Mom was twenty when she had me. I was actually born out of wedlock as they said. My Dad had been planning to marry her but Pearl Harbor happened and he, like a thousand other guys, enlisted right away. She was afraid she'd never see him again and they had sex before he caught the train. As luck would have it, she got pregnant and he died on the USS Lexington. Her very religious family was angry and said she had shamed them. She told them and their religion off and left that small town. She found her way to Kansas City and got a job working as an operator. A lot of women were joining the military or moving to take factory jobs and they needed a switchboard operator. She stayed there doing that job for thirty years. She took early retirement in 1972. Seems she was smart enough to invest and was making a killing at it.
Anyway, my story is that I was always bullied at school. I was skinny and red-headed with freckles and glasses. But Mom treated me like a treasure. She loved and cared for me like I was the most important person in the world. I don't remember many men in her life, I believe she did date for a while, but she did have a few very close girlfriends. Some of them stayed late into the night. Some of them stayed overnight. One stayed for a week once when Mom was hospitalized. But I knew nothing about sex, let alone lesbianism. Hell, no one talked about it at all.
There was a girl in High School I found I liked... a lot. She was Virginia Maycomb and she was a very pretty brunette. I found myself tutoring her in math. She was friendly when we were alone but standoffish at school. I realized she was unwilling to be seen with me. You know, peer pressure. I was the outcast, the unclean.
This of course dawned on me just when I had the nerve to ask her out. It was Thursday, my eighteenth birthday and I had asked her to go out. Just for burgers and shakes. Instead, I was crushed. I sat in my room and cried. Mom found me and sat on my bed talking to me for a long time. She left the room for a bit and then came back in. She stood facing me with her fists on her hips.
"Okay Lester," she said in that matter-of-fact, no-nonsense voice. "Let's deal with this. Head on, just like we've dealt with everything else that has come our way."
"Huh?"
"Look, I see you're pining for a girl who won't be seen with you. Fine. You don't need shallow friends. The way I see it, your hormones got stirred up, then abandoned. I know exactly how that feels. So, the real problem is that you're eighteen now and needing to sow your oats. Well mister, as much as I can sympathize with the yearning, I can't have you knocking up some girl. Look what happened to me."
"But-"
"But nothing! I know it's 1960 and times have changed, but not that much. Besides, I want you to go to college and if you get a girl pregnant and have to get married, that won't happen. So we're left with the fact that you need sex. Safe sex. That means a woman who can't get pregnant."
"What? You want me to have sex?"
"Of course! God love you child, but sex is great! Or at least it can be. God gave it to us and with the right person, it is the most amazing thing you'll ever experience. But listen, to get there, well it takes practice. The first time you have sex is not going to be so great. But once you learn, it will get better and better. And as I see it, as your parent, it is my responsibility to teach you and prepare you for life as an adult. Now, this girl is stupid to let other people influence her opinion of you. But I know for a fact that it's her loss. So let's get on with lesson one, kissing."
"Uh..."
Before I could mentally process what she was saying, Mom stepped up to me and put her arms around my neck. She was almost as tall as me in her heels and suddenly I was kissing her full on the lips. Or rather, she was kissing me because I didn't do much of anything.
"Oh lord, Lester! That won't do. That won't do at all!" she said. "Look, close your eyes, think about that girl and kiss me."
I tried.
"Well, that's a little better..." Mom sighed. "I know you can do better, much better. You're just nervous."
"Of course I'm nervous!" I said, "You're my Mom! I'm not supposed to be kissing you!"
"Oh, honey!" Mom replied, "Is that what upsets you? Okay, listen close. I am your Mother. I am also your friend, right? And friends help each other. Now, I intend to help you." She backed up a couple of steps and rested her chin on her knuckles as she thought.
"Well, I'm guessing that you have a lot of built-up sexual tension. I don't suppose you've ever had a release, a sexual release have you?"
"What?"
"Oh Lester, do you masturbate?"
"Uh..."
"Do you play with yourself?"
"S-Sometimes..."
"To ejaculation?"
"What? No!"
"Oh dear! Well, that could be part of the problem... You have no way to relieve the tension. I guess that's my fault for not teaching you how. I suppose I just assumed you'd figure it out. Well then, let's fix that right now. Drop your pants. No. Strip off all of your clothes. Let's see what you look like. Besides you need to get used to getting naked. Sex is better naked."
Mom clapped her hands once, loudly. "Go on, strip!"
I was so accustomed to obeying her that I didn't stop to think about it. A moment later I was standing there naked as she looked me over. Only then did I feel awkward. I hadn't been naked in front of her in seven or eight years. I automatically covered my groin with both hands.
Mom sighed. "My, you have grown up. When did that happen? You are healthy and normal if a bit skinny... I need to put a few pounds on you. But there is nothing unsightly or unpleasant about you. In fact, I think you look quite nice."
She stepped closer and moved my hands.
"Oh my!" she said smiling. "You are no longer my little man. You, my son, are grown."
She touched my penis and it twitched in response. I felt it growing and swelling in her hand. No one had ever touched it, held it before. I watched stunned as my Mom got down on her knees in front of me and examined my growing organ. Her touch was delicate and yet unavoidably arousing. She examined it closely, gently lifting and turning it, softly caressing it and my balls.
"Very nice.Very nice indeed," she said as she stroked it. Her hands felt so good that I was quickly stiff and hard.
"I'd say it's a good nine inches. You should be proud. It's straight, long, and thick. This," she said still slowly stroking it, "is going to make women very happy. Well, once you learn how to use it."
Mom continued to stroke it slowly and looked up at me. Our eyes locked and I found myself wondering why I'd never noticed the green flecks in her hazel eyes before. She puckered her lips and kissed the tip. I felt something jolt me. Her mouth opened and she slid it in. Her tongue ran a few circles around my knob then she took it deeper. I felt her tongue on the bottom of the shaft and then she started stroking faster and squeezing tighter. It felt incredible and exhilarating.
"Ohhhhh..." I moaned.
Mom popped it out of her mouth and smiled.
"Feels good, doesn't it?" she said as she continued to stroke a little faster. "You can do this whenever you feel the need... or if you want help, you can ask me."
I felt a sudden warm rush and what felt like an internal explosion of ecstasy throughout my body as I had my first orgasm. My load blew, sending rope after rope of thick spunk shooting out. The first spurt caught Mom in the face as she was talking. The next several splattered her neck and dress.
I was shocked and stared as Mom simply smiled up at me. She licked her lips, wiped her face and licked her fingers, and swallowed.
"Oh my! Lester! That was impressive!" she said as she milked the last drops from my still twitching organ. She licked them up and looked at her dress.
"My goodness what a huge load!" She said as she stood up.
"What happened?" I asked. I felt weak and yet wonderful.
Mom smiled. "You climaxed, you orgasmed, silly. That's what you do when your cock is stimulated enough by sex or in this case masturbation. This..." she said gesturing at the white ropes covering her dress, "is your semen or spunk. It carries the sperm you make. If you ejaculate like this inside a girl it will likely make her pregnant."
Of course, it all made sense. All the trivial bits of sexual information I had acquired added up and I finally grasped the concept and saw the big picture, or at least most of it.
"So I have to get my..."
"Cock..." Mom said.
"Inside her? How?"
Mom's eyebrows rose. "You don't know?"
I just shook my head. "I'm not sure."
"Well this dress is soaked and I need to get it off," she said as she unzipped and stepped out of it. She stood there in front of me and stripped. I could recall seeing her bare breasts before as a small child but now as she dropped her bra I couldn't help but stare.
Her breasts were full and round and still quite firm (she was only 38) and I would later check her bra to see the tag was 32C. Her areola were a pinkish-tan and her nipples were reddish-pink like the erasers on pencils. I saw she was watching me and she smiled.
"I suppose you've never seen a naked woman before," she said as she stripped off her panties and kicked off her shoes.
"N-No."
"Well here it is," she said and slowly turned in a circle before me. When she was facing me again she stepped closer and pushed me back to the bed.
"Sit," she commanded and I did.
She stepped closer and put her right leg on the bed, her crotch in front of my face.
"This is my vulva which guards my vagina, that's the opening which leads to the womb, and that's where you put your cock during sex. Here, give me your hand."