Grandpa's Guide to Women Pt. 04

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 4 describes Ben catching feelings for a new girlfriend while an old one tries to win him back.

All characters are adults over 18.

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Sonya invited me to spend the night. It was a bit uncomfortable trying to sleep in her tiny little bed, but we managed. I couldn't take her out for breakfast because we both had early classes.

In the morning she walked me to the door, and we went past two of her sorority sisters. They looked up at us, grinned, and one of them said "Good morning, Ben. Did you sleep well?"

Sonya replied for both of us. "This poor guy didn't sleep a bit. Somebody kept waking him up. He was up and down, all night long." I believe I already mentioned that Sonya is a very smart girl. It was the perfect response. I'd like to be that clever.

I was going to be late if I didn't hurry, so I was jogging when I went past Julie's sorority. Once again, I saw some girls in the window, and I'm sure they saw me. Damn it, this is getting annoying! I thought to myself. Those girls are going to tell everybody where I spent the night! I'm getting tired of my personal life being the subject of gossip every damn day! @#$!

My roommates were just getting up when I got back to my dorm. "Ben! Where were you last night?" Mike asked.

"I was visiting a friend," I said.

"Was your friend of the female persuasion?"

"Maybe."

"Was her name Julie? Or Sonya?"

"Listen guys, I've got to get ready for class, and I don't have much time. I need to get in the shower. I can't talk right now."

"Yeah. You do need a shower, Ben. You smell like a French whorehouse." That got them laughing like hyenas.

I put my flask back in its hiding place, then grabbed a towel and some fresh clothes. I got to class in plenty of time. As soon as I sat down Julie walked over.

"Can I talk to you?" she said.

The expression of her face was one of pure misery. I couldn't tell if she was upset because someone told her I'd spent the night with Sonya, or if experiencing non-stop slut shaming was wearing her down. It was probably a bit of both.

"Of course, Julie," I said. "We can talk anytime you want."

"How are you doing?" she asked.

"I'm OK. Putting one foot in front of the other," I said. "How about you?"

"I'm doing awful," she said.

"I'm sorry to hear that," I said.

"No you aren't. You're glad I'm suffering for my mistake."

"Julie, that is not true, and I'm sorry you think it is. I am not mad at you. I am over it. I realize that things must be pretty hard for you. I'll do whatever I can to make things better."

"Really?"

"Of course. I care about you, Julie. That hasn't changed."

We talked a little more, and it turned out that what she wanted to discuss were her STD tests, which proved she hadn't picked up any infections from that frat boy.

"That's great news," I said. "It would have been very sad if the tests came back positive."

"I was hoping I could see you," she said. "Now that you know I can't give you a disease, I'd really like it if you'd let me spend the night again. I miss you so much I'm going a little crazy.

"I know you don't want to be seen in public with me, but if you don't mind I'd be happy to just see you in your dorm room. I need you to hold me again. Please say yes."

"Julie, I was upset when I said I didn't want to be seen with you. I don't feel that way anymore. I'm proud to take you out. I miss you too. If you'd like to be with me in my room tonight, that would be wonderful."

Julie was smiling as we arranged for her to visit. I realized something odd. I'd had sex with Sonya that morning, and it seemed I would have sex with Julie that night. It meant I'd have sex with two women in one day. Another first!

Something about that felt good. Very good. Extra special double good. Maybe I was being juvenile thinking that way, but I couldn't help feeling it was great that two very desirable women wanted me on the same day. Grandpa Frank said that college would give me the opportunity to have first-time "romantic adventures" with different women.

Those were the words he'd used. "Romantic adventures." I'd believed him, but I hadn't imagined that so much would happen during my very first semester.

That evening Julie showed up at my dorm. She was wearing a very pretty dress, and her hair and make-up looked especially nice. She has a very curvy body, and the dress she wore displayed it nicely. I have no way of knowing if she made a special effort to look good for me, but I liked to imagine it was her way of trying to repair our relationship.

She looked . . . unusual. It took me a few minutes to figure it out, but eventually I realized that Julie wasn't wearing a bra. She has very large breasts, and I'd never seen her go braless before. When I gave her a hug I ran my hand down over her bottom, and I could tell she wasn't wearing panties, either. I felt certain that coming to my room without underwear was a sexy gesture meant for me.

Still, she looked very nervous. I thought it would be nice to offer her a cocktail, so I pulled a soda out of my mini-fridge and mixed in an ounce of vodka. I got a soda for myself, but skipped the alcohol. Grandpa Frank said it's a bad idea to drink two days in a row, and his advice has been so good I've decided to follow it as well as I can.

"How is your drink?" I asked.

"Very nice, thank you," Julie said. She had a strange expression on her face.

"What's wrong?" I asked.

There was a long pause. "This is the first alcohol I've had since . . . the night I got so drunk."

"I hope that doesn't make it hard for you to enjoy it," I said. "Julie, I meant it when I said I forgive you. I hope you've forgiven yourself. I hope you've stopped beating yourself up."

She looked sad. "There are plenty of other people beating me up these days," she said. "People are saying crude things about me. Since that night, a lot of sleazy guys have asked me out. I know it's because they think it will be easy to get me drunk and have sex. Ben, this is just horrible."

Things were happening exactly the way Grandpa Frank predicted. "That's a lot of sexist bullshit, Julie. Nobody is doing any of that to the guy who got you drunk. If you were a man, people would be congratulating you. This is very unfair."

"Those are the first kind words I've heard since this whole mess happened. I swear Ben, I'll never get that drunk again."

"Good plan," I said. "But there's no reason I can't make you a second cocktail. Would you like another one?"

"Yes please," Julie said, smiling.

"This is the first time I've seen you smile for a while," I said.

"It's because I'm here with you," she said.

"Maybe your cocktail gets some of the credit."

"That too," she said.

By the time Julie finished her second drink, she seemed much more relaxed. I couldn't help but remember that she'd gotten alarmingly drunk a while ago, and I wondered if she'd ask for a third drink. I decided right then that I'd enforce Grandpa Frank's two-drink limit, but Julie seemed satisfied after she finished her second cocktail.

"I've been thinking I should transfer to a different school next semester," Julie said. "It might be best if I went somewhere no one knows me."

"Julie! Don't talk that way! Don't let one little mistake force you to turn your whole life upside down! I would miss you."

"My life feels pretty upside down right now," she said. "I wish there was something I could do to fix things."

"Maybe there is," I said. "Maybe we can think of something."

Julie gave me another sad little smile, then leaned in to kiss me. I could tell that she'd had enough talking, and she wanted to do what she'd come to my room to do. I usually give Julie sweet, tender kisses for a while before getting more passionate, but for some reason I felt like going for deep, soulful kisses immediately. I took her head in my hands and pressed our lips together forcefully. I was being pretty rough, but that seemed to be fine with Julie.

I caressed her braless breasts through the thin material of her dress. It seemed to arouse her more than usual. It certainly had that effect on me. Immediately, my cock was hard as oak.

I shoved Julie down on the bed and reached up her skirt. I knew she wasn't wearing panties, and I wanted to touch her pussy. I roughly pulled her legs apart and began running one finger up and down her slit. We'd only been at it for a few minutes, and already Julie was hot and wet down there. Maybe it was the alcohol. Maybe it was because we hadn't had sex for a while. Or maybe it was because I was being more demanding than usual. More insistent. Aggressive. For whatever reason, Julie was moaning and writhing around on the bed much more passionately than ever before.

"Get out of that dress," I said. It wasn't a request. I grabbed it by the hem and whipped it off her body as fast as I could, then threw it across the room. Julie had a wide-eyed expression on her face. Things were not going the way they usually went between us. We could both tell something was different.

I began kissing, licking and nibbling Julie's breasts as I continued playing with her pussy. She pulled me closer, and I began biting her nipples. I didn't do it hard enough to leave a bruise or anything like that, but I was using my teeth in a way that had to cause a little pain every time I bit down. I began stroking her clit with my thumb as I slid one finger into her pussy.

Julie must have liked that, because she had a very strong orgasm. "Ben! Ben! Ohhhh!!!!" she cried. My dorm has thin walls and cheap doors, so I was sure my roommates must have heard Julie, but at that moment I didn't care. All I cared about was the fact that Julie's whole body was shaking from her head to her toes. It was exciting in a brand new way. I'd never had this kind of sex before. I was acting like a brute, and we both enjoyed it.

What is going on? I asked myself. Why am I being like this? Until that moment, I'd always treated women like precious creatures who needed to be treated delicately. This was the first time I'd been so rough. Why was I throwing Julie around on the bed? Why was I acting this way?

I eventually realized that my feelings for Julie had changed. I used to think of her as a sweet, innocent girl who needed to be treated with gentle, tender respect. I no longer thought of her as even slightly sweet and innocent. Have you ever heard a person described as "down to fuck"? I'd come to think of Julie as being that way.

I would never be able to forget that Julie was a girl who had gotten drunk, flashed her tits in a room full of people, then fucked a guy she just met. It seemed to me I needed to treat Julie differently than I'd treated her before. I wasn't trying to be mean or anything. I just wanted to recognize reality and give her the kind of sex she wanted. It felt as though she needed me to be a little rougher and more forceful than I'd realized before.

She certainly seemed to enjoy this new way of having sex. Grandpa told me that some girls like to pretend they are fucktoys for their boyfriends. They enjoy imagining they are being used as sex objects. I felt like doing whatever made me feel good, and hoped she liked it.

I decided I wanted a blowjob. I'd only had a few real blowjobs. Julie had sucked my cock briefly a few times. My high school girlfriend Beth was the only woman who'd ever sucked me off, and she'd only done that a couple of times. I'd never asked a girl to blow me, figuring it was something I should let them do on their own.

At that moment, I didn't want to wait for the day Julie decided to suck my cock. I'd just given her a first-class orgasm. Now it was Julie's turn.

"Suck my cock," I told her. It was an order. It was the first time I did anything like that.

I put one hand on the back of her head and shoved her down toward my lap. She didn't resist at all, acting as though there was nothing she'd rather do at that moment than suck my dick. She began licking the head and shaft, then sucked me as deep into her mouth as she could. She bobbed her head up and down, using her hand to squeeze and stroke the part of the shaft that didn't fit in her mouth. Julie was putting a lot of effort into sucking me, and I appreciated it.

"That feels good, Julie," I said, caressing the back of her head. "You're a great little cocksucker."

Cocksucker? Why did I use that word!? I had no reason to believe Julie would appreciate me using such a dirty word to describe her. I've heard that some women like it when men talk dirty, but I didn't know what Julie thought. At that moment I didn't particularly care how she felt about being called a cocksucker. I just wanted her to keep sucking.

I'd been pretty excited before Julie began, and it didn't take long at all before I felt an orgasm building inside me. When Beth sucked me, I always warned her before I came in her mouth. I didn't warn Julie. Instead, I cradled her head in my hands and held her down so she couldn't pull away when I came. I wanted Julie to get the message that I expected her to swallow my cum.

It felt fabulous when I finally climaxed. I'm sure I was especially aroused because I was "forcing" Julie to do things we'd never done. She did a great job sucking my cum right out of my balls and swallowing every drop. She kept at it until my cock was completely soft.

We weren't finished. The room smelled like sex by then, and I felt an overpowering desire to taste Julie's pussy. It would give me something fun to do while I waited for my cock to get hard again. I grabbed her shoulders, threw her down on her back, spread her legs forcefully, and began to eat her pussy like a starving man.

"Oh . . . my God . . . Ben!!!" she said. I reached up and squeezed her breasts - hard. Hard enough to hurt. I kept it up for long moments, enjoying how she thrashed around on the bed as I sucked, licked and nibbled all over her pussy. I sucked her clit into my mouth and ran my tongue over it forcefully, and that made her climax again. Because my face was so close to her pussy, I was able to watch Julie's vaginal muscles contract as she came over and over. It was indescribably exciting.

It was exciting enough to restore my erection. She was sprawled on her back recovering from her second orgasm as I crawled up the length of her body until we were face to face. I reached down, took my cock in hand, and ran it up and down the length of her slit.

"I can't believe you have any energy left," she said.

"I'm not finished with you yet," I said.

She felt me put the head of my cock at the entrance to her passage and press forward. She was very wet by then, so I slipped inside with little resistance. I wasn't being rough, but I wasn't being gentle, either. I went in and out at a steady pace, working my cock deeper and deeper. Julie was shaking her head from side to side, gritting her teeth, and pounding on the mattress with little fists.

We did this for a while, then I got the urge to try a different position. I stopped without warning, rose up on my knees, then twisted Julie around until she was in the doggy position. Since I'd already had one orgasm, I didn't feel a compelling need to come again immediately. But as the minutes passed and I saw that Julie was becoming more excited, I began to feel another climax growing inside me.

I wanted to make her cum again, but I thought I should be more concerned about my own needs. Julie had already climaxed twice. I'd love to make her have a third orgasm, but it no longer felt essential.

That's when I looked down at the back of Julie's lovely body. She was so curvy, with a narrow little waist, generous hips, and nice broad shoulders. She is a big, strong girl. Her breasts were so large I could see them swaying as I pounded into her pussy.

This angle gave me a particularly nice view of her pretty little brown butthole. Something about it looked especially alluring right then. I didn't have a lot of experience with anal sex, but I felt a sudden urge to fuck Julie's ass. She seemed to be very aroused right then; I felt no need to ask for consent.

I reached for my lube and applied a generous amount to her anus. Julie froze. I knew the lube must have felt cold enough that it probably startled her when she felt me rub it on her tiny little pucker. Maybe she didn't want me to fuck her up the ass, but she must have known it was going to happen either way. I worked my pinky finger into her hole and spread the lube inside. I applied another glob of lube to my finger, then stuck it in again.

There was no way for me to tell if Julie liked what I was doing. We'd never had anal sex, and I know that a lot of girls don't want to do it. I'd had anal sex a few times with my high school girlfriend Beth, but only after we'd been together a long time, and only after a lot of foreplay with lots of lube. With Julie I just pulled my cock out of her pussy, placed the lubricated head on top of her anus, and pushed. It took a lot of pushing because she was so tight back there, but it wasn't long before my cock slid inside.

"Oooohhhhhhh!" she said. Julie closed her eyes and laid her head down on the bed. She made little whimpering noises as I worked my cock deeper. I pulled back a little, then pushed forward farther than before. My cock went in deeper and deeper, and it felt amazing. I especially enjoyed doing something so wild without asking permission. It felt great treating Julie this way. I was making her do what I wanted instead of worrying too much about what she thought.

My girlfriend Beth once told me that anal sex always hurt when we did it, but that she liked the pain. A little bit of pain seemed to make her pleasure more intense. Maybe that's how Julie felt right then. She told me later that my cock was the first one to fuck her up the ass. It occurred to me that I might be taking a kind of virginity from Julie. The thought was overpoweringly exciting.

That's what I was thinking when my climax began. I'd already shot a load of my cum down Julie's throat, and I wondered how much I had left to shoot up her ass. It was hard for me to tell, but from the way my cock throbbed over and over, I knew I was giving Julie more than enough for her to feel. It seemed that she liked the sensation of her ass being flooded with warm wetness, because she began having another climax.

This third climax was more powerful than the first two combined. She began wailing like a car alarm. "Ah!! Ah!! Ah!! Ah!!!" she screamed. Earlier, I'd been concerned that my roommates might hear the sound of us having sex. Now I imagined that everyone in the dorm must be able to hear Julie's loud cries.

The strong muscles of her rectum squeezed my cock again and again. It was like when her pussy throbbed around my cock, but much more powerful. It seemed that her ass muscles were trying to push me out. I had to shove forward forcefully just to stay inside.