Chapter 1

My name is Adam, and I was very normal, I was a little taller for my age, but that’s just because I had my growth spurt earlier. However, I started masturbating late compared to most, I was over fourteen when I did. It wasn’t that I was against it, I honestly had just never heard of it. A friend made a joke about “jacking off” and I had to ask him what that was, he told me, and of course that night in bed I tried it, and like most teenage boys, I was hooked. At this point in my life I hadn’t done anything more than kiss a girl, so masturbating was a great hobby for me. Since I didn’t have a girlfriend, and no real prospects, I knew I wasn’t going to be getting any with a girl any time soon.

I was doing it multiple times a day, and had come up with a good routine. The morning was a must, because like all guys my age, I was plagued with ridiculous morning wood! I would try to do it in the shower in the morning when I was getting ready for school, the shower was great, but of course my parents would knock on the door and tell me to hurry up. Plus I had to share a bathroom with my younger sister, so I usually had to settle for a quick one in my room before I got dressed. I would then jerk off when I got home from school, my little sister got home about an hour later, so it was just mom downstairs doing housework and preparing dinner. When I’d go up to my room to start on homework I’d actually have a quick jerk first. The common theme was that I usually had to be quick and discreet. It was totally possible that my mom could walk in to ask me something while I was doing homework, or my sister could burst in to play or just bug me, or my dad might come up to say hi when he got home from work. So in my bed at night when everyone else was asleep was the only time and place I had privacy.

When I first started masturbating I used to lay, buck naked on the bed, with lotion and and towel. I’d take my time and enjoy working myself up to a really good orgasm. The towel was totally necessary for me. I’d heard jokes, and guys saying that they kept a box if tissue in their rooms, I asked why and they said it was to catch their cum shot to avoid a mess. I couldn’t fathom a tissue catching my load, I’d blow a hole right through it! I happened to cum a lot when I jerked off, and not just a lot, I also shot for distance! The first time I did it, I was laying in bed stroking my cock vigorously, and when I came I blew a load all over my own face and pillows! After that, if I was masturbating while laying down or sitting at my desk, I always put a towel over my cock when I was almost ready to cum. Or if I was standing, I’d lay the towel out in front of me and aim for it.

During this time my parents were going through a rough patch, and they often got into huge fights at night when they thought we couldn’t hear them. One night my mom came into my room, just moments after I had finished putting my dick away. She opened the door and asked if I was asleep, I said no and she came in. She apologized for the fighting, and asked if I had heard, I said I had, since my room was next to theirs. She said she had just checked on my sister, Lacy, who was asleep, which made sense cuz her room was clear across the house. My mom said she just wanted to catch up with her baby boy, but she was visibly upset, and I think she just wanted to vent about things going on with her and dad. She ended up falling asleep in my room.

This started to become a nightly routine, at least when they were having a fight. She would come into my room to chat, but really it was because she didn’t want to stay in the same room as him, and she didn’t want to wake up my sister, so she was crashing on my bed.

Nothing about this was sexual, She was a good looking woman, but not so good looking that I got aroused by looking at my own mother. She was usually wearing pyjama pants and a tee shirt or tank top, although sometimes she wore a nightgown, once again, nothing sexy. I did notice one night when she was asleep with her back to me, that her nightgown had come up and she was wearing a thong. This was surprising, even though I’d seen the tops of girls thongs at school, I had no idea that someone like my mother, who granted was only in her 30s, would be wearing something like that!

As her sleep overs continued for several weeks, I noticed that she became closer to me, at night she would cuddle a little, And ask me to put my arm around her, in the “spooning position”. This became a problem one night when I hadn’t been able to jerk off. She had me spooning her, while she was checking her phone and I was trying to fall asleep. Unexpectedly, the little movements of her ass against my crotch gave me an erection! I began moving back away from her, a little bit at a time so she wouldn’t notice.

“Why are you moving away? You know I like when you cuddle with me like that, it feels all cozy.” With that she backed up and her ass slammed right into my hard on, “oh! I’m sorry sweetie! I didn’t know!”

“Well what was I supposed to say?!” I snapped, clearly embarrassed.

She started to laugh a little bit “it’s ok, don’t be embarrassed, it’s not your fault and it’s completely natural.”

“I know it’s not my fault, it’s YOUR fault.” I couldn’t help but smile and start to laugh. We both had a good laugh about it actually, which relieved my embarrassment and distracted me enough to make my boner go away. We ended up falling asleep as usual.

This awkward encounter actually brought us closer, I felt like she and I could joke around more, and have more open “adult” conversations, nothing crazy, but when she’d ask how my day was, I’d actually tell her rather than just saying “fine”. Going to the mall and many other errands were still reserved for just her and Lacy, but she started having me go with her to the grocery store, and those big box warehouse type stores. Her reason was that she could use a man to help lift and carry things, this was a little annoying because I knew I wasn’t very strong, I was just tall and lanky. But I also knew she just wanted the company.

The down side to all this bonding was that now when I jerked off at night I had to make it quick and sweet, I kept my boxers on and just pulled my dick out through the opening, and jerked it to orgasm as quickly as possible. Even that was risky, if my parents were being snappy with each other earlier in the evening I could just assume there was going to be a fight, so I had to miss my orgasm for the evening since I KNEW my mom would be coming in eventually.

One of the issues my parents fought about was that my dad worked a lot which, in his defense, was so that he could support his family and not make my mom work too. They liked the idea of her being home when we got home from school. But alas that meant he had some late nights and often had to travel. This was one of those nights.

It was a Friday and my dad wasn’t going to be home till Monday. My sister was staying the weekend at a friend’s, and my mom tried to convince me to stay at one of my friends houses, but I had other plans. I lied and said that no one was available to have me over, but really I had thought to myself that tonight I could finally have another really good jerk! If my dad wasn’t home, then no fighting, and I got my room to myself! My sister went to her friend’s right after school, so it was just mom and I. We ate dinner and watched some raunchy comedy that made lots of sex jokes, that my mom would jokingly scold me for laughing at. She sat right next to me, leaning against me, and we had a good time.

When I eventually went up to bed, I didn’t rush into anything, I just laid in bed thinking of stuff to get me turned on. At this point in my life I wasn’t into anything special, mostly I just closed my eyes and remembered pictures from magazines that I’d gotten to see.

As a virgin, I didn’t know what sex was like, so I didn’t have a favorite position, or know if I preferred tits or ass or whatever. I just liked the way naked women looked, and I imagined masturbating must’ve felt just like a women’s vagina. I didn’t have access to a computer in my room, so I hadn’t seem much porn, I wasn’t even familiar with blowjobs or hand jobs, although, a friend of mine had a girlfriend who gave him head regularly so I’d heard of them. He would describe it, and it sounded amazing, the whole thing; The way it looked to see her sucking on it, the image of her head bobbing up and down in his lap, and the way it felt to just be relaxed, sitting there not doing anything and just cuming in her mouth, no mess or anything! So when I masturbated, it was usually to an image of me laying on the bed (since that’s the way I usually jerked off) with a beautiful woman kneeling at the foot of my bed sucking my dick, I never did anything, I just laid there. Well, I’d gotten pretty turned on by now, and I’d already heard my mom go into her room, so I figured it was time to start.

I pulled my hidden stash out from under my bed, a pump-bottle of lotion, a towel, and a Hustler magazine from several years ago. I rarely pulled out the magazine due to the extra risk of being caught, but tonight I was going to go all out. I stood up and pulled off my boxers. I was already rock hard, so I just stood there gently stroking myself, enjoying the feeling of not being rushed. I opened the magazine to my favorite picture of a woman with huge tits, straddling a man. It was taken from his point of view and was the basis for many of my masturbatory fantasies. I set it on the bed and stood over it looking down while gripping my cock tighter and building up speed. I pumped a couple shots of lotion into my hand and smeared it all over my dick. I particularly like working the head, it’s big and really gives my dick the whole “mushroom – tip” appearance.

I enjoyed getting myself close to the point of no return, and then slowing down or stopping and letting the impending orgasm subside. It was like I was teasing myself, but really I was just taking my time, and the build up always gave me a better orgasm. I laid on my bed and kicked my blankets completely off and onto the floor. I got comfy, closed my eyes and started up again. The feeling was incredible, I rarely even got to use lotion anymore, so this moist-silky feeling of my lubed up hand was a real treat! I was building up a faster rhythm again, and was thinking about whether I should just go for it this time, or slow back down again and let it build back up ... when my door opened and my mom walked right in.

“Hey sweetie, do you mind if I ... oh my God!”

I was completely nude, spread out in the middle of my bed with the biggest hard on I’ve had in weeks!

“MOM! What the fuck are you doing? Stop! Don’t come in!”

But she was just staring at me, frozen from a combination of shock and embarrassment. I was reaching around for something to cover up with, but my sheets were on the floor at the foot of my bed, so I just threw the towel over my lap and sat up, leaning forward, trying to conceal my erection. Finally coming to her senses, my mom covered her face and turned around.

“I’m so sorry sweetie! I didn’t know! Dammit I should’ve knocked, I’m so sorry, I didn’t mean to embarrass you, oh my God, please forgive me, I was so stupid!”

Well now my first reaction of anger turned to pity, I didn’t want her to feel bad, “it’s ok mom, I’m sorry I yelled like that, I’m not mad”

“Really? I honestly didn’t know.”

“It’s fine, I just got embarrassed.”

She turned back towards me and opened her eyes. “Trust me, you’re not the only one who’s embarrassed.” She picked my blanket up and handed it to me and sat on my bed. I covered up and sat there. We smiled at each other reassuringly. “I should’ve known that you were doing this already, you’re at that age, plus when you got that boner from rubbing up against me, that should’ve been a red flag that you’re probably getting hard-ons and taking care of them somehow.” I just nodded. “How long have you been masturbating?”

“A year, maybe a little less I suppose”.

She nodded, and noticed the Hustler sitting on the bed, she picked it up before I could react, “is this what you use?” She was flipping through the pages, I just nodded, blushing. “It’s ok, every guy has jerked off to one of these magazines.” She looked up and me, and I grinned, awkwardly comforted knowing that she didn’t think I was weird. She leaned forward with her arms open to give me a comforting hug, I leaned in, then stopped.

“Um, I’m still hard.” I moved my hands away so she could see the tent my cock was making, “Ill pass on the hug.” I gave a little chuckle. She laughed to, but stared at my crotch for an extra moment.

She went back to thumbing through the magazine “do you have questions about any of this?” I shook my head NO instinctually, not wanting to talk to my mom about sex. “Because this isn’t reality” she continued. She turned the magazine towards me, showing me a picture of a close up of a woman spreading open the lips of her vagina.

“It’s not?” I replied, she had peaked my interest, and I really DID have questions.

“No, she’s just trying to look exciting for the camera, vaginas don’t normally look like that”

“What do they look like then?”

“Well...” She looked around, unsure how to proceed, “Well...” She stood up, reached under her nightgown, pulled her thong off, and then lifted her gown up to her bellybutton, showing me her pussy, “They look like this.” She wasn’t shaved bare like the girls in the magazines, but it wasn’t a bush like I’d seen before either. She had hair, but it was short, like she meant it to be that way. I just stared unable to blink. She sat back on the bed, still lifting her gown, and facing me. I could feel her watching me stare at her exposed vagina, I should’ve been embarrassed, but I couldn’t look away. “See, they shave hers completely, and she spreads the lips like that to make it look sexy”.

“That’s stupid, it’s looks good, just like this”

“Oh hush” she covered herself, and I looked back up at her face.

“No really, that looks really nice, it looks intimidating in the pictures”

“That’s because she’s playing with it in the pictures”

“Oh, so you’re not supposed to play with it?”

“Well, sure you are, but she’s just spreading it open for the camera, in real life you’d just rub her clit, or finger her”. I must’ve looked confused, because she lifted her gown back up and continued... “This is the clit, you just have to rub it, but when you’re fingering a girl, you slide a couple fingers inside her”.

“Inside her where?”

As if she was a teacher giving a hands on lesson, she took my hand and pulled it to her vagina, she curled all my fingers closed, except the index and middle fingers. She leaned back slightly, and guided my fingers to her opening. “Right here. You just slide your fingers in and out, the same way you would with your penis if you were having sex.” With out thinking I pushed my two fingers in and she let out a sigh, I did this about three times before she grabbed my wrist and stopped me.

“Was I doing it wrong? I don’t really know what to do”

“No, that felt fine, especially since it’s your first time, it’s just that...” she paused and looked me in the face. “You shouldn’t be doing this with your mother”.

“Oh!” I just realized what she meant, and she was right, I pulled my hand away, “I wasn’t thinking about it like that! It’s just that you were the one who put my hand there, and I was curious, I’ve never tried that before, I was just seeing what happened when I fingered a girl, so I don’t look like a dork when I finally get a girlfriend”. I felt like a idiot, and my expression obviously showed that.