I found this site about two years ago and love it, but here is the first story I have submitted.
This story happened when I was 13. My friend, Mark, was a year younger than me. Our Mum's were good friends too, so we used to hang out a lot together. This particular year we spent the entire summer at each other's house, often sleeping over. We mainly spent time outside; playing football, climbing trees and making 'dens'. Generally being typical boys.
Mark's 15 year old sister was called Charlotte. I'd just started noticing girls and I often sneaked glances of her when I thought no-one was looking; particularly when she bent over or stretched to get something from a high shelf or one of the kitchen cupboards. She was really quite skinny, so she didn't have much of an ass but her small A cup breasts were clearly visible when she wore t-shirts or vest tops. I was kind of shy around her, mainly because I was paranoid she could read my mind about the 'naughty' thoughts I had about her (and nearly every other girl I knew!) or that she'd notice the semi hard-on in my pants whenever I was around her.
Their house was quite an old design and above the doors was a glass panel that allowed an unobstructed view into the room beyond. This included the bedrooms and bathroom, where surprisingly the glass was barely opaque. When Charlotte was taking a shower or bath, Mark and I would wait to hear the click of the lock and then dash to stand outside, listening for the shower to be switched on or her plunge into the bath water. We take turns to stand on the landing banister rail and lean across to look through the window and watch her. It was best if she showered as the extra noise concealed any sound we might make and she was also more distracted and unlikely to catch us peering in. Whoever was watching would relay to the other person what they could see and I sometimes exaggerated, pretending she was stroking her breasts and rolling her nipples between her fingers.
These voyeurism sessions usually ended with us both trying to hide our obvious erections from each other, before making our excuses to go to the downstairs bathroom and, certainly in my case, 'relieve the tension'.
One time, when Mark was engrossed in some computer game, I enjoyed the crowning glory of any previous experience watching Charlotte. I took up my usual position, perched precariously on the banister rail, and watched through the window as she undressed, affording me a great view of her tiny ass, bending over and stepping out of her knickers. She had already run the bath water, mixed with bubbles, and lay back submerged up to her neck. The water was quite deep, but her nipples and tips of each breast, along with her legs from mid-thigh to ankle were exposed. I was desperate to see what she would do next, but daren't look too often for fear of being discovered, so kept bobbing my head down from view. After a few moments I resumed my viewing and, just in time, was rewarded by seeing her slide her right hand down over her stomach and between her legs, while her left hand moved across her body to slowly circle the bubbles covering her right hardened nipple.
Oh my God, she was touching herself and she was blissfully unaware that I was watching everything! I stared wide eyed, not quite believing what I was witnessing. She was the first naked girl I had ever seen, apart from my sister and younger cousins, and not only that; here she was masturbating!
She closed her eyes and pushed her head back, so just her face was above the water line. This was great for me on two counts: 1) I got to watch her totally engrossed in pleasuring herself and 2) with her ears submerged she was unlikely to hear any sound I may inadvertently make.
For the next five minutes I was transfixed as she continued to move her hand over her pussy (I couldn't see directly as it was obscured by the water and bubbles) occasionally clasping her legs together, as her other hand alternated between pinching her nipple and lightly brushing her palm across it in sweeping movements. Finally, she squeezed her legs together one last time, stretched her neck muscles taut and was completely motionless, but otherwise did not give any outward sign of having climaxed.
I didn't know how Mark would react to me telling him what I had just witnessed; would he be creeped out because it was his sister or angry with me for not telling him to come watch, so I didn't tell the full story, instead just saying she'd taken a bath like we'd both seen many times before.
A few nights later, during a sleepover at my house, I decided to be bold and asked Mark if he masturbated. He was a bit evasive and eventually said that he didn't, but asked if I did and when I said yes he asked a few questions about what I did, how I did it and what it felt like. I explained my basic technique of making a fist and holding myself while moving my hand up and down and how it felt great when the cum squirted out of my dick.
The next time we had a sleepover was at Mark's house a week later and it was a really hot and humid night. He lay in his bed and I was on a blow up mattress on the floor at the side. I was lying on top of the duvet because it was so hot. We chatted for a while about what we'd done that day and our plans for tomorrow and then Mark told me that he'd tried masturbating since we'd talked about it the previous weekend, but he wasn't sure he was doing it right. He said his cum had squirted out of his dick but there wasn't much of it. I explained this wasn't a problem and maybe if he did it more frequently he'd produce some more cum. There was a moment's silence; then I asked 'Do you want to do it now?' He didn't say anything so I ventured 'We'll both do it at the same time, so we can see how each other does it.'
'Ermmm, ok, I guess.' he replied.
Ceasing the moment I sat up to remove my t-shirt then wriggled out of my pyjama bottoms as my hard dick sprang to attention. It wasn't very big at that stage, but quite thick. In the twilight I could see Mark half sit up and turn towards me to get a good look, so I lay back and let him see me completely naked. He didn't say anything, but turned to shuffle around and remove his boxers. As he lay down again I could clearly see the tent he was making under the sheet. I'd seen him naked lots of times before, when we used to share a bath, so I knew he was circumcised.
I started stroking my cock, using my usual technique of moving the foreskin back and forth and wondered how Mark did it. I could hear the steady rhythm of him masturbating on his bed and this made me even more excited. I couldn't believe we were actually doing this; lying naked in my friend's house openly masturbating together. After a few minutes of stroking I felt the now familiar tension in my balls and shot four or five thick ropes of cum all over my chest and stomach. Moments later I heard Mark's breathing intensify; then he grunted a couple of times coinciding with the telltale noise of cum splattering across his body as well.
Neither of us said anything for a few moments as we caught our breath, then Mark broke the silence and asked 'Does it sometimes look different? I mean, your cum. Is it sometimes gooier?' I replied 'Yes, it does kind of vary. But one thing always remains the same...it feels great!' I grinned. Mark turned to peer over the edge of the bed at me and grinned back at me. 'Yep, it certainly does.' I lay there basking in his gaze as my cock subsided and the cum liquefied and pooled in my belly button. We grabbed some tissues and cleaned up before falling into a contended sleep. I inwardly smiled to myself, knowing I had opened a new chapter in my life and determined to make the most of the opportunity.
The following morning, as we walked in the nearby woods looking for branches to complete the roof and walls of our 'den', I suggested to Mark that we form a masturbating group called 'The Finger Stripe Club'. The name was based on the stripes, or ropes of cum, you get across the back of your hand when you ejaculate. The idea was that we would get together with friends and have 'wank off' competitions and collect our cum in a jar. Mark agreed and we celebrated by having an inaugural masturbation session in our hideout. It was so liberating, and at the same time daring, to stand half facing each in broad daylight with our shorts and pants round our ankles and feverishly masturbate before coming on the ground and wiping our dripping dicks on dock leaves, before hurriedly getting dressed.
Unfortunately the masturbating group never really happened as I hoped it would as we were too nervous to suggest it among our different circles of friends, but one time about two weeks later we did persuade Mark's friend Adam to join in. We'd been swimming in their pool and were all getting dried in Mark's bedroom. As he removed his swim trunks to continue getting dried it was evident that his dick was semi-hard and after a few seconds of being in the cool air he was rock hard, desperately trying to bunch the towel over his crotch. His face coloured bright red and he kept his eyes firmly fixed on the floor. Seeing Mark had started to get my dick twitching so, being the eldest, I boldly pulled down my trunks, releasing my stiff dick and making no effort to cover myself. Slowly, I started rubbing my cock. Nobody said a word, so I just stood there and continued stroking before Mark joined in. Adam's stiff dick was obvious in his wet trunks, so after what seemed like an eternity I broke the silence and said 'Join in if you want.' He glanced at Mark, who nodded his approval, so without saying a word he shrugged and slipped out of his trunks as well.
His dick was quite long but very thin and unlike me and Mark, he didn't appear to have any pubic hair yet. I couldn't believe that all three of us were standing there naked and masturbating. At last, my 'Finger Stripe Club' seemed to have been formed! By now we were all vigorously stroking our cocks with intense looks of concentration on our faces. I didn't know if it was because we were all really focused on our own sensations and enjoyment or because no-one wanted to make eye contact. I sat down on the floor and they both followed suit so we were all facing each other in a rough circle, but not close enough that anyone was touching. We feverishly masturbated until first Mark and then Adam shot thick cords of cum all over the floor in the middle of us all. The first two squirts from Mark's cock flew across the space between us and landed on my leg just as I reached orgasm. I lay back in my preferred position to cum on myself. The first shot went high in the air and flew over my head hitting the wardrobe directly behind me, the next on my neck as I threw my head back in ecstasy and the others falling on my chest and stomach. After a few moments of what felt like a semi-consciousness daze I looked up to see Adam staring at me. He was wide eyed and just said 'Wow! That was amazing!' We quickly cleaned up, as best we could, not knowing if Mark's Mum would notice the stains on the carpet and it was only after we'd dropped the numerous tissues in the bin that I remembered my idea of collecting our cum. I was intrigued to see how much we could collect and how long it would take to get a decent amount in a jar.
Over the remaining weeks of that summer school holiday Mark and I enjoyed countless masturbating sessions together in various locations - our hide out in the woods, behind the garage, up a tree, in the bathroom, in our bedrooms, everywhere we could think of! Occasionally we would masturbate each other, but both of us preferred our own techniques so we'd mainly just look after ourselves. Sometimes we had 'cock sword' fights by swiping and slapping our erect dicks against each other, laughing as they sprang from side to side and back and forth or after ejaculating rub our sticky cocks against each other and run our hands over the wetness it created. However and wherever we did it, we always collected our cum in a tall tuppaware container I had found in the kitchen. It had a screw top lid so was just right.
Our favourite masturbating places were in the hide out or at Mark's house in the bedroom eves - basically a storage area running the length of each first floor room that was only accessible by a small door at one end. It was perfect for our private game as we could sit at the far end and pile up boxes and toys to prevent anyone seeing us if they ever did happen to look in. It was so warm in there that we mostly stripped off naked. We'd sit for hours, masturbating and looking at a couple of old copies of Playboy that I'd bought from a school friend's older brother. At the start of that summer, when I'd been playing hide and seek with my sister, I'd also found a pile of old Pirelli calendars under my Mum & Dad's bed and had smuggled one to Mark's house. I recall there was a great full size photo of a tanned woman's naked torso, cropped from neck to hips, depicting her full breasts and hard nipples covered in beads of sweat or maybe water. This was our favourite image and after flicking through the various pictures spread across the floor as we masturbated we'd often finish by coming all over this photo imagining it was a real girl.
After each orgasm we'd carefully scoop up the cum and pour it into the jar to add to the collection. We never did get caught, but the daring nature of what we were doing made it even more exciting and forbidden.
The opportunity to put all my practice to the test with a girl came some weeks later with Mark's sister Charlotte, but that's a story I'll save for another time...