Toby Goes from Rages to Riches

by Butch

11 Sep 2019 3125 readers Score 8.9 (100 votes) PDF Mobi ePub Txt


I'm Toby and I'm 18 years old 5'8" tall, 160 lbs, dark black hair, hazel eyes and a 29" waist. My body is smooth and I'm clean shaved.

I come from a disfunctional family as both of my parents are heavily into drugs and that is where most of the money goes. My dad has low end jobs and gets fired from most of them. My Mom doesn't work as she is strung out most of the time. Our home is a dump and my parents are on the verge of losing the house to foreclosure. Luckily I have no other siblings to go through the hell I've had to endure.  

I'm a senior in high school and I get made fun off because my clothes are rags and I'm not very attractive. My peers can be very cruel and have no clue of what my life is like.

I only have one friend and I don't have any idea why he associates with me as he is a jock, star football quarterback and is very popular. We became friends in my freshman year. He says that he doesn't care what I look like that my personality and caring about other people is what makes me special.

His name is Colton and he is the most handsome dude in school. He is 5'10" tall, 180 lbs., light blond hair, and blue eyes that you can get lost in. He has the most amazing bubble butt that makes me drool. I guess your thinking I'm gay, well I am. No one in school knows for sure even though all the guys call me fag boy.

I do have one other friend and her name is Emily and she is the sweetest girl who has parents that are very rich. I just don't understand why they are so taken with me.

One day Emily told me she was taking me shopping for new clothes, a new haircut and contact lens replacing my ugly broken glasses. I became upset with her and told her I wasn't a charity case. Tears filled her eyes and she said: "Please let me do this for you, you have tutored me with some of my school work, its the least I can do for you."

Emily picked me up on a Saturday morning and took me to some very expensive stores. She picked out several pairs of really hot jeans, T-shirts, fitted shirts, two pairs of sneakers and a pair of boots. She told me to put on a pair of the jeans and one of the t-shirts and also sneakers. I came out of the dressing room and Emily just stood there with her mouth open. "Toby OMG your body is so hot, those bagging jeans and worn t-shirt hid your super body," and I just blushed. Next we went to get my contact lens and then to her hair stylist. I sat in the chair and this cute guy came over and he took one look at me and said: "Oh my, this is going to be a great challenge for me."

Emily left and said she would be back in one hour. The stylist whose name was Forest went to work on me and when he was finished I couldn't believe what I saw looking in the mirror. It was like seeing a different person. Forest said: "Oh my, my, my you are a very handsome young man." I blushed as usual as I was not use to getting compliments. Emily walked in and when she saw me tears filled her eyes and said: "Oh Toby I can't believe how you have transformed to an amazing hot guy." We went to lunch and I told Emily how thankful I was and that I would never forget what she did for me. I told her that I felt like a different person and that I also felt I didn't have to walk with my head down from embarrassment of the way I looked.

I never told Emily that I was gay, but I think she new because I never dated girls and she knew how much I cared for Colton. Emily picked me up for school on Monday in her Mercedes convertible and when I got in school and I walked down the hallway no one made fun of me as a matter of fact I don't think most of the kids recognized me. I saw Colton walking over to my locker and stopped short with his mouth open and just said: "Wow, I can't believe that's you, Emily told me she was taking you for a make over but this is a totally new you and I never realized how beautiful your hazel eyes were with the glasses, sorry I hope I'm not embarrassing you its just I'm in total shock."

Things really started to change for me as I wasn't being made fun of anymore and even the guys on the track team all wanted to be my friends. It just amazes me how shallow people are that your popularity is based on how you dress and if your face is pretty or handsome.

Emily brought me home from school and when we arrived there were police cars in front of my house and they were bringing my parents out handcuffed. I started to freak out and asked my Dad what was going on. He just turned his face at me and the cops wouldn't tell men anything. I found out from my parents lawyer that they were arrested on charges of selling drugs namely cocaine. The lawyer also went on to tell me that the house was in foreclosure and I would have to vacate within a week.

I called Colton to come and pick me up and when he arrived I had been crying and I was shaking, I told him what had happened.  He put he arms around me and told me I was moving in with him. We arrived at Colton's house and we sat down with his parents and told them the story. Colton's Mom got up and hugged me and said I was welcomed to stay with them for as long as I needed.

We went up to Colton's room and I new he had a full bed but it never dawned on me about sleeping together. He saw the look on my face and said: " Does it bother you us sleeping together?" Nervously I said: "Oh no not at all its just that when I slept over before I slept on the floor in a sleeping bag." "Well now that your going to be here on a more permanent basis you can't sleep on the floor."

We went back to my home and gathered by belongings and went back to Colton's. His Mom had made a wonderful dinner in which I was not use to. It was just all to overwhelming for me. I get a new makeover, my parents are arrested and now I have a new home. The tears were running down my face and Colton put his arms around me a said: "I promise everything is going to be fine."

That night we got in bed and my heart was beating a mile a minute as I had been in love with Colton for as long as I could remember. Colton had the pick of all the pretty popular girls, but never dated anyone on a regular basis. I awoke in the morning with Colton spooned against me and I could feel his hard cock on my ass crack. I just froze and didn't know what to do. The next thing I know he started moving slowly against my ass. My cock became rock hard and I slowly started moving my ass against him. My heart was beating so hard I thought it was going to explode. Suddenly he reached around and took hold of my cock and started stroking it. I turned around and looked in his eyes and said: "Colton is this what you want?" He said: "Oh Toby I have loved you for over two years but I was so afraid to make a move." I looked into his eyes replying: "Wow Colton I have felt the same way for so long." He reached over and his lips met mine and all of the pent up feelings were released. We kissed for what seemed like forever, and then our tongues began to dance and I was completely rock hard and so was Colton.

I told him that I had never had sex that I was a virgin and he said that he had sex a few times with girls but never with a guy. He went on to say that he would fantasize about us having sex and beat off to his fantasies.

Colton said: "Lets get naked. We started stroking each others stiff cocks, and it didn't take long that we were leaking pre-cum. I went down and started licking his huge 7" cock and savoring his pre-cum. I then went down on his pole and was sucking and making slurping sounds and he was going crazy. "Oh yeah, suck my cock Toby it feels so good."

I keep sucking his cock and trying to deep throat but I couldn't, but I know with some practice I eventually would. Colton said: "Lets get into a 69 position" and we started sucking each other. It didn't take long before we were devouring each others cum.

Colton kissed me and said: "Lets get some sleep and we will talk tomorrow."

The next morning we awoke at basically the same time and Colton reached over and kissed me and said: "This is a new beginning for us and your life is going to be full of love and joy please believe me Toby."

We dressed and went down stairs as Colton's mom was preparing breakfast. She said: "Sit down boys breakfast is ready." She went on to say: "Toby, Colton's Dad and I have discussed your situation and you are now part of this family and you will be receiving an allowance each week from us, the only thing we ask is that you help Colton clean his room and keep his bathroom clean." "You will also help Colton with the yard work." I didn't know what to say but tears started running down my cheeks. Colton's mom came over to me and hugged me.  I made a promise to myself that one day when I finished college and began a career that I would never forget what Colton's parents did for me and I would repay them for their generosity  

That night we took a shower together and got into bed naked and I said: "Colton I want to fuck you so bad." I told him to get on his stomach and spread his legs. I dove down and started licking his beefy globes and then spread his cheeks and with my tongue went straight for his rosebed. I pushed my tongue into his hole and sucked like a crazed animal. Colton was grabbing onto the sheets moaning and said: "Oh fuck Toby yeah, EAT MY FUCKING ASS IT FEELS SO GOOD!! I continued my assault on his pussy and then I told him to get on his back, I lubed my cock and placed it at his entrance. Slowly I pushed in and got past his sphincter and I could tell it was hurting him. I said: ""Colton just relax its not going to hurt much longer."

I continued thrusting into his love tunnel back and forth slowly until I hit his prostate and suddenly his sighed and said: " oh baby that feels good." I started moving faster and the feeling from his hot pussy was taking control of my lust for him. "Oh Toby RAM THAT HARD COCK OF YOURS IN ME DEEPER, OH YEAH FUCK ME, UN HUH, UN HUH, MMMMMM!!!

We both had an explosive orgasm, and I filled Colton's ass with a huge load of cum and he shot all over his face and stomach. I reached up and started eating the cum from his chest and then up to his face and proceeded kissing him sharing his hot cum.

We got up and showered and got back in bed and I said: "Colton I love you and I know you love me and I feel like I have gone from rags to riches in more ways then one.