Jess' Story I Thought I Knew -- Book Three Chapter 3 From Jess' viewpoint
I tried to act cool and relaxed as Anne let me into her dorm room right at 3. I noticed her name by the door. I never knew it was spelled with an "e" on the end.
She thanked me over and over again. Even gave me a big thank-you hug. For some reason she quickly pulled back mid hug and seemed to blush. I think she probably had detected the not-so-slight bulge in my shorts. I couldn't seem to get it to go down and she had inadvertently been pressing her body against it.
"This is so embarrassing for me," she said. "And for you, too, I'm sure. We really don't need to do this. I think I know enough from what you told me. You're such a friend. Really, we don't need to do this."
She looked a little awkward, but then smiled again and offered to get me a Coke or something. I declined and tried to show her my it's-all-cool act.
"Don't worry. It's no biggie," I said nonchalantly and then sort of cupped my junk in my hand like . . . I don't know. I don't really know where that came from.
There were two single beds in the room like in a lot of dorms. But since it was summer she had the room to herself. I sat on one bed. She sat on the other facing me. I thought back to when I was sitting on Justin's bed. I could remember how uncertain and probably afraid I was. But how curious too. And how hard I was that fist time. You know how you can get so hard it almost hurts. Your cock just aches from the strain of being hard, but it feels so good. You just want to stay that hard forever.
I was starting to get hard like that. Hard enough that all of my thoughts were channeled through the stiffness in my cock. Its throbbing. Its heat. Talk about thinking with your cock. I was doing everything with my cock. I wasn't gonna turn back now.
I think I was so determined because . . . Well, sure I wanted to help Anne, but . . . No guy wants to spend his summer jerking off alone in his room. So I guess it was really both things. Help Anne. Get off. And, oh yeah, get her to help me with my other problem.
But I really did want to help her. To return the favor Justin had done me in some way. I really think that was at about the top of my mind.
"So what can I do?" I asked. Always with the questions.
"I just want to make sure I'm not making a big mistake with Paul. I don't know a whole lot about boys and their . . . penises." She said "penises" like it might leave a bad taste in her mouth. Who knows, I thought, maybe it will if Paul gets lucky.
"So what can I do to help you exactly?"
"Well, I've been wondering if what I thought I felt in his pants . . . how can I be sure I actually felt his . . ." She hesitated again at the very word. ". . . his penis?"
"What did it feel like?" This was gonna be easy, I thought. I just need to keep asking questions.
"I'm not sure it was him. That he was extended. How can I know for sure? Maybe he wasn't and . . . I don't want to scare him away, but if he expects me to . . ." She just couldn't finish the thought. This was really hard for her.
"Well first of all, guys don't call it extended. They say they're 'hard,' or they're 'sporting wood' or 'sprung a boner,'" I told her. "But if a guy is hard, it would be like he had a hotdog in his pants or, if he's lucky, maybe a Polish sausage."
"Oh," she said and her eyes widened. Then her expression changed and she looked right at me. I think she was scared and confused and probably feeling, I don't know, like guilty or something just to be talking to me about this stuff.
"So where would it be?" she asked in the shiest little-girl voice and glanced down quickly to check out my crotch. I'd gone a little soft and maybe she couldn't tell I was still semi. Those shorts I was wearing make kinda like folds that can hide it when I'm sitting down.
So using my thumb and index finger on both of my hands, I leaned back on one elbow and held my dick through the fabric. That made it stand out quite clearly.
She quickly looked away.
"It's OK to look at it. It's perfectly natural. Guys get hard all the time. Go ahead and look at it."
But Anne didn't look. She blushed again. Then she put on a forced smile and said, "You are so good about all this. I don't know how to thank you."
She glanced at my crotch for a second and then looked away.
"So you can see just where it is?" I asked.
"I didn't think it would be so big," she said. Now I have to admit that sent a jolt of pride to my cock.
It was awkward sitting there not sure what to do or what to say. As I tried to figure out what my next move should be, I was suddenly thinking about Justin and all he had taught me. I could remember so clearly looking down as he sucked my cock that first time. The memory was so clear I could almost feel his lips on me at that very moment. Almost feel the tension I had felt.
I let my head drop back and closed my eyes. The memories in my head and the sensations in my cock were combining to almost overwhelm me. It was hard to know the difference between what I should do and what I wanted to do. If there was any difference at all.
I took a deep breath and looked back at Anne. She was so uneasy with what was happening, but it was what she had wanted. She had asked me to do this for her.
"It's OK. You can touch it if you want," I said. It was my turn to be Justin. To be the teacher and take the lead. It was my turn to help liberate someone else who was so twisted up in their sexual hang-ups and fears.
I guess I'm not as smooth as Justin at these things, because without even looking at me Anne stood and said, "I can't. I can't do that." She turned away and walked to the window where she stood silently looking out at nothing.
Seconds passed. Maybe minutes. It was awkward and I knew if someone didn't speak soon, if something didn't happen soon, I'd just have to leave. And that wouldn't help Anne. It wouldn't help Paul. And it wouldn't help me.
Just as I thought time was about to run out, I asked, "Do you have a picture of Paul?" I'm not sure where the question came from or why, but it seemed to do the trick.
With her back still turned toward me, Anne sort of twisted her shoulders and seemed to stretch her arms at her sides. She turned her head from side to side trying to stand as upright, tall and proper as she could. Then she slowly turned around to face me.
Our eyes locked. She wasn't going to look down at my crotch. No way.
"Sure, I do. Would you like to see it?" she asked.
I nodded yes and watched as she walked over to her desk and opened her laptop. She sat down. Click. Click.
I got up and stood behind her, looking over her shoulder.
"It's his high school graduation picture," she said, looking up at me.
It was a picture of a kinda geeky guy with bad glasses. It looked like maybe his mom or his dad had cut his hair. Not good! Typical geek yearbook picture.
"He's cute, isn't he?" Anne said. The smile on her face told me exactly how much she was into this guy.
I just nodded.
Click. Click.
We were looking at another picture. A guy bare-chested. Looking tan and fit and really pretty damn sexy. I could barely tell it was the same guy. But it was. I knew it was.
"That's from a couple of weeks ago when he was playing touch football with some friends back home," she said.
"He looks . . ." I searched for the right word. I wanted to say sexy, but that didn't seem quite right under the circumstances. I finally managed to say, ". . . older."
"Yeah, he does, doesn't he?" she said, again smiling in that way that told me so much about her feelings for him.
"So that's the guy you . . ." I didn't finish the thought out loud as I got up and walked back toward the bed where I had been sitting.
She followed me and sat across from me once again.
She looked at me kinda nervous like is something gonna happen now?
"You want to make him happy don't you?" I asked.
Seeing his picture had once again sent a charge to my cock. I sure as hell wasn't having any trouble staying hard that afternoon.
Anne nodded agreement but didn't say anything. She just stared like over my shoulder.
"Then you need to know how," I said. "You need to know what to do."
She didn't respond at all.
"Give me your hand," I said.
There was a long pause again and then at last she raised her right hand from her lap where it had been resting and closing her eyes she held it out toward me.
I took hold of her hand. It was cold and trembling. Even with her eyes closed, Anne looked like she might cry.
As I lowered her hand toward my crotch and my waiting, eager hard-on, it was like I could feel my heart beating in my cock.
Images started swirling in my head. Justin and me. Anne and Paul. Paul and me. All of them variations of the same handjob. All with their own images, but all mixed together. All equally fascinating to me. It was like I couldn't really sort them out.
Was this just one more time when I was thinking with my dick? I didn't know where this was going, but I didn't really care as I felt Anne's hand resting on my cock. Just the fabric of my cargoes separating the two.
I closed my eyes and thought, It's time to be the teacher.
To Be Continued . . .