Grandpa's Guide to Women Pt. 05

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 on 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 5 shows how Ben follows Grandpa Frank's advice about ways to provide women with exciting new experiences that will make them want to keep him in their lives.

All characters are adults over 18.

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Another one of Grandpa Frank's predictions came true over the next few weeks. He told me that Julie would want to give me so much sex that I wouldn't have enough time or energy left for Sonya. She spent night after night in my dorm room. We had lively, energetic sex, which always included a particularly exciting session in the morning before she had to go back to her sorority. It wasn't ever going to deplete me enough to get me to stay away from Sonya, but Julie was trying her best.

My roommates couldn't believe it. Neither of them had girlfriends yet, and they were trying hard not to act jealous. Julie spent most nights in my room, and on almost all the others I spent the night in Sonya's room. I can't blame them for feeling jealous. If I was in their position, I would have been jealous too.

"Things are going great, Grandpa," I said during one of my regular phone calls where I gave Grandpa Frank updates. I told him his prediction about Julie's sorority sisters flirting with me had been accurate. So far, three of them had acted in ways that made it obvious they wanted me to ask them out. I'd followed Grandpa's advice and resisted, and I'm certain that was the right choice.

"Julie and I are doing fine," I said, explaining that we were continuing to do roleplaying that featured me as a Dom and her as my Sub. We discovered she loved being spanked. I have no idea why she likes it so much, but I'm happy to slap her round, shapely ass anytime she wants.

"Sonya and I have a more normal relationship," I said. "It reminds me of the way it was with me and Beth. I think I'm beginning to catch feelings for her, although she doesn't feel that way about me. She sees me as a nice guy who's fun to be around and who tries to satisfy her in bed. I'm not sure what to do next. I'm pretty certain she wouldn't be interested in the kind of things that excite Julie."

"But you don't really know, do you?" Grandpa Frank asked.

"No. No, I don't. There's no problem. We have lots of fun in bed. It's very satisfying. But it's been a while since I've introduced her to anything new. I keep thinking of how you've told me that it's my job to think of ways to give girls new experiences. I'm not doing that job very well with Sonya. We just have ordinary sex over and over."

"There are lots of things you can do about that," Grandpa said.

"The first is to just ask her. Ask Sonya to tell you about her sexual fantasies. She's known you long enough to know she can trust you. Offer to help her act out her fantasies. Most women like men who'll do that.

"Another idea is to see if she likes porn. Ask her to show you some porn that turns her on. That ought to give you some insights. I know most of you young people think of sex videos when you think of porn, but a lot of girls prefer erotic fiction. Since Sonya is such a smart woman, she might have a book of erotica she likes. Ask her to show you her favorite story. You might be surprised. Sonya must have interests you know nothing about."

That night Sonya invited me over to her sorority to watch a showing of the classic comedy Animal House. It's a very old film, but I enjoyed it, and so did the others. I was surprised when I discovered I was the only male invited to the party. That made me feel good. Special.

Afterward we went up to Sonya's room to have sex. I tried something I learned as I was looking for ways to meet Julie's need for submission. The book Grandpa gave me said that a good way to introduce a woman to bondage is to pin her arms over her head as you have sex. I hoped that would give me a clue into whether Sonya would enjoy being restrained.

I gripped her wrists and held her arms firmly. She seemed to like it, but not nearly as much as Julie. Julie enjoyed it so much I went out the next day and bought some silk bondage rope from an off-campus sex shop.

As always, I managed to give Sonya two orgasms before I allowed myself to climax. She fell asleep with a smile on her face. There was absolutely nothing wrong with our sex life, but I felt sure I could do better. So when she woke up I followed Grandpa's advice, and asked if Sonya had an sex fantasies she'd care to discuss.

"I have lots of dirty little daydreams, but none of them are particularly stimulating," she said. "I doubt that you'd find any of them to be very entertaining."

"I'm not looking to be entertained," I said. "I want to know more about what arouses you. I'm very happy with the sex we have, but I want to know if there's some fantasy I can help you make real. If there's any role playing you'd enjoy, just ask. I'm happy to do anything that doesn't involve instruments of torture."

Sonya laughed. "Yeah, I'm not turned on by torture. We're on the same page there," she said.

"Ben, I have a fantasy that's kind of embarrassing. I'm not sure I'm comfortable telling you about it."

"Sonya, you know you can trust me," I said. "Just tell me what it is. I want to know what makes you tick."

She rolled her eyes. "I'm going to regret this," she said.

"No, you won't," I said.

"Ok. You asked for it," she said.

Sonya described an erotic story about an inexperienced adolescent man who was obsessively interested in sex, but knew nothing about it. He had fantasies about a middle-aged woman who lived next door. He found her to be very attractive, but never imagined she'd have any interest in a high school kid like him. Still, he kept finding ways to hang around her house while she was there, and the woman eventually noticed that the boy always had a boner whenever he was near her.

The woman thought it would be fun to relieve this young man of his virginity, but she knew he was too frightened to let it happen. She lured him inside and "forced" him to have sex. After that first time, they had sex repeatedly until she moved to another town.

"That sounds hot," I said. "I would have liked having a neighbor like her."

"Did you have a bad experience when you lost your virginity?" Sonya asked.

"No. Not at all. It was wonderful. My high school girlfriend and I had a terrific relationship. Our first time was perfect. But there was nothing remotely kinky about it. Being seduced by an older woman sounds like something I would have enjoyed."

"Yeah, too bad it didn't happen," Sonya said.

"It's not too late," I said. "We could do some roleplaying. You could pretend to be an older woman, and I could pretend to be an innocent virgin. That might be fun."

Sonya gave me a strange look. "I'm not sure I'm a good enough actress to pull that off."

"We're not trying to win an Oscar," I said. "We're trying to let you live out a fantasy. It arouses you. What do we have to lose?"

"Nothing, I guess. But we can't do it right now. We just had sex. Something like that would be a lot easier if we were both really horny."

"Maybe in a day or two," I said.

We cuddled for a while. At times like that I find it very easy to appreciate the differences between Sonya's body and Julie's. Sonya is smaller, leaner and more compact. She has very perky boobs, a cute face, and head-to-toe freckles. Julie is bigger, taller, and has wonderful large breasts that are a joy to play with. Her lovely legs are a work of art.

Some time went by, and I began feeling a stirring in my cock. I could tell we'd be able to have sex again soon. Sonya reached down and held my cock, feeling it get firm in her hand. Suddenly, she looked up at me and flashed a great big smile.

"I've got an idea!" she said. "I know how we can make that fantasy work!"

Sonya jumped out of bed and threw on a robe. "Wait here! I'll be right back!" After a few minutes she returned with a baggy that held what looked like two chocolate cookies.

"What's that?" I asked.

"These are edibles," Sonya said. She didn't need to explain that the cookies contained marijuana; I know they are popular with people who enjoy weed but don't enjoy the experience of inhaling harsh smoke. "One of my sorority sisters always has these on hand. She and her boyfriend like to have sex after they've had some edibles."

"I've never had sex like that," I said. "And I have very little experience with marijuana. None of my friends are into it."

"Have you ever used it?" Sonya asked.

"Sure. I liked it the few times I tried it. I particularly like listening to music after smoking a joint."

"Yeah. Music is my favorite," she said. "One time I smoked a joint and got really horny. It led to a very hot make-out session. That's what made me think it could help us find the inspiration to do that role playing game." Sonya handed me one of the cookies, then played some music through a nice pair of wireless speakers that filled her little room with sound.

We sat next to each other in the bed and waited for the edibles to take effect. It wasn't long at all before I noticed that the music sounded especially wonderful. Sonya looked even sexier than usual, and I loved the way it felt when I ran my hands over her hot body. My cock got so hard the head turned a pale shade of purple.

"I think you're ready," Sonya said, stroking my cock. "What do you think? Do you think you could pretend to be an innocent virgin with a predatory older woman?"

"That sounds very appealing . . . ma'am," I said.

Sonya laughed. "Ma'am. Nice detail," she said. "Alright, 'Benny.' I want to talk about something."

"What is it, ma'am?" I said.

"You've been hanging around my house a lot recently. I notice you always get a lump in your pants when you're here. Are you attracted to me, Benny? Are you getting boners because of me?"

"This is embarrassing. I am so sorry. I can't help it, ma'am. You're so pretty it just happens."

"Don't be embarrassed. It's perfectly natural for a healthy young man to be excited around women. I'm a little surprised, that's all. I'd expect you to feel that way about girls your age. I never expected you'd be attracted to me."

"You're the prettiest woman I've ever seen, ma'am," I said. "I think about you all the time."

"Is that right?" Sonya asked. "Benny, do you think about me at night when you masterbate? All boys your age masterbate. It's nothing to be ashamed of. When you masterbate, do you think of me?"

" . . . yes ma'am. Yes, I do. Every night," I said. "I'm sorry."

"Don't be sorry. I'm flattered. Do you have a girlfriend, Benny?"

"No ma'am. I've never had a girlfriend."

"Does that mean you've never been with a girl? You've never had sex?"

"I'm still a virgin, ma'am," I said. "I think about having sex. I think about it a lot. But it's scary. I'm not sure I could do it right."

"Nonsense. I'm sure you could, Benny. It's the most natural thing in the world. If you did it just once, you'd be fine," Sonya said.

"I don't know about that," I said.

"How about this, Benny? I've seen you staring at my breasts. Would you like to touch them? You'd like that, wouldn't you?" Sonya said.

" . . . yeah. Yeah, I'd like that," I said haltingly.

Sonya took my hand and pressed it against one of her boobs. "Doesn't that feel good, Benny?" She moved my hand to her other breast. "Don't you like squeezing my titties? I like the way it feels, Benny. Girls like it when you play with their boobs."

There was something almost unbearably pleasurable about what we were doing. Maybe it was the fantasy. Maybe it was the marijuana. Maybe it was both. For whatever reason, I couldn't believe how much I enjoyed pretending I was an innocent virgin in the presence of an older, experienced woman.

"Do you know what else girls like, Benny? Can you guess what else girls like for you to do to their breasts?"

"No ma'am," I said.

"Sure you do, Benny. I'm sure you know that girls like it when you kiss and suck their nipples. When you get a girlfriend, she's going to expect you to spend a lot of time playing with her boobs," Sonya said. "My nipples are very sensitive, Benny. Sucking on them makes me hot."

With that, Sonya leaned forward and put one of her nipples between my lips. "Suck me, Benny," she whispered. "I love having my titties sucked. Do that for me, Benny."

Like an obedient boy, I did exactly as Sonya asked. She eventually pulled away and put her other nipple in my mouth. I loved the way things were going, and I wasn't the only one. Sonya had a wild, excited look in her eyes. She was breathing so hard she was almost panting. She made sexy little sounds as I worked on her boobs.

"You're making me hot, Benny," Sonya said. "Do you know how you can tell if a girl is turned on?"

"No, ma'am. I don't," I said.

"It's easy," Sonya said. She took one of my hands and pressed it against her pussy.

"Feel how wet I am? You made me that way, Benny. You made me wet down there. When a girl gets wet, she wants you to play with her pussy." She spread her lips and moved my hand in a way that forced my fingers to slide up and down her hot, wet slit.

"That feels wild, Benny. So wild," Sonya said. "I love the way that feels."

I was so lost in sensations that I didn't even notice when Sonya climbed up and straddled my body. But I couldn't help but react when she began rubbing her wet pussy against my hard cock.

"Your dick feels wonderful like this, Benny," she said. "But I know something that will feel even better."

With that, Sonya raised up, took my cock in her hand, and lowered herself until I was all the way inside her. She moaned loudly, and I thought that we were finished talking.

I was wrong.

"This is what girls like most of all, Benny," Sonya said. Her voice was shaking and her eyes were closed, but nothing could stop her from continuing the little game where she pretended to be seducing me. We'd had a lot of fun in the past when Sonya rode me cowgirl-style, but this was different.

She was moving a lot faster than usual, and her movements felt a lot less controlled. I had a feeling it wouldn't be long before she climaxed. That was fine with me, because all this role playing made me so excited I knew my own orgasm would happen soon.

"Give me your hand, Benny," Sonya said. She put my hand against her clit and showed me how she wanted me to rub it.

"That's my clit, Benny. Girls need to be touched like this. Keep it up. I'm going to cum, Benny. Keep playing with my clit until I cum. Oh God, Benny, I'm going to cum. I want you to cum for me. Fill me up. I want to feel your cock filling my hot, wet pussy with your cum."

All that dirty talk pushed me right over the edge. I came, and came, and came some more. Sonya began to wail joyously. She looked so hot. So sexy. We'd had sex many times, and we'd had plenty of great orgasms, but we'd never gotten so lost in a fantasy. Her breasts started to shake, and I realized it was because she was having a particularly powerful climax. She shook from her head to her toes, and I felt her pussy throbbing around my cock.

"Oh . . . Benny . . . so good!!!!!" she said. Her voice was hoarse. I saw her squeeze her eyes shut. She gritted her teeth and shook her head back and forth. Sonya's climax went on and on until gradually she slowed down, stopped, and fell forward to lie on my chest.

When it was over, she let out a laugh. "God! That was exciting!" she said. "I can't believe how good that felt. Did you like it?"

"It was wonderful. Everything was perfect. You deserve an Academy Award," I said.

"What category?" she asked.

"Best actress in a leading role as a vixen," I said.

"You did pretty good yourself, 'Benny.' I predict I'll be taking your virginity more often from now on," Sonya said. "Did I do everything right?"

"It was great. But you need to know that the only person who calls me Benny is my Mom. You might want to call me something else next time. Thinking of my Mom is kind of a turn off."

"Message received, Benjamin. I'll call you something else, young man."

I wrapped my arms around Sonya and enjoyed the feeling of flesh against flesh. She'd selected some wonderful music, and it made our after-sex cuddling particularly pleasant. The edibles helped, too.

"Since that worked so well, I wonder what other sex fantasies you have," I said.

"Why are you so interested?"

"I want to please you. I want to be the best lover you've ever had."

Sonya smiled sweetly. "You already are, Ben. You earned that distinction a while ago."

"Back at you," I said. "I care about you, Sonya. A lot. So, are there any other stories you particularly enjoyed in the book of erotica?"

"I'm sure there are," she said. "I'll need to take a look at the table of contents to refresh my memory," Sonya said. "Off the top of my head, I can only think of one thing, and it's not exactly a fantasy."

"What is it?" I asked.

"It's a memory of something I actually did in real life. I'd like to do it again, but it isn't something you can help me do," she said.

Sonya explained that when she graduated from high school, she went to a party at a friend's house and hung out with a girl she knew. The two of them had a few drinks and were getting kind of giggly when the other girl started getting closer and closer. Pretty soon she gave Sonya a kiss, then another, and she finally persuaded her to go back to one of the empty bedrooms.

The two of them had a make-out session that was so hot it surprised Sonya.

"I've always felt that women's bodies are nice, but I'd never thought about actually having sex with a girl." Sonya touched the other girl everywhere, and the other girl did the same. "I think she had more experience with women," Sonya said, explaining that the girl put her hand inside Sonya's panties and massaged her pussy until she climaxed.

"I didn't have the guts to return the favor," Sonya said. "I was paranoid about getting caught. She was cool about it. We exchanged numbers and said we'd get together again when we could go somewhere more private. I lost my nerve and never called her, and I regret that now. I want to have sex with a woman someday. Or have a threesome. That would be delicious."

I couldn't help but think about Julie. By this time we'd done a lot of role-playing with me as a Dom and her as my Sub. She was getting good at following orders. I wondered what she'd think if I ordered her to have a threesome with me and Sonya. I had no idea if she was sexually attracted to women.

I'd ask her about it the next time I saw her.

And I'd find out what Grandpa Frank thought.

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Sonya has quite an imagination, doesn't she? Pretending to be an older woman seducing a virgin excited her. In Part 6, Ben makes progress on fulfilling Sonya's threesome fantasy.