Dating Cheerleaders
Chapter 1: introductions and my first girl

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

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

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.

I was starting to like this girl more and more the longer I was with her. I decided to heck with my buddies and the barbs they may toss my way. This was a real live girl with me and she likes me. My batting average in the romance department just improved from zero to a gazillion percent. "Susie," I confessed "I don't have very much experience with girls, in fact, you're the first girl I ever kissed and I really like it." "Greg, I don't know if you noticed but I'm not exactly Miss Popularity in school. Oh, why kid myself. You're the first boy I have kissed like that and I like it too. Can we do it again?" I kissed her again and as we were sitting on the bed we leaned back and continued kissing. We were getting warmer in arousal and I started to get hard with my penis pushing against her leg through my shorts. She broke the kiss and asked "Does that thing mean you find me sexy." "Oh God," I replied "I think you are the sexiest girl I have ever met and you turn me on something fierce." I leaned over and kissed her again while I placed my hand on her breast. She jumped a little at first but did not break the kiss or pull away. On the contrary, she moaned a little and pushed her chest up against my hand.

We kissed for a while as I caressed her breast through her top with my hand. She was starting to rock her hips up and down a little showing me that she liked what I was doing. I thought I had pushed my luck and she had enough when she lifted my hand from her breast but surprised me when she slid her bikini top up and replaced my hand on her naked breast. I couldn't believe this was happening to me the science geek. I actually got to first base having my hand holding a real girls breast. As I caressed her breast I noticed that her nipple got erect and was pressing into my palm while she breathed hard and moaned. She broke the kiss and said "That feels nice. Don't stop."

Well, I did stop but taking my hand away from her breast I replaced it with my lips. I kissed her nipple and sucked on it causing her moans to increase. Kissing one breast and caressing the other was getting this girl really turned on. My level of arousal was also building up and my erection was trying to bore a hole through my shorts to gain access to that soft and warm girl that I was holding and making out with. All the while I was worshiping her breasts she was writhing and twisting around on my bed. I moved the hand that I had on her right breast down her stomach and pressed on the crotch of her suit bottoms. She spread her legs giving me more room to explore her treasures. As I stroked her on the outside of her bottoms she slid her hand over to me and took hold of my erection through my suit bottom. I thought I was going to lose it right then but fought it off.

She was moaning constantly by then and softly whispered in my ear "Touch me inside." So I worked my fingers under the waistband of her suit and down to the split of her sex. She thrust her hips up and down as I stroked my finger through the valley of her slit. While we were doing that she tightened her grip on my penis and started stroking up and down it's length. She reached inside my waistband and took hold of my bare throbbing erection and kept stroking it. I was keeping up a rhythmic caressing of her slit as she spread her legs more to give me better access. I found the little bump at the top and when I did she jumped and let out a little squeak followed by moaning. Her pelvis did not stop the rocking motion as I rubbed her from the bottom to the top of her pubic slit. Her legs were then open enough that I was able to touch her opening at the bottom.

I broke contact with her lower regions to pull my shorts down freeing my painful erection. While I did that she pulled her bottoms completely off allowing me full access to her charms. I resumed my exploration of her by inserting a finger into her hot and moist opening. She was also stroking my rod faster and getting me right to the edge of erupting. When I inserted my finger deeper into her tunnel of love I rubbed my thumb around her bump causing her to get very animated in her arousal. She was getting so hectic I could sense that something was about to happen. I also was teetering on the edge of explosion when her body stiffened like a board and she let out a scream. That set me off and I started to shoot my essence all over her legs and stomach.

Once both of our orgasms waned and we came back to earth she said "Oh Greg, I've never felt anything like that before. It was so good it was awesome." I replied "Susie, you have made me feel better than I could ever imagine." I was feeling pretty good about myself since I had actually made a girl come and she was not going to slug me and run away. I slowly got up and got a wet wash cloth from the bathroom and cleaned up my mess from her body and mine. While cleaning I realized that I was looking at a mostly naked girl up close and I loved what I saw. She looked so much better than any old magazine. She also spent some time examining my penis with fascination. We put our suits back on and after a long tender kiss made our way back out to the pool. As we got there my sister noticed that Susie had that glow about her and gave me that sisterly knowing smile that said "I know what you did."

Chapter 2 ยป

Story tagged with:
mt/ft / Consensual / Heterosexual / First / Safe Sex / Masturbation / Petting /