Grandpa's Guide to Women - Pt. 01

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 for a label 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 1 follows Ben as he goes to college and makes new friends.

All characters are adults over 18.

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I was excited when I went off to college. I love my parents, but they are very conservative, so they imposed a lot of rules on me as I grew up. They didn't even let me date girls until I was 18. After so many years and so many restrictions, I felt anxious to live on my own. I wasn't planning to do anything stupid or crazy; I just wanted to hang out with friends and not worry about breaking some curfew or smelling like beer.

I'll miss my Grandpa Frank. We've always been very close, and he always gives me good advice. I hate it when adults treat me like a dumb kid because they think they have some duty to shield young people from the truth. As much as I love my parents, I don't pay much attention to their advice because I don't trust them to be honest. Grandpa Frank has told me the way things really are.

If you read my stories called Grandpa's Guide to Girls, you know that he gave me lots of help figuring out how to treat my first girlfriend, Beth. He even bought my first box of condoms. I felt more confident whenever I followed Grandpa's advice.

"I'm going to miss you, Grandpa," I said before I left. "You're the only adult in my life who treats me like I'm not a little kid."

"Go easy on your parents," Grandpa Frank said. "It's hard to know how to treat your children when they aren't children anymore. I hope you realize your Mom is going to call you Benny for the rest of your life. They've done a fine job raising you. Do your best to be grateful."

"I am grateful," I said. "I just wish they'd stop doing certain things. Do you know what Mom did this morning? She tried to give me a haircut! Every time she cuts my hair, she makes me look like an 8-year-old! I've told her a million times that I want to get my hair done by professionals from now on, and she just can't get the message!"

Grandpa Frank laughed. And laughed. "Your Mom never was any good as a barber. I used to feel sorry for you kids. She always made you look like little inmates."

That made me laugh, too. He was right. If you look at pictures of me after Mom gave me a haircut, I look like someone who just had a session with a prison barber. Ugh!

"I'm going to miss your advice," I told him. "I'll always be grateful for the way you helped me and Beth."

"Glad I could be of help," he said. "Anytime you want to talk, give me a call. How are you doing now that Beth is gone? You must miss her like crazy."

"Of course I do," I said. "She's going to college more than a thousand miles away. I won't see her again until Christmas break. I don't know how I'm going to do it."

"I know exactly how you'll do it, Ben," he said. "You'll pull yourself together and do your best to have a good experience in college. You'll work hard on your classes, you'll make new friends, you'll date new women, and you'll get used to being in charge of your own life.

"Beth is a wonderful girl, and I know you miss her, but the smartest thing you can do is try to meet other women. They'll be feeling lonely too. They've all said goodbye to their high school boyfriends, and they'll want to spend quality time with a nice young man who helps them get over their loneliness."

"I have no idea how I'm supposed to act around college girls," I said.

"Of course you do. You need to act exactly the way you acted with Beth," Grandpa said. "Be polite. Be interested in them as people. Listen to what they have to say. More than anything else, treat them like the most precious things on earth. That's exactly what they are, you know. When a woman agrees to spend time with you, it's the biggest compliment she can give. That goes double when she lets you remove her panties.

"Ben, there's something important that you need to understand. It's harder being a woman than being a man. A lot of guys don't realize this. They get hung up on the fact that if a girl wants attention from a man, it's easy for her to get it. A woman can walk into a bar and pick up a guy in five minutes. It's not like that for us men, and this makes some guys think women have some kind of advantage.

"That's a half-assed way to look at things, Ben. Here's the truth: The war of the sexes is over, and the women lost. Just because girls have an easier time acting like sluts doesn't mean a thing. After you get settled on campus, you're going to meet lots of nice girls, and you're going to get lots of nice intimacy from them. Don't get an attitude when one of them rejects your advances. That will happen. A lot.

"Part of the reason so many guys misunderstand all this is because they spend too much time chasing women who don't want to be caught. Some college girls are still pretty immature, and they come up with some very goofy reasons for deciding who they want to date. You might get shot down by some girl who only dates guys with tattoos, or who listens to headbanger music, or who rides motorcycles, or some other stupid crap. When that happens, move on. Don't waste your time on girls who don't recognize that you're worth dating. They'll learn the hard way that they were wrong."

"This sounds pretty complicated, Grandpa," I said.

"It's not complicated at all. Be friendly to everybody. Be kind, and generous, and let lots of girls know when you like them.

"There's something else you need to understand. Lots of the women you meet at college have had bad experiences with men, and now they feel hungry to meet a good guy. They may not act like it, but they are desperate for someone like you.

"I'm sure you've been told that young women mature faster than young men. That's the truth, Ben. Lots of college guys are so immature they drive women away. They spend all their time telling dirty jokes, or being rude, or having contests to see who can burp the loudest.

"That's not what sensible women want. They want a man who listens. Who knows how to kiss. They want a man who knows how to do all the intimate things you and Beth did together in the back of my van. They want someone who opens the door for them and pushes in their chairs. They want to be treated with respect. It won't be long before you have lots of girls chasing you."

"I'll be happy with one," I said.

"Well, it may seem like that now, but I suggest you keep your options open," Grandpa said. "You should date lots of girls. Don't look for an exclusive relationship. At this stage of life, you need to know what it's like to be with different women. And you need to protect yourself, because I can tell you exactly what will happen if you tell a girl you'll be faithful to her.

"She'll cheat on you. College is a time full of temptations. Some girl will say she wants to have an exclusive relationship, then she'll get drunk at some party, and before you know it she'll wind up in bed with a guy she just met. You'll find out about it, and it will hurt like nothing you've ever felt before.

"If everybody agrees in advance that you are both free to see other people, it's not possible to cheat. Chances are the first girl you date won't be the one you'll want the most."

I understood exactly what Grandpa Frank said, but I didn't think I could act that way. When I was with Beth, the idea of being with another girl didn't appeal to me, and I would have felt awful if she dated another guy. Besides, one thing I liked about my relationship with Beth was that we had sex all the time - and I mean ALL the time! The air mattress in the back of Grandpa's van became a very familiar place. I wanted that again, and I didn't believe I could get it unless I promised to be faithful to one girl.

It was a long drive to my college, but my parents loaded up the van and helped me move into my dorm, which was nicer than I expected. I shared a place with three other guys. There were four private rooms that opened to a common area with a TV, some chairs and a sofa, and some other furniture. The other guys talked about how glad they were that we could have female visitors. They acted like they were going to entertain an unending series of hot babes.

In high school, the guys who talked the most about sex were the guys who got it least, so I didn't pay much attention to all the macho posturing.

After my parents left I felt a little lonely, so I called Beth.

"I miss you," she said.

"Me too," I said. "I'm getting good vibes from everything so far, but I'd like it alot more if you were with me."

I noticed that there were voices in the background, and some of the voices were male. Grandpa told me to expect that Beth wouldn't waste a lot of time moping around and wishing we were still together. She was too sensible for that. Hearing that she was hanging out with a group that included guys helped me understand that my relationship with Beth was in the past. I needed to concentrate on my future.

I called Grandpa Frank the next day for more advice. "I'm surrounded by thousands of people, but I've never felt so alone in my life," I said.

"I was the same when I went to college," Grandpa said. "It will take some time for you to settle in. Nothing will change until you make friends."

"How am I supposed to do that?" I asked. "These kids seem pretty unapproachable."

"They seem unapproachable until you approach them," Grandpa said. "Just try to be friendly. Talk to people in class. I'm sure there are a ton of social events organized by the college. Go. Introduce yourself. Look, you have to study a lot, right? Study in the library instead of alone in your dorm room. They must have a student center with a coffee shop, right? Go study there.

"Tell me something - how is the female situation? Are there a lot of cute women?"

"Tons," I said. "Tons and tons and tons. There are so many hot girls here that it intimidates the crap out of me. I can't believe any of them will ever be interested in me."

"Yeah, it's going to feel that way right up until the moment one of them swoops down and snatches you up. By now I hope you understand that women will never ask you out on a date. What they'll do instead is let you know they'll say yes if you ask them.

"When a girl starts batting her eyes and giggling and tossing her hair back over one shoulder, be prepared. Always have some ideas of things you can ask her to do. Getting coffee. Going to see a movie. Colleges hire up-and-coming comedians to entertain students. That's a great first date. There's nothing nicer than having a conversation after you've spent an hour laughing your asses off."

"I'll figure something out," I said. "But I wish I could figure out a way I didn't have to just wait for a girl to express interest in me."

"Yeah, I understand, Ben," he said. "You can approach any girl who appeals to you and ask her out, but she'll probably say no. I read about some survey that said for every 8 times a woman is invited on a date, she declines 7 times. Those are pretty lousy odds, son.

"Here's an idea for you. Invite a group of girls to go out somewhere with a group of your guy friends. You could approach a group of girls who hang out together in one of your classes and say you and your roommates are going to a baseball game, and invite them to join you.

"That way, the pressure is off. It's not a real date. But it will give several ladies a chance to get to know you a little, and maybe one of them will decide she'd like to know you better.

"Keep in mind that when you are out in a group, it's like a competition with the other guys. If you can appear to be more mature, you'll be the one girls want to see again."

I didn't think that would work, but it was easy, and I had nothing to lose. I checked the calendar of campus events, and there was a free comedy show the next week. It featured four comedians I'd never heard of, but it seemed perfect. I asked my roommates about it, starting with a guy named Mike.

"Let me get this straight," Mike said. "You want to go up to random groups of girls and ask them out. You're going to say you've got three roommates, and you'd like the girls to join us at the show. Am I getting this right?"

"Yes. That's it exactly," I said.

"Ben, you are nuts if you think that will work," Mike said. "I can't get ONE girl to go on a date! If you think you can get a whole group to go out, you need to get your medications adjusted."

"My Grandpa Frank says it's easier to ask out a group of girls than a single girl," I said. "He's always right, Mike. Always. The only reason I managed to lose my virginity was that I followed his advice."

"Really? Wow. OK, fine. Count me in. I can't believe you think you're going to convince a random group of girls to go out with four guys they've never met. But give it a try. I'm willing to do anything that might help me get laid before I graduate."

I gave it a try, and it worked just like Grandpa Frank said it would. There's a group of five girls who sit together in my American history class, so I went up to them before class, sat down, and introduced myself.

"I can tell that you ladies are friends," I said. "I hope this doesn't sound too weird coming from a guy you don't know, but my roommates and I want to go to the comedy show Friday. I love comedians, but they are a lot more fun if you go with a group of people, especially if some of those people are of the female persuasion. It would be OK if my roommates and I went by ourselves, but if that happens it will be a sausage fest, which gets old fast. I'm sure they'd behave much better if there are ladies present."

The girls looked at me like I had three eyes and antennas coming out of my head. "Like... how will they behave better?" one girl asked. "I don't get it."

"Well, for example, I'd really like it if all of the guys take showers before the performance," I said. "If you show up, I can guarantee everyone will take a shower AND put on clean clothes! They might even use mouthwash."

I guess I must have delivered that last line properly, because the girls started to laugh. "They sound charming," one girl said.

"Oh, you have no idea," I said. "They are all house broken. I promise I will kick their asses if they don't behave like civilized people in front of you. No belching. No farting. Minimal usage of the F-word."

That triggered another round of laughter. Things were going well. Thanks, Grandpa Frank. I figured I needed to let the ladies think about the idea, so I shifted gears.

"Give it some thought and you can let me know later," I said. "If you want to go, I will pick up the tickets. The event is free, but you have to get tickets in advance. I guess they don't want 2,000 students to show up at a venue that seats 800 people."

With that, I changed the subject, asking how the girls know each other. It turned out that they are all members of the same sorority. They'd managed to change their schedules around so they went to a lot of the same classes together. That explained why I also saw the same group sitting together in my Freshman Composition class.

I thought it was unlikely that all five of the girls would want to go, so I hedged my bets by inviting two girls who always sat together in my software coding class. They both want degrees in video game design.

It worked out pretty well. Three of the sorority girls decided to go, and both of the gamer girls. My roommates were very impressed that I'd convinced five girls to go out with the four of us.

"Damn, Ben! How'd you manage that?" Mike asked.

"Hypnosis," I said. "I put them all in a trance and convinced them that there's nothing they'd rather do than go out with four sweaty freshmen boys. Listen, I promised these ladies that we'd all take showers and put on clean clothes before the show. If we want to see any of these girls again, we need to act civilized for a couple of hours. Can you guys impersonate adults for that long?"

"If we must," Mike said.

I picked up the tickets, and it gave me an idea. The seats were numbered, so I gave the odd numbered tickets to my roommates, then handed the even numbered tickets to the girls. This meant the seating arrangement was boy-girl-boy-girl, which everybody recognized was my way of encouraging mixed conversations.

"Fiendishly clever," said the girl next to me. Her name was Julie. "Do you think making us sit like this will get you and your roommates laid?" She smiled as she said it, so I knew she was joking.

"I get no credit for the seating arrangement," I said. "This is the way my Mom organizes dinner parties. I'm pretty sure she isn't trying to encourage people to hook up. Considering the type of folks she invites to dinner, it would be pretty twisted if that's what she has in mind. I sat next to my Aunt Velma last time.

"The idea of hooking up with Aunt Velma conjures up images I don't want to think about too much."

The show was great. Grandpa Frank was right. We laughed so hard our bellies ached. When it was over I made an attempt to keep the group together for some actual conversation.

"Is anybody else interested in going to the coffee shop?" I asked. "It's too early to go to bed. I'm in the mood for cappuccino. Would anyone like to join me?"

The two gamer girls went back to their dorm, but the three sorority girls and my roommates all walked the short distance to the cafe in the student center. We got our drinks, sat at a big round table, and started to talk.

"How'd you guys like that joke about the dude with the hangover?" I asked. Grandpa Frank said that a good way to keep the conversation going was to talk about individual jokes. He was right! Everybody laughed, and we talked about one joke after another. I put myself in charge of making sure there were no long awkward silences. The evening was shaping up nicely.

My roommates didn't realize that we were participating in a kind of competition for the attention of the girls. As I expected, they were on their best behavior, but every so often they did something that made it clear they were goofy adolescents. Sometimes they laughed like hyenas. Sometimes they had bad posture. Every so often somebody said something a little bit crude. I felt grateful that nobody picked their nose.

Since I was the person who organized the evening, I felt I had a special responsibility to act like an adult. I sat up straight, used good diction, avoided profanity, and tried to steer the conversation in ways that made sure all the girls could participate. I realized that the girls were deciding what they thought of all of us, and that I had a perfect opportunity to make myself look good in comparison with my roommates.

"Folks, it's getting late, and I get the feeling that you ladies have had just about enough of our company for one evening. Guys, I think it's time for us to walk them to their sorority."