Sexual Confessions vol. 1: My Mom

The foundation of my strange sex life begins here.

I am about to turn 40 and I have felt the urge to get some of the things I’ve done out in the open. I don’t feel comfortable telling friends about them just yet, if ever at all for that matter. I’m no writer or wordsmith, I am a common man and I use common words. This is just my story.

I grew up poor. Even by America’s standards I was poor. My family consists of my father, a Native American man who came and went. Him and my mom would be together for a few months at a time and then they’d have some big fight and he’d leave for a few months before returning. I hated them both for doing that to themselves and me. My mother was white, and 12 years younger than my father. She was a thicker woman. Not huge, but thick. She had large breasts a big ass and a belly but it wasn’t the kind of fat where people stared and or laughed when they say her in public. I have an older sister that is 10 years older than me. And then there’s me. Quiet, shy and very much an introvert.

As I said I grew up very poor, we moved frequently in my first 10 years of life then finally found a small one bedroom apartment once my sister moved out. Since it was primarily just mom and me we shared the bedroom. My small single bed pushed into one corner and her double bed pushed into another.

Over the years both my parents drank a lot but the older I got the more I noticed that mom was also taking drugs. Nothing hard or scary, mainly just prescribed pills and what not. Mixing them with alcohol would put her out like a light and the older I got, the more I realized how easy it was for me to get away with things while she was out.

This particular time happened when my dad happened to be staying with us. One night when I was 12 I awoke late, 2 or 3 am, to sounds of rustling and heavy breathing. Of course it was my parents having sex in their bed 10 feet away from me. They were trying to be quiet about it but they were getting close to finishing up and they must of lost themselves in the moment and began making enough noise to wake me, which wasn’t hard since I’m a light sleeper.

I wasn’t about to let them know I was awake and at the time I wasn’t quite sure exactly what was going on. The more my eyes adjusted to the dark the more I could see though and I had figured it out. Having an older sister I learned about sex and attraction to women at an early age. My sister is the polar opposite of me, loud, abrasive, and says whatever is on her mind at that exact moment. So whatever sex knowledge I didn’t absorb thru just hearing her talk over the years, I learned from spying on her as a curious child.

Dad stayed with us for a couple more months and I would regularly wake up to the sounds of them fucking and they were never aware of it. It wouldn’t have been hard for them to just go to the living room but they seemed not to care even if I did wake up. That lead me to believe that they were drunk and or on their pills and probably didn’t even care if I woke up. Almost every night I’d wake up hearing them fuck and I couldn’t help but join the fun in my own way. Listening to them quietly go at it, but also have no worries about me being in the room really shaped the way I thought about sex. Clearly it wasn’t as dirty as people lead you to believe if you can just fuck while your 12 year old son is 10 feet away. Every night when I’d wake up hearing them my dick would get so hard and I’d start rubbing it. I started masturbating when I was 11 and was still in that phase where I couldn’t leave my dick alone. Well, at 40 I’m still in that phase, but just discovering how awesome it felt to rub my cock was the best and waking up every night to essentially free pornography made it even sweeter. I’d stroke my cock as slowly and inconspicuously as I could but then realized the more this happened that they probably wouldn’t have noticed if I stood next to them. This went on for about 4 months until their next argument and dad moved out again.

Once again it was just mom and me. I wasn’t sad to see dad leave again because frankly I didn’t like him much then and I don’t now. I was sad to see him go because I was enjoying stroking my cock every night while he fucked mom.

About a week after dad left I woke up in the early morning hours and heard the familiar noises mom made but without the noises dad made. Mom was rubbing herself. It was almost sunrise and the room was lite enough for me to see just about everything. The first time I ever rubbed my dick was when I was spying on my sister and I caught her rubbing herself in the shower. I knew what I had to do. I joined mom and pulling out my cock and quietly stroked it. It only took me 30 seconds before the few little dribbles of cum I could produce came out. A minute later mom finished.

This sparked my interest in spying on mom now as well. I began trying to peek every time she was showering or getting dressed. While she was at work I snoop thru her dresser drawer and play with her panties. The soft silky ones I’d use to jackoff with. The more I snooped around her stuff the more I’d find. I was digging thru her closet and found her lingerie. I’d put it on and look at myself in the mirror then go masturbate.

A few months of this went by before mom sat me down and told me dad was never coming home again. I was 13 now and felt I deserved a real explanation but she never told me why. She just said he’s gone away for good. She was right though, I never saw him again.

In my sneaking around one day I found a dildo mom had gotten herself. Perhaps her knowing dad wasn’t coming back sparked it but it was the first time I had ever seen anything like it. It was pretty big. If I had to guess I’d say at least a foot long. Without bragging too much I’m proud to say that as an adult I have a thick 9” dick and this dildo mom had was definitely bigger than what I’m packing now.

I awoke one morning a couple days later to mom rustling around. She was getting ready for work and about to take a shower. She was also completely naked! She quickly peeked in my direction to see if I was awake and must’ve thought I was sleeping because immediately pulled that big floppy dildo out and quickly exited the room. I waited a minute or so before I got up and crept out the door after her. She was in the bathroom and I could hear the shower running. My cock was throbbing and my heart was pounding out of my chest as I slowly turned the doorknob. As soon as the door was open enough I peeked in and saw she was already in the shower except her dildo was still on the bathroom counter top. I waited another minute or so then saw her hand slip past the shower curtain and grab the dildo. I patiently waited for the familiar sounds of her breathing harder before I slipped in the bathroom. Not completely sure what I was doing I crept toward the shower rubbing my dick from outside my underwear along the way. I slowly peeled the curtain back just enough for one eye to peek in. I couldn’t believe it! She was facing me but her head was tilted back looking toward the ceiling. Her foot up on the ledge of the tub giving me a perfect view of that dildo sliding in and out of her wet pussy. The sounds of her moaning and the water running masked my small noises I made as I pulled out my dick and played with it. No more than 20 seconds before I came in my hand and quickly scampered back to my bed without her knowing.

As she returned to the bedroom in her bathrobe I pretended to sleep as I watched her put the dildo back in her drawer then watch her remove her robe and get dressed for work. When she was ready, she came to wake me up. It was summer vacation for us kids but she still had to work. I was 13 and stayed home alone so she gave me some instructions on what chores I needed to do that day and then left for work.

As soon as her car was out of sight I ran back to my bedroom and grabbed her dildo. Then I went and got my favorite piece of lingerie she had and put it on. I laid on her bed and put the dildo in my mouth. I pretended I was her sucking my dick. I stroked my cock while doing so. Over the course of that day I masturbated this way 5 times before she got home from work. This became the theme for my summer vacation. Spying on my mom and pleasuring myself afterwards.

This carried on for about a year without anything new. Moms pill addiction did begin to worsen and she was masturbating less and less though and my opportunities became few and far between.

I was 14 now and well into puberty. My dick had grown significantly in the last year, and my curiosity grew with it. Constantly looking for exciting ways to please myself and running out of ideas, I laid in bed one night stroking my cock quietly thinking that my mom was 10 feet away and didn’t know what I was doing. I started moaning a bit louder to see if she’d wake up and nothing happened. The next morning I made a decision that would change my life completely.

I found out while eavesdropping on a phone call mom had with my sister that mom was taking sleeping pills. She said she was having problems with sleeping, she was depressed since dad had left and she needed something to make her sleep thru the night. She was mixing them with a few drinks as well and they were knocking her out cold for the entire night. The life changing decision happened then; I was going to push this as far as I could.

Mom had her few drinks and popped a couple pills in her mouth and it wasn’t long before she was out. I waited a bit before I started. First I pulled the blankets off her so I could see her. She was wearing a sleeveless nightgown that went down about halfway between her hips and knees. It was dark blue and silk. Revealing a lot of cleavage, especially when she laid on her back. She usually slept on her side so my plan was to roll her on her back but fortunately she already was on her back. I sat on the edge of my bed and pulled out my cock and began teasing the tip with some spit I put on my thumb. I stood up, cock in had and walked toward her bed say in “mom” every few seconds, each time getting a little louder. No response. I began to touch her belly to see if she responded to physical contact and still nothing. Just rubbing her chubby belly turned me on. I moved my hand down to her leg. Her leg was soft and silky like her lingerie. I shook the bed a bit and yelled “mom” again. Nothing. I crawled into bed and laid next to her. I was completely naked, hard as can be, and laying next to her. Since she was laying on her back her big breasts were flopped to the side and I easily slid the one closest to me out. I knew if she woke up now she’s either be disoriented enough that I could convince her something else was going on or she’d be completely aware and I’d be in a world of trouble. My curiosity, as it always has got the best of me. I had come this far and I wasn’t about to call this night a failure.

My mom had really large breasts, 48DDD to be exact. They were saggy from years of not supporting them properly and her nipples were dark and very large. I started to lick her nipple eventually taking it in my mouth and sucking. Mom snores a bit then and startled me a bit so I stopped. When I realized she wasn’t waking up I returned to sucking. My hand was on her silky thigh and I began to slowly slide it up her nightgown. Trying to pull it up as best I could, I noticed it was looser fitting than I thought and I had considerably easy access to her pussy. As my hand reached her warm mound I found out she was wearing panties. Considering that was the first thing that had gone against me in this endeavor, I was still doing well.

Still suckling on her large breast I softly started rubbing her pussy. I had never touched a pussy before and had very little access to pornography to see what they looked like or where I should touch and since she was wearing panties I figured she wasn’t going to feel anything anyway. I cupped her mound with my hand and softly started massaging. After a few minutes of that to my surprise I quietly hear her making soft noises and I feel a little wetness down there. I thought that was probably as far as I should take it but again my curiosity got me.

Feeling that she was more alert than I had anticipated I moved slowly on the bed and positioned myself between her thick thighs. I softly grabbed the side of her panties and pulled them to the side. There was no reason to sight see since it was dark but I could see mom had a big bush. I started with one finger just feeling around, pushing a little bit until it slid inside her. She was wet but not really wet. I slid a second finger in. She moaned quietly but didn’t move at all. Was I really going to do this?

Once I had gotten into bed with her the end was already decided. There wasn’t going to be anything that stopped me, even when the occasional thought of how wrong it was popped in my head. For almost two years now I had been masturbating furiously thinking of her, or dressing up in her lingerie sucking on her dildo pretending to be her. I couldn’t stop now if I wanted to.

Now that I had felt around and slid a couple fingers inside her with little to no reaction, I knew where to put it and how much resistance there would be. I spit a glob of saliva in my hand and rubbed it on my cock. I placed the tip against her and pushed a little. Nothing happened. I repositioned myself and my dick slid right inside her. Her pussy was wetter than I had realized. Her warmth felt amazing! I lost track of my thoughts and just laid on top of her feeling her warm, moist vagina swallowing my cock.

She still laid motionless and if she made any noises of enjoyment I didn’t notice because I was lost in my ecstasy. After a few seconds I slowly began to slide my dick in deeper and back out. She was making noise but I was still ok. A minute or two later I pumped a load of cum inside her. I had never imagined it felt this amazing to fuck someone. Cumming in a vagina felt a million times better than my hand. When I finally calmed a bit I pulled my cock out of her and still felt drops of cum trickling out. Slowly I climbed out of her bed and cleaned up as much as I could. Before putting the blankets back on her and crawling into my bed. I was on cloud nine! I couldn’t believe I pulled that off! And on my first try!!! How far could I take this? Can I get away with this every night? What else did I want to try? Oh shit! I just came inside my mom! What if she got pregnant?!

I put everything on hold for a couple weeks. The only thing I thought of was; is my mom walking around with my baby in her? I didn’t touch my cock for over two weeks I was so scared. I kept checking mom’s tampons. Are there any in the garbage? How many does she have? How many did she have yesterday? I knew what to look for since my curiosity made me ask her years earlier what that thing in the garbage was. I just wasn’t finding anything! Finally I got up one morning and checked the garbage can in the bathroom and there was a used tampon. Two plus weeks of fear and dread instantly washed away and I could start plotting my next move. I just had to get some condoms. I’m not making that mistake again….

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