This is a bit longer than I intended but hopefully it's a good read.
So my neighbor growing up was a total MILF. I'm talking only 32 years old, big boobs, big ass, toned abs, tan, beautiful face - the whole package. She was my mom's best friend, her son was my best friend, and we shared back yards. I was over at their house constantly. Around the time I was 13-14 she became single and coincidentally I started going over there more and more often to hang out with her son/my friend. The bulk of this story takes place about two years later when I was ~16, entering my junior year of high school.
Well one time I'm over there and we're downstairs playing Xbox. Well my friend went into the bathroom downstairs to use it and I really had to go as well and couldn't wait so I went upstairs to the bathroom I rarely used. It was one right next to the MILF's bedroom. So I do my thing and realize I'm out of toilet paper so I start searching around. I open the closet door and see a laundry basket with a nice bright pink thong sitting right on top. Heart stop, instant boner, freak out and so on. Everything else was forgotten and I partook in the most serious session of masturbation in my entire life. To this day I have not had one better.
That was the first time I jerked off in her bathroom. Over the course of about 6-8 months I eventually lost count. I went over there practically daily and almost always went to the bathroom, found a thong or bra(34C, by the way) and jerked off while either looking at them, holding them, wrapping them around my junk, or whatever. I rarely actually used the bathroom there but spent probably 5-10 minutes there every time. My friend was just oblivious. He was roughly a year or so younger than me so either he wasn't beating it yet or just did not realize how I felt about his mom. Who knows. Who cares. We're not friends anymore.
Anyway, I thought I saw signs that she liked me too. She always wore Victoria's Secret stuff and got the catalogs and everything. Every time one came in she would always give it to me and say "Tell me what looks hot" or "Find the good stuff" and give me winks while saying it. She'd bend over and grab things on the floor with perfect shots of her ass at me and would wear low cut shirts and bend over in front of me to let me get a look at her cleavage. Maybe it was not deliberate and it certainly was not very many times, I assure you, but often enough that it got me thinking that I was not the only one with feelings. Oh, and she had absolutely the BEST smelling perfume in the world.
So one time I'm going to a buddy's house(not her son) and I am bringing my Xbox over so we can play. I only had one controller, so I call over to my neighbor's house to ask if I can stop by and borrow a controller for the night. MILF answers and says they're heading out but the key is hidden under this rock so I can unlock the door, get in, and grab it. So I head over, get in, grab the controller, and have to go to the bathroom. I head upstairs and run out of toilet paper. Blast from the past, I see a thong in the laundry basket. I don't know what I'm thinking but I stuff it in my pocket and head out. Get to my friend's house and bust it out to brag like I got it from some girl. Well I did not realize that I can't really put it back. Like it just appears back in the laundry basket a few days later next time I'm over? I can't really hide it somewhere else in the house hoping she'll find it. So I hide it in the back of my closet at home and call it good. Totally forget about it. Months later(near the end of Junior year) I find it and in a moment of guilt head over.
I'm beating around the bush trying to figure out how to tell her and I'm following her around helping her clean this or reach that, talking for about an hour. I had more than a few looks at her ass or boobs or whatever. I figured it was time and in my head it was about to be a Brazzers moment. I tell her I stole the thong and ask if she wants it back. She laughed at me and then just asked me to leave. I keep talking and trying to explain it off thinking I can salvage losing my V-Card to a 10/10 MILF and she just shakes her head and laughs, says "Hormones are a bitch, huh?" and guides me out the door. I stopped going over there as often and saw her less frequently. But next time I did see her it was like nothing happened. She hasn't mentioned it since. I threw the thong away a few days later.
I eventually told my current girlfriend of almost two years and she brings it up from time to time to make fun of me. Oh well. It's a funny story. I haven't really told anybody else.
Hope you enjoyed it, Gaf.