This is my story of masturbation, watching my sis, watching me in 1962.
I was about 15 Years old, and by this time had been masturbating since I could remember, but what happened is burned into my memory.
I was sitting on my bed one day using an old milk bottle, the kind used in the 50's. They had an opening about the size of a half dollar maybe bigger? I would put some lotion or vaseline on my dick and start fucking the bottle, this would act like a cock ring and my dick would swell up really big with veins bulging out the bottle, it also had a magnifying effect. I would also use it like a vacuum tube by using some plastic hose for air pumps used in aquariums, by forcing my dick in the bottle beside the hose, and sucking on the end of it I would create a vacuum, and pull the tube out very quickly. I could sit there and wave the bottle up and down and the suction would hold the bottle on. I could also pull it very hard pulling the skin up to the head of my penis and it would pop back into position at the base of my cock, and my cock would just keep growing.
I was looking at some vintage porno I had got from the boy down the street, he would sneak it out of his fathers secret hiding place. This stuff had these black and white pictures with women that had very hairy pussies, and people fucking and sucking in various ways, man this stuff still turns me on to this day, well you get the picture by now.
I had been sitting on the end of the bed which faced a walk-in closet that was about 10 feet long with folding slatted doors. My father had made this modification to my bedroom and my sister's bedroom with the same closet on her side of the wall. In the wall was this hole about a foot or two in diameter, maybe more, actually more, that an old stove pipe had been in before he added the closets(it was about three feet from the bottom or maybe waist high). He had left the hole there for some reason and never finished it. Well one day I was going at it and the closet door was open on both sides you could see in the next room, I thought my sis was outside playing.
I noticed a leg move across the opening, that was when I knew she was watching. I got very embarrassed and got up quickly and pulled up my pants, and went to the bathroom to finish up and got to thinking about her watching me and if it excited her. She was 14 and had a very nice set of tits and looked much older for her age. But we were always fighting and I had never thought of her in a sexual way before.
Well the next day I decided to give her a show and was getting very excited thinking about it. I'm not sure what or how that worked but it got me going. First I just sat there in my underwear, fondling myself with my hand in my jockey shorts, then I noticed her get into position and move across the opening in the closet wall. I noticed if I slid down and put my lower half straight out from the right side of my bed, she would have to edge closer to my left to get a better view. I could see a necklace she had on hanging down and I knew I was close to seeing some action. Then I saw it! She had her panties pulled down to her knees and was working her hand in and out between her legs like she had done this many times before. I thought I was going to cum right then, so I decided to pull my jockey shorts to one side and expose my cock for full view. (I had a very thick cut cock about seven inches long, with very large veins and nice dangling globes for balls)
By now it was throbbing and moving up and down every time my heart would pump, and I don't remember it ever being so hard and purple from excitement and leaking pre-cum. It was running down my shaft in copious amounts. Well I started to pump it some and just squeezing it very hard at the base. I was afraid I would cum, because every time I started to pump my hand I would have to clamp my sphincter muscle to hold it back (I had learned this from lots of practice). It was then I noticed her tip-toe out of the closet, and I saw her well rounded ass and her legs were slightly apart. I could see her pubic hair as well, which looked very bushy. Damn! was all I could think, well I thought she was done, I was thinking Damn!
Then I saw her grab a hairbrush off the night stand beside her bed and then tip toe back to the closet. Oh damn again! I got back into position moving slightly to my right to force her to move forward and closer to the hole. My head being to my left and almost in a prone position, I could see she had the brush in her hand holding it by the bristles and forcing the handle into her pussy lips. She had a very hairy bush and I could smell the musky odour of sex coming from the hole. I remember my face was blushed and it seemed my whole body was on fire like nothing before.
I had been holding back for some time to watch the hand and brush move back and forth. She had a window behind her and was back lit so I could see her pubic hairs really good and the swollen lips. By now my throbbing cock was getting what I call a puffy feeling from being so swollen up. The pre-cum was running out and my dick suddenly got very hard and I could not hold it any longer. At first the cum started to roll out like its being forced over a wall, then I let go and it started shooting ribbons of cum out. The first stream seemed like it shot about seven or eight feet. I had never shot so hard in my life and my balls felt like they had burst or turned inside out. I was still pumping with my chest pounding and making gasping sounds from my mouth. I could see her hand get very quick and she was making jerking movements to and fro. The sight of me cumming had put her over the edge also. Damn what a thing to actually see for the first time!!! This is a true story.
Well this was the beginning of lots of days of fun, which I will tell you about later.