I Thought I Knew -- Book Three
From Jess' viewpoint
I was having lunch with a friend of mine named Ann. We’d become friends during our freshman year. And since most everyone we knew had left campus for the summer, we’d become closer. Well, what I mean is that we saw more of each other.
It was only a few weeks into summer session and I was already thinking of this as my Summer of Masturbation. Everyone I had ever fucked around with, or even thought about fucking around with, was gone until fall. It was just me and Ann. And a lot of solo jack-off time.
I was still jacking off the way I had since I was a kid. Rocking up on my shoulders. Lining my cock up right above my mouth. Licking and sucking on my cockhead until I shot my load directly into my mouth. With all the practice I’d been getting lately, I found I could get more and more of my cock in my mouth. More than I ever had before. he whole head, which felt so good, and even a little bit of my cock too. I liked that. I wondered if maybe my cock was getting longer, but when I measured it was still right at 8 inches.
I liked being able to suck on my cockhead. Feel its heat against my tongue. Taste what pre-jizz I had as it drizzled from my cocklips. My pre-jizz was really sweet, even if my cum wasn't nearly as sweet as some guys I'd tasted.
When I was wound up in myself like that with my cock in my mouth, I could smell what I really smelled like. What other girls and guys smelled when they were sucking me. And I have to say, it turned me on. Thinking about all the mouths that had sucked my cum out, All the times I’d shot. How they'd tasted me. And even swallowed me. How cool was that!
But I seem to have gotten distracted from my story. Oh ,yeah, I was talking about Ann.
I still remember when I first asked her out on a date. It was the beginning of the second semester. I don’t know why I asked her out. I wasn’t really attracted to her or anything. But we had a creative writing class together and had started talking to each other fairly regularly after classes.
One day we were talking and I asked her if she wanted to catch a movie or something that Friday evening. A guy I had been planning to go with had just cancelled. Anyway Ann said yes and we went.
I thought it was going to be a date, but it wasn’t like a date at all. More like an extension of our discussions after class. We talked about our writing projects and other kids in the class and the teacher. Stuff like that. After the movie we got some ice cream and talked some more and I took her home. I got nothing. Not even a peck on the cheek.
That doesn’t happen to me often because I usually make sure I know what the person I’m with wants from me and I’m clear about what I’d like from them. I’m not shy about talking about sex, as you can probably tell.
With Ann, the topic never came up. But somehow at the end of the evening I still expected something. It just didn’t happen. That, I figured, was Ann.
It seemed clear to me that we were meant to be friends and that anything more would only complicate our friendship. After that, we saw each other regularly for lunch. Occasionally for dinner or a movie. Sometimes I paid. Sometimes we split it. We never talked about our relationship. It just was what it was.
Now that it was summer and neither of us had anyone else much to turn to, we were seeing even more of each other.
So we were at lunch one day and all of a sudden she looked at me very seriously and asked, “Do you know my friend Paul?” When I didn’t answer immediately, she added, “Paul. He went to high school with me. From my hometown.”
“I don’t think so. Is he in one of my classes or something?” I asked.
“No. I just thought maybe you knew him. He’s taking two classes here this summer. He’s transferring and needed the hours to stay on schedule to graduate,” she explained.
I started to wonder if maybe she was getting ready to try to set me up. Then I couldn’t remember if she even knew I was “undeclared.” I guess we’d never talked about anything like that. I hadn't told her I liked sex of all kinds. With all kinds. She probably thought I was just a straight guy.
As I was trying to remember what she might or might not know about my sexual orientation, or lack thereof, she said, “We’re going out tonight. Paul and me. Second date.”
It was like I had heard each word just fine, but they didn’t fit together. Not in a way that seemed to make sense. Ann? A date? A second date? I had just completely stopped thinking of her in that way. I guess I had forgotten that anyone would.
She wasn’t ugly or anything. She was good looking in a girl-next-door sort of way. She was smart and funny. And nice. I liked her. It was just that since that first night when we went to the movies, I guess I had buried those kinds of thoughts about her.
I was kind of at a loss for words. “Do you like him?” I finally asked.
“I kinda do. Yeah,” she said and looked a little embarrassed.
“So why so shy about it?” I asked.
“I think he’s expecting something . . . you know, something more.” She couldn’t bring herself to look at me as she strained and stuttered to get the words out.
I was glad she wasn’t looking at me, because I’m not sure I concealed my surprise at the direction our conversation had suddenly taken. It was virgin territory for sure. At least for us. But maybe she didn’t mean what I thought she meant.
“Well, do you want to, you know, do something ‘more’?” Questions. I was always good with questions.
There was a long pause and then she finally said, “I really think I like him . . . a lot.”
“So . . . ?” I left the word hanging between us. I have to admit that the thought of her getting it on even with another guy was kind of turning me on. Hell, the thought of sex was turning me on. After all, I’d had nothing but my own devices to get me off for more than a month.
“I don’t have a lot of experience dating. My parents made it difficult when I was in high school . . .” and with those words she started to explain.
It seems she had been quite “smitten” – her word – with Paul in high school, but her parents didn’t “think he was right” for her. So she never went out with him. I couldn’t really tell from what she said whether he had even asked her out.
They had met again on campus this summer and her interest in him had quickly rekindled. She had gotten up the nerve to ask him if he wanted to go out. He called her a day or two later to make more definite plans.
On their first date she had let him kiss her good night “for quite a while.” Her words again. She told me how as she had loosened her hands from holding him close to her, her hand brushed against . . . How did she put it?
“As I withdrew my hand from his hip, it accidentally brushed against the front of his slacks. I could tell that he was extended.” I’m pretty sure that’s just about exactly what she said.
Apparently she didn’t do anything to help the guy out. She had no experience whatsoever with such things. And she had worried ever since that she was going to lose any chance she had with him if she didn’t “respond to his needs” this next time.
“So, you’re a guy. Tell me what I should do if it happens again?”
It popped into my head at that moment that Ann could be the answer to my dream. My nightmare. I could help her and she could help me. I didn’t know exactly how it would work, but I felt confident that it would . . . or at least that it could.
If I helped her with this problem she was having, she’d have to help me with mine, I figured. Maybe I could share with her my fears about how people would react if they knew that I had shared the intimate details of my life with thousands of guys online.
With a renewed interest in this conversation I eagerly asked, “So what do you want to do to him?” Again with the questions.
“I just want to make him happy. To have him like me. To . . . you know.” Again she could not bring herself to look at me as she said those words.
I took a deep breath as I gathered my thoughts and then plunged in. “Well, if your hand should again . . . by accident . . . brush against his extended . . .” I hesitated myself as I searched for the right word. Without thinking about it, I let the back of my hand brush against my crotch. I felt my cock respond. This conversation was starting to turn me on.
Fortunately, Anne couldn’t actually see what I had done because the tabletop between us blocked her view. But I think she got the idea. I guess I figured it didn’t really matter what she saw me do at this point, so I kind of brushed my growing cock with the tips of my fingers a few times as I continued, “If your hand should again brush against his penis, let it pause there. Just let your hand rest on it for a moment or two. If he doesn’t do anything to show you he’s uncomfortable with that” and I’m thinking fat chance of that, “wrap your fingers around it and hold it. You can squeeze it gently.”
I made an appropriate squeezing gesture on my own cock, which was now pretty hard and felt good in my hand. I could feel its heat. Its solid mass. Its throbbing pulse. I was feeling horny.
I had to sort of adjust myself to make more room for my growing cock. Ann didn’t react. I guess she must not have realized what I was doing. She couldn’t see it. Just some movement in my upper arm.
Then thinking more of me than of Ann’s would-be boyfriend, I added, “Maybe stroke it up and down it a little. I think he’d probably like that.”
Suddenly I’m wondering what the hell am I doing? This is crazy. I’m sitting at lunch in public telling this girl, this friend, how to jack a guy off. And as I tell her, I’m jerking myself off in the seat across from her.
“That’s all I need to do?” she asked me so innocently. It was all I could do not to freak or burst out laughing. But I did great. I stayed in my good-friend mode.
“Yeah. I think that should do it,” I said, trying to extract myself from this conversation before I came in my pants. I was also trying to think ahead to how I could move things along so I could suggest that I had questions to ask her. Questions about my problem.
But the time just didn’t seem right and so I figured I could ask her later. In the end, I just said, “Good luck with that tonight. Let me know if I was of any help. I hope you’re both, you know, happy with the outcum.” I kinda stressed the “cum” part, bit I don’t think she got the pun.
“Gee, thanks,” she said as we prepared to leave and head our separate ways.
Gee? Does anyone say “gee” anymore?
I was standing at the counter to pay our bill. Ann walked up and stood close behind me. Too close really. I kind of jumped when I felt her warm breath on my ear. Was she gonna kiss me or what?
I froze. I didn’t know what to do. “Jess,” she whispered in my ear too quiet for anyone else to hear, “I hate to ask you this, but do you think you could show me how? This afternoon? I really want to . . . you know . . . get it right and everything.”
I didn’t answer. Hell, I didn’t move, or even breathe. But my cock was suddenly hard again.
“Please!” she begged. My cock twitched. What the hell was going on?
If it wasn’t for the dream and my fears and the feeling . . . no it was more a belief or even a certainty . . . that Ann held some part of the solution to my dilemma, I could have made up an excuse. Any excuse. And gotten the hell out of there.
At least that’s what my head was saying. My cock was thinking, easy sex. Easy sex!
I guess I was thinking with my cock again because what I said was, “I’ll see what I can do. What time?”
Even as the words left my mouth, I started to doubt whether Ann could help me in any real way with my problem. But my cock seemed mighty pleased with the prospects of what it might mean to help her with her problem.
“3 o’clock at my place would be great,” she said and flashed me a big and very genuine smile before she gave me a little kiss. On my cheek.
As I headed back to my place, I started wondering what the hell had I gotten myself into. What did Ann expect? Was I supposed to demonstrate what it’s like when a guy . . . hell, when a guy blows his load? Does she know shit about all this? About any of this? How basic do I have to get? I could show her videos from some of the porn sites. She’s probably completely clueless about such things. That’s what I was thinking.
As I reached my apartment, I started to wonder if maybe, just maybe, she would possibly . . . Could she want to practice on me? To jerk me off? No, she just wanted to make sure she understood what to do. What guys like. To try to understand what it felt like. At least that’s what I thought. I really couldn’t quite get my head around Ann jerking anyone off. Certainly not me. But my cock seemed to have ideas of its own. I gave it a squeeze.
Then it popped into my head that maybe there was no boyfriend. No Paul. Maybe she was just trying to, you know, have sex with me.
I thought about that and every other possibility I could come up with for the next two hours until it was time to go. I even thought back to when I was in high school. How Justin, the only gay kid I knew at the time, had taught me about such things. Like how to give a good blowjob.
Oh, man, Justin sure did give good head. I loved the way H.R. wrote that part. I couldn’t resist reading it again:
Justin cupped my cock and balls in both his hands and then leaned forward and started licking. First my cock and then my balls. Then back to my cock. He was right. He was good at this. I thought Billy’s handjob was nice. This was better.
I didn’t need to tell Justin I liked it. My cock was already telling him as it stretched out in his hands. Wet with his spittle, he was now gently stroking my cock, licking it, stroking it. God it was getting hard really fast. Standing straight up, presenting its sensitive underside to his tongue, giving him a rock hard column to stroke and lick.
And then he said, “Ready?” I didn’t know what he meant, but before I could inquire as directed, he had begun to suck on my cockhead, slurping it in and out between his lips. I looked down and he was looking up, my cockhead in his smiling lips. His fist wrapped gently around my shaft. His saliva dripping down around my nuts. I was fascinated by the view. I loved the sensation.
He stopped and lifted his head enough so my cock was standing free just in front of his warm, welcoming lips. “Remember what I’m doing. Go slow. Watch your teeth that you don’t scratch him. Dicks don’t like teeth.”
I could feel his breath on my cock as he talked and couldn’t resist leaning forward to get my cock closer to his lips. So this is what blowjobs were like?
And then he started again. I gasped.
“Are you going to cum?”
“No,” I said. “Not yet.”
“Let me know if your gonna cum. That’s important.”
And he went back to caressing my cockhead with his lips, stroking my cock with one hand and now pinching one of my nipples with the other.
I pulled away suddenly, almost in a panic. “I don’t think Billy’s gonna go for this. Maybe a blowjob, but not the stuff with the nips.”
“OK,” Justin said reassuringly. “You should focus on his dick, if that’s what you think he wants, but don’t be afraid to ask him. You might be surprised.”
Justin looked a little discouraged, but then smiled reassuringly. “Just relax and try to enjoy it. Remember, you’re doing this for Billy, not to Billy. So make it as good as you can. Now relax.”
And he started again, minus the nipple. Before long he started to take my cock deeper into his mouth. In and out as his tongue played all around my swollen cock. I could see why guys went crazy for this. I watched as my cock went deeper into his mouth. I felt my sensitive cockhead being stroked by the roof of his mouth, caressed by his warm, slippery tongue. It was so wet. So welcoming. So warm.
He started to hum gently almost like a cat purring. And I felt the gentle vibration in my cock. His lips smiled as my hard meat slipped in and out. In and out. I couldn’t resist. The urge was too strong and so I started to pump my cock deeper. It must have been going down his throat. That’s what I could feel. I was fucking his throat. I could feel the surge building in my balls. I could sense every muscle in my body contract.
Then I exploded with a massive blast of cum. “I’m cumming,” I shouted and shot again and again. I could see Justin swallowing, but still cum was dribbling from the edges of his mouth. I could see it on his lips. His lips swollen from sucking on my cock. That was my cum. On Justin’s lips. My cum. His lips. Down his tight throat. Fucking A. So this was being gay.
As I looked into his eyes, I again had that great view of my still rigid cock deep between his lips, his smiling face looking up at me. My cum dripping from his mouth. On his lips.
He pulled back and my cock stood free. It felt cold in the air out of the comforting warmth of Justin’s mouth.
By the time I finished reading that, I was so hard. It may seem kinda weird, but reading this had turned me on. My own story in pretty much my own words with a little help from H.R. It had gotten me really hard.
As I sat their stroking my aching cock, I began to realize that it wasn’t just remembering what had happened between me and Justin that had gotten me so hard. It was the idea that we were changing places. I was gonna be the teacher. I was gonna be the one to show Ann how to give Paul what every guy needs.
There was something so . . . I don’t know. Just the idea that I was gonna be teaching someone else how to get a guy off was what really turned me on I think.
As I stroked my cock, all eight rigid inches of it, I started thinking with my head again. What I should do is make this as good an experience for Ann as Justin had made it for me. I wasn’t quite sure how I was going to make that happen, but that was my new goal.
And I started telling myself, Whatever happens, it’s just sex. You’ve done it before and you’ll do it again.
To Be Continued . . .
I hope you enjoyed this chapter. Jess and I are starting this story off kind of slow to get you into the frame of mind he was in when it happened. Believe me, you are going to enjoy reading what happened to Jess that summer.
Leave us a message. Let us know what you think. And until next time, stay happy. And stay hard!