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.
I whispered: "Mom, I need to ask you something very private and you have to promise not to tell anyone. Can we go downstairs away from where everyone else is before I talk to you?
"Stevee, is there something wrong" She always called me Stevee when she was worried about something."
"No, I just want to talk to you alone. It won't take long Mom."
So we went downstairs and I asked her to sit on the couch. I sat on the coffee table right across from the couch. The coffee table and couch were pretty close to each other so our knees were almost touching.
"Mom, I want to ask you something and please don't be upset with me."
"Stevee, tell me what's wrong"
"Mom, there's nothing wrong, I just don't know what to do in case something happens between Judy and me. You know, uh...."
"What do you mean something happens? If what you mean is what I think you mean, well then let nature take it course. But make sure that you're careful and you use protection. You're too young to start having children and she's too young to have children.
With that she reached across to me to hug me to her, "Come here Stevee". I had to lean forward and sort of fell onto her. We stayed like that for a minute or so with my head turned sideways across her chest, my knees on the floor in front of her with one knee between her knees. I could smell her perfume and could feel her heart beating. I was hugging her about as tight as I could. She was ruffling my hair and sort of rocking side to side like she used to do when I was very young.
Mom grabbed my head and turned me so that I was looking right at her, "Stevee, are you feeling better now?"
I was feeling pretty amazing things right then; love for my Mom, the feeling of being so close to her, my chin being right near her breasts. I remember that I had an erection at that point.
"I feel wonderful Mom."
There was a long pause here and then I risked everything and took the plunge.
"Mom, can I have a practice kiss with you? I've never kissed..."
"Stevee! What in the world are you talking about?"
"Mom, I'm sorry, I didn't mean anything. I just was wondering what it would be like to kiss and I don't want to mess it up with Judy."
I was now supporting my upper half with my hands on either side of her. Although we were not touching anymore, we were still quite close. Mom was looking me right in the eyes with what I think was a questioning and unsettled look.
"Steven, do you know anything about kissing? Have you ever kissed anyone?"
"Mom, I've never kissed anyone before but I've read about it. I read that you can actually touch tongues with the person that you kiss but I don't understand how to do that. It sort of seems like an odd thing to do."
"It not odd at all Steven. In fact, if you kiss with someone that knows how and that you care about, it's an amazing and moving experience. Listen Steven, Let me go to sleep now and I'll think about this. Don't worry about your father, I'll not tell him anything about this. We will talk about this again."
With that, she made to stand up so she and I stood up together. I don't think that she had any understand of my state at that time so she gave me a big hug. I felt my erection touch her; I don't know where it touched her but I cannot imagine that she didn't feel it, even with the terrycloth robe. She gave me a quick kiss on the lips and headed upstairs to bed.
Of course, I couldn't sleep before I took care of my erection.
To be continued.