Max was 20 when he started dating 18-year-old Ashley. He was a virgin as was Ashley and they had agreed that they would keep it that way, at least for a few months. They fell in love quickly and talked about how many children they would have. She let him caress her breasts and, occasionally, rub her pussy through her panties. She returned the favor by rubbing his cock through his pants but that's as far as it went. Max was OK with that and contented himself by jacking off frequently.
Ashley's mother, Candace, was divorced and didn't have to work outside of the home due to the very nice settlement from her ex-husband as well as child support for their daughter that would last until she turned 21 or graduated from college.
Candace was a terrific cook and invited Max to share their table whenever he wanted. She knew that he was living alone and ate at fast food places most of the time. She and her daughter both enjoyed having him visit and he enjoyed spending time with them as well. Candace was almost a surrogate mother to him. Since he had never known his birth mother he grew close to her and her daughter over time. Very close to Candace eventually!
Max missed his father who was a construction worker until he was killed in an accident. He had never had "The Talk" with his father. That was when Max was sixteen and an aunt took him in until he graduated from a strict private high school run by a religious organization. Now he had a job and lived on his own. Other than the occasional exploration of a date with his fingers, he had no sexual experience and little knowledge of how sex between a man and a woman worked.
One evening he stopped by Ashley's house hoping to be invited to stay for supper. He got a surprise when Candace opened the door wearing a very thin white robe through which he could clearly see that she was wearing only white bra and panties!
"Uh, ummm, " he stammered, struggling to keep his eyes on hers, "is Ashley home?"
"Not tonight, " Candace answered, "she has an evening class and is staying with a girlfriend tonight. Come on in, I've got dinner in the oven and there's more than enough for the both of us." Her smile put him at ease, at least a little bit and he accepted her invitation. He assumed that she would excuse herself and put on something less revealing but she headed for the kitchen leaving him to close the door. She didn't seem at all uncomfortable with him seeing her so scantily clad.
Max followed Candace to the kitchen where she handed him a bottle of wine and a corkscrew. While he opened the bottle and poured two glasses she finished the meal preparation. They sat on a couple of stools at the breakfast bar and made small talk while they ate. Max carefully avoided looking directly at her breasts that could be seen bulging at the top of her bra or her long smooth legs that occasionally touched his when she twisted toward him. The closeness to a lovely and barely dressed woman was having an effect on him. He had to adjust his growing cock when he thought she wasn't looking his way.
Eventually Candace asked, "Are you uncomfortable with the way I'm dressed? I wasn't expecting company tonight."
"I'm so sorry!" Max exclaimed, "I should have called."
"You know better than that, we're practically family. You can stop by whenever you want, you're always welcome" Candace told him as she glanced pointedly at his crotch, "It's just that I can see you're aroused."
"I'm sorry, this is really embarrassing. It's just that you are so beautiful!" Max exclaimed. "Oh God, I'm practically engaged to your daughter. You must think I'm perverted!"
Candace smiled and put her hand on his thigh as she told him, "Actually I'm flattered that a young man is as obviously affected as you are by me. It's OK, don't be embarrassed, you're having a natural reaction. Do you want me to call Ashley and have her meet you somewhere to take care of that?"
"Oh no!" he quickly answered, "We don't, you know, do that...at least not yet. We're both virgins."
It was Candace's turn to be embarrassed, "I'm sorry Max. I assumed that you two were having sex. I'm not really surprised that Ashley is a virgin but I assumed that you had experience."
"I shouldn't be talking to her mom about this I guess," Max shyly told her, "but she wants to save herself for marriage or at least a formal engagement. I just assumed that she wanted me to do the same."
"Believe me, that would be a mistake," she told him in a serious voice, "the first time you two have sex is going to be awkward and messy. That sort of thing can make your wedding night far less romantic and erotic than it should be." She stood up and motioned Max toward the living room, "lets talk about it over there. I'll clean up later."
Max admired the movement of her ass under the almost sheer dressing gown as he followed her into the next room. She sat on the couch and patted the space beside her, "sit down and let me give you some advice."
Max sat down and Candace lightly rested a hand on his thigh as she told him, "My first marriage almost ended when my new husband took my virginity. The blood and my cry when the hymen was broken upset him. He wasn't able to get an erection until the next morning. Then he had an orgasm so quickly that it was all over in a minute. He wasn't able to satisfy me until a week after that. I'm not saying that it would be that way with you and my daughter but I strongly feel that the man should have experience before the wedding night."
Max was embarrassed but strangely excited by her intimate story. His erection had wilted when she called attention to it but was beginning to grow again. Her hand on his thigh, alternately gently squeezing and softly rubbing it contributed to his excitement as well.
"You should find a willing and understanding young woman and have your initial sexual experience before you get married." She continued, "I know my daughter better than anyone and she will expect you to take charge and make her first experience in bed with you a night to remember for the rest of her life."
"I don't know...she might feel betrayed if I'm not a virgin, we've talked about it."
"Have you told her that you are a virgin?" Candace asked.
"Not in so many words, she just assumed that I am, I think. We're so close that we don't always have to communicate with words, you know?"
"I do know, my daughter and I are that close of course," said Candace, "I know her better than anyone, as a woman and as her mother."
"But I don't know any other girls well enough to just ask them for sex! I can't go to a hooker, I just can't! What can I do?" Max asked her.
For almost a minute there was silence, then Candace looked into his eyes and slowly moved her hand from his thigh to the bulge in his pants and gave his cock a squeeze. Max closed his eyes and sucked in a quick breath. When he opened his eyes again Candace was smiling.
"You need an experienced woman to show you the ropes and I know one who is willing to do that for you...and for her daughter," she softly told him as she gently rubbed his cock through the fabric.
