Lessons Learned

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!

I pulled into the drive and the house looked empty, when I walked in I saw a note on the fridge from my parents "Gone to the cabin for the weekend have fun see you Monday." I opened a beer and sat at the table it was 5:10 and I was picturing Mr. Willis in front of me and how easily held both my wrists in one of his hands, I felt my dick starting to swell in my shorts, I took another sip out of the bottle feeling like I needed to loosen some pressure that was building, I pulled off my shorts.

My dick was tenting in my boxers, I was so confused at my feelings. Did I like feeling submissive to him? I stood up and pulled my boxers off and my hard 4 1/2 inch dick popped out. I looked down and thought Mary was lying my dick wasn't small at all. I was making my way to my computer to look at some porn which I have been doing a LOT lately when I again heard Mr. Willis's voice in my head.

"If I don't hear from you by 5:30 I will assume you aren't coming back for more training!"

What the fuck did he mean more training? "Fuck that this is bull shit I am not going to his house to find out."

I told myself over and over that I wanted no part of what he was talking about, but my hard dick was telling me a totally different story. I looked up at the clock and it was 5:27, I thought to myself what the hell I'm alone with nothing to do I can always leave. I grabbed my phone to text Mr. Willis.

"Hi Mr. Willis it is Bob. I apologize for any disrespect I may have shown you early today. Although the swift but fair punishment you handed out to me today did show me that I disrespected you and that what I had done was wrong. I do believe I may need further training to  help me understand how I may better myself and understand how to show the respect to you that you so deserve. I sincerely hope you can help me with learning my lesson."

I hit send and looked down at my dick sticking out and now oozing pre cum and said to it as if it could understand me.

"You are betraying me!"

I laughed to myself and went up to shower. Right before I stepped into the shower my phone went off, it was Mr. Willis.

"Glad to hear you understand your place Bobby! Remember be here by 6 sharp no later or there will be extra discipline for tardiness. Park around back you know the secluded area blocked by the trees. I expect you to remove all your clothes before you knock on my door. See you soon! Mr. Willis."

Shit I was going to have to hurry to get there by 6. I shouldn't have wasted so much time. I showered quickly, my stomach was in knots the whole time flip flopping around, my mind filled with all kinds of dirty thoughts and my dick never once going soft! I combed my hair, put a clean tee shirt on and a pair of beach shorts. I decided to skip the underwear since I was instructed to be naked by the time I was at the door anyway.

I left my house and sped to Mr. Willis's I kept looking at the clock in my car. 5:58 shit I wasn't going to be there by 6 what the fuck! I pulled into Mr. Willis's driveway at 6:03, I was late. As I pulled around back and parked where he told me to, I contemplated scraping this crazy idea and just going home. I am not gay I have never even thought of a guy before, what the hell are you doing here Bob? I tried to rationalize with myself. Then my phone went off, making me nearly jump through the roof of my car. It was Mr. Willis.

"Do you see the time Bobby? It is 6:05, I am very disappointed. I don't like to be kept waiting for my boi. I am a very busy man, I am not here to play games Bobby are you going to come in or are you going to turn your car on and leave? If you are coming in I suggest you get YOUR ASS IN THIS HOUSE NOW BEFORE YOU REALLY GET ME ANGRY!!!! again the DECISION is your boi I hope you chose wisely"

I put my phone down, what the hell, I have been feeling lonely anyway, I looked at myself in the mirror and pulled my shirt over my head, then slid my shorts down springing my dick free. Looking down at it I again said to myself. Why? Why are you so turned on? I opened the door leaving my clothes folded on my front seat, I walked naked to Mr. Willis's door.

As I approached the door it opened before I even reached it and I saw him standing there again backlit by the house lights. Mr. Willis was dressed in what looked to be latex shorts with no shirt on. He had a definite scowl on his face which I could make out clearly as I got closer. Mr. Willis spoke.

"You disappoint me Bobby. We are not off to a good start are we boi?"

He took a look down and a big smile came across his chiseled face when he noticed my dick was already standing at attention.

"Well well Bobby what do we have here? Is that what you call a dick? That is hardly a penis boi it's a good thing we will be keeping that little thing locked away as we continue to train you"

He reached out and slapped my hard dick not a hard slap but hard enough to make me flinch. His words kind of hurt my feelings and made me think maybe Mary was right, maybe my 4 1/2 inch dick was small. I looked up at the man towering over me and spoke.

"May I come in Mr. Willis? What if someone sees me naked out here?"

He stepped aside to allow me to enter his home, stopping me before I got too far into the house. He grabbed me by my shoulder and turned me to face him. Looking up at this giant muscular black man I felt different than I ever have in my life. I am not gay but I felt submissive to him, at that moment I felt as though I wanted to please him. It was his pleasure that mattered the most. It was his approval of me and my behavior that would actually give me my pleasure. Right now as I looked up at Mr. Willis I knew I would do whatever he told me to do if it would earn his approval and please him. He broke the silence.

"I want to ask you point blank Bobby, do you feel in any way that you have to be here? That is not my intention. I want you to know that I want you to be here for your own reasons and on your own free will."

Standing in front of Mr. Willis naked my penis staying hard the entire time I now had a string of precum hanging from the tip of it. I couldn't help notice the HUGE bulge in his latex shorts and as he was talking to me, I was wondering what he had in the front of his pants. Without saying a word I reached out my hand for his crotch almost as if someone else was controlling it and touched his bulge making him flinch for the first time in all of our exchanges. Looking up at him with my hand on his cock I said.

"No Mr. Willis you have not done anything to make me feel like I am here against my will. I am here because I want to be, I am here because I feel I did disrespect you and I feel you have been nothing but patient and kind to me and I want to learn from you."

As I was saying this I felt his cock getting even BIGGER! I thought there was no way that could be possible. A big smile started to form on his face as he allowed me to keep my hand on his crotch for another few seconds before slapping my hand away.

"Do you like what you feel boi? That is more than you ever played with before isn't it boi?? Before we get started for the night I want to go over a few things, let's call them House Rules.

1. You were late tardiness is never acceptable there will be additional punishment for this. 2. When in my home you will only address me as Sir, Daddy or Master. 3. You will do as I say when I say or I will see it as a sign of disrespect and there will be additional punishment. 4. If you ever touch my cock or your cock again without permission or being told to, you will be punished. 5. I will refer to you as boi, slave boi, little one, slut or bitch. 6. If I feel a friend is in need of some service, whatever that may be, you will obey. 7. Once training begins you will have that little dick of yours kept in a chastity cage which only I will have the key for.  8. You will be shaved from neck to thighs front and back, I want you smooth and as hairless as can be. 9. If at anytime you feel you are not enjoying your training your safe word will be lemon. Say lemon and I will stop and you will be free to go, but once you leave you can't come back. Are these rules understood boi?

I simply spoke "Yes Sir"

"Good now what kind of training time do we have tonight little one? With your tardiness we lost some valuable time."

"If you would allow Sir I can be here the whole weekend if that is not overstaying my welcome Sir. I am the only one at my house the entire weekend Sir so no one will question anything."

Looking at me Mr. Willis smiled.

"Very good boi very good you will stay with me the whole weekend. We will be able to get some good training in. Now first things first I see you have disobeyed a direct order. I specifically told you I expected you to be CLEAN when you came to my house tonight. Look at this! There isn't much but a slave boi like you should have no pubic hair at all! You should shave it all off. Remember rule 8 little one? Bend over I bet your ass hasn't been shaved either!"