Author Topic: Awkward Sexual Experiences  (Read 463312 times)

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Jim and Dan

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Re: Awkward Sexual Experiences
« Reply #2430 on: June 22, 2023, 09:14:19 AM »

Looks like it’s called sub coronal. Never heard of that but I like weird dick stories.

Imagine cumming out of your perineum.

So the end of the head was just smooth? Was there like massive foreskin? The images I’m coming up with seem to have a lot on the diagram for some reason.

I stumbled upon a random wikipedia article regarding the concept of the yaoi hole, illustrated below:



Apparently there is this notion in male-on-male homoerotic anime that penetration actually occurs in this yaoi hole as opposed to the anus. I reckon this yaoi hole is much like the perineum and could have the potential to cum, I'm sure it has happened but I haven't been buffing up on my homoerotic anime lately.

Now back to our regularly scheduled programming...

When I was 17 and in high school, me and two of my friends (T/H) would hang out with these 2 girls a lot, one of them being my friends ex (B) and the other (R) dating one of our other friends. There had been some sexual tension between between H and R as of late and it had been decided that we would all hang out one night, with liquor involved. So R decides to bring another friend (L) with them that night and T was going on and on about how he was going to fuck L that night. Now quick side note, T was a virgin at the time and very socially awkward, possibly suffering from Asperger's syndrome, while also looking a lot like Sideshow Bob. We start drinking and it's pretty obvious that H and R are going to hookup, so T continues to opine away how he's going to be getting with L tonight. Now mind you, I had a steady, long-term girlfriend at that time, so I had no intentions of getting with anyone. But little did I know, but L had her sights on me that night. So T had a really nice house with this massive tiered porch complete with a screened-in gazebo and it was located right next to H's house. T continues to boast about how he's getting laid tonight and that L is "his", until the point I had heard enough and said "fuck it", proceeding to succumb to L's advances. We start making out in the gazebo and it's getting hot, so I proceed to put my hand down L's pants and start going to town on possibly the wettest coochie I've ever seen to this date. I'm doing my thing, she's panting heavy and then all of a sudden, out of the corner of my eye I see T. We lock eyes and the sheer look of anger on his face is something that I will never forget and without breaking eye contact I go harder and harder as he walks away enraged. Now this might make me seem like a fucking asshole but let me assure you, T had no chance of getting with L ever, it just wasn't in the cards for various reasons. So we end up going next door to H's house and go down to his furnished basement, clothes start coming off and low and behold the longest nipples I have ever seen in real life, it was quite an experience to have them in my mouth due to the time it took to remove the nipple from the mouth when going from breast to tip. One finger begins to penetrate the wetness between her legs, then another, and another, and another until I actually tried to fist her and almost succeeded. Our genitals converge to form a mortise and tenon joint, thrusting passionately as the moment takes hold, seconds turn into minutes and gradually they stack upon another. Then all of a sudden L asks if I have a condom and bare in mind, there had been a solid 10-15 minutes of fluid exchange by this point and as quickly as it started, it was over, as I had no condom on me. The resulting time was spent intimately cuddling, our naked bodies conjoined, as we drifted off to sleep and awkwardly put our clothes back on in the morning, never to speak of it again. Granted I ended up telling my girlfriend about this years later, something that I deeply regret and felt shameful for participating in, but I was young, insecure and welcomed any sexual attention from women for a long time after. As for T, well, he did end up losing his virginity the next year when he joined the football team, participating in the gang rape of an inebriated and unconscious classmate in his basement, something that altered my perception of him into absolute human trash.

Not as out-there as many of the other ones I've read on here but awkward nonetheless.
« Last Edit: June 22, 2023, 10:33:53 AM by Jim and Dan »
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Joust Ostrich

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Re: Awkward Sexual Experiences
« Reply #2431 on: July 07, 2023, 09:16:59 PM »
Expand Quote

Looks like it’s called sub coronal. Never heard of that but I like weird dick stories.

Imagine cumming out of your perineum.

So the end of the head was just smooth? Was there like massive foreskin? The images I’m coming up with seem to have a lot on the diagram for some reason.
[close]

I stumbled upon a random wikipedia article regarding the concept of the yaoi hole, illustrated below:



Apparently there is this notion in male-on-male homoerotic anime that penetration actually occurs in this yaoi hole as opposed to the anus. I reckon this yaoi hole is much like the perineum and could have the potential to cum, I'm sure it has happened but I haven't been buffing up on my homoerotic anime lately.

Now back to our regularly scheduled programming...

When I was 17 and in high school, me and two of my friends (T/H) would hang out with these 2 girls a lot, one of them being my friends ex (B) and the other (R) dating one of our other friends. There had been some sexual tension between between H and R as of late and it had been decided that we would all hang out one night, with liquor involved. So R decides to bring another friend (L) with them that night and T was going on and on about how he was going to fuck L that night. Now quick side note, T was a virgin at the time and very socially awkward, possibly suffering from Asperger's syndrome, while also looking a lot like Sideshow Bob. We start drinking and it's pretty obvious that H and R are going to hookup, so T continues to opine away how he's going to be getting with L tonight. Now mind you, I had a steady, long-term girlfriend at that time, so I had no intentions of getting with anyone. But little did I know, but L had her sights on me that night. So T had a really nice house with this massive tiered porch complete with a screened-in gazebo and it was located right next to H's house. T continues to boast about how he's getting laid tonight and that L is "his", until the point I had heard enough and said "fuck it", proceeding to succumb to L's advances. We start making out in the gazebo and it's getting hot, so I proceed to put my hand down L's pants and start going to town on possibly the wettest coochie I've ever seen to this date. I'm doing my thing, she's panting heavy and then all of a sudden, out of the corner of my eye I see T. We lock eyes and the sheer look of anger on his face is something that I will never forget and without breaking eye contact I go harder and harder as he walks away enraged. Now this might make me seem like a fucking asshole but let me assure you, T had no chance of getting with L ever, it just wasn't in the cards for various reasons. So we end up going next door to H's house and go down to his furnished basement, clothes start coming off and low and behold the longest nipples I have ever seen in real life, it was quite an experience to have them in my mouth due to the time it took to remove the nipple from the mouth when going from breast to tip. One finger begins to penetrate the wetness between her legs, then another, and another, and another until I actually tried to fist her and almost succeeded. Our genitals converge to form a mortise and tenon joint, thrusting passionately as the moment takes hold, seconds turn into minutes and gradually they stack upon another. Then all of a sudden L asks if I have a condom and bare in mind, there had been a solid 10-15 minutes of fluid exchange by this point and as quickly as it started, it was over, as I had no condom on me. The resulting time was spent intimately cuddling, our naked bodies conjoined, as we drifted off to sleep and awkwardly put our clothes back on in the morning, never to speak of it again. Granted I ended up telling my girlfriend about this years later, something that I deeply regret and felt shameful for participating in, but I was young, insecure and welcomed any sexual attention from women for a long time after. As for T, well, he did end up losing his virginity the next year when he joined the football team, participating in the gang rape of an inebriated and unconscious classmate in his basement, something that altered my perception of him into absolute human trash.

Not as out-there as many of the other ones I've read on here but awkward nonetheless.

Had to look up mortise and tenon joint.  Strange choice.
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jgonzalez

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Re: Awkward Sexual Experiences
« Reply #2432 on: November 24, 2023, 10:54:48 AM »
Bump

Any stories from this cuffing season?

Myself, no luck. Maybe some tales will alleviate the maladie of dryness

nothing's been the since same

pugmaster

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Re: Awkward Sexual Experiences
« Reply #2433 on: November 24, 2023, 11:19:13 AM »
Bump

Any stories from this cuffing season?

Myself, no luck. Maybe some tales will alleviate the maladie of dryness

I had my fist inside of a turkey yesterday, if that counts
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FUBAR

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Re: Awkward Sexual Experiences
« Reply #2434 on: November 24, 2023, 01:01:04 PM »
Expand Quote
Bump

Any stories from this cuffing season?

Myself, no luck. Maybe some tales will alleviate the maladie of dryness
[close]

I had my fist inside of a turkey yesterday, if that counts
I’ll allow it.

behavioralguide

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Re: Awkward Sexual Experiences
« Reply #2435 on: February 29, 2024, 11:35:51 AM »
As a teen, first time I bought condoms at the grocery store;
 This hot(-ish) girl clerk who was selling them from behind the counter - they have to keep them there so all the awkward teens (like meself) don't just pocket them - , asked me if I wanted them large or small.
I mumbled, asking if she also had like a medium or something in between.
She didn't really get what I was saying so I had to repeat my question; she then explained they only had 24 or 6 packs and how big of a pack I wanted.
I don't think she understood/noticed my confusion/relief/pain

RoaryMcTwang

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Re: Awkward Sexual Experiences
« Reply #2436 on: February 29, 2024, 11:33:36 PM »
As a teen, first time I bought condoms at the grocery store;
 This hot(-ish) girl clerk who was selling them from behind the counter - they have to keep them there so all the awkward teens (like meself) don't just pocket them - , asked me if I wanted them large or small.
I mumbled, asking if she also had like a medium or something in between.
She didn't really get what I was saying so I had to repeat my question; she then explained they only had 24 or 6 packs and how big of a pack I wanted.
I don't think she understood/noticed my confusion/relief/pain

This is adorable!

9inchdeck

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Re: Awkward Sexual Experiences
« Reply #2437 on: March 17, 2024, 12:14:32 PM »
I was having sex with this girl one time doggy style on her couch. I pulled out and came on her butt cheek and went to get a towel to wipe it off. After I walked away, her dog jumped up onto the couch and started licking the cum off her ass. She started screaming “Oh my god ew!!” So I ran over and had to push the dog off the couch to get him to stop. I think we only hung out like one more time afterwards

ok boomer

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Re: Awkward Sexual Experiences
« Reply #2438 on: March 20, 2024, 06:28:45 PM »
Wonder if she nicknamed you “doggy cummer “

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Re: Awkward Sexual Experiences
« Reply #2439 on: March 20, 2024, 06:41:07 PM »
I have a lot of heinous stories. A little buzzed right now so I’ll hit you with a quick one.

Had my girlfriend over in high school. My basement had a separate entrance so I used to sneak her in regularly. For whatever reason my dad ends up coming home, hears me watching portlandia in the basement, grabs a bowl of cereal and heads down to check up on me. I’m panicking telling her to hide somewhere. She can’t find a spot so I throw her a blanket and she gets like next to the couch and hides under the blanket on all fours, trying to get super small and lean up against the back of the couch. My asshole dad sees her, I see him crack a little smile, goes “oh this is portlandia, sick” and watches two full fucking episodes with me while this poor girl is huddled up trying to be quiet.

Lol. I can’t wait to do this to my son now