This a true story of secrecy, sexual exploration, and obsession.
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This story took place during my senior year in high school 2011. Trying to be popular in high school was an everyday job. With a rather small class it was hard to impress the very few attractive women in my grade. Playing sports was the main opportunity to attract some attention. What girl doesn't like a muscular boy who is good at sports? The problem was I wasn't very muscular and I wasn't as good at sports as some other boys in my class. I attracted a few girls attention but none that I was interested in.
Life in high school was different for me than it is for most people. Even though I love high school and made some great friends, there was a certain kind of pressure to try and act cool. I would say I acted different in high school than I did at home. For instance most conversations consisted of sex and women. Whether they were women in our class or just hot women we knew or had seen.
In a class with only 85 students I had about four girls that were hot. Only one had a boyfriend and she was the hottest. Most of my friends had lost their virginity by senior year and I felt the pressure to do the same since I was 19 and most of my friends were 18. I often lied about my virginity when people asked me because I didn't want to be made fun of. I felt somewhat pathetic masturbating at home when I should be with my girlfriend having fun. Problem was I didn't have a girlfriend.
With the chances of dating one of the few attractive girls in my grade looking slim, I turned to girls in the grade below me. As I went through puberty my sexual attractions changed often. When it came to masturbation material I found new exciting things weekly. My first attraction was younger girls meaning girls in my grade. As I became more nervous about losing my virginity I became interested in older women. I call them Milfs but any way you call them I was attracted to Moms. Something about an experienced older woman with a big set of breasts really turned me on.
My attraction for Milfs still remains but now I was becoming interested in chubby women. Not just older chubby women but women my age who are chubby. In my opinion fat and chubby are two different things. Fat is too big and chubby is slightly overweight but still attractive. In high school most boys tried to avoid those girls and were often overlooked because of their size. As I realized this I found a loophole in the system that I could capitalize on.
One day at lunch I spotted my target. Looking back I wouldn't call her a target but that's how I felt at the time. Her name was Rachael. She was an 18 year old junior who was very beautiful. At about 5 foot 5 she was gorgeous. She had very big breasts for her age and had a great ass. Her only flaw was that she was chubby, borderline fat but still attractive in my eyes. As to my knowledge she has never had a boyfriend but it is a very nice girl.
I knew I must pursue Rachael in secrecy because I knew my friends would tear me apart with the jokes. I couldn't talk to Rachael at school so I would often pursue her after volleyball games. No one in my grade was interested in watching junior varsity volleyball games so I knew it would be safe. After the games I would often talk with her about the game and about school. I was very good at talking to girls and before you knew it we were becoming good friends.
One day after one of her volleyball games we were casually talking and she asked me if I wanted to exchange cell phone numbers. I agreed and our conversations continued long into the evenings. I knew my chances of being discovered by my friends grew so I made up a lie to tell her that we couldn't talk during school hours. I think I told her coaches didn't want us to have girlfriends and she fell for it.
As our relationship grew I could tell she was becoming very attracted to me. Our conversations gradually became more sexual. As we explored each other's sexual experiences I was shocked to find out she has had sex before. I was even more surprised to hear she had sex with a boy in my grade. He was a real loser. A not very intelligent, overweight kid who thought he was a bad ass because he smoked and hung out with the wrong crowd. I was very curious about their sexual encounter and found out he had a small penis. I found that very funny.
We often played truth or dare over the phone. She would often ask how big my penis was but I would try to change the subject to make her anxious and horny. Truth is I had no idea if my dick was big or not. My penis is 6.5 inches erect and I figured it was somewhat big but wasn't sure since I haven't seen other boys erections in the showers. I lead her on to believe I've received a blowjob but really haven't. I would proceed to ask her if she would spit or swallow after a blowjob. To my surprise she said swallow. I became very aroused during our conversations and I would often masturbate during them.
Our ambition grew and one day I dared her to send my pictures of her naked body. She was hesitant at first but I told her I would send a picture of me naked in return. She gave in and agreed to try sexting. The first picture I received was of her big boobs. They were quite large and sagged slightly. Her nipples were quite big as well. My interest in chubby women grew from that picture. I loved large boobs and hers were amazing. I wanted nothing more than to squeeze them right then and there. I persuaded her to send more and she continued. The next one was a close up of her vagina. I've only seen pictures of vaginas on the internet so didn't know much about them but hers was very attractive. It looked very tight and had a slight pinkish color too it. It appeared she hadn't shaved for a while but that turned me on even more.
After she sent two pictures of herself she wanted one from me. I became very nervous and tried to find a way out if it. I apologized and said I had to go eat but would do it another time. The next day at school I stared at her the whole time during lunch fantasizing about her body. I felt somewhat awkward when we made eye contact when she quickly looked away.
Later that night I started off by texting her first. We continued with small talk then I asked her if she could send me a picture of her ass. She agreed but only if I would send her a picture right after. I sucked up my fear and said ok. The picture I arrived and instant erection. She was wearing a very sexy pink thong that sank deep into her ass crack. Her large ass was amazing, perfect shape, perfect size. She was bent over slightly so I could see her beautiful mound between her thick, sexy thighs. I often wondered if I fucked her in the ass, if my dick could reach to her ass hole.
I now knew it was my turn to send a picture. She wanted one of a bare skin erection. I didn't want to send a bare skin picture in case she showed it to other people. In a way I wanted her to show other people but I was still nervous. I was still wearing my compression shorts so I decided I would take a picture while wearing those. Compression shorts are pretty much very tight underwear. Very easy to see the outline of a penis. I got a semi hard on which was basically an erection that could face downward between by legs. The picture turned out great. My penis was easily visible and it still looked big. I sent it and waited for a response.
"HOLY CRAP THAT'S HUGE", was the reply I received. I laughed and replied "what do you think"?
"That is one big penis, very sexy"
I was very flattered to hear that. Now I knew that my penis was big. A girl with sexual experience said I had a big penis. I now wanted to fuck this girl more than anything in the world.
Immediately after sending the picture I asked her if she wanted to hang out this weekend. My parents were going to football game with their friends and would gone Saturday and Sunday. My original plan was to have a bunch of friends over to drink and watch the game but have Rachael come over sounded a lot better.
