“Welcome to manhood!” Matt beamed as he walked in and sat down.
It was early October in my senior year of high school. Monday morning study hall, hanging out with my usual group of friends.
I was officially an adult now, having turned eighteen over the weekend, just a few weeks after Matt. Several of the guys at the table had been to my party on Saturday, but Matt had missed it due to a family function.
“Yeah, I got your manhood right here,” I retorted in my best fake New York accent, standing up and holding my hands just above my crotch. Jeff and Ben, sitting on either side of me, quickly shushed me and pulled me back down by my shoulders, though chortling quietly.
“Yeah? Well, let’s see it then,” Matt replied in a low but joking voice. He was the king of fake-gay flirtation. Always joking about it, even though he managed to get dates with some of the hottest girls in our school. Matt had a great personality, was nice to everyone, always had a joke ready and was one of the best-liked guys in school. On top of that, though not the best-looking dude, he was in really great shape. He ran and lifted weights a lot, but he was more strong and wiry than musclebound. Between that and his personality, chicks dug him.
“Right after school. Just for you.” That was the best I could come up with, but it was enough to get another chuckle out of everyone.
Fortunately, our study-hall monitor was known for letting everyone hang out and quietly shoot the shit, playing cards and not even pretending to study. But he did insist we keep the noise level low. And he had zero tolerance for any kind of off-color remarks, which was why my buddies had tried to keep me quiet a moment before. If he’d caught wind of my “manhood” comment, he would have split us up to actually study for the rest of the period, and the fun would be over.
A few minutes later, at a moment when we’d paused our quiet conversation to watch Mr. White discipline another group that had gotten a bit loud, Matt leaned back in his chair and declared, “My tits are sore.”
“Guys don’t have tits,” said Nick.
“Well, what the fuck do you call these?” he replied, pointing both index fingers to the general direction of his nipples. “I think I benched a little too hard this morning. And now I have a tits-ache.” Matt often started his day at the gym, so this was no surprise.
“Well, I'd say they're pecs ... but okay fine, whatever. Breasts, tits. Call them what you want,” Nick conceded.
“Exactly. And they’re sore, and they need a massage.” Lowering his voice to a sexy, conspiratorial tone, he looked around the group and asked, “Could one of you guys massage my tits after school?” Quiet guffaws around the table, and some glances over to see if we’d attracted unwanted attention.
The coast was clear, so Ben pursued this line of conversation: “You say it like it’s sexy or something. Maybe guys have tits, but on us they’re not an erogenous zone.” That was a big word for Ben, but it still was received with general nods and agreement around the table.
Matt wasn’t done. “Okay, so if it’s an erogenous zone you want to massage, my dick got a great workout Friday night, and now it’s sore too.” Fluttering his eyelashes and lisping, he asked, “Could one of you guys massage my dick after school?” Nervously stifled snickers and groans followed that. We were pushing our luck now.
Matt's blue eyes had been locked directly on me when he asked the “massage my dick” question. For a second he almost seemed serious, and it caught me off guard for a quick moment. I steered things back toward his weekend. “So who massaged you on Friday? Sarah?” This got everyone giggling again, so I continued, deadpan, “Did you compare tits with her?”
We all knew Matt and Sarah had been flirting heavily and were on the verge of hooking up. She was one of the prettiest girls in school, with a vivacious, friendly personality to boot. They’d make a great couple. Hell, they were both so well-liked they’d have made Homecoming King and Queen, if they’d been together at the start of the year.
She was pretty thin, and her breasts indeed didn’t appear large, hence the question. “Yeah, turns out my tits are a little bigger, but her nipples run circles around mine.”
For some reason, an image flashed in my mind of Sarah’s nipples dragging around Matt’s pecs in a circular motion. To my consternation, I actually felt my teenaged dick start to fill in response.
At this point, I’d never had any sexual contact with anyone, male or female. Not even had a real kiss. Total virgin in every way. I considered myself mostly straight, and as a horny teenager, I desperately wanted to get together with a girl. But I was also honest enough to know I leaned at a bit the other way too. I might not be attracted to guys in the romancing sense, nor did I have fantasies about male bodies generally, but I did have fantasies involving dicks. Especially me sucking them.
I sure loved my own dick. Not sucking it - or, as the saying goes, I'd never leave the house. Not for lack of trying, though. I couldn't quite close the gap of that last inch or so, but I still enjoyed shooting my loads into my own mouth. I liked the taste of my own cum, and often imagined myself sucking another guy’s penis and slurping down his tasty seed. I knew one day I would have to try it, even though I had no idea how to go about actually making it happen.
In any event, I couldn’t make the leap to picture myself doing it with any of my actual friends. My dick fantasies were always an abstract thing involving a stranger or at least a distant acquaintance outside my usual circle.
So the mental picture of my close friend Matt naked, with Sarah rubbing her tits on him, startled me. Especially since that mental image included more than just their chests rubbing together. In that split second, I saw his firm abs, his “outie” navel, the treasure trail of light brown hairs leading down to his bush, and ... whoa, I cut myself off right there, avoiding any phallic mental pictures lest I get a full hard-on while I was sitting with my friends.
That night, though, when I was lying in bed the image came back to me again. The whole picture, this time. As before, my eyes continued to follow the treasure trail down to his brown bush ... and this time, to his big hard cock. Of course I'd never seen him hard, but I'd seen his bare soft dick in the gym and at the pool plenty enough times, so it wasn't hard to imagine. The way he’d looked at me today … did he want me to massage it for real? I was surprised how much it was turning me on to think Matt wanted me on his pole.
As I lay in my bed I imagined him lying back on a massage table, his manhood sticking up gloriously erect. I was so horny I let myself entertain the fantasy and see where it went. In it, I dressed in a robe like a masseuse, approached him and gently laid my fingers on his prick. I wrapped my fingers around it in the fantasy, wrapping my actual fingers around my own actual prick at the same time. I slowly started massaging his fantasy dick, then he reached under my robe to reciprocate.
Being the very oral person that I am, my imagination quickly transitioned from mutual stroking to me putting his cock in my mouth. The non-fantasy me was literally salivating at the thought. So in the fantasy, I pulled away from his hand, bent down and took in my first penis. Matt sat on the edge of the table and I licked and sucked until his delicious fantasy-load filled my eager mouth. At the same moment, non-fantasy me blew my own actual load onto my chest.
I lay there, scooping my cum into my mouth, imagining it was Matt’s, and trying to sort out what this all meant. I had NEVER had a sexual fantasy about a close (male) friend before. The risk of embarrassment always made it seem too risky to try, but having the prospect in front of me changed my feelings.
Did I really want him? Even in the diminishment of desire that happens after orgasm, I realized the answer was Oh God Yes. I’d suck him like a lollipop given the chance - at least if discretion could be assured.
Which brought me to the harder question, the one I couldn’t answer: did he really want me? I still couldn't figure out if all his jokes were just posturing, or if maybe there really was something behind it. I'd sure hate to guess wrong. Matt was a pretty good guy and might not blab it all over the school, but it would make for some awfully juicy, humiliating gossip if he did.
What really tied my stomach up in knots was that we were about to see each other naked anyway. Tuesday was my one free afternoon of the week, and Matt had invited me over for a swim in the pool at his apartment complex. This was something we did regularly over the summer, but we were having some unusually warm weather for this time of year, and a swim sounded really enticing. In the many times I'd seen his flaccid cock, never had a sexual thought crossed my mind. But that was before he’d joked about me massaging it. Now our swim "date" seemed provocative ... and terrifying.
While Matt and I headed over his place the next day, I kept the conversation focused on straight-guy talk about sports and cars and music and girls we liked, especially Sarah. I realized the Friday night story was BS and he hadn’t actually gotten with her yet. He was not enough of an asshole to openly joke about her breast size if he'd actually been with her.
So I was genuinely curious if he was going to ask her out soon - and not just to test his dedication to straightness (although that crossed my mind). I informed him that she’d recently confided in me that she really liked him, and I encouraged him to ask her out. I was relieved that this kept the conversation away from gay-sex jokes for now.
In the pool changing room, we stripped down. In other words, the clothes were coming off the body I'd vividly pictured naked yesterday. There was that cock again, flaccid but maybe bigger than I'd usually seen it. It was everything I could do to avert my eyes and focus my mind away from what had happened next in my fantasy. I knew I'd spring erect if I allowed even a sliver of a sexual thought.
When we were both naked, but had not yet put on our swimsuits, he stood up, looking at me with a smirk on his face. “By the way, my tits are still sore.” Oh shit, now he was joking about this again?
"Still not massaging them. Not sexy."
I could see that his wiener, while not erect, seemed to have lifted a little. Switching to his fake-gay-flirty tone, “And so is my dick.” At that, it visibly twitched, and his smirk turned into a smile. "Which is sexy."
Well, he wasn't wrong about that. In response to this brazen flirtation, I could feel my own dick growing, probably visibly. Any more of this and I'd quickly enter the boner zone.
“So how about that dick massage? I can see you want to.”
His voice might have been joking, but his eyes and penis were serious. His nostrils flared and he sucked in a breath as my own eyes drifted down his body, replaying and comparing the mental image I’d formed yesterday. His cock had risen significantly - enticingly. And yes, my imagination had been pretty accurate. That's what it had looked like in my mind last night. If he lay down on the bench right now, it would be exactly where my fantasy had started.
“Maybe,” I said, raising my eyebrows. “But my dick is sore too.”
He smiled at me, not jokingly this time. “Fuck yeah.” Both our cocks were fully erect by now. “Let’s cool off and go swimming first,” he said, grabbing his swimsuit and awkwardly tucking his stick into it. "Then we'll see if you really mean it."
Fucking tease! Was he messing with me? Or testing me? My insecure self couldn't tell.
Anyway, we swam a few laps, which helped calm down my nerves. Still, I was so anxious about exposing my hard-on to the world that I avoided the diving board. Matt was bolder, taking a couple of dives despite his swimsuit looking awfully full. After a few minutes, we hung off the edge next to each other to catch our breath. He slapped his hand on my shoulder, sending a current through me. “Let’s go to the hot tub. We won't need swimsuits in there.”
Things will get a lot hotter in the next story.
