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When I Was A Kid
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Straight Male / 39
Paperboy
Back when I was 13-16 I delivered a news paper. It was a decent little job but actually didn’t pay the best. Sunday mornings I had to be over very early to deliver it.
Every su day morning I was out walking my route by 5:30 am. I had about 60 houses I delivered too. I had the regular older people that would be outside drinking their coffee waiting for the paper or the ones that would open their door in just their underwear after I tossed the paper up on their porch. Wasn’t uncommon to see some open the door in their boxes or tighty whities in the morning to get their paper off the porch.
By 7:30 I’d have them all delivered. My one stop on Sunday mornings, it was a guy in his late 50s who would always be sitting out on his porch in just a white shirt and white briefs. I’d occasionally see his morning wood in his briefs some mornings when he stood up to grab the paper from me. He was definitely packing a big one but it never bothered me to see that since I’m a guy and I wore white briefs too. His house was very private as it was back off the road and surrounded by pine trees. So no one could really see him in his briefs.
By this point I had seen him for about 5 months in just his tighty whities on Sunday mornings. He was always very nice and talkative that early in the morning. I’d always be to his house a little after 6:30 am and he told me he woke up at 6:30 am on the weekends. I kinda moved my eyes towards his big morning wood and he smiled and laughed say that explains my morning glory to you, I just woke up.
The following Sunday I was collecting money for my route while delivering the papers. I got to the guys house at my normal time and he was outside as usual. He forgot to grab the money so he walked inside to grab it real fast. I waited in his porch. Now I don’t know how but I was initially invited in while he put the money in an envelope. But ended up sitting on a chair in his living room by his front door, his briefs were under his balls and his dick was in my face. Now when I said he was packing I wasn’t lying. He had a big fat white 9 inch dick. Huge balls and he was very hairy. My hand couldn’t fit all the way around his dick and I could only get he head and just a tad bit of his shaft into my mouth. I was holding his dick with one hand and trying to give his big dick a blowjob.
I must had done it right because minutes later he backed away from me, picked up a towel and jerked off while he coated the with cum. It was a lot of cum. He wiped his dick head off then pulled his briefs back up. We made our way back out to his porch where he sat back down and I left to continue my paper route. He thanked me for the paper and gave me my money plus some extra I later found out. He tipped me 40 dollars.
That continued every Sunday. I started just sucking him while he was sitting out on his porch. I’d just hold his tighty whities under his balls as I sucked him. When he got close to cummimg he’d have me back away and he’d blow his load on the porch floor.
Then after a few months of giving him blowjobs, one Sunday morning when giving him his paper he asked if I could stop back after my route. I said sure. He always tipped me when I sucked his dick so I was fine stopping back after my route. Come to find out that was the first time I was gonna get fucked.
I was naked laying on his bed and he was naked over top of me. It definitely hurt going in since he was so big but he went slow. Once the initial pain was gone it felt fine. He fucked me for only a few minutes till he blew his massive load deep in my rectum. I was kinda shocked when he came in me but he informed me that is where you cum when fucking ass.
I got dressed afterwards and as I’m putting my tighty whities on he said don’t be surprised if your sore later today or tomorrow. Your hole is not used to being fucked yet. And told me cum might leak out into my underwear.
That went on for the next 3 years. I would get fucked every Sunday. Eventually I started getting fucked when I dropped his paper off. Definitely was weird at first talking to my other customers with a big load in my butt! Eventually I started stopping over at his house on Wednesday nights to get fucked too. He’d always tip me afterwards too so I obviously liked the extra cash.
But after 3 years I was done with my paper route but I actually would still stop over to get fucked. Till he had a heart attack and died unexpectedly. All my parents knew was he was one of my best customers be he tipped so well but they didn’t know why he tipped me or how often he tipped me.
After his death I found out from one of his neighbors that they knew he was married at one time and had one kid that was grown up and in the army. That woman neighbor also said she stopped back at his house one time and she saw him in his underwear. She said the guy was very hung in those briefs. It surprised her to see him in just his underwear. I to,d her he was in his underwear on his porch every Sunday morning when I delivered the paper. She laughed and said then you know what I’m talking about, he was definitely filling up his briefs way better then my husband. That woman was in her 60s. I said no kidding, makes a man jealous lol. I found out that a different neighbor of his actually sucked his dick quite regularly, a neighborhood single mom. She’s the one that told others he had a very big dick. That woman in her 60s also told me she heard he was bi sexual too. Obviously I knew that!
Every su day morning I was out walking my route by 5:30 am. I had about 60 houses I delivered too. I had the regular older people that would be outside drinking their coffee waiting for the paper or the ones that would open their door in just their underwear after I tossed the paper up on their porch. Wasn’t uncommon to see some open the door in their boxes or tighty whities in the morning to get their paper off the porch.
By 7:30 I’d have them all delivered. My one stop on Sunday mornings, it was a guy in his late 50s who would always be sitting out on his porch in just a white shirt and white briefs. I’d occasionally see his morning wood in his briefs some mornings when he stood up to grab the paper from me. He was definitely packing a big one but it never bothered me to see that since I’m a guy and I wore white briefs too. His house was very private as it was back off the road and surrounded by pine trees. So no one could really see him in his briefs.
By this point I had seen him for about 5 months in just his tighty whities on Sunday mornings. He was always very nice and talkative that early in the morning. I’d always be to his house a little after 6:30 am and he told me he woke up at 6:30 am on the weekends. I kinda moved my eyes towards his big morning wood and he smiled and laughed say that explains my morning glory to you, I just woke up.
The following Sunday I was collecting money for my route while delivering the papers. I got to the guys house at my normal time and he was outside as usual. He forgot to grab the money so he walked inside to grab it real fast. I waited in his porch. Now I don’t know how but I was initially invited in while he put the money in an envelope. But ended up sitting on a chair in his living room by his front door, his briefs were under his balls and his dick was in my face. Now when I said he was packing I wasn’t lying. He had a big fat white 9 inch dick. Huge balls and he was very hairy. My hand couldn’t fit all the way around his dick and I could only get he head and just a tad bit of his shaft into my mouth. I was holding his dick with one hand and trying to give his big dick a blowjob.
I must had done it right because minutes later he backed away from me, picked up a towel and jerked off while he coated the with cum. It was a lot of cum. He wiped his dick head off then pulled his briefs back up. We made our way back out to his porch where he sat back down and I left to continue my paper route. He thanked me for the paper and gave me my money plus some extra I later found out. He tipped me 40 dollars.
That continued every Sunday. I started just sucking him while he was sitting out on his porch. I’d just hold his tighty whities under his balls as I sucked him. When he got close to cummimg he’d have me back away and he’d blow his load on the porch floor.
Then after a few months of giving him blowjobs, one Sunday morning when giving him his paper he asked if I could stop back after my route. I said sure. He always tipped me when I sucked his dick so I was fine stopping back after my route. Come to find out that was the first time I was gonna get fucked.
I was naked laying on his bed and he was naked over top of me. It definitely hurt going in since he was so big but he went slow. Once the initial pain was gone it felt fine. He fucked me for only a few minutes till he blew his massive load deep in my rectum. I was kinda shocked when he came in me but he informed me that is where you cum when fucking ass.
I got dressed afterwards and as I’m putting my tighty whities on he said don’t be surprised if your sore later today or tomorrow. Your hole is not used to being fucked yet. And told me cum might leak out into my underwear.
That went on for the next 3 years. I would get fucked every Sunday. Eventually I started getting fucked when I dropped his paper off. Definitely was weird at first talking to my other customers with a big load in my butt! Eventually I started stopping over at his house on Wednesday nights to get fucked too. He’d always tip me afterwards too so I obviously liked the extra cash.
But after 3 years I was done with my paper route but I actually would still stop over to get fucked. Till he had a heart attack and died unexpectedly. All my parents knew was he was one of my best customers be he tipped so well but they didn’t know why he tipped me or how often he tipped me.
After his death I found out from one of his neighbors that they knew he was married at one time and had one kid that was grown up and in the army. That woman neighbor also said she stopped back at his house one time and she saw him in his underwear. She said the guy was very hung in those briefs. It surprised her to see him in just his underwear. I to,d her he was in his underwear on his porch every Sunday morning when I delivered the paper. She laughed and said then you know what I’m talking about, he was definitely filling up his briefs way better then my husband. That woman was in her 60s. I said no kidding, makes a man jealous lol. I found out that a different neighbor of his actually sucked his dick quite regularly, a neighborhood single mom. She’s the one that told others he had a very big dick. That woman in her 60s also told me she heard he was bi sexual too. Obviously I knew that!
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