When I was in high school I was dating this bombshell of a woman, brunette with freckles and the cutest smile who was very petite and still had some nice Cs and curved ass, and i was head over heels for her. She was into me and my personality but had a weakness for my tiny penis and athletic guys, and with me was very dominating but around an athletic man she was very submissive. When she met my best friend who was a tall, muscular, skater punk she was minding her "yes sir"s with him. I was still a virgin and didn't think anything of it, but she started to wear more and more revealing clothing too. I should have realized with how flirtatious she was with him, even though he has a girlfriend, but her and I were both virgins and I didn't think about it, but I didn't, and the cuckolding started unknowingly at him house. His parents were out of town and we were drinking there, but his girlfriend never showed up. I was pretty drunk and claimed i had a huge dick. My gf kind of giggled but he was calling me out on it. Eventually him and I got into a very heated argument over who's dick was bigger to which my laughing girlfriend said she can get a ruler and we can find out and settle it and he volunteers her as a judge. She looked at me and smiled when she realized I was ok with it being as cocky as I was about winning. Me being the nervous scardey cat I am and not show it and get it measured in front of him suggest we each get measured in private, but then we get into technicalities. He starts saying that it has to be measured hard and uniformly and suggests she judges topless, which I thought was a fare and sexy idea and agree to go first. She leads me into the next room, takes off her shirt and kisses me and tells me that I have this, her not knowing anything about dick sizes at the time, and how confident she was in me. I was pumped and thinking I had it, and was already hard from just seeing her topless. She measured me out to just over 4 1/2 in long and started to give me a hand job when I get a call on my cell. I step out to answer it, so he goes in for his turn. While outside now talking on my phone for a total of 40 minutes, she told me the next day that he walked in for his measurements and wasn't getting hard so she started to stroke it for him. He was bigger soft than I was hard but she wanted to know how big. It wasn't working and she was nervous it would give him friction burns so when he told her to put her mouth on it that she gave him her 1st blowjob and was so turned out that she forgot to measure it when he came in her mouth without telling her. When I came back in I didn't even think about how she was in the bathroom washing her mouth out. When I heard that he was a t least twice as long as I was I was shocked and humiliated. He said not to worry and as a joke called me little john all night. We drank more and I drank way too much and passed out early leaving the 2 of them to a movie that they never finished either. When they noticed how out I was he was trying to get another blowjob and she gave him one as long as he didn't tell me or his girlfriend about it. He laughed and agreed, and in the middle of getting his dick sucked got her to get up and go up to his room with him and she ended up stripping for him and loosing both her vaginal and anal virginity to him that night making a hat trick for him. The next day I woke up to her cuddled up with me on the couch and him leaving to go stay the day at his girlfriend's. Told us we need to do it more often and we went our own ways. The way I found out was that when we got home I was so horny I noticed she wasn't wearing any underwear and asked where they went. At first she said she never wore any, but I saw them early in the night so she admitted to everything and said she gave it to him as a gift. She told me this with my dick in her hand and commented how hard I got when she was telling me about it. I was embarrassed and she was excited. She still saw him and after a week he noticed that i knew. That's where it got wild, having to hide it from his girlfriend all the time that he's off fucking mine, having to buy him condoms too, and lots of buddy time.