Chapter 9 - A Young Cuckold’s First time

“Hello everyone, my name is Scott and I am nineteen years old. Last year I started seeing an older woman in her forties and things escaladed from there into a full on relationship. Anna, that is her name, is or I should say was one of my mother’s best friends. My mother no longer speaks to either one of us because of our relationship.” Scott was sharing with the rest of the cuckolds in the room his first time. He continued his story…

Before I had met Anna, I hadn’t had a girlfriend nor had I had sex with anyone. I was still a virgin. Anna had taken my virginity. I was so inexperienced and she had years of experience on me that I was grateful that an older beautiful woman would find any interest in me.

Anna was best friends with my mother since before I was born. She would come over to our house all the time, especially after my parents divorced when I was eleven years old. When I was a teenager I started to notice girls, but for some reason, I had always found Anna very attractive. She had long blond hair, a perfect complexion, long legs, a tight ass and a rack on her chest that would catch my gaze for hours. She always wore pink lipstick and had her fingernails and toenails perfectly manicured with pink nail polish.

I remembered in the summer time when she would come over to lay out by our pool with my mom and her friends in her two piece bikini. All the other women would wear one pieces, but not Anna. She had never been married or had any children, so she had a perfect figure for a two piece bikini. I would stare at her lying on the chaise lounge chair from my bedroom window, which was on the second floor of our house.

I would fantasize that she would ask me to rub suntan oil all over her body. This would cause me to become erect when I was younger and was starting to masturbate. I had stroked my cock to so many fantasies involving Anna that my cock soon became raw and sore throughout my younger teenage years.

On my eighteenth birthday, my mom threw a pool party with all my friends and family and Anna was there also. She got a lot of stares from my friends and a lot of envious looks from the girls I had invited from my school. The party was a blast and my mom had bought us all wine coolers to celebrate with.

I was sitting on a chaise lounge chair when Anna came up to me. I was sipping my wine cooler and she had some sort of mixed drink my mom was serving the legal adults at the party.

“So, today you are a man.” Anna sat next to me and smiled. She placed her perfectly manicured hand on my thigh and rubbed it. “I do have a birthday present for you later on tonight.” She whispered and kissed my cheek. “Happy Birthday handsome.” Then she got up and walked away. I watched as her ass bounced in her bikini bottom as she walked away.

As I wondered what she could possibly want to give me for my birthday that night, my cock began to grow and ache. Every fantasy that I had ever had of her swirled through my mind and made me light-headed. I had to wait awhile before I could stand. Eventually, I got up and jumped into the pool to cool off.

Later that night, after everyone had left, Anna stayed and helped my mother clean up the party mess. Anna was going to stay in the guest room that night because she had too much to drink. My mom took a shower and then passed out because she had drunk too much alcohol as well. Everyone else had gone for the night.

I was in my room and had just stepped out of the shower and was drying my hair off with my towel. I had the other towel wrapped around my waist. I was startled to see Anna lying on my bed completely naked.

“Hello there birthday boy.” She said in a very sultry voice.

I stood frozen for a moment. Was this actually happening? I mean I had fantasized about things like this for years now. Did I have too much to drink and I was in some sort of drunken stupor passed out dreaming this? I wanted to pinch myself just to make sure.

“Well, are you going to stand there all night starring at me or are you going to come over here and enjoy your best birthday present ever?” She asked me.

I walked over to the bed and laid down next to her. I felt her warm naked body press against mine as she began to kiss me passionately. My cock was so hard it was throbbing and aching. Her skin was so soft.

“Looks like someone is excited.” Anna said with a smile on her face.

“Anna…” I began.

“Yes?” She replied.

“I’m a virgin. I’ve never had sex with anyone before.” I told her. I didn’t want there to be any misconceptions about my sexual experience. “I know.” She said.

She knew? But… how? I wondered to myself.

Anna then went down in between my legs and began to kiss my cock. I thought I was going to orgasm right then and there. “I am going to make you cum first so that you won’t cum so fast when you are fucking me.” Anna said as she wrapped her lips around my cock.

I closed my eyes as I felt her lips begin to suck on my cock. It felt amazingly good. I’ve had my cock sucked before at a party, but I was so drunk, I don’t remember much about it. And it wasn’t really all that good of what I remembered.

You can read the rest of this story from any of the major book sellers, or also at http://www.vincestead.com or http://www.fun2readbooks.com