The Paperboy Delivers Pt. 01

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Bi-curious paperboy experiments with customer.
8.9k words
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Part 1 of the 3 part series

Updated 04/06/2024
Created 04/04/2024
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This story takes place a long time ago, when people got their news from a printed newspaper delivered to their doorstep each morning by a neighborhood kid, and when not many people had access to video porn. Public sentiment towards gay and lesbian relationships was not favorable making people hesitant to explore same-sex relationships.

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A couple of days into summer vacation after my junior year in high school, my little brother had a serious bicycling accident. As he was riding downhill at full speed, a driver who wasn't paying attention backed out of a driveway right into his path. My brother hit the side of his car, flew over his handlebars, bounced off the roof of the car and landed on the curb on the other side. His injuries include a fractured cervical spine that left him partially paralyzed. Back then, neurosurgery and physical therapy were much less advanced than they are today, but the doctors were able to relieve the pressure on his spinal cord. They were hopeful he'd regain full function, but they said he'd probably have to relearn how to do everything. They expected his recovery to take up to a year.

Kit was always ambitious and had signed up for a paper route as soon as he was old enough. He'd been delivering the morning paper for a year and was proud of earning a steady paycheck at only thirteen years old. My parents wanted to be sure he had that paper route to look forward to when he recovered, so they talked me into taking it over. And that's how, a couple of months after my eighteenth birthday, I found myself getting up at five a.m. on my summer vacation to do a job that junior high school kids usually did.

After a few days I came to like the peace and quiet of the early morning as I made my rounds. I could usually get another hour or so of sleep before I had to be at my regular summer job, working at the front counter of the municipal swimming pool.

What I didn't like was Thursday evenings when I had to go collect payment for the papers from my customers. Ring the doorbell, hope someone answers, remind them how much they owe, wait for them to go get their wallet or purse, make change, record the payment, move on to the next house. Repeat for about a hundred customers. By the end of the summer, I could get it done in a little over two hours on a good night.

However, on my first day making collections, as I approached the final customer, I was thinking about how sore my legs were from three hours of walking and dreading the thought of the mile and a half walk home. I rang the doorbell, and when it opened the man behind the door looked puzzled, just like everyone else that night.

I said, "Hi, I'm Ian, Kit's brother," and I explained about his accident. The guy said he was sorry to hear about the accident, said he and his wife liked Kit, and said that they'd keep him in their thoughts and prayers. He said I looked a little old to be a paperboy and I admitted I was a senior in high school and had recently turned eighteen. As we talked, I was absentmindedly rubbing my back. He noticed and said, "You look tired and it's hot out here. Why don't you come in and have a beer while we finish talking."

The drinking age in our state was still eighteen back then, so I was legal to drink but hadn't had many opportunities other than the occasional beer my father let me have. Being a typical eighteen-year-old boy, I wasn't going to turn down a beer, so I said, "Sure," and he led me to his living room which was off a small entry hall.

As he walked down a short hallway, I sat down and glanced at the TV which was on, tuned to a sitcom that my parents liked to watch.

The man returned a minute later with two cans of beer. He handed me a can and sat down on the sofa as he said, "By the way, I'm Roy," before we picked up our conversation about Kit again.

As we talked and drank our beers it seemed to me that he was looking me up and down in a way that made me a little uncomfortable. He must have sensed this because he said, "Excuse me if I'm staring at you. I'm not one of those guys who ogles the neighborhood kids. I'm just a little envious of what good shape you're in. I've been working out trying to put on some muscle, but as you can see, my results aren't as good as yours."

I laughed and said, "My football coach would love to hear you say that. He's a fanatic about weightlifting and he's had the whole team in the weight room four or five days a week since we were playing freshman football." Taking a closer look at him I added, "You look strong, even though you aren't really pumped. I wouldn't be surprised if you were an athlete in school."

Roy told me that he wanted to play football in high school, but he'd been too small. He looked to be about five foot ten, but he said he hadn't gotten his growth spurt until the end of his senior year. Before that, he stood five foot four and competed in gymnastics. He'd hoped to continue in college, but once his weight started going up, he couldn't get strong enough to compete.

I said he still looked fit, and we started talking about our workout routines. That led to both of us taking off our shirts to compare where we were having success and where we were having problems. And I think we both wanted to show off a little.

Just then Roy's wife came through the front door. As she turned into the living room and saw us she stopped in her tracks. Roy made the introductions and told Lisa we were comparing notes on our weightlifting routines. Lisa made an exaggerated leering face and said, "I'd be glad to help with any comparisons you need."

We put our shirts back on and Lisa joined us as we finished our beers. That day we talked about how long they'd been in the neighborhood, where they came from, and what they did for a living, and I told them a little about my family and my college plans.

The next couple of weeks were similar with Roy and I having beers together and talking each time I came to collect. Roy worked as an engineer, which is what I wanted to study in college, so a lot of our conversations centered around college choices, different engineering majors and careers in engineering.

Then came the week when I knocked, and Roy answered the door in a light bathrobe that fell just to the middle of his thighs. He said, "Oh, it's later than I thought," as he let me in. When I walked into the living room, he didn't invite me to sit or offer me a beer as he had the past two weeks, and he looked distracted as walked out saying he was going to get my money.

I looked around the room as I was waiting for him and as I glanced at the TV, I was shocked to see an image of a naked woman bent over a desk with a guy in a business suit behind her lining his cock up with her pussy. The woman was a knockout with a tight ass and perfect cone shaped tits hanging down, and the guy's cock put mine to shame. I'd never seen a porn video before, or even live sex, so my dick was instantly tenting my shorts.

Roy walked back in and seeing where I was looking, he said, "Oh, crap. I thought I'd turned that off."

With all the blood having gone to my dick, my brain wasn't fully functioning, so all I could think of the say was, "You've got a home video player!" VHS and Betamax players were fairly new back then and they were expensive, which made them rare. Porn tapes were even more rare, and they were generally of greater interest to teenage boys. To this day I don't know why that wasn't the first thing I commented on.

After a few moments of silence I did say, "Wow! A sex video! I've never seen one before. That looks really hot!"

I think Roy was embarrassed and wanted to get me out the door as quickly as possible, but he wasn't thinking any more clearly than I was. He muttered something like, "Here's your money, have a good night," but then he added, "Uh, you can have a beer with me and watch a little if you want to."

I said, "Oh! Uh, sure. Yeah!" and Roy left the room again to get some beers. I used that opportunity to adjust my cock, trying to make it less conspicuous as I sat down on the sofa.

When Roy came back, he sat in an armchair next to the sofa. The way he was positioned, he was almost facing me and had to turn his head to see the TV. He explained unnecessarily that the guy was the girl's boss and she'd just agreed to have sex with him to earn a raise. Then he hit play.

As we watched, my cock got harder and harder, and I could feel precum soaking through my underwear. I was glad I'd worn a long T-shirt because I knew there was going to be a visible wet spot in my faded denim shorts.

I could see Roy sneaking glances at me as I was sneaking glances at him. His cock was getting hard too, and he was struggling to keep it under wraps beneath the thin material of his bathrobe. His dick kept making an obvious tent, and he was trying to make it less obvious without actually grabbing it. He flashed me a couple of times when he made a wrong move adjusting his robe, giving me my first ever view of another guy's fully erect dick. I also realized his robe was so short that his balls were always hanging in sight unless he squeezed legs together.

I was torn between sipping my beer slowly so I could see more of the video and slamming it down so I could go home and do something about the painful hardon in my pants. By the time the boss pulled out of the woman's pussy and sprayed his cum all over her back, I was sure one or two tugs on my cock would set me off. I stayed through one more scene where two other women gave the boss a blowjob and he coated their faces with an impressive amount of cum.

After that, I left quickly and speed-walked home. When I got there, I was sweaty, and my cock had only softened a little. I was breathing hard and blood was pounding in my ears as much from the memory of that video as from the exertion of racing home.

Everyone in my family was busy with something as I arrived home, so I was able to walk in unnoticed and make my way to the bathroom. Once there, I quickly stripped, jumped in the shower, and grabbed my dick. Almost as soon as I touched myself, I was painting the walls with cum.

I washed myself and soaked for a bit, thinking my pounding pulse would finally slow down. Instead, I continued to recall images of the woman getting fucked, of the boss getting a blowjob, and of Roy's hard cock. When I realized thoughts of Roy's cock were getting me hard, I chalked it up to the novelty of seeing another guy with a hardon for the first time. I decided to embrace my dirty thoughts, and pretty soon I was painting the walls again, imagining I was cumming on those two pretty faces.

The next week, Roy met me at the door wearing a pair of shorts and a T-shirt. He was calm and spoke in a soothing voice as he said, "We should probably talk about last week."

Roy handed me my money as we walked into the living room and invited me to sit on the sofa. He'd obviously been planning for us to talk, because were two cold beers on the coffee table. He cracked open one of the beers and handed it to me as I sat down at one end of the sofa. Roy sat down at the opposite end, opened the other beer, and immediately took a big drink.

Roy started by saying, "Lisa and I have a pretty active sex life. It's rare for us to go more than a day or two without making love. She's been covering the late shift for another nurse who's on maternity leave, so I've been in bed when she gets home. Obviously, she's sound asleep when I get up for work, and she's gone by the time I get home. When you came by last Thursday, we hadn't had sex since Saturday, and I needed some relief. Lisa actually left that video out where I'd see it with a note telling me to imagine she was the girl in the video. That's why you found me like that."

He went on, "I hope you don't feel uncomfortable around me after last week. Once we started watching the video, I started feeling weird sitting there with my junk hanging out and my dick getting hard where you could see it. That must have been weird for you too."

I admitted that it was strange, but also told him I was a little curious because I'd never seen another guy's hard dick.

Roy gave a sigh of relief and said, "That's great to hear. I don't want you to think I'm some pervert who likes to flash teenage boys."

"I also felt bad about sending you home with blue balls. I normally jerk off a couple of times when I watch those videos. I know I needed to work one out when you left, and I'm sure you were feeling the same way. It was hard to miss your hard cock, the way it was stretching the front of your shorts."

I told him about my walk home and my long shower, which led him to ask me, "So you don't have any place private at home where you can do that?

I told him I share a bedroom with Kit, and now that he's home from the hospital he's in there almost all the time.

Roy said, "I know you enjoyed the video, and I'm guessing you'd like to see some more. If you'd like, I'd be happy to let you use our spare bedroom or the bathroom to relieve yourself. Or, if you're not too shy and you want to stroke yourself while you watch, I can give you a blanket to put over your lap. I won't even be offended if you pull it out in front of me. I walked in on my college roommate many times while he was jacking off, so you wouldn't be the first guy I've seen stroking it."

There was never a question in my mind that I was going to accept his offer to watch porn videos with him, so I asked the one question that was on my mind, "What will you do?"

Roy said, "I like to stroke myself as I watch if that won't make you uncomfortable. I can do it under a blanket if seeing me masturbate will make you uncomfortable. I'd rather not wait until you leave. I like it better if I can edge myself."

That was a term I'd never heard, so I asked, "What do you mean when you say you edge yourself?"

"Edging is bringing yourself to the point where you're just about to cum and then stopping to cool off. It's a way to prolong that sexy feeling in your cock. It also makes my orgasm a lot stronger when I finally let myself go."

That sounded exciting to me. While I was hesitant about masturbating in front of another guy, I was also eager to learn how to make jacking off more fun. I asked Roy, "This may sound weird, but could you teach me how to do that?"

That seemed to catch Roy off guard. He gave me a long, considering look before he said, "I probably could, but that means we'd have to watch each other. I'd need to show you how to keep yourself stimulated without making yourself cum, and I'd have to watch you to help you learn what to do when you're close to cumming."

The images of Roy trying to hide his cock the week before flashed through my mind, sending an involuntary tingle through my cock. I told myself again, "I'm not some gay guy that's turned on by cocks. It's just curiosity," and I said to Roy, "I'm okay with that."

Roy said, "One other thing. I'm sure you saw that I wasn't wearing anything under my robe last week. That's because I like to strip down when I jerk off. I like the feeling of being naked, and I like watching my own cum shots. I imagine I'm the guy spraying cum on some porn star's ass. If that makes you uncomfortable, I can keep my clothes on and use a tissue."

Before Kit's accident, I'd wait until I was the only one home and then I'd strip down in my room and jack off. Sometimes I'd even walk around the house naked. I liked the feeling of freedom I got walking around with no clothes on, and I'd imagine what it would be like if my family was a bunch of nudists, walking around the house naked all the time. I'd heard about nudist colonies and wondered what it would be like to be around naked people all the time.

One time my little sister walked in on me. Luckily, she didn't catch me with a full boner, or worse yet, jerking off. All I could think to do was run to the bathroom and take a shower. When I got out, I told her I heard a noise from outside like a car accident while I was getting ready for my shower. She told Mom and Mom told me I should have grabbed a towel or my robe. That was just a few days before Kit's accident. Rather than explain all that to Roy, I just said, "I like being naked when I jack off too. Let's do that."

Roy excused himself and left the room for a minute, returning with two large beach towels. He draped the towels over the sofa, near the middle but not touching, clearly indicating that he wanted us to sit there while we masturbated. The closeness of the towels made me a little uncomfortable, but then I realized it would make it easier for us to watch each other without turning away from the TV.

I kicked off my shoes, then hesitated. We stood facing each other for what seemed like a long time, neither one of us wanting to be the first one to undress. Roy finally took a deep breath and pulled his T-shirt off, dropping it on one of the armchairs, watching my face the whole time. He put his hands on the waistband of his shorts but hesitated to pull them down. I realized he was waiting for me to take my shirt off, so I quickly pulled it off and threw it on top of his.

I could see that Roy was wearing a pair of running shorts, the kind that are designed to be worn by themselves without underwear or a jockstrap, so when he pulled them down, he was standing in front of me completely naked. His dick was half hard as it came into view. By the time he picked up his shorts and threw them on the chair with his shirt, his cock was fully erect and bobbing with his heartbeat.

It took me a little longer to unbutton my denim shorts. As I dropped them to the floor, I was embarrassed to realize that my dick was fully hard under my tightie whities. I had to grab it with one hand and maneuver it clear of the waistband as I dropped my underwear around my ankles. I pulled my feet clear and bent down to pick up my clothes, conscious of my cock swaying in front of me. I was even more embarrassed when a drop of precum fell from the tip and landed on the floor, especially when I saw Roy looking at the wet spot on the hardwood.

Roy sat on one of the towels, putting his feet up on the coffee table and spreading his legs. He patted the other towel as an invitation for me to sit while he grabbed his balls and arranged them so they could move freely.

I sat and tried to arrange myself similar to the way Roy was sitting, but when I spread my legs, my knee was pressed against Roy's. I quickly pulled my legs back together, drawing a chuckle from Roy. As if he was reading my mind he said, "Touching knees doesn't make us gay."

That brought an embarrassed grin to my face, and I felt a lot of tension leave my body. I quickly got myself arranged comfortably, and without thinking gripped my cock loosely as I told Roy, "Okay. I'm ready."

Just the light touch of my hand caused my cock to release another drop of precum. Laying back on the sofa as I was, it landed on my stomach and ran into my belly button. I snuck a glance at Roy to see if he'd noticed and saw that there was a steady stream of precum dripping from his piss hole.

Just then Roy started the video. He told me, "This video isn't one story. There are four different scenarios, each with two guys and one girl."

The first scene started, and it showed a young couple who looked about my age making out on a big leather sofa. Within a couple of minutes, the girl's tits were out, and the guy had his hand under her skirt playing with her pussy while she pulled his impressively large cock out of his pants and jerked him off. It was hot seeing her tits and pussy, but I wasn't so excited that I felt like cumming.

Then, as the girl starts giving the guy a blowjob, his brother walks in. Brother two threatens to tell their parents about brother one having sex in their house unless the girlfriend takes care of him too. As Brother Two pulls out a cock that's even bigger than the Brother One's, the girlfriend's eyes light up and she immediately agrees. The rest of the scene shows the girlfriend stroking, sucking and fucking both brothers' cocks until one cums on her face and the other blasts his load on her tits.