Your Worst Masturbation Story

[Sapphire]

We all do it, masturbating is fun, I could ask when you started, or maybe how you discovered how amazing it could feel to explore the parts 'down there', but I am pretty sure the stories would involve mostly humping the bed or using the shower head.

Instead, my Truth question for you is what was your worst Masturbating experience ever? Did you get caught by your parents? Did you injure yourself? Did your dog jump on you and potentially ruin one of the best orgasms in your entire life?

Bring on the amusement... or, erm, the stories!

[richied]

Oh GOD! lolol... Wednesday the 13th, three times in a row.. My father walked in on me.

[Sapphire]

Oh GOD! lolol... Wednesday the 13th, three times in a row.. My father walked in on me.


Wait, three times in a row? You... you kept going??

[cxb13]

We all do it, masturbating is fun, I could ask when you started, or maybe how you discovered how amazing it could feel to explore the parts 'down there', but I am pretty sure the stories would involve mostly humping the bed or using the shower head.

Instead, my Truth question for you is what was your worst Masturbating experience ever? Did you get caught by your parents? Did you injure yourself? Did your dog jump on you and potentially ruin one of the best orgasms in your entire life?

Bring on the amusement... or, erm, the stories!

My dad caught me. He went out shopping, so I was home alone. He said he was going to be gone at least a couple of hours. Anyway pretty much within five minutes of him going out, I got naked and started masterbating . I had left my clothes upstairs whilst I was downstairs. Anyway ten minutes later I was getting close to the edge of orgasm, when I hear the front door open! He'd forgotten his wallet! Due to the layout of my house, I couldn't hide anywhere. Needless to say he caught me naked, fully erect and in desperate need to cum. Humiliating. Luckily we never spoke of it again .

[SandMguy]

I was home alone so I was experimenting a little. I put some sponges in a cup with a lot of soap but unfortunately not enough water. It wasn't until I was about to cum that I realised I had rubbed the head nearly raw, it really hurt for it to touch anything, even water so stupidly I just stopped and left it for a while. I noticed a while later that the soap had dried and dehydrated my cock head, wringing it was excruciatingly painful but I knew I had to. Luckily I was home alone for a while because I couldn't bare to wear clothes for five days. I couldn't touch it so I masturbated anally for at least a week.

WARNING: Soap is very bad lube, I tried extra hot chilli powder and saliva the other day and that was more pleasant.

[Sapphire]

WARNING: Soap is very bad lube, I tried extra hot chilli porter and saliva the other day and that was more pleasant.

I will take your word for it, sheesh, sounds painful!

[Kinkdad]

Sharing a place with some housemates, I was going through a phase where I was subby/a bottom and I'd gotten a new dildo and some poppers, lying on my bed wanking furiously, high on poppers and with the dildo deep in my ass.

So close to cumming.

Aaaand the fire alarm goes off and I can hear my favourite housemate running down the corridor to see if I'm in and make sure I get out.

Dildo flies across the room, new bottle of poppers spilled on the carpet and I had blue balls and a sore ass for the rest of the day after jumping up and scrambling into some jeans.

[CherryGirl201]

I've never been able to orgasm. Ever.
Now y'all should just imagine that. And then cry a little for me.
Besides from that it's all very pleasant!

[Fetique]

I've never been able to orgasm. Ever.
Now y'all should just imagine that. And then cry a little for me.
Besides from that it's all very pleasant!

How? Have you just never gotten to the good part, are you denying yourself, or do you have some sort of disability? Never having had an orgasm is pretty weird if you're 18+ years old.

As for myself, mine is pretty mild. I'm incredibly cautious about things that might not look too good, so I never got caught. My worst experience was at 15 years old, I was masturbating through my pants, because I didn't really care to take them off, weren't planning to actually go over the edge until later.

Then all of a sudden, I accidentally go over, and I pinched close the end of my penis with two fingers (uncircumsised, I can do that) in an attempt to let out no cum. It had happened once before, and that was the solution, however this time I weren't as lucky, and had to sneak to the bathroom, get a spare pair of pants, and to avoid any suspicion at all from my parents, I threw out the soiled ones. So that's my worst.

[Jah Brother]

I got tons of these!
One that keeps reocurring is one of my favourites though.
You go out, get drunk, dance to music, watch girls dance to music, one hotter than the other one. You just get in the mood.

After going out, failing various attempts to get a girl home (jk, I never tried that. Or once, in Germany, but that's another tale) you just blast your own music while winding down from the night.
I love that part so much, to lay in bed and listen to reggae after all that party music.
You think of the girls you saw and you think..... why not?
At this point I start jerking.
And jerking, and jerking. Endlessly. After about half an hour I give up, finally I realised that alcohol is bad.
And the next morning I wake up with a dick covered in these little wounds caused by constant friction.
When will I ever learn?

[CherryGirl201]

How? Have you just never gotten to the good part, are you denying yourself, or do you have some sort of disability? Never having had an orgasm is pretty weird if you're 18+ years old.

As for myself, mine is pretty mild. I'm incredibly cautious about things that might not look too good, so I never got caught. My worst experience was at 15 years old, I was masturbating through my pants, because I didn't really care to take them off, weren't planning to actually go over the edge until later.

Then all of a sudden, I accidentally go over, and I pinched close the end of my penis with two fingers (uncircumsised, I can do that) in an attempt to let out no cum. It had happened once before, and that was the solution, however this time I weren't as lucky, and had to sneak to the bathroom, get a spare pair of pants, and to avoid any suspicion at all from my parents, I threw out the soiled ones. So that's my worst.
I do to know why! I just can't make myself cum! I haven't had too many sexual experiences with people other than myself, but for some reason I can't make it happen! It's so frustrating! It feels so good and it just can't make it get - there! I can never reach the peak, just slight pleasure the whole time.
But I've been working on it, and I've heard when you're denied your clit is extra sensitive. Lately my clit had been PRETTY sensitive so I'm hoping that that means my body is ready! I want my orgasm!

[Sapphire]

I do to know why! I just can't make myself cum! I haven't had too many sexual experiences with people other than myself, but for some reason I can't make it happen! It's so frustrating! It feels so good and it just can't make it get - there! I can never reach the peak, just slight pleasure the whole time.
But I've been working on it, and I've heard when you're denied your clit is extra sensitive. Lately my clit had been PRETTY sensitive so I'm hoping that that means my body is ready! I want my orgasm!

Oh my gosh, Darlin, we need to get you some relief. Buy a hitachi wand, or a butterfly vibe or a bullet- something!

I wasn't sure I had orgasmed in the first couple of years after I started, until I discovered the shower head, oh mah god.

Sheesh, I would die if I were you!

[richied]

Lol, not the same day.. it was different days..

[lolo15]

My worst masturbation is before my wedding. The person who would become my wife caught masturbating me just before our wedding. She was angry and she said that regret. To punish me for our wedding night, my wife put me a chastity cage. I bring this cage for 10 years now.

[johnny2100]

Nice one...my worst was when i was masturbating in my trousers, as i actually didn't want to cum.
Well i sat there and suddeenly the door opens and my girlfriend with one of her friends come home.I immediately let go from my cock but came in an instant. The both walked in like :"Hi, how're you doing" and my cock is pumping lots of cum in my underwaer and running down my legs, i completly lost control caught by surprise.
I just managed something like: "Hi, well i'm alright", then, not to obvious head of to the toilet, cleaning myself with the soiled boxers.
But i had to smuggle them through our home to the washingbasket. Our bath was tiny, no place to hide my drenched pants, so i put them in the pocket of my hoodie and stole away.

[HarryPotter]

One foggy morning on my paper route, I decided to strip naked in the middle of a field. I figured that no-one would be able to see me as I was hidden by fog.

Part ways through jerking off, a dog came sniffing round my feet soon to be followed by the dog's owner. There I was, stood butt naked with my cock in my hand.

She just looked at me with a disgusted expression and walked past

Never forgotten that

[DirtyBiSub]

When I was younger (think I was 12) I started doing some mild exhibitionism. The first time happened kinda randomly. I was going for a walk and suddenly, at a deserted place, I sat down on a bench, pulled down my pants and started masturbating. What I didn't realize was that the restaurant nearby was open. So, I started getting really into it and then I looked to the right and there were 3 women (workers, I assumed) who just stood there watching. I panicked and ran with the pants around my ankles. For a 12 year old boy it was very embarrassing!

[lolo15]

The day of my wedding, my future wife caught me masturbating. She got angry. She told me that I would regret it for long.
For our wedding night, my Wife forced me to put a chastity belt that I kept constantly.
To punish me even more, it made me gradually premature ejaculation. Now I regret my gesture.

[Teeks]

I would say that, without a doubt, my worst masturbation stories - or at least those I keep the worst memories of are all of failed masturbation attempts.

Often it was when I was going on vacation for the summer holiday with my parents - and would come a moment, during the stay, when I could masturbate all I wanted, as hard as I wanted, there was nothing to do, I wouldn't cum.
And I remember crying in frustration once, after days of trying and not cumming - once when I was 14, the other when I was 16.

[jana-sissy]

I was 17 yo I guess. I crossdressed myself as a slutty Sissy, took a roll of plastic wrap and duct tape with me and went out in public at night. I went to my School (which had some scaffold on it due to construction works). I climbed at the Roof of the School, wrapped several layers of tape around my mouth / head. then I wrapped up a pole on the Roof in plastic wrap. After using the complete roll of plastic wrap I grabbed the end of it, and slowly started to unwrap the pole while Spinning myself. This resulted in me getting wrapped up tighter and tighter. Once I was done I tipped over and was a helpless tied and gagged plastic Sissy Mummy. I then managed to jerk off, and after I came I had to struggle for half an hour to escape from my tight plastic cocoon. Once free I climbed down the scaffold and ran home, dressed as a Sissy, humiliated, cum all over me. I had to hide 2 times behind some cars cause a Group of Girls walked towards me in the dark streets. :O

[Secretfun]

I used to 'borrow' mom's dildo when I was alone and slide it in my ass while I wanked. One time she came home while I was listening to my Walkman and didn't hear her walk in. She saw everything. I didn't know she was there till she gave me a whack and ripped it out and walked off. We didn't speak for about a week...

[Ellie Benelli]

Well, with my first girlfriend, and mistress...she had me piss myself in a Walmart bathroom, and then rub myself through my panties until I came. As much as I enjoy feeling embarrassed, that was rough.

[Jah Brother]

Posting this because I got loads of stories, want to bump it because I love to read these and because I want a certain someone to post ;)

So I was around 15, had a dispute with my father and my PC broke because of it. I got to use my mom's laptop downstairs though. So Jah is sad, because Jah has no porn, for MONTHS untill I saved up for a new pc. And doing it without any visual/reading simulation it takes way too long to enjoy it. Then a day came my parents both were to work and my little sister was with a girlfriend. So I turn on the laptop, look for porn and start going. Halfway there for some reason I look into the backyard (the laptop stands close to the backyard window) and see my sis WITH her girlfriend. Never have I so quickly zipped up and closed porn. I don't know if they saw anything but it was never mentioned.

[Gothedrill]

I was using my laptop and jerking off.. this was after about a week of not cumming. My balls where killing me and my cock was throbbing like crazy. i was fully dressed i just had my pants undone with my cock out. I was just about to bust when i heard someone coming in. I freaked out and grabed my laptop to cover my lap. I ended up just smashing my cock and balls with it. It hurt bad, but also so good. I blew a massive load under my laptop and all over my lap. after a minuter i got my junk put away without anyone seeing but i had tosit there covered in jizz till they left.

[Naughty_Challenger]

Well, it's a good real good thread...

I've got two to deliver, quite humiliating/sad.

Starting with the first and keeping the other one for the next time: It was about 4-5 years ago when I was still studying. I went with my parents and I think my two brothers and that time the family of my one brother to the sea side in Germany. I had my own room, yet I felt super-daring a couple of nights, but especially this one. I thought to myself: Why not going for a beach walk in the night alone and wank there?

Well, my family was in bed when I decided to go. I was old enough, so no one would have said or asked, what I did. I went there where a lot of beach chairs were. I hadn't seen anyone on the way or around and checked all of them around. There was no one. But there was one person at quite a far distance (who was probably following me I later realized..).

I started unzip my pants and wanked my dick which grew very quick and was very hard due to the unknown environment and the possibility that someone could have caught me there... But soon I realized this person was approaching towards me and was maybe 100m, 200m from me away? Can't remember the distance, due to the fact it was full moon I think things were quite visible...

I packed my dick away and sat down in a chair. I waited and looked around 2min later. This person was closer and looking towards me! I panicked almost, didn't know what to do. I just thought: "Well, what could happen in worst case?"

Worst case happened: Shortly after this old weird guy was standing next to me and asking me something like "Are you interested in sex with me or similar?" It wasn't that direct, but obvious, what he wanted. I don't know, what he saw from what I did, but it was definitely embarrassing. I denied and went home, not horny anymore... ;)

@Saphire: By the way, where is your story?

[freddy12345678]

i was alone and was dared to cum and swallow it, so i got naked a d started jerking off on the couch downstairs, and at some point my sister came home and when i noticed, i already had the cum in my mouth and started choking on it.

[SlavePuppy]

My brother walked in on me mid orgasm. Naturally I pretended I was yawning. However, when I went to the toilet he started searching through my history on my phone. Worst thing is he was 10 at the time. I exposed him to his first taste of poem and it was pretty kinky shit