Chapter 1: Life Sucks

Did you ever have those days when life really sucks? You get so low you seriously consider packing it in and taking a dirt nap. Well, let me tell you, I've had quite a few lately. It seems like fate had it in for me and decided to deal me the worst hand it is possible to hold. I guess you could sum up my life so far in the expression 'almost but not quite'. My name is Greg Thomas and if you have read some of Stepdad's stories you'd think I had all the luck in the world. Unfortunately that is another Greg Thomas, not me. It seems to me that he took all the Thomas luck for himself and left me with just the crumbs. Actually, if it weren't for bad luck I wouldn't have any luck at all.

I can give you some examples:

When I was in high school I lusted after the most beautiful girl I had ever seen named Jean. She was a true centerfold quality goddess and made me hard every time I just looked at her. She was captain of the cheerleader squad and very popular with the jocks in school. Her long blonde hair surrounded a pretty face which glowed with sensuality. She had a perfect figure with legs which went all the way from the ground to heaven. Now, I was kind of shy around girls and could not work up the courage to ask her out. I found out years later that she also was a bit shy and wondered why I had never asked her. She would have jumped at the chance but it never came to be. She ended up marrying some muscle-bound jock who treated her rotten and left her high and dry with two kids to support.

I came to the realization that Jean was totally out of my league so I had to give up on her and get on with my life. Through my church youth group I met a nice girl named Barb. She was pretty and we clicked early on. After dating for a couple of months she agreed to go steady with me. I felt that we were truly in love and destined to spend the rest of our lives together. I was on top of the world and I felt that my luck had finally turned around. I had graduated from high school and had my own car. Barb and I went out quite a lot and enjoyed each other. She liked to go to a popular make-out spot and just hug, kiss and fool around. We had sexual contact but never went all the way. She was proudly wearing my ring on a gold chain around her neck so all the world could see that she was taken. We held hands wherever we went and riding in my car she would be right up against me holding my arm. She would lean over and give me little kisses on my neck making me the luckiest guy in the world. One day she wanted to go to a neighboring town with me to a football game. I wasn't all that much into sports but the chance to be with 'my girl' was worth it. Barb introduced me to one of her male friends and we three sat together and watched the game. I noticed her looking at him kind of strange but chalked it up to them being just friends. She asked me if we could give him a ride back home and, being a nice guy, I reluctantly agreed. We ended up in the front seat of my car with her in the middle. I got an uneasy feeling when she didn't snuggle up to me but I just thought she would be embarrassed to show affection with her friend there. We drove along for a while before I noticed that my steady girl and that guy were kissing. I was stunned and could not say a thing. They made out for the rest of the trip and when we got to his house he told me, "Greg,, your sister is really hot." I guess she had told him that we were sister and brother. After dropping him off, we rode in silence to her house. She got out, without our usual good night kiss. I walked her to the door and she told me that it was over and that my ring was hanging on the heater knob. She sure had one hell of a way of breaking up.

You might get the impression that my sex life was near to non-existent. That was not necessarily the case however. I had a younger sister, Sandy, who I eventually noticed was a living sexpot. She had a nice figure and a pretty face. We got along quite well and did a lot of stuff together. She liked to tease me by dressing as skimpy as she could get away with. She would come out of the bathroom after her shower with a towel draped around her body and when she saw me looking at her she would deliberately drop the towel displaying her charms to my hormone fueled horny gaze. She managed to seduce me and I went along with her efforts like a starved puppy. Sometimes she would sit on my lap as we talked about this and that. I would rub her bare thighs getting us both worked up to a frenzy pitch. I moved my hand higher under her skirt until I made contact with her damp panty crotch. I worked my finger inside until I was caressing her bare pussy and causing her to breathe hard and moan out her pleasure. On several occasions I managed to give her an orgasm and she reciprocated by giving me hand jobs right after her orgasms. Sometimes we did it together on her bed coming together at the same time. We had to be very careful so mom didn't discover what we were doing.

One time she was laying on her bed with her legs hanging over the edge while reading a book. She had a short skirt on and her delicious looking legs were on display for me to see. I sat down next to her and started to rub her leg. I made my way up to the crotch of her panties and rubbed her there for a while causing her to move her legs apart and start breathing hard. I reached up and slid her panties down to her knees and then rubbed her naked pussy. We were both getting worked up so I took out my erect cock and rubbed it up and down along her slit. She tried to spread her legs to get more contact but her panties kept her from making much progress. She sat up and pulled her panties down and off so she could spread her legs farther. She lay back down and I continued to rub my cock up and down her sexual center. She would give her hips a little flip when the head of my cock was at her opening so I pressed harder trying to enter her. Just then we heard our mother coming up the stairs so we made a mad effort to get decent and act innocent. Mom had some laundry to put away and told us that she had lunch ready. We went down and ate our sandwiches. Mom told us that she was going to take Sandy downtown to the doctor's office since she had not been feeling too good for a couple of days.

They were gone for several hours and when they got back home, mom was as white as a ghost. It took some time but mom was able to tell me that my beloved sister was sick with a cancerous growth on her uterus. She would have to go to the hospital the next day for them to operate on her. They opened her up and discovered that the cancer had spread and they did not have too much hope for her to survive. She got sicker and sicker by the day. One day when mom was out getting some groceries, I was staying with Sandy trying my best to comfort her. We both knew that she did not have long to live and cried with each other almost continuously.

Sandy asked me, "Greg, do you remember what we were doing the day mom took me to the doctor?"

"Yeah, we were so close to going all the way when mom came up."

"Greg, I was ready to let you take my virginity right then and there."

"I kind of got that idea."

"Greg, I've got a big favor I want to ask you to do."

"You know I will do anything for you."

"I don't want to die a virgin. My darling Greg, would you make love with me and make me a woman?"