About every other day Molly would go visit her nearly 80-year-old grandmother who still lived alone a couple of blocks away. She liked her grandma a lot. The old woman was kinda crusty and outspoken but was really neat to visit with. They developed the rapport that let Molly ask any question she wanted, knowing that she would get an honest and nonjudgmental answer.

Molly was sixteen and in that hormonally and emotionally turmoiled state that adolescent females must get through. She was uncomfortable asking her mother many of the questions which ran through her mind but grandma was cool.

“Grandma,” asked Molly, “there are some things I just don’t understand. Maybe you can help me figure them out.”

“Probably I can, young lady.” Replied the older woman who was still surprisingly physically and mentally fit. “Ask away!”

Molly began tentatively, “I’ve had a sex ed class and that left lots of questions. Because of the Internet I’ve been browsing around and finding out some things that probably kids of your age didn’t know when they were as old as me. I hear our church talk about being dedicated to the ‘right man’ in your life. But then I read on the Internet about how women are not always happy with their choices unless they had enough experience to judge who that is. What’s a girl supposed to do to make a good choice the first time instead of going through what is called a ‘trial marriage’ to learn how a dedicated relationship really works?”

Grandma smiled. “I know exactly what you’re talking about. I had one of those trial marriages the first time I was wed. It was a mistake and I figured that out the first week we were together. Even though I knew almost nothing about sex, he was terrible and I didn’t know what to do about it. My only recourse was my older sister who’d been married for a few years. She revealed to me that she was not a virgin on her wedding night and was glad of that. That flew in the face of all of the religious stuff that I had been fed, so I asked her for an explanation.”

Molly interrupted, “That’s what I’ve been thinking so please tell me more!”

“You must realize that this was back in the days before birth control was easily available and effective. The ways we tried to prevent pregnancy were primitive and often failed. You young women have it so much better than you realize. Anyway, my sister told me that I had two choices. One was to train my husband to be a satisfactory lover and the other was to leave him and have sex with other men for my satisfaction. In either case, opening my legs only for my husband would not be enough. That gave me a lot of pause for thought, considering my conservative upbringing.”

Molly was getting intensely curious, “So what did you do about that?”

“My sister allowed me to have intercourse with her husband and with two of his friends on the days when I was not likely to get pregnant. I’d found out that she enjoyed those same friends before and during their marriage. I was astounded at this breach of our religious commandment but she explained that it was with her husband’s knowledge and consent, therefore according to the Old Testament it was not adultery. Besides, those rules for women were made up by men to help control us. When I asked why he allowed it, she said that he reveled in her sexiness and their own lovemaking was enhanced. He’d only been with prostitutes before her but had thought, as he was pushing himself inside them, how many men had been where he was, and even their faking their enjoyment with him was terribly erotic. To watch her pleasured by another man for real was very stimulating and they would have sex long after the other man had left their bed.”

Grandma continued, aware of the rapt expression on her granddaughter’s face, “Following my sister’s advice, I selectively had sex with a number of men before I found one who I thought was truly compatible. I carefully probed to find out how possessive he was and when I determined that he was not at all threatened by my sexual history, I pursued him with more vigor. Finally I had to ask him his feelings about sexual fidelity. When he told me that he was currently fucking a married woman who I knew, I felt he was the man for me. As a final test I asked him to let me spend the night with his best friend and if he could accept that I would marry him. While his best friend was only a mediocre experience, it served its purpose and we were betrothed.”

Molly had to ask, “Were you faithful during your marriage?”

Grandma smiled, “It depends on your definition of ‘faithful’. Birth control came along not long after our wedding and I quickly got on it. It was the era of ‘free love’ and my smoldering lust burst into a vigorous flame. His best friend visited our bed frequently and I also spread my legs for a few others with my husband’s complete knowledge. Some of them just ‘came and went’ while others visited between my legs for a year or more. A few special ones are still my friends today, and yes, we have sex. My husband always knew, though, that he was the ultimate beneficiary of those acts and was the main man in my heart.”

The young woman was both flushed and a bit anxious. “Grandma, I appreciate you sharing that with me and I will keep it entirely to myself. Now I must decide what is right for me, and I think I am ready to begin exploring my femaleness. How do you think I should proceed?”

Grandma smiled, “I was fortunate to have a married older sister to guide me. Let’s see if there is anyone in our family who could play that role for you. I’ll think on it a bit and do some checking so let’s get together again in a week. Oh, in the meantime you need to get started on birth control. I believe that if you tell your mother that we have talked about it, she will do what’s necessary, as I did for her.”

That made Molly open her eyes wide, realizing that her mother must’ve had sex to have her and her brother. With that thought, what stories might she tell?

With a wry smile on her face, Molly’s mother listened and made the necessary arrangements for her maturing daughter. Unlike the stories that Molly had heard about some of her girlfriends’ parents pissing and moaning and getting mad when they expressed an interest in sex, her mother was very supportive and appeared to want to open a dialogue between them.

Walking to her grandmother’s house, Molly grinned as she thought of the little red riding hood story and wondered if there was a nice wolf waiting to ravish her when she arrived. Grandma greeted her at the door and they went back to the kitchen where there were tea and cookies waiting.

“I know the big question on your mind, young lady,” said Grandma. “Here is my suggestion. As with me and your mother, the tradition is to have an older and experienced man introduce you to this new realm of pleasures. I have spoken with a man who is your second cousin on my husband’s side. I believe you have met at family gatherings.”

Molly was wiggling in her chair, wondering who it might be. “Please tell me Grandma. I think I’m ready!”

Smiling, Grandma continued, “No need to be in a big rush. That will diminish the joy of the special time. It is Marty MacLean who I have selected.”

With a little squeak, Molly remarked, “Oh! He’s handsome but he’s married.”

“Yes he is but his wife, who is also my granddaughter, feels honored that he was selected. With your approval, I will call him to come and take you to dinner and a date which, if it goes as well as I hope and you are ok with it, will be followed by a night with him in one of my bedrooms. And yes, your mother knows about this so just relax and focus on what is happening.”

Molly got up and hugged her grandma, “It’s more than I expected but as I said, I believe I’m ready. I guess I would only know for sure when I get in the situation and I’m glad that I will always have the option to say no if I’m not.”

After going home to change into clothes suitable for a night out, and for once not packing night clothes to stay over with Grandma, Molly hugged her mother and returned. Grandma poured them each a glass of wine and they visited until her “date” arrived. He also hugged Grandma as well as his ‘girlfriend’ for the night as they departed for a nice restaurant.

During the dinner where they talked about family, Molly asked, “I see you’ve taken off your wedding ring.”

Marty smiled and said he’d been dispensed from his marriage for the night. His wife had been granted a similar privilege a couple of times for special reasons. That subject was not mentioned again.

Returning to Grandma’s house, they discovered she had retired for the evening but a decanter of liqueur and crystal glasses were awaiting in the bedroom they were to use. Molly lit the candles while Marty used the toilet and then it was her turn. Emerging from the bathroom, she was wearing a nearly transparent peignoir she found hanging behind the door. Grandma thought of everything!

The sheet over Marty’s lower body did drape over his already erect organ and her eyes were drawn to it like a magnet. She had seen many erections on the Internet and at least had the concept of things she could do with them prior to penetration.

Trying to get on the bed gracefully and sensually almost worked. Her knee caught in the peignoir and she tumbled down next to him. He chuckled and put his arm around her, rolling her close. He took her upper hand and placed it on the sheet over his swelling shaft. “I know you’re very curious about this thing so let’s take our time. We have all night.”