Rigged spin the bottle game

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So about 5 years ago when I was 15, I had a nice gig babysitting around the neighborhood.

One time I was doing one of the most expensive jobs I’ve taken, since I had to babysit one 12 year old girl called Jamie with three of her friends, and all the parents were paying me to sit this one night, so it was four times the pay.

The girls were gathered around Jamie’s new iPad, it had been out for about a year at that point, and they were all gathered around it and fiddling with it, I was pretty okay with that, since that meant I could just ignore everyone and relax with my own phone.

suddenly I heard Jamie


Blackmailed by Step Sister

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Word of advice, if you’re gonna listen to something while you jerk off, make sure you have complete privacy, or things could get real bad like they did to me.

It was a while back when I was 15, and I didn’t have a computer of my own back then, and it was really hard to find masturbation material that was easy to hide for me, plus I was still kinda young so I didn’t know all the ins and outs.

I tried to find inconspicuous things to jerk off to, like small clips I could fit in my phone, or pictures in magazines or catalogs.

I had gotten suggestions from a friend in school to use audio materials, and he gave me a clip of a girl dirty talking and making suggestive noises, and so on.

In hindsight, I really should’ve probably locked the door, but I got naked and tried to close my eyes and “enjoy myself”, and I was actually getting into it when I heard a laugh.

I opened my eyes and saw my older step-sister, about 17 years old, with her shiny expensive camera phone (it was a while back, and she got a job to buy the thing), I instantly figured she got a picture or video of me jerking off.

I panicked, and begged her to not tell anyone or show anyone, she laughed and said that I would have to do whatever she wanted from now on.

I know I couldn’t say no to her, and it didn’t occur to me to tell my parents, so I agreed to essentially do whatever she wanted.

To make sure I was going to listen, she told me to finish jerking off, and so I stood there beating off and jizzing into my hands while my own step-sister laughed at me.

From then on, whenever my parents weren’t looking, she would make me do all her chores and treat her nicely and essentially act like her manservant, but that wasn’t the end of it.

One time when my parents were out, she invited a couple of her friends, including a younger sister of one of her own friends, who was around 13 at the time, I guess.

They made me stand in the living room and strip naked while they sat and watched, and then proceeded to play with me and pose me and make me do and say all sorts of embarrassing things, they finally let the younger sister jerk me off until I came before making me fetch them food and drinks from the kitchen.

And this continued until she finally graduated and moved away to college a year or so later, and I was more or less released.


Caught Masturbating By My Sister

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So This was about 12 years ago, I was 15 at the time, I had just started masturbating this year and I really enjoyed things like phone sex and dirty talking and the like, since it was an easy way to jerk off without having to hide anything if I get interrupted.

I usually locked my door when I masturbated, but this time around it was late at night and I forgot to do it, so I got completely naked, lay down on my bed and put on my noise cancelling earphones, I began jerking off and getting into whatever track on my MP3 that I was listening to, and I didn’t notice my older sister by two years walk in, she didn’t say anything and continued watching me masturbate, and she had just bought a new phone with a camera in it, so she began filming me masturbate naked on the bed.

I didn’t realize she was there until just before I came and heard her just laughing out loud, I instantly got embarrassed and covered up, she told me to stand up, and I did.

She then told me to finish masturbating in front of her, and this was so humiliating but I did it and I came in front of my sister who kept filming me.

She then told me that she owned me and I was going to do whatever she wanted me to do and started making me do all her chores, but that wasn’t the worst of it.

One day when our parents were out, she called me downstairs and I followed her, I saw a few friends of hers and one little girl about 12 years old, they told me it was her birthday and then she told me to stand in front of everyone and strip naked, I tried to tell her no but she said if I didn’t do what she said she’d show the video to everyone I knew in school, I couldn’t call her bluff and I stripped naked.

They then told me to start jerking it, and I did so and came in front of a group of girls and even one preteen, they even made another video, then they kept me around for the rest of the night so that they could have fun playing with my penis and using me as their butler that was humiliating.

My sister left to college next semester, but before she did, she did this a couple of times, she even had me jerk off outside on the front porch in the middle of the night.


A 13 year old girl made me strip nude and masturbate in front of her!

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A 13 year old girl made me strip nude and masturbate in front of her!

I knew as soon as I saw her beautiful blonde haired blue eyed face approaching that she was coming to watch me masturbate and cum. She said, ” I want you to take off your clothes right now.” So I stripped nude and my dick was hard already! Then she asked me, ” Can I watch you Masturbate?” As I began to masturbate she stood in front of me watching me masturbate. She was so gorgeous and sweet, she really let me take my time masturbating. I knew that she wanted to watch me cum and that she would stand there looking at me while I was masturbating for as long as it took for me to cum, so I took my time. My prick was so big and hard, I occasionally let go of it so that she could actually see it throbbing. I wanted her to know how much I loved masturbating in front of her so I looked at her and smiled while I was masturbating in front of her. Then I started cumming, I just couldn’t hold back any longer. When I came she saw my cum squirt out several times and she stood right there watching until I completely finished cumming. As I was cleaning up my cum she smiled and then walked away.


Strip Poker Loser

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So this one time when I was 17 I went to my girlfriend’s place to have fun with her and her best friend, who also brought her boyfriend.

We had stolen some beer from the fridge and were kinda buzzed, when my girlfriend suggested we play strip poker, everyone seemed okay with it, I was still kinda worried, but they kept insisting and I finally went with it.

we played until one person was naked, sadly, that was me, I was completely naked with my cock showing (six inches), the other boyfriend was in his pants, my girlfriend was in her underwear and her friend was only in her panties (she had pretty great tits, so I was kinda stiff).

The other boyfriend took his girl away to have a quickie I guess, leaving me with my girlfriend who started making out with me.

Soon we were interrupted by the happy couple again who were now dressed, the boyfriend said he had to jet and left almost immediately, I looked around for my own clothes but couldn’t find them anywhere, the friend told me she hid them away, and while I was distracted, my girlfriend put her clothes back on and I was the only one left naked.

She told me to go home, and when I asked for my clothes she told me she’d keep them and that I had to streak home (she drove me here).

When I said no way she told me that the only other option was for me to put on a show for them, they took out their phones and started making a video, they forced me to say out loud that I lost strip poker to two girls and I had to pay the price, then they told me to jerk it.

I started beating off and came very quickly (Quicker than I wanted) all while they filmed me and giggled and made fun of me, I remember jizzing on a glass coffee table they had.

She finally took me home naked, I never got my clothes back and I found out later that she did this with all of her other boyfriends, they usually said nothing because it was humiliating, and so she wouldn’t let the videos out.

ofc we broke up soon after.


Caught masturbating at work… twice!

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Okay, so my last job was in this really small office.

The office was split into three rooms and I shared my room with two women, both in their early 40’s (I’m 25). These two women are insanely hot, too. Fitness freaks with very toned bodies with a tendency to wear low cut tops and tight trousers.

It had been quite a while since I had last gotten any, so I had really started to obsess a little over my colleagues. OK, a lot.

I guess it evolved over time, I had a corner-desk that shielded my lower half from view of anyone in the room, so it started with my just rubbing it through my trousers. That then turned into rubbing it through the pocket, to putting my hand inside, to eventually whipping it out and jerking it almost every day at work.

The biggest problem was that the longer I went without getting caught, the less cautious I got. I was even trying to push it, a little further.

If nobody was looking, I’d unzip and take it out while standing up, and then start beating off as I started to sit down. I’d even let out the occasional quiet moan, here or there.

Never get cocky. Okay, maybe just never beat off at work but also don’t get cocky.

How’d I get caught? Well, one of the women in the office went over to my desk to ask me a question. Normally I’d stop as soon as she got close enough to see my arm moving, but this happened just as I started to blow my load, and something like that is hard to stop.

She laughed a lot. A hell of a lot. She told the other woman in the office, and then I got questioned as to whether or not it was over the two of them. I admitted that it was, since it seemed like the least embarrassing part of all this.

They didn’t report me to any higher ups, but they ripped on me mercilessly. I took it and figured it was worth the humiliation to keep the job.

The other woman (not the one who caught me but the one who she told) used it quite a lot to blackmail me. I had to do her work for her, cover for her if she had to run out and take the blame for any of her fuck ups.

One day, she approached me and told me that I had done so much for her that I deserved to be cut a little slack. She took me into the office where both the women explained that they were okay with me wanking at work, as it gave them a confidence boost, on two conditions.

1. I had to do both their work for them
2. I had to tell them when I was about to

I actually didn’t do it, for the longest time. It felt kinda weird telling two people who I knew were going to rip on me that I was about to beat off. Plus, the extra workload would’ve killed me.

But of course I ended up buckling, after a night out where I came THIS close to getting laid, and failed spectacularly thanks to me utterly misjudging the strength of Sambuca.

I told them I was going to do it, and started beating off. They were laughing and calling me pathetic but I won’t lie, that didn’t really kill the mood.

I finished up and they ripped on me some more, then I was faced with the mammoth task of doing their work, too. BUT I kinda liked this, now.

The next day, I did it again. I told them I was gonna beat off, I got started and this time they didn’t really rip on me, they were laughing but that was it.

I was getting fairly close to orgasm when, all of a sudden, they rushed me.

One held me in place (not a difficult task as I am skinny and have no body strength to speak of) and wheeled my office chair from behind my desk. The other pulled out her iPhone and started filming me and my twitching, rock hard member.

They called me tiny, they ripped on me some more AAND then they posted the video to Facebook and tagged me in it.

I don’t know if there were any repercussions for the two of them, but I walked out of that job quicksharp.


Busted by Coach

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When I was growing up in rural southern Texas in the early 1980s, I had to deal with two big things: puberty started when I was just ten and I realized I was gay.

The new hair on my crotch was embarrassing as was the sudden almost overnight increase in the size of my junk. Then I discovered masturbation and became a preteen sex fiend behind bedroom and bathroom doors. Privacy was a big deal suddenly.

This would have been okay except I also started in grade school and that entailed mandatory showers after PE. Everything was unnerving for me as I was the sole white kid in my gym class and the coach was a hard-ass who seemed to enjoy making guys squirm. As we all shyly stripped down, he barked at us that we had to hurry up and stop being embarrassed. Then he noticed me as I got down to my underwear.

Coach came over and made me open my tighty whities so he could confirm his suspicion about my ample basket. Then he stepped back and barked out that I was becoming a man and needed to wear a jockstrap to gym. All the other guys were starring and ogling me as I had a head start on physical maturity– my junk was already close to full-size while everyone else was still sporting baby-sized, smooth genitalia.

I was so humiliated. Add to that at the end of gym we had to share the showers with older boys from another gym class or the football team when they had came in from practice and it was the perfect storm for humiliation and raging uncontrollable hormones.

The sight of older boys who’d hit puberty and who were comfortable walking and talking with everything bobbing and swinging around along with the sight of so many athletes and the aroma of raw sweat and testosterone coupled with my hair-trigger libido was too much to resist at times. For those moments I would shower as fast as possible and if I had the inevitable erection, I’d duck into the bathroom that was literally a step from the showers.

I would masturbate so I could have some much-needed relief and manage to hold onto what little dignity I had.

The bathroom was a spartan, cinder block affair like that rest of the old gym. There were no privacy, no stalls, nothing. If a guy had to piss he’d just step up to a wall-mounted trough and do his thing while shoulder to shoulder with everyone. If he had to take a dump, he pretty much better get over his modesty as the toilets were lined up in a row opposite the trough urinal with no stalls.

One fine day in late Spring I was indulging my sick little game of relief at the trough urinal and right as I shot a massive wad up to eye level on the wall in front of me, who should step up next to me but the Coach?! I stood there frozen in fear already figuring the massive, masculine-reeking cum stain that was slowly dribbling down the cinder block wall in front of us both couldn’t be overlooked but Coach just calmly took a piss and never said a thing! I hastily beat a retreat into the locker room to finish toweling off and got dressed at light speed that particular day!

From then on, I learned to put up with my raging hormones and tried hard not to masturbate when I couldn’t be in a locked, private place.

I’m still gay today too.


The not so secret masturbation…

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After staying at school to help with a few things and being very tired… I finally went to the girls locker room to change myself up. When I got naked, I looked outside. It was sunset already… and that gave me a though. I started to rub my breasts a bit… it felt nice… ran my fingers around my pussy… felt REALLY nice… I sat down and started to masturbate! I moaned loudly and passionately at my own masturbation! No one would hear… but it was still risky, doing this in school… Then I started to moan out the name of my crush for that extra turn on effect… I closed my eyes and thought of him touching me. “OH JASON! JASON!” I screamed out of my lungs. Then I looked at the window again. I saw three guys, one with a camera, looking at me and recording all of my actions! The window was half open too, so they probably heard me yelled Jason’s name! I ran towards the window and the boys ran away. “DON’T YOU KNOW HOW TO GIVE A WOMEN SOME PRIVACY!?” I told the sixteen year old boys in my grade who were still running away with the video footage of my masturbating… They saw me from the front too, it was completely humiliating!

The next day at school was even worst… apparently they had showed the video to a LOT of the boys and some of the girls… EVEN JASON! When he came to me, he started to talk. I was so nervous and embarrassed… “So you yelled my name, huh?” He said. I left him. I didn’t want him to humiliated or embarrass me with that story. Some of the girls thought came to me and tried to cheer me up and told me that I was just in the heat of the moment and that doing it like that was passionate and really nice. It still didn’t cheer me up.. all of the boys in the school would see my naked body and see me touching it in ways they only wish they could, moaning out the name of my dream man while doing so…



caught fucking a plush animal

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So I was 14 back then when I was really horny alone in my room. I was so turned on when I decided to masturbate but I was so dumb. I did not take any security measures at all.

I wanted to try something new than the normal rub penis with hands thing. I wanted to simulate a real sexual experience. And then it came into my mind that I had some plushes lying around in my room and I cut a hole in the bottom of one. I then fucked it, all the while having porn magazines in front of me, looking at women. I was completly naked when my 2 sisters suddenly entered the room. It was the biggest shock in my whole life as they saw me doing that.

I was so shacky and my voice stuttered as I desperatly tried to find any excuses to difuse this awkward situation. I quicky put on my pants and stuttered like crazy. I told them I had lost something in my room. But it was too obvious, they caught me lying on my plush with my penis inside the whole I did on its bottom, doing humping movements.

My sisters said nothing and left the room. I never talked to them about this in all those years and I will never do it. They also didn’t. But my relationship to my sisters has changed a bit for me. And I guess for them too, as they saw their little brother going all horny. They realised that I was a man too, and had sexual pleasures to fulfill.


First time ejaculation

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I was 12 years old. But, for many years before that, I had always enjoyed having an erection. I would play with it, knowing that touching it felt good. But that was about it. As I matured, faster than most of my friends, having my cock grow and get pubic hair, I had always heard the slang about jacking off, but not knowing and/or understanding what it meant. One day in the shower I decided to give it a try. I lubed my 12 year old dick with soap and started stroking it. At first, I thought it was really silly. It seemed weird rubbing my dong. I remember I started to laugh because I started to feel a little stupid. I kind of thought I was doing it wrong. Then, my dick started getting harder and my body began to tense up. I knew something was happening, but I didn’t know what. I started to ejaculate and I panicked. I let go of my prick just at about six strands of creamy white sperm shot out. It actually flew across the bath tub and hit the wall. I was totally freaked out! I couldn’t believe that I had actually ejaculated. I cleaned the wall and stood in the shower, stunned by the ordeal. I had to think about this. I thought about it for about a week before I decided to give it another try. I remember going to the bathroom, getting in the shower and making a calculated effort to begin stroking my dick right from the get go. I jerked it vigorously, anticipating what might happen. And then, bang! I shot cum all over the wall again. It was glorious! What a wonderful discovery!