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

[TT2880]

He and I found one another in a chat room. Then we arranged to meet-up. When we met, the feeling was right. We chatted the entire night. Ever since, we have never ending best committed sexual experience. It sure is unusual, especially amongst gays where monogamy is literally a bad word.

 

[aelwaien]

57 minutes ago, TT2880 said:

He and I found one another in a chat room. Then we arranged to meet-up. When we met, the feeling was right. We chatted the entire night. Ever since, we have never ending best committed sexual experience. It sure is unusual, especially amongst gays where monogamy is literally a bad word.

 

Aren't you a lucky one? 😁

[tyan]

Met up with this guy who claimed that he can give the best blowjob on condition that I give him my cum. Thinking should be ok since he want to swallow. Met up with him at the park. He proceed to suck. Apparently he is an amateur. It is one worst blowjob I ever had. I didn’t cum. Then he asked me to jerk off becos I promise to give him his cum. Sigh. Fine. I jerk off in front of him. Just before I was about to cum. He passed me a jar and asked me to cum inside. He want keep it.

i was like huh !!!!

[Guest guest]

beware!

he could be using your sperm to impregnate his wife.  .. or worse, a woman to later sell off the baby.

[mate69]

or worst. to set u up in the most capricious way

[Guest Uncle]

8 hours ago, Guest guest said:

beware!

he could be using your sperm to impregnate his wife.  .. or worse, a woman to later sell off the baby.

How long can sperm stay alive in outside environment?

[TT2880]

11 hours ago, aelwaien said:

Aren't you a lucky one? 😁

Hi,

 

Thank you. 

 

If we see relationship as merely a stroke of luck than that luck will definitely ceased. On the other hand, when we sees relationships with a right perception, it will lead to right decisions and right action. We will find ourselves lucky no matter how our relationship with others changes. 

 

Thank you once more for your kind words. 

 

 

[tyan]

4 hours ago, Guest Uncle said:

How long can sperm stay alive in outside environment?

Precisely!! Haha. Sperm cannot stay alive so long. He says he is going to put in the fridge and slowly drink. This really freak me out. 

[Guest guest]

when I cum on my pubic hair the sperm will form white lumps dying together. quite unnecessary to do sperm count for reproduction consultation a waste of money.

sperm remain alive for some time if collected together with the seminal fluid in small containers.

when sperm manage to be inside a vagina it can live even longer although the acidity is meant to kill most of the sperm leaving the strongest few to impregnate.

[strategicthrust]

I still recall this encounter i had with a fresher back in uni. We'd met over grindr, and after chatting for a while he invited me over to his room to stay the night (it was already close to midnight at that point). I didn't have much planned for the next day, so i agreed.

 

When i got there, we chatted for a while about our uni life, past relationships etc.. he told me he was bi, and had been in a rls with another guy but never had sex before. After some time he suggested we go to sleep cos he had an exam the next day. We snuggled for a bit, then he seemed to drift off to sleep so i shut my eyes too. After some time, i couldnt really sleep yet so i opened my eyes again. I saw him staring right at me (we were facing each other), but when he saw me open my eyes he quickly shut his. At that point, i was feeling pretty horny and was a bit disappointed he'd said he only wanted to chat.. so i decided to try my luck.

 

I was alr hugging him, so i slowly moved my hand down to his crotch, and let it rest there. He brushed it away and hugged me back. Something felt a bit off about his behaviour, so i tried again. Again got brushed away. This happened a few more times, and sometimes he would give a 撒娇 kind of 'dont want' noise. I decided to try a different tactic. I took his index finger in my hand and started stroking it up and down, and tickling it gently, basically treating it like i would play with his dick. But he didnt respond at all and continued sleeping.

 

At that point i thought 'ok maybe he really doesnt want' so i just stopped and just spooned him, preparing to sleep. At that moment, as i hugged him, i realised his heart was pounding away like mad. Aha, i thought. He's pretending to sleep but he's so excited?? Hmmm.

 

I slowly inched my hand downwards again. Again, he pushed my hand away as if to brush me off, but this time, his hand pushed mine onto his crotch. Aha! I knew it! As i slid my hand into his shorts, he flipped over, lying on his front, which meant my entire arm got kiapped between his crotch and the bed. I was kinda surprised, but i continued wiggling my fingers into his underwear.

 

When i touched his dick, lo and behold.. it was soft, but the head was completely soaked in precum. Lol this guy, i thought to myself. I started massaging his dick with one finger (i couldnt move my hand as it was pinned under his body weight), and with my other hand i started tickling his nipples. I felt him harden. He still had his eyes closed, pretending to sleep. After a while of this, i tried flipping him over, and only managed to get him on his side. That was enough for me. I pulled down his shorts, and sucked his dick into my mouth. I was in a pretty awkward position with my head against the bed so that i could keep sucking him.

 

This was a tiring position so i flipped him back onto his back. He wasnt particularly cooperative so i had to kinda shove him a bit to get him into that position. His dick was pretty average in length, but with a nicely-shaped head that was pretty enjoyable to suck. After working on him for a while, i got a bit tired so i switched to jerking him off for a while. After just a couple of strokes, i suddenly felt a blast of cum hit my face! I was so surprised by the sudden cumshot i reflexively jerked his dick away, and the second blast landed on his face, then all over him and his bed after that.

 

He "woke up" shortly after and asked "what did you do?" I grinned and said "i didn't do anything~" it was such a funny sight, this cute boy mumbling some complaints about having an exam later, with his shorts around his legs and a glob of his own cum trickling down his face. I felt bad about the exam so i helped him remove his bedsheets and tidy up a bit. I wonder if he flunked because of me ahahah

 

I still remember this vividly though it's been a few years since it happened. The one and only time i made a guy cum in his "sleep".. hehe.

Edited June 7, 2020 by strategicthrust

[Guest Guest]

On 5/17/2018 at 9:52 AM, kimlo777 said:

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.

 

Tell us more.

[kimlo777]

On 6/9/2020 at 3:37 AM, Guest Guest said:

 

Tell us more.

A couple of weeks passed and I had a return visit to Straits Trading Building and sure enough bumped into that same Malay toilet cleaner.  We spoke and arranged to meet up that night after he finished his shift.  We met at Raffles Place and he suggested going back to his rented room which he shared with a few friends, assuring me that they were all at work in the evening.  As soon as we got into his room in Beach Road, he started stripping, wore a sarong and said he was going for a shower.  I waited for him in his room.  Scanning around I saw some photographs on the dresser and realised that his room-mates (5 altogether) were all equally hunky and gorgeous looking.  Later I learnt from him that they were all from Johor working in Singapore.

 

When he came back to the room, he started to hug me and we kissed deeply.  He was an extremely good kisser and soon I felt something hard poking into my abdomen.  My hand reached in between us to fondle his erection which felt really hard and enormous.  He then led me to the mattress on the floor and lay me down.  He let his sarong drop to his ankles and my attention was immediately drawn to his cock which stood out at 45% from his completely shaven groin.  I estimated it to be at least 8 inches long, very thick and veiny.  Below hung a large low-hanging scrotal sac which were also hairless.  He sat astride my chest and aimed his cock at my face.  Without hesitation, I held his cock and placed it right at my lips.  My tongue darted out and lick his pee-hole and he shuddered giving out a soft moan.  '"Shiok," he said softly as he started pushing his thick cock deeper into my mouth.  I gagged slightly due to the enormity of his organ but he was relentless.  He started pumping his cock in and out of my mouth, fucking my mouth.  Soon I too got into the rhythm and was enjoying having his cock rape my mouth.  Unfortunately he didn't last very long.  After about 3 or 4 minutes of fucking my mouth, his whole body began to tremble and his breathing became heavy.  He gave out a loud groan, drove his massive organ down my throat and screamed, "urrgggggggggggggggghhhhhhhhhh, urrrrrgggggggggggghhhhhhhhhh ..." and let out spurts after spurts of thick creamy cum down my throat. 

 

We met up several times more at his rented room.  After a few months, he said his room-mates got to know about me and wanted a piece of action too.  But that's another story.

 

[cutejack]

2 hours ago, kimlo777 said:

A couple of weeks passed and I had a return visit to Straits Trading Building and sure enough bumped into that same Malay toilet cleaner.  We spoke and arranged to meet up that night after he finished his shift.  We met at Raffles Place and he suggested going back to his rented room which he shared with a few friends, assuring me that they were all at work in the evening.  As soon as we got into his room in Beach Road, he started stripping, wore a sarong and said he was going for a shower.  I waited for him in his room.  Scanning around I saw some photographs on the dresser and realised that his room-mates (5 altogether) were all equally hunky and gorgeous looking.  Later I learnt from him that they were all from Johor working in Singapore.

 

When he came back to the room, he started to hug me and we kissed deeply.  He was an extremely good kisser and soon I felt something hard poking into my abdomen.  My hand reached in between us to fondle his erection which felt really hard and enormous.  He then led me to the mattress on the floor and lay me down.  He let his sarong drop to his ankles and my attention was immediately drawn to his cock which stood out at 45% from his completely shaven groin.  I estimated it to be at least 8 inches long, very thick and veiny.  Below hung a large low-hanging scrotal sac which were also hairless.  He sat astride my chest and aimed his cock at my face.  Without hesitation, I held his cock and placed it right at my lips.  My tongue darted out and lick his pee-hole and he shuddered giving out a soft moan.  '"Shiok," he said softly as he started pushing his thick cock deeper into my mouth.  I gagged slightly due to the enormity of his organ but he was relentless.  He started pumping his cock in and out of my mouth, fucking my mouth.  Soon I too got into the rhythm and was enjoying having his cock rape my mouth.  Unfortunately he didn't last very long.  After about 3 or 4 minutes of fucking my mouth, his whole body began to tremble and his breathing became heavy.  He gave out a loud groan, drove his massive organ down my throat and screamed, "urrgggggggggggggggghhhhhhhhhh, urrrrrgggggggggggghhhhhhhhhh ..." and let out spurts after spurts of thick creamy cum down my throat. 

 

We met up several times more at his rented room.  After a few months, he said his room-mates got to know about me and wanted a piece of action too.  But that's another story.

 

A piece or many pieces of actions ? Tell us soon. Thx

[Guest Oh my]

Wow you must be an exceptionally attractive old aunty for the hunk to be so turned on. 

[barney1977]

I had a weird one, which happened about 6 years ago. Hooked up on Grindr or Scruff (forgot which one) with this big-shot corporate lawyer from London on a business trip. Neither good looking nor ugly, average married-men kinda look and average build with a cute little tummy. I think he's either Indian or Pakistani.  

 

I went up to his hotel room and he offered me a bottle of mineral water, had some small talks and insisted that I finish the bottle of water. Didn't really think much about it then. I finished the water and then started getting physical. 

 

Once we got naked, he asked if I'm OK to accommodate to his fetish. I was thinking he looked harmless and well, there's a first for everything and I said why not. Then he took out an adult diaper from his luggage and proceed to put it on. I was like - huh!?!? 😳 I was curious on what will happen next and played along with him. 

 

We proceeded to foreplay, mainly hugging, carressing and him licking and sucking my nipples and dick. I was all hard and horny and then he asked me to pee inside his diaper 😳😳😳. That was why he insisted I finish drinking the bottle of water!

 

Took me a few tries as it was hard to pee with a hardon 😅. The position was awkward as well having to slide my dick inside the diaper waistband. Initially some of my pee landed on the hotel floor carpet. We moved to the bathroom and tried a few positions to have me pee inside his diaper. Eventually managed to and he was moaning really loud while I was peeing into his diaper. I think he may have orgasmed while I was peeing... 

 

After that, he led me to bed with me lying on my back and he sucked me until I came. Did some small talks about his work after that while I was dressing up to leave. Didn't dare ask him on the diaper fetish 😅. We had a friendly hug before I left.

 

He came to SG again a couple of months later and contacted me. Unfortunately I was on a business trip overseas then. Not sure if I would meet him a second time then. Anyway, never contacted me again since. 

 

[kimlo777]

4 hours ago, Guest Oh my said:

Wow you must be an exceptionally attractive old aunty for the hunk to be so turned on. 

i am far from attractive.  for many str8 or bi guys, looks don't really matter. what they need is a hole to pluck their pole, that's all.  it's not like we are getting into a relationship. it's just plain sex so any hole will do.

[Zealouslogue]

On 6/19/2020 at 3:58 PM, barney1977 said:

I had a weird one, which happened about 6 years ago. Hooked up on Grindr or Scruff (forgot which one) with this big-shot corporate lawyer from London on a business trip. Neither good looking nor ugly, average married-men kinda look and average build with a cute little tummy. I think he's either Indian or Pakistani.  

 

I went up to his hotel room and he offered me a bottle of mineral water, had some small talks and insisted that I finish the bottle of water. Didn't really think much about it then. I finished the water and then started getting physical. 

 

Once we got naked, he asked if I'm OK to accommodate to his fetish. I was thinking he looked harmless and well, there's a first for everything and I said why not. Then he took out an adult diaper from his luggage and proceed to put it on. I was like - huh!?!? 😳 I was curious on what will happen next and played along with him. 

 

We proceeded to foreplay, mainly hugging, carressing and him licking and sucking my nipples and dick. I was all hard and horny and then he asked me to pee inside his diaper 😳😳😳. That was why he insisted I finish drinking the bottle of water!

 

Took me a few tries as it was hard to pee with a hardon 😅. The position was awkward as well having to slide my dick inside the diaper waistband. Initially some of my pee landed on the hotel floor carpet. We moved to the bathroom and tried a few positions to have me pee inside his diaper. Eventually managed to and he was moaning really loud while I was peeing into his diaper. I think he may have orgasmed while I was peeing... 

 

After that, he led me to bed with me lying on my back and he sucked me until I came. Did some small talks about his work after that while I was dressing up to leave. Didn't dare ask him on the diaper fetish 😅. We had a friendly hug before I left.

 

He came to SG again a couple of months later and contacted me. Unfortunately I was on a business trip overseas then. Not sure if I would meet him a second time then. Anyway, never contacted me again since. 

 

Oooooh, really kinky. 

[Guest Sam]

This happen during the 90s when I was young so much younger than today. There is this guy in Kallang who was a nurse. Whenever we had encounter in his bedroom, he'll ask me to wear medical gown. Sometimes he strips me, sometimes he'll fuck me with it.

[auscent]

This guy I met overseas. He was mild until I told him Im from Singapore. He lit up, said oh theres where they have caning. Took out a ping pong bat to spank him.

[TEY2005]

On 6/19/2020 at 9:53 AM, kimlo777 said:

A couple of weeks passed and I had a return visit to Straits Trading Building and sure enough bumped into that same Malay toilet cleaner.  We spoke and arranged to meet up that night after he finished his shift.  We met at Raffles Place and he suggested going back to his rented room which he shared with a few friends, assuring me that they were all at work in the evening.  As soon as we got into his room in Beach Road, he started stripping, wore a sarong and said he was going for a shower.  I waited for him in his room.  Scanning around I saw some photographs on the dresser and realised that his room-mates (5 altogether) were all equally hunky and gorgeous looking.  Later I learnt from him that they were all from Johor working in Singapore.

 

When he came back to the room, he started to hug me and we kissed deeply.  He was an extremely good kisser and soon I felt something hard poking into my abdomen.  My hand reached in between us to fondle his erection which felt really hard and enormous.  He then led me to the mattress on the floor and lay me down.  He let his sarong drop to his ankles and my attention was immediately drawn to his cock which stood out at 45% from his completely shaven groin.  I estimated it to be at least 8 inches long, very thick and veiny.  Below hung a large low-hanging scrotal sac which were also hairless.  He sat astride my chest and aimed his cock at my face.  Without hesitation, I held his cock and placed it right at my lips.  My tongue darted out and lick his pee-hole and he shuddered giving out a soft moan.  '"Shiok," he said softly as he started pushing his thick cock deeper into my mouth.  I gagged slightly due to the enormity of his organ but he was relentless.  He started pumping his cock in and out of my mouth, fucking my mouth.  Soon I too got into the rhythm and was enjoying having his cock rape my mouth.  Unfortunately he didn't last very long.  After about 3 or 4 minutes of fucking my mouth, his whole body began to tremble and his breathing became heavy.  He gave out a loud groan, drove his massive organ down my throat and screamed, "urrgggggggggggggggghhhhhhhhhh, urrrrrgggggggggggghhhhhhhhhh ..." and let out spurts after spurts of thick creamy cum down my throat. 

 

We met up several times more at his rented room.  After a few months, he said his room-mates got to know about me and wanted a piece of action too.  But that's another story.

 

More more more!!!!