The First Time

Seeing her tits dangling like that kept happening a lot, and at one point I sensed that she noticed I wasn't being my normal self, but checking her out was the last thing she expected me to do, so I didn't stop, and my dick stayed hard. Midway through dinner, I started thinking of stroking the boner I had right there at the table to see if jerking off while looking at her was going to make me cum like I did when I fantasised about her. It was too risky, I knew it, but within a few moments, I stealthily slid my right hand under the table and undid the button on my pants. Then I slowly pulled down the zipper, making sure it didn't make a loud zipping noise.

"Why aren't you eating?" she asked because my right hand was still under the table, opening my pants. I quickly brought it up and lifted the fork without answering her question. A moment later she stretched her hand to grab a bowl and her right boob and its nipple, which was poking on the thinned nightgown, got exposed again.

My dick flexed, and instead of the right hand I always masturbated with, I put my left hand to work. It was the weaker hand, but it was going to work just fine because I wasn't planning on stroking myself as fast as I did when I jerked off in private. As I enjoyed my slow and sensual strokes, my eyes kept stuck on Mom's chest, catching every glimpse of her boobs each time her hand movements made the robe move to the side, exposing her big, round breasts.

After a few minutes, I got lucky when she made a slight move to the left and her robe permanently moved to the side. I began seeing her left boob with more detail and without it getting covered constantly. That made my cock even harder and I started stroking it faster, cleverly stealing glances at the tit, but I mostly concentrated on the area around her exposed nipple.

My aim had suddenly changed to making myself orgasm before she made another slight shift that was going to block the arousing sight I was seeing. That happened, and the moment my sperm started tunnelling up my shaft, I flicked a napkin from the table onto my lap, making sure that it looked random. Just after that, I started coming on the napkin and Mom noticed my face frowning.

She asked, "The food tastes a little burnt, right?" I just let out a low unintelligible sound which was more of a groan as I wiped off the tip of my cock and crumpled the napkin into my pocket, but she took it as a yes. "I'm sorry, you can have mine, its tasting fine," she said, trying to push her plate towards me.

"No! It's fine. I'm almost full, anyway," I quickly stopped her.

She shrugged and shook her head, baffled, and I didn't worry myself with that because I knew she had no idea what had just happened. Dinner went on quietly from there, and when I got done, I buttoned my pants before I got up from the table. She and I did the dishes together, and every time she had her eyes away from me, I checked her out. The hot woman my friends always said they saw in her started appearing right before my eyes, and after stealing glances at her ass a couple times, I realised that even before that day, I always thought that she had the most beautiful round and tight ass I'd ever seen on a mature woman.

Admitting that was just the issue, and as I looked at her other features, trying to remember what I thought about them all along, I noticed that her full breasts were almost Ds. That was the first time in my life that I'd ever estimated a bra size on them. They were just really big tits on my mom before that day, and as I kept switching my eyes between her round ass which made a nice curve away from her body, and the hot thighs on which the curve of her ass ended, my dick got hard again.

When I added the boobs to that list, I got harder, and until we finished the dishes, I had my crotch pushed against the sink, hiding my erection. I waited for her to leave the sink first, and right after she did, I went to bed, planning to have one more wank before falling asleep, but everything just became hazy the moment I put my head on the pillow. Quickly after that, I saw nothing else, and the next thing I knew, it was morning, and I woke up with a boner which needed my attention. The moment I familiarised myself to my surroundings, I started doing that, and the plan was to beat the meat at least three times before I got out of bed.

It was a weekend. So I wasn't in a hurry to get to school on time, and Mom wasn't going to bother me because she always let me sleep in all Saturday mornings. She was a morning person, though, and when I heard her busying herself around the house, probably finishing unpacking some of our stuff, it became impossible to fantasise about anything but her when I started stroking myself.

That morning's fantasy was of her giving me a blowjob, and it was actually a memory of the most amazing blowjob I ever got from Keisha, but with my mom in it, and not my girlfriend. It happened a week before we left our old home and I was coming out of my bathroom, wearing a towel around my waist and nothing else on the rest of my body.

"Hey babe," she said, standing up from my bed to approach me, and we kissed when she got to me. "I'm feeling naughty today. How about I give you a blowjob?"

"O-Okay," I stammered the reply, and as she lowered herself down on her knees, my dick quickly stiffened and stretched out the towel.

Once she took off my towel, I held her head and kept my hands there as she slowly swallowed me the first time. Her head then started rocking back and forth in time with the way I was stroking myself, and with my mom as the one giving me head in the fantasy, the feeling was heightened. Before I could stroke myself to the first orgasm, she came to knock on my bedroom door. I ignored her for a while since she couldn't enter and find me awake with a stiff cock in my palm because my door was locked. But her incessant knocking started threatening to ruin the mood, and I ended up deciding to talk to her while I continued jerking off.

"I'm going to the grocery store, should I get you something?"

"No!" I quickly shot back the answer without thinking if there was anything I needed from the grocery store.

"Okay then. I'll be back just now," she said and then I heard her walking out of the house.

A few moments later the car engine started, and right after that, she was gone. I wanted to continue with the fantasy I was having before she knocked on my door, but suddenly, I thought of her panties, and it seemed they were a better turn on than the fantasy.

I'm really losing control of this thing, I thought to myself as I got out of my bed, my cock still hard, and when I got to her bedroom, I plundered her panty drawer.

She had different types of underwear in there with different colours and designs. The best of them all were a pair of white silk French knickers, and the moment I began rubbing them on my cock, I decided to take off all my clothes and make the experience more sensual. While I did that, I started picking the panties I'd left in the drawer one by one, smelling the sweet scent of her pussy on the crotch of each panty I brought to my face.

I had no intentions of spilling my sperm on any of them, though, but all off a sudden, I felt tension in my body growing. Before I could react to that, I climaxed and spilled all the sperm that came out of my balls on her silk French knickers. A moment of clarity hit me thereafter. I'd just emptied my balls on my mom's underwear.

It sounded wrong, and within a moment, it felt wrong, and after another moment, I started feeling bad for what I'd just done. All the excitement I was feeling about jerking off more than once that morning went away because of the guilty feeling I started having once I had my orgasm. As I kept holding the knickers that had quickly absorbed my jizz, I began wondering what I was going to do with them.

I couldn't throw them back into her drawer with the rest of her underwear, so I decided that I was going to wash them and put them back before she noticed. With the guilt I was still feeling, I also decided that I was never going to ransack her panty drawer again and use her underwear to pleasure myself. But all those melodramatic decisions I was making turned out to be just the same as all the momentary miserable episodes I usually experienced in the aftermath of a really good orgasm. Because after I went out of her bedroom and stuffed the panties under my pillow with plans to wash them later, I ended up forgetting about them.

I only remembered of their existence when I accidentally put my hand under my pillow the next morning, and because the melancholic feelings of the previous morning were long gone, I used them to rub myself to an orgasm again. Unlike what happened the first time I used them for that purpose, I didn't feel bad about it after I had my orgasm, and instead of washing them like I originally planned when I put them under my pillow the previous day, I decided to keep them for use at any time I was going to please.

"Honey, breakfast," Mom called from the kitchen just as I finished masturbating for the second time.

My dick didn't seem like it was going to be ready to be stroked again in a couple of minutes. So I got up and went for breakfast, hoping that Mom was still in her nightgown because that was obviously going to turn me on and give me something to visualise the next time I was going to jerk off.

"Morning Mom," I said when I got in the kitchen, and to my disappointment, she was already in her day clothes and they weren't showing skin except for her neck, face, and hands.

"Hey you," she cutely said back, kissing my left cheek and she was already getting up from the breakfast table because she was done eating. "You should finish unpacking your stuff this morning, after you finish your breakfast. Your room is looking like a junkyard," she ordered and I had no plans of unpacking in a few weeks.

"I'll do it next weekend, Mom," I said and she was already walking down the hallway, going to her bedroom or somewhere else. I didn't care. The food was where all my attention was at, so I continued having my breakfast, and the next thing I saw in front of me was her pair of silk French knickers, still wet with my cum. That instantly changed a good moment I was having with my food into one of the most awful moments I'd ever experienced in my life. As I slowly dropped my spoon into the cereal bowl, I also lifted my head slowly, like someone was pointing a gun to my head.

"What's the meaning of this, Charles?" she asked with her angry voice and there was no doubt I was in huge trouble, not to mention the embarrassment I felt. Not all hope was lost, though. I knew I was able to defend myself for masturbating, but I wondered how I was going to explain using her panties as a masturbatory aid.

"Umm," I muttered, trying to find a better way to explain myself, but there was really no better way to say it.

"It's one thing that you do your things on your sheets and I have to wash them. But this," she yelled as she put the panties in my face, and realising that she knew I masturbated all along added to the embarrassment, instead of making it better, since she already knew and was probably fine with it. For a few minutes which seemed like hours, she continued telling me off, and the increasing shame that I felt eventually made me tuck my head down. "Do you know that masturbation can make you go blind!" she screamed at one point and I wanted to howl my lungs out when my ears heard that.

I managed to get a hold of myself before the laugh came out, but I couldn't avoid smirking a little. When she noticed the smirk on my face, she got infuriated some more. Because of that, her speech, which was almost close to an end, got extended by half an hour, and when she finally shut up, the most agonising lecture she'd ever given me before that morning got bumped down to the fifth position.

Nothing was worth occupying the second, third, or fourth position, and as she kept looking at me, probably waiting for me to cough up an apology, I was praying for the floor to open up and swallow me. She'd never shamed me like that in my life, and for the entire week that followed, I didn't masturbate, or even think of doing it.

I spent that whole week avoiding being in the same place with her, too, because knowing her character too well, it was obvious anything I was going to do to piss her off was going to make her start lecturing me all over again. That wasn't supposed to happen again by all means, and to increase my chances of avoiding setting her off, I made friends with a guy named Derek the first thing Monday morning.

He lived close to our house and his car became my ride to school and back home starting from that day. When Friday came, I knew I had to find something to keep me away from my mom during the weekend. A few ideas came, and for Friday night, there was a band Derek, and his girlfriend, Chelsea, were excited about. Most people thought the band sucked and they weren't going, but just to avoid being stuck in the same place with my mom, I joined Derek and his girlfriend, sacrificing myself to the most boring experience I was ever going to get watching a band.

"I'm going to sleep over at Derek's tonight, don't leave the front door unlocked for me," I said to my mom before I went out.

"Okay, seeya in the morning," she replied from the kitchen and the next second I was out of the door.

I found Derek at the mall, and after watching the band for thirty minutes we all agreed they sucked. We left and spent half the night going from one party to another. His girlfriend had a curfew, and after dropping her off at midnight, Derek and I continued the partying until three in the morning. He was too drunk to drive back home after the partying, and he wouldn't let me drive us there because he thought we were equally drunk. We ended up agreeing to sleep in his car. I tried, but his car seats felt too uncomfortable to sleep on, and for an hour while he was already snoring, I couldn't manage to fall to sleep.

It was almost dawn and safe for me to catch a bus home to sleep in a comfy bed. I left, and when I got home, it was still too early to wake my mom up. I decided to sneak in through my bedroom window, and as I took off my shoes, ready to throw myself on the bed, I heard something like a moan.

I was tired like hell, but that sound gave me strength to freeze where I was and listen more carefully. A moment didn't pass before I heard another moan, and that time it was louder. I couldn't doubt that it sounded like a woman getting laid, and although Mom was a woman who lived in the same house with me, my first suspicion was that she was watching a porn movie because I knew very well that she wasn't seeing anyone. But after realising how ridiculous it was to think that she was watching a porn movie at that time in the morning, I thought maybe she was seeing someone but didn't tell me like she always did.

When everything was fine between us, we were close like that, but with the way I spent the entire week avoiding her, there was no time she could've had a chance to tell me anything like that. But I knew once we were over my little indiscretion, she was definitely going to tell me about the new guy. At the moment, that didn't matter much, though, because my dick was already getting hard, and my mind was pushing up a crazy idea to go and confirm if someone was really shagging my mom.

I'd never done that before, although in the past she brought a few of her boyfriends over for a fuck when I was around. With everything I did the previous week, spying on her while she was getting nailed seemed to be okay. So with my dick still getting hard, and my heart racing faster with the wicked thrill of anticipating to get to my mom's door and stroke my erect cock while I fantasised myself as the man fucking her, I tiptoed out of my open bedroom door, making sure that I didn't make a sudden loud noise.

When I made it out of my bedroom door, I saw light coming out of Mom's bedroom. Her bedroom door was wide open just like mine. Sleeping with her door open like that was something she sometimes did, so I wasn't surprised. I was actually thankful that she felt the habit to leave her door open at night was unnecessary to avoid on a night she was going to spend getting fucked by a guy in her bed. When I made the decision to confirm if she was really getting fucked, I just wanted to do that and imagine what was going on in there once I made the confirmation.

But seeing her bedroom door open brought up a chance of me watching live sex. There was no point in stroking my cock while I fantasised myself as the man fucking her anymore. A chance to watch her actually getting fucked was way better. With that thought in mind, I got to her door quicker, wanting to watch the action a little bit longer.

Her moans weren't getting any louder, but she was still moaning like someone getting fucked. When I took a first peek inside of her bedroom, there was no man fucking her. But she was lying spread-eagled on the bed—completely naked, with her legs towards the door, and a vibrator buzzing inside of her pussy.

I got paralysed, only my hard dick kept functioning as it stretched out the crotch of my jeans some more. My eyes kept working, too, because they stared. The last time I saw her naked was when I walked in on her while she was dressing and I was ten. It was only a glimpse, which lasted for a second, or two, because my morals didn't allow me to look any longer than that back then.

But of course, that was before I started seeing her through new eyes, and I liked the new eyes better, because I was able to stare at her naked body for as long as I wanted, and since there was no man fucking her, my plan changed back to stroking myself. Without the fantasy of me fucking her, though, because watching her jill off with her vibrator was better. But as much as I felt like fishing my dick out the fly of my jeans to start jerking off at that moment, I couldn't. The rest of my body was still paralysed with what I was seeing. So I stayed stuck and watched while she raised her knees up in the birthing position and started pushing the vibrator in and out of her wet pussy as it kept buzzing.

"Oh yes—ah," she moaned when her left hand squeezed her left tit, pinching the nipple between her thumb and forefinger sometimes. After a few moments, the left hand slowly went down towards her pussy, where her right hand was still pushing the vibrator in and out sometimes. When both hands were there together, she started rubbing her clit furiously with the left hand, and the right hand began thrusting the vibrator inside of her wet pussy faster while she furiously rubbed her engorged clit like that. "Oh my God... Oh my God... Oh my God," she moaned as both her beautifully pedicured feet got off of the mattress and went up in the air with all her toes curled really hard.

My girlfriend always did that with her toes whenever she told me that I was eating, or rubbing her pussy really good. So I had no doubt Mom was really enjoying herself. Soon, she began spreading the gap between her legs wider, and the moment her moans started getting wilder, she slowed down fucking the vibrator in and out of her wet pussy. Moments later, she completely stopped doing that and left it buzzing away with most of its length inside of her. I realised that she was about to come and my live show was soon going to be over.

If I were to walk in on her and catch her right at that moment, my past week's indiscretion wasn't going to matter anymore because the two of us were going to be even. I was probably going to emerge as the better person because masturbating naked like she was doing made her look double as horny as I got on my worst day. But as much as it was a good idea to walk in on her and make her know that I'd just found out she masturbated, too, I didn't know the best way to make an entrance and avoid getting the intrusion flipped over on me because she was cunning like that sometimes.