My Mentor and Me

In 2016, I was part of this program in college. The program was for young black men to connect with older (wise) black men. It was made to make us young men understand how to continue to be successful and prosper in the world. The program was definitely a great contribution to my life.

So I went to the program one particular day with my homeboys, Lock and French. Those are their nicknames and yes they are cool with being part of my story. They were part of the program as well. I went to meet me my mentor, we will call him Dennis. He was a good looking black man. He was always dressing suave and fresh. Lock and French hated that I had the cool mentor. He would buy me stuff for my dorm. He invited me over to watch the game. He even introduced me to his boss at a company he worked and put in a good word for me. It was a black owned company. I was glad to have met my mentor.

Now y’all probably like this sounds too good to be true. Yeah, to me it was too. Well I started to grow an attraction to him and couldn’t stop thinking about him. One day, I went over to his house do he could help me out with a project I was working on. I pull up and see that he had a driveway with four cars. Now, he own two of them, but the other two were new to me. I was like I know this man didn’t buy me no car. I wouldn’t accept it....at first. Lol!

I walked up to the door and rang the door bell. Then, a young man around my age answered the door. I was shocked like who is this?

“Hello, is Mr. Dennis home?” I asked. “Oh, yeah, you must be the dude my dad talked about?” He said.

Your dad?I was completed shock because I didn’t know my mentor had a family. He did mentioned that he got a divorced a few years back, but not a full on family.

“Uh, yeah, I’m James.”

“Cool. I’m Kenard. Nice to meet you. Come in.” Kenard said letting me in.

“Dad, James is here!”

“Alright, send him to my office!” Mr. Dennis shouted from the other side of the room.

I walked to the office and he was in there looking stressed. He had paper all over his desk and erasing numbers on a sheet. I put my stuff down and sat in the chair. He looked up at me and said,

“I’m sorry for the chaos. My family came over for the weekend and these numbers are not adding up for this event next weekend. Do you mind getting started and I will come help you in a few?”

“Yea. No problem.” I got up and went to the office table to get started.

I heard him ball up some paper and threw it on the ground. I saw it roll over to me and I picked it up. I looked over his work and noticed the error. I hated math, but it comes to me easily if I sit a while with it. I corrected the mistake and handed to him. He stared at it for a minute and smiled.

“Well I’ll be damn. You really are something else! Thank you!” Mr. Dennis said giving me a dap. We did our handshake and he came over to help me with my project.

We finished around 7:30pm and I needed to head back to my dorm. So, I started to pack up my stuff when his son, Kenard, stepped in. He asked if I wanted to take some food back with me to school. Well I’m not gonna stop anyone that wants to give me free food. I accepted and made four plates of everything. They didn’t mind. I got to meet Mr. Dennis two sons and ex-wife. She seemed nice and I could see what he saw in her. She had a beauty that stood bright and loud from across the room. Though, she had a snappy tongue. She tried to tell her son not to associate with me. Like my grandma always say, “Roses are always pretty until you get stuck by it’s thorns.” And she was talking about her.

I got in my car and Mr. Dennis helped me load my car with my stuff. As I was getting something straightened in my car, I could’ve sworn I heard that Jack’d notification sound. Now, I knew it wasn’t mine because I put my notifications on mute when I got to his place. So, it had to be him. I ignored it like he did and got in my car. As I was pulling off, I went around the corner to find him on Jack’d. If I’m still in the area, that’s he should still be there, right?Boom! There he is! I could tell from that bow tie he was wearing in the picture. No face, but clothing. Everything that his status said is what he looked liked. I was hesitant at first to hit him up. Then, I said fuck it! Just do it! I sent the message and drove off.

I didn’t check my phone until I got to my room. When I put my food down my phone buzzed twice. My roommate was like, “Damn bruh! Who blowing you up tonight?” I literally said, “I have no clue, but I’m about to find out.” I looked down and it was 15 messages.

10 from my group chat with Lock and French. 2 from Mr. Dennis. And 3 from Jack’d.

I ignored all of them except the Jack’d messages. I wanted to know if was really him and as soon as I opened it, it was literally him. He sent a face picture and saying,

What’s going on? My name is Dennis.

I am not lying to y’all. I had to catch my breath. I sent back a message and we started talking for about an hour. Eventually he asked for a face picture and I got hella nervous. Like how do I tell or show this man that I’m interested in him? Won’t it look weird if he finds out it’s me? Will he treat me differently? I mean are grown adults. Yes I am 25 years younger than him, but what could possible happen? So I unlocked my pictures.

I sat by my phone for a whole five minutes wondering what he is gonna say or think when he see it was me. Then, after another five minutes, I got a response. He said he was surprised to see me on here and don’t think we should mess around. I told him that it is awkward, but we can still be cool. I won’t tell if he won’t. He said that he treated me like a son and didn’t want to mess things up. If only he knew that was already calling him daddy in my dreams. Ha! I tried to smooth it over and said could we talk face to face. He agreed and said it would have to be next Thursday.

A few days go by and things are still normal. We continued to meet at the school, but did not talk about what we knew about each other. Then, Thursday came. I took,a long shower trying to get my mind together. I texted him and said I was on my way over. He texted back ok. I drove over thinking it was going to be a whole lesson/lecture from him. He’s good at doing that from time to time.

I pulled up and rang the doorbell. My hands were shaking like a leaf in the wind. He opened the door and he had on silk pajamas and robe. Now, if he wasn’t tryna turn me on then I don’t know what he was doing. He told me to come over to the kitchen because he made lunch. This man made a gourmet sandwich and fresher baked chips. Now, he really showing out. I sat down at the table and examined my food first. I got a thing about food. If I didn’t see you make it then I need to make sure it’s good enough to eat. So, I took a bite after I checked it. I didn’t want to eat too much of it though.

Mr. Dennis sat down next to me and said,

“James, like I said before, you are like a son to me and I don’t want to do anything to jeopardize that. I care for you like your my own. Please understand that.”

I sighted and said, “I understand. I was just taken back that you got down like that. I didn’t know you were into men.”

“I am into men and women, but I don’t mess around unless it’s consensual and within reason.”

Then, something clicked in my head. I am consenting that he can have my body. I can also think of a few reasons to make sure he is satisfied. I slid my chair to him and said,
“Dennis, we are both adults. I am giving you permission to do what you feel in this room right now.”


Dennis slid back his chair and walked away from the table. He went in his office and closed the door. To be honest, I liked having the upper hand on him. I could tell in his eyes he wanted me. If he didn’t, then he would’ve put me out after that statement. I got up and walked into his office. He was sitting on the edge of his desk with his hand on his forehead. He looked at me and back down to the ground. I took a step inside and he looked back at me. It was like he was undressing me with his eyes and I liked it.

“J, if you promise that this won’t mess up anything, then I guess we can try something.” “I’m only okay with it if you are.”

“Let’s just see how this goes. Come over here.” He said standing up.

I gave Dennis a hug and could feel myself melting in his big arms. He smelled so good and felt like a teddy bear. Oh wait, y’all don’t know what he look like. He is 6’0”, stocky body with muscles, bald head, brown cocoa skin, and a beard. He was fine as fuck to me. His teeth were straight and he had great taste in clothing. That slick outfit he had on felt smooth on him. Dennis looked down at me and leaned in to kiss me. Let’s just say it putty in his hand. At first I thought it would be weird, but after that first kiss it was a wrap. He flipped me around on to his desk and laid me down. He started to kiss me all on my neck and ears. My dick was solid as a rock. I wrapped my legs around him as he lifted my shirt up and sucked on my nipples. I could tell he was into me by the way he got more aggressive.

I slid off his silk pants. He threw off his rob and shirt, then took off my pants. I legit was so turned on that it was the best feeling in the world. I had to taste his dick. He went to sit in his big desk chair and I got on my knees to suck his dick. It was swaying from side to side. I tried to catch it with my mouth and when I did, it went to work. Dennis groaned and moaned from me going deep and playing with the head. He pushed my head down and started to talk nasty to me.

“That’s what you’ve been wanting huh? Some of daddy’s dick? Get that dick wet.”

In my head, I am completely shocked as to who this man has become. But I cannot lie, I was getting turned on. He held my jaw and slow stroked his dick in my mouth. I couldn’t believe Dennis was this kind of freak. After doing that for a while, he bent me over and started eating my ass. Y’all Dennis glorified my hole with that tongue. He spelled my name, his name, the alphabet, solved the astronomical equations, and wrote a whole history book on eating ass back there. I was so weak from that, I slid off the desk. He picked my big ass up and took me to his bedroom next door. He threw me on the bed and I just laid there out of breath.

“You came over here ready, didn’t you?” Dennis asked stroking his dick.

“I’m not gonna lie....I was hoping you was ready.” I laughed.

“Well, we’re here now. My dick is had as fuck. You got me in my beast mode. So, what’s next?”

I laid there thinking of my rule. Don’t fuck on the first meet. It is struggling rule because sometimes the word is strong, but the flesh gets weak. So, I took one for the team and said,

“You got some condoms?”

With a quickness, he went in his drawer and got the condoms and lube. He licked my hole again and stuck his tongue in it. I moaned as he rubbed the lube on my hole. It was soothing and that’s when I realized he was fingering my hole.

“Is that your finger?” I asked moaning.

“Hell yea. I couldn’t help it.”

“Shit daddy! It feels so good.”

“Ride that finger then.”

And I did just that. I was riding his finger like it was a dick. He had me precumming all on his sheets.

“Damn, son! You really know how to work daddy’s finger. How about you try this dick now?”

“Yes, sir.”

I bent over and arched my back. All I heard was damn son!He smacked my ass and slid up to my hole. I can still feel the top of his dick poking my hole. He told me to breathe and relax. He was really generous in beastly kind of way. Dennis pushed that head in me and I could feel it opening me up. He pulled it out slowly and continued to do that until I was opened. When Dennis got me opened, I started to slide back on his dick.

“Ooooh shit! You’re dick is so big and heavy.” I moaned.

“I got you. I’ll go slow.”

Dennis slow stroked my hole for a good five minutes. Then, I pushed back and he grabbed my waist to pull me back. I felt all that dick. Ugh! That dick felt like it was in my stomach at this point. Dennis grabbed the back on my neck and grind in my hole. That’s when started to fuck me. His dick went in and out my hole. I just went with the motions.

“You love daddy’s dick? Tell me you love it!”

“I...love...daddy’s...dick! Fuck me!”

He smacked my ass and kept fucking me. I was oozing precum all over the sheets. I couldn’t help it. That dick made me so weak that I collapsed on the bed and he kept fucking me. I moaned and groaned until he stopped. Dennis flipped me over and kissed me.

“Shit, you okay?” Dennis asked kissing me.

“Yea. I’m good. It’s just that dick is something else.”

“You want some more?”

“Yea.” I said with a sigh.

“Don’t worry. I’m close. Believe me. I feel the tightness in your hole gets when I go deep.”

“Really?”

“It’s like your hole is sucking my dick.”

Those words turned me on and opened my legs for Dennis. Y’all let me take a second to adjust my bulge. Ok, I’m good.

Dennis slid between me and slowly worked his dick in my hole. I could feel my hole opening up again as if it wanted that dick in me. He got nasty with it. He put his hand around my neck and started going a little harder. I can feel a build up in my dick and felt like I was gonna cum. At this point, I was ready to nut. But instead of nut, I started to piss all over myself. It was like I was having an orgasm without busting a nut.

“Fuck! Squirt that shit!” Dennis shouted. “I’m bout to bust!”

Dennis kept fucking me and I started to play with my dick. I’m squirting and getting close. Dennis is getting close too. Then, all of a sudden, we both bust together. He nutted so much that the condom was sagging heavy when he pulled out. I shot passed my head.
When we were done, we took a shower and laid in the bed. He told me that he enjoyed me and we definitely have to do it again. I agreed and got dressed. As I was walking out the door, his son, Kenard, walked up to the door and smiled.

“Maybe one day you can make me feel as good as you make my dad.” He said pointing to my shirt with the nut stain. I smiled and looked behind myself. He had a fat booty on him. I might have to take him up his offer.

A couple years later, Dennis is still my mentor even though I graduated. He got engaged, but broke it off a while back. And I haven’t had sex with him since Summer of 2019, but his son...well let’s just say we’ve been talking for a while. I might have to make a trip to him after this quarantine.