typing this for the last half hour scared to face my wife. We have plans to take our son to the zoo with another family tomorrow, but I don’t think I can look at her

jakeumms

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Re: Awkward Sexual Experiences
« Reply #2074 on: April 18, 2019, 08:43:58 PM »
Man, I remember when Dan Savage named that act Pegging. I'm just tripping on how language works but it's weird to remember a time when fucking ya boy up the butt with a strap-on was an act that had no name. I personally was always partial to B.O.B. (bend over boyfriend.)

^Also, there's no way that's real. Degradation is fully a kink but poop is like senior level activity. There would have to been at least an inclination that wifey like to be fucked up. I'm not calling BS on the fact that you saw it posted WH, just that it actually happened to the OP.
« Last Edit: April 18, 2019, 08:54:02 PM by jakeumms »
them cats are out getting mashed up to jungle, he's out mashing up jungle cats. it's just not gonna work.

Francis Xavier

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Re: Awkward Sexual Experiences
« Reply #2075 on: April 19, 2019, 08:12:24 AM »
Maybe she woke up and decided after a lifelong journey of missionary sex,she wanted to eat her husbands shit after fucking his ass with a strap on. You never know when your destiny is revealed.

Damn I left my bubbler at my parents house

PincherBug

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Re: Awkward Sexual Experiences
« Reply #2076 on: April 19, 2019, 08:20:00 AM »
Yummy

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Re: Awkward Sexual Experiences
« Reply #2077 on: April 19, 2019, 08:27:49 AM »

WastedHippy

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Re: Awkward Sexual Experiences
« Reply #2078 on: April 19, 2019, 03:14:27 PM »
Man, I remember when Dan Savage named that act Pegging. I'm just tripping on how language works but it's weird to remember a time when fucking ya boy up the butt with a strap-on was an act that had no name. I personally was always partial to B.O.B. (bend over boyfriend.)

^Also, there's no way that's real. Degradation is fully a kink but poop is like senior level activity. There would have to been at least an inclination that wifey like to be fucked up. I'm not calling BS on the fact that you saw it posted WH, just that it actually happened to the OP.

haha man I thought the same thing because it's a pretty extreme jump from "vanilla sex" but I guess she could have just repressed those weird urges. Plus the guys account was a legit throwaway one, he's deleted the post since and the way he posted it in the group and his replies were deadly serious. Not saying that makes it real but judging off some of the experiences in this thread I'd say stranger things have happened.

Joclo

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Re: Awkward Sexual Experiences
« Reply #2079 on: April 20, 2019, 10:09:14 AM »
Came home shitfaced and walked in on my roommate buttfucking a real doll reverse cowgirl. Not sure if that counts but it was awkward. Everything looked real until I spotted the metal ankles.

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Re: Awkward Sexual Experiences
« Reply #2080 on: April 20, 2019, 06:42:43 PM »
Came home shitfaced and walked in on my roommate buttfucking a real doll reverse cowgirl. Not sure if that counts but it was awkward. Everything looked real until I spotted the metal ankles.
You ask him how much it cost? I'm willing to buy used if the price is right.
Before you say the music sucked, have you considered shutting the fuck up?

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Re: Awkward Sexual Experiences
« Reply #2081 on: April 20, 2019, 06:56:56 PM »
Came home shitfaced and walked in on my roommate buttfucking a real doll reverse cowgirl. Not sure if that counts but it was awkward. Everything looked real until I spotted the metal ankles.

This was years ago, so before the tech really allowed for things like Real Dolls, but I had a similar situation. On my way out of the apartment, the doorbell rings so I run downstairs to grab it on the way out. It's a FedEx driver with a package for my roommate. I run it up to him and leave the house but get about a block before I realize I forgot my wallet. I run back upstairs just in time to see the roomie admiring his new gear. It's the cheapest blow up doll in the kind of packaging that a child's Halloween costume used to come in. Thin cardboard box with a cellophane top so you can see the face of the thing you're trying to fuck. She had red hair. I pretended I didn't see but oh I saw.
them cats are out getting mashed up to jungle, he's out mashing up jungle cats. it's just not gonna work.

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Re: Awkward Sexual Experiences
« Reply #2082 on: April 20, 2019, 07:03:50 PM »
One of the worst parts of the bad sex I keep having is when I realize, "fuck, I was really hoping to crash here tonight but now I gotta get a taxi home."
« Last Edit: April 20, 2019, 07:06:46 PM by Grind King Rims »

Joclo

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Re: Awkward Sexual Experiences
« Reply #2083 on: April 21, 2019, 03:11:23 PM »
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Came home shitfaced and walked in on my roommate buttfucking a real doll reverse cowgirl. Not sure if that counts but it was awkward. Everything looked real until I spotted the metal ankles.
[close]
You ask him how much it cost? I'm willing to buy used if the price is right.

That was another thing I've wondered about. It had to be used/passed down because this dude was broke as fuck all the time. Guy was pretty weird and I think he had a sex addicktion because he used to pull quite a few chics so why fuck the cankles off a used doll? #Grimy

cosmicgypsies

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Re: Awkward Sexual Experiences
« Reply #2084 on: April 23, 2019, 02:57:56 AM »
from around November time up until February I was kinda seeing this girl on and off, was a bit of a weird situation given she'd just broke up with her ex and shit but w/e I don't know that fool. In January or so we went out on a lil wilderness explore being that were both into that (for backstory we'd already kissed and shit by this point and were aware we both had feelings) and yeah shit was alright just walking around exploring talking shit happy as larry. We somehow end up on some mtb trails and from there we find this weird abandoned cave/alcove thing with a tiny hole in a wall to enter and she's all "go inside" so I'm like alright fuck it. inside this mfer is pitch black, couldn't see a few ft infront of me. So we're dicking around in there and we start kissing, starts getting a bit rougher shes scratching the fuck outta my back while im biting her neck and all that shit, starts stroking my dick through my trousers and im harder than fucking stonehenge swear on god i was boutta nut just from that. one thing lead to another and she's basically stood there with her tits out so im sucking/biting em with her hand down my pants shit is lit. eventually she just whispers "get it out" so i whip the fuckin thing out and she starts stroking me. now bare in mind this is January in england it was about -1c and her hands were cold as shit and as soon as she touched my dick shit just fuckin flopped. imagine sticking your dick in a fucking ice cooler shit was so cold. we just laughed it off and she's all "thats a shame i was gonna suck it" like bruhhhhhhhhhhhhhh come on. prolly for the best really as i dont think she was actually broke up with her ex at the time but yeah fuck cold weather.

here's a picture from where i was stood inside said cave thing for reference


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Re: Awkward Sexual Experiences
« Reply #2085 on: April 23, 2019, 06:48:32 AM »
from around November time up until February I was kinda seeing this girl on and off, was a bit of a weird situation given she'd just broke up with her ex and shit but w/e I don't know that fool. In January or so we went out on a lil wilderness explore being that were both into that (for backstory we'd already kissed and shit by this point and were aware we both had feelings) and yeah shit was alright just walking around exploring talking shit happy as larry. We somehow end up on some mtb trails and from there we find this weird abandoned cave/alcove thing with a tiny hole in a wall to enter and she's all "go inside" so I'm like alright fuck it. inside this mfer is pitch black, couldn't see a few ft infront of me. So we're dicking around in there and we start kissing, starts getting a bit rougher shes scratching the fuck outta my back while im biting her neck and all that shit, starts stroking my dick through my trousers and im harder than fucking stonehenge swear on god i was boutta nut just from that. one thing lead to another and she's basically stood there with her tits out so im sucking/biting em with her hand down my pants shit is lit. eventually she just whispers "get it out" so i whip the fuckin thing out and she starts stroking me. now bare in mind this is January in england it was about -1c and her hands were cold as shit and as soon as she touched my dick shit just fuckin flopped. imagine sticking your dick in a fucking ice cooler shit was so cold. we just laughed it off and she's all "thats a shame i was gonna suck it" like bruhhhhhhhhhhhhhh come on. prolly for the best really as i dont think she was actually broke up with her ex at the time but yeah fuck cold weather.

here's a picture from where i was stood inside said cave thing for reference



Thank you for the picture, it really helps provide context.
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Re: Awkward Sexual Experiences
« Reply #2086 on: April 23, 2019, 08:30:45 AM »
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from around November time up until February I was kinda seeing this girl on and off, was a bit of a weird situation given she'd just broke up with her ex and shit but w/e I don't know that fool. In January or so we went out on a lil wilderness explore being that were both into that (for backstory we'd already kissed and shit by this point and were aware we both had feelings) and yeah shit was alright just walking around exploring talking shit happy as larry. We somehow end up on some mtb trails and from there we find this weird abandoned cave/alcove thing with a tiny hole in a wall to enter and she's all "go inside" so I'm like alright fuck it. inside this mfer is pitch black, couldn't see a few ft infront of me. So we're dicking around in there and we start kissing, starts getting a bit rougher shes scratching the fuck outta my back while im biting her neck and all that shit, starts stroking my dick through my trousers and im harder than fucking stonehenge swear on god i was boutta nut just from that. one thing lead to another and she's basically stood there with her tits out so im sucking/biting em with her hand down my pants shit is lit. eventually she just whispers "get it out" so i whip the fuckin thing out and she starts stroking me. now bare in mind this is January in england it was about -1c and her hands were cold as shit and as soon as she touched my dick shit just fuckin flopped. imagine sticking your dick in a fucking ice cooler shit was so cold. we just laughed it off and she's all "thats a shame i was gonna suck it" like bruhhhhhhhhhhhhhh come on. prolly for the best really as i dont think she was actually broke up with her ex at the time but yeah fuck cold weather.

here's a picture from where i was stood inside said cave thing for reference


[close]

Thank you for the picture, it really helps provide context.
hahaha

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

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Re: Awkward Sexual Experiences
« Reply #2087 on: April 23, 2019, 03:04:28 PM »
People always coming up with excuses to repost that black hole pic

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Re: Awkward Sexual Experiences
« Reply #2088 on: April 23, 2019, 03:25:35 PM »
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from around November time up until February I was kinda seeing this girl on and off, was a bit of a weird situation given she'd just broke up with her ex and shit but w/e I don't know that fool. In January or so we went out on a lil wilderness explore being that were both into that (for backstory we'd already kissed and shit by this point and were aware we both had feelings) and yeah shit was alright just walking around exploring talking shit happy as larry. We somehow end up on some mtb trails and from there we find this weird abandoned cave/alcove thing with a tiny hole in a wall to enter and she's all "go inside" so I'm like alright fuck it. inside this mfer is pitch black, couldn't see a few ft infront of me. So we're dicking around in there and we start kissing, starts getting a bit rougher shes scratching the fuck outta my back while im biting her neck and all that shit, starts stroking my dick through my trousers and im harder than fucking stonehenge swear on god i was boutta nut just from that. one thing lead to another and she's basically stood there with her tits out so im sucking/biting em with her hand down my pants shit is lit. eventually she just whispers "get it out" so i whip the fuckin thing out and she starts stroking me. now bare in mind this is January in england it was about -1c and her hands were cold as shit and as soon as she touched my dick shit just fuckin flopped. imagine sticking your dick in a fucking ice cooler shit was so cold. we just laughed it off and she's all "thats a shame i was gonna suck it" like bruhhhhhhhhhhhhhh come on. prolly for the best really as i dont think she was actually broke up with her ex at the time but yeah fuck cold weather.

here's a picture from where i was stood inside said cave thing for reference


[close]

Thank you for the picture, it really helps provide context.
[close]
hahaha
At least you got some kinda hole that day.

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Re: Awkward Sexual Experiences
« Reply #2089 on: April 23, 2019, 04:47:33 PM »
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from around November time up until February I was kinda seeing this girl on and off, was a bit of a weird situation given she'd just broke up with her ex and shit but w/e I don't know that fool. In January or so we went out on a lil wilderness explore being that were both into that (for backstory we'd already kissed and shit by this point and were aware we both had feelings) and yeah shit was alright just walking around exploring talking shit happy as larry. We somehow end up on some mtb trails and from there we find this weird abandoned cave/alcove thing with a tiny hole in a wall to enter and she's all "go inside" so I'm like alright fuck it. inside this mfer is pitch black, couldn't see a few ft infront of me. So we're dicking around in there and we start kissing, starts getting a bit rougher shes scratching the fuck outta my back while im biting her neck and all that shit, starts stroking my dick through my trousers and im harder than fucking stonehenge swear on god i was boutta nut just from that. one thing lead to another and she's basically stood there with her tits out so im sucking/biting em with her hand down my pants shit is lit. eventually she just whispers "get it out" so i whip the fuckin thing out and she starts stroking me. now bare in mind this is January in england it was about -1c and her hands were cold as shit and as soon as she touched my dick shit just fuckin flopped. imagine sticking your dick in a fucking ice cooler shit was so cold. we just laughed it off and she's all "thats a shame i was gonna suck it" like bruhhhhhhhhhhhhhh come on. prolly for the best really as i dont think she was actually broke up with her ex at the time but yeah fuck cold weather.

here's a picture from where i was stood inside said cave thing for reference


[close]

Thank you for the picture, it really helps provide context.
[close]
hahaha
[close]
At least you got some kinda hole that day.

Thought for a moment you might of been getting freaky with a grizzly bear
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WobbleHeadBob

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Re: Awkward Sexual Experiences
« Reply #2090 on: April 24, 2019, 10:33:16 PM »
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from around November time up until February I was kinda seeing this girl on and off, was a bit of a weird situation given she'd just broke up with her ex and shit but w/e I don't know that fool. In January or so we went out on a lil wilderness explore being that were both into that (for backstory we'd already kissed and shit by this point and were aware we both had feelings) and yeah shit was alright just walking around exploring talking shit happy as larry. We somehow end up on some mtb trails and from there we find this weird abandoned cave/alcove thing with a tiny hole in a wall to enter and she's all "go inside" so I'm like alright fuck it. inside this mfer is pitch black, couldn't see a few ft infront of me. So we're dicking around in there and we start kissing, starts getting a bit rougher shes scratching the fuck outta my back while im biting her neck and all that shit, starts stroking my dick through my trousers and im harder than fucking stonehenge swear on god i was boutta nut just from that. one thing lead to another and she's basically stood there with her tits out so im sucking/biting em with her hand down my pants shit is lit. eventually she just whispers "get it out" so i whip the fuckin thing out and she starts stroking me. now bare in mind this is January in england it was about -1c and her hands were cold as shit and as soon as she touched my dick shit just fuckin flopped. imagine sticking your dick in a fucking ice cooler shit was so cold. we just laughed it off and she's all "thats a shame i was gonna suck it" like bruhhhhhhhhhhhhhh come on. prolly for the best really as i dont think she was actually broke up with her ex at the time but yeah fuck cold weather.

here's a picture from where i was stood inside said cave thing for reference


[close]

Thank you for the picture, it really helps provide context.
[close]
hahaha
[close]
At least you got some kinda hole that day.
[close]

Thought for a moment you might of been getting freaky with a grizzly bear

i for sure thought that was gonna end with her still being outside the cave and you got sucked off by the Blair WItch or some shit.

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Re: Awkward Sexual Experiences
« Reply #2091 on: July 10, 2019, 07:38:25 PM »
Let me first state that I didn't have sex with her. I didn't get off. She barely even touched my dick, but what follows was nonetheless an awkward sexual experience.

TL;DR - Massaged a girl's ass for half an hour. Didn't really get why.

A few days ago I matched with a girl on Tinder. She messages me first asking if I want to hang. I can't because of my stupid work schedule and it was already ~late~ for me. I should have just hung then. The next day I asked if she wanted to hang, but she took too long to respond so I figured it was just another night alone and jerked off and showered. After I came out of the shower I see she finally responded and told her I had work early in the morning. I didn't, but I wasn't about it at that point in the night. The next day I ask if she's down and she is. She calls, gets my address, and comes over. We're awkward and hold some boring conversation about uninteresting shit. She suggests we put on Star Trek. I do. We're sitting there awkwardly for a whlie then we get close and I tell her I'm going to start kissing her badly. We do boring middle school touching and shit for a good while, but she tells me she isn't trying to have sex. A let down, but whatever we still go at each other a little bit. After a while she tells me she should probably be leaving soon and I tell her to stay a while and she responds in enthusiasm that she can't believe someone is touching her butt. I confusedly ask why and she just states that's what she likes. She then rolls over onto the other side of the couch, sticks her ass in the air, and pulls her pants down a little. I rub her ass a bit and ask if she wants me to go down on her. Her response "No, I'm not ready for that. You would do that? Just rub it and spank me a little." So I do that for like half an hour. Or at least it seemed. Just sitting there massaging this girls ass while she kind of moaned and fell over me. It sucked and I was facing away from the TV so I couldn't see what was happening and even though the window was open there wasn't anything interesting going on out there either. It was just strange massaging an ass for what felt like too long. My arms were getting tired. I honestly feel like I was being pranked, that she's gone to all her friends and told them about the moron she got to rub her ass for half an hour. I messaged her again asking if she wanted to hang and only got a maybe. I shouldn't have stayed up as late as I did for that.

Anyone know if there really are girls out there that like having their ass handled like that? Is that a thing? Explain this shit to me.
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Re: Awkward Sexual Experiences
« Reply #2092 on: July 10, 2019, 08:32:53 PM »
Well...that is a little strange...especially if she was still mostly clothed.

It sucked and I was facing away from the TV so I couldn't see what was happening and even though the window was open there wasn't anything interesting going on out there either.

This is funny.

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Re: Awkward Sexual Experiences
« Reply #2093 on: July 11, 2019, 02:30:39 PM »
You should have defs tossed that salad 🥗

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

LordManHammer

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Re: Awkward Sexual Experiences
« Reply #2094 on: July 12, 2019, 09:17:09 AM »
So I got a few good awkward stories but one that comes to mind is when I was being a manwhore. I have an Irish accent and it has been a blessing and a curse since the time I was born to now as we speak.

So long story short I came to this country from Ireland when I was 9 I am from Downpatrick Ireland and my dad moved us around while the IRA carbombings and shit.

 I moved from Northern Ireland to NYC for a bit then NYC to Arab, Alabama absolute worst shit hole I can think of I mean Birmingham is dope for spots but still the south in the more rural parts have this deeply ingrained racist bullshit ideals and towards foreigners as well.

Now that I have said that I have had  no trouble with the ladies from chatting them up to what they say cute limericks and Irish sayings that made ladies swoon.

Well I am 19/20 during the time of this awkward encounter of sexcapades , I was like Braydon Szfrankski rolling in the pussy as they say, I had 3 gals I was hanging out with. Not once did they suspect me and if they did it was too late as I moved on.


 So here I am it is my birthday and I broke my board but I need a few boards and some shoes. I end up hanging out with all three at one point one was a rich girl that was 17 and had money to boot it was great but I couldn't stay with her I'd always chill with her and smoke and get down and bounce, the other was an older milf Karen skater mum that had a kid I met her at Rampage skatepark in Middleboro TN if anyone remembers? I would swap the the dick for a stick many many times, I remember a few times I'd clown her son like now I am daddy. The boy was okay at skating he could possibly be on here for all I know?!  Then there was this really cute Chinese American gal that I really liked she worked at The Gadzooks then turned into Hot Topic in Hamilton Place Mall.  Of all the gals I was hanging around with I fucked up with was her as she had an equally attractive identical twin sister, they both had a thing for me and I swear they swapped out with each other as there was a birthmark on her dimples on her lower back when I'd hit it doggystyle.


Well as I got older certain things became more important to me like a sense of being with one person who could match intelligence but was the opposite in many ways. Now mind you I was 19 20 going on 21 they were rad and good gals to me it just sucks when having to choose between the 3 at the time I was homeless and making my own shit happen albeit at contests and trying to shmooze anyone that had a team I could ride for.

Back to the ladies well milf I remember couple times I'd be asked to cock smack her not like joking around like take your cock out and hit me in the face...... I am like okay sure I got you, I'd try my hardest literally I guess my attempts resulted in something she liked as I stood over her as she's on her knees and I whipped my dong on her nose and made it bleed a bit. Me being young and naive I think oh god did I hurt you? she's into itlike goes bananas on my dick like a pornstar and gobbled my nut several times. The young 17 year old she had this thing where she'd hold her pee and hump a vibrator till she pissed on me. She'd want the atm and a creampie it was freaky as I am thinking to myself like wtf how you know about this shit? who'd she sleep with beforehand?  Well the asian gal was a sweetheart, we'd just talk naked and chill she'd be into skating and I taught her some shit, she was the one that would be nice and treat me well. 

I know this isn't awkward as the title goes more or less this is a self reflection of regret for my shitty actions, I loved being a charmer but as I got older shit needed to change from ladies to me.
Dueces Bitch's

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Re: Awkward Sexual Experiences
« Reply #2095 on: July 13, 2019, 11:17:21 AM »
i once got a blow job from a chick in the back seat of a car while her friend drove us around.
hopefully ty evans was there to film him laying on the ground in HD

Billy Bitchcakes

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Re: Awkward Sexual Experiences
« Reply #2096 on: July 17, 2019, 12:27:53 PM »
That ass fondling one reminded me of a story I read on Skateperception years ago tha still makes me laugh

"one time I was watching a movie with an EXTREMELY FUCKING HOT girl friend of mine, and she was practically laying ontop of me. I didn't know what the fuck to do because I'm so shitty with girls that I've never even been in contact with one before that (or afterwards actually). I knew I had to get something out of it... so I reached around and slowly started to put my hand in the back of her pants, so I could feel her ass. She jumped up, screamed, and shouted "what the fuck were you trying to do?" I couldn't think of anything so I said "i thought it was my ass"


I haven't talked to her since"
During sex to prevent myself from ejaculating I think about Osama Bin Laden running my dick through a sewing machine.

WastedHippy

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Re: Awkward Sexual Experiences
« Reply #2097 on: July 18, 2019, 10:22:55 PM »
Let me first state that I didn't have sex with her. I didn't get off. She barely even touched my dick, but what follows was nonetheless an awkward sexual experience.

TL;DR - Massaged a girl's ass for half an hour. Didn't really get why.

A few days ago I matched with a girl on Tinder. She messages me first asking if I want to hang. I can't because of my stupid work schedule and it was already ~late~ for me. I should have just hung then. The next day I asked if she wanted to hang, but she took too long to respond so I figured it was just another night alone and jerked off and showered. After I came out of the shower I see she finally responded and told her I had work early in the morning. I didn't, but I wasn't about it at that point in the night. The next day I ask if she's down and she is. She calls, gets my address, and comes over. We're awkward and hold some boring conversation about uninteresting shit. She suggests we put on Star Trek. I do. We're sitting there awkwardly for a whlie then we get close and I tell her I'm going to start kissing her badly. We do boring middle school touching and shit for a good while, but she tells me she isn't trying to have sex. A let down, but whatever we still go at each other a little bit. After a while she tells me she should probably be leaving soon and I tell her to stay a while and she responds in enthusiasm that she can't believe someone is touching her butt. I confusedly ask why and she just states that's what she likes. She then rolls over onto the other side of the couch, sticks her ass in the air, and pulls her pants down a little. I rub her ass a bit and ask if she wants me to go down on her. Her response "No, I'm not ready for that. You would do that? Just rub it and spank me a little." So I do that for like half an hour. Or at least it seemed. Just sitting there massaging this girls ass while she kind of moaned and fell over me. It sucked and I was facing away from the TV so I couldn't see what was happening and even though the window was open there wasn't anything interesting going on out there either. It was just strange massaging an ass for what felt like too long. My arms were getting tired. I honestly feel like I was being pranked, that she's gone to all her friends and told them about the moron she got to rub her ass for half an hour. I messaged her again asking if she wanted to hang and only got a maybe. I shouldn't have stayed up as late as I did for that.

Anyone know if there really are girls out there that like having their ass handled like that? Is that a thing? Explain this shit to me.

ahhaah I love that you made an account to post this story because it made my day, laughed super hard at the bold parts. Ass rubbing and a boring window to look out of haha

Frank

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Re: Awkward Sexual Experiences
« Reply #2098 on: August 11, 2019, 04:37:07 AM »
bro i'm sorry but i'm sure sloshing your whiskey dick against her apparatus doesn't actually count as losing your virginity. if that was the case, i would have lost mine with 13, and i'd tell everyone. it would also mean that i actually had sex with 3 out of 4 of my last casual dates(had sex with none of them, lol).

you don't need to cum(both) for it to count i guess but this awkward experience, albeit sexual, wasn't you losing your virginity. i mean you still seam clueless as what to do and bewildered by the concept of hooking up. losing your virginity usually comes with some "eureka!" effect.

also don't fist girls unless they are into it. it almost sounds the girl was clueless and untouched as well, or she might have had her period or something, but all that blood stuff isn't normal. also, if you puke blood, plz go to a doc, that isn't normal under any circumstance.

if you have trouble getting it up don't go for the meh types that you don't find as attractive. also tinder might not be a good way to lose your virginity, or it might? maybe there's some cougar out there who wants to ride you in. maybe you should write the fact that you are a virgin in your profile. some woman might want to help you out.

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Re: Awkward Sexual Experiences
« Reply #2099 on: August 11, 2019, 06:03:57 AM »
Damn dude that was good

Next time it gets like that you're totally justified to leave with your pride and your whiskey

I wouldn't have sat on the couch or started drinking after the first 2 red flags