When I was 20 years old and living with my Mom (I was a freshman in college), my best friend was Jakub, 19 years old, who lived with his mother in a house near me. Jakub’s mom, a widow, was very attractive with a sassy, upbeat attitude. She would be a prime MILF in today’s parlance, but the acronym was not known at the time.
They had a very nice pool and a tall privacy fence, and would make it available to her son’s soccer teammates (I was one) after practice. Jakub’s mom, a widow, was Eastern European, and had a view that it was fine for men to swim nude. “Bareskin” she called it, with a sly wink.
I was the only one who swam nude with Jakub on a consistent basis. The teammates would occasionally come by for a team swim, but of course we all had our Speedos on then. As time went on, I spent more and more time at Jakub’s house and pool, instead of hanging out with our other teammates. We went from skinny dipping in the pool to being comfortably nude in the house, with Jakub’s mom (Mrs. L) going about her business as if nothing unusual was happening.
He and I hung pictures for her one afternoon, both of us naked. Mrs. L was full of “advice” about local women and sex. Later, Jakub asked me if I minded his mom’s behavior.
I replied, “Your mother is really fun, and I really enjoy being naked. It is very liberating, and super-relaxing to not have to hide our bodies or hold back anything in our conversations – she is much like Dr. Ruth, and has the wit and accent to match.”
Jakub said he was afraid that his mom was a bit over the top for me, but he was glad that I adapted well to it. He felt at ease not having to worry about clothes in the house, and we all know every man prefers to skinny-dip.
But…my mother was less than pleased! Mrs. L ran into her shopping one day and told my mother that she liked me and I was developing into a nice young man. My mother asked me if Mrs. L saw me naked. I nonchalantly said Jakub and I skinny-dipped at the pool. What my mother didn’t know was how much time I was nude around her in her house, nor did she know about the Polaroids Mrs. L took of Jakub and me. Nor, that one day after swimming she encouraged me to masturbate into a cup she provided me, in her own living room, to “get rid of it” before I went home.
When we graduated, Jakub got a job about 320 miles away, and I joined the military. My first time on leave was October of the following year and I went home. I decided to visit Mrs. L.
She was surprised and pleased to see me. I told her I knew Jakub wasn’t there, but I wanted to say “Hi!”. She asked me to come in.
Well, it wasn’t ten minutes that she told me that I could “go bareskin” if I was more comfortable. “You are always bareskin here so it is ok if you are now.” I didn’t hesitate. I stripped out of my clothes, folded them, and sat on the sofa. She started to talk about how “nicely” I was becoming a man. She asked me about any ladyfriends and told me she missed having Jakub and me around the house in the summer. “I like having the two of you here without clothes. It is good to look at. I could compare you.” I told her that her attitude and praise really helped my confidence. She told me, “I saw Jakub bareskin all the time. When you were there, I could see who was getting bigger or had more muscles.” She made me a sandwich and continued talking about women, and what I should do. Of course, I started to get hard and stayed that way.
“Allan, you always get hard quick. It used to make you embarrassed.”
I told her that it didn’t any more. She asked me to stay there and she left and returned with the pictures she took of her son and me. “Remember this?” I told her I did. There was a full frontal shot of the two of us with an arm around each other’s shoulder. “You got hard after this.” she laughed. Yes, I told her and I reminded her of how I left for the bathroom to take care of it.
So, lots of flirting continued. I enjoyed being the focus of her afternoon. She sat next to me after I suggested I should probably go. She told me she knew I wouldn’t get back this way very often.
“Don’t tell anyone,” she said. She started to rub me up and down my body and finally got on her knees in front of me. What followed was her kissing my cock and stroking me. She stood up and stripped to her underwear. “This is as far as I go,” she said. She led me to her bedroom. We got on the bed and she continued stroking my now rock-hard cock. I managed to get my hands in her panties. I soon came, making a rope of cum across her. I kissed her and told her I’d always been in love with her.
“I know,” she said. I showered with her watching me. I dressed. I saw her the next summer when I came to visit Jakub who was home from his job. Both of us were swimming naked. Mrs. L watched us from her chaise lounge, and this time she was topless.