All characters engaged in sexual activities are at least 18 years of age. Be forewarned, this story involves a very lucky and hugely gifted male who learns there can be a golden side to what he thought was a curse. If you can't handle stories involving much bigger than average equipment then just move on to the next story. This story is total fiction so any resemblance to real persons or actions is totally coincidental.
The first time I felt different was when I was ten and my mom took my waist and leg measurements and bought me new blue jeans for school. When I put them on, with her help, I winced in pain. She asked me what was wrong and I said through gritted teeth, "Too tight, Mommy, too tight!" She put her fingers in the waist band and jiggled it as I grimaced again. She told me I had plenty of room and I said, "Not there, here," and I pointed to my crotch.
My mom stood up and closed my bedroom door before she knelt before me and unsnapped then unzipped me. As soon as she tugged the jeans down just a little bit I moaned a sigh of relief. She looked at me with a very puzzled expression before pulling them down all the way. "Oh thank you Mommy," I said, "the pain is gone now."
"Okay, Jimmy, please point to exactly where it hurt you." Mom raised her eyebrows when I pointed to my cock in my briefs. "You're sure, honey?" Again I pointed with my finger right on my cock. She looked very nervous and I couldn't for the life of me figure out why. "Well, maybe these are too tight," she said and tugged my underwear down to my knees.
I noticed mom was staring into my eyes as she did this and then still looking in my eyes she said, "Is this any better?" When I told her not really she said, "Let me get your dad." He came in and pulled my pants back up making me wince in pain again. Taking one look at me he told me to take them off, then told my mom that I needed to have dress slacks instead of jeans...that I needed more room. She never bought me blue jeans again, and the kids at school teased me all the time about my 'business suit' like pants that I always wore.
I guess I should tell something about my family, so here's a brief synopsis. Mom and dad got married when she was almost 14 ½ and he was 19, which resulted in my sister being born when mom was 15. I was born 10 days after mom's 16th birthday. There were complications and mom could no longer have children. I am now a high school senior of 17, my sister Meg is 18 and goes to the local community college. My dad showed he is still just a little prick when he packed his bags 3 years ago and left to shack up with his 21 year old secretary. After he left that night, when my mom finally stopped crying she said to me, "I guess that really makes you the man of the house now." I never caught the significance of her wordage till after my 18th birthday.
Just before my junior year started, I turned down an invitation from my grand father and my uncle to go fishing with them. My mom really thought I should go but I didn't like leaving her alone so I stood firm in my decision. They called the day before heading back home telling me I'd really missed a great time as they had caught tons of trophy sized fish. I told them I'd believe it when they got home. They never made it. An over hours semi truck driver crossed the center line at 90 miles an hour and flattened grandpa's F-150 pickup.
My mom told me after the funeral that I was now the man of the entire family. Grandma Karla had my mom when she was 18; she had my aunt four years later. Then her doctor found some cysts on her ovaries and had to remove them. So anyway, here I am, 17, almost 18, with Meg also 18 years old. Mom is 34; her birthday was eight days ago. My aunt Peg (who never had any kids) is a few months away from being untrustworthy (30) and my grandma is a very nice looking 52 years young.
*****
It was a Friday night and I had a date with a new girl in school – none of the girls I'd grown up with would go out with me due to the rumors about my having a tube sock stuffed in my shorts. (Our school had no gym class and I wasn't into sports so nobody there had a chance to know the truth.) Just before midnight that night I walked in the house, slammed the door then stormed off to my bedroom. Shortly my mom tapped on my door wanting to talk but I didn't feel like talking. I felt like a freak and thought I should see a doctor to get my problem fixed. Tomorrow I'd be 18 and inherit some money from my Grandpa and I would use that to end my torment.
"Please, honey, let me in so we can talk. I know you are upset, maybe we can talk it over and you'll feel better," my mom said. After the fifth time pleading with me I unlocked the door and told her to come in if she had to. I was lying on my stomach on my bed when she entered the room. "Jimmy, what's wrong, what happened tonight?"
"Oh, mom, it's the same shit, just like always!" I said as I buried my head in my pillow.
"Jimmy, you always say that but you've never told me just what the 'shit' was the first time. It's just 'the same shit' what ever that is. How can I help you if I don't know what it was to begin with?" Mom's face was painted with anguish and I could tell she really wanted to help me with whatever was bothering me.
I surprised her by flipping over, my hand grabbing my shorts shrouded crotch as I yelled "This, mom, this is my shit, it has ruined my life and I'm sick of it! As soon as I get my inheritance I'm getting my life back!" Then I quickly rolled back onto my stomach.
My mom slowly reached out and lightly stroked my arm saying, "I don't understand what you're talking about! Please talk to me, please, let's go down to the kitchen and talk comfortably."
"Oh all right, mom." I answered. "Let me put on my sweats and I'll be right down."
