I grew up in a non-nudist home, but family nudity was not an issue for us. I bathed with one of my parents or older sister until I was 8 y/o. My parents were (still are) nude sleepers, so seeing one or both naked in the mornings wasn't unusual. Like my dad, I hung out in my underwear most evenings after bathing.
My parents separated when I was 10. When I was 12, my older sister married before my parents divorced. That left just Mom and me at home.
I was still in middle school when I got into sports. My dad took me swimming at his club once a month and encouraged me to sign up for sports. I joined the local YMCA kids' swim and soccer teams at school. My soccer coach insisted we wear jockstraps when practicing soccer. Since we practiced five days a week after school, I did what some other boys did: I switched from wearing underwear to a jockstrap instead.
Mom never complained to me about my near nudity after showering at home. Throughout my High School years, I often spent most evenings and weekends in my jockstrap and nothing else, only dressing if going out or if we had company.
When I was 20 and in college, I discovered nudism, and after talking to my parents about my desire to live a nude lifestyle, my dad agreed but I was living with my mother; he said only if she agreed. Mom did agree but with certain restrictions, to which I agreed.
I admit being naked at first was a bit weird. Before, I never felt naked because my genitals were covered. I know it's weird because, to be honest, a jockstrap doesn't cover much. Your butt is exposed, and the pouch didn't do much covering of your pubic hair. But in my mind, I was not naked, and now that I was, it felt weird not only because I was naked but because Mom was always looking at me.
I had to wake up early every morning to catch the 8:30 bus. Most mornings, I woke up on my own, but now and then, I overslept, and Mom would come to wake me up.
It was one of those mornings that I overslept that it happened. I woke up realizing I had overslept, jumped out of bed, and headed to the bathroom.
As soon as I stepped into the hallway, I saw Mom approaching me. We both stopped dead in our tracks. I stood there naked, sporting my usual morning woody. Mom stared as I tried unsuccessfully to cover my erection. Mom recovered first and said, "Ah, I see you're up. Better hurry, or you'll miss your bus." She then turned around and went back to the kitchen. At breakfast, neither of us said anything.
About a week later, it happened again. Only this time, I didn't bother trying to cover up. At breakfast, I started apologizing, but Mom stopped me before I got two words out. She told me she understood boys/men often wake up with an erection. She said Dad always did and that she didn't have any issues seeing me with one.
After a few more morning run-ins, I felt comfortable enough to joke about it with her, and over time, I started going to the kitchen sporting my morning woody and even chatting with Mom before going to the bathroom. Mom encouraged me, not with words but by not making my erections an issue. On weekends, we would chat in the kitchen long enough that my erections went away. Then one evening we were watching a movie on TV. We were sitting next to each other on the sofa when a very graphic sex scene came on, and I quickly went from limp to a full-blown erection. Mom was quick to respond. She said, "I see you liked that."
I didn't know what to say or do. I just sat there naked, sporting my boner next to her. After what seemed like hours, my dick finally deflated. But by then, the movie was over. I excused myself and went to bed.
That was the first time Mom had seen me get an erection. Before she had only seen me already boned. I already knew Mom didn't mind seeing me with an erection, but now I knew she didn't mind seeing me get one. When that happened, I had just turned 21, and I wasn't embarrassed or felt it was wrong.
I had seen Mom naked many times when I was younger, but since the divorce, I saw her naked less and less, and more often than not, if I did see her, she was covered except for her breasts. I didn't think it unusual because our schedules were so different, and unlike me, Mom wasn't a nudist.
I had no girlfriend, so my sex life mainly consisted of jacking off, which I did in the privacy of my room. After chatting with Mom on some weekends, I'd excuse myself, go to my room, and masturbate. It wasn't a secret that I masturbated.
I can't recall exactly what was going on; we were on the patio chatting, and I had an erection. I excused myself, and before I left, Mom blurted out, "Oh! I know what you're running off to do. Don't be silly. Just do it here and get over it."
That was the first time I masturbated with Mom watching.
Since then, I have masturbated for her many times. Even when I was living with my GF, I'd come home and visit with mom and masturbate for her.
Just before the Covid epidemic happened, I broke up with my GF, and due to financial circumstances, I moved back in with Mom. I'm 30 and still living with Mom. I'm almost always naked and masturbate 3 to 4 times daily with Mom present.
She never tires of watching me.
