Becca was a friendly and beautiful milf at around 36 years old: Brown hair/eyes and olive skinned, quite tall at 6′, 156 pounds, very curvy, and with unbelievably big but 38G tits. She used to be my (19m) babysitter a while ago. I remember how misbehaving enough would earn me a trip over her knee, and I’d eventually get spanked on my bare bottom. Sometimes she would start off doing it on my pants and underwear, times she’d skip straight to yanking my clothes off. Generally she was a very friendly, caring, almost motherly babysitter, but she sure knew how to be strict when handing out a punishment. That being said, she would give a bit of aftercare almost every time.
By the time I was hitting puberty, I noticed the spankings became a turn on in a sense. The threat and anticipation of them would make me rock hard, though that boner went away in the middle of the spanking when its intensity became hard enough. But my cock shot right back up when it cooled down, especially as I felt the after-spanking warmth on my behind and the intimacy of being half naked in front of Becca. I couldn’t help but purposely misbehave sometimes, Becca’s spankings were such a turn on. I even got her to spank me harder at times by saying calling her spankings “a joke.” After every spanking I went up to masturbate thinking about Becca. Unfortunately, it all stopped once my Mom decided I was “old enough to watch myself.” I surely couldn’t sound like a child so I reluctantly had to accept.