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TRUE FIRST TIME TALES
Colin's TaleRated: X ages 18
I wasn't gay and I'm still not, but since I just had sex with the second guy ever, I started checking around about first gay experiences and found Ray's stories and wanted to tell about mine. I'm twenty-one now and going to college and just messed around with a guy I know here at college. It was pretty fun, and it reminded me of my first time with a guy three years ago.
We had graduated high school almost two months previously. I'd been dating a nice girl for almost a year, and she got really pissed that I didn't want to follow her to the college she was accepted at, so we broke up. Well, she decided that since I wasn't going to throw away my future to follow her to a college that didn't have the degree program I wanted, that we didn't belong together. Chicks are so emotional and irrational!
She wasn't my first girlfriend at all. I don't want to sound like I'm bragging, but I'm a pretty hot dude. I got my first hand-job from a girl in ninth grade, my first blow-job a couple months later, and my first piece of pussy not very long after that. By the time I'd graduated high school, I'd had four girlfriends and done everything.
So with a couple weeks left before I headed off to college, I'd been dry of any action for over two months. Kind of a record since I first got some action about four years before that. I was pretty horny. A buddy had his going-to-college party, and had beer and weed. So I'd had a few beers and hit a few joints, and I was buzzed pretty good. I tried to get a chick I hardly knew at all to fuck in my car, but she didn't even give me a handy and wouldn't let me even finger her off. So I was pretty worked up, buzzed, and figured I go home and beat one out. It was only nine on a Saturday, though, so I drove around some first. I was leaving for college next week, and not having any going-away party, so I felt like cruising the town and having a sort of last look at the Saturday night scene. Maybe I'd find some chick and get some action, ya know? So I shoved a hand down my pants and toyed around, keeping it hard and ready in case I saw a chick looking like she was on the hunt.
I should mention that we live in a small town, with barely enough people to have a high school, so almost everyone knows almost everyone. I'd had different friends back before high school. I'd hung around with a different crowd. Now I was one of the more popular guys, good looking, a jock, and all that. Back then, that stuff didn't matter to us and I'd had this friend who lived almost next door, Oakley. Yeah. Dorky name, right? He was dorky, too. Not a total geek, but he sure didn't fit in with the more popular guys I ended up fitting in with during junior high. We'd been pretty good friends, but different cliques split us apart. I ended up sporty and athletic, he'd ended up dorky and brainy.
So, I was cruising around, looking for some pussy, and who do I see walking out of the little gaming store? Oakley. It was this little store for comics and role-playing games and that kind of dorky stuff. He was talking to a couple dudes, then they went one way and he headed the other - toward where we lived. It was kind of sprinkling rain, and he was getting wet, and I was sort of... I don't know, feeling nostalgic? I knew his folks weren't doing well money-wise, and he didn't have a car, so I rolled up next to him and rolled down my window and called out, "Hey, Oak. Need a ride?"
He sort of shrugged then walked up to my open window.
"No big date tonight?" he asked and sort of laughed, leaning over to block the drizzle from getting in my car window.
"Nope. We broke up. I was sort of cruising for some action, but it looks pretty dry. At least that way. So, you want a ride home?"
He walked around the car, took his coat off and shook the rain off it before he got in. The guy was a class act, even if he was a dork.
"Thanks for not soaking my seat," I said as I put the car in first and started off.
"No prob. I wouldn't want my car seat soaked either. If I even had one."
"You not getting one for college, even?"
"Nope. Besides, there's busses and campus transportation."
He was going to a way better college than I was. I'd heard he gotten a really good scholarship and package. That made me think some, as we headed toward our neighborhood in the rain.
"I probably should have stayed friends with you and Kevin. I would've had better grades. Might have gotten into a better college," I thought out loud.
"Nah. You're too good looking to hang out with us dorks," he laughed. "Besides, you never got into gaming or anything either. You got into sports and stuff. We were just were way too different."
"Yeah." I thought about stuff some more, and just as I turned onto our street, I said, "I do miss the way we hung out when we were kids. We had a lot of fun."
"Yeah, we did. Remember my twelfth birthday?"
That made me laugh. We'd gotten into so much trouble that night! It'd been a riot.
"Yeah, good times, man," I sighed.
When I pulled up in front of his house, it brought back a few more memories. I'd had some good times there. We ended up talking about a lot of them. We were both heading off to different colleges so soon. Whole new lives. So we talked about a lot of things in our shared past as kids.
"There's no lights on, so my folks are in bed. You wanna sneak in? Sorta like we used to?" he asked, laughing.
It was really funny, so I said, "Sure!"
We got out of my car and pretended we were sneaking into his house, the way we used to. The rain was really slow and soft, almost just a mist, as we quietly 'sneaked' around to the back. I was surprised that the basement window was still able to be jimmied that way, but he opened it, and we crawled in and onto the big wooden hutch below it, then onto the couch beside it. He was even able to sneak silently across the room and turn on the light.
"You still sneak in or something?" I asked, blinking against the bright light.
"Yeah," he laughed. "Sometimes."
The room looked almost exactly the same. Same kind of furniture in the same places, for the most part. He got two sodas from the old fridge and we sat down on the couch. It didn't feel like old times, but it did, too.
Pretty soon we were laughing and having a great time. He mentioned my last girlfriend and asked why we weren't still going out. I told him why, and he agreed women were too emotional. Then he really freaked me out. Sort of.
"That's why I don't like chicks," he said.
I sort of shook my head, and asked, "What? You gay or something?" mostly in jest.
"Yeah, I am," he said, looking me right in the eye.
This was sort of a surprise, and sort of not. I hadn't totally ignored him and Kevin since I'd moved into a different group of friends, so I was sort of aware he hadn't dated anyone. Kevin had, and was still dating the same chick. But Oakley had never went out with a girl. I had wondered a couple times, ya know? Just wondered. But now...
"You're really gay?" I asked, like some idiot.
He nodded, then said, "I told my folks, and Kevin, but nobody else. Except you, now."
"Oh. Wow. Cool, I guess."
It got awkward and quiet. I was figuring how to leave without being rude.
"Can I tell you something else?" he asked.
I looked at him and saw he was looking at his hands and fiddling with the pull-tab on the soda can, sort of nervous like. I figured I'd be nervous too if I was telling someone who used to be a friend that I was a homo.
It'd been great catching up and talking, and I sort of felt like we could be friends anyway. I mean, we'd been friends all through our youth. Maybe we could be friends again as adults. Maybe stay in touch through college and after. He was a nice guy. And I didn't have anything against gays at all. It was 2018 after all.
"Sure," I said, doing my best not to look away from him.
"I'm not the only gay guy in town. I mean... you know... I sort of had a boyfriend for while."
One I could see, even knowing that one, but two?
I knew not to ask who, but I didn't know what else to say, so I had to think for a bit before I asked, "Still... uh... dating?"
"Nope. He already left for his school. Won't see him again until break or something."
"Oh. So, staying boyfriends?"
He laughed, then said, "We think probably not. I mean, we weren't into each other, or anything. Just... we're both gay, ya know? So it was... just... convenient."
Now what do I say?
Then he said, "Besides, I've always sort of liked someone else."
It was the way he said it. Slow and intentional, his voice really shaky. And the fact he kept glancing at me and then away and then back. I felt my insides sort of shift.
I'd never thought much about there actually being a gay guy in school, let alone in town, let alone knowing him, let alone even more that gay guy at school being in my grade and liking me. It was really... weird and strange and awkward and frightening and flattering.
"Me?" I barely asked.
He nodded while looking at his hands and that can of soda in them.
"Since when?" I asked next.
Pretty much the time I'd started hanging out with others and was spending less and less time with him and Kevin.
And we'd had gym together that year. We'd had lockers next to each other for the first couple weeks, but then my new athletic friends had asked me to move over to their row of lockers.
I'd left him alone in that row of lockers. He'd made a couple friends, though, and had moved to be with them in a couple more weeks. I'd sort of kept an eye on him. In a way.
So, he'd seen me naked all year long in seventh grade. And again in tenth grade gym. But not since. I was sort of relieved and sort of... I don't know. It was too weird.
I needed to change the subject off of me.
"So, just the one boyfriend?" I asked.
"Well, you're no virgin, then," I laughed, needing something else to say.
"No, that's for sure!" he laughed.
I wanted to know, but I didn't know if it was a 'cool' thing to ask about or not. But I couldn't think of anything else to ask or say.
"So, who was the girl?"
He shook his head and said, "We took turns."
Somehow, we ended up talking about sex. I mean, graphic stuff. I was still buzzed from the beers and pot, so I guess that helped. Man, I had no idea. He told me how he loved rimming, both getting and giving it, and how awesome it felt. He told me ass was tight and hot and felt all velvety inside, and probably felt just as nice as pussy. He said cock tasted like salty skin, and cum tasted like salty, bitter mushrooms, and he liked it. He swore that guys could give better head than almost any chick, and he knew that because his boyfriend had been with a couple girls to hide he was gay and told him all about how girls didn't know what things felt like, but guys knew what felt good and where and how. That's all just the tip of the iceberg of information he slammed me with. Edging, prostate massage, sounding, tons of things I'd never even heard of. Well, I'd heard of some, but sure never experienced any of it.
Hell, he'd only been with one dude, but he'd done so much more than I had with all four of the girls I'd been with. So that's what I told him.
He laughed, looked around and back at me a little, then said, "We can fix that."
I instantly knew what he meant, but I still said, "What?" without thinking.
"I could show you what you've been missing out on," he said, managing to look right at me. Then he said, "I've fantasized about showing you. A lot of times."
I couldn't think of anything to say to that. I wasn't very interested. I like girls. I like tits and pussy.
Not that I hadn't actually thought about jacking off with someone before. There'd been this time, staying over at a friend's place, when I'd thought about jacking off with him. He wanted to look at porn on his computer and jack off, and said he wouldn't think it was gay if we both did it at the same time. I'd turned that down, and watched some porn on my phone while he whacked one out on his computer. I'd gotten pretty boned, and really thought about jerking off too, but I just couldn't. That was about two years before.
And I hadn't been stoned, a bit drunk, and hot and horny from a make-out tease in my car earlier during a two-month dry spell.
I actually thought about it. I mean... so Oak was gay. I sort of suspected for a while. And we'd been good friends for years. And I was horned up. And buzzed. And still a bit stoned.
I asked, "What would you do?"
He smiled, then said, "I'd show you how it feels when you get all worked up for a few minutes first. Then I'd show you how awesome being rimmed is. Then how good it is having your prostate massaged. And then how good a guy can give head. How much better it is when you get edged a couple times. Then how awesome a blow-job is while you get your prostate rubbed at the same time."
Then he finished with, "Any of your girls ever swallow?"
"One. Once. Why? Would you?"
"I would. And after a couple edges, and some prostate massage, and some rimming, and maybe some sounding, you'll cum so hard you'll lose your fucking mind."
I didn't like the idea of being sounded, but everything else sounded... well...
"Would I have to... you know..."
"No. You don't have to do anything to me if you don't want to. I know you probably don't. Just let me show you what I know, and if you don't like something, say so and I'll stop doing it."
I was actually thinking about it!
He added, "I've always wanted to with you. Since seventh grade. And... well... this is the last chance. Ever. After we go to our colleges, we'll probably never see each other again. I'll never have the chance again... with the hottest guy I ever knew."
I was actually thinking about this!
I was even getting hard!
Then he added, "All you gotta do is just sit there and enjoy it."
I was really thinking about going for it.
"I promise..." he said firmly, "It'll be the best time you ever had. By far."
I believed that. I just wasn't sure how I would handle it after. Ya know?
Hell, in a week I'd be out of state. He was right, we'd probably never see each other again. Maybe at a school reunion in ten years. Maybe not.
Who would ever know?
"If I say stop, you will?" I asked.
"I promise. I just want to show you what you've been missing out on. You deserve the best time I can give you, man. You were a great friend. Even when you made other friends, you still nodded hi and stuff. You never ignored me or treated me like an ass or anything."
He was sure making me feel good about stuff.
"Plus I've wanted to with you for so long. Just once. And this the last chance. I can't let it go by without at least giving it a try. I mean, what's the odds we'd spend any time together right now? After four years, and on the last weekend before you head off, and I head off the next weekend, and we'll probably never see each other again. And here we are, in my basement again, sort of like old times. If I don't take the chance now, I'll just regret it forever."
Would I? Would I regret it if I didn't? I thought about how most guys will do something with a guy friend at least once before college. Often more than once, sometimes with more than one guy. It didn't mean I was gay.
Hell, I KNEW I wasn't gay.
I laughed, mostly out of nervousness, some out of making up my mind and having that pressure relieved.
"Okay. But I don't think I'll do anything back. Okay?"
His face lit up, which made me feel good about my decision and myself.
He said, "You don't have to do anything. Just sit there and let me do everything."
I nodded, and by the time I had, he was sliding onto his knees between my legs. He pushed my knees apart, got up close, and rubbed his hands up my thighs.
He looked up at me, all smiles, and asked, "When was the last time you got off?"
I laughed and nodded. Man, his hands felt great softly rubbing up and down my thighs, inside, top, outside. My dick was surprisingly hard! I sort of expected it might take some time to get really hard with a guy down there, but it was already totally boned up and starting to throb harder.
The funniest thing was how I noticed how happy he looked. I mean, I'd never seen him look like that before. We'd been friends as kids for years, and I'd seen him smile and be happy a lot. But right then he looked so amazingly happy - almost overjoyed or something.
He sat up on his knees, and now I could see how excited he was. His erection was clearly pushing hard against his jeans.
He asked, "Can I take your shirt off? Please?"
It was kind of embarrassing, but I nodded. He grinned more, if possible, then reached up and lifted the tail of my shirt up, then over my head, and off over my arms. He folded it really quickly and put it aside. Then he put his hands on my pecs and fingered my nipples. Man! I actually shivered!
"Any of the girls ever play with your chest?" he asked.
"Sort of," I answered.
But it hadn't felt like this. It'd been nice, but really fast and I was looking forward to what was next and what my hands were doing to her tits. This time I was sitting still, and an old friend - a guy - was doing it. And doing it so... purposefully? It wasn't a sort of step to something more, it was more like something intentional. It was more... intense!
The way his fingers played with my hardening nipples was really nice. He seemed to know what to do, and how to. It was... good!
His hands moved to my sides, and slid down, and across my stomach, and back up.
"Man, Col, you really have the best bod, man," he said in a heavy sigh.
I wanted to tell him how good what his hands were doing felt, but it was awkward and weird.
I noticed his bulge again. It was so obvious how hard his dick was. It was aimed up to his right, and looked pretty impressively long. It was sure hard!
And it was kind of... flattering? I mean, I was making him that hard. I was making him that excited. I had been, since seventh grade.
Yeah, flattering, for sure.
And kind of nice. I mean, I turned a guy on. Not only girls, but guys, too. Well, one, at least.
And his hands were sure turning me on! I'd never had a girl rub and massage my chest and sides like that. It was probably the most sensual thing I'd ever felt.
His hands moved down my chest, smoothly and gently, but firmly, too, down over my stomach, and then over my thighs again.
My body shivered again!
I hadn't been this turned on since my first few times!
"Can I take your jeans off now?" he asked, smiling up at me.
I nodded. My dick nodded, too! And as his fingers worked at the button and then the zipper, my dick tried to squirm out of my underwear.
I lifted my ass off the couch as he pulled my jeans down. He pulled my shoes off, then my jeans. He folded them really quickly and put them to the side with my shirt. Then he sat back on his heels and looked at me in my boxers. Big, wide smile on his face.
He sat there looking for long enough that I asked, "Something wrong?" and thought about asking if he'd changed his mind.
"I just want to be able to remember this," he answered, sort of laughing nervously. "It's the hottest sight ever, and I want to be able to remember it forever."
Man, he could make a guy feel good about himself, even in this hugely embarrassing moment.
I put my hands behind my head, sort of posing for him. He laughed, so I did too. It was kind of relaxing in a way. It took a lot of the awkwardness out of the moment.
"Do you always wear briefs under your boxers?" he asked.
"How can you tell that?" I asked, looking down at my lap. The fly of the boxers wasn't open, so how did he know?
"The shape. I can see the bump where you're hard, but if you didn't have briefs on under the boxers, there'd be a different kind of bump there," he said, grinning so widely.
His hand reached out and landed on my lap, squarely on my bulge. He gently felt around, finding the hard head of my dick. He followed the shaft down to the base.
"I knew it'd be nice and big!" he sighed.
Then he cupped my balls and felt all around them while his other hand smoothly slid up and down my thigh.
Damn! I'd been felt up by girls plenty, but not like this! Huge thrills ran amok all around my guts and back and chest. And everywhere his hand roamed on my thigh, and all through my groin as his other hand thoroughly explored there.
"Can I take your boxers off?"
I nodded almost violently!
He slid them down so slowly that it had to be completely intentional! Almost an inch at a time!
I was really embarrassed at the wet spot on my white briefs. He quickly folded my boxers and put them on my jeans. Then he slid both hands up my thighs and held them there as he leaned forward and over my lap until his face was nearly buried in my groin. I heard him inhale deeply, and again. Then he nuzzled my hard head with his nose! I almost jumped! My dick sure did! I mean, it went haywire for a second! My legs bucked once, too.
This was intense!
"You smell so gooood," he groaned as he ran his nose around my hard dick through my briefs, while his hands gently massaged my upper thighs.
His hot breath was like volcanic fumes as it spread out over my briefs. Then I felt that warmth move up above the waistband of my briefs. Then he gently kissed my treasure trail there. Then he moved to the side, doing the same. It felt so good! I realized he was gently licking an inch, then sucking his lips tight against the skin there, then flicking his tongue across the skin trapped between his gently sucking lips. Then he'd move a few inches and do that again somewhere else as his hands slid over my skin side to side and across my front. Kiss and suck, side to side, then up a bit and side to side, again and again, hands rubbing all over me, until he was at a nipple. Just as I thought he was about to do that to my nipple, and my body was tensing for that pleasure, he skipped over it and landed on the other side of it. Dang it! Then he neared the other nipple, and just as he was about to skip over it, he didn't! He landed right on it, sucked onto it, and flicked his tongue over it.
I gasped out loud as huge tingling thrills exploded all through my chest and guts!
He sucked it harder, licked it harder, even gently nibbled it with his teeth and lip!
I groaned a bit by accident as my body trembled.
He stopped and looked right at me. He said, "Please make noises? Please? It let's me know you like something. Okay? Don't be embarrassed. Okay? It feels even better when you let out the sounds your body wants you to make. Okay?"
I nodded, but wasn't sure I could.
He kissed my chest again, and slid over to the other nipple and repeated the suction, flicking, and nibbling.
It was right then that I noticed that I was breathing fast and hard, because I groaned but needed to breathe immediately after.
Holy shit could he turn a guy on!
His hand slid up my sides, and over my pits. That was new, for sure! No chick had ever touched my pits. He actually tickled the hairs, and then slid up my arms. Oh, wow! Who knew that would be hot? His hands moved from my elbows to my hips, sliding smoothly back and forth. It was like... there was nothing it was like! It was tickling but sensual and just plain hot!
Then he was kissing down my chest, over my stomach, and then he pulled my briefs down with his teeth! He let it go just hard enough to snap against my hard-on firmly enough to make my body jerk in surprise and pleasure!
Then he was licking my head! Oh, fuck! His soft, warm, wet tongue wiggled firmly and gently against the sensitive area beneath my head, following the contours and edges, making me groan and stretch and pant for air.
His tongue cleaned the very tip, toying around in the hole there. Wow! My dick was almost bending in half! It was easy to let out those moans now! So I did.
Then his hands were pulling my briefs down my legs. I helped by lifting my legs and pulling my feet out of them. He put them on my boxers without looking away from my groin. He leaned forward again, and sucked my left nut into his warm mouth.
None of the girls I'd been with had ever done that! And it felt great! He suckled and rolled it around in his mouth, then did the other one. Wow! All the time, his hands were roaming all over my body. My dick released a pulse of pre-cum. He immediately slid his tongue up the underside of my dick, over the head, and without sucking at all, licked my head clean with his lips and tongue. My dick was throbbing so hard I could feel it inside behind my balls!
He slid his hands down to my knees, then lifted them upward. He sort of pulled me down the couch cushion a bit, and then kissed the inside of one thigh then the other, higher and higher, until his face was between my thighs and his nose was behind my sack. And then I felt his warm, wet, slippery tongue behind my balls and between my legs and...
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