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Helping her Son Get over His Shyness
Part-1 -of-2
The Problem
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I’d gotten pregnant when I was 16 and ‘to do the right thing’ became a child bride. We tried to stick it out, but an 18 year old and a 16 year old were both far too young to be married. Gary and I lasted until our son, Charles was in the first grade, and then we finally got a divorce. Immediately after the divorce Gary, my ex got a job transfer and moved out of state. Once he moved, Gary met someone more suited to him and was soon re-married and raising a new family. Don’t get me wrong, even though we got a divorce we remained friends and Gary always paid his child support. Even though his daddy and I remained friends, and despite my protests to the contrary, Charles still for some reason blamed himself for the divorce. So, between that, his feeling left out because his father was re-married, and for all practical purposes not having a positive male role model, growing up, Charles had never had any confidence in himself. Although he had a cute face with a boyish cupid bow shaped lips and a nice head of dark curly hair, his body was almost pubescent in its hairlessness. Even though he’s now 18, Charles still comes off as younger in both looks and the way he acts. He’s only 5-foot 6 and so slim and effeminate looking that he’s often mistaken for a girl. His total lack of confidence made him come off looking like an immature kid.
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I don’t suppose it was really his fault. When he was growing up there was never anyone around to teach him how to play sports and stuff that fathers traditionally teach their sons. Even though I dated a lot, the guys that I dated were more interested in getting into my panties than they were in being a surrogate father to my son. A couple of guys saw being nice to Charles as a ticket to my bed, but once they got what they wanted he was history. All this did was to further erode his all ready low self-esteem. So, as a consequence, Charles was afraid to try out for sports or indulge in any of the masculine pursuits. Naturally this lack of confidence spilled over into all facets of his personal life. He was afraid to join the band, because he was afraid he couldn’t measure up. He wouldn’t go to the school dances because he didn’t think he could dance well enough. Even if I forced him go, he’d spend the entire evening hanging out at the refreshment table instead of dancing with the girls.
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Given his past history of shyness, I have no idea why his revelation was such a surprise to me, but it was.
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It all started when my next-door neighbor’s 18-year old niece came to visit her. The niece was a nice enough, and no one could blame her for being shy and insecure; she had a sweet face but she was a tiny bit on the plain side. Even though a little under endowed, she still had a nice trim figure. Because of her shyness, she hadn’t dated very much, a situation that my neighbor decided to correct. Taking matters in her own hands, her aunt started scouting around for a suitable guy to fix her up with. And, as I‘m sure that you’ve guessed, she picked Charles.
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As a favor to our neighbor, Charles took her niece out a few times, but the dates were spaced out a couple of weeks apart, as if he were in no real rush to see her again. Eventually her aunt asked me, “What’s up with your son? Doesn’t he like my niece?
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Not knowing how to answer, I decided it was probably time for me to get involved… whether I wanted to or not. Later when Charles got home, I sat him down for a mother/ son talk. Once I broached the subject, I told him that, “If you don’t like the girl, you don’t have to go out with her. It’s not like there’s any kind of requirement or anything. Hell, you don’t even have to go out with girls at all if you don’t like them” Even though Charles was 19-years old, trying to get anything out of him was like talking to a 10-year old kid. Looking down as he scuffed his shoes in the carpet, he whispered, “She’s OK.”
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Trying a different track, I told him that, “If you do like her, you could show her that you do by seeing her a little more often.” Instead of answering, he just nervously moved his foot a little faster around on the carpet, and then mumbled almost under his breath, “Things are OK the way they are.”
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There was undoubtedly something strange going on here, but for the life of me, I didn’t understand what. “What’s the problem?” I asked. Well, if I repeated the next twenty minutes of our conversation I’d bore you to tears. Let’s just suffice to say that I’ve seen teeth pulled easier. It took awhile for me to get the real problem out of Charles, but I finally managed. It turned out that Charles was hesitant about dating the young girl because of certain expectations that she seem to have for him. Cutting to the chase, she was being sexually aggressive and, Charles was hanging back because he didn’t feel that he was up to the challenge. I couldn’t believe it, my19 year-old son was a damn virgin. He’d never gotten it on with a girl before. As I said earlier, it shouldn’t have surprised me. I knew Charles was shy and insecure and that he had always been afraid that he wasn’t good enough for the band, for the athletic team, for dances---- naturally he wouldn’t have been aggressive enough to have had sex, either. Knowing his own inexperience, of course he didn’t feel equal to fucking our neighbor’s niece.
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Now the big question was what to do about it? It was a spur of the moment decision, but I decided to do the only thing that made any sense was to teach him about sex myself.
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At first Charles was shocked by the suggestion that I, his own mother, should give him lessons in the finer points of sex and how to satisfy a lady.
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I’m still a damn good looking 34 year-old, even if I do say so myself. I’m tall for a woman, 5’ 9’, and since I workout at the gym regularly, I have a firm supple beautifully curved body, a slender waist with a flat stomach, and trim hips. My full-bodied red hair is long and wavy and my neatly trimmed pubic hair, like all natural red heads is that orange shade that guys seem to find so intriguing. Some guys thought my breasts were small, but they were firm and shapely with nipples that stuck out like pencil erasers when I get excited. And when it comes to sex, I’m always excited.
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Knowing that it was going to take something drastic to get this thing started and never one to be shy, I slipped my sundress over my head and dropped it carelessly on the floor. As I stood in the middle of the living room, in my lacy bra and bikini panties, I glanced over my shoulder and saw my son’s face turning beet-red as he stared at my luscious ass. As my teenage son watched, I unhooked my bra and let it fall slid my shoulders. As I let it drop to the floor, I could feel Charles’s eyes boring into my bare back, as he imagined what my bare breasts looked like. A second or so later I slowly slipped my fingers delicately into the waistband of my flimsy silk panties and sensuously lowered them off my hips so that Charles would get a good look at my shapely bare ass. I could hear poor Charles’s breath coming in gasps as I eased my panties slowly down my and let them fall to the floor. As I stepped out of them, I turned so that Charles could get the full effect of my pert breasts and my succulent pussy all at once. I could tell by the look on Charles’s face that he’d quickly changed his mind about having his mother teach him about sex. And, mother or not, one look at my beautiful naked body, and Charles was sporting a boner the size of a telephone pole. When I reached out and touched his huge hard rod with my fingers, his body trembled so intensely that I thought he was going to cum in his pants right then and there.
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With a little smirk, I purred, “I’d better bleed the pressure off that thing before it goes off and hurts someone.” The horny little bastard was so busy staring at my naked body that I’m not even sure that he even heard what I said. I felt so sorry for my poor son; he couldn’t seem to decide whether to stare at my perky breasts or my luscious slit.
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Dropping to my knees in front of my still clothed son, I yanked down his zipper, and as I was tugging his erection out of its denim prison, I cooed, “Let me get a load out of your balls real quick before they explode.” His eyes got as big as saucers and he gasped with a combination of awe and lust when my hand encircled his swollen erection and guided it between my lips and into my warm mouth.
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Helping Her Son Get Over His Shyness
Part-2 -of- 2
The Solution
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As the head of his surprisingly big cock pierced my soft red lips, Charles suddenly grabbing my hair and violently thrust forward and filled my surprised mouth with most of his hard fat shaft. I could feel my jaws stretch as its head struck the back of my throat. My mouth was so full that I could feel the throbbing of his blood coursing through its bulging veins. Keeping his fingers wrapped in my hair, Charles began to clumsily thrust his hips back and forth as he forced his raging erection deeper and deeper down my willing throat. His cock was swollen to such a tremendous girth that I knew he wouldn’t last much longer, but that was OK. I was just trying to remove the urgency so I could take my time and show him how to do it right.
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Charles was so excited about having his cock in my mouth that with each stroke he was ramming his cock harder and harder down my throat, groaning so loud that I was afraid that the neighbors could hear through windows. From the look on his face, Charles wasn’t worried about anything but cramming his cock as far as he could down his mother’s throat. When I gently squeezed his balls, his orgasm was swift and furious. As I knelt there with his cock held firmly in my mouth, my 19 year-old son’s teenage balls spewed what seemed like a gallon of thick, hot gooey cum down my throat. And to my utter amazement he pumped so much cum down my throat that I thought I’d drown. By the time that he was spent, cum was leaking out of the corners of my mouth and oozing down my chin. What was even more amazing was that his erection was still as rigid as when I first stuck it in my mouth. When I’d finally sucked out every last drop of this particular orgasm, my son pulled his cock out of my mouth as ready for action as he’d been when we started.
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Since he was holding it right in front of my face, I could easily see that his weapon was still primed and ready.
As I stood, I said, “Now, the first thing that you need to remember about women is that we are like ovens, we need to be pre-heated before you can fuck us. We need foreplay. And, whatever else you do, whether it’s kissing, or stroking, or whatever, you have to pay attention to her clit. You do know where a woman’s clit is, don’t you?” I asked.
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With a crimson faced, Charles shyly shook his head and mumbled, “no.”
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God, I thought as I sat down on the couch and spread my legs, doesn’t my son know anything? “This is my clit,” I said, holding my pink lips apart with one hand and fingering my clit with the other.
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When I suggested that he, “Sit down here and rub it,” poor Charles almost tripped over his feet to comply. When he did touch it, like most guys, he rubbed much too hard.
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“Easy,” I snapped. “You’re not squashing bugs, for Christ’s sake. You have to rub it gently…. Gently but continuously… and for goodness sake, stay on target. Most guys have a tendency to let their finger slip off and rub in the wrong place. Now, practice staying on the little pointy tip.”
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He might have been a bum, but I’ll say one thing for Charles’s father, he knew how to please a woman. And, like a chip off the old block, Charles was a quick learner.
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“It’s easy to tell when a woman’s getting hot,” I explained, “First of all, notice how wet and gooey I'm getting? That’s a good sign that I’m getting hot. And see how deeply colored I am down there now? That’s another thing to look for.”
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“Can I fuck you now?” Charles suddenly blurted out.
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With a flirtatious laugh, I answered, “Sure, why not? But, remember that most women don’t like it when you say ‘fuck.’ When you want to fuck a girl, call it ‘making love.’
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Moving down to the plush pile carpet, I stretched like a contented cat, and then spread my long shapely legs so that Charles could have complete access to my wet and waiting pussy.
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As poor Charles awkwardly mounted me, I could tell that he was going to have trouble finding my hole, so I instructed him to, “Use your hand to ease it in.” Even using his hands, the poor boob still jabbed at me unsuccessfully a few times before I gave up and guided it in myself.
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“Now that it’s in,” I cautioned, ”let the woman set the rhythm. You start off slow and you don’t try to rabbit-fuck her,” I added, “unless, that is, she speeds up the pace herself. You always want the woman to cum first and, more than once if you’re good enough.”
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As I undulated beneath Charles, I held him by the cheeks of his ass and pressed upward until I could feel his fat erection filling me up.
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Despite my instructions, Charles soon got carried away. Even with me telling him to, “Slow down! You’re going too fast! Take it easy!” He continued to pound in and out of me at such a rapid rate that he would all too quickly be cumming. Sure enough, he was quickly blowing his second load into my raging pussy…. Long l before I was ready to cum.
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Although I held on and urged him to, “Fuck me! Damn it! Don’t stop! Keep fucking me!” it was to no avail. I could feel him slowing down and growing soft.
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As he rolled off, I told Charles that, “If you ever want to fuck a woman again, you better never leave her hanging like this. No matter what, you absolutely have to get her off. So, in a case like this there’s only one thing for you to do… and that’s to get her, or in this case me, off with your tongue.”
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To my surprise, despite the fact that my pussy was over flowing with his cum, Charles moved between my legs and went down on me without batting an eye. My butt was barely on the couch before Charles’s face was in my lap and his supple tongue was eagerly flicking his jism out of my rampant pussy.
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Using his hair to guide his action, I reminded him to, “Remember what I said about staying on target. That counts here, too.”
As excited as he was, he still did a pretty good job of staying on target and further enraging my lust-swollen clit. The soft orange fuzz covering my crotch was matted with white streaks and blobs of Charles’s cum when he pushed his face into my lap and covered my fuzzy slit with his open mouth. First he washed all around my gaping slit with his tongue. Then he tongued the stickiness from the inside of my pussy as he eagerly licked and sucked on my puffy outer lips. With a little yip of pleasure I lost control as my hips started thrashing and my cunt smeared the thick cream that was now gushing from my pussy all over Charles’s face.
When I finished cumming, instead of getting up, Charles laid his cream covered face on my naked thigh. Then like a little kid seeking his mommy’s approval, Charles grinned with a self-conscious pride at having gotten me off with his tongue.
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As I felt the heat from his face radiating through my thigh and up to my rapidly awaking pussy, I proclaimed, “A few more lessons, and you’ll be fit to fuck any woman around!” When he heard the words “A few more lessons” Charles’s boyish grin got even wider. As I sat there stroking Charles’s curly hair, and savoring the heat of his face against my thigh, I found myself wondering if a horny 19 year-old boy was capable of more than two orgasms.
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Then with a wicked smirk, I pushed Charles onto his back and slide shamelessly down between his out stretched legs. Leaning forward, I took one of his nipples between my lips and began to kiss and lick it like a baby past his feeding time.
Charles got so excited that he couldn’t keep that he was soon cupping and kneading my breasts.
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Charles’s hairless chest was so incredibly smooth and soft, that it was like the satiny flesh of a baby’s butt. As I happily devoured his nipples my fingers danced down the soft flesh of his hairless body to the clump of crinkly pubic hair between his legs. I still couldn’t get over the contrast between Charles’s hairless child like body and the huge set of hairy man balls that I was cupping in my hand. When he was dressed, no would possible guess that he was sporting a man size 8” cock to go with those man size balls.
Easing my hand up, I started to slowly stroke Charles’s rapidly hardening cock.
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When Charles placed his hand on the top of my head and gently pushed, my hot lips were soon following my dancing fingers down the length of Charles’s tense body. Taking his semi erect cock in my hand, I flicked my tongue out and licked and kissed the big purple head. When Charles moaned, I slipped the head of his cock between my lips, and deep into my demanding mouth. As my son’s enormous cock filled my mouth, I began to work my tongue and suck simultaneously.
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By now Charles and I were both huffing and puffing from excitement. Without taking Charles’s cock out of my mouth, I twisted around and placed my knees on both sides of his head. When here I lowered my gaping pussy onto Charles’s face, he dove right in. His tongue was soon driving me crazy as he licked my puffy pink lips and sucked on my blood-swollen buds.
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God was Charles a fast leaner. I would have screamed out in delight but my mouth was too full of cock, as I furiously cummed all over his face.
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My orgasm pushed Charles over the edges and suddenly my mouth was full of hot cum. As I vigorously gulped down his gooey cum, I found myself thinking that I was going to be awful sorry when Charles ‘graduated from this course.’
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Then with a smile, I though that perhaps after he’d learned the basics; he’d like to stick around for some ‘post graduate work.’
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The end… or is it?
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