Most embarrassing moment?

[andthighbootsforall]

A couple of decades ago I briefly dated a girl that was well above my station. By anyones standard she would truly have been looked as a beautiful young lady!

After she broke up with me I always held out hope that we might be able to rekindle things and see what might happen long term.

One night she called me and needed some floppy disks to create a backup or to install some virus software. Whatever the hell it was she needed floppy’s.
I agreed to get them to her somehow.

About two weeks later she calls me and asks me what the hell was on those disks. I was like “Oh shit.” She then proceeded to ask what the hell would ever compel me to keep images like that?

I had a number of enema related photos and some of them were messy. lol Talk about a sinking feeling! I was totally deflated!

At the end of the day I married a great gal and had great kids. My regret is that every moment with this gal was me trying to spoil her and be a gentleman, but that disk stuff is probably what she remembers most.

 

[Leffe6]

Most embarrassing happened twice to me. I sleep in the nudes, most of the time. One night I got up to go to the bathroom, naked of course. My son's girlfriend was standing at the door when I opened it. The second one was the same scenario, except my daughter in law. It was a bit embarrassing for her as well as she was braless and only had panties on. She had a nice set of tits, though. Might have to write a fantasy story about that.

 

[loveupskirt]

On our honeymoon cruise, my wife had been arousing and teasing me all night. When we got back to our room, she continued as we made out and got undressed. As I was over her and ready to put it in, she reached up and touched my cock and I proceeded to shoot my load all over her thigh before I ever got in her! We still laugh about it 28 years later.

 

[trinething1ns]

When I was in college, I got caught by my boss’s wife jerking off in their only (unisex) bathroom. She was trying to go to the bathroom and I just forgot to lock the door. I have had fantasies about it since, but in the moment I was really embarrassed.

 

[trinething1ns]

She giggled. And said she knows “guys my age” have a hard time controlling ourselves. She the said more sternly to lock the door. Good thing it wasn’t a customer.

 

[Swuq]

Met a top online that turned out to my wife’s ex-boyfriend. We were both pretty shocked when he showed up. We made the best of it and he used my mouth and hole for his pleasure. Met a few more times before we went our own way.

 

[SmoothAndSweet]

Being caught naked in an ABS

 

[Kimlikes]

I’ve had so many , but the 1 that comes to mind is my Vinilla best friend caught me self pleasuring, , she arrived an hour early, and caught me pre shower naked on the bed toy in both hole flicking My clit and trying to pinche a nipple, very close to my goal , the first I knew was hear her laugh. I jumped up , toy fell on the floor all wet and shiny from lube and come, .
She only laughed more , .As she walked out of my bedroom she said I’ll give you another 10 minutes and shut the door. What I didn’t know was she had taken a picture of me , she had sent it to her husband and mine. Bugger

 

[OddLove]

I managed to avoid anything too disastrous because I had one incident when I was younger. I was at my cousins apartment and they had porn DVDs. So when they left to drop my cousin off at work I watched a DVD. While I was jerking off I heard my cousins girlfriend unlocking the door a lot sooner than I expected. I panicked and ran into the bathroom naked without even turning the TV off. I asked her to bring me my clothes. Then after I got dressed and finally came out of the bathroom she pretty much told me "it's normal" and "you don't need to be embarrassed" then we acted like it never happened.

Ever since then I've been very careful about when and where I masturbate.

 

[YourSecretDesires]

Being caught naked in an ABS

What's an ABS?

 

[YourSecretDesires]

Most embarrassing happened twice to me. I sleep in the nudes, most of the time. One night I got up to go to the bathroom, naked of course. My son's girlfriend was standing at the door when I opened it. The second one was the same scenario, except my daughter in law. It was a bit embarrassing for her as well as she was braless and only had panties on. She had a nice set of tits, though. Might have to write a fantasy story about that.

Hmm, doesn't sound totally accidental...

 

[YourSecretDesires]

Once my family was staying in a hotel room on a trip, my parents in one bed and my siblings and I in another. I remember waking up to a wet dream when we were all asleep in the middle of the night. I don't think anyone else knew but I was mortified. I even remember the dream, a classmate/friend was giving me a BJ.

 

[OddLove]

What's an ABS?

Pretty sure it stands for "Adult Book Store", apparently those can be hook up spots from what I've read online.

 

[Leffe6]

What's an ABS?

Some of the adult book stores have movies areas in the back where they could have glory holes. I've always wanted to try one but get nervous when I think what could be on the other side.

 

[YourSecretDesires]

Some of the adult book stores have movies areas in the back where they could have glory holes. I've always wanted to try one but get nervous when I think what could be on the other side.

Yeah glory holes sound fun in theory but it might be a little too much mystery in reality, lol.

 

[Sgts19]

Two cum to my head but if I sat down and thought I'm sure they'd be more

My HS girlfriend and I were in a 69 when her sister suddenly opened the door, no it wasn't like a Lit story she didn't jump in with us. Lots of crying I remember that. Her parents were gone for the weekend and her sister didn't live there.

Got caught mid cum watching my ex fucking someone else, not good it was the campus police. Walked around a lot with my head down and a hat for weeks

 

[dow7]

I first posted this on the “humiliation” board but this board is better for an extended remix version. i just told a gay friend that i wanted her to do me w/ a strap on. i'm embarrassed. Ive known her for years, she had surgery and needed me to change a bandage on her ass. I said sure. Day of the meet up she asks me to bring over some whiskey. I felt weird and told her I couldn’t do it. So I regret not going over cos I wanted to see her ass. So I called and she said she was flattered by my attention. (same age btw, old!) we started texting about sex and I haven’t heard from the her-I knew I’d gone too far. She said if I went too far and said something inappropriate she'd be womanly and say something, instead i havent heard from her so i take that as a no and this is after telling me about her not wearing panties and she hasn’t worn hose since she had hair. i asked if she used a strap on and she said yes and i said id like her to use one on me. crickets. deep sigh. it's funny that she doesnt wear panties cos i wanted to smell hers! So I haven’t spoken to her in two weeks and I want to drop a line and apologize cos I consider her a friend. But this is embarrassing but it also turns me on.

 

[dow7]

i was gonna shove a plug up my ass and jack off about the lesbian but the landscapers appeared

 

[SuperSissy]

I was 18, it was late at night, and I was at my girlfriend's house. We thought we were alone, and started fucking sideways on the living room couch under a blanket. Her sister was home, and came into the room and started talking to my GF. She was always a real prick, and she guessed what what was going, so she tortured us by having this long conversation while we stayed still and pretending all was well. Nevertheless, it all sent me over the edge and since we weren't using birth control I had to pull out to come as best I could. I came all over my GF's back and it ran out and down and all over the couch. My GF was really PO'd about that, and even more about having to wait to see if she got her period.

 

[Bassytian]

Farting loudly during a class presentation, that shit echoed too!

 

[SmoothAndSweet]

my GF making me suck her at a party

 

[easyoff]

my GF making me suck her at a party

Sounds like a fun party.

 

[SmoothAndSweet]

Sounds like a fun party.

the more one drinks the more fun it is,,,up to a point

 

[Dcharger]

I’ve had so many , but the 1 that comes to mind is my Vinilla best friend caught me self pleasuring, , she arrived an hour early, and caught me pre shower naked on the bed toy in both hole flicking My clit and trying to pinche a nipple, very close to my goal , the first I knew was hear her laugh. I jumped up , toy fell on the floor all wet and shiny from lube and come, .
She only laughed more , .As she walked out of my bedroom she said I’ll give you another 10 minutes and shut the door. What I didn’t know was she had taken a picture of me , she had sent it to her husband and mine. Bugger

Sorry I didn't get to see. Hehe.

 

[bobb64]

my youngest son coming into the house while i was giving a guy a blow job.