This story happened to me when I was 15 and now I'm 31. I've enjoyed playing with my cock every chance I get since I discovered it felt amazing at age 11. I did the math and figured I've blown about 20,000 loads of cum alone. So after rubbing out so many loads it's hard to imagine that any would stand out.
One of the best times I had was when I was 15 and I had been hired to babysit a boy who was probably old enough to stay home alone for an evening while his super hot mom (MILF) was out on the town. Well, the MILF had picked me up at my house and brought me over to her condo where her son was busy playing computer video games. She instructed me on emergency phone numbers and that sort of stuff and told me to make myself at home. So after she left I hung out with the kid I was watching and when he got bored with me I left to go to the bathroom and on the way I had a look through the kid's mom's bedside tables and found some magazines. Those 'zines can turn a horny 15 year old guy on quickly! I thought I might find vibrators or dildos or sexy books but I didn't. So I flipped through the pages of the mag for a while and got a boner of course.
I checked in with the kid I was babysitting and told him I was going to watch TV downstairs while he played alone. I went downstairs and decided I ought to have a look around the bathroom drawers for anything sexy I could find. This was my first time in a MILF's condo so I wanted to see what I might find. I found condoms! Some of my earliest masturbations were with my dad's Trojan's. When I was 11 I would unroll those big rubbers down my cock and pee a little bit in them and slide them till I came a few minutes later, then flush them down to hide the evidence.
This time though, the condoms I found were made of natural lambskin. WOW. What a slippery feel. I read on the label that the natural material wasn't a total barrier to pregnancy or STD's but that didn't matter to me... I just wanted it for it's slipperiness on my stiff boner. My heart raced as I played with my cock as the MILF was out on the town enjoying herself as I enjoyed myself in her condo while her son was upstairs playing video games. I don't remember how many loads of cum I shot that night but when that hot mom came home I sure hoped I didn't leave a trace that I'd rummaged through her private drawers and even masturbated my raging 15 year old cock with her sexy slippery condoms.