For Once I Win

Hello this is a story I would like to share with all of you. My name is Richard and I am what you would call a dork. I am 5'10 and 177 pounds, as you have guessed I am kind of fat. School was always the same thing, people would laugh at me and call me names, I don't blame them though, after all I was a 18 year old virgin. This is my story of how I went from loser to winner in one single night.

It all started back in November, school was boring and everyone hated going like all teenagers do, but on Tuesday something totally unexpected happened. I found a note from Rachel Thomas in my locker. It read: "hey richie, I am failing my English class and I heard you were good at English so I was wondering if tonight you could tutor me, please! I am desperate!" So when we were at lunch and I saw her I told her that she could come over to my house tonight and I would help her. She simply ignored me and ate her lunch so I said fine and walked away. After the fourth period class she caught up with me in the hallway and said "richie I'm sorry, I didn't want everyone to know I needed help with my English and make me feel stupid" so being soft hearted I told her it was OK.

That night she came over my house at 8:00, my mother was off at the movies with her new boyfriend so we had the house to ourselves. We worked on her English homework first and then we got tired so we decided to watch some TV. At around 10:00 my mother and her boyfriend came home so Rachel and I went to my room and talked a bit.

"Hey Richie?" She mumbled.

"What?" I asked.

"I was wondering why you never seem to associate with anyone, you always kind of keep to yourself." She admitted.

"I don't know, I just figure no one wants to talk to me." I said, kicking myself for saying something so stupid.

"I like talking to you." She said as she put her hand on mine.

"Um.. Well, that's cool I guess." I blurted.

"Richie? Do you think I'm sexy?" She asked.

"Um.. Yes, I do I think you are very sexy." I said in shock.

"Would you like to see me naked?" She asked, shocking me to death.

"I guess, if you would like to show me." I mumbled.

With that she stood up and took off her shirt. She was wearing a black lacy bra that encased her perfect 34C tits. I started to feel a little pain as my 6 inch dick began to push itself against my jeans. I watched her as she removed her jeans and revealed a pair of black panties to match her bra. I was in heaven all I could think about was touching her. She stood before me a 5'5 109 pound woman with great tits and a nice ass. She asked if I would like for her to remove her bra and panties. "Yes!" I said a little to enthusiastically. Then she removed her bra and panties and I died in my sit. She was so gorgeous and she was naked in my room. "You have gotten a little bump in your jeans." She noted. "Maybe you should take them off." She continued. So I got up and took off my shirt and jeans leaving me in my stupid blue briefs. She smiled as she noticed my little dick sticking straight up in my underwear. "Why don't you take those off also?" She boldly added. Quickly fumbling with my underwear I got totally naked in front of this beautiful woman. I was a bit shy because I wasn't a hard body but I felt safe with Rachel. She asked me if I would like a kiss and I nodded that I would. She then came over to me and kissed me on my lips very softly. "Did you like it?" She asked.

"It was like a snowflake landing on my lips" I said like a total idiot.

"Would you like another kiss?" She asked.

It was like music to my tone deaf ears. So I said that I would and she came over and we shared a very deep passionate kiss. You all may laugh at me, but that night was the first time I had ever french kissed anyone. I knew this all had to be a dream. I put my hand on her left breast as we kissed and I felt her nipples grow hard between my fingers. This was perfect, she was perfect and I was with her. When we broke our kiss she asked me the most horrible question.

"Richie? I was wondering, um. Are you a virgin?" She asked, killing me inside.

"Yes." I replied in my quietest tone.

"That is so sweet!" She said with a huge smile on her face.

"Are you?" I boldly asked.

"No. I had sex with David Simmon last year when we dated." She admitted.

"But! I didn't enjoy it. He was a moron and couldn't please a woman if his life depended on it." She quickly added.

"Oh well, Guys don't get a manual on how to please women at birth ya know?" I said a little defensively.

"I know, that's why I am going to teach you everything you need to know." She said.

"You're going to what?" I yelled in total shock.

"I'm going to teach you how to please a woman, if you would like me to that is." She said with a nervous tone in her voice.

"You're serious? You want to teach me how to have sex?" I asked, a little confused.

"Yes! I would really like to show you how to please a woman." She said, sounding a little annoyed.

Feeling a little bold I reached over and grabbed her waist and kissed her deeply. I felt her hand wrap around my dick and she started to jerk me off. I came in seconds, I felt so embarrassed I almost started crying. She held me in her arms and ran her fingers through my hair and told me everything was OK. "Lay down and I'll get you ready." She said. So I laid down with my legs hanging half way off the bed and she got in between my legs and started licking up my thighs. Then I lifted my head to watch as she took my nuts into her mouth, I could feel her tongue gently rub against my nut sack. Then to my delight she licked the head of my dick and took it into her mouth, it felt so good as her warm wet mouth sucked and stroked up and down on my semi-hard dick. Once my dick was as hard as it could be she climbed on top of me and guided her wet pussy down onto my hard cock. As I entered her I held my breathe, it was pleasure I had never known before. She rode me for a few minutes and I sucked on her sweet nipples. "Do you like my tits?" She asked.

"Hell yeah!" I blurted in excitement.

"Well I'll lay down and you can tit fuck me?" She asked.

"Tit fuck you?" I asked.

"Yes, I'll lay down and you put your dick in between my tits, and I squeeze them together and you hump my chest." She explained. So I climbed on top of her and stuck my dick between her tits, she squeezed them together and I started humping as fast as I could. It felt so good I knew I wouldn't last much longer so I started slowing down.

"Just cum on me honey!" She yelled. So I started to quicken my pace, humping her chest as fast as I could until I felt my balls tighten.

"I'm going to cum!" I screamed. She smiled at me as I saw my white semen splash against her neck and chin. After that I fell on top of her and kissed her.

The next thing I remember was my mother coming in the room and waking me up. "It was all a dream." I said, kind of pissed. "The best night of my life never even happened!" I started to yell. That morning I took longer then ever to get ready for school. I hated life for teasing me with my desires and then taking them all away from me. That morning at school I didn't pay attention to anyone, not my teachers or even people that would crack jokes at me. I went to gym class and after changing in the locker room I walked onto the track, I started to walk around it to get my credit for 'running' the mile. When David (Rachel's EX) came over and pushed me onto the grass, "ha ha You can't even walk right can you fatass." He snickered. After David and his group of slackers walked away I got up and walked back towards the gym. That's when it happened, Rachel came over and hugged me and with a big kiss said "hey honey, last night was great! We'll do it again tonight if you want." I remember asking myself if this was just another dream, another way of life tormenting me with my desires. I kissed her again and said to myself "Nah! My dreams could never be this good."

To wrap things up I will tell you this, Rachel and I have been married for 5 years. We have a beautiful son and a sex life you would never believe. David is the gym teacher at our old school and has been married and divorced in the past year. I was the loser, I admit that but now I am the winner, that's the irony of it all. That is life itself.