The First Time

"Hey Mom," I said to my mother just before I got inside her car, each word feeling like a razor blade cutting through my throat as I said it out.

I knew she loved me, and I loved her, too, but I wasn't really her biggest fan those days. Giving her the silent treatment was something I would've preferred, but it was only going to break her heart more, and since the pain caused by her recent heartbreak was too much already, I didn't want to add on to that.

"Hey baby," she replied and I gave her a chilling stare which saved me a few words to remind her that I wasn't a fan of cuddly words, too, those days, especially at school. "Hey Charles," she tried again, planting a kiss on my cheek as soon as I settled on the shotgun, and even in moments she was genuinely trying to show some affection and be happy, I could still tell how desperate she was to get over Kenny, her last boyfriend. Running away from him was the reason we'd moved to a new town—to start over—and she had to tag me along with her, ruining my life in the process. "How was your day in school?" she asked, gunning the engine, and on second thought, I figured I didn't want to talk to her—starting with answering that question.

Instead, I decided to have a quiet and peaceful drive home as I counted all the things our move to a new town ruined in my life. I didn't have a car anymore, and that was the reason she'd come to pick me up at my new school, making me feel like I was some thirteen-year-old dweeb—a dimwit.

Starting off at a new school, ten weeks before the end of high school, was in itself social suicide because there was really no point in making real new friends when high school was almost over, and thinking about how my mother took away my real friends and my prom date when we moved, made me want to hate her. That wasn't the last of it, and even though I was likely going to get over not having real friends and a prom date as soon as high school was over, I was almost certain that for a long time, I wasn't going to forgive how she ruined my chance to get laid for the first time.

It took me two years of dry humping to get my girlfriend, Keisha, to agree that prom night was the night, and with me moving eighteen hours away, that wasn't going to happen anymore, and anyone put in my shoes would've understood my frustration. But Mom wasn't like that. She always assumed that I could roll with the punches.

"How was your day in school?" she asked me again, and flinching away to try and show her how much I thought that question was more of a burden to answer didn't help. She kept waiting for the response.

"It's still the same...I'm still trying to settle down," I eventually replied her question after a while, and yes, I was still trying to settle down and probably find myself a hot chick.

My dick missed getting sucked and fucking tits. Those were things Keisha used to let me enjoy, but those days I was just surviving on video calling to watch her jill off in front of the camera. Sometimes we masturbated together, and she wanted us to continue doing that until the day I was going to go back for her to get the fuck she promised. But with my mom still calling the shots, that day could only come after I finished high school because it was the only time I was going to have the freedom to travel back to Keisha, and as much as I looked forward to that day, I just couldn't wait that long if there was a chance that I could find someone to fuck before finishing high school.

My life was also in my new home town now, so even though Keisha and I were going to fuck after we finished high school, our relationship wasn't going to survive the distance, even with the frequent video calls to jerk off staring at each other. She was the type that could manage to have that kind of relationship, though, but I couldn't sentence myself to that kind of life, and to be honest, the way we were keeping the flame burning wasn't really cutting it for me. I needed the real thing. But just because I still had to find Keisha's replacement, surviving on the video calls and fantasies of her cupping my balls and sucking on my dick was all I had at the time, and on a daily basis, I was beating my meat multiple times.

That was also another reason I had to find Keisha's replacement because my hand couldn't give me the type of orgasms I got from her blowjobs, or when I fucked her boobs. Even with that aside, masturbating multiple times a day didn't seem healthy to me. I had to have the real thing. Real fast, too, because the lack of gratifying orgasms was getting me hornier by the day, and my need to have those types of orgasms was about to go through the roof.

"Did you make any new friends today?" Mom went again with a burdening question and I felt it when she glanced to check the distracted look on my face.

"Just a few," I replied and looked out of the window again, wondering why she wasn't getting that I wasn't in the mood to talk.

Whenever she felt like that, she always demanded that I stopped pestering her until she was fine, but she wasn't doing the same for me, and that was being unfair. I felt like lashing out suddenly, and let her know that it wasn't right that she wanted me to remain nice to her when she had failed to understand me when I begged her to stall moving until I finished high school. But my thoughts were suddenly distracted by considering the possibility that if I were to get a girl who was a virgin again, she probably was going to make me spend time fucking thighs, or the top of a panty-clad pussy like Keisha made me do. Heaven knew I wasn't cut out for that again, and I quickly stopped thinking about it before I began feeling hopeless about managing to beat my target to get laid before I finished high school.

"I bought some flowers and we're going to be doing some planting in front of the house this afternoon," another attempt to make conversation came from Mom and I glanced at her. Her face was beaming and she was gleefully smiling.

She really adored our new two-bedroomed house she had got for a bargain. It wasn't that bad, but it needed major touch-ups, especially the leaking roof and the water-stained ceilings. After thinking about what she'd just said again, I smiled, too. I was three orgasms behind schedule that day because in the morning I left for school without jerking off, and all day during school, I thought about how I was going to get to it the moment I was going to get home. That was the reason I smiled at the news that we were going to do some yard work that afternoon because staying outside to get some work done was going to keep Mom out of my way each time I was going to jerk off, and for me, the work was going to provide intervals between my wanking sessions.

"Great," I said in response to her and she mumbled something else I didn't catch. That made me glance at her because I thought she was talking to me.

She wasn't, and just after I realised that, my eyes were caught by her exposed bronze legs. The knee-length skirt she was wearing had ridden up to a few inches below her crotch as she drove, and too little was left for imagination. I tried to look away, but I couldn't. I felt it too compelling to stare at her smooth and well-toned thighs, and during the moment that I did that, my dick twitched, preparing to start getting hard, but before that happened, I somehow managed to look away, and after that I laughed at the way my dick had reacted to what I'd just seen.

These hormones are getting out of hand, I thought that, too.

My friends always said that my mom was hot, and even though she kept her body in shape by working out a lot, I didn't look at her in that way. She was my mother and the last woman that I expected to turn me on in the world. So I dismissed what had just happened as a one-timer, but I ended up glancing at her thighs every ten seconds until we got home. As I got out of the car, I looked at the front of my pants and I saw that I had a noticeable erection. Looking at my mother's thighs had made me hard. That was another first for me, and as I went to my room, I tried to wait for the erection to go away on its own because even though I had plans to jerk off a lot that afternoon, I couldn't stroke the boner my mother caused.

It felt wrong, really wrong, but that stopped counting when the boner failed to relent, and I eventually gave up and realised that my right hand and a bottle of lotion were the only things that were going to get rid of that disgusting boner. I called it a disgusting boner because I got it from watching my mom's leg, but utterly revolting doesn't start to describe what happened next. The image of the thigh that gave me the boner I was stroking was all I could fantasise about, and midway through my wank, I visualised Mom coming into my room.

"Hey baby," she said, slowly walking in, her body covered by a slinky nightgown which made it obvious that she was wearing nothing underneath.

I paid closer attention, and watching the curves of her boobs clearly outlined on the front and her erect nipples poking on the fabric of the nightgown made me stroke my cock faster. And her thighs, they were bare right up to an inch of her crotch, and imagining the pussy my eyes were going to see if she were to raise up the bottom of the nightgown a little doubled up the sensation I was getting from stroking myself.

"Care if I join?" she asked as she kept approaching and my eyes kept stuck on her crotch, hoping a wrong step was going to make the nightgown ride a crucial inch up her thigh to make me see her cunt. As if fate needed all my wishes to come true, that wrong step happened right after I wished for it.

Though it was a quick flash which lasted less than a second, I saw it. I saw her slit, separating two symmetrical puffy lips of cunt which rubbed against each other on the next step she took, showing me a flicker of her pink inner flesh for a split-second before that sight was stolen from my eyes again by the nightgown which dropped back down to cover her crotch. But in my mind, the image was permanently carved, and for a long time, I was going to keep replaying it.

"No, I don't mind," I replied her proposal to join me, with my throat dry, and my left foot already making the first step towards her because I wanted to take off her nightgown and fuck.

"No fucking, I'll just get naked like you are, and then I'll lie on the bed to show you my wet pussy... and then we'll jerk off together," she quickly stopped me and I reluctantly did that then I continued stroking myself when she began taking off her nightgown. Slowly and enticingly, she let it fall off her body and with each inch of her smooth skin that got exposed, my arousal increased and I started preparing for an orgasm.

"Oh God," I groaned when the nightgown slid to her belly, exposing her plump and round boobs adorned by round and dark, pimply areolas with the longest nipples I'd ever seen in my life standing stiff in the middle. "Oh God," I groaned again when the nightgown slid below her waist, making me see her beautiful smooth-shaved cunt for the second time, and the way her engorged clit was poking out at the top got my heart racing so fast my blood heated, and suddenly my veins were on fire.

Each and every nerve in my body felt that sensation, and as I watched her walk over to lie on her back on my bed, the feeling kept intensifying. Lying spread-eagled first, she snaked down her right hand towards her wet slit while the left hand was making her moan with the way she was fondling her tits. When the right hand made it to her slit, she ran three fingers up and down it a few times before fucking the middle finger inside of her.

"Mm Charles," she moaned, her eyes closed and her middle finger starting to smoothly slide in and out of her juicy sex while wet noises coming from there were getting louder with each finger prod she sent inside of her. "Come kneel between my legs and continue stroking your cock, baby. I want to watch you stroke your monster cock while I fuck my pussy—come," she desperately called, and as I went to kneel between her legs, she raised her knees up into the birthing position.

After I settled in the middle of her parted thighs, my eyes kept watching her fingers pushing in and out of her wet pussy while I began stroking my cock really fast, my right hand only a blurry sight before my eyes. She soon began moaning wilder, and as she kept picking up the speed to her already quick and furious jabs, I became too distracted to continue stroking my cock because watching her pleasure herself like that was amazing.

"Oh yeah, baby, oh! Keep stroking your cock for me. Come on," she prompted as she reached for my left hand and when she got it, she put it on her right boob. "Yeah, touch it. Feel my tits, baby. Come on, feel my tits and stroke your cock, baby," she desperately moaned and I began doing what she requested.

After a few minutes, tension in my balls started building up quickly and I knew that in a few moments I was going to come, without fail that time, so I decided to change what was happening in the fantasy I was playing in my head to build up to a better orgasm, and suddenly my mom reached for my neck and pulled me down to lie on top of her. "I need to have you now. Put your cock into me. Fuck me, Charles?" she breathlessly begged and I hurriedly slid into her wet cunt and began hammering away at her.

It didn't take long before the tension in my balls finally gave way to the most violent orgasm I'd ever had in my life. I came like I'd never done before, and I felt a significant amount of energy leaving my body as I shot out long strings of sperm on a tissue, and once I was done having that orgasm, it was back to reality again.

Everything slowly started to sink in and go in place. I'd just used my mother in a fantasy, and imagining the two of us fucking gave me the most amazing orgasm I'd ever experienced in my life. That quickly became wrong when the morals she taught me took over, but to make the guilt of the sordid things I'd just done less, I dismissed fantasising about her as another one-timer, just like how I'd gotten aroused by staring at her exposed thighs during the ride back home.

But in reality, what had just happened was the first sure sign that the way I was looking at my mother had changed, and even though I promised myself that it was the first and last time that I was ever going to fantasise about us fucking, it was only a matter of time before I realised the truth. Before that time for me to realise the truth came, I got out of my room and went to have a late lunch. Then I went outside to make flower beds after finishing my meal. A few minutes later, Mom came out to plant the flowers and I was almost done making the flowerbed. She was wearing old three-quarter pants and an equally worn-out shirt. Nothing about those clothes was boner-causing, and the effect she had on me seemed normal again.

"Oh," she sighed, dejectedly dropping her shoulders and slapping her palms on her thighs. "I forgot to take out the flowers from the car."

"Let me get them for you," I said as I dropped down the rake I was holding then I dashed to the car to get the flowers and she was down on all fours when I came back.

All her attention was on the holes she was busy digging to plant the flowers in, and I realised that because her shirt had gone up her back and she didn't pull it down. Her pants had also moved down a little, leaving strands of her G-string and a few inches of her butt crack exposed.

What I felt earlier about her clothes not having any arousing effect on me instantly changed the second I noticed her G-string and butt crack exposed like that. When a sudden gust of wind blew past us, she quickly covered herself when she felt it on her exposed back. It was obvious from her reaction that she did that to keep me from noticing what her clothes left uncovered. But that reaction was a little too late because I already had a boner.

If that incident had happened on a day I wasn't insanely horny, I could've managed to wilt the boner and continue the yard work, but since that wasn't going to happen, and since I wanted to avoid getting seen with my boner, I suddenly dropped the flowers by her side and rushed inside the house to masturbate. The bathroom seemed more suitable for the furious quick wank I wanted to have, and the moment I dropped my pants to my thighs and gripped my pulsating cock, she was on my mind again. That time she just appeared naked and ready to start the action, unlike the last time when I visualised her teasing me with a strip and mutual masturbation.

"Come fuck that monster cock into me, honey," she purred, her left hand fiddling with both her nipples at intervals, and her right hand on her pussy, showing me what I was supposed to go for.

Without wasting time I went for her, and everything about the way I approached her and sunk my cock into her hot and tight pussy was urgent. The fuck I fantasised us having after I stroked my dick inside of her was feral, and so were her moans and screams as I imagined her grappling me all over as she tried to steady herself and avoid losing her footing.

"Yes, honey...Oh. Charles, you're stretching my cunt," I imagined her moaning that to me right before I held her neck with my right hand really tight, almost choking her, and soon after that, the fantasy was over as I had another thunderous orgasm.

Just like the time I masturbated in my bedroom, I shot out my seed on a tissue, and after I was done, I flushed it down the toilet, then I went out of the bathroom feeling relieved from the quick and furious wank I'd just had. The moment I set my eyes on my mother again, I wanted to start feeling bad for using her in my fantasy for the second time that afternoon, but all I could think of was if I was really not going to fantasise about her the next time I was going to jerk off.

Morals and raging hormones aside, it had just become clear that the orgasms I got when I masturbated with her in my mind were always going to be earth-shattering. So even if I were to find my morals again, or manage to have my hormones back in control, I made a choice at that moment that I wasn't going to give up fantasising about her. It was going to be my own secret she didn't have to know because I knew once she found out all there was going to be for me was trouble, even violence, because she was just strict like that.

"Where did you go, I need you to help me out, honey? Let's make our home nice together," she mildly chided when she saw me and I picked up a bunch of flowers to plant before I replied her.

"Sorry," I apologised, and with that, all was forgiven and we finished the rest of the yard work without any interruption from my dick.

With the dirt we were touching around while we were planting the flowers, we both needed showers right after we finished, and showering was what we went to do in our respective bathrooms right after we got inside the house. I stayed in my room after I was done, and I only came out late in the night when I got called for dinner.

"Please grab the plates and water glasses on your way, sweetie?" she asked the moment I showed my face in the kitchen and I kept looking at her, my eyes stuck on the nearly transparent nightgown which she was wearing under a purple bathrobe.

That was her usual dress code at night, but everything was now looking different. The nightgown looked provocative and my blood almost instantly began racing faster. The fact that she wasn't tying the sashes of her bathrobe added fuel to the situation because she didn't wear a bra at night. I could see her dark nipples poking on the front of the thinned nightdress. With my dick already hard in an instant, I realised I needed to keep seeing her nipples during dinner. So I sat opposite to her on the dining table and whenever she bent forward to reach for something, I caught a glimpse of her meaty tits dangling freely inside of her nightgown.