Mom & My Many Firsts Ch. 01

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I was a 19 year old virgin with no experience.
4.4k words
4.1
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Part 1 of the 3 part series

Updated 06/08/2023
Created 04/08/2017
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I'll start out by saying my mother and I love each other very much. My father left her for another woman when I was very young. And she remained single throughout my childhood, while doing some sporadic dating. She was 5' 7" with small to medium breasts, slightly wide hips, a nice figure, and green eyes to go with short dark brown wavy/curly hair.

Our time together was quite normal as I grew up. Mom taking me to my baseball games, etc. She always did what she could to make my life as enjoyable as possible. I wonder now, how much of her attention to me, took away from her needs. I had just turned 18 when I started noticing the possible resulting affects of little dating and mostly doting on her son. My mother began what I would surmise to be, showing some signs of wanting what she hadn't been getting. And that was intimacy with a man. I was clearly displaying the appearance of a young man, and had grown to 3 inches taller than mother by then. It's possible my changing appearance and her unsatisfied urges may have happened to cross paths at just the right time. Nothing dramatic happened, mind you. She just decided she wanted me to see her in a different light, shall we say.

I must preface this by saying I curiously felt no sexual arousal initially. But I did look as much as I possibly could. Weekend mornings during the warmer months afforded her the opportunity to begin wearing a shear full length lilac colored negligee with a floral stitched pattern in a v-neck down the front from the neck to the breasts. It was quite evident within the light of the room that she had nothing on underneath. I could see to a certain degree her breasts, dark pubic mound, and crack of her behind. It was very evident when she approached the southeast windows. Especially on a sunny morning. I can't begin to tell you how many times I sat at the dining room table eating a bowl of cereal while watching my mother wash dishes with the light from the window above the sink illuminating my mother's feminine features underneath. I definitely enjoyed watching her breasts, always with erect nipples, sway slightly as she moved her arms. I've always loved a profile view of a woman's bare breast. That was definitely my first. She had to know I could see through the material, didn't she?

My mother continued to wear that negligee, which I never tired of seeing. But at some point, that apparently no longer was enough for her. Her bedroom was directly across the hall from the bathroom (mine was right there at the end of the hallway as well). And she would always enter the bathroom wearing her pink bathrobe when it was time for a shower. She may have wandered around the house a bit before her shower, but that's what she always wore. One day, I could hear she had finished taking a shower. Everything was normal as could be until she opened the bathroom door. I don't know if she waited to hear me approaching the hallway or not, but as I got closer, the bathroom door opened, and as she exited, she was not wearing her robe. She held it to the front of her body so that it would be covering her "private parts" as she stepped into her bedroom. She looked at me as she crossed the hall and proceeded to close the door behind her. You don't just not put your robe back on unless you want to be seen. That was the first time I felt a little funny about seeing my mother that way.

I guess at this point I should tell you a little about me. My name is Rich, and I'm 5' 10" with an average build. I was a 19 year old virgin still living at home at the time my mother and I began having a more hands on relationship. My sexual activity up until then, consisted solely of masturbation. The material I used was basically pictures of naked women from some magazines. And since I didn't have anyone to guide me or make suggestions regarding masturbating, I did it the way it made me feel good. I am only 4 inches when fully erect, so this may have played a part in my technique at the time. I would gather my pictures and lay on the couch naked. The cushions sank nicely under my butt, and allowed me to raise my legs and push my erection between my thighs and close my legs together. I'd then open them just enough, as I pushed my hips forward, to have my hard penis rub against my thighs as it came free. I'd repeat that process while looking at my girls until I had a wonderful orgasm all over my thighs. I would often do the same thing in the shower with a wonderful helping of slippery soap.

Regarding my picture collection, some of the women appeared with no pubic hair. I found this particularly exciting and wanted to try it myself, but couldn't muster the courage to do so for the first time, until I was starting college. By then, there was no need for anyone to see me naked, so it felt safe to do so. More often than not, since then, I have been completely shaved.

Getting back to my mother, her robe-less, front covered display became more frequent, but seemingly to her dismay, I wasn't providing any outwardly discernible reaction when seeing her. I say this because when I was 19 and just finishing my first year of college locally, she decided to push the envelope and stroll to the bathroom for her shower without anything on. She made sure I was in the vicinity before appearing from her bedroom. Her pink nipples were rock hard and there was no doubt she was excited to have me see her in all her glory. She stopped and turned to face me and asked if I needed to use the bathroom before she took her shower. I just said no as she watched my eyes wander all over her naked body. I couldn't help it! That brought a bit of a smile to her face as she turned to enter the bathroom. Here she was, exposing herself to me, while I always took great pains to never be seen naked. Just a pair of shorts sometimes, of course, but not naked! That was my fist time seeing a woman naked in person.

The next day was Saturday, and when I awoke, I heard the kitchen faucet turn on as I rubbed the sleep out of my eyes. I put on a pair of shorts and headed to the kitchen to get a bowl of cereal for breakfast. To my surprise, there was my mother, naked, doing the dishes. "Good morning, Rich" she casually said, sounding like she's done this a million times before.

"Good morning" I replied, trying not to look too shocked. "Didn't you forget something, mom?"

"No" was her short response.

I wasn't sure if I should turn around and leave or try to appear calm like nothing was wrong or different. But once again, I couldn't take my eyes off her hard pink nipples, and I decided to stay. I just got my cereal and sat at the table and began eating. Her head start this morning allowed her to finish washing the dishes a little before I was done, so she walked over and stood right next to me. "I'll take that when you're done." There were those hardened nipples on what actually were pretty nice breasts just a couple feet away from my face. They were just a nice handful. I was having my last few spoonfuls when it happened for the first time. I felt a stirring in my shorts as I began to harden. A feeling of panic mixed in with my growing arousal as I realized getting up to leave the table was going to present a problem. She took my bowl when I finished, but somehow managed to maintain eye contact while returning to the sink. There went my small window of hope to make it back to my bedroom undetected. Worse yet, I then heard "would you be a dear and help me dry and put away the dishes?"

"Can't we just let them dry on their own first?"

"No. I don't want to look at them. Let's get them finished" I tried to subtly position my erection, so it wouldn't show, but I couldn't tell if it would work until I stood up. I pretty much knew what the result was going to be anyway. I had a tight pair of shorts on that weren't going to do me any favors even if I did have a small penis. So I stood up and hoped for the best. I only took one step forward when I heard "what have we here?!" I stood still and remained silent while avoiding eye contact. I think she finally achieved what may have been a modest goal of giving her son an erection, thus giving her a sense of accomplishment and sensuality.

"Do you have an erection?" as she began approaching me. I was surprised at how I could barely move or talk. "Cat got your tongue, honey?" I just nodded as I felt my face begin to flush with embarrassment. "Did I do that to you?" I swallowed hard and slowly nodded again. "Let's see what I did to you." I was surprised by her aggressiveness as she reached out to slide her thumbs inside my waistband. I sensed a brief hesitation on her part, as if she was giving me the opportunity to stop her, but like I said, I could barely move or talk at the time. So it wasn't long before I felt my shorts and underwear begin to slide downward. I just looked past my mother and into the kitchen as I felt my clean shaven little erection pop into view as my shorts passed over it. I was wondering what she'd say as I felt my shorts land at my feet. "Wow! Without any hair, you look like you did when you were a little boy! It's been a long time since I've seen you nude, hasn't it?" I gave no reply as she raised each of my knees so I could step out of my shorts. My mother then reached around and gently put her hand on my bottom as she guided me to the dishes. There we were. Both naked, drying dishes. My first time being naked with another woman.

We spent 5 to 10 minutes on the dishes until they were all put away. All the while, my penis stayed very hard. She thanked me for the help and asked me if I was going to stay hard all day. She said this while while lightly running her fingertips along my erection, which sent a jolt through me. "Why don't you find something on TV for us to watch. Don't get dressed. I'll be right back." And she headed down the hall to her room. It really didn't matter much what was on TV. My head was spinning as I stood naked in the living room. A couple minutes passed, and my mother returned wearing a pair of shorts and a t-shirt with underwear clearly on underneath. I don't remember what I chose to watch, and it's not important anyway, considering the situation. My mother laid on the couch on her left side with her left hand between her cheek and a throw pillow at the end of the couch. She patted the couch and said "Lay down here with me." As I walked over, her eyes were gazing at my lightly bouncing 4 inch erection. I sat down and raised my legs onto the couch and assumed a spooning position with my mother. She then moved her right hand, which had been resting on her hip, onto mine. The TV was on, but every inch of my skin that was in contact with my mother was all I could think about. My heart was racing. I don't think I was waiting for something to happen. It was just, how surreal is this? Here I was, cuddling with my own mother, in a sexually aroused state completely exposed to her gaze or touch.

As time was passing, she would occasionally give the impression of getting stiff or uncomfortable. And when that happened, her right hand would slowly inch forward down the front of me. Oh yeah, I was paying attention. It wasn't very long before I felt a fingertip make contact with my smooth balls. A few more sighs and movements and her hand was now completely cupping my bare balls. Nothing was being said as this was going on. Then came the subtle little finger twitches as I felt my balls slightly shift now and again. Eventually, her palm started to flex and her fingers began moving smoothly as she began gently caressing my balls. My legs being together as they were lying on my side, didn't allow much room for her hand, so since my mother's hand was feeling so good, I turned to my right to face the ceiling as best I could and raised my right leg up a bit. This allowed her better access to my balls, and access them she did. There was a much more pronounced lifting, separating, and juggling of my balls as my breathing began to deepen.

"Mmmmmmm. You like this, don't you, Richie?" she whispered in my ear. I just nodded. "I like doing it to you." I started feeling lubrication land on the front of my left hip as my penis began dripping with arousal. Being as small as I am put the drippings close to my mothers hand, and it wasn't long before she felt it. "Oh my, honey. You like this more than I thought." And with that, I felt the palm of her hand rub my balls as she reached for the small pool of lubrication on my hip. I looked down and watched as she slid 3 fingers through the slippery liquid and raised her hand to take a firm grip of my penis for the first time. I felt her hand resting against my bare pubic area as I saw just the head of my cock sticking out above her thumb. She seemed to be just taking in the sensation of having a penis in her hand for the first time in a long time. We both must have been watching her hand hold my cock, because as liquid continued to ooze out of the tip of my penis, she rolled her index finger over the head to the other side to spread the new addition around. She then cocked her wrist and began a slow up and down motion while additionally giving her hand a twist. She quickly spread the lubrication all over my hard shaft, and began a more straight up and down motion. What a feeling that was! I had never done it that way, and it felt wonderful! That was my first time being stroked by another person.

"Turn the TV off, honey. We don't need it on anymore." As soon as I pressed the remote, the squishing sounds of my mother's hand on my erection became much more audible. I could sense her breathing had changed by now as well, as I'm sure she was feeling some level of sexual excitement. A few moments later she said "stand up, honey." I did so as she let go of my penis, as I did so, I turned and faced the couch as she assumed a sitting position in front of me. She immediately took my penis back in her right hand and began stroking again as her left hand began caressing my balls. She started to smile and said "look at my bare baby boy" as she leaned in closer, still looking all over my genital area. Then in one motion, she opened her right hand, closed her eyes, leaned further forward and pressed my erection against her right cheek.

A purring "mmmmmmm" came from inside her as she took in the sensation of having my cock against her face. She then pulled her face away while letting my cock slide along her cheek. She then looked up at me and leaned forward, putting her lips on the head of my penis and gave it a quick kiss while smiling. My leaking never seems to take a break when I'm aroused, and now was no different. As she pulled away from me, my penis and her lips were still connected by a string of lubrication. She took hold of my penis and leaned forward. Out came her tongue for the first time, and she gave my slit a firm single lick which took care of the problem. She closed her mouth and I watched her swallow. It wasn't my cum, but the thought immediately crossed my mind as my cock slightly jumped at the possibility. That was the first time my penis came in contact with another person's mouth.

She still had a hold of my penis after swallowing, and looked up at me again. Once again she returned to the tip and gave it another kiss as she looked into my eyes. This time her lips were softer and allowed the head to make an impression in them. She wasn't quite as quick to part ways with my penis this time either as she appeared to be searching for a reaction from me. All of this felt wonderfully new to me, still being a virgin. So I had to have some sort of look of pleasure on my face. I think she saw that as she leaned forward once again. Only this time, instead of her lips being pursed, we looked into each other's eyes as she opened her mouth and gently took the head of my penis into it. She closed her lips around it as she continued to look into my eyes. I felt the tip of her tongue sliding all over it as my ass cheeks, of all things, tightened, and I wanted to go up on my tip toes. She could tell that I liked what she was doing, and she moved forward as I felt her lips slide along my shaft until her nose easily rested against my pubic bone.

We maintained eye contact as I felt her tongue slide back and forth under my shaft in the wet wonderful warmth of her mouth. "That feels unbelievable, mom." That brought a smile to her face as she closed her eyes, put her hands on my hips and gently pushed them backwards. Her head remained still as I watched my penis begin sliding out of her mouth. As soon as I felt my corona reach her lips, she stopped me and started pulling my hips forward again as I watched my entire penis easily disappear back into her mouth. She repeated this until I started moving my hips on my own. I was now watching my penis slide in and out of my mother's mouth as I thrust back and forth. After a few blissful moments, I briefly stood still, savoring the feelings I was having. I guess my mother wasn't ready to stop, as she began to bob her head back and forth. I could feel her starting to suck harder on my penis as that familiar tingling inside started to build as I began to softly moan and soon told her "I'm ready, mom." She immediately began to slow down until she let my penis out of her mouth.

"I want to watch you finish for me, honey."

"But..." I weakly protested as she stood up and took my hand and guided me back to the couch.

"Lay down and stroke your cock for me."

I laid down as she said, still in a state of bewilderment as to why she stopped. I was so sure she was going to let me cum in her mouth. "I don't do that," I said.

"Do what?"

"Stroke," as I motioned my hand up and down near my penis.

"You do masturbate, don't you?"

"Yeah. Just not like that."

"How else would you do it?"

Even though we had done what we had done so far this late Saturday morning, I had never spoke of or more importantly performed the act of masturbation with or in front of anybody else. So I was a little reluctant and once again felt a rush of embarrassment come over me. She saw my face begin to redden, so she sat down next to me on the edge of the couch. "It's okay. Just do it the way you like to do it. I want to watch." She smiled as she adjusted her clothes so she'd be completely ready to devote all of her attention to what I was about to do.

I thought about the fact that I love my mother and somewhat convinced myself that it would be some level of a bonding moment between a mother and son. I took a deep breath and began to raise my knees, pulling my feet closer to my body. My mother looked back at my legs with a bit of a surprised expression on her face. "Do you want your pictures?"

"You know about them?!" I was mortified.

"Of course I do, silly. Want them?"

I just shook my head. My right hand was just kind of fiddling around on my stomach as I continued to build the courage to begin. I guess it was now or never as I slowly moved my hand with four fingers together straight out side by side. My middle finger made first contact with my erection as I began to push it down between my slightly parted legs. The silence in the room seemed to magnify the sound of the skin from my penis and thighs rubbing together. I closed my legs together and looked at my mother. I then pushed my hips forward and parted my legs enough for my penis to pop free, while again rubbing my thighs as it went past. She seemed to take great delight in seeing a penis used a different way for masturbating. I repeated the pushing down, hip thrusting, and popping my penis free with a slow and gradual increase in speed for my mother's viewing pleasure. I moved my left hand above my mother's left leg and thigh and let it come to rest on top of her shorts, immediately thinking about how close my hand was to her pussy. This prompted her to reach out and start to run her fingers through my hair, tilting her head with an adoring smile. She returned her gaze to my hard penis moving in between my legs. I heard a soft rush of air come out of her nose as she slowly shook her head. She must have started reminiscing, as she said "It's been a long time since I sucked a cock. Too long." My mother has never been one to mince words or avoid a topic of conversation, but sex was never one I heard her talk about until now. I was taken aback by this sudden statement, but surprised myself by continuing the dialogue.

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