Paperboy at the Door

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Paper boy caught peeking.
2.7k words
4.5
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35

Part 1 of the 2 part series

Updated 06/08/2023
Created 09/20/2017
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pdiddyd55
pdiddyd55
250 Followers

This is a story of my first group. Well, if you don't count the handjobs that I received from Mary in the front seat of my Chevy Nova, its actually my first time.

It's the summer of '69. I'm in Detroit, or actually a nearby suburb. The Tigers won the World Series the year before, so life is good.

I've graduated from high school and am getting ready to go to the University for freshman year. To earn some spending money, I've been caddying at the local Country Club. A couple of weeks earlier, my younger brother broke his arm. My mother insisted that I take over his paper route until I go to school. The money is not as good as caddying, but I can't so no to my mother. As a result, I've been getting to the Club at 6 each morning, so that I can get a loop by 7 or 8. I am usually off the golf course by noon.

At the time, Detroit had 2 daily newspapers. One was a morning edition, and the other was delivered in the afternoon. My brother's route was the afternoon paper. So, by 2 o'clock, I am at the distributor's office loading up my paper bag and heading on out. I had this route before my brother took over, so I know most of the homes, and what their preferences are for deliveries. The neighborhood is affluent, although I did not live in that neighborhood. Much of the route was just riding down the sidewalk and tossing a paper onto the front porch, or at least within sight of the front door. There were a few homes that required a little bit more. One of those was near the end of the route. The lot that the house was set on was larger than most in the neighborhood, and it had tall hedges that hid most of the house from the street and sidewalk. There was a gap in the hedges wide enough for the driveway, and this is the way that I entered the property. The owner's, Mr & Mrs Walters asked that their paper be "dropped" on their front porch. This involved pedaling into a paved courtyard, up to their front steps and tossing it to their door.

On this day, there was a vehicle parked in front of their porch, and I decided to toss the paper over the top of the vehicle. Wouldn't you know it, but the paper slid right off the porch into the shrubs. Damn, I had to retrieve it or I might get a call against me stating that I did not deliver. I parked my bike, and ran up to the porch and tried to get the paper by reaching down. As I did so, I heard some noise coming from one of the windows. In 1969, not many houses had central air, and it was typical that windows would be open to cool the house.

Now I wasn't a virgin ... well, technically I was, but I've seen plenty of blue movies and I recognized the sounds that I was hearing. I KNOW that what I was thinking of doing was wrong, but I was an 18 year old kid, with hormones running wild, so I just had to take a peek. There was a window down near the end of the house that I thought the sounds were coming from, and it was just a simple matter of sneaking behind the bushes to catch a glimpse.

Once I got there, I was not disappointed. Mrs Walters was naked on the bed on all fours. Behind her was NOT Mr Walters. The gentleman in the erotic scene in front of me was probably 10 years younger and fit. I was on the baseball team in high school, and saw many young bodies in the gym lockerroom. This guy would have been right at home among them. As I watched, he withdrew and had her turn around to take him in her mouth. OMG. To this point in my young life, it was the biggest cock that I've ever seen. Mrs Walters, being in her late 30s was looking mighty fine as well, with her tits hanging down. In my current position, I couldn't quite get a glimpse of her love canal, and I stretched my neck in order to do so. I was mesmerized by the sight.

The guy moved her off his cock, and lifted her upper body up so that he could kiss her. He then spoke into her ear, and left the bed. She rolled over onto her back, and started rubbing her pussy. This finally gave me the view that I was hoping for. Needless to say, I was hard as a rock. I was considering rubbing one out right there, but was worried that I might be seen from the street. I decided to take a peek behind me to see just how secluded I was. When I did, I saw the guy from inside, wearing a robe and watching me from the other side of the bushes. How the fuck did he get there? And what kind of deep shit am I in now?

He motioned for me to come out. My immediate thought was to run, get the hell out of there, but I was just a kid and used to taking orders from adults, even if those adults were just in their 20s. Besides, he was bigger than me, and I had no way of getting to my bike without trying to race past him. So, reluctantly, I worked my way out of the bushes and came up in front of him. He ordered me inside. Oh boy, now the shit is going to hit the fan. I saw all kinds of scenarios running through my head ... loss of my scholarship, maybe being arrested. I mean what kind of pervert goes around peeking in windows?

After entering the house, the guy guides me back to the bedroom that I had been peeking into. There, now also in a robe, was Mrs Walters. When she saw me, her eyes got big and she said "Jack?". Yes, my name is Jack ... 18 ... horney ... and now fucked royally.

Mrs Walters: "What did you think you were doing, Jack?"

Me: "I'm sorry Mrs Walters. I wasn't thinking." As if not thinking was an excuse for being a pervert.

Mrs. Walters: "How long were you out there?"

Me: "Only a couple of minutes. I swear. I accidently tossed the paper ..."

Mrs. Walters: "Never mind why ... exactly what did you see? Did you see Alex (that must be the guy's name) fucking me?" OH MY GOSH ... she used the F word.

Me: "Yes ma'am"

Mrs Walters (softer now): "Well, did you enjoy what you saw?" And as she said this, she opened her robe.

My jaw must've dropped to the floor, because Mrs. Walters started to smile. Later in life, I would get a sense that that smile would lead to good things, but at this time in my life, all I could do was stare.

Mrs. Walters: "Jack. Do you enjoy what you see?"

All I could do was mumble a yes while I nodded. I glanced over at Alex, and saw a big smirk on his face and a big tent under his robe.

Mrs. Walters: "Jack ... would you like to touch them?" Now its not like I've never touched a breast before, but I never touched a "bare" breast before, and in spite of being extremely nervous, I took a hesitant step forward. Mrs. Walters waved me towards her. I reached out and finally, for the first time in my life, touched a woman's breast. I was so hard, I thought that I would cum at that moment.

Mrs. Walters (later she told me to call her Karen), put her hand over mine, and helped me caress her breast, gently rubbing the nipple. Then she grabbed my other hand and had me work both breasts. I think Alex must have killed me somewhere along the way, and I was now in "teenage boy's heaven".

Karen whispered in my ear that I should take my clothes off. She would like to show me more. Here we go! If this isn't replayed in my wet dreams for the next 5 years, I am not normal. I quickly did as she suggested. I would do ANYTHING for Karen. Little did I know at that moment exactly what Karen would ask me to do.

Karen backed me up to the bed and had me lay back. She dragged her nails over my nipples, sending a shiver down my body, straight to my cock. Whoa! She leaned over and took my nipples into her mouth and teased them. How the fuck was I to know that guys would enjoy having their nipples played with. Once again, I was on the verge of cumming without my cock being touched. Karen's robe had fallen off by now (or did she remove it without me seeing), and I attempted to reach down and play with her tits again. She noticed my groping and moved around so it was easier for to grasp those magnificent orbs. Have I told you just how great those tits were? In spite of her old age (late 30s?), they were pert and succulent. She had obviously taken good care of her body, because I could not detect a single ounce of fat. In my mind, she was a 38DD, but when I compare her to partners in later life, she was above average.

Karen then started feeding one of those luscious tits to me. I wanted to smother myself in it and I heard her and Alex chuckle. Alex? Oh fuck. He's still in the room. While I wondered what he was up to, I was too busy to look around.

After I got her breasts nice and wet with saliva, Karen asked me if I've ever participated in oral sex? Of course I lied and said "yes, a couple of times." I think that she knew I was lying, but at this point ... Who cared? She moved me around so that we were in a 69 position, with her above me. She then started to fellate me. Fellate? Yeah, she was blowing my fucking brains out. But she knew how to do it. She would back off before I came, keeping me at the boiling point.

Then Alex asked me if I've ever licked a pussy? I had to admit, that I had never had the chance to do so. He pointed out the fact that Karen's pussy was just above my head. Why don't I give it a try? Just lean in, and lick along the length of the slit. I lifted my head, and tongued the bottom of Karen's cunt. Well it was the bottom, because it was pointed down, but as I learned later, I placed my tongue directly onto to Karen's clit. This caused her to jump a little, and I heard a slight moan come from her. Alex suggested that I lick from the bottom (clit) to the top, and I tasted some of her juices. At the time, I did not know what this was, but it seemed to be pleasing her, so I just kept it up. After all, she had my dick in her mouth, I just thought I was being a good guest.

The next thing that I knew, I saw Alex's rather large cock just above my head. He reached down and tapped my head, so I moved it back to the bed. He then moved it forward and attempted to enter Karen from behind. By this time, she was so wet, he didn't have to try hard. So right above my face, I was watching Alex as he pumped into Karen's snatch. I was watching Alex's big balls and they swung back and forth with his pumping. Meanwhile, Karen has started lathering up MY balls, while giving me a slow handjob.

Alex suggested that I start licking Karen's pussy again. I wasn't sure how I was going to do this, especially with that mammoth organ moving in and out of her, but once again, I wanted to be a good guest, so I did what I could. I stuck my tongue out as far as I could, and moved my head around so that I could at least get to the bottom of her opening (again her clit), and started licking. It was not easy, but as horney as I was, I was more than willing to get a stiff neck from trying.

Alex's balls were slapping me in the face, but I didn't care. Karen was back working on my dick, and this time I think she was going to let me cum. Long before the designer drug "ectasy", I was in bliss. Once or twice, Alex came entirely out of Karen's hole, and his dick flopped down onto my mouth and tongue. Later in life, I realized that he wanted me to take him into my mouth, but I was only interested in Karen at that point. I remember licking the tip, but nothing more, before Alex again penetrated Karen.

By now, I was at the point of no return, but I didn't think Karen would want me to cum in her mouth. I tried to tell her, but she just doubled her efforts, and before I knew it, my 18 year old cum was coating her throat. That must've set something off in Karen, because I heard her start moaning, and her body was starting to buck against Alex. Alex picked up his pace, and I still had my front row seat of the action. I was watching that cock drive in and out of her at an ever-quickening pace. At one point, I noticed that Alex's balls were no longer swinging over my head. They seemed to have risen up into his body. Then, I heard a guttural sound coming from Alex, and I saw him give a mighty shove into Karen. He held it for a second, then withdrew and drove in again. Once more, he withdrew, but this time, he came all the way out. I then realized, what had been happening above me, as he proceeded to shoot a couple more jets of cum onto my face. With Karen above me, I didn't really have anywhere to go, so I just closed my eyes and let it happen.

Some cum got onto my lips, and so help me, I couldn't help myself. I licked it and found it wasn't that bad. Then Karen decided to lean back and basically sit on my face. She started rubbing her pussy all over my mouth.

Mrs. Walters: "Oh eat me Jack. I've got one more in me." I later figured out that she meant one more orgasm, but at that point, I was still in the submissive teenager mode, and just did what I was told by my elder. She bounced up and down on my tongue, and each time I could sense more of Alex's cum leaking out of her. I was having way too much fun to worry about something like that, so I just kept licking until finally Karen tensed again and fell forward.

I was worried that she had passed out, but only found out that she was just content, and needed to relax. I attempted to start licking her pussy again, and she moved away. Alex explained to me that she was over sensitive at this point, but if I was interested, she would be ready to go again in a little while.

I asked what time it was, and found that I had been there for over an hour. Being the ever vigilant businessman, I realized that I had a few more papers to deliver, and my mother was expecting me home for dinner. Karen took me into the shower, washed me off and thanked me for the afternoon. Can you believe this? She actually thanked ME!!

I left Alex and her, and in a month I had left for school. I never saw Alex's car at their house for the remainder of the Summer, so I don't know if they were still meeting. I can only tell you that I never got together again with them ... Well, I did. But only in my wet dreams.

pdiddyd55
pdiddyd55
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AnonymousAnonymousover 6 years ago
Pdiddyd55 correct. Anonymous wrong.

To anonymous from 10/1: Read it before you criticize. The author said it was summer of 1969 and that Detroit had won the series the year before. That would be 1968. To Pdiddyd55: good story. Hot sex. Write more!

AnonymousAnonymousover 6 years ago
Not 1969

Detroit won WS in1968.

Story is real steam hot!!

AnonymousAnonymousover 6 years ago
Ah...the paper route...

In the early '60's I had a paper route. I was 14 and every so often one of the wives would be home when I came to collect. I caught my first glimpse of boobs and butt by these women showing off. I had one woman who would phone once a week to say her paper was not delivered. I would have to go over and personally hand her a new one. Her clothing got more and more revealing each time. The day I wrecked my bike and showed up bleeding, she asked me inside to clean me up. I had really cut my knee so she had me remove my pants. As she bent over cleaning the wound I saw right down her robe. Instant boner. She saw it in my briefs and began rubbing it. Next thing I know she had me out of my briefs and in her mouth. I may have lasted ten seconds. She asked me to come back the next week. I did. By the end of that year she taught me everything about being a man......yet I was still a boy.

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