Sharing Your Worst / Weirdest / Freakiest / Funniest Sexual Encounters (compiled)

[lovehandle]

6 hours ago, bigdanbeam said:

Lol. So the menstrual area is less yucky?

not that

 

but most will avoid having sex during that PMS period isn't it?

and there are plenty of feminine products that deal with such menstrual thing

Not matter what excrement will still appear yucky than urine and stuff
if I m being forced to drink urine or to eat faeces, I guess it will be the former! 

Most men (including me) will just walk off upon urinating at the urinals , shaking and keep shaking the penis doesn't remove/clean  up anything at all....

but females told me , they will wipe their vaginal upon urinating, pat dry etc, which is why they took hell long time in the loos

 

Men are very lazy (showed in those voyeur  video too), many don't even bother to wash their hands after urinating! this is a fact (seen by my own eyes and some r chefs working in the malls)  which is why u often see blue cheese and other cheesy materials on that part

the reason why I do slightly more waxing down there, is cos I felt cleaning my bottoms with toilet paper is not clean enough as it is too hairy, not cos I m preparing my route to become a btm.....I don't shave other areas

 

[devilry]

I don't know where to start. Being an older, larger guy I tend to attract ... less conventional lovers. I don't have many hang ups, so I have have more than my fair share of odd experiences.

 

I met someone once, for example, who was really turned on by touching me (my body and my junk) with his feet - and only his feet. He was also super turned on when I played with and manipulated his feet. We finished with me sucking on his toes while he jacked off and he shot a huge load. 

[Guest Open Door]

Was once invited by this random guy to his home for a blow. He left his front door unlocked, but the house was shrouded in darkness and he stayed well in the shadows. He guided me to the master bedroom, had me undress and began to greedily suck my dick. He used alot of Hokkien expletives and came across as very ah beng. Because he was rather rough and vigorous, it hurt alot and it wasn't fun for me. I just wanted to wash his saliva off my dick and leave ASAP. When I expressed my concerns to him, he was really apologetic. His demeanour suddenly improved, and he began speaking in a very educated voice. Before I left, he even slathered antiseptic cream all over my dick and offered me a multi-vitamin tablet with a fizzy Vitamin C drink to wash it down. The last 5 minutes felt that I had just paid a visit to my GP. Lol!    

[Guest CKW]

2 minutes ago, Guest Open Door said:

Was once invited by this random guy to his home for a blow. He left his front door unlocked, but the house was shrouded in darkness and he stayed well in the shadows. He guided me to the master bedroom, had me undress and began to greedily suck my dick. He used alot of Hokkien expletives and came across as very ah beng. Because he was rather rough and vigorous, it hurt alot and it wasn't fun for me. I just wanted to wash his saliva off my dick and leave ASAP. When I expressed my concerns to him, he was really apologetic. His demeanour suddenly improved, and he began speaking in a very educated voice. Before I left, he even slathered antiseptic cream all over my dick and offered me a multi-vitamin tablet with a fizzy Vitamin C drink to wash it down. The last 5 minutes felt that I had just paid a visit to my GP. Lol!    

 

Woah!!! That's real hot!! Thanks for sharing it!!!

 

He sounds like someone who might make a very good boyfriend  

 

Some gay guys who are very civil and gentlemanly have this fascination with ah beng characteristics, either in themselves or in their partners.

 

In fact, this has been documented before. Apparently, Leonardo Da Vinci was like that, if I remember correctly. He liked rugged boys because he considered himself too educated and refined.

[jurongwest]

Mine was quite unusual too... We meet up to have fun at my place... all going ok then he started making request like he feel like getting DP as he seen it in porn n suddenly feel like it...  but he don't want me to stop pounding him.., so he was sliding thru app finding another guy n letting me fuck him at same time... It just soooo weird...

 

all the sudden, he say he calling his buddy over.. I was shocked before I can react.. he is on the phone telling him he is getting fucj n need more cock n start giving my address...

 

i stop and ask him to leave... can't get hard anymore... 

[Guest Exit]

Another unlocked door encounter.

 

Our conversation had shifted from Grindr to Whatsapp. Less chance of being dropped by random pilots that way.

 

He gave me his address, but didn't answer the door when I arrived and knocked.

 

After waiting 20 minutes, he texted to say let yourself in and find me.

 

House was interesting, but seemed deserted.

 

Found a slightly hidden door, which led to a different section of the apartment.

 

Guy was blindfolded and tied up, and reacted really terrified when I found him.

 

Almost called the police, when he yelled in exasperation, "Oi! Never role-play before ah?!!"

 

Geez, I was soooo green in those days.

[cutejack]

17 hours ago, Guest Exit said:

Another unlocked door encounter.

 

Our conversation had shifted from Grindr to Whatsapp. Less chance of being dropped by random pilots that way.

 

He gave me his address, but didn't answer the door when I arrived and knocked.

 

After waiting 20 minutes, he texted to say let yourself in and find me.

 

House was interesting, but seemed deserted.

 

Found a slightly hidden door, which led to a different section of the apartment.

 

Guy was blindfolded and tied up, and reacted really terrified when I found him.

 

Almost called the police, when he yelled in exasperation, "Oi! Never role-play before ah?!!"

 

Geez, I was soooo green in those days.

Now yellow oredi ha?lol

[lovehandle]

On ‎16‎/‎1‎/‎2017 at 2:37 PM, Guest Exit said:

Another unlocked door encounter.

 

Our conversation had shifted from Grindr to Whatsapp. Less chance of being dropped by random pilots that way.

 

He gave me his address, but didn't answer the door when I arrived and knocked.

 

After waiting 20 minutes, he texted to say let yourself in and find me.

 

House was interesting, but seemed deserted.

 

Found a slightly hidden door, which led to a different section of the apartment.

 

Guy was blindfolded and tied up, and reacted really terrified when I found him.

 

Almost called the police, when he yelled in exasperation, "Oi! Never role-play before ah?!!"

 

Geez, I was soooo green in those days.

okie

this is hilarious!

[devilry]

On 16/01/2017 at 2:37 PM, Guest Exit said:

Another unlocked door encounter.

 

Our conversation had shifted from Grindr to Whatsapp. Less chance of being dropped by random pilots that way.

 

He gave me his address, but didn't answer the door when I arrived and knocked.

 

After waiting 20 minutes, he texted to say let yourself in and find me.

 

House was interesting, but seemed deserted.

 

Found a slightly hidden door, which led to a different section of the apartment.

 

Guy was blindfolded and tied up, and reacted really terrified when I found him.

 

Almost called the police, when he yelled in exasperation, "Oi! Never role-play before ah?!!"

 

Geez, I was soooo green in those days.

 

And did you proceed?

[mLy_dxkie]

On 1/13/2017 at 11:48 PM, wantonmee said:

Was trying on some new handcuffs and in the midst of the action, we couldn't find the small key after we were done...

 

He ripped the sheets, turned the bed, while I patted around the floor while still handcuffed...  

 

And finally found it stuck to his backside .... 

 

Lmao... 

 

Sounds pretty hot. The cuffs especially. 

[yuquidam]

On Friday, January 13, 2017 at 10:48 PM, wantonmee said:

Was trying on some new handcuffs and in the midst of the action, we couldn't find the small key after we were done...

 

He ripped the sheets, turned the bed, while I patted around the floor while still handcuffed...  

 

And finally found it stuck to his backside .... 

 

Lmao... 

HAHAHAHA....Heeeeelarious!. Good thing it didn't slip into his asshole or smthg...hahaha ....oooops SORI

Edited January 27, 2017 by yuquidam

[Guest GUEST]

Juz curious do u guys whisper/tell to your partner tat u r cumming when making love or juz shoot it out without telling them?  Few guys I make love with will normal tell me they r cumming before shooting out but there r some who did not n juz shot it. 

[bigdanbeam]

1 hour ago, Guest GUEST said:

Juz curious do u guys whisper/tell to your partner tat u r cumming when making love or juz shoot it out without telling them?  Few guys I make love with will normal tell me they r cumming before shooting out but there r some who did not n juz shot it. 

 

Usually Japanese will verbally inform you. The rest, just observe their body language to know

[cutejack]

2 hours ago, bigdanbeam said:

 

Usually Japanese will verbally inform you. The rest, just observe their body language to know

How abt u bdb

[Guest Guest]

I came across 1 that shouted "I m coming,  I m coming......arh...arh...arh.." 

[devilry]

I seem to wind up with guys who have special requests - so they usually announce. 

[devilry]

the usual - want me to swallow, or want to shoot on face or chest or whatever 

[Fit4Masc]

Me met this guy in a bar and back to my hotel.   He wanted me to give him a strangle hold around his neck!  I oblige, he kept saying harder, harder.  I was so afraid that I might choke him to death!  He seem be only be able to cum when he is near blackout!!!

[bigdanbeam]

23 minutes ago, Fit4Masc said:

Me met this guy in a bar and back to my hotel.   He wanted me to give him a strangle hold around his neck!  I oblige, he kept saying harder, harder.  I was so afraid that I might choke him to death!  He seem be only be able to cum when he is near blackout!!!

 

Tread with care. We hv heard of deaths resulting from such high risk play

[cutejack]

12 hours ago, bigdanbeam said:

 

Tread with care. We hv heard of deaths resulting from such high risk play

Ya la.somemore not his hotel room.Anything happen cant run

away

Lol

 

[Guest Guest]

Fuck a guy and was about to come and took out my condom and cum in his stomach

 

he then ask me to insert an ice cube into his ass

 

i reluctant thinking its a joke but he insisted so I stuff in an ice cube from the drink and he was cum so strong after that hahahaha at least 4-5 long streaks of cum on his chest and one up his neck

 

 

 

[CKW]

1 hour ago, Guest Guest said:

he then ask me to insert an ice cube into his ass

 

so I stuff in an ice cube from the drink and he was cum so strong after that hahahaha at least 4-5 long streaks of cum on his chest and one up his neck

 

Ouch!!! LOL!!!

 

It's very painful to put an ice cube in there as you will get a cold burn and a throbbing and numbing sensation after that.

 

Unless your man is this guy who can melt it immediately inside his body  

 

[lw_guy]

Once met a guy at a hourly hotel, he was so secretive and didn't want to appear at the counter so I have to book the room alone.

After that he came knockin on the door and it was a totally different guy from the pics he shown! Had a quick one and he left first..

[cutejack]

41 minutes ago, lw_guy said:

Once met a guy at a hourly hotel, he was so secretive and didn't want to appear at the counter so I have to book the room alone.

After that he came knockin on the door and it was a totally different guy from the pics he shown! Had a quick one and he left first..

Want shiok shiok with a guy but secretive la.discreet la.no balls at all.somemore sent different pic.haiz...y never throw stones at him.hahaha

[lw_guy]

37 minutes ago, cutejack said:

Want shiok shiok with a guy but secretive la.discreet la.no balls at all.somemore sent different pic.haiz...y never throw stones at him.hahaha

ya, alot of guys very paranoid with checking in to hotel... It was too shocking at tat time to react hahaa

[CKW]

1 hour ago, lw_guy said:

Once met a guy at a hourly hotel, he was so secretive and didn't want to appear at the counter so I have to book the room alone.

 

Actually, most hotel staff are very professional about the preferences of their guests and won't act weird if they see two guys checking into a room.

 

One time, I stayed at a hotel for a short staycation. For security reasons, the receptionist asked if I was expecting my girlfriend to visit me. I said no.

 

She replied, "A boyfriend, then?" in the same manner as she would ask if I had wanted breakfast in the room  

[cutejack]

1 hour ago, CKW said:

 

Actually, most hotel staff are very professional about the preferences of their guests and won't act weird if they see two guys checking into a room.

 

One time, I stayed at a hotel for a short staycation. For security reasons, the receptionist asked if I was expecting my girlfriend to visit me. I said no.

 

She replied, "A boyfriend, then?" in the same manner as she would ask if I had wanted breakfast in the room  

Wat was yr answer?yes or no?lol

[CKW]

4 minutes ago, cutejack said:

Wat was yr answer?yes or no?lol

 

No.  Lol

I was single then; am still single now  

[Guest Biz Travel]

10 hours ago, bigdanbeam said:

 

I think guest is secretly enjoying it lor. Then make it seem like it's the boy's fault. Full grown adult cannot stop a boy from swallowing? My hamster also dun believe

 

Yeah I know it's not weird to some people. But for me, I could only swallow if that's my boyfriend.

It's BJ and direct shot to the mouth, and he would swallow immediately. I can't even see a trace of my own cum. I'm in a dilemma whether to let him enjoy swallowing, or let myself enjoy it. lol.

 

4 hours ago, cutejack said:

Side track.abit.which hamster?

But frankly u cant control suckers

They can hold u tight n swallow

 

That's what I mean. And I do not want to push him away by brutal force. 

[devilry]

Not weird or freaky - just recent.

 

Saturday afternoon is a good time for sex.

Had a bit of fun with a Malay FB of mine - sucked his hefty cut cock and low-hanging balls before rimming him out. Rimmed him till his rod was hard and dripping, and then he put on a condom and fucked me hard.

A good rough sweaty fuck is just what I needed, and after he pumped all my tension away, he let me take my turn ploughing his ass - he shot his load lying on his back while I twisted his nipples, and then I pulled out, snapped off my rubber and jacked myself while he teased my tits till my load joined his all over his stomach.

Fun.

 

 

 

https://devilrysg.tumblr.com/post/156839413554/flip

[Leanmeat]

On ‎3‎/‎2‎/‎2017 at 1:39 AM, bigdanbeam said:

 

I think guest is secretly enjoying it lor. Then make it seem like it's the boy's fault. Full grown adult cannot stop a boy from swallowing? My hamster also dun believe

 

Yah lor, which guy getting suck dun like to cum in sucker's mouth and seeing him swallow?

[cutejack]

On Sunday, January 15, 2017 at 7:27 AM, Guest GGg said:

 

I had similar encounter too. if I remembered correctly, his house was in Sengkang beside a school.

I think i ķnow who.he is in the apps.lol

[Guest ah_boy]

On 01/02/2017 at 7:58 AM, Guest Guest said:

Fuck a guy and was about to come and took out my condom and cum in his stomach

 

he then ask me to insert an ice cube into his ass

 

i reluctant thinking its a joke but he insisted so I stuff in an ice cube from the drink and he was cum so strong after that hahahaha at least 4-5 long streaks of cum on his chest and one up his neck

 

 

 

 

Omg this is the same thing that the guy I met in grndr had asked me to do.

[Fit4Masc]

On 4/19/2018 at 7:29 AM, Guest ah_boy said:

 

Omg this is the same thing that the guy I met in grndr had asked me to do.

You sure you guys didn't hooked up with the same guy

 

[auscent]

A caucasian i hooked up in Taipei garden later was into me spanking him with a ping pong bat. Insisted dirty talk how Singapore whip bad boys in jail.

[kimlo777]

Many years ago, i hooked up with a Korean pastor.  On one occasion, he was sniffing a piece of paper as I sucked his cock.  when he was about to cum, he pulled his cock out from my mouth and shot his sperm on the piece of paper.  when i asked him about the paper, he showed me.  he explained that his wife has sent him that piece of paper with her pubic hair glued to it and the paper was smeared with her cunt juice.  he added his sperm and told me once it is dried, he will be sending it back to his wife.  they have been doing such stuff over the few months that i was servicing him.  in those days there was no skype, wechat or line for them to send photos or videos of each other.

 

several weeks later, when i was sucking his cock, he took out a pair of used unwashed panties which his wife sent him.  there was some blood stain on it - apparently her menstrual discharge.

 

imagine he was a church pastor - a really kinky one!

Edited May 14, 2018 by kimlo777

[Fit4Masc]

1 hour ago, kimlo777 said:

Many years ago, i hooked up with a Korean pastor.  On one occasion, he was sniffing a piece of paper as I sucked his cock.  when he was about to cum, he pulled his cock out from my mouth and shot his sperm on the piece of paper.  when i asked him about the paper, he showed me.  he explained that his wife has sent him that piece of paper with her pubic hair glued to it and the paper was smeared with her cunt juice.  he added his sperm and told me once it is dried, he will be sending it back to his wife.  they have been doing such stuff over the few months that i was servicing him.  in those days there was no skype, wechat or line for them to send photos or videos of each other.

 

several weeks later, when i was sucking his cock, he took out a pair of used unwashed panties which his wife sent him.  there was some blood stain on it - apparently her menstrual discharge.

 

imagine he was a church pastor - a really kinky one!

Yeah, I read a research paper about those extreme religious sorts.  It's now proven that they all suffer from some sort of mental illness, something to do with their prefrontal cortex development/damage and are known to be hypocrites.  Google it, http://bigthink.com/paul-ratner/study-finds-link-between-brain-damage-and-religious-fundamentalism its a very interesting read.  The most dangerous type of crazies are those who don't know they are crazies!

Edited May 14, 2018 by Fit4Masc

[Guest SpinOff Story]

7 hours ago, kimlo777 said:

Many years ago, i hooked up with a Korean pastor.  On one occasion, he was sniffing a piece of paper as I sucked his cock.  when he was about to cum, he pulled his cock out from my mouth and shot his sperm on the piece of paper.  when i asked him about the paper, he showed me.  he explained that his wife has sent him that piece of paper with her pubic hair glued to it and the paper was smeared with her cunt juice.  he added his sperm and told me once it is dried, he will be sending it back to his wife.  they have been doing such stuff over the few months that i was servicing him.  in those days there was no skype, wechat or line for them to send photos or videos of each other.

 

several weeks later, when i was sucking his cock, he took out a pair of used unwashed panties which his wife sent him.  there was some blood stain on it - apparently her menstrual discharge.

 

imagine he was a church pastor - a really kinky one!

Few more weeks later after that several weeks later, when you were sucking his cock, he took out a baseball bat and start sniffing and licking ..... you knew whar was happening 

[MasterDaddy]

Worst, weirdest, freakiest, funniest sexual encounters? Daddy has experienced all. Weird and freaky usually involved sexual practices that were new to Daddy but considered quite normal by the other guys involved. The things that some guys get up to and want daddy to do with them never ceases to amaze. The first time Daddy was asked to fist a guy for example. Fingering a guys ass is one thing. Burying your arm in a guys ass up to your elbow, now that was weird. The first time Daddy was asked to dominate a guy was also freaky. In Washington DC Daddy met a black guy who was pure body builder muscle and well over 6 feet 6 inches tall. He wanted daddy to slap, punch, spit on him, call him derogatory racial names etc. Daddy obliged. Very freaky especially as the guy could have killed Daddy with one punch. Still he must have enjoyed it because we met a few more times after that. Guys into feet also can be a bit freaky. There are so many guys who just want to play with feet. The first time it was a bit weird to have a guy kissing and licking Daddy's shoes, stocking feet and sucking daddy's toes. The problem with feet and fisting though is the other guys gets all the sexual satisfaction. These guys are not usually interested in cock. Similarly the first experiences of using bondage, blindfolds and gags on guys was a bit weird but hey, one gets use to it. The boy who liked Daddy to stick his cock into a carton of yoghurt so he could then  lick it clean could also be considered a bit freaky.  The boy who wanted to be treated like a puppy and collared and put on  chain and eat out of a dog bowl also caused Daddy some initial concern. Funniest are too many to mention but there was the time in South America where a guy came to daddy's hotel room but Daddy was taking an important business call. The boy didn't say a word but simply stripped, took out Daddy's cock, sucked it and then backed his ass onto Daddy's cock and started pumping it into his ass as Daddy stood taking the phone call. Very hard to concentrate on a business conversation under such an assault. Then there was the guy in UAE that daddy arranged to meet on line. There was knock on the door and when Daddy opened it there stood a guy without any arms. Now how do you forget to mention that when arranging a date! Maybe he thought Daddy wouldn't notice. Daddy still doesn't know how he managed to knock on the door lol. Worst encounters usually involve guys who use magic cameras. The sort of cameras that when they take your picture produce a picture of a totally different looking guy. If you use fake pictures and then meet the guy you sent them to don't you think the difference will become apparent? Being tricked into a meet is always the worst experience.

[Guest Woah]

I've only met one young chinese guy who was not very tall (170cm+) with a huge dick it looks alien compared to his skinny frame, almost 7inch+ and it was thick with full mushroom head. He had to hold on to his hard dick when walking as it kept flopping around making him lose balance between his legs. It was hilarious but he did shoot a big load of cum as he didn't JO for a week while in BMT. 

 

Anyone have funny situations to share?

[Gobal100]

Is it lol. 

[Guest guest]

3 hours ago, Guest Woah said:

I've only met one young chinese guy who was not very tall (170cm+) with a huge dick it looks alien compared to his skinny frame, almost 7inch+ and it was thick with full mushroom head. He had to hold on to his hard dick when walking as it kept flopping around making him lose balance between his legs. It was hilarious but he did shoot a big load of cum as he didn't JO for a week while in BMT. 

 

Anyone have funny situations to share?

 

You were dating him? How you managed to see him cum?

[cutejack]

13 hours ago, Gobal100 said:

Is it lol. 

Should be wow

[kimlo777]

One hilarious situation I was caught in was some years back in the very quiet toilet at the old Straits Trading Building, Battery Road.  I picked up a guy at the infamous OUB basement toilet and we headed to Straits.  In the 3rd floor toilet we stood by the urinal and I was stroking his very handsome looking 6-inch dick when we heard the creak of the toilet door.  I immediately let go of his cock and at that moment when the male cleaner walked in, I heard him saying out loud, 'shit' and then his cock began twitching and his sperm spurted all over the floor.  He was so stunned that he forgot to moved to facing the wall, instead he was facing the direction of the cleaner who stood still frozen in surprise.  It was rather awkward for everyone.  He was practically blushing and perspiration was pouring down his forehead not knowing what to do.  He just stood there staring at the cleaner who was staring at him in return.  Imagine him standing there like a statue, pants and briefs down to his ankles and his erect cock sticking out from his bushy pubes with a long string of cum hanging halfway to the floor.  The cleaner looked at him and me and then remarked, "next time do it in the stall and don't mess up the floor for me to clean up" and then he walked out shaking his head.  After that we both burst out laughing and I knelt down to continue sucking him until he blew another load, this time down my throat.  And as if in perfect timing, when he was shooting his spunk in my mouth that same cleaner had to walk in once again and shouted at us, "enough already, I want to clean the toilet."  So he dressed up and we left together not before I turned round and gave the cleaner a wink of my eye.  Btw, the cleaner was a Malay hunk in his late 30s and looked as if he wanted a piece of the action as well.  But that is another story.

[Guest Woah]

17 hours ago, Guest guest said:

 

You were dating him? How you managed to see him cum?

It was a hookup.

[Guest Harley]

What was your most unusual sexual experience?

[LoneRanger]

Only had one bizzare exp. It was a year ago, I met this guy from grindr and we agreed for ONS. Long story short,  he told me he can only cum if I lick his ears. Yes, you heard it right. His ears. 

[Guest Elaborate]

12 hours ago, LoneRanger said:

Only had one bizzare exp. It was a year ago, I met this guy from grindr and we agreed for ONS. Long story short,  he told me he can only cum if I lick his ears. Yes, you heard it right. His ears. 

Did you manage to lick his ear until he cummed? 

[icydestruct]

15 hours ago, LoneRanger said:

Only had one bizzare exp. It was a year ago, I met this guy from grindr and we agreed for ONS. Long story short,  he told me he can only cum if I lick his ears. Yes, you heard it right. His ears. 

From my experiences it's not that uncommon apparently. While I personally do not understand, they found it sensual when their ears were licked. But not to the extent that they can only cum from their ears licked of course 

[Guest Uncle]

On 5/8/2020 at 10:39 AM, Guest Elaborate said:

Did you manage to lick his ear until he cummed? 

My most crazy experience? I went to this Malay guy in woodlands for fun. When I entered his place, his kids were cute and running around. He said don't worry. So we proceeded to his room. His wedding pictures were looking at us while he suck my hairy cock and lick my furry asshole, so uncomfortable. Halfway, he said his wife should be on the way home soon. I freaked out!!! That's not the crazy thing yet. The kids were just playing happily outside his room, and occasionally knocking on the door to ask daddy what are you doing, so much noise inside, are you OK? So cute! Then he said the craziest thing: can you fuck my wife and I? We take turns? We suck your cock together? You cum on our faces? Guess what? His wife reached home and I heard her outside talking to kids. I freaked out. Dressed up and left. Bizzare?