My MILF, His mother lovingly guides him in the ways of sex, incest stories, I was always very close to my Mom. In some ways I felt like my Mom and I were the family, and my father just lived with us. When my friends got to be adolescents, they got distant from their mothers, and even hostile toward them. But I felt as close to her as ever.
I didn’t start dating until I was 18, but when I did, my Mom would always want to talk to me afterwards about how it went and give me advice. At those times, she felt more like a close female friend than a Mom. I remember how, after one of my first dates, she asked for details of how the date went and then finally said, “So? Did you kiss her?”
“No,” I said, blushing.
“Why not?” she said, giggling. “It sounds like she liked you!”
“I don’t know. I wasn’t sure if I should.”
“Ask her out again, and this time stop at the door when you’re walking her in. Don’t say anything, but just look at her and smile. If she stares back, then she wants you to lean in and kiss her.”
I followed my mother’s advice, and got my first kiss. She hugged me happily when I told her about it that night.
I soon had my first girlfriend. After she and I had started necking, my mother asked, “Have you touched her boobs yet?”
“Mom!” I protested.
“Oh come on!” she giggled. “Do you think girls don’t like that too?”
Suddenly, I had an image of my Mom when she was my age, getting felt up by a boy. The thought was disturbing, but I couldn’t stop thinking about it.
“How do I know if she wants it?” I asked.
My Mom moved closer to me on the couch. “When you’re kissing her, put your hand on her arm like this. Then slowly move it up toward her neck.” She acted it out as she described it. Suddenly her hand didn’t feel like a Mom’s hand. It seemed so tiny and soft. “Then caress her neck with your fingertips and move it slowly down toward her chest.” I felt my mother’s hand slide down. “If she doesn’t want it, she’ll shift her arm to block it. But if she doesn’t block it….” My mother just smiled, her eyes bright.
On my next date, I not only petted for the first time, but my girlfriend even rubbed me through my pants until I came. Of course, my Mom wanted to hear about all of it afterwards, but I was shy and didn’t want to tell. She kept insisting and finally started to tickle me until I told her everything. But her face froze when I said that I had orgasmed in my pants.
“Are you mad at me for messing up my pants?” I said anxiously.
She smiled, putting me back at ease. “Oh, no, no, sweetie. It’s just that…you’re growing up so fast.” She studied me for a moment and said, “You’d better change out of those wet shorts, though.” I headed to my room to change. I was surprised when I saw Mom had followed me in.
“Mom, I need to change.”
“I know. Just take them off and hand them to me.”
“Mom! I’m not going to change in front of you!”
She laughed. “Don’t be silly I used to bathe you, for goodness sakes!”
“But I’m not a little baby anymore.”
She looked a little pouty. It was strange to see that expression on her face. Mothers don’t pout. They get angry or disappointed or sad, but they don’t pout.