Dating Cheerleaders - Cover

Dating Cheerleaders

Copyright© 2012 by Stepdad

Chapter 1: introductions and my first girl

Romantic Sex Story: Chapter 1: introductions and my first girl - Greg's big sister helps him learn how to date girls and specifically cheerleaders.

Caution: This Romantic Sex Story contains strong sexual content, including mt/ft   Consensual   Heterosexual   First   Safe Sex   Masturbation   Petting  

Please allow me to introduce myself. My name is Gregory Thomas. I am 16 years old and a junior at Cloverdale High School. I am kind of a loner when it comes to dating since I lack the courage to ask a girl out on a date. Every time I try I get tongue-tied and just embarrass myself. I therefore end up spending my weekends playing computer games or reading. What do I read? The same thing most teenage boys read; Playboy of course. Since I jack off two or three times a day that book comes in really handy. I guess I am destined to stay single and a virgin the rest of my life.

I have an older sister, Tracy, who is 17 and a senior at the same school. Tracy is very popular and dates cool guys every weekend. She is on the varsity cheerleading squad which keeps her body toned to perfection. This is noticed by every boy in school and did I forget to mention that she is also drop-dead gorgeous which helps her social life immensely. Her long blonde hair and radiant blue eyes don't hurt matters at all either. Even though she is my sister I find myself lusting after her in a big way. I would give my right nut to get to have sex with her so quite often she is the subject of my wanking fantasies. Sometimes I would see her dashing from the shower to her room wrapped in an all too short towel so I would catch fleeting glimpses of her charms. That would give me an erection which demanded immediate attention. Once when she didn't know I was home I caught her sunbathing topless on the patio. Instant pocket of wood time.

Our house was in a nice quiet neighborhood not far from the high school that we both attended. We had a pool and a hot tub that we enjoyed quite a lot. Many times Tracy and I would walk home together with me carrying her books. To the casual observer who didn't know us we would appear like girlfriend and boyfriend. The illusion was further enhanced since we enjoyed doing things and going places together. We had a very close relationship and helped each other whenever needed. I helped her with her math and science homework and she helped me with my English and social studies.

One Saturday Tracy invited her cheerleader squad over to our house for a pool party. Mom had told her that she would be responsible for buying the refreshments and cleaning up after the party. I told Tracy that if she would let me be there I would help her out with the party arrangements. Now, Actually I had an ulterior motive since I would be the only male surrounded by sixteen gorgeous girls in bikinis. But to Tracy I led her to believe I was just being helpful to her. She said that would be fine. I had been a definite loser when it came to dating girls from school. I couldn't seem to get a date if my life depended on it.

At the party, as I was grilling burgers and fetching soft drinks, I noticed one girl, Susie Jenkins, watching me very closely. I hadn't paid much attention to her since she was only 14 and a freshman. I mean she is pretty, had a killer body and all that but I would catch a ration of flack from my buddies if I showed any interest in a girl two years younger than me. They would accuse me of robbing the cradle and digs of that sort. Tracy noticed Susie giving me the eye and came over to me and asked "Why don't you go talk with Susie. She seems interested in you." I gave Tracy all the arguments against it and she said "Greg, she's a cute girl who's interested in you and I hear she likes you. Your track record this year with girls sucks so go over there and talk with her. What can it hurt?" Ok, so Tracy convinced me to give it a try. I walked over to Susie and said "Hi." She replied "Hi yourself." The ice was officially broken so I started a conversation with her about school, a subject we had in common. Well it turned out that we had something specific to talk about. She was taking a science class but was having trouble keeping track of the different parts that make up matter. I sat down with her and we discussed the parts of an atom and what they do. I described some of the common atoms which made up the elements.

Our discussion was getting a little deep for poolside so I asked her if she would like to go to my room and look in my chemistry book for some of her answers. She said "Sure, I'd like that." So we headed into the house to my room. Now, I was a kind of a science geek and had drawings of atoms and periodic tables on the wall as decorations. I used these charts to get her started in understanding the structure of matter. With her head nodding and her occasional "Uh huh" it appeared she was getting it. After a bit I noticed she was looking at me and not the charts. I was getting a little self-conscious and started to bumble some of the words.

That was when she put her hand on my cheek turned my head to face her and kissed me on the lips. Wow, I thought my head was going to explode. That was an honest to goodness real girl and she just kissed me. I didn't know what to do next so I winged it and kissed her back. We held that kiss for what seemed an hour but more realistically was only a few seconds. Trying to act the suave debonair world traveler I came up with the romantic masterpiece of "I like you Susie." Ok, so I'm no Shakespeare but it was all I could think of at the time. It must have been the right thing to say because she countered with "I like you too Greg, and have all year." Oh boy, What now? Do I kiss her again, hold her hand, hug her or run away. I was tempted to run since I was scared silly and shaking like a leaf but I got a grip on myself and decided to hug and kiss her instead. That kiss lasted considerably longer than the first one and seemed to have an effect on us since we were both breathing harder than normal.

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