Young and Naive

This is a work of fiction involving the following themes; gay, first time, twink, bear, chastity, oral, anal, young with older

It was 1989 and I was young and naive, on my own in the city of Halifax for the first time. It was my second year of university, but the first year I had lived with a bunch of friends from my hometown, and rarely went out at night on my own. This year I had my own apartment, and so I spent more time wandering around by myself.

This one evening, I had been out with my friends having a few drinks downtown, and when they all left to take the bridge back to Dartmouth, I started walking home to my apartment in the north end.

I had heard rumours that guys cruised for sex at night around the Citadel, a large historical site in the middle of downtown, but I was extremely naive and inexperienced, and didn't really know how that worked, or even what part of the park they used.

In any case, I wasn't going through the park, I was taking a street along its western boundary, so I wasn't expecting anything but a long walk home.

The street was tree-lined and dark, with little traffic, no buildings or driveways. Looking back at it now, I can see it was the perfect place for cruising, but at the time, I had no idea.

As I was walking along, already wishing I had the money for a cab, or that I had left in time to catch the last bus, a car pulled up alongside me and stopped. I went over, wondering what they wanted, and peaked in the open window. Inside was an older guy, about 40, clean cut, muscular, dressed in jeans and a tight fitting t-shirt. He was friendly, and explained that he thought he recognized me, but was mistaken.

"As long as I'm stopped, though, can I offer you a lift?"

I was not at all looking forward to my long walk home, so I said "sure, that would be great!"

I hopped in the car and he drove off.

We started chatting, just small talk about how nice a night it was, where we'd been, if there had been many people on the go. Then he asked if I liked to smoke-up, and if I'd like to have a joint with him.

"I can't drink much when I take the car downtown, so I like to have a few draws instead," he explained.

I said "sure, I wouldn't mind a puff." I didn't know many places to score weed in the city, and figured a new connection would be a good thing. "I'm Leon, by the way," I said, introducing myself.

"Hi, I'm Mark," he replied, shaking my hand.

I thought he'd pull into a parking lot and light one up, but he started driving out of the city, explaining that he lived just outside of town, and had to go there because he didn't have any grass left on him. I was young, I liked to party, it was still kind of early, so I said what the hell, why not?

We drove for about 15 minutes, and finally pulled into a secluded driveway in front of a nice big house. I finally asked about how I would get home after, and he answered "don't worry about it, I'll give you a ride when we're done."

We went into the house and down to his rec room. It was a beautiful place. He had a full bar set up, a hot tub on the deck just outside the rec room, a nice stereo and a big-screen tv.

He told me to go ahead and make myself comfortable. He offered me a drink, which I accepted, and he sat down next to me and pulled out a joint. We passed it back and forth, and it hit me hard right away. It was way more powerful than what I was used to, and my head started spinning.

He noticed the effect it was having on me and said "don't worry, that'll pass quickly. This is some good stuff, it'll really mellow you out. Here, let me freshen up your drink," and he topped up my glass.

We sat back and chatted for a while, our thighs touching, and as his hand was on his thigh, he was lightly touching mine as he moved his hands.

The weed was really strong, and again, in hindsight, I know now that it was laced with something, but at the time I knew nothing about those kinds of things, so I thought it was just plain old good grass.

He lit up another one, and we passed it back and forth a couple of times, then he said, "hey, let's try a brainer." He put the joint in his mouth backwards, and leaned in towards me, blowing smoke out the joint, which I inhaled. That really knocked me for a loop, and combined with all I'd drank that evening, I was now really out of it.

He continued to sit really close to me, and started rubbing my thigh as we talked. I thought it was a bit weird, but I was so stoned I didn't really know how to deal with it. Plus it felt so nice. Everything felt so nice, I was just completely at ease and having a good time.

He asked if I wanted to try the hot tub, and again, I was along for the ride. "Sure, if you want to," I said.

He went and grabbed a couple of towels, and we went out on the deck. He had a very private back yard, and we could only see some faint lights from a neighbours window a long ways off.

"No sense being shy," he said, stripping off and climbing into the tub.

He was a good 6" taller than me, at about 6'4", and in great shape. He was moderately hairy, just enough to make him look really masculine. And his large cock was partly erect, hanging down 6-7".

I was stoned, but still a little nervous. I took my clothes off, and just before getting in the tub he asked me to go back inside and grab us a couple more drinks and another joint, which I did, walking away butt naked.

When I came back the tub was on a low setting and I settled in across from him, but he came over to my side while we smoked the joint. I tried to decline, as I was feeling really out of it, but he said "come on, you only live once! Here's to new friends!"

He had his arm on the edge of the tub behind me, and again leaned his face in close to give me another brainer. When we finished the joint his arm came off the edge so that it was on my shoulders, and he held me close to him as we chatted. Our hips were touching, and he moved his leg so that it rubbed against mine.

"This weed is so awesome," he said, "it makes everything feel so good." I knew what he meant. His skin rubbing on mine felt so wonderful. I put my hand on his thigh under the water, and gently caressed it.

As we talked our faces got closer and closer, and I could feel his breath on my neck and ear. I'd never dreamed of doing that with a man before, but the tingles and pleasure it gave me were undeniable. He squeezed me tighter into him with his arm that was around me, and my arm went around his lower back. With his opposite arm he started to rub my thigh, and I began to caress his chest.

Just as I was starting to wonder where this was going to lead, he got up and told me to follow him. Without question, I did. We dried off a little, and then left the towels and our clothes there, and went back into the rec room.

He turned on the tv and put a movie in the VCR. The title came up, and it was called "Twinks on Bears", which again, meant nothing to me. It didn't take long for me to figure out it was a kind of movie I was very unfamiliar with. But, stoned as I was, I sat there, taking it all in, and he passed me another drink and lit up another joint.

Again, we sat next to each other on the couch, our legs touching, and he started to gently rub my chest and thigh. I glanced away from the tv long enough to see his cock had risen to full mast. Mine had too, I must admit. I'd never been with a guy before, but here I was, naked, in a stranger's house, his hands caressing the back of my neck and rubbing my thigh, and I was horny as all hell. He was telling me what a nice tight body I had, and how good I felt in his hands. He took my hand and placed it on his rock hard cock, and I think it was only then that I really clued into what I was about to do. And even though I'd never dreamed of being in this situation, everything felt so right, I knew I was just going to go along with whatever he wanted to do.

I gently caressed his cock, marvelling at the size and feel of it. It was the first time I'd ever touched another man's cock, and of course it was completely different from touching my own.

With his hand on the back of my neck he began to guide my head downwards. He turned my head so that my face was on his chest, and I instinctively began to lightly kiss and nuzzle his skin through his chest hairs.

When I got to his cock I did much the same, and he guided me through the whole process. I kissed my way down to the base of his cock and then he told me to use my tongue, which I did. I licked and licked, savouring my first taste of cock. It felt so soft, hard, and smooth all at the same time.

When I got back up to the tip I took it in my mouth. Deeper and deeper until it was bouncing on the back of my throat. By this point I had moved so that I was kneeling in front of him, and he moved out to the edge of the couch so that his cock was pointing straight out and with my head tilted back he had a straight shot at my throat. Holding my head in both his hands he started to rock me back and forth, his cock banging on the back of my throat each time, making me gag and drool.

At this point I had had enough, and wanted to stop, but he was determined to get his cock down my throat. "Come on, swallow that cock! Oh yeah, that's it, that's it," and he continued to hammer his cock into me until I managed to get my throat open enough. Then he hauled my head closer and closer until my nose was buried in his pubes.

My air was completely cut off, and I thought I would suffocate, but he pushed me back off just enough so that his cock was out of my throat but still in my mouth. I gasped for air as he plunged his cock deep into me again. Over and over, he would plunge his cock in my throat, pump two or three times, pull back enough to allow me a quick breath and then plug my throat with his enormous cock again.

After 5 or 6 minutes of this I could feel his cock swelling. He pushed it even deeper as he let out a loud moan and I felt his cock pulse, shooting cum down my throat. Before he was finished cumming he pulled back and shot cum into my open mouth. "Taste that cum! Swallow it down!" he told me, and then, holding on to me by my hair, had me lick and suck his cock clean. He let me go, and I slumped down on the floor, totally exhausted, and unsure what to make of what had just happened.

"Well that was fucking awesome! You're quite the cock sucker. Why don't you get us a drink and pass me another joint?" he said, in what sounded much more like a command than a request.

I got up and poured a couple more drinks and got another of the joints he had left on the bar and came over to sit by him, but instead of letting me sit on the couch he guided me back to the floor in between his legs, telling me "it's so hot looking at you down there, ready to serve."

I took a few big drinks from my glass, trying to relax my throat and jaw. He put his feet up on the edge of the couch, took hold of my hair and gently pulled my face into his crotch, so that my mouth was on his balls. He laid back, smoking his joint while telling me to lick his nutsack.

"Look at me", he said, and I peered up over his cock to look him in the eyes as I gently lapped at his balls. "That's right, keep licking those balls. That feels fucking awesome." But though he said he wanted me to lick his balls, he lifted them up, spread his legs further and pushed me down so that I was licking his taint. "Fuck yeah. I'm glad I picked you up tonight. You're an eager little slut aren't you?"

He then pushed me down further, and when I appeared I would stop licking, he hauled my head into his ass and told me "lick it! Eat my ass until I get hard again!"

I'd eaten my girlfriend's ass once or twice in high school, but I'd never dreamed I'd be doing it to a man roughly twice my age.

As he held me by the hair with one hand, he began to play with his dick with the other, and it slowly started to get hard again. As it grew and grew, I had to marvel at the beauty and size. It was a magnificent tool, no doubt.

His dick hard again, Mark had me come up on the couch again, and me kneel up on it, leaning on the back of the couch. He got something out of a drawer in the coffee table, and started caressing my ass. "Just relax", he said, "you're going to love this."

He put some lube on my asshole and gently inserted a finger. It felt kind of funny to me, but not unpleasant. Next, he put in a small, well lubed dildo, working it gently, and soon I was moaning softly, enjoying the new experience and sensation.

"Alright, time for the main event," Mark said, pulling the dildo out and stepping directly behind me. I wasn't at all sure I wanted to be fucked in the ass, but I had such a buzz-on that I was just going to go along with whatever was suggested.

Mark gently rubbed his cock up and down between my ass cheeks, and I squirmed with pleasure. He pulled me back a bit to get the angle right, and slowly and gently began to insert his giant tool into my ass. It was much larger than the dildo, so it hurt, a lot. But Mark took his time, and allowed me to adjust. He would pull back a little, and then push in a little further each time. After about 10 minutes, he had his cock buried in me, and I was experiencing a completely new mix of pain and pleasure. Had someone asked, I honestly wouldn't have been able to decide if I liked it or not, but as I didn't want it to stop, I guess I'd have to say that I did. Mark slowly began to pump in and out of my ass, slowly picking up his pace.

"Uh, uh, uh, uh," I was grunting with every pump, and slowing losing myself in the painful pleasure of getting fucking in the ass. Mark turned me on the couch, pushing my face and chest on the cushions, with my ass still in the air. And still he fucked my ass. Faster and harder, it wasn't long before I was being properly fucked and the sound of him slapping against my ass became louder than my grunts and moans.

After a few minutes he got me to turn over on my back. My dick, which had been rock hard in the hot tub and while I was blowing him, had shrunken almost out of sight. Mark said, "ahh, look at this poor little thing, and caressed it a little. But before it began to grow, he said "I've got something else for you to try," and took something else out of the drawer. I didn't even see what it was until I looked down and saw my cock locked in a cock cage.

"What the hell is that?" I asked.

"This, my friend, is a cock cage. It'll keep you from getting a full erection, and keep you from cumming too fast. Don't worry, it's just a fun toy."

Satisfied, I lay there and spread and lifted my legs as he once again moved into position to fuck my ass.

With his cock pushing gently against my hole, he said "tell me what you want."

"What? What do you mean?"

"Tell me what you want. Do you want my cock? Beg for it."

"Yes, I want your cock," I said.

"Not good enough. Tell me what you want."

"I want you to fuck me. I want your cock in my ass."

"Beg for it!"

"Please fuck me. I need your cock. Fuck me, please..."

As I carried on asking for his cock, he slowly put it in, and started fucking me. He pounded my ass, moving me around to several different positions, fucking me for 10 or 15 minutes straight, until finally he pulled out and moved me to a kneeling position in front of him and told me to open my mouth. I didn't like the idea of sucking a cock that had just been in my ass, but thankfully he just jacked off and sprayed his cum in my mouth and on my face, after which he collapsed back on the couch.

"Fuck, that was hot. You're a hot little piece of ass," he told me. I knelt there, cum on my face, my cock throbbing in it's cage, not sure what was going to happen next.

"Well, I need to grab some sleep, and I'm sure you could use some too," he said.

"What about my ride home?"

"Listen, I've had too much to drink and smoke to be able to drive. But you can sleep here, I don't mind."

He got me a blanket and told me I could have the couch, and he went off to bed. I was trying to process everything that had happened, having trouble believing that I'd given him a blow job and been fucked, but still hadn't cum myself. And now I was going to sleep on his couch with cum on my face and my cock still in a cage.

In the morning I was awoken by Mark, rubbing his cock over my face.

"Good morning sunshine, time for a morning treat!"

Thankfully, I thought to myself, Mark had showered, as he pushed his cock past my lips and into my mouth. My buzz was completely gone, so all of my inhibitions had returned, but Mark didn't give me time to think, or much choice in the matter. He pushed his cock into my mouth, maneuvered me into a position where I was on my back and my head was hanging off the couch, and within a minute he was pumping his cock deep down my throat. He came in a matter of minutes, yelling "fuck ya, gotta love moring head!" He pulled out, straddled my face so he could rub his ass on my face for a few seconds, and then stood up, telling me that I should grab a shower before breakfast.

I was now very embarrassed. I'd never had a homosexual experience in my life, and with no buzz on, I was feeling very awkward and out of place looking at this man, twice my age, standing naked before me. But, I couldn't deny that my cock was throbbing in the cock cage, struggling and failing to become erect.

I agreed that I'd like to take a shower, and asked about getting the cock cage removed. Mark told me not to worry about that right now, that I should get cleaned up, and breakfast would be ready soon. He led me to the bathroom, showed me how to work the shower, where I could find a towel, and what soap and shampoo to use. Then he gave me another can with no label, and said I should use it on my whole body after the soap, and that it would make my skin super soft.

Well, it turns out the foam in the can was a hair remover! I ended up removing all the hair below my head! Under my arms, pubic area, legs, everything. What the fuck, I thought, it must be a practical joke.

I went to the kitchen, wrapped in a towel and red-faced, both angry and embarrassed. Mark, though, was jovial, and invited me to sit down. He had made omelettes, toast and coffee, and he sat down opposite me and we started to eat.

Breakfast looked really good, but I was too hungover to enjoy it. I asked again about getting the cage off, but Mark was evasive, asking if I had a good time last night. I had to admit that, though it was all a bit of a blur, I thought I did have a good time.

"Well", he said, "I'll make you a deal. I had a fantastic time last night, and I'd like to have a better one tonight. So, I want you to come back this evening. I'll cook you dinner, we'll have some wine, we'll have some drinks, we'll smoke a few joints, and maybe a few other treats, and have a good time. What do you think? It'll be wild!"

I was tempted, but said, "that sounds like a good time, but what about this cage? Can you take it off?"

"Of course I can. But I think it'll be more fun if we wait. You come back for dinner and drinks tonight. If you're easy to get along with, like you were last night, I'll remove the cage. If you don't want to cooperate, you can go down to the local garage and ask them to cut it off for you. What do you think?"

I was pissed off that he'd try to blackmail me, but I certainly didn't like the idea of going to a garage and dropping my pants so a mechanic could remove a cock cage. Plus, as a starving student, a night of free drugs and alcohol, plus a nice dinner, was tempting. It was Saturday morning, and I had no plans with my friends for that evening. What was more tempting, a Saturday night of wild adventure, or a Saturday night of university assignments and Hockey Night In Canada?

"Alright", I said, "but it better be a fantastic supper. And I hope it's going to be wild."