First Time For Everything

Nis 15, 2024 // By:analsex // No Comment

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The early 1970’s when a boy became a man…


“What do you think, Timmy?” my new friend asked as he walked me over to his car, which he seemed to very proud of judging by the way he smiled as he looked at his pride and joy.

“Nice,” I felt obligated to respond, although I didn’t know all that much about cars.

The Mustangs and Corvettes caught my eye but I didn’t know much about cars like this Chevrolet Corvair. Chester did though and he proceeded to rattle off a whole lot of facts about this 1962 car which had a aqua paint job.

The car was very clean and without a dent or even a scratch which for being 10 years old was probably quite an achievement. That was part of the reason that when Chester offered to give me a ride I explained that I couldn’t because my swimming trunks were still wet.

“I’ll put a towel down for you. That way you won’t stick to the seat too,” he declared, and after he grabbed one from the back seat and set it down he added, “Now you have no excuse not to go with me. Come on. It’ll be fun.”

Actually I did have an excuse. I was scared because of the way the man had been looking at be all afternoon in the pool, and after I got into the car he happened to hit on something else.

“Didn’t your Mom ever tell you not to get in cars with strangers?” he said with a grin after he got behind the wheel and clamped his hand on my bare thigh, but when he saw what was probably a shocked look on my face he assured me I had nothing to worry about.

“Wouldn’t hurt a fly,” Chester assured me and with that my journey began.

The ride lasted for about 10 minutes, and as he drove I looked over at my new friend and wondered how I had gotten into this situation. The obvious reason was that I had developed a bad habit, which was an inability to say no, especially to people who either had authority or acted like they did as Chester had.

I guess I had asked for it by staring at the middle-aged man quite a bit, and when we ended up near each other in the pool he asked me that he noticed I had been checking him out a lot.

“See something you like?” he asked, and in panic I came up with the best answer I could.

“Uh – your necklace. It’s cool,” I mumbled, pointing at the gold peace symbol than hung around his neck but even when he nodded I suspected he wasn’t buying it.

The only reason I had noticed it was that it stood in stark contrast to the mat of black hair which covered not only his chest but went down from his collarbone right down to his trunks. Recently I had found myself attracted to men like this for some reason, but apparently I had been too obviously observant when it came to this man.

Now I was in the man’s car and he was parking in this little lot that was hidden way in the back of some park outside of town. I didn’t know where I was but this man did and now he was swiveling in his seat and offering me something.

“I know you hippie kids dig this stuff,” Chester said as he handed me a joint, and while I wasn’t a hippie even if my hair was getting a little long I knew what this was. “I can see why you cats dig it. Here, take a deep drag.”

The only thing I had ever smoked before was a cigarette I had shared with my friend Gary a couple of years ago, and that one experience had made me dizzy. This wasn’t much different but I was intimidated by Chester so I did what he said.

“What grade are you going to be in come fall?” Chester asked after handing me the joint back, his hand landing on my thigh after the exchange.

“Freshman,” I told him, and I was just about to tell him about the college in Colorado I was going to be headed to when his hand slid up to my crotch.

“Relax Timmy,” Chester said as my heart raced and my head spun. “Just lean back for me.”

I sat there and did what he told me to. His hand went up to my chest and massaged my little man boobs, pinching my nipples lightly before letting his hand glide down my slightly soft stomach and work under the elastic waistband of my baggy swim trunks.

Only one hand had gone where Chester’s was right then, and she had giggled when she found what she was looking for. Chester didn’t laugh but he did smile and his hand didn’t stop even though I grabbed his wrist and asked him not to do this.

“It’s okay,” he said with an even bigger smile as his hand worked lower. “Hmmm… you’ve got a little hair down there, don’t you? Sweet.”

“Please don’t mister,” I asked politely, but he didn’t stop although he reminded me his name was Chester.

“You don’t want me to stop, do you?” Chester asked, and even though I nodded I wasn’t sure because he was squeezing my dick and making it even stiffer than it had been. “Your dick is so hard. Let me take care of that for you.”

Chester looked around to make sure we were alone in the parking lot before tugging my trunks down to my knees, and while I would tell myself later that he was the one that did it there was no way it could have been done without my letting him and even lifting edirne escort my butt up a bit when asked.

Chester took the joint from me and took one last drag before pitching it out the window and leaning over me. A couple of seconds later he was doing something that I had only heard about, except it wasn’t a blowjob like they said it was. There was sucking involved and it felt incredible for as long as it lasted.

Just like I did when I used my fingers, it didn’t take long for me to cum but it felt so good that after I came with my hand digging into the armrest, it was only then that I realized that Chester had my dick in his mouth when I came.

“I’m sorry,” I said when his face came out of my lap, but he wasn’t mad even though my semen was trickling out of the corner of his mouth, a situation he corrected with a flick of his tongue.

“I’m not,” Chester said with a smile. “Your little cannon sure fires a lot of ammo though. You must have had that load saved up for a while, huh Timmy?’

“I guess,” I said with a shrug of my shoulders, although I had jerked off that morning in the shower like I did almost every day.

“How about you and me go to my place?” He suggested, and before I could say no he was starting the car up and backing out of the lot. “We can get comfortable and have some more fun. I’ve got beer, and I bet you like beer.”

Beer I had tasted before so Chester was right about that.

“Pull up your trunks, Timmy,” Chester said as he began driving. “If I get stopped by a cop that would be tough to explain, although I do like the view.”

“I don’t know about this,” I said after tugging up my trunks, trying to figure out a way to avoid going where he was taking me.

“What time your folks want you home?” Chester asked.

“It’s just Mom. My Dad – he’s…”

“Mine died young too,” Chester said. “Well, don’t worry. After we have some more fun I’ll make sure you get home safe and sound. Okay?”

“I guess so,” I said as he drove into what seemed like a small apartment complex.

“I’m just curious Timmy,” Chester said as he looked around like he was making sure nobody was watching before we got out of the car. “How old are you?”


“Oh yeah?” Chester said as he gave me a look that made it seem like he thought I was lying. “Well, that works for me. Let’s get inside quick.”

We skipped up the stairs to the second level and after Chester fumbled with the key for a second we were inside his apartment. It wasn’t very fancy and was cluttered like my bedroom was. It was a studio apartment with an unmade bed in the corner.

“Home sweet home,” Chester said as he went to the refrigerator and pulled out a couple of Carling Black Label’s in stubby bottles, and then he told me to get comfortable and make myself at home before going to the only other room which had to be the bathroom.

Chester was back in a moment, having shed the t-shirt and casual pants he had put on after swimming and now he was dressed like he was in the pool.

“Figure you would have the trunks off my now,” Chester said as he led me over to sit down, not at the little kitchen table but on the bed. “Permit me.”

Chester pulled my trunks down, pausing only to kiss the head of my dick as I stepped out of them, and there I was naked.

“Want me to leave this on, don’t you?” Chester said as he toyed with his necklace before letting it drop back onto his chest. “I’m all yours Timmy.”

“You are a shy one,” Chester finally said after I stood there staring at him for about a minute. “No need to be. Anything you want to do to me, you can.”

I didn’t have a clue what he wanted me to do, so after some more of us looking at each other he took my hands and put them on him while telling me he sensed I liked his hairy chest.

“Not a bad body for a 49 year old guy, huh Timmy?” Chester asked, and while he was no Charles Atlas he was in good shape.

The second my hands went into the pelt of hair that covered his chest I got less nervous. My fingers almost disappeared into the soft forest and as I began to rake my fingers through the jungle Chester sighed and told me he could tell that I was attracted to it.

“You like hairy guys, don’t you Timmy?” he asked, and although I hadn’t realized it I guessed he was right.

“Wish I had hair on my chest,” I admitted as my palms ran across his nipples which were hidden from view.

“You will someday,” Chester sighed as he raised his arms and put his hands behind his neck. “I like you just the way you are now though. Your hands feel nice. Don’t be shy babe. Do whatever you want.”

I was doing just that while just running my hands through his chest hair, but when he raised his arms my eyes darted over to his armpits and the thick tufts of hair that filled his muscled hollows.

I couldn’t help noticing that Chester’s armpits were almost as hairy as Tom’s were. Tom was a guy at school that I always had a crush on and I lost track at how many gymnastic matches I had gone to back at school just to look at his hairy body.

I was gay. Incredibly that came as a revelation to me while playing with this virtual stranger’s nipples. I had tried to be like everybody else while growing up, even going on dates like everybody else, but only because I felt I had to. It was other guys that excited me, and that moment was the first time I was finally come to grips with this.

Chester was watching me as this revelation took place, and while he was amused at my daydreaming while staring at his armpit he didn’t mind and simply took one hand from behind his head and brought my face down to his nipple.

“Suck on it,” Chester instructed as my mouth tried to find the plump bud. “That a boy. Suck on it and make it hard.”

I did as I was told, eagerly sucking on his fat nipple as the soft chest hair caressed my cheek, and then Chester pulled my head over to his other nipple and kept encouraging me.

“You can do more than look Timmy,” Chester said after I gnawed on his nipple a while, and I guess he had caught me staring at his armpit again because now the hand that had been rubbing my neck was now guiding my face upward to that very furry hollow that he thought I was attracted to.

I recoiled a bit when Chester eased my face under his arm and I was going to tell him I didn’t want to do this but I didn’t get the chance because I was already there.

“You know you like it Timmy,” Chester told me. “You dick is hard again already.”

It was true. My boner was poking Chester in the thigh so I let him push my face deeper into his armpit, and after I started kissing the moist and only slightly musky fur his hand came off of my neck.

“Don’t you want to take my trunks off, Timmy?” Chester sighed as he eventually pulled my flushed face out of his underarm and eased me down to my knees.

“I never did this before,” I protested as I found myself at eye level to his tan baggy trunks.

“You’re either the greatest actor in the world or you really are as innocent as you’re acting,” Chester said as he reached down and grabbed my hands to bring them to the waistband. “Either way turns me on. Ease them down, nice and slow.”

I must have been a sight as I pulled down his trunks, my head turned away and my eyes screwed shut while I pulled the trunks down his hairy legs and let him step out of them.

“You can open your eyes,” Chester told me. “It’s not that scary looking.”

It was though. I opened my eyes and saw his cock hanging there in front of my face. It looked like a cigar, brown and wrinkled and veiny, and he wasn’t circumcised which made it even scarier looking.

“Big enough for you, Timmy?” Chester asked as he grabbed the tube by the base, which was hidden in the wild bush of curls above it, and when he wiggled it in my face the foreskin slid back a little to reveal the tip of the head. “I’ll bet you can make it even bigger.”

In retrospect Chester wasn’t all THAT big, although when your nose is almost against the first dick you were being introduced to in this manner your mind gets a little dazed. It was certainly bigger than most of the guys in the locker room though and way bigger than my own even when mine was as hard as it was then.

“I swear I never did this before,” I said as I looked up at Chester in hopes my pleading eyes would do to him what they had done to my Mom back when I used to ask for cookies or money.

The problem was that I wasn’t a kid but an 18 year old who was on his knees in a stranger’s apartment being forced to do something I didn’t want to, or at least that was what I was attempting to convince myself of.

The truth was much different. The truth was that I was about to do something I had wanted to do for a long time. Maybe not with Chester but with other guys, and now I was about to do it. What was holding me back was my ignorance on how to do it.

“Really?” Chester asked me as he looked down at me. “Is it that you don’t want to or you really don’t know how? If you don’t want to you can leave you know. I’ll even take you home. Do you want to leave?”

About twenty long seconds later I shook my head no.

“Wet your lips and open your mouth, Timmy,” Chester instructed. “Watch your teeth and just let your lips slide down.”

With one hand in my scalp and the other holding his flaccid cock Chester put his dick between my lips and guided my face down until my nose was in his pubic hair.

“Not so bad, is it Timmy?” Chester asked, obviously not expecting an answer since about 4 inches of man was in my mouth and his balls were tickling my chin.

It wasn’t bad, not bad for either of us apparently because the jello-like 4 inches almost doubled in length almost immediately, and now Chester was guiding my face up and down his stiff manhood. I was still sucking on about 4 inches, with my eyes trained on the veiny part in front of me.

I tried to go a little farther down but when the tip of his dick would hit my throat I would gag a little so I concentrated on the part I could handle while hoping that Chester wasn’t going to cum in my mouth like I had done to him.

That wasn’t going to happen. Chester’s hands had gone under my arms, his fingers toying with the wisps of hair, but now he was lifting my up. I was afraid I hadn’t done it good as I stared at his bobbing erection that was more than half wet with my saliva, but Chester assured me I had done well.

“You’ll be a professional cocksucker before I get done with you,” Chester assured me as he told me to get on the bed.

“No Timmy, not on your back. Get on all fours with your feet hanging over the end,” Chester said as he went into the night table. “Let me look at that sweet bubble butt.”

“What are you doing?” I asked when I felt his hands on my ass.

“Going to make you happy,” Chester explained. “Make both of us happy.”

“OW!” I cried out when I felt something hard and greasy press against my anus and then push in.

“Stay still and enjoy it,” Chester said. “Doesn’t that feel good?”

To my shock after the initial pain the way he was corkscrewing his long fingers into my ass did feel kinda nice. A lot better than the time I had done it to myself, but even as naïve as I was I had a feeling what was coming.

“Please mister…”

“Chester,” he reminded me as he extricated his finger. “Just relax now.”

I know I cried out when the skinny bony probe was replaced by something thicker, and I remember Chester telling me to be quiet. I know I cried a little as he kept pushing more and more of his cock into my virginal orifice until he had fully impaled me, and all I kept telling myself was that it would be over soon.

Five minutes later Chester had cum, filling my bowels with a warm load which soothed my savaged insides. It was over and how I really felt about it was obvious. I was still on all fours and below me on the sheets were ropes of semen. My semen.

I had cum a minute before Chester, the result of Chester reaching around under me and finding my dick hard, and all it took was a few fast jerks to get me spurting all over.

My protests, my whimpering and my whining were long over by then, replaced by me pushing my ass back into Chester as he pumped his rod into me as hard as he could. After he came I was only sorry that it was over.

“You really were a virgin, weren’t you Timmy?” Chester asked as he leaned over me, his hairy sweaty chest feeling refreshing against my back. “Are you mad at me?”

“No.” I said as Chester climbed off of me and looked at my ass before giving it a playful slap and declaring he better get me home.

It felt like I was ripped wide open back there, and later when I got home I would actually examine myself with mirrors, expecting to see my little pink balloon knot torn and bleeding.

It wasn’t, of course and looked every bit as virginal as it had been before. In fact the only souvenir I had of the occasion were light bruises on my hips where Chester had gripped me hard as he fucked me.

I cleaned up a little bit before putting my trunks on and letting Chester take me home. Before we got to my neighborhood I decided that I didn’t want Chester to know where I lived so I had him drop me off at a friend’s house.

“You want to get together again?” Chester asked and he seemed pleased when I told him that I would.

“You’ll see me at the pool,” Chester told me as he looked toward my friend Gary’s house. “Better not let your Mom see me with you. I’ll see you next week, okay?”

“Sure,” I said and then went up to Gary’s house, going around the back and knocked on Gary’s door.

I made up some nonsense about asking him if he wanted to go to a ball game the next day, which he thankfully did want to do, and then after I figured it was safe I went the couple of blocks to my own house.


A couple of days later I was at home when the phone rang. It was Gary. Turns out somebody had just knocked on his door.

“This big tall guy just came to the door and thought you lived here,” Gary said. “I told him I knew a Timmy that sounded like the way he described you and then he asked me where you lived because he was going to hire you for a part-time job you applied for.”

“Did you tell him?”

“Well yes. I figured he was alright. Neat car he’s got. Was that wrong to tell him?”

“No, it’s okay.”

“What do you need a job for? Gary asked. “You leave for college in a few weeks.”

“Uh – guess I applied for it a while back,” I said while looking out the front window. “Thanks for the call.”

I hung up the phone and was not surprised when I saw the Chevrolet Corvair pull up. I went outside as Chester was getting out, and after he waved he asked me if he liked the Simonize job his pride and joy just got.

“Looks neat.”

“Why did you lie about where you live? It’s a lot nicer than my place.”

“I didn’t say I lived over there. I had to stop at my friend’s house anyway so I had you just let me off there,” I explained.

“Want to go introduce me to your Mom?” Chester said with a smile.

“No. She’s not home. She’s at work,” I explained.

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