I masturbated pretty much every day, and it was so much of my routine that I kept a jar of Vaseline on the shelf by my bed, naively thinking my mother - she was divorced at the time, and I was the only of the kids still at home (probably part of the background for this) - would not know what it was for. My room was just off to the side of the front door. It used to be a study. The real bedrooms were used by my sisters when they visited. Even though they had left for college and only came home on occasion, I didn't bother claim one of them, because I was going to be going to college shortly myself.
If I got the urge right as I woke up or was going to bed, I would lie on my side and clean up with a wash cloth that I also kept nearby. But during the day I would stand, pants pulled down, looking out the window from a safe distance, because my typical fantasy was masturbating in front of Caroline Parker, a girl two years younger than me who lived across the street. I would imagine her looking into my room from her bedroom window, shocked at what I was doing, being initiated into the male anatomy and sexual function, and aghast at what came shooting out of me at climax. I guess I had a bit of exhibitionist streak, or maybe I was still too protective of her to have the fantasy of actually fucking her.
I was thus engaged, and at the verge of climax when my mother knocked on my door. And this is the point of the impulse that was new to me then, but that I have experienced many times over the years, the deep-seated, primal urge to push as far into a woman as possible to shoot deep into her, to push up against her cervix. The urge to have a woman watch - like I wanted Caroline to watch with a sense of amazement and a tinge of disgust - at all of the cum spurting out; to cover a woman with the cum, on her breasts, her face, into her mouth, into her anus.
At that moment, there was a woman on the other side of the door, ready to come in, ready to see my climax and the wonder of my ejaculation. It was my mother. But in that moment when I was so blinded to anything rational, it was a woman. I could have shouted to wait, to not come in, but instead I faced the door and kept driving my hand up and down, trying to hold it in for just one more second, until the door opened. At that moment the opening of the door could have been the parting of the lips into her vagina. It was as if I was entering her even as she was entering my room.
She opened the door, looked at me as I looked at her with my face having the grimace of climax. In the complete surprise of the moment she did not avert her eyes or turn away, at least not for the two or three seconds it took for my cum to squirt out in repeated spasms. And her eyes, quite naturally, focused on that.
I think back to that moment as my first sexual experience. The first time I had come deep inside of a woman, that I had cum all over her face. That I had stuck my cock in her ass. She looked with shock, but also had the look of amazement, or what I took as the amazement that I fantasized a woman would have in seeing me complete the act. She let out a gasp, a "whoa", looked up to my face and at the cum that had dripped to the floor. She then turned and walked out, quietly closing the door as if she was afraid to wake me. I was guilty at what I had done, ashamed, but as the last of the semen oozed out and onto the floor, I also felt that I was watching the cum drip off of her, off of her face, being spit out of her mouth, oozing out of her cunt.
I stayed in the room for a bit, but realized I would inevitably be confronted by her on this, and felt it was better sooner than later. As soon as she heard the door open, she came up to me. "I know you do that. Every boy does. But I shouldn't be seeing you. I respect your privacy, I knock before I come into your room. But you also need to be more thoughtful. It's really not right."
I replied in a way that recounted the image of that moment, that still dominated what might have been a natural embarrassment, "I'm sorry you saw that, but I really couldn't stop. It was already shooting out."
Then as now, my masturbatory fantasy moved toward reliving that moment. My mother replaced Caroline Parker as the object of my sexual display. My mother was watching in amazement and approval, in shock and awe at the cum spurting from me. The difference between Caroline and my mother was that my mother was in the house with me. She was accessible, and she already had seen it for real. It was not a fantasy.
And, it could happen again.
Having now felt of my mother in that sexual moment as simply a woman, and again and again masturbating with this recollection as my fantasy, I had pushed beyond the mother-son barrier. I could look at my mother and know that in the current moment of us having dinner or of me watching her clean the house she was my mother, but that in another moment of me closing my door, taking the vaseline and working my cock into its climatic spasms, she was the sexual receptacle for my passion of that moment.
And what kept this fantasy from a further reality? Nothing more than my door! It was as if the door was the thin fabric covering her, separating me from entering her, from her seeing me in my sexual moment and me seeing her in her response.
So I pulled away the door just as surely as I might pull up her nightgown. This I first did as I was blinded by the excitement of masturbating. In that moment I would go over with one hand still rubbing my cock and pull the door ajar. I would then turn to the side, so that I could not see if she was coming by, and so she would realize I could not see her. I would pretend she was watching. But maybe it was not just my imagination, maybe she really was. It was exciting, and my sessions reached a new level, and my schedule for this activity changed - I masturbated only during the day, and only when she was at home.
And then came the time that I knew she was watching, because I could hear her. The sound of her footsteps coming toward the front door and then stopping. There would only be one reason she would stop there. I worked by cock harder, wanting to finish before she might turn away. And I did. Because it was only after I was finished that I heard the footsteps continue.
The corner had been turned. I had started to see her and fantasize about her as a woman, and she was now seeing me as a man - or at least as someone with a penis that could perform.
Looking back now, and indeed even as I thought about what was happening then, the progression to her having a fascination of whatever sort with my sexual acts was not totally surprised. A little bit about my mother:
My mother - who has passed away, otherwise I would not do this even anonymously, and who passed away a few years ago, otherwise I could not recount these events - was a very attractive women, petite with bleached blond hair and blue eyes. But even as I write about her, and even as I masturbate to these memories, I don't really think of her in physical detail. It is an image rather than a photographic reality.
She wanted to be Marilyn Monroe. She needed every man to pine after her, and it was more than being flirtatious. She needed to have men take her to bed. It was her way of proving that she was a sex goddess. (One of my sisters, who later became a therapist oriented toward psychoanalysis, told me that our mother was clinically narcissistic.) This she did even while she and my father were married. He knew about it but could not control her extramarital flings.
Thus they got divorced, but only because her activities were becoming common knowledge. My father had to act as if he did not know, and thus he became an object of pity or derision. He moved to a new community after the divorce for that reason. So, if this is what she needed from men, then why not from her son as he matured. And why not from her son as she began to see him in his raw sexuality.
But there is more. I was the only son, with older sisters. My mother would often tell me the story of how she would check my penis to revel in the fact that she finally had a boy. And when I was very young I would get into bed with her, my father sleeping in a twin bed, and we would look at my penis to see if it was asleep or awake. I didn't know what an erection was about at that age, but of course she did. The point is that she saw me in a sexual way even before all of this occurred, and between that and her insatiable interest in sexual conquest and confirmation of her self worth, there is a reason she would continue to watch my time and again.
Then, as with almost any sexual encounters, things progressed. The obvious start of this was that even though I was not looking at her, she knew I had become aware that she was observing me. She made sure I would know by making her presence more obvious from shuffling her feet outside my room. In fact, it might be that this was her intent even the first time I realized she was there. All that it took now was for me to turn toward her as I was reaching the end. Maybe she would turn away, but maybe she would continue to watch, and my fantasy would be complete.
And she did continue to watch. She looked with her Marilyn Monroe smile, her eyes glinting, her head cocked a bit to the side, and her mouth slightly open, like at the start of an "Oooh, oooh" that could be married to an orgasm or to seeing a man exposing his engorged cock. She was seeing me just as she did all of the men. And with admiration and pleasant surprise as I came to my release. So now my routine became not only maturbating with the door open, but having it open was the sign for her to come by and watch me.
Mom didn't stay on the other side of the door for long. When she and I knew we were in this mode, she came in closer, until I was coming right in front of her, with her looking down at the tip of my penis as I squirted out. Women have told me that ejacuation is not as erotic for them as men make it out to be, but for my mother it seemed to be a never-ending source of excitement. With her so close to me, I had to do it - I pushed against her to cum on her. My cum hit her blouse and rolled down onto her skirt. She didn't move away. After the three or four squirts, she rubbed her blouse. It worked more into the fabric, she smelled her hand, and said we would have to be more careful and control where I was "squirting that thing."
The operative word in this was "we". From then on she took my hand and helped "direct" my penis as I came off. And directing it started earlier and earlier in the act, and went from doing this by moving up and down with my hand to taking the shaft of my penis, near its base under where I was rubbing. And this then went to helping me rub, and then to her taking over. Mom now had gone from an observer, which of course is bad enough, to engaging in a sex act with me: a hand job, though at the time I didn't know that that was a thing. I thought what she was doing was a new and special act.
Summer was half over, and it was only a month before I was out of the house. And with my going to college, we both knew that this would come to a close. I didn't know what this meant for Mom. She didn't show any signs of being turned on from all of this herself, and if she had to find a sexual release, she was doing it afterwards quietly behind a door that did stay closed. Nor was she being overtly sexual outside of our brief periods in my room.
But I started to sense that she had to complete the act. That, as I know it now, she could not let me go without having become a sex goddess to me. The manifestation of this, the point where it was clear things were moving in this direction, was that she kept her nightgown on longer into the day. My complicacy was that I gave the door-ajar signal while she still had it on. I wanted to do it while she was still in her nightgown because with her nightgown, there really was only that sheer sheet of fabric between my cum hitting her clothes and hitting her body.
And we had dispensed with the redirection of my ejaculation. So as another addition to the routine, I came on her every time, and every time I did, she put her nightgown in the wash. Mom didn't wear anything under the nightgown, but the nightgown itself was modest, opaque and covered her body. It was functiona. I imagined going with her as she pulled it off afterwards, but I never did, and she never suggested I should. So for all of the intimacy of a purely sexual nature, and my total abandon in front of her, I had never seen her act sexually herself, nor had I seen her naked body.
My room had a desk against the window, and a set of twin beds set perpendicular to each other, with padded cubby holes behind them for pillows and the like. And my vaseline resting above it. I had a bare wood floor; if it were carpeted it would been stained beyond redemption.
One time, unlike any other time, she stopped rubbing part way through and held my penis firmly. Using it as a guide, she turned me to face one of the beds. "Close your eyes, and promise to keep them closed." I looked at her, and nodded as I shut my eyes. Her grip shifted and she pulled me forward. The she let go, and a moment later her hand gripped my shaft again, pulling it gently forward, then down a bit, then forward again. I could feel warmth and softness and moisture on the tip, and I instinctively pushed toward the wetness as she pushed back toward me. I was now in a world of quiet, darkness and pleasure.
My mind went blank. I couldn't process what was happening. I actually didn't know where I had entered, or wasn't willing to process it. Could I really be inside my mother? Could it be her mouth? But then my hands moved up and they came to the cheeks of her naked ass.
I had to be sure. With my palms cupped along each of the cheeks, I moved my right hand to the top of her crack down, then ran it down the crack over the dimple that was her asshole, and just below that to her skin stretched against the top of the shaft of my penis. I thrust slowly and could feel my penis moving in until my finger was touching my hair at the base and then out until I could feel the ridge of my head. I moved my hands back to using her cheeks as grips and continued thrusting slowly and deeply.
This was a different sensation from all the days and nights of jerking off. I was not in control of the pressure on my penis. And there was no firm grip running up and down my shaft. It was like I was moving through a warm, dewy cloud. The only sense of friction and rubbing was on the underside as I pushed forward, and then only if I rocked up and down as I did. And this was also new: there was the feeling of pressure on my tip at the end of my thrust - I was pushing up against the top of her vagina.
I felt one of her hands rubbing herself just above my shaft. Her fingers occasionally swirled along me, her nails giving little scratches. I was finally seeing Mom pleasuring herself. She was going faster and faster, hitting against my shaft harder and harder as she did. Then she let out a sound, "uh", in a deep voice that was not her own, like with a cough. Mom's body shook, the walls of her vagina squeezed against me, which made me want to thrust all the harder.
Then with a shiver she stopped. I didn't know what to do, but she said, "Keep on going. Do what you want. Finish." I was still trying to understand all that happened, not moving. She pushed her hips back to get me in deeper and said, "Finish inside me. You can."
I don't even have a sense of how long I kept thrusting. I was outside my body and my consciousness. The sensation was unlike anything before. The pleasure was muted and distant. And when I did climax, it was not intense with the feeling of the cum shooting out. It was a more gradual release, like feathers dusting my shaft rather than a hand pulling up and down synchronized with my contractions. I came while pressed up against the top of her vagina, and the cum felt like it was oozing out rather than shooting.
I stayed inside her until I was limp. She stayed kneeling over even after I slipped out, and said, "You can open your eyes now. Look. Look at what you've done."
I looked down to see her rear and the crack that I had run along with my finger. She put her head down further on the bed and hiked up her hips. I took a step back. Her legs were slightly spread, opened up so I could see her anus, the first time I had ever seen anyone's. The wrinkled brownish skin along the rim seems like a funnel into the hint of a hole. I ran my finger along her crack again and stopped it to rest right on the hole. I pushed in a bit, but it was closed shut, and I was also thinking, shit has been stuck against that skin, and come out of that hole. It has the slickness of her shit. I resisted the urge to smell my finger. And on either side, her cheeks were dimpled from age. They hung shallow on her pelvis.
I stepped back a little more. I wanted to see the secret garden that I had just entered. But what I saw was hair. Curls of thick hair going from just below Mom's asshole then running between the tops of her thighs, and the around the mounds that formed the lips of her vagina. And in the hair, slowly streaming out of her, was my cum, white against the sea of black hair. A crack that led down to a little ass hole with the brownish slick, then a forest of hair that ran along barely a discernable mound with a slit in the clearing. And globs of cum. And that was it.
I had imagined that to see a woman's slit, to see her from the rear like this, would be to have an irresistible urge to mount and fuck her. But there it was in front of me. Hair and an ass hole. Shit and cum. And in all this, almost as an afterthought, I was looking at the asshole and hairy cunt of my mother, and the cum leaking out of her was my cum! I thought this, and the thought seemed profound and disturbing in the cosmic sense, but in the present, in the act we had just completed, it didn't really matter to me.
Nor, apparently, to my mother. She moved up and off of her knees and turned to sit on the bed facing me. "You've had a good look, and now I am going to clean up." She pulled her nightgown down and a looked at it busily as she straightened it. The she looked down at my feet. My pants were bunched down by my ankles. My shirt was hanging just above my crotch, my penis, now limp, peeking out like the head of a little hamster. All in all not a very inviting look. The look of a teenage boy after his first time. She reached her hands behind my thighs to bring me closer.With my release, my balls now were hanging down long and heavy. Mom cupped her hand under my balls, and moved them up and down, squeezed on one and the other like she was testing fruit for ripeness. Then she took her other hand and pulled my penis from its resting place on my balls, took the tip toward her and squeeze the head so the tip opened up, and spoke to it like it was a sock puppet. "Where have you been lately?" With a little forward pressure on my sac she pulled me closer and rested my limp dick between her lips, and gave it a little kiss.
Then Mom got up. "I need to go clean up this mess, it's stinging me," and walked away with her thighs a bit apart to keep the cum from running down them.
I pulled up my pants without cleaning, and went out into the kitchen. We were back to mother and son. I was never going to fuck my mother again. I would repeat the act and see her hairy rear in my fantasies for years on, even today. But I had no desire to do it again for real. My mom was finished as well. She had her Marilyn Monroe conquest.
Though I still kept the door open like had done at the start of our adventure. Sometimes I could hear Mom stopping to watch, but now from a distance, from outside the room. Sometimes she was in the kitchen, but still in earshot. I would groan loudly toward the end, "Oh my God, Oh mommy, mommy please, I'm cumming, I'm cumming."