A Guilty Pleasure

About 20 something years ago, my Mother worked her fingers to the bone at small diners as a waitress for as long as I can remember. The last place we lived was next to a slightly bigger facility and built right next to a major highway which meant a constant stream of customers day or night. She was always there or so it seemed, and I was usually at school until the afternoon. Needless to say I spent a lot of time alone. I had no siblings and my Dad hadn't been heard from since I was a toddler. My Mother and I had to fend for ourselves and that meant the household chores were my responsibility while she brought home the paychecks.

I took care of the cleaning, laundry and other chores since I was about 12. We had moved into the area and stayed there for the last 6 or so years and we liked it. It was a nice little town and we got along great with everyone. Mom fit in perfectly at this diner and the customers treated the both of us very well. The Only problem was due to the long shifts, my poor Mother used to come home completely exhausted. She was a dainty thing but always seemed to have lots of energy. I always felt so sorry for her when she finally came home. She would be completely wiped out from moving about serving others all day long.

We had a nightly ritual to where I would prepare her dinner, catch a little T.V. and prepare her for bed. My favorite part was a guilty pleasure of mine and I always liked doing it for her and I had done it for years. As a waitress, Mom wore the typical uniform. A blouse with the diner's logo on it, an above the knee skirt with apron, neutral colored pantyhose, and non slip pumps with a short heel. Every night when Mom came home, she would plop down in the bed or couch and I removed her shoes exposing her petite, sometimes sweaty nylon encased feet. She loved when I massaged them and so did I. I had a pretty good technique and My Mom would squirm and coo with delight as I rubbed her silky heels, toes, ankles, and calves.

I had a real affinity for hosiery back then and I still do. I couldn't wait for her to come home, kick those heels off and let me have my way with her stocking feet. The best part was when she was really burnt out, she would let me remove her pantyhose completely. I was now a lonely 18 year old boy and admittedly, I got a small thrill from reaching up her skirt, searching for her waistband and pulling her nylons completely down and off. I tried not to look "up there" as I did this, but sometimes curiosity would get the best of me and I would steal an awkward glimpse of her woman parts. She always wore these really dark, sun-tan, colored hose. They were a bit thicker for support I guess but I loved the way the light glistened off her legs and feet with that sexy sheen.

I was almost 19 at the time and one night we were about to begin our nightly ritual as usual. I wasn't into it and Mom could tell. I was a little depressed not having known the touch of another woman yet. this went on a few more nights where I just removed her shoes and tucked her into bed. I was devoting too much time to studies, chores, our financial situation, and looking for my own job to have any kind of life for myself. Mom could tell I was in a funk and finally confronted me about it.

I sat at the foot of the bed, and began to caress her soft feet per usual. "alright, I can tell something is up...spill it" Mom said. I looked up at her and told her about my longing to be with a girl in a serious relationship and the lack there of. I began a 15 minute long speech about how lonely I was and the fact that I was almost 19 and still a virgin. "it's not your fault ." I said. "I have always just wondered what it felt like". I could see that she was sympathetic to my plight. Just then, she sat up and said " I can tell you exactly what it's like."

with that, Mom went into a long spiel about how wonderful sex felt. She explained in great detail about positions, and how she used to do it all the time in her youth. As she waxed nostalgic, she had a huge smile on her face as if I had uncorked a flood of repressed memories. She squirmed and shifted as she talked on and on about doing the deed as I massaged her legs and ankles. I was fascinated and a little freaked out hearing this from my own Mother. I then noticed that I was getting greatly aroused by Mom's sex talk and started stroking her feet and legs with great fervor.. and she did too.

Mom began to blush as she clearly saw the state of my shorts getting tighter and a visible outline of my gradually stiffening length. She began to blush and lay flat on the bed. "take my pantyhose off, I want to show you something. Mom said. I was a bit apprehensive and followed orders. I reached up her skirt and yanked her hose down. As I did this, Mom was hiking her skirt upward. By the time I finished peeling the moist hosiery from the ends of her toes, I looked up to see my Mom's lower half completely exposed. I tried to quickly shy away but Mom grabbed my hand. "No no, I want you to see" she said calmly.

I was stunned. I couldn't get myself to look away. I had never seen a vagina up close before. Mom pulled me closer as she smiled. She could tell I was in awe. I just stared at it, then into it. I was mezmorized. Mom started to poke at it a little to let me see all sides and angles. "Do you want to touch it?" she said. I said nothing and began to reach my hand out toward it. I hesitated and a billion thoughts started a stampede in my head about how wrong, and odd this was. Mom chuckled "it's okay...Go ahead!" I placed my fingers on the sides of it. It felt warm, moist, and a bit fuzzy. Instinctively I started to swirl my finger between the dainty lips. Mom cooed aloud. I didn't know what to do next. I gently inserted my fingertip inside the contraption. "yeah, that's right." Mom said softly. I made a few more quick insertions and Mom moaned in unison.

I was rock hard at this point. I got up the courage and shoved my finger in her increasingly moist hole all the way and she sighed in agreement. It was too late to turn back now. As I repeatedly prodded my Mother's opening, I began to paw at my groin finally releasing my length from my shorts. Mom was delighted. She looked at my rigid pole and began to smile. "Do you want to?" she quipped. I looked at her kind of puzzled. "Do you want to try it?" she said. I thought she was joking but asked a third time. My head felt like it was going to explode. I knew it was wrong to put my cock into my own mother but at the same time I had never been so turned on in my life. I was frozen.

Mom put one hand on my shoulder and spread her legs apart. This was it! Finally, my urges got the best of me and I started toward her open legs with myself in my hand. I swirled the end of my cock around the softest part of the opening. I could see the look of anticipation on Mom's face. I inserted the entire head inside, and it felt wonderful. I immediately pushed the rest of myself into her warm snatch. Mom gasped aloud. I just held it there for a few seconds taking in the sensation. I remember thinking that her body temperature was much higher from the inside and I could feel her every heartbeat. I retracted my length all the way out and began to repeat the process over and over, a little faster each time.

Mom bucked wildly as we fucked and I could tell that she hadn't felt this sensation in a while either. I held both of her creamy little thighs in my hands as my lower half slammed into hers. A part of me couldn't believe what was happening, but an even smaller part of me wasn't that surprised. I spent years touching this woman in areas and ways that only a lover should. This felt incredible! Mom was moaning uncontrollably which started to turn me on even more and I started fucking her harder. Mom's pussy began to relax and accept my shaft inside of her causing her to become wetter and wetter with every thrust. Now I grabbed her ass from under her off the bed and began to pound her opening without mercy. We were both panting, gasping, and moaning at deafening levels. I looked down to see my entire cock was being enveloped by my Mother's pretty pink vagina. I kept pushing my rod deeper with every thrust. The only sounds I could hear was the noise of wet skin slapping together. Mom's back was arched as I pulled her closer so she couldn't get away. I held her legs together straight up in the air and I began to lick her toes as we fucked. This sent her into overdrive and made her cunt tighten up around my undulating stiffness.

After about 20 minutes of hard fucking we could couldn't take it anymore and it was time to release. I started to panic as how to finish but remembered that Mom wasn't able to become pregnant, hence, my being an only child. With a few final grunts and deep thrusts, I released a deluge of my wad into the deepest chasms of my Mother's cavity. Mom howled in absolute delight as she had reached orgasm. Her body slowly came back down on the bed. I retracted my softening rod which was followed by a trail of slimy white goo. It seemed to seep out of her puffy red snatch endlessly. We were both amazed at the sensation we had both just experienced. Mom's release was pent up for years, and mine was nonexistent until now.

We didn't say much after we just smiled and enjoyed the feeling of such a bonding moment. I curled up next to her in her bed and we both just fell asleep a little later. This moment had given me the confidence and motivation to seek other relationships with what would be more girlfriends to come. Of course we never told them of this incident and we never really spoke of it again afterwards. I was completely grateful.