Sex Education from Mom Ch. 01

SUMMARY: This story is about a mom who home schools her son. When she discovers her eighteen-year-old son trying (unsuccessfully) to put on a condom, she decides it's time for some good old fashioned sex education. At home. What she doesn't expect is just how overly sensitive her son is as she tries to help him.

All characters in this story are 18 or older.

DISCLAIMER: This story is a work of fiction. Any character resemblances to real life personae are strictly coincidental. Copying, re-posting, storing (whether digitally or in print form) or redistribution of this material is prohibited.

STORY:

[01]

My name is Megan and I've been a single mom since my son's father passed away six years ago. It was rough going for the two of us, especially since just the year before that, we had pulled our little boy out of school and started home schooling him. Fortunately for the two of us, I sold insurance from home. Not to say it wasn't difficult to juggle everything alone, but somehow I think I managed it pretty well, all things considered.

Justin has always been small for his age. Even at eighteen, he still reminded me of my little boy. Oh, he was intelligent and mentally grown up. It was just his appearance, really. He was just under five and a half feet tall and had shaggy, black hair that spilled down either side of his face and touched his shoulders. He got that from his dad. His face was young and innocent looking and he always had this look that made it seem like he was surprised about something. His eyes were a deep green—also from his father—and the skin surrounding his nose was sprinkled with freckles. He had a slim build and a flat stomach, although his arms had just begun to flesh out over the past year since he started doing some workout routines at home.

As for myself, I am forty years old although I've been told I don't look it. Over the past two years, I even started working on staying in shape, to keep myself looking as young as possible as long as I could. I'm a few inches taller than my son, although his pediatrician suggested that he's probably got a little more growing to do. I have hopes that he will eventually be taller than me, but that remains to be seen. My hair is a dirty blonde, and I recently took to getting it cut short, hanging just below my ears, except for my bangs which frame my face and reach a little past my shoulders. My eyes are blue and I typically like to accent them with dark blue eyeliner which has earned me countless compliments. Since I started working out, my figure has gone from slightly overweight to a slender, borderline athletic build, with an ample bosom. Despite getting my weight under a hundred and fifty, my breasts have never dropped below size 35C. I don't mind it, but I would be ok with them being just a touch smaller.

My son and I have a very strong bond. Partially because of what we went through together with the death of his father, but also partially because of how well our personalities seemed to mesh. He was a smart kid, and the conversations we sometimes had seemed to bely his age. I prided myself on how well I had managed to help give him an education even though, admittedly, home schooling did come with its drawbacks. The most prominent of them was the lack of social skills and inexperience with life in general. It wasn't that I tried to keep my son in the dark about things. But there was no way to avoid his lack of experience with certain aspects of life given the relatively cloistered childhood he had lived.

One of those "life experiences" had to do with the subject of sex. He had never had a girlfriend, which wasn't surprising since he didn't spend much time with kids his own age. I knew he masturbated, but that was a subject I was hesitant to bring up, for fear of embarrassing him. That may have been an unfortunate oversight on my part, in how I educated him. Sure, we covered the subject of sex education to a degree, but I was always worried to push his boundaries too far, so I held back. Well, he was eighteen now, and over the past few months I had started considering that there wouldn't be any harm in expanding his education in that area a little. But until just a couple days ago, I had yet to figure out how to breach the subject.

It was two nights ago when it happened. Thursday evening. Justin had been in his room for a couple hours working on homework, and I had been busy cleaning the downstairs. I was just on my way to the bathroom to take a shower and get ready for bed when I heard something as I walked by his bedroom. At first, I didn't even know what it was that I had heard, but it made me pause outside his door.

Leaning closer to listen, I didn't hear anything at first. It was very quiet. Then I heard what sounded like a rubber band snapping against something. Immediately after that, my son's unmistakable voice cried out softly, "Ow!"

Frowning, I stood there hesitating. Should I go in and see what had made him exclaim like that? A few seconds later, the same snapping sound drifted through his door, followed by a muffled noise that sounded like a groan. My frown deepened as I reached for his door handle. Turning it, I quietly pushed his door open and froze.

Justin was lying on his bed, completely naked. His back was propped up with a pile of pillows and he had his legs spread before himself. My eyes immediately flicked down, staring between his legs at what I mistakenly took for him masturbating. He had both hands surrounding his penis, which was quite hard and, admittedly, considerably bigger than I would have guessed given his petite body. But he wasn't masturbating, I soon discovered. Instead, I noticed that he had a little circular disc of rubber held with one hand, while the other was trying to tug it down and fit it over his cock. Oh my. My son was trying to put on a condom!

He hadn't noticed me standing in the door and his face showed a look of utter concentration. He even had his tongue clamped between his lips, staring between his legs. As I stood glued to my spot in the threshold of his doorway, I watched as he tried once more to pull the rubber sides of the condom down over his erection. He made it almost past the mushroom head before the stretchy material slipped out of his fingers and made a loud snapping sound against the side of his penis.

"Shit!" Justin cried out, wincing.

I gasped at the sight, which made him whip his head up, staring at me. Oh dear. My little darling. How adorable was this! His eyes opened wide and he opened his mouth to say something, but I forestalled him as I made a decision on the spot and immediately took two steps into his room. It was time for a little education for my young man.

Justin's eyes were full of protest as I approached his bed, but I had caught him off guard by making a b-line straight toward him. When I neared the side of his mattress, I found myself staring at his cock. It was even bigger than I thought. That thing had to be at least eight inches long!

"Mom?" he finally managed to say something.

Glancing briefly at his face, I smiled, trying to be disarming. Then I said softly, "Here, let me show you how to do that, sweetie." Without pausing, I lowered myself onto his bed, pulling my legs up and folding them under my butt.

Justin's face was turning a deep shade of crimson and he repeated in a strangled voice, "Mom?" Then he reached down and started pulling his blanket toward his lap.

Swatting at his hand, I shoved the blanket away, keeping his penis exposed. "Don't be silly," I chided. "I've seen you naked more times than I can count." Then I reached over him and grabbed the box of condoms that was lying on the bed. The box said they were "Standard" size, with a little logo underneath that read "Warming". Interesting. Frowning at my son's penis, I wondered if the "Standard" size was too small for him.

Justin seemed paralyzed and his eyes were still open wide as I pulled out another condom and tore the edge off the packaging. Upending it into my open palm, I closed my fingers around it. It was slimy in my hands. It had been many years since I had touched one of these things. Rolling it around to find the proper side to use, the lubricant smeared all over my skin. It started to tingle almost immediately and then I had the distinct sensation of my hand warming up. So that's what that little logo meant on the box. It had some kind of chemical in it that heated up.

Finally, satisfied that I had the correct orientation, I focused my attention on my son's cock. My, it certainly was a big one! Bigger than his father's by at least two inches, and wider, too. At the base of it, his balls were lying in a soft looking mass of pubic hair. I was certain he didn't trim it, but his hair was relatively short and tidy compared to the wiry bush I remembered from his dad.

With a slight shake of my head to clear my reverie, I reached my hand out toward my son's cock. "You start up here, like this," I said quietly as I gently pressed the circle around the tip of his penis. He flinched from the touch but didn't say anything. When I glanced at his face, I saw him staring at what I was doing, completely frozen.

I realized suddenly that this was the first time I had touched my son's penis since he was very little. Of course back then, it had nothing to do with sex. It was just from giving him baths. Blinking, I continued with my demonstration. With one hand, I held the condom centered on the tip of his penis. Then I placed a finger on either side of it with my other hand. "The rubber is rolled up here," I said, indicating the thick circle surrounding the thin membrane in the center. "You use two fingers, like this, and just push down on both sides at once to let it unroll on its way down," I continued. Then, as gently as I could, I started to roll the condom down his shaft.

My eyes were glued to my handiwork, watching as the rubbery material slowly covered his penis. Once I was past the head, over the bumpy ridge that connected the rest of his shaft, I let go of the top of the condom. There was a small sac of excess rubber at the tip for catching his sperm.

Slowly, using two fingers, I continued to roll the condom open toward the bottom of his shaft. My fingers felt quite warm but I wasn't sure if that was from the chemical in the lubricant or the heat from my son's cock. Probably a combination of the two. I made it about an inch past the head when his legs suddenly jerked a little. That was the only indication at first that something was wrong.

Just then, my son let out the softest, quietest little noise I had ever heard. It was almost a moan but turned into a sigh. Staring at my handiwork, I felt my son's cock give a ticking little pulse. Then I watched in surprise as a little squirt of white fluid suddenly flooded the flappy tip of the condom. Then another. And another after that. I realized my son was breathing heavily through his nose as I watched the tip of the condom grow like a tiny balloon, filling with his cum. He was shaking slightly, but his muscles were still rigid.

Finally, he seemed to be done so I slowly raised my eyes to his face. He was staring at me, wide-eyed. I felt my own cheeks growing red to match his. "I'm so sorry, sweetie," I whispered. "I... I didn't mean to make that happen."

Justin swallowed, shaking his head at me. Meanwhile his face grew an even brighter shade of red, like a tomato. "I tried not to," he said, sounding horrified.

Shaking my head, I tipped it sideways as I stared at his face. Then I said softly, "Oh no dear, it's ok. It's normal. It truly is."

He nodded at me, dumbly. I decided it was probably best if I left at that point so I didn't embarrass him any further. Sliding to the edge of his bed, I launched myself off. On the way to the door, I grabbed a towel he had thrown on the floor and tossed it toward him. "You can use that to clean up, sweetie."

Then I left his room, pulling the door shut behind me.

[02]

As I said, the incident with the condom was two days ago. But that night after I went to my own room, I could not stop thinking about what had happened. And for the next two days, I couldn't help but feel bad for what I had done. Well, for what had happened as a result of what I had done. I had truly just been trying to be helpful. And I hadn't even gotten a chance to finish showing him how to get the condom on all the way. That was an important step. Condoms lost their effectiveness if they weren't rolled on the right way. Plus there was still a little trick at the end to keep it from pulling on his pubic hairs.

And so, after some internal discussion, I convinced myself to go and try to show him again. I knew it would take a little coaxing on my part, but I was fairly confident he would let me do it. Secretly, the idea of doing it again gave me a thrill that I never would have suspected of myself.

Walking down to my son's room, I gently knocked on the door. When he called that I could come in, I opened it and stepped inside. A brief wave of disappointment washed over me when I saw that he was just playing a video game and was wearing his pajamas. But I quickly pushed that idea away. What was the matter with me? This was a purely educational experience.

"Hi sweetie," I said as I sat on the foot of his bed. He was sitting on his bean bag on the floor, controller in his hand as he shot some creature with a shotgun.

"Uh, hi," Justin said, sounding hesitant.

Waiting patiently, I sat in silence while he played his game. A few minutes later, his character died and he finally set down the controller, turning toward me. "What's up?" he asked. I noticed his cheeks were slightly flush, which confirmed that he was probably thinking about the same thing I was. The "incident", I'll call it.

"I wanted to talk to you about the other day," I said, getting straight to the point.

"Ohh k," he said, shifting uncomfortably on the beanbag.

Shaking my head at him and smiling to try to take away the sting of embarrassment, I spoke softly, "I didn't mean for that to happen. I just thought it might be helpful if I showed you the proper way to put a condom on."

His eyes widened slightly and he looked away, staring at the floor in front of my dangling feet. I decided to probe a little, so I asked, "What made you want to try wearing a condom in the first place?" His cheeks turned redder as I stared at him and he still wasn't meeting my eyes, so I added in a quiet voice, "Is there a girl you're interested in?"

Justin immediately started shaking his head and finally answered, "No, I j-ju-just wanted t-to see. I mean, I w-wanted to—" he cut off when he started coughing.

Smiling at him I leaned forward and ran my fingers through his hair. I always used to do that to comfort him. Then I said gently, "You just wanted to see what it was like to wear one?"

He nodded up at me, looking grateful. His cheeks were turning darker red as he sat there.

"Well that's pretty normal for a teenage boy, to be honest," I said. Pulling my chest back a little, I breathed in deeply and then patted the bed beside myself. "Come up here, Justin," I invited him.

My son only hesitated briefly before standing and walking to the bed. He had his hips angled away from me, which made me frown. When he sat down, he immediately draped his arm across his lap. I frowned at the gesture but decided not to push it just yet. Once he was settled, I reached a hand out and placed it on his knee. He flinched at my touch but didn't pull away.

"Did you try to put one on yourself since that night?" I asked, curious.

Justin shook his head and whispered, "No."

"Ok," I responded. Then after a brief pause, I reached up to his face, cupping his chin with my fingers. Gently, I aimed his head toward mine so he was looking at me. Then I said, "I want to try again. To show you, I mean."

For the next fifteen heartbeats, my son didn't say a word. His eyes seemed to be peering inside of me as he considered my offer. As we sat on his bed, I couldn't help but start to feel a wave of warmth inside my body. I knew what it was, but I tried to deny it. Nothing about this scenario should be having an arousing effect on me. But I held my ground and continued holding my son's head, until he finally gave the slightest of nods. I couldn't stop the grin that sprung up on my face at his agreement.

Letting go of his face, I glanced toward his pillows. His gaze followed mine and when we both looked back at each other, I saw that his cheeks were still hot and red. Raising my eyebrows, I nodded toward them to indicate he should move into the same position from last time. He swallowed a lump in his throat and then put his hands on the bed and started pulling himself toward the head of his bed.

My eyes dropped down to his crotch and I almost gasped at what I saw. My suspicions were instantly confirmed. My son was sporting a huge boner! His pajama pants were tented up several inches in the air. So, he really had been hiding that from my view. Had he been hard like that even before I came in, or was it the conversation that had elicited the response? I squirmed a little as sensation flooded my pussy, tingly and warm. I ignored it. This was purely educational, I scolded my internal self.

Once Justin was in position, I asked him where the condoms were. He pointed toward his nightstand, so I hopped off the bed and walked over to it. Opening the drawer, I reached inside the box of condoms and pulled one out. There were only a few left in the box, which means he must have tried to put one on several times before I had intervened the other day. A quick count showed me four remaining, not including the one I held in my hand. That meant four more potential chances for me to show my son how to put one on. The idea sent yet another surge of tingles up inside my vagina. I had to suppress a shudder.

A shuffling sound pulled my attention to my son once more and I watched as he shimmied out of his pajama bottoms. His raging boner sprang into view and I blinked at the size of it, still a surprise to me. Swallowing, I climbed into bed beside him, sitting on my legs just like last time. Tearing open the condom package, I turned it over and let the gooey circle drop into the palm of my hand once more.

"Ready?" I asked, barely above a whisper.

Justin nodded, seeming less hesitant than before.

Leaning forward a little, I took hold of the condom between my thumb and forefinger and then, for the second time in my life, I placed the ring of rubber against the tip of my son's rigid cock. My body shivered slightly, but I was sure he hadn't noticed. His attention was riveted on my hand and his penis. I reached my other hand out and noticed it was shaking a little. Steeling myself against the onslaught of unprovoked arousal that started to swarm within me, I placed my fingers on either side of the ring once more.

Drawing in a deep breath and holding it, I could hear my heart pounding in my chest. Then I gently pressed downward with both fingers at once. Both of them promptly slipped past the edge of the rolled up ring, sliding partway down the mushroom head of my son's penis. He sucked in a sharp breath and I saw his leg muscles tense. Recovering quickly, I lifted my fingers back up to the ring and pressed inward a little as I started trying to roll the rubber down.

My fingers slid over the slippery edge once more and ran halfway down his bare shaft before I caught myself. Shit. What the hell, Megan? Then it dawned on me that I had the condom on upside down. My own cheeks felt hot and I knew they must be as red as my son's. But I spoke, trying to play it off as if I had done it on purpose. Gently lifting the condom away from the tip of his penis, I flipped it over as I spoke, "See, there's only one way for these to go on. When you have it upside down like I just did, it won't unroll."