I recently read a story from an old friend, Papatoad, and it gave me this crazy idea for a similar one. Thanks to my anonymous friend for editing my story.
My name is Gary and I come from a wealthy family. As an only child, I spent a lot of time alone. Even though I was never outgoing, I was rather smart. By the time I was in high school, my life had never changed much. I liked a few girls but I never dated. My dad said girls would probably only want me because they knew our family was wealthy.
I never played sports. Instead, I joined a gym. At five foot ten, I had been on the slim side, but soon bulked up from working out all the time. I also took classes for self-protection since I was picked on a lot. The fights didn't last long once I knew what I was doing.
I started college and ended up rooming with a geek. We got along fine because we were both quiet and shy. I didn't even go to a party till my sophomore year. I drank a little and it loosened me up some. A girl who was really drunk asked if I wanted to go to her room. She began to take off her clothes so I did the same.
She reached in her drawer for a condom and I slipped it on. We kissed a couple of times before she fell onto the bed, pulling me with her. I slowly pushed my cock into her. It was the first time I had ever had sex. I pumped and pumped until I was ready to come. She screamed as she had an orgasm, and I came soon after.
I pulled out, took off the condom, and dropped it into her trashcan. She thanked me for coming over, turned her back to me, and went to sleep. I got dressed and went back to my room. I lost my virginity to a girl I didn't even know. It felt good but not much better than masturbating.
I went to a couple more parties and the sex was similar. I knew I wasn't that good of a lover. My junior year I dated a couple of times but my dates always said something about my family being wealthy. I figured that's why they dated me. They wanted me to spend a lot of money on them. So I decided to put more and more time into my studies. I majored in accounting and planned to join my dad's firm after I graduated.
During my senior year, I dated a couple of girls but we just weren't compatible. I still had sex with them but I didn't seem to improve much. Then just before graduation, I met Sheila. She was the nicest and prettiest girl I had ever seen. I remembered her from school events and activities and heard she dated a lot. It didn't take long before I was somewhat infatuated with her.
She was in a couple of my classes and we talked a little most every day. I knew I was slowly falling for her and one day picked up enough courage to ask her out to lunch. She smiled at me and accepted. We went over to the neighborhood restaurant, ordered lunch, and talked for an hour. She was so nice to be with.
I learned she lived with her parents and drove to school every day. Since I was from a small town on the other side of the state, I lived in the dorm. Before we left the restaurant, I asked if she wanted to go out that weekend but she said she already had plans. We agreed to go out the following weekend instead.
I knew she dated a lot. She was really popular yet I couldn't help liking her, borderline loving her. She never seemed to go with anyone steady or on a regular basis. I remember her telling me that she just wanted to play the field until she decided to settle down with one guy.
I asked her what she wanted to do on our date and she mentioned going out to dinner and then seeing an IMAX movie. Those were the movies on a really big screen. So that was what we did.
We started going out fairly regularly. There was really nothing special about me but she usually said yes when I asked her out. She knew I came from money but never talked about it. She told me she lived with her sister, Darla. I did ask her why she dated me and she told me it was because of my shyness and she didn't have to fight me all night long because I acted like a gentleman.
All we ever did was a light peck on the lips at the end of the night. I just wasn't a good lover and not sure what to do. After our fifth date, Sheila invited me into her apartment. Her sister wasn't home at the time. Even though they shared the apartment, they each had their own bedroom. Sheila invited me into hers and after she closed the door, she kissed me.
She put her hands on my cheeks and kissed me very softly. I think the first time I still had my eyes open. After that first kiss, she kept kissing me and telling me how much she loved kisses. We ended up sitting on the bed, kissing very passionately. I knew I had found love.
Then she stood up and slowly took off all her clothes. She was so beautiful. I looked at her face as she unbuttoned and removed my shirt. Next she undid my belt and zipper so my pants fell to the floor. All I had on was my briefs and she slowly pushed them down until they landed on my feet. I know that I was hard and stiff as a rock and it put a smile on her face.
We got in the bed and I was going to fuck her the only way I knew how but she stopped me. She had me put my face on her trimmed muff. I did and I couldn't help kissing her down there. I had never done it before but the smell of her wetness was intoxicating. I found myself kissing and sucking her pussy as hard as I could until I felt her climax.
I climbed back up on the bed and kissed her with my face full of her juices. I rubbed her tits and she told me to be very gentle with them. My cock was rock hard. I had never had sex like this with any woman. Sheila said she was going to show me how she loved sex. She told me she was on the pill and that I didn't need condoms, something I had never done.
I got between her legs and she had me rub my cock back and forth across her pussy opening. God, it felt so good. I then slowly pushed the head of my cock into her and she was making all kind of noises. I shoved my whole cock into her and began to fuck her in earnest. She held her legs up so I could thrust harder. I heard her scream out and I came a few seconds later. It was the biggest orgasm I ever had.
I lay there on top of her sweating from all the sex. I was holding myself up on my hand so I didn't squash her. After her pussy stopped pulsating, I rolled off her. She leaned over and gave me a long passionate kiss. Then she grabbed some tissues off the nightstand, put them between her legs, and ran for the bathroom. I grabbed a few tissues and wiped off my cock.
I heard the water running and imagined Sheila in the shower. While she was in there, I cleaned up and dressed. After she came out, we kissed and I told her that I thought I was falling in love with her. She kissed me again and said she was falling for me too.
We started dating regularly. She taught me so many sexual things. I loved her and I knew I would do anything for her. I asked her if she would marry me after our graduation and she said yes. We both graduated the same day. I got my degree in accounting and of course went to work for my dad.
Sheila got a degree in Business Management and got a job at a real estate agency. We started planning our wedding and married three months later. Sheila looked like an angel walking down the aisle. I was so happy, tears gathered in my eyes.
We took a three-day cruise to the Bahamas and spent most of our time making love. Sheila was the best lover I ever had. I knew she learned it from other guys before me but I didn't care. She now belonged to me. I was obsessed with her and would do whatever I had to in order to keep her.
Life for us was great. We really didn't want for anything. My job kept me busy and Sheila liked selling real estate. Neither of us wanted to start a family yet. I just wanted Sheila.
