Pathways Ch 03 04 1

Chapter 3 Deb's Plan

Debbie:

I had my arm wrapped through Ian's, and I made sure he couldn't help feeling the side of my breast as I leaned into him. I told him how much I enjoyed the play and I saw the smile that produced. He suggested we have a snack, and after a brief debate we agreed it would be my treat. I told him he'd treated me to a lovely evening and I'd like to contribute to it as well. He said something nice to me about just being happy to be with me.

I reached up and pulled his head down and kissed him. I mean, I gave him my best, right on the lips. And I kept on kissing him for a while too. When we broke, I looked at him and smiled. I was trying to convey a different impression. The evening was going just the way I expected, now that I thought about it. Ian was very inexperienced and unsure of himself around me. I had that effect on a lot of guys. I was happy that I hadn't done anything to startle him. After all, he was a rookie at dating.

We hadn't moved since I kissed him. We were standing on the sidewalk, not far from the theatre and I was staring at him intently. That's when I decided that we really didn't need to have several dates to decide. I was happy that we could become boyfriend and girlfriend. It was a bit of a risk to cut the dancing around each other and get to the meat of the issue. And I do mean meat. I had no trouble detecting that Ian was well equipped in the manhood department. He'd had a hell of a time trying to hide his erection and not be embarrassed. All the while, I'd been torturing him mercilessly at every opportunity.

I almost laughed at his uncertainty when he asked me if I was sure, but hid it with another long kiss. We were making quite a spectacle of ourselves out on the sidewalk. People were walking around us as we stood there holding each other.

We talked a bit more about how I was impressed with his being a gentleman, trying to convince him that I was sincere. Yes, I was laying it on a little thick, but I continued to hold onto his arm as we resumed our walk back to the car. I made sure it was in full contact with my breast. It was cool and damp that evening and I was anxious to get to the car and get warmed up. I didn't want to catch a chill. As soon as I slid into the front seat I folded up the center armrest and slid over next to him. I cuddled up to him as soon as he was seated. I put my arm around him and the next thing he knew we were kissing again. This time there was tongue involved and more.

It was time to speed up the process. I took his hand and placed it inside my coat and right on my breast. He didn't expect that at all, but now that it was there, the question in my mind was what should I do next? My first instinct was to go for the prize, but I resisted the urge. He ran his hand over the tip of my brassiere, feeling for the nipple beneath the fabric I guessed. Thank God he was being gentle and not mauling me. It didn't take long for my nipples to react. All the while, we were kissing, tongues included. When I stopped to look up, I saw the windshield and side windows were completely fogged. I suggested we find somewhere a little more private. We didn't need someone coming along and spying on us.

Ian was totally inexperienced. I wouldn't have been surprised if he were still a virgin. After we'd parked in the deserted lot, he didn't know what to do next. I took that decision out of his hands, so to speak. I pulled my sweater out from my skirt's waistband, reached behind my back, unhooked my bra, did my usual trick and voila! My brassiere was in my hand. I set it aside and pulled my sweater down, but didn't tuck it in. It was still pretty cool in the car.

It was obvious I was going to have to take charge. He wasn't sure what to do next, so I reached for his hand and guided it up underneath my sweater to where I was sure he would be happy. Luckily, it wasn't cold. I could tell by his reaction that this was all new to him. God, how could a twenty-year-old guy in this day and age be so inexperienced? It wasn't like he was ugly or stupid. Hell, he was cute and smart and polite. So, I had an opportunity to bring a nice, young guy along and teach him the ways of being with a woman ... and teach him properly.

We continued our kissing and his fondling until I put my hand on his fly and then grasped his erection. I felt him react to my move. I think he was wondering what I might do next, so as he leaned back to see what would happen, I undid his belt, then his top button, and pushed his zipper down. I reached in and now had a light grip on his cock, with only his briefs in the way. My suspicions were confirmed. He was a big boy. It only took a moment to slip my hand inside the waistband and now it was flesh on flesh. He had one hand on my breast and I had one hand on his raging hard-on.

This was all new to him and I doubted he would last very long before he shot off. Oh I'm sure he'd felt some girls up before and maybe had done some heavy petting, but I was pretty sure I was leading him into uncharted waters. He had no idea what I was going to do next and so he just sat there, waiting for my next move. I could tell he was getting close to ejaculating with my hand working slowly on his erection. There was only one way to deal with this. I lowered my head and covered his erection with my mouth.

He was completely dumbfounded by this and stopped whatever he was doing with his hand. He was helpless and I felt him explode a moment after I took him in my mouth. He was so surprised that he was apologizing in embarrassment almost immediately.

I rose up, wiping my mouth with the back of my hand. Despite the dim light in the car, I could see the look of astonishment slowly dissolve. He didn't understand at all what had just happened to him. Oh, he knew what had taken place, but it wasn't something he had expected or probably even hoped for. I just took the matter into my own hands ... and mouth ... and did it! No hesitation and no discussion.

I told him I thought he was a virgin and I asked if I had upset him. He said he wasn't, but admitted that he felt I wouldn't think he was very mature or cool, as he put it. I tried to assure him that he was cool and that he was a nice guy that made me feel safe and secure when I was with him. I admitted I wasn't a virgin and hadn't been since I was sixteen. I asked him if it bothered him and he said it didn't. I also admitted that I had a lot of pressure on me when I was young to put out, but after some experience, I realized I was looking for more than just a sex partner. I knew what most guys were interested in: my tits and my ass. I told him that I knew he was different and not like a lot of the other guys. He was still uncertain about what had just happened, but I think I was getting through to him.

I chose that moment to lower my head again and take his limp cock into my mouth once more. It wasn't very long before he was hard once more. When I asked him to slide over to my side of the big front seat, he did so. I think he had an idea what I might have been planning and he was right. I lifted my leg over his and straddled him, once again gripping his erection. I pulled the crotch of my panties off to one side and then aimed the tip of his cock at my pussy. A couple of swipes along my slit made him jump before I began to sit down on his cock. He was really tense and I wondered if this might cause him to go off quickly once more. Luckily, that didn't happen. I lowered myself just a bit at a time. Ian sat still, allowing me to decide what to do. I stopped moving.

I told him he wasn't a virgin any more, he'd officially been baptised. I got a very positive response. Then I said something I hadn't planned to say. I told him I'd had the "hots" for him since the first day of class. I told him I thought at first he was cute, but when I got a quick look at the bulge his package made when I worked my usual tricks, well ... I knew I had to find out more about him.

He might have been a bit pissed that I had set out to seduce him, but if he was, it wasn't showing. The idea that he was having sex with me didn't escape his notice, I assumed.

I told him we were only just getting started, so hang on. I was going to give him his first lesson in having sex. I could teach him what girls ... women ... enjoyed. What turns them on. He was completely in favour of that. But then ... to my surprise ... he told me he was only thinking of making me happy. That both pleased and startled me. I didn't expect that at all.

Without thinking about it, I told him I'm not his forever girlfriend. Next year we probably wouldn't have any classes together, so he'd move on and find someone else. I would too. He wasn't thrilled about that, but I told him we still had months to go yet and we could wait and see what happened in the next semester. I don't think that quite satisfied him.

I watched him absorb what was happening as I rode slowly on his erection. I could almost read his mind by the expression on his face. This was all new ... never-never land new. Me? I was getting everything I expected. Ian was blessed with a very nice, thick cock. Not any longer than most I'd seen, but thick and that was the key to the feelings he was creating in me.

I had to assure him that I was protected when he worried about not using a condom. I think the fact that it was far too late for that probably didn't register on him. I was a very single-minded young woman at that moment. I was getting close to a very nice moment and I didn't want any more interruptions.

Over the next weeks I taught Ian the fifty ways to please your lover. Well, maybe that's an exaggeration. Most of the time, we used my bed at my brother's house. They bowled on Tuesdays and went out with friends on Saturdays. I'm sure we didn't fool either of them what we were doing in their absence. I got some knowing looks from my sister-in-law, Gail, and a couple of comments on the sly from brother, Rick. Ian might have been embarrassed if it wasn't for the fact that they were friendly to him and didn't mind his dating me.

I wanted to be more than just a hot body. I knew I was smart, dedicated to getting good grades and, more surprising to me than anything, something of a leader. I tried not to just order people around, but convince them that they would want to do the right thing. And not just guys, either. Some of my girlfriends and acquaintances were equally eager to follow my lead. What I was trying to do now was to find a guy I could hook up with who made me feel good. Not just the sex, but who could keep up with me in class, whom I would be happy to be seen with. I wanted to try and change my image from the little sexpot to something a lot nicer. Ian was a good first step.

Chapter 4 Holly and Robin

Ian:

My sophomore year was coming to an end. I would be working at Maxwell Marine again, while Deb went home to Sechelt and spent the summer at her dad's hardware store. I was going to sorely miss her over the next three months, and I told her so.

"Don't get hung up on me, Ian. We've had a great time together and maybe that's all there will be. Whatever you do, don't fall in love with me. You don't have enough experience with women to know what you want yet. You need to find another partner for the next year or so. Maybe another after that, too. We're a miss-match, you know. Not just physically, but emotionally too. You're a really nice guy and you need a girl who will fit with a guy like you."

"I don't understand," I said, frustrated with this conversation.

"I mean, you need a girl who will rely on you, not the other way around like it is with us. That comes with experience. You won't have any trouble being a good lover, that's for sure. You've come a long way since that first night in the car. And God knows, you have the equipment to satisfy any female," she grinned.

She had told me that I was bigger than most men ... or boys ... and that had surprised me. Not that I had compared myself to other guys, of course. But she said that in her experience, I was thicker than most and that was something I'd have to be careful with. I wouldn't want to hurt a girl by being too aggressive. She was always good at boosting my ego, and I accepted what she said as gospel. During my time with her she introduced me to oral sex, and I found that I got my reward from giving her pleasure as well as from receiving it. It was probably the most valuable lesson I learned from her. Not only the oral sex, but the practice of pleasing my partner.

Deb was a walking wet dream for a kid like me. She was right out of a fantasy sex novel and it took me forever to come to grips with the fact that she was mine for a few months. If I tried to tell my friends about her, they wouldn't believe me. I never did take her to meet Mom and Dad. I didn't have the nerve. And Kenny? No way. Who knows what he might have been telling his buddies.

I had no hope of finding another girl like Deb. She was one of a kind and I could look for the rest of my life and not come across anyone like her. It wasn't just her amazing body. She was my teacher, too. She was incredibly patient with a virgin greenhorn and taught me so much about how to treat a woman. I tried to follow everything she said. As far as I was concerned, she was the last word in how to behave with a female.

I wasn't in a position to find a new girlfriend over the summer. I was working five and a half days each week, with Saturday mornings pretty much dedicated to getting the stock room back in good order and putting away incoming parts shipments that we didn't have time for during the week. But I was paid well and over the past two years I had gotten to know the guys and gals at the business and we all got along pretty well. Unfortunately, there weren't any single young women for me to get acquainted with.

Summer came to an end and it was back to school for my third year. I was finished with psychology, but continued with history and political science. I picked computer science in place of physics and took an English composition course to improve my writing skills. I had a home computer now and I wanted to take advantage of it.

I joined a writing club with the idea of having someone critique my work. I had the basics, but I needed better organization of my thoughts and I needed to learn to compress my work. "Less is more," Holly Everall would preach.

Holly was a fourth-year student taking English composition. She was the complete opposite of Deb in many ways. First of all, she was tall, nearly as tall as I was. She was slim, but not skinny. She had breasts, they just weren't huge. And she had a very nice, pert ass that she enjoyed swinging as she walked.

Also, unlike Debbie, she had dark hair, almost black, dark brown eyes, a narrow face, but attractive with a long straight nose that seemed to suit her perfectly. I thought she had a suntan, but later I realized it was her natural skin colour. She left me with the impression of being somewhat mysterious. Part of it was her look and part was her attitude. She wasn't outgoing like Deb. She was kind of slinky-sexy. And she often liked to shock people with her language or comments.

Our group met twice a week, and by October, I had decided I was going to see if I could get a date with Holly. I wanted to know more about her, but in truth, she was a fine looking female and that was my main interest.

"Holly, I was wondering if you'd be interested in going out on a date with me?" I asked when I was able to get her alone for a minute or two.

She looked at me questioningly. "What kind of date?"

"I can make a couple of suggestions and you can choose what you would prefer," I said.

"I don't know. I don't know you very well, Ian."

"I could give you references," I said, hoping she didn't call me on that.

"What kind of references?" she asked. At least she hadn't shut me down yet.

"I had a steady girl last year. Her name is Debbie Cummings."

"How come you're not with her now?" she asked again. It was getting to be a third degree interrogation.

"Her choice, not mine. I'm sure if you ask her, she'll tell you," I said, hoping I wasn't taking too big a risk.

"Where would I find her?" she asked.

"I can give you her phone number. She lives with her brother and sister-in-law in Richmond."

"Okay. Give me the number and I'll check you out," she said.

I wondered just how smart this strategy was, but Deb never gave me a hint she wasn't happy with my behaviour, so maybe she'd put in a good word for me. I had to hope so, anyway.

The next day, Holly was back waiting for me at the chemistry building.

"Debbie said you were a good guy. I could trust you. She also said you had an awesome cock." She delivered the line without a moment's hesitation or a smirk. Deadpan.

I scrambled to think of something to say, but Holly cut me off.

"I usually only go on first dates with my roommate, Robin, as a double. Can you find a date for her?"

"I don't know," I said, dealing with another surprise. "I don't know Robin, so it's hard to know who might be compatible."

"I can solve that. She's meeting us in the Student Union cafeteria at three-thirty. Can you be there?"

I nodded. "Sure. I'll see you there."

That was the strangest conversation I'd had in a long time. Holly didn't waste words or time. She got to the point and said what she wanted to say. Okay, I could probably deal with that. She was different, for sure. This might be interesting.

I pushed my way into the Student Union cafeteria just after three-thirty and saw Holly sitting at a table with another girl. I didn't recognize her, but assumed it was Robin. She was quite nice looking as well, but not quite as interesting as Holly.

"Hi, Holly. This must be Robin. I'm Ian Kiernan," I smiled, holding out my hand.

Robin took it and held it softly for a brief moment before withdrawing it. "Hi, Ian. Nice to meet you."

"I guess you know what this is about, since Holly arranged this meeting," I stated.

She nodded. "Holly said you might be able to find me a date."

"So ... what kind of guy would interest you, Robin? I know a few guys who are unattached and I'm sure they'd be interested in dating a nice looking young lady like you."

"Robin is shy, Ian," Holly interjected. "She's very bright, but doesn't have a lot of experience dating. I'm here to make sure she doesn't make a bad choice."

"What would you consider a bad choice?" I asked, aiming my question at Robin.

Once again, Holly interrupted. "Some guy who's just interested in sex," she said bluntly. "Some guy with a room temperature IQ. Some guy who can't hold a conversation without saying 'you know' thirty or forty times."

I chuckled. "Okay, I think I've got the picture. First of all, you can't get into this university with a room temperature IQ. Secondly, almost every healthy male on campus is interested in sex. Some of us behave a little more gentlemanly than others. And finally, I know what you mean about holding a conversation and I agree.

"I know a young guy who is very bright, just like Robin. I can assure you he is a gentleman because he is just as inexperienced as Robin, I suspect. He's a nice looking, presentable guy who can definitely hold a conversation on a very wide array of topics. And no, he not some anti-social dork. He was part of the team that Debbie and I were on last year in organic chemistry. I would be happy to give him a call and see if he'd be willing to meet with you before you agree to a date. Would that be acceptable?"

Robin didn't hesitate in agreeing, nodding her head vigorously.

"Good," I smiled. "His name is Terry Palmer. I'll call him this afternoon and give him your phone number if you'll give me yours."

Robin left shortly afterward to catch her carpool ride, leaving Holly and me alone.