Grandpa's Guide to Women Pt. 08

Your response to Grandpa’s Guide to Girls was so flattering that it motivated me to write this sequel. You voted your approval and made very kind comments about the story of Grandpa Frank helping young Ben woo his first girlfriend.

You need to know why I placed this sequel in the “first-time” category. Ben is not a virgin when he arrives at college, but every sex scene in this 10-part sequel has at least one character having at least one “first-time” experience. Oral. Bondage. Anal. Roleplay. Reluctance. Facials. Threesomes. New partners. The recurring theme is the gradual surrender of diverse kinds of innocence.

As you know, many stories in Literotica defy categorization. It’s almost impossible to give readers all the information they deserve while deciding what stories to read. If you’re looking for a tale of young lovers having erotic experiences for the first time, you’ll find it in Grandpa’s Guide to Women. Just know that these characters surrendered their virginity before this story begins.

Part 8 shows Ben doing his best to give Julie a new experience.

All characters are adults over 18.

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Sonya did some reflection and came up with several suggestions for role-playing games. We acted out fantasies about her being an older, predatory woman with a young, innocent boy. She suggested other scenarios that were just as enjoyable. We kept coming back to Sonya’s long-term interest in having sex with another woman, but it’s hard to find believable ways for me to pretend I’m a girl who coincidentally has a cock.

Edibles helped. So did vodka.

I’d always been careful to avoid telling Sonya too many details about my relationship with Julie, and I kept quiet about Sonya with Julie. I didn’t want to violate anyone’s confidence, and I wanted both women to know I respected their privacy. I hate it when guys tell other people about sexual things they do with their girlfriends. I don’t ever want to be that kind of guy.

But Sonya and I were talking about having a threesome with Julie, and there was no way to do that without discussing some very personal issues. “I’ve had a lot of fun learning about your fantasies, Sonya,” I said one day. “I’ve particularly enjoyed learning that you’ve got such a strong dominant streak. It’s very erotic.”

“Does that mean it’s OK if I spank you sometime?” she asked, grinning.

“Just don’t leave any marks that would be hard to explain in the locker room,” I said.

“I need to tell you that I’ve talked to Julie about having a threesome, and the idea scares her a little. Sonya, if we’re going to do this, you need to know some things about Julie that are very private. I’ll need to tell Julie some private things about you.”

“You can tell her whatever you want,” Sonya said. “I’m not shy. If we’re going to have sex, it makes sense that we will have to be very open with each other. What kind of things do you want to tell her about me?”

“Well, I need to say that you’re attracted to girls,” I said.

She laughed. “Oh. Right. That. OK, I admit that’s pretty relevant information. I guess she needs to know that the woman who wants a threesome with her happens to like the ladies. While you’re on the topic, feel free to tell her that I think she’s hot.”

“Really?” I asked.

“Of course. Julie is hot as hell. God, I’d love to get my hands on her. Every time I see her ass I want to give it a squeeze. Those big boobs are amazing. I’m particularly fond of the gray leggings she wears sometimes. Very flattering. Be sure to share that information.

“Since you have to tell her I like girls, you have to tell me about Julie. Does she like girls?”

“Definitely. Unlike you, she has absolutely no experience with women. But the idea arouses her,” I said.

“Good to know,” Sonya replied.

“There’s something about Julie that I would never tell anyone, but I need to tell you. I’m sure I can trust you to never betray her confidence. You need to know that Julie is submissive. She’s a hard-core sub. Loves being told what to do.”

“Oooo! Kinky!” Sonya said.

“The relevant fact here is that you’ve got a very pronounced dominant streak,” I told her. “If you and I have a threesome with Julie, she’s going to want both of us to dominate her.”

“This just gets better and better,” Sonya said. “I like this plan. Happy to be part of it.”

“I just thought we should discuss this before I tell Julie it’s going to happen,” I said.

“I’m guessing you haven’t told her that I’m the woman who wants to do this, right?”

“That’s right. She doesn’t know it’s you. I’ll make sure she knows in advance.”

“You need to do that,” Sonya said. “It’s very possible that Julie would be willing to have a threesome with anybody but me. She may still feel bad that we started dating during that time you refused to have sex with her.”

“I’ve wondered about that,” I said. “But you’re terrific. I’ve never told her anything remotely negative about you. I’ll be sure to tell her you’re the woman who wants to be with us.”

The next day I had particularly enjoyable sex with Julie. By now I’m sure you understand that I get more satisfaction from making a woman climax than I get from making myself climax. When things go particularly well – as they did that night – I can make Julie cum three times, and one of those orgasms will be strong enough to detect on earthquake monitors. In retrospect, it’s not too surprising that people are gossiping about my sex life. Julie and Sonya are both delightfully loud lovers, so there’s plenty of material to gossip about.

“We need to discuss something, young lady,” I said that night.

“What do we need to discuss, sir?” Julie asked.

“I’ve arranged for a woman to have a threesome with you. With us. You’re ready to do that, right?”

Julie had a conflicted look on her face. “I guess. It’s scary. But every time you make me do something I’m reluctant about at first, I end up loving it. I guess I should just do it and see if I like it, sir.”

“That’s a very good attitude to have, little girl. You know I think you’re the sexiest woman alive. Your willingness to share your fantasies is a big part of the reason. Thank you.”

“You’re welcome, sir,” she said.

“There are a few things you need to know,” I said. “You need to know that the woman I have in mind has a very strong attraction to girls in general, and you in particular.”

“Me? She’s attracted to me?” Julie said.

“Yes. She thinks you’re hot. She’s anxious to have sex with you. She says she thinks that the gray leggings you wear sometimes are particularly flattering. She likes your ass. She also likes you as a person. She hasn’t had sex with a woman, and she would love it if you could take her virginity.”

Julie’s eyes got big. “Wow,” she said. “Things just got real. Sir, do I know her?”

“I think so,” I said. “It’s Sonya. She said she was very sad about your trouble, and she’s glad things have gotten so much better. She’s been hoping for a chance to have sex with a woman, and she’d love for it to be you.”

Julie looked sad.

“I’m not sure what I think about that,” she said. “I used to feel very jealous of her. I used to hate having to share you with her. I’m conflicted about Sonya. It might be weird trying to be intimate with her.”

“When you felt bad about Sonya, what bothered you?” I asked.

“God. Everything,” Julie said. “I fucked up so much of my life the night I got drunk. The worst thing was I thought I’d lost you. I couldn’t believe I’d been so stupid. It was very threatening when you immediately started dating Sonya. I thought that meant our relationship was over.

“Sir, I’m very glad that you were willing to keep seeing me. I was desperate. I was so desperate that I was willing to let you date other women. I used to hate knowing you were seeing Sonya. I always hoped I’d have you for myself someday. I hoped that if I was the best possible girlfriend, you’d eventually stop seeing her. I don’t think about that much anymore, but it bothered me for a long time.”

Julie looked miserable. “When we got back together, I felt like I was on probation with you. I did things I wouldn’t have done before. I never let a man cum in my mouth before you made me do that. I never let a man near my ass. I never would have let you tie me up if I thought I had a choice. All that happened because I was afraid you’d dump me if I didn’t give you whatever kind of sex you wanted.”

“I’m sorry you felt that way,” I said. “I never meant to hurt your feelings. I wasn’t trying to be coercive.”

“You didn’t hurt my feelings, sir,” Julie said. “You were great. You helped me begin feeling better about myself. I’m glad you forced me to do all those kinky things. I learned a lot about what excites me, sir. I guess I’m a pretty lousy feminist because I love letting you do so many dirty things to me.”

“I think you’re a great feminist, young lady,” I said. “You are exploring your sexuality without letting guilt stop you. That’s what feminists are supposed to do.”

Julie laughed. “That sounds like something you’d hear from a man who wants to have a threesome, sir!”

“Ouch!” I said. I pulled Julie closer. “It’s true that I want to have a threesome with you. I’m sure we’ll both enjoy it. To me, the only question is whether it’s a good idea for the other woman to be Sonya. If you really hate the idea, we won’t do it. But it would please me if you gave her a try.”

She smiled. “We already know how much I enjoy pleasing you, sir,” Julie said. “Fine. Tell her it’s OK. Tell her I’m glad she likes me. Tell her I think she’s cute, too. Oh God, this is actually going to happen, isn’t it?”

“Yes it is, young lady. Yes it is.”

With the conversation over, it was time for us to have sex. I felt I needed to do something special for Julie. It needed to be something we’d never done before. I’d spent some time paging through the book Grandpa gave me, The Complete Idiot’s Guide to Kink, and I found an idea I thought she’d enjoy. Julie liked to be surprised, and I was certain this was something she wouldn’t expect.

Things started as they always did.