Most embarrassing sex moment - GLBT style...

[lisaharlot]

I’ve been walked in on a couple of times but it was by people who knew me and knew my tastes and proclivities so it was awkward but I wouldn’t say embarrassing. My fist time doing force nudity in front of others was super embarrassing. It’s consensual, for the audience too by being the inly one wearing clothes or having my skirt pulled up to demonstrate a lack of underwear got me a good blushing.

 

[Marcs4u]

Embarrassing but, turned me on...

So, I love walking around, in public, plugged and wearing sexy lingerie under my street clothes. Usually, I have my small, jeweled plug in and just go about my business with no issues butt one day, I was very horny and decided to wear my large Doc Johnson while I did my shopping. All was going well, except for my chubby clitty, until I felt a little gas start to build up just as I was in the line to check out. Well, I couldn't let it out without the plug trying to pop out and slide down my pants leg to the floor! I was squirming like a worm on a hook, trying to keep it in, when I noticed the young lady behind me smirking and on the verge of giggling. I knew she had to have noticed the bump in the back of my tight sweat pants as the plug was trying to escape butt, there was nothing I could do to stop it from happening. Thankfully, my g-string was helping to keep it from coming out completely! I made it through the line and to my car without it popping out but, as I sat down, the trapped gas squeezed past in a loud fart...I'm just glad there was noone but me to hear it!

C'mon y'all, Don't be shy... What's your most embarrassing sex-related story?!

A hotel housekeeper walked in as I was sucking a guys cock. Him on the bed and I was on all fours with a butt plug in. I never noticed but he told me after she came in that she looked straight into his eyes, down at my business spread directly in here line of sight, and quietly slipped back out. I stayed there for 2 more nights. She just smirked every time I passed her in the hallway.

 

[bimori]

And her response...!?!?

1st she made me swallow ever drop then whispered in my ear that I would always do the cum clean up. So if she let me cum in her I would have to cum up every drop. But sometimes she would make me stop and selfsuck while she toyed my ass. She would fuck my ass until I had every drop in my mouth.

 

[OtherwisePrint6210]

So, I love walking around, in public, plugged and wearing sexy lingerie under my street clothes. Usually, I have my small, jeweled plug in and just go about my business with no issues butt one day, I was very horny and decided to wear my large Doc Johnson while I did my shopping. All was going well, except for my chubby clitty, until I felt a little gas start to build up just as I was in the line to check out. Well, I couldn't let it out without the plug trying to pop out and slide down my pants leg to the floor! I was squirming like a worm on a hook, trying to keep it in, when I noticed the young lady behind me smirking and on the verge of giggling. I knew she had to have noticed the bump in the back of my tight sweat pants as the plug was trying to escape butt, there was nothing I could do to stop it from happening. Thankfully, my g-string was helping to keep it from coming out completely! I made it through the line and to my car without it popping out but, as I sat down, the trapped gas squeezed past in a loud fart...I'm just glad there was noone but me to hear it!

nice story! And I heard it from here. Wondered where it came from.

 

[cubbyfire04]

So, I love walking around, in public, plugged and wearing sexy lingerie under my street clothes. Usually, I have my small, jeweled plug in and just go about my business with no issues butt one day, I was very horny and decided to wear my large Doc Johnson while I did my shopping. All was going well, except for my chubby clitty, until I felt a little gas start to build up just as I was in the line to check out. Well, I couldn't let it out without the plug trying to pop out and slide down my pants leg to the floor! I was squirming like a worm on a hook, trying to keep it in, when I noticed the young lady behind me smirking and on the verge of giggling. I knew she had to have noticed the bump in the back of my tight sweat pants as the plug was trying to escape butt, there was nothing I could do to stop it from happening. Thankfully, my g-string was helping to keep it from coming out completely! I made it through the line and to my car without it popping out but, as I sat down, the trapped gas squeezed past in a loud fart...I'm just glad there was noone but me to hear it!

I've been there haha! I use tight compression shorts. Seems to be better at keeping the cheeks from giving up. And that large doc Johnson is no joke when it comes to long term wear... I've got one in now and I'm always afraid I'll never be able to get it back out lol

 

[timmyid2]

I've been embarrassed a few times. There were the typical times that my girl and I were caught necking behind the shed or in the tree house. I had my hand up her blouse as often as possible and she loved it too. It was still embarrassing when my brother caught us.

But it was later, when I met my first boyfriend that I got really embarrassed. I was slim for my size, only 127 pounds but 5'9". Jim was 50 years older, and also slim but his physique was sculpted by hard work in the California sun. His dark tan ended at his belt line but his muscles were well distributed from shoulders to belly to legs. He was the first to seduce me and I spent as much time as possible at his house. Of course we were in the closet since in those days an old man with a younger one was considered a pedophile and might find himself strung up somewhere.

I was still living with my parents at the time. They knew that I was spending a lot of time with Jim, but one day I came home with a huge hickey on my neck. Mom spotted it and knew instantly what it was. She asked where I'd gotten it. I was sure that she had figured out that just hours before I was naked in Jim's bed as his wonderfully soft lips explored every part of my body.

Fortunately she threw me a lifeline by asking if I'd met a new girl. I quickly made up Sue, who was hot but to impetuous and promiscuous so I was not planning to see her again.

Not THE most embarrassing, but close to it.

 

[cubbyfire04]

I've been embarrassed a few times. There were the typical times that my girl and I were caught necking behind the shed or in the tree house. I had my hand up her blouse as often as possible and she loved it too. It was still embarrassing when my brother caught us.

But it was later, when I met my first boyfriend that I got really embarrassed. I was slim for my size, only 127 pounds but 5'9". Jim was 50 years older, and also slim but his physique was sculpted by hard work in the California sun. His dark tan ended at his belt line but his muscles were well distributed from shoulders to belly to legs. He was the first to seduce me and I spent as much time as possible at his house. Of course we were in the closet since in those days an old man with a younger one was considered a pedophile and might find himself strung up somewhere.

I was still living with my parents at the time. They knew that I was spending a lot of time with Jim, but one day I came home with a huge hickey on my neck. Mom spotted it and knew instantly what it was. She asked where I'd gotten it. I was sure that she had figured out that just hours before I was naked in Jim's bed as his wonderfully soft lips explored every part of my body.

Fortunately she threw me a lifeline by asking if I'd met a new girl. I quickly made up Sue, who was hot but to impetuous and promiscuous so I was not planning to see her again.

Not THE most embarrassing, but close to it.

Whew! Close call!

 

[timmyid2]

As time goes on, it's amazing how we find less and less to be truly embarrassing. In my teens I had a motor cycle accident and was brought to the ER. I broke the cardinal rule of always wearing clean underwear "just in case I was in an accident". I was going commando that day. I was mortified to have the nurses cut away my torn and bloodied jeans only to find that I had no underwear on. To make matters worse, knowing that they were going to catch me naked caused a hard on just like most everything did at that age. I was mortified!

Fast forward 40 years. I come out of a local cruising place after being corn-holed by a guy who's dick was much wider than expected. The bathroom is out of order, so I walk to the car with the feeling of cum and lube running down my leg. My asshole's been stretched and I can't hold it in. I grab a bottle of water from the car and use it to rinse my mouth well. Then I grab the roll of paper towels from the trunk and bend over to clean off as much of the mess in my crack as I could. Lastly, I had 100 miles left to drive that day, so I put a plastic bag on the seat to protect it and pulled down my gym shorts to make an makeshift diaper from a hand towel.

As I pulled my pants back up and slipped into the driver's seat I noticed that there was a man sitting in the car next to mine. He'd been watching me the whole time and had a big grin on his face. I just smiled at him and waved.

 

[cubbyfire04]

As time goes on, it's amazing how we find less and less to be truly embarrassing. In my teens I had a motor cycle accident and was brought to the ER. I broke the cardinal rule of always wearing clean underwear "just in case I was in an accident". I was going commando that day. I was mortified to have the nurses cut away my torn and bloodied jeans only to find that I had no underwear on. To make matters worse, knowing that they were going to catch me naked caused a hard on just like most everything did at that age. I was mortified!

Fast forward 40 years. I come out of a local cruising place after being corn-holed by a guy who's dick was much wider than expected. The bathroom is out of order, so I walk to the car with the feeling of cum and lube running down my leg. My asshole's been stretched and I can't hold it in. I grab a bottle of water from the car and use it to rinse my mouth well. Then I grab the roll of paper towels from the trunk and bend over to clean off as much of the mess in my crack as I could. Lastly, I had 100 miles left to drive that day, so I put a plastic bag on the seat to protect it and pulled down my gym shorts to make an makeshift diaper from a hand towel.

As I pulled my pants back up and slipped into the driver's seat I noticed that there was a man sitting in the car next to mine. He'd been watching me the whole time and had a big grin on his face. I just smiled at him and waved.

Ah... The old cum/lube aftermath. Happened to me quite often with an old friend of mine who was a VERY heavy cummer. The first time was in a Target and I had on olive dress pants. I felt it happen and speed walked back to the car afraid it was... ahem... something else.

Got home and peeled everything off only to find a milky sticky mess all the way down my backside to my ankles. Now I know lol.

 

[OpenMouth]

I would say being over enthusiastic with a guy's cock and a sharp bit on one of my teeth drawing blood. It freaked him out.

It was such a shame - nice big tool, big screen with delicious tranny porn showing... He genuinely seemed to be in pain! Guy did kick boxing as well, he said getting his head punched wasn't as bad.

He did contact me a few times afterwards for a meet, because he'd forgotten who I was. Every time I reminded him he never replied!

 

[tristantrotsky]

Teeth

I would say being over enthusiastic with a guy's cock and a sharp bit on one of my teeth drawing blood. It freaked him out.
It was such a shame - nice big tool, big screen with delicious tranny porn showing... He genuinely seemed to be in pain! Guy did kick boxing as well, he said getting his head punched wasn't as bad.
He did contact me a few times afterwards for a meet, because he'd forgotten who I was. Every time I reminded him he never replied!

Most blowjob guide tutorials tell the aspirant cocksucker to keep teeth well out of the way of the sensitive penis-skin. I beg to disagree. All elements of the mouth can be brought into play in the quest towards that single objective of giving sensual joy. A little gentle encouraging nip with the teeth can be an extreme erotic stimulation to the friend I happen to be sucking. Then taking the flared heart-shaped glans into my mouth, closing my teeth very softly just below the ridge of the cock-head, trapping the head in that way, and tugging in a playfully arousing way, that action has him groaning with pleasure. Once trapped inescapably in my mouth in that way I can then lavish the glans with my tongue to my hearts content, and all he can do is squirm. Later… once he’s cum in my mouth, I squeeze the cock-head gently between my teeth, encouraging it with just enough pressure to coax the last oozing beads of spunk to leak out onto my greedy tongue.

 

[tristantrotsky]

Cock-sucking In The Time Of Pandemic

Met an old friend while walking on the canal towpath today. We were both wearing Covid-masks, we talked for a while, then walked back to where he’d parked his car. He sat in the driver’s seat. I sat in the passenger’s seat. I reach out, unzip his pants, take his cock out – pull my mask down sufficiently below my chin, lean over and begin sucking him off. Not the biggest cock I’ve ever sucked, but a very pleasant seven inches can be very satisfying, as I’m sure you know. We only pause briefly as an elderly couple walk by, and they glance curiously into the car. I wait impatiently until they’ve gone, then resume sucking that delicious big cock until he grunts and spunks off in my mouth... It’s wonderful to meet up with old friends again. We exchange phone numbers before we part. It’s only some time later, when I get back home, that I realise I have a big spunk-stain down the side of my mask which must have been very noticeable as a walked…

 

[4yourpleasureiam]

Spraying my cum as I walked to the bed occupied by a naked lady who expected some stimulation.

 

[Clintdear]

I am a sissy for boyfriends. I’ll wear whatever they buy me.
I was at a boyfriends apartment and in bed with him after a rousing evening. Suddenly the fire alarm goes off. (Not that uncommon here), then he tries the light and the power is out. Then the fire department shows up. This is not a false alarm! It’s getting real.
Using our cell phones for light I can’t find much. I’m only wearing women’s pink silky sleep shorts. I grabbed a winter jacket mostly by feel out of his closet. I cant find shoes or socks. The firemen are on the bullhorn telling us to evacuate. All kinds of stomping in the hall way. I’m getting scared, tears and panic are imminent. Suddenly my boyfriend takes my hand and leads me out.
So there I am with my boyfriend in an army type jacket with women’s pink silky sleep shorts and red toenails. I was quite a sight. People looked at me like I had two heads. My longish curly hair was mused and I’m small and wimpy. I hoped to God they think I am a girl. So my every thoughtful boyfriend takes me by the hand to his car and we go to his sister’s place and go back to bed.
I ended up wearing her clothes until the apartment was opened back up. We had no damage, just a crazy experience.

 

[2tallpaul]

We were headed to the other F of a FMF friendship to swim in her pool. My girlfriend convinced me to wear a summer dress to appear all fem for a three way. She told me to hold her hand and close my eyes as I was led to the pool area. Like a surprise party for her group, I met them all in a dress, never been cross dressed in public and she was into my cross dressing to begin with, I had been dealing with my first bi experience within the prior week and I turned red as a stop light. That night turned into one of my best nights ever, I was outed to an applause, realized I'm a bottom and had my first gang bang in front of a group. I learned that night that there is a whole lifestyle of kink out there and I was welcomed in.

 

[saintcero]

We were headed to the other F of a FMF friendship to swim in her pool. My girlfriend convinced me to wear a summer dress to appear all fem for a three way. She told me to hold her hand and close my eyes as I was led to the pool area. Like a surprise party for her group, I met them all in a dress, never been cross dressed in public and she was into my cross dressing to begin with, I had been dealing with my first bi experience within the prior week and I turned red as a stop light. That night turned into one of my best nights ever, I was outed to an applause, realized I'm a bottom and had my first gang bang in front of a group. I learned that night that there is a whole lifestyle of kink out there and I was welcomed in.

What a happy experience for you. Did it waken an inner slut in you? That is what I fear would happen if I indulged at that level

 

[stargame]

I am a sissy for boyfriends. I’ll wear whatever they buy me.
I was at a boyfriends apartment and in bed with him after a rousing evening. Suddenly the fire alarm goes off. (Not that uncommon here), then he tries the light and the power is out. Then the fire department shows up. This is not a false alarm! It’s getting real.
Using our cell phones for light I can’t find much. I’m only wearing women’s pink silky sleep shorts. I grabbed a winter jacket mostly by feel out of his closet. I cant find shoes or socks. The firemen are on the bullhorn telling us to evacuate. All kinds of stomping in the hall way. I’m getting scared, tears and panic are imminent. Suddenly my boyfriend takes my hand and leads me out.
So there I am with my boyfriend in an army type jacket with women’s pink silky sleep shorts and red toenails. I was quite a sight. People looked at me like I had two heads. My longish curly hair was mused and I’m small and wimpy. I hoped to God they think I am a girl. So my every thoughtful boyfriend takes me by the hand to his car and we go to his sister’s place and go back to bed.
I ended up wearing her clothes until the apartment was opened back up. We had no damage, just a crazy experience.

My mom caught me totally dressed in her panties, bra, and panyhose, and white slip. She walked in on me laying in her bed as as I creamed into her panties and soaking her pantyhose.
Just just said, that's ok, but let me wash everything.

 

[2tallpaul]

What a happy experience for you. Did it waken an inner slut in you? That is what I fear would happen if I indulged at that level

Slut, sissy whatever title. Yes it did awaken. Fortunately the group I referred to plays together and stays together. We have a doctor in the group and STD's are checked. If you plan on playing outside the group, don't be a part of it. Safety first. Until you have been spit roasted and gang banged did I realize why some women love it. Watching my girl friend cum multiple times with more than one partner is incredible. Two years ago had you toid me I would be shaved, in a dress, multiple partners and loving it, I would have asked what planet you were from.

I've met some really nice people that are into every kink. Two weeks ago I was given the luxury of meeting some fembois and several trans individuals and had lunch. I've learned not to pass judgement on alternative lifestyles. Frankly, I've found anal to be an itch that I cannot scratch enough. Girlfriend had broke me in with pegging where I was climaxing every time. With a group the wives seem to love to watch as much as participate.

 

[mtsnowrider]

I connected with a guy on Silverdaddies once. We planned on meeting early morning before work. I drove to his house and rang the bell. When he opened the door, I was mortified to see a fellow teacher in knew. After an awkward pause, he asked what I wanted to do. I overcame my embarrassment and went in and fucked him anyway. It was actually pretty hot, fucking a man I knew. Neither of us ever said a word about it afterwards. But from then on, I always insist on seeing a face pic before I meet someone I connect with online.

I would think that was a win-win once you both got past the initial awkwardness. The start of a regular friendship

 

[mtsnowrider]

It could have been if he hadn't been such an asshole (personality-wise). His actual asshole was tight and oh-so-good, but I had no desire to meet up with him again. Maybe I shouldn't have fucked him, should have just left and had blue balls. But I was so fucking horny and badly needed to shoot a load. We hardly said a word. No sucking at all. He just dropped his shorts, bent over his bed, and I shoved my cock in and thrust for a while. It didn't take me long.

Too bad. Could have been a story with a "happy ending"

 

[2tallpaul]

The look on my face meeting two other Sissys like myself and not sure what was going on. I was told to check out the bits and pieces and I did it in front of others. One was missing parts, shaft was there but the rest gone. I guess the shock on my face was enough for some laughter. I slept with one eye open after that.

 

[BiMale4KinkyFun]

I was dating a girl, who did not know I was bi. She walked in on me and her father as he was covering my face with his cum.

 

[BizTrav]

C'mon y'all, Don't be shy... What's your most embarrassing sex-related story?!

A hotel housekeeper walked in as I was sucking a guys cock. Him on the bed and I was on all fours with a butt plug in. I never noticed but he told me after she came in that she looked straight into his eyes, down at my business spread directly in here line of sight, and quietly slipped back out. I stayed there for 2 more nights. She just smirked every time I passed her in the hallway.

Ummm...won't get into the details...involved being plugged, all of the sudden feeling very hot back there, and making one hell of a mess when the plug came out!

 

[cubbyfire04]

Ummm...won't get into the details...involved being plugged, all of the sudden feeling very hot back there, and making one hell of a mess when the plug came out!

Ah yes... It happens. Helps having a sense of humor about the situation

 

[BizTrav]

Ah yes... It happens. Helps having a sense of humor about the situation

Yeah...damn funny now, not so much at the time