The Paperboy

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I take the paperboy's virginity.
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It was the Friday after Thanksgiving and my husband had to work and my son had gone for the weekend to stay with some friends, so I took the time to start putting up the Christmas decorations in our home. It was quite warm that day since we live in the South so all I had on was a white, button blouse and a pair of loose, white gym shorts (the nylon silky kind) with no bra or panties. I was hanging garland around the fireplace when the front doorbell rang.

I went to the window and peeked out to see who was at the door, as I was not dressed properly for strangers. I was excited to see it was Mark, the paperboy, dressed in a t-shirt and shorts. Mark was eighteen years old and a real handsome young man. I'd had my eye on him for a while now. He seemed to grow a little taller and manlier every time I saw him. He was a real scrawny lad, but I thought he looked beautiful. He even had little wisps of hair growing on his chin now. I had been envisioning fucking him for a few weeks now. I felt a rush of warmth between my legs as I thought maybe this would be my chance to seduce him.

I let the blind slat down and unbuttoned the top three buttons on my blouse so the tops of my tits would be visible if I turned the right way. I answered the door and the look on his face was priceless.

"Hi, Mark. Is it time to collect for the paper this month?" I said.

"Yes ma'am, it is," he said, his eyes looking straight at my tits.

"Would you like to come in while I get you the money? How much is it?"

"It's $12.65 for this month. Are you decorating for Christmas already?" he said, as he looked around. I think he was trying to see if anyone was home with me.

"Yes, I am. But it's difficult doing it on my own. My son is away for the weekend. And my husband is working, so I have to do it all by myself. I wouldn't mind having a strong, good-looking boy like you to give me a hand. Shame you have to deliver papers instead," I said, as I left to go get his money, putting a little more sway in my walk to make sure he noticed my ass in the shorts.

When I returned, I made it a point of dropping one of the quarters as I handed it to him, and bent down to pick it up so he had a clear view of the tops of my cleavage. When I looked up and rose up slowly, his eyes were glued to the opening of my blouse.

"Thank you, ma'am. And this is my last stop if you need some help with those decorations. I'd be glad to stay with you," he said, trying not to look like he just got caught with his hand in the cookie jar. I thought this could be my chance to seduce him.

"Would you really do that for me, Mark? You're such good boy, and real handsome too, if you don't mind me saying," I said, watching his face turn red.

"Yes, I will, but no one has ever told me that I'm handsome before. Except maybe my mom."

"You mean none of the girls at your school have never told you you're good looking, handsome or sexy?" I said, watching him really blushed.

"No, none of them have ever told me that. Especially the last one," he said softly, looking down like he was scared to say the word.

I put my finger under his chin, raising his head so he had to look at me and said, "I think you're handsome and very sexy too. Can you say the word 'sexy', because it's the best compliment that you could give a person? Sit here on the sofa and let's talk."

He sat down on the sofa to my left and I made sure I sat close to him so our legs were touching and he had a good view of my cleavage up close. He kept trying not to look, but I watched him take several peeks at the tops of my tits and he kept his hands in his lap too as we talked so I knew he was getting excited. My nipples were hard rubbing against my blouse, and I was so wet between my legs.

"Mark, look at me. Do you think that I'm pretty and sexy?"

"Yes ma'am! I sure do," he said, looking back down.

"Mark, let's start by you calling me Donna and looking at me. You do like looking at me, don't you?"

"I sure do!"

"So why aren't you looking at me? Am I not pretty or what?"

"Oh, no ma'am, you're pretty!"

"And sexy?" I said.

"Yeah. But I've never seen a girl...I mean a woman like you. Ah, you know what I mean."

"Yes, I know what you mean, but I want to teach you to be confident with yourself when you are with a girl. Let me have your hand," I said, as I put my arm around him and took his hand in mine. His hand was hot and sweaty, but felt so good to me. I looked him straight in the eye and asked him, "Have you ever kissed a girl or a woman that you thought was as pretty and sexy as me?"

"Yes. I mean no!" he said, dropping his head again.

I placed his hand on my thigh and picked up his face again with my fingertips under his chin as I leaned over and kissed him lightly on his lips. I pulled back to gauge his reaction.

"Did you like that, Mark?"

"Yes ma'am. I mean Donna."

"Good!" I kissed him again with a little more passion and used the tip of my tongue to play with his lips. We kissed again and this time I pushed my tongue firmer against his lips and he opened his mouth. He was really kissing me back now, using his tongue to explore my mouth, which was a pleasant surprise. We broke that kiss and I just had to ask him, "Where did you learn how to kiss like that? Or was it just natural instinct?"

"Well, please don't tell anyone, but my older stepsister has been teaching me this summer."

"She did a good job. And yes, I like it very much, but what else did your stepsister teach you? Have you ever seen her naked and has she seen you?

"She would only let me kiss her, but we've seen each other naked a few times."

"So you've seen her pussy and she got to see your cock. Did you get to see her tits too?"

"Oh yeah. She's nineteen now and has an amazing rack."

"I saw you looking at the tops of my tits, right here, but would you like to see all of them? I'll let you touch them if you want."

"Sure!"

He watched me unbutton my blouse real slow, but I held it closed till I had all the buttons undone. I sat up on the edge of the sofa and, as sexily as I could, I took my fingertips and pulled my blouse off my shoulders, letting it slide down my arms and tossed it on the floor. He just stared at my large tits with the nipples hard and erect like two grapes sitting on a hill. I reached over and took his hands, putting them in mine as I used his to cup my tits so he could feel their firmness.

"Mark, that feels so good. How do they feel and look to you?"

"Wow, they're so big and hot. They feel real nice too."

"Good. I am going to show you how to rub a woman's tits to make her feel real good, and then I will show you something else to make them feel even better. Why don't you take off your t-shirt first so I can see your sexy body."

"Sure, yeah. Ok."

I showed him how to rub and cup my tits firmly with the palms of his hands and how to pinch my nipples with his thumb and forefinger at the same time. I let go of his hands and told him to keep rubbing them as I rubbed his chest with my hands. I was so hot I could have jumped his body, but I knew if I wanted to make him a good lover I had to take it slow at first and speed will come. He kept rolling my nipples as I told him to do it harder and harder and he let my hands explore his young chest and firm stomach.

"That feels so good. Does what I am doing to you feel good?"

"Yes, Donna, it sure does. I like making you feel good too."

"Good. Now I want you to kiss this nipple and suck it just like this," I said, as I took his hand off my right tit and sucked on his finger, running my tongue all around the tip. I pulled his head to my right breast and he began to suck on my nipple real lightly so I told him to suck it a little harder. He sucked it harder and I told him to bite it real easy with his teeth, but not too hard.

He was sucking my breast like a pro, as if he'd been doing it for years. And, God, it felt so good. He was rubbing and pinching the other one too. I let him have fun for a few more minutes because I wanted more and this can be done while other things are happening. I slid my hand down and placed it on his hard cock and got another surprise. He was packing a good-sized cock for a boy of eighteen. When I did this he stopped sucking and looked up at me.

"Do you like me doing this to you? Or would you like for me to stop?" I asked as I began to rub his cock through his shorts.

"Oh, no, it feels real good. But it's a little uncomfortable all cooped up in my shorts," he said, trying to rearrange his body to get more comfortable.

"How about if we just take off these shorts and give that big cock of yours more room. I want to feel it in my hand, if you'll let me," I said, reaching down and holding them firm as I slid the zipper down. I dropped down on my knees on the floor in front of him.

I grabbed the sides of his shorts and underwear as he got the message and lifted his ass off the sofa just high enough for me to pull them down his legs to his feet. His cock sprang free, slapping his stomach as I threw them on top of my blouse forming a clothes pile.

I don't know if he saw my eyes light up or not, but I was looking at least six inches of good, hard, thick boy cock, just waiting to be sucked.

"Oh my! Mark, you're well hung for an eighteen-year-old," I gleamed as my right hand went to his hot rod and my left cupped his tender balls. I started to stroke his cock while massaging his balls as I asked him, "Does that feel better, babe? Do you mind if I play with your cock?"

"Oh, I don't mind at all, In fact, you can do anything you want."

"Good. Now just lay back and let me kiss and suck your cock, just like you did to my titties."

I grabbed the base of his cock pulled it up straight out from his groin and kissed the tip. I stroked it a few times until I saw a drop of pre-cum oozing out of his piss slit. I looked up at him, took my tongue and licked it up. Still looking at him, I said, "You taste so good! Have you ever had someone suck your cock before?"

"No!" he said, breathing hard.

"Well, let me be the first to suck on this hot tool of yours. It sure looks good enough to gobble on."

I lowered my head back down and took him in my mouth, swirling my tongue all around the head of his cock. I had his attention then so I started giving him one of the finest blowjobs I could. I sucked him and licked his cock until I knew he was close to coming.

When I took my mouth off his cock, his look was one of disbelief and he said, "Oh! Please don't stop."

"I'm not, Mark. I just wanted you to know that it is all right to come in my mouth. I want to taste and swallow all of your young, hot cum," I said, and then lowered my mouth back down on his cock. I really started sucking his cock hard then, and I felt his cock throb so I pulled back so my lips were right behind the head, tickling the underside of the helmet-head as he let loose one of the first of many spurts of hot cum. His cock kept pulsing and spurting till I sucked him dry. But being so young and virile, he was still hard as I raised my head up and kissed him on the lips so he could taste himself on me.

I sat back on my heels with my hands on his cock and watched him laying there just panting as he tried to get his breathing back to normal.

"How was that? Did you like it?" I asked.

"That was great. So much better than jacking myself off, for sure."

"Well, would you return the favor and lick this for me?" I stood in front of him and dropped my shorts, showing him my shaved pussy.

"I guess so. But you will have to teach me what to do, because I've never done it before. Just seen some videos on the internet," he said, all wide eyed and licking his lips, eager to get his tongue up my cunt.

"I'll teach you how to please a woman with your mouth. You'll have them begging you to fuck them when you get done."

"Does that mean you are going to let me fuck you?"

"If you do real good at eating my pussy and sucking my clit, I might let you," I said, as I took his hand and lead him to my bedroom, knowing the whole time that I was going to fuck this young lad's brains out.

I sat down on the edge of the bed and told him to kneel between my legs so I could show him the important parts to pay attention to. I spread my legs and told him to just touch my pussy. He touched me so softly that I could barely feel it, so I took his hand and showed him how to cup my mound just the way he did my breasts.

I told him to sit back and watch. I pulled my pussy lips open and told him to see how wet I was by running his finger up and down the pink area. After he did that I told him to pay attention to the next part and pulled the hood back to show him my protruding clit, which was now in need of some tongue attention. I slid my finger into my pussy, getting it wet, then brought it back up to my clit as he watched me massage it to make it more erect.

"Mark, do you see this little nub which looks like a small bean?"

"Yes. The thing under that skin there."

"Yes. That's my clitoris, or clit as I call it when I want sex. I usually call it my clit. This is where I want you to put your mouth. Just do as I tell you to do, and it will make me want to fuck you if you do it just right. Do you think you can do it?"

"Yes, I'll do whatever you tell me to do."

"Good. Now just use the tip of your tongue and lick from the bottom to the top of my pussy. Then put your whole mouth over my clit and suck it lightly at first and flick it with your tongue till I tell you to do it harder and faster."

His face was between my legs in a flash and he licked slowly up my wet slit to my clit, just like I told him, until his hot mouth was sucking on my clit. I told him to run the tip of his tongue all around the hard little button and then flick it a few times up and down over my clitty.

"Oh! Mark, that feels so good. Now move your tongue down to my pussy hole and stick it in and out as deep as you can until I tell you to suck my clit again."

It didn't take him long to learn how to eat a pussy. After the third or fourth lesson on what to do, he had me on the verge of orgasm. I grabbed his head and told him to suck my clit until I told him, "Now", then open his mouth and put it over my whole pussy when I came.

"Oh, yes, suck my clit. Oh my God! Now suck my pussy!" I screamed, as I squirted my cum into his mouth. He pulled back, surprised at first, but went right back down on me sucking all my cum up. I lay back and he stood up and I looked up at his wet face and I told him to come up and kiss me so I could taste myself on his lips. He kissed me and I felt his hard cock on my leg. I looked into his eyes and asked him, "Would you like to put that hard cock in my wet pussy?"

"Yeah, sure I would."

I moved up on the bed, spread my legs and told him to get between them. He was leaning over me, and I took his hard cock in my hand and told him to come down until it touched my pussy lips, but not to put it in yet. I felt the tip of his cock touch my pussy and I just grazed the head up and down the entire length of my slit to get it nice and wet.

He was trying to put it in but I kept stopping him telling him not to be in such a hurry. When I had him ready I took his cock and placed it at the opening of my love hole and told him to do as I said. He nodded and moaned at the same time.

"That's it. Hold it right there at the entrance of my pussy. Now let it slide in real slow so I can get use to you inside of me." It felt so good to have that young cock in me. He just lay there on top of me breathing heavy.

"Now just start pulling it in and out real slow, but not all the way out. Make sure the head stays inside my pussy."

He began to move his stiff rod in and out of my wet hole.

"That's it, real slow. Oh, Mark, you feel so good in my pussy."

"Donna, I'm going to cum soon if I keep doing this."

"Ok, just pick up the pace now. Go a little faster and then fuck me hard and fast when you're ready, but hold back from coming for as long as you can."

I grabbed his hips, pulling him into me as hard as I could because I wanted to come when he did. He was really fucking me hard and fast now, and I felt his cock pulse so I knew he was close.

"Tell me when you're ready and I will fuck your brains out, baby."

I watched his face so I knew when he was going to squirt his cum in me. He went stiff and his face distorted as I pulled his ass hard down, driving his cock deep in my pussy as we both came in unison. Squirt after squirt of his cum just kept on coming as I bathed his cock with my own girly juice. He came so much that it was leaking out around his cock and down the crack of my ass. When he was finally done, he collapsed on top of me breathing like it was his last. I rolled him over onto his back so we both could catch our breaths. I rolled up on one elbow beside him and asked him, "Well, how was it? Your first time to fucking a woman?"

"It was just great, and it felt so damn good. I want to do it again."

"Rest for a few minutes and we'll see."

I put my hand on his cock and played with it as it started to get hard again. Now that's what I love about youth and younger guys -- their cocks never seem to dwindle.

As I stroked his cock I eased down and took him in my mouth again, cleaning our combined juices off his hardening cock. I sucked him until he was hard again, ready for more action.

I straddled his body, kissed him again and went up on one knee as I wrapped my hand around his cock, aiming it at my pussy and lowered myself down on him. I leaned forward, putting my hands on either side of his shoulders so I could fuck up and down on his young, hard cock for a few strokes. Then I switched so I was completely impaled on his cock and rocked back and forth so I could feel his hardness against my clit.

I knew from the first few strokes that it wouldn't be long before he and I would come again. I kept it up harder and faster till we both come again. We lay there for a while before we needed to get cleaned up because it was late. We showered together and got dressed and I walked him to the door. At the door he turned around and asked could we do this again, and I told him anytime that my husband was away from home, he was welcome to come round and fuck me. I leaned in and kissed him goodbye.

Since then we have been together twice more when my hubby was off playing golf on a Saturday morning. We have a plan that when I call telling him I am missing my paper, he brings one right over so he can fuck my hot pussy with that young, hard, hot cock.

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naughtyandy4unaughtyandy4u10 months ago

As a paperboy the closest I came to this was getting flashed a full body nude. Her sister? (early 1970's) who was only wrapped in a towel herself said "oh she does that all the time". Great story. I think any boy / man who had this experience would relish it.

Thanks for the read

AnonymousAnonymousover 2 years ago

HOT!

AnonymousAnonymousover 2 years ago

I used to have this fantasy when I was a paperboy. It never happened but I loved the story.

AnonymousAnonymousover 2 years ago

This was amazing and I enjoyed the innocence as Donna showed Mark what he needed to know and what Donna wanted.

AnonymousAnonymousalmost 4 years ago
Me too

I think because I looked half my age and virginal, this kind of thing happened to me several times. My first seductress was a babysitter, then my older brother's girlfriend, a married family friend that I was often 'lent' to for help about her home then some girls my age I dated, a music teacher at my High School. After High school it was two different married coworkers who were convinced I was a virgin. On their defense, by this time I felt like a professional virgin. In college I 'lost' my virginity a few more times. It was my experience of youth to know that there is a segment of woman who are eager to make men out of boys.

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