Embarrassing Stories

I've had 'salad dressing' at a restaurant before though not my own. I was out with the wife and her bf and she whispered something to him. He excused himself and was gone for a bit. He came back and handed me a used condom. This was my dressing. It was pretty embarrassing. I'm sure other people saw as well.

 

In the early days of video cameras the size of two shoeboxes, my wife, myself and our girlfriend decided to make a videotape of us so we could view in decades later. We really believed VHS Videotape was going to be around 40 years later. We were stoned and horny so we did a lot of kinky threesome stuff, BDSM, girl on girl and then me with each girl separately. It was kind of raunchy since none of it was vanilla sex.

Long story short, we accidently gave our sex tape to my brother and sister-in-law when we switched to the latest and greatest new video format, 12" Laser DIscs. Since the tapes we gave them were several movies we copied off of Satellite TV, we are pretty sure that they noticed. They never said anything to us though.

We also wonder if they showed the tape to their friends. My brother-in-law would do that. The tape was very entertaining with all sorts of kinky sex acts. I think it was very flattering for us. So that was our most embarrassing sex moment, realizing that we gave the tape to family members. When we moved near them a few years ago they kept asking us questions about swinging in our retirement community as if we knew the answers. That gave us a good hint that they saw the tape. It also explains why we hardly see them anymore.

 

A few years ago, Mistress and I were staying in a little hotel (run by a married couple) in Switerland for a few days during a motrcycle trip.
I was in my CB6000 at the time, wearing only a pink neck scarf Mistress had tied on me, bound to the bed with scarves, and thoroughly gagged with several scarves too.
We heard a knock on the hotel room door, but before Mistress could shout "Don't come in!", in walked the wife who ran the hotel. She got an eyeful , apologised and quickly left!
Needless to say, I was rather embarrassed when we saw her at breakfast times and when coming and going from the hotel for the next few days....she definitely smirked a few times!
So embarrassing at the time, but a bit of a turn on now when I look back on it!

 

It’s times like these that really get your juices flowing. I had one similar this last January when on Vacation. I was tied to the bed after a spanking with my bum raised and my Mistress stopped out of the room for a few minutes. The door opened and I heard the words “Hiouse keeping “. I never say her face or knew who it was.
In your situation you have no reason to be embarrassed, the lady had no right entering your room, she should be the one that’s embarrassed.

 

My most embarrassing moment came about whilst i was playing tennis in a mixed doubles match at the time wearing a Steelpleasures balltrap chastity device, i had been wearing it for a while and all seemed well however during the match i obviously stretched a little too far for a couple of shots and mid point felt a sickening pain engulf me as one of my testicles slipped past the cock ring. I yelped slightly and felt a wave of sickness sweep over me but worse was the feeling of the other testicle now slipping through the large opening swiftly followed by my soft penis, still mid point i wildly hit the tennis ball high in the air just as i heard the thud of the steel device hit the playing surface and bounce. I bent down really quickly and grabbed the item and stuffed it into my tennis shorts and hoped no-one had noticed what it was. After the point was won by us we stopped for a drink and the discussion turned to did you know its an offence to drop a ball from your pocket onto the court during a game and i still to this day do not know whether that was them being sarcastic or just stating the rules. I now wear a full steel chastity belt which is firmly locked on under my tennis gear and the issues at least will never happen like this again.

 

Yup that would be embarrassing. I find it hard to believe that a cage could just drop off or a testicals slip through. Not that I don’t believe that it happens but I think it’s because my cages are secure and don’t move around much. Smaller ring, tighter fit, different ratio of ring to testicals size. What ever it may be I think I’m safe from This embarrassing moment.

 

its surprising just how small a space a ball can slip through though especially if you are sweating and make a sudden movement. I think a showlace around the waist tied to the device just in case is the answer..........its a bit like the retaining cables they now have on formula 1 cars to stop the wheels coming off. lol

 

Ha Ha what a comparison, so calling your cage a Ferrari is exceptable. LOL

 

I frequently wander the house in various states of undress (or slutty dress) and have had workmen show up unexpected. We have glass patio doors and most of our friends come to that entrance when visiting, and I've had to dive under tables or behind couches and pretend no one is home!

I've also dealt with cages slipping off, or pinching, and having to do the surreptitious shuffle / adjust to sort myself out - most of the time I get away with those though - after all, guys are always grabbing their junk.

For me, I think the most deliciously embarrassing moment came a few weeks ago. I had spent the day dressed in panties and a large padded bra with a leather drop collar padlocked on. We were going out for dinner, and my wife told me to stay dressed - but throw jeans and a T on. In the parking lot of the restaurant she told me I could take the large padded bra off - but she had legit forgotten the key to the collar. We were over an hour from home at this point, so nothing for it ... I pulled the collar of my T up over the padlock, left my sunglasses hang around my neck, and had a lovely dinner

 

Sometimes the best place to hide things...is in plain sight I enjoyed the story

 

Once my dad almost caught me dressed up when he showed up unexpectedly at my apartment and to stop him from coming in i lied and said i had peed myself to give me time to tidy up my clothes, shoes and bondage toys that were spread out in my spare bedroom/office where i was working from home.

 

I’ve had a few occasions when my thong has crept above my jeans while I’ve been bending down.
It’s a bit of a turn on if I’m honest.

 

Years ago I was having a drink with an old friend from school, catching up. There was never anything between us except being good friends. We'd been drinking in the beer garden for a while when I said I'd have to go for a pee. She told me not to. When I asked why, she grinned and said she wanted to see how long I could hold it for.

This sort of dominance totally turns me on and I sat back down and continued to drink. Eventually, of course, I was very close to the point of no return and told her so. She reached across and pushed against my bladder making me squirm. She told me if I really needed to go I could but in my seat where I was.

I looked around. There were quite a few people sitting around, drinking and talking. I couldn't do it. I laughed and shrugged, heroically.

Not long afterwards it just happened. I laughed at something she said and suddenly it just flowed. She looked at my face then straight away at my jeans. A big wet spot was forming and piss was leaking onto the ground. She was laughing while I tried to hide the fact that I was pissing myself though people were noticing.

Eventually I stopped and she announced it was time to go. I had to walk out of the beer garden, my jeans sopping wet, while she just kept laughing.

We walked back to her place where she let me shower and wash my jeans.

Totally embarrassing.

 

This was a good old thread. Anyone have any new stories?

 

One day I went went running (sports) and felt girly that day so I underdressed including a sportsbra. A very tight one.
After running I took a shower and left the house to my massage appointment.

The lady asked if I was wearing a bra before because of the marks on my skin....
I mumbled something about a compression shirt.

 

Those 'feeling girly' moments can lead to interesting interactions. I was in the midst of one myself. I had let my hair grow and had always wanted to put it in curlers and see how it felt. So i went to a beauty supply store, not the closest one, but one in a nearby town. I was so nervous going in, but i knew the things i needed. I'm sure my face was a light pink at least, as i browsed the shelves. But i got two sizes of curlers, a stretchy hair net, setting spray, hair spray, and a teasing style comb. When i put them on the counter, the clerk looked me over pretty good as she rang them up. As i began to pay, she asked if I was going to curl my hair. I couldn't think of anything else to say, but yes. She smiled broadly and told me to take lots of photos and post them. That everyone would enjoy seeing them. I know my face flushed a deep red at that point because it felt super hot. I just mumbled maybe, took my things and left. It was embarrassing but worth it later.

 

I was once complimented by the sales woman when I bought a bra in guy-mode.
She wore the same and she thought the bra was just awesome

 

I had a sales clerk tell me the panties I was buying was the same ones she got her husband. It wasn’t embarrassing per se more surprising! But it was nice to hear.

 

During the first few months of wearing a cage, it was all new, and my kh and I were really into the teasing. I was at a little league game in the bleachers and while my son wasn’t playing, was busy texting her.

She texted back, and we went back and forth, me being revved up. As an FYI, this is just months after having orgasms every day to once a week or less, and dripped all the time.

I wasn’t wearing any undies that day, had some cage issues and thought the air would help. Well I stood up in the bleachers and a lot of precum dripped down my leg. I was wearing cargo shorts, dark brown spots appeared where the precum touched the fabric, and an obvious amount of drippings ran down my leg. Somewhat like a quickly dripping faucet for a few seconds.

I was in the bleachers, so when I stood up, people to my left and right were still seated and faces at crotch level. I distinctly remember the woman to my right staring in confusion as she noticed. I sat back down as soon as I noticed her face and felt the wetness start to run. I hunched over a little and tried to nonchalantly wipe it all smooth but could see in the corner of my eye that at least she was still staring. I waited for a moment when the crowd was clapping and got up quickly and went to the bathroom.

After that, always wore undies. Although now I don’t drip that much anymore, still, lesson learned.

 

Not with chastity, but with xdressing.

Once I was parked on a NYC street changing into my maid's dress in the car. I was just about to pull the satin black and white maid's dress over my head when a guy taps on my window. I had to lower it a bit, and these were all non-tinted windows in a regular sedan. I lower it 1/2 way, there are clothes all around me, I'm 1/2 naked, with a puddle of a maid's dress in my lap, and the guy wants to know if it's okay to park on this side of the street until midnight. I say that yes, I had done it many times, he thanked me and left.

Other time I was in women's clothes, probably on the way to a party or something, and driving around NYC. The FDR was backed up so I got off on a side street to head over the West Side Highway. Anyway, a cop pulls me over. Lights, siren, whole bit. Worst nightmare. I pull over, he looks at me, I look at him. He simply says that there had been drug activity in the area. I told him I don't do drugs and was just heading over to the WSH because the FDR was jammed. He told me to have a nice night and sent me on my way.

Another time, I was in Vermont, dressed fully in women's clothes heading to a crossingdressing munch. I'm driving in Montpelier and notice a cop behind me. I drive super careful, hands at 10 and 2, and not a bit over the speed limit. Next thing I know, he hits the lights. I'm about to pull over, freaking out, and he pulls around me and zooms away, apparently on another call. JFC!

Another time, I'm at work and my wife calls me. She found a pair of women's high heels and wants to know who I'm having an affair with. I ask her what size they are. She says, um, women's size 14. I say, yes, they're mine; what woman has shoes that big? I tell her that since she won't wear high heels, I got some for myself. Weeks later she got me another pair as a gesture of acceptance. They were cute, but too small.

I have a couple more, but that's it for now.

 

I was in a store in NYC down in the village. I had stopped in to see what size corset I would take. The clerk said to undo the top of my pants so she could measure me. I had on latex briefs. All she said was nice panties

 

Did that lead to anymore conversation or it just sopped there?

 

just some chit chat
Couldn’t really talk more as they were getting busy
Only saw her one more time but again couldn’t really talk

 

We happened to have left the keys to one of my cages onthe bedside table.
There are letters on the key saying: BDSM

we forgot our housekeeper was going clean up that week...
She never mentioned it but who knows if she saw it ☺️

 

Have posted this in another thread here on CM. If we weren't so tired I would have been a lot more embarrassed

On our way back to Australia after our overseas holiday last year the plane landed early in the morning and we were both tired with very little sleep. Mr A wasn't locked but his chastity cages, along with my favourite dildo, strapon harness, cock ring, bottle of lube, cane, a belt and a box of condoms were in his suitcase inside a cloth shopping bag. My key was proudly on display around my neck though

We had nothing to declare and indicated this on our customs form. When we got to the front of the line the customs guy read our form, then said "Go with this officer" pointing to a female customs officer.

"Follow me over here and put your bags on the x-ray machine."
We did as instructed and Mr A placed our bags onto the machine.

The bags start to go through the machine and then they stop. The customs lady says "Mr A can you come around here?"

Mr A walked around the side of the x-ray machine to where the monitor is and she asks "Are they handcuffs?" pointing to the 2 base rings of the chastity cages that were visible on the screen.

"No" Mr A replied.
"They look like handcuffs" she says.
"What are they then?" she asks.
"They are chastity cages" says Mr A
"They are what?" she asks again.
"They are chastity cages, I'll show you" replies Mr A
"Collect your bags and bring them over to that table" she directed whilst pointing to a bench behind the x-ray machine.

We did as instructed and followed her over to the bench. The customs lady goes through the usual caution "Are these your bags, did you pack them yourselves, has anyone other than you placed anything in them, etc, etc?"

"I want to see what they are please" she tells us.

Mr A opens his bag and then pulls out our toy bag. He opens it up and he says he wasn't nervous but tired instead, and he fumbles around and out falls the box of condoms and the bottle of lube. I start to blush hoping that my favourite 9 inch dildo won't come falling out and bounce on the table and plonk on the floor

Mr A picks up the 2 cages and the base rings and shows them to the customs lady and says "They are chastity cages"

She looks for a couple of seconds and says with a big smile on her face "Thank you, you can go now"

Mr A packed everything back into his bag and we walked away smiling at each other that we had just been sprung by a total stranger

No doubt the customs lady told her coworkers about this kinky couple that she just searched and what she saw Did she Google chastity cages? Did she ask her coworkers have they heard of "chastity cages"

I think if we both weren't so tired or the customs area was a lot busier than it was we would've been more embarrassed than we where