I was 18 and very, very shy around almost any female except for my relatives. I was also very horny and desperate to experience sex but I had no idea how to even ask a girl out without it being very awkward. I know that my mother noticed and tried to help me out as far as a mother could.
"Steven, why don't you ask Judith out? She comes over all the time to borrow things that I don't think that she or her mother needs. I think that she just wants you to ask her out."
"Mom, I don't think so" But I smiled and imagined what it'd be like to go out with Judy. But I knew that I'd get all tongue tied and wouldn't begin to ask her out. "She's just too beautiful and I don't even know how to ask her.
"Steven, I think that you're handsome, maybe a little shy and you just need practice to see that there's nothing to it. Why don't you practice asking me out?"
"Oh sure Mom, why don't we go make out in the living room before Dad gets home?"
"Steven! Listen to me, I'm not talking about making out, I'm talking about learning how to be at ease with someone that you want to be with. You've got to start somewhere if you want to get to know her."
"Mom, ok; what do I say? How do I ask her out?
Well we went on from that start to me asking Mom if she'd like to go out for dinner and a movie. I was talking to Mom but imagining that it was Judy that I was talking to. But at some point in the conversation I started imagining that Mom might actually like to go out with me. We started having this fun chit chat just like she was my date; she laughed when I said something and looked me in the eyes in a way that just moved me to want to look back only at her. Our pretending of my asking her out was amazing and fun and exciting.
Dad came home and the four of us had dinner and we all chipped in and got the kitchen cleaned up. Afterwards, he and I talked about a few things that I cannot even remember and then Mom told him that I was going to ask Judith out tomorrow. That was pretty embarrassing but then she told him that I'd been practicing with her and was now great at starting a conversation and small talk and then asking about going out. Dad laughed at that and said that Mom did make things easy and that I was lucky to have her be my guide.
Normally, I'd be really mad and very embarrassed that she'd told Dad about her helping me and that I needed her help. But I felt a different kind of closeness to her and it didn't seem to be such a big deal. In fact, I was sort of proud of the way that we had talked and that I had kept a good conversation going. She certainly seemed proud of me and proud of herself for getting me a little further along the road to independence.
That night, several hours after we all had gone to bed, I couldn't sleep. So I went over to my parent's door, knocked and asked if I could talk to Mom. She said that she'd be right out. She came out wearing a big bulky robe and was tying the sash as she came into the hallway. Dad asked what was wrong and Mom told him that everything was fine and that she'd talk to me and would be back soon.
