Alyssa and Samantha

I first met her when I was in high school. Alyssa was my age, but it wasn't her that I was interested in. Instead, I wanted her mother. Samantha was in her late thirties and she was beautiful. She was tall, with red hair, green eyes and a voluptuous figure. Samantha instantly became the woman that I fantasized about.

I started going over to Alyssa's house three or four days a week after school. We would hang out in her room and if I were lucky enough Samantha would chat with us for a little while. After almost a month of this, one day I got out of school and headed straight to Alyssa's house, but when Samantha answered the door she told me that Alyssa had gone to her father's house that day. However, she invited me inside and the next thing I knew I was sitting on the couch. Samantha was wearing a white satin robe as she had just gotten out of the bath when I rang the door bell and she looked incredible.

As I was sitting on the couch Samantha sat on the cushion next to me, turning her body so she could face me. Her legs were crossed, causing the robe to open slightly. I couldn't help but to look at her smooth skin on the inside of her thighs. She noticed me staring at her and bluntly asked me if I though that she was sexy. I stuttered out of nervousness but answered yes. She told me that she has noticed me checking her out over the last month. She also asked me if I had seen a woman undressed before. At the age of eighteen I had not and proceeded to tell her so. Samantha then shocked me as she untied her robe and let it lay open, exposing her large breasts that were slightly covered in freckles and her hard, thick nipples. I had felt the breasts of some of the girls my age that I had made out with, but none had breasts or nipples as large as Samantha's.

I just sat there and stared at her breasts. My heart was pounding and my dick was rock hard. I had to move in my seat to adjust myself. I looked up from her breasts, into her eyes and she turned her body to face me and then spread her legs. I was so nervous I couldn't look away from her face, but she encouraged me to look at the rest of her body. I slowly looked down and was captured by the beauty between her legs. Samantha had a patch of red, curly hair shaved to be just a couple of inches wide and a few inches tall. She had no hair on the sides or underneath the opening of her pussy. Her pussy had thick lips and a distinctive bump where her clit was. At the time I had no idea what I was really looking at, but over the next few months she taught me everything that I would ever need to know.

As I sat there and stared at her body, I could feel my dick get fully hard and my boxer briefs getting soaked with pre cum. Samantha could see my enjoyment and she encouraged more as she started to rub her nipples. I watched as she rolled her nipples between her fingers, then slid one of her hands down between her legs. Her pussy had become wet and she was using three fingers to spread her wetness around on the lips of her pussy.

Samantha asked me to undress, and I did so without hesitation. I stood in front of her naked, with my hard dick pointed strait out. A bead of pre cum dripped off of my dicks head and fell to the carpet. Samantha reached over and pulled me close to her. I stood on my knees in front of her and she sat on the edge of the couch with me between her legs. She gently grabbed my dick with one hand, and pulled me closer to her with her other hand on my butt. Placing the head of my dick at her pussy, she pulled the two of us together and I was instantly as deep inside her as I could be. She was so warm, so soft and so wet. The feeling was incredible. I had no idea that being inside of a woman would feel so good. Samantha started to move her hips away from me for just a few inches, and then slid back to me, burying my dick deep within her. The feelings were too much to contain and I started to have the most intense orgasm. My young body filled her with cum.

After I came she wrapped her arms around me and buried my face between her breasts. She continued to hold me close as my dick became soft and my cum started to leak out of her pussy. She told me that we were going to have many more encounters like this one and that she was going to teach me how to pleasure a woman. Samantha then had me pull my dick out of her and complimented me on the large amount of cum that I had filled her with. I was a little embarrassed by all of this and dressed then went home.

That night I couldn't get the afternoons events off of my mind. I had images of her body and memories of the sensations that she gave me racing through my mind. I couldn't help but wonder what else Samantha was going to show me.

To be continued....

Chapter Two

It had been one week since I had returned to Samantha's house. It's not that it wasn't on my mind. I fantasized about her every night for hours as I laid in bed and pleasured my dick and my balls. I could have several orgasms at night thinking of her and I would still wake up the next morning with my balls aching for her touch. One morning I finally decided that I had to go back.

That afternoon I skipped my last class at school and rushed to her home. When I arrived, I sat in my car for a moment and caught my breath as my heart was pounding with excitement. Soon I had the courage and rang the doorbell. Just a few seconds later Samantha answered the door and my heart skipped a beat as she was wearing a sheer white robe that stopped just below her crotch.

She pulled me inside and our mouths met. Her lips were full, warm and wet. Our tongues kissed and licked each other. My instantly hard dick was pressed up against her as she held me close. I slid my young hand up to her full breasts and found that her nipples were as hard as my dick.

After a few minutes we stopped kissing, she welcomed me back and told me that she was afraid she had scared me off as I hadn't been back sooner. I told her that I was nervous to come back, but I couldn't stop thinking about our last time together. I was embarrassed, but she simply grabbed my hand and led me upstairs to the master bedroom. The walls were a deep red, and in the center of the room was a four-post bed, with sheer white fabric draped from the rails.

She led me to the edge of the bed and told me that she heard my car pull up to her house so she quickly changed into the robe and that she was going to start undressing me. She immediately pulled my T-shirt over my head and soon thereafter she had unbuttoned my jeans and pulled them down to the floor. I stood in front of her as she sat on the bed. She reached over and slid her two thumbs inside of the top of my boxer briefs. Samantha slowly pulled them, revealing my hard dick with its head covered in pre-cum.

As my boxers slid down to my ankles, she opened her mouth, placing her lips around the tip of my dick and slowly slid the first four inches of it into her mouth. Her mouth was so warm. It felt amazing as she moved her tongue and her lips up and down the shaft of my dick, all the while never leaving eye contact with me. I felt like I was going to cum. I hadn't masturbated that morning and my balls felt like they were going to explode.

Just as I was about to cum Samantha pulled my dick out of her mouth and told me that I couldn't cum yet, as the afternoon was young. I stepped out of my clothes and Samantha asked me to lie down next to her so we could talk. She told me that I couldn't tell anyone what we were doing and without a doubt I had agreed. With that she untied her sheer robe and took it off. Without another word she moved to the end of the bed and placed my throbbing, wet dick back in her mouth.

As Samantha moved her full lips up and down my dick she started rubbing my swollen balls with one hand and used her other hand to rub the shaft of my dick in front of her mouth. I couldn't hold back from the sensation for too long and soon I had filled her mouth with my cum. Samantha swallowed it and lay on top of me, kissing my mouth. I could taste and feel my warm cum on her lips and in her mouth. The taste and the sensation were amazing.

She then said that it was her turn and rolled off of me, lying on the bed next to me. She encouraged me to just lie on top of her and to suck on her nipples for a little while, allowing me to catch my breath from the enormous orgasm that I had just had. As I was on top of her I kissed and sucked on her large, firm nipples and could feel my cock growing hard once again. The feeling of her skin on my lips was incredible and soon I was kissing my way down her stomach, stopping at her patch of red pubic hair.

The curly hair above her pussy was wet with her juices, and she had a strong but sweet scent. I continued to kiss closer to the lips of her pussy, and soon I found my lips and tongue spreading her wet, swollen pussy lips. Samantha moaned as I moved my tongue around them and over them. I had no idea what I was doing but she tasted so good I wanted to lick and suck every bit of her juices.

Samantha slid her hands down from her breasts and moved them to the top of her pussy. She spread her lips with them, exposing her clit to me. I had no idea how big her clit was at the time, but after being with other women I now realize that Samantha had an enormous clitoris.

She asked me to gently suck on it, and to kiss it with my tongue. I was eager to respond and soon her clit was being kissed and massaged by my firm lips and my soft tongue. I was loving the tastes of Samantha's pussy and was getting so turned on by the sounds that she was making. As I kissed her pussy she started to rock her hips and starting moaning louder. Moaning louder still, she placed her hands on the back of my head, pulling my mouth against her pussy.

As I licked and kissed she slid her pussy up and down on my mouth, covering my mouth, chin and nose with her juices. It was the first orgasm that I had seen a woman have and I wanted to see more. As she calmed down, she pulled me up on top of her. My hard dick was again covered in pre cum and as I lied on top of her she opened her legs and pulled me close, causing my cock to slide deep into her pussy.

She asked me to move slowly in and out of her as her pussy was sensitive from her orgasm. Her pussy was so wet from the combination of my saliva and her juices. It felt so good on my cock. She helped me find a rhythm of my cock moving in and out of her and soon I was sliding my cock deep inside of her, then slipping it almost all of the way out. I loved the sensations caused by the head of my cock touching the lips of her pussy and I moved in and out of her.

As the minutes went by our breathing increased, and the pace of our fucking increased as well, but I would continue to slow down every few minutes, trying to delay my orgasm. We went on like this until Samantha grabbed my hips, holding me deep inside of her. Our pubic bones were pressed against each other and she started to gyrate her hips, causing the area just above the base of my dick to rub against her clit.

Within just a few minutes Samantha was moaning hard and I felt her orgasm. Her pussy squeezed my cock with contractions and a flood of juices covered my cock and my balls. The sensation was too much to contain and I filled her pussy with my cum. I was surprised that I had any cum left in my body after Samantha went down on me, but I squirted every last drop of cum into her.

My body was exhausted and I lied on top of her, with my head on top of her sweaty breasts. Samantha told me that she was amazed with how well I fucked her for just my second time being with a woman.

After we caught our breath we showered together. Samantha washed every inch of my body as she told me if I went home smelling of sex my parents would be suspicious. I dressed and she walked me to the front door, asking me to come back on Saturday morning as her daughter, Alyssa would be gone for the weekend at a softball tournament.

To be continued . . .