Lessons Learned
Chapter 1: The Decision
My name is Bob, my family and some close friends still call me Bobby. I just finished my Junior year of college and recently turned 21. I am 5'8" 128 LBS and my life is kind of blah. You see I am what you would call an average guy. I am not unattractive but also no one is lining up to be with me. I have learned to deal with it.
I had always been a good athlete when I was younger but once I hit High School it just seemed all the other guys shot past me in height and size. No matter how hard I tried I just couldn't add muscle to my body and to make things worse I was done growing when I hit 5'8". I know it is technically not short, it is "average" but at that point I just stopped trying to make whatever team because I knew it wasn't going to happen. I never had a real girlfriend until the start of Junior year of college.
I met Mary at school. She lived two towns over from me but went to a different high school so we never knew each other. Mary was short and a bit overweight but I thought she was sexy. She had a nice big round ass and full tits. She was far more sexually experienced than I was. When we first started dating she had told me that she started to "put out" at an early age feeling like that was the only way she could get a boy to like her. I told her she was crazy. I liked her for the person she was. She was amazing to me. I was in love and told her every chance I could. I remember the first time we had "sex" we had been kissing and things were getting hot she told me to get a rubber. She knew I was a virgin so she told me she would put it on for me, she pulled my pants down and I heard her make an almost disappointing moan. I asked what was wrong she stammered for a second and said
"Oh it's nothing Bobby it's OK let me get the rubber on your penis." As she grabbed my dick and tried to slide the rubber on I lost it and started to cum right then. I sprayed all over her hair and chest.
"Dammit Bobby what the hell!!!! Couldn't you warn me you were going to cum?? Shit now I am a mess ugh!!"
She got up and went to the bathroom. I followed her to apologize but she slammed the door and I heard the water turn on in the shower. When she got out of the bathroom she grabbed her coat and said she had to go. I begged her to stay but she walked out. The next day she called me and asked if she could come over and talk. I of course said yes. When Mary got there we sat down and she started to tell me why she stormed off on me.
"Yesterday I was really...well horny and I was hoping we would finally have sex. Things seemed to be going well in our relationship but every time we got close to sex you stop and say you want it to be perfect. I was so ready to take the next step and then when I pulled your pants down I.....I... well I don't want to be mean Bobby but you are kind of small down there don't you think?"
I was shocked, I never thought of myself as having a small dick I mean I knew I wasn't hung but I didn't think I was small. Although I never really looked when in the showers in gym class. I wrapped a towel around my waist, ran in looking down, showered, ran out and got dressed. I started to talk, wanting to protest, then Mary cut me off.
"I think I could get past that Bobby but then you shot your cum before I could even get the rubber on you! I was still horny and you fell back on the bed finished and looking spent. I just had to leave!"
We worked things out at least for a little bit but I was always what you would call a one pump chump LOL. Mary often told me I was the fastest cummer she had ever been with. After dating for a while and with her being on the pill we started having sex without rubbers that made me cum even faster. It would really upset her so much that she would say she wasn't getting hers but I got mine.
So she would have me lick her pussy after we had sex to give her an orgasm. I didn't really like it because I was licking up my cum from her pussy, but I loved her so I did it. Our relationship didn't last too much longer, before the end of Junior year Mary broke up with me, she told me she needed more from a relationship than I could give. I was pretty hurt but I knew in my mind it was probably for the best.
Once home from school I started my summer job up, the same job I have had since I first started driving, working at a landscaping company. It was great working outside during the summer being in the sun seeing the occasional sunbather by her pool. It was what I needed to fully get over Mary. One Friday when I got into work Mr. Johnson approached me.
"Bob, I need you to take out truck 3 today. You will be alone. We had 2 people call in sick today, just get done what you can but the most important task for the day is the Willis property. I trust you can handle this, you've been here for years. Thanks Bob!"
I was feeling good Mr. Johnson trusted me to get the work done without a supervisor, I wasn't going to let him down. The Willis's lived in the subdivision over from where I grew up but worlds apart prestige wise. They had the biggest house in the neighborhood with the most property to care for. I pulled up and started to get ready for the day when I saw Mrs. Willis pulling down the drive and stopping by me. As she rolled the window down I couldn't help but stare and think to myself how stunning this looking older black woman was. She was around 50, so kind and beyond pretty.
"It's Bob right? I made some lemonade and put it on ice, it is on the table just inside the patio door. Feel free to help yourself whenever you get thirsty the girls and I are going to visit my sister for the week Mr. Willis is home but upstairs working no need to bother him. Have a great day!"
As she drove off I thought to myself I wonder if her daughters even know who I am. I am 2 years older than the twins, we have totally different lives, they are beautiful and popular and everyone wants to know them. After a few seconds of feeling sorry for myself I got to work.
After about an hour I really had to pee and I was getting thirsty. I went to the far corner of the property to relieve myself then went to get some of that lemonade Mrs. Willis had told me about. I felt strange just walking into someone's house but it's not like she didn't say I could. I opened the sliding door and saw the lemonade on the table with a glass next to it. I walked over and poured myself some, I started to take a drink when I heard a deep voice from behind me.
"Well it must be nice to just walk into someone's home like you own it!"
I turned to see Mr. Willis standing behind me, towering over me at 6'4" and built like a black Adonis! He is pure muscle and looks like he could have played pro football. I was so nervous as I started to speak.
"Oh no Mr. Willis I am so sorry I mean no disrespect, before Mrs. Willis left she had told me that the door was unlocked and she had made lemonade and offered it to me. She told me you were home but would be upstairs working and not to bother you. I am very sorry."
Mr. Willis started to slowly walk towards me. The basement was dark with only one light on that backlit him making him look even more menacing than he otherwise would have. He was now standing less than a foot from me, he grabbed me by my arm, spinning me around pinning my arm to my back. I was literally shaking as he leaned in and whispered in my ear.
"A disrespectful boi like you needs to be punished, don't you think? I feel like you need to be taught some manners, maybe learn some lessons no man has ever taught you. Does that sound right boi?"
I didn't know what to say, I was almost in tears. I was trusted by my boss to get a job done, one of his oldest and most important accounts and here I am breaking into his house, I could be fired. Then Mr. Willis started to speak again.
"I also saw you on my security camera, boi what were you doing in the back corner of my property? I bet you had taken a piss is that right? Did you take a piss in my yard? Seems like that alone would deserves some punishment don't you think boi?"
I didn't know what to say or do, I was frozen. I said I was sorry again then he pulled my basketball shorts down just over the round of my butt cheeks and slapped me three times really hard. Mr. Willis then released my arm from behind my back and turned me around to face him.
My heart was racing as I looked up at his scowling face. I was feeling light headed and a bit weak in the knees, I also felt a strange but familiar tingle in my groin. Although I was feeling a bit scared there was an erotic tension in the air, one I never felt when Mary and I were together. Perhaps it was because I never had it in me to take total control like Mr. Willis had in this moment. Leaning in even closer, so close I could feel his breath as he spoke.
"So boi what do you think, do you need more of a punishment for the things you have done today? I will leave this decision up to you, if you feel you want to make things right with me and you know you deserve to be punished by me for your insubordination I expect to see you back here at 6 pm sharp this evening. Is that understood? If you decide to come back I expect you to be CLEAN like a boi should be, is that understood? If you feel the three smacks have been punishment enough and you have learned your lesson, I will let it be and we will move on, but if that is the case from here on out if you work on my property there will be no second chances. If you piss in my yard, break into my house or disrespect me or my home in any way I will have you fired. If you don't come back for further punishment and training and you follow the rules and never have a miss step we will have no problems. As I said, the DECISION is yours boi! Take my number from the work file and text me to acknowledge your decision. If I don't hear from you by 5:30 I will assume I will not be seeing you and assume you have learned from your mistakes and we can put all this in the past."
He stepped aside and let me walk out the door. I continued to work but I have to admit the rest of the day my mind was all over the place and everywhere but on work. What the hell was that? Why didn't I just kick him in the balls and run out and why is it that when I think of him smacking my ass my dick starts to jump???
The rest of the day was both a blur and seemed to drag on but it was Friday and payday so I was looking forward to the weekend, but then I thought to myself what was I looking forward to? I was just going to sit at home and watch movies, another blah weekend in my blah life because there was no way in hell I was going back to Mr. Willis's.
It was almost 4 pm when I pulled into the shop, by the time I unhooked the trailer and parked the truck Mr. Johnson brought me over my paycheck it was 4:30 and I was headed home. As I drove home my mind kept flashing to the incident at Mr. Willis's. Even though I was never a ladies man I was never into guys, never once had I ever looked at a dude and thought yeah I want some of that. Hell Mr. Willis was old enough to be my dad!
