I had always had an open mind, as a kid having watched porn far too much and been in way too many chatrooms. But now that I was away from my parents and enrolled at a large public university in the Southeast, I could finally explore any desires that I may or may not have. As a former baseball player and at nineteen years old, I was in good shape at 6’2 and just a little extra weight that I carried in my ass.

I had heard about Craigslist in an accounting class when an Alum had come to guest lecture but once I went home from class that day I learned about the “other” side of Craigslist and went down a rabbit hole. Finally, I landed on the Casual Encounters section, specifically the M4M section. I didn’t find anything interesting the first day except there were multiple postings about “Daddy” types. For reasons I cannot explain that suddenly caught my interest and led me down another Internet rabbit hole and the seed was planted.

For a couple of months, I would browse Craigslist randomly when bored and sometimes would be curious about if people really met off of there. One Thursday afternoon, after smoking a joint, I found myself scrolling through Craigslist once again and eventually into the M4M section.

I’m not sure if it was the high or the fact that I was in a dry spell with the ladies but one ad caught my eye: “Daddy looking for discrete younger friend to guide.” Upon reading that the fifty-nine-year-old man who was married and was looking for an inexperienced younger guy to help guide into the pleasures of male-to-male contact, my seven-inch cock became hard. My breaths became deep as I watched myself click “respond” and I sent him an email.

“Hello, I’m Bobby, 19, a freshman at State, and your ad really caught my eye. I have no experience but I have often found myself curious but very nervous to really explore.”

I included a picture of my body in just boxers but without showing my face. I was incredibly anxious sending it and kept thinking, “You aren’t actually going to go through with this.”

PING - I heard the unmistakable sound of an email coming in and I panted as I looked and saw it was a response from him.

“Bobby, I’m very glad you decided to reach out to me. What are you interested in exploring? I have a very safe place that I would love to help guide you. I am very discreet about this part of my life but your young body looks delightful. I hope you will give me the opportunity to guide you. - Tom”

My cock was twitching and I could hear my heart beating fast as I seemed to be having an out-of-body experience as I watched the words appear on my screen and realized I was immediately responding.

“Tom, that was a fast response. I am really not sure what I’m interested in exploring but I’ve read some stuff and watch even more, and I’m always very curious on Daddy/son stuff or really any older man/younger man stuff. I also have an affinity for roleplaying with people online but I have no real experience. I think I’d like to start with stroking and maybe sucking but I’m just not sure yet. I hope I’m not wasting your time if you’re looking for more I certainly understand - Bobby”

I was panting and nervously sweating when I hit send and decided to close my laptop and play video games.

After about fifteen minutes, curiosity (and a raging hard cock) got the best of me and I opened my laptop with the intent to watch porn, cum, and then forget about Tom. Upon opening my laptop, the screen was on my inbox and sure enough, Tom had responded.

“Son, you may call me Sir or Daddy when emailing me or in private. I think you are exactly the type of boy I’m looking for. You need a little push, some guidance and the opportunity for freedom to explore. Would you be interested in meeting me at my secret apartment? My only expectation is that you show up if you say yes. Other than that we do not need to plan too much and I will not be forceful…this time ;)"

I shuddered and groaned and realized I had been stroking reading his response, it continued.

“Here is the address. I have time at noon on Wednesday. If you want to join me, simply respond ‘Yes Daddy.’ - Tom”

I exploded upon reading the ‘Yes Daddy’ part, and instantly I slammed my laptop shut and cleaned up before my roommate got back.

I hopped in the shower and told myself, “You are straight, you don’t like guys. He’s probably some creepy perv,” and I decided then that I was not going to respond to him and that was a fun quick fantasy, no harm done. I got out of the shower and got dressed for a party. My decision was made, I would not be responding.….for the weekend I didn’t think about Tom at all and was busy chasing girls.

That chase turned out to be all for naught as once again another weekend came and went and my dry spell continued. By Sunday afternoon my teenage hormones were in overdrive and I was horny when my roommate said he was going over to his girlfriends and was probably going to stay the rest of the afternoon.

“Finally I can stroke in peace,” I thought as he left and I heard the door lock, my laptop was opened immediately.

I browsed around and decided to watch porn. The first video I found was an older man and younger female and immediately thoughts from Thursday popped into my head. Nervously I opened and reread the last email from Tom. Again my heart raced and my cock twitched as I slowly dragged the cursor to hit “reply.”

“Yes, Daddy,” I typed and hit send.

Immediately I was the most anxious I had ever been. What had I gotten myself into? What was going to happen? Was he going to turn out to be a crazy person? What was I going to wear?

"WAIT, really what am I supposed to wear?" I thought and looked down to find myself stroking once again. The thought of what to wear seemed dumb but something inside of me felt the need to meet his approval and expectations but I didn’t really know what those were.

I nervously hit “reply” again and typed, “Daddy I realized that I don’t really know what you are expecting me to wear, any insight would be helpful as I’m quite nervous about this….”

PING there it was another message had come through before I finished my thoughts. I opened Tom's email and my jaw dropped with what it said.

“Son, I am very pleased to hear from you. I thought you may have gotten cold feet. I look forward to Wednesday. I expect you there at exactly noon. You may wear sweatpants or gym shorts with no underwear and a tight shirt that shows off your wonderful chest. Do not respond to this, see you on Wednesday - Daddy”

My heart beating out of my chest as my mind raced. How could he possibly know that I wasn’t sure what to wear? "Why do I feel this need to follow these instructions?”

I wondered as I then realized I was two pumps from cumming and then I erupted, spraying several thick ropes of seed flying onto the computer screen. After cleaning up, I realized that I truly was excited for this and that the next few days were going to drag by.

After several more ejaculations and an agonizing few days, Wednesday finally arrived. I looked up directions to the address and was pleasantly surprised that it was only fifteen minutes away and from what I could tell, it was in a nice area.

I showered and then pulled on gray gym shorts that were the tightest ones I had, although they were still a little baggy, and a tight tee shirt. And I was ready to go…

As I pulled in the parking lot, my hands were shaking and there was a lump in my throat. My mouth was dry and all the voices in my head were telling me to leave but my body was on autopilot as I parked my car. I checked the time and it was 11:58.

As I got out of the car my body was trembling and I wasn’t sure I could walk but once again my body went into autopilot as I walked to the building. His apartment was on the bottom floor of a split-level building, so I slowly walked down the stairs holding on to the railing as though the world was tilted. Checked my phone and it was exactly 12 as I knocked on the door….

The door immediately opened and there he was wearing khakis and a dress shirt that made him seem professional and trustworthy. I must say, almost anyone would find him attractive if you’re into silver foxes, he had salt and pepper hair, about my height, a bit of a dad bod with a big smile on his face as he held the door open.

“Come on in, boy.”

I tried to speak and the words fumbled. “Thank you, Sir.”

He closed the door behind me and I looked around and saw it was a clean two-bedroom apartment with just the bare necessities there, clearly this really was a secret place. Tom stood there watching me intently.

“Boy, I can tell you are nervous. But I’m not going to hurt you. I’m going to train you and guide you. Why don’t you come sit on the couch?”

He motioned for me to walk and as I passed by him I felt his hand on my lower back and then felt it as it slid down until it was on my ass and I heard myself quickly inhale audibly.

I stood next to the couch frozen, not knowing if I should run or what to do or say. I was lost in a million thoughts until I felt him squeeze my ass firmly and say:

“Daddy is very proud of you for following all of his instructions so far. Continue standing, boy.”

As he sat down and spread his legs apart I could see his bulge and instinctively licked my lips but didn’t speak.

He continued, “Do you want your next set of instructions?”

For some reason, this question put me at ease as I looked up at him. “Yes, Daddy,” I whispered.

He motioned for me to spin around. “Show me your body slowly and then I want to watch you take your clothes off.”

I nodded as I began immediately, as my back was facing him I felt both hands grab my ass as he said, “My oh my, son, this ass is juicy.”

I moaned feeling his hands gripping my ass like it belonged to him. Then he released me to continue turning.

“Get naked, boy,” Was his command in a very firm voice.

I saw him adjust his bulge and my eyes got big as I noticed how big it appeared to be. I quickly stripped as he began exploring my body with his hands.

“Daddy had found himself an obedient sexy boy. Why don’t you sit down beside me and help Daddy get more comfortable?”

My breath was deep and staggered as I said “Yes Daddy” softly and sat down next to him.

I could feel his eyes on me but I couldn’t tear my eyes off of his bulge in his khakis. His big hand slid into my inner thigh and he gripped it quite firmly.

“Look at me, boy, stare into my eyes and let your hands do as they please.”

I don’t know why but that caused me to moan as I looked up into his eyes and I didn’t think I was moving. However, within seconds, I felt my hand sliding down his thigh towards his bulge.

“That’s a good boy. You love being told what to do, don’t you, boy? You have needed a Daddy to help, haven’t you.”

I nodded slowly maintaining eye contact as my hand found his bulge and I gasped slightly. He let out a soft moan and that was the encouragement I needed as I started rubbing his bulge more confidently; wanting to look but knowing I was told not to.

As was becoming the custom, Daddy seemed to know exactly what I was thinking. He took my hand off and I made a sad face.

“I know you’re so desperate to see it, aren’t you, boy?”

I said nothing but nodded as he stood up and shuffled directly in front of me.

“Based on how much your cock is bouncing I know you’re enjoying this.”

I briefly looked down and realized my cock was doing a dance all on its own.

He continued, “Now be a good boy and help Daddy out of his pants.”

I kept looking up at him as I felt for his belt and zipper and slowly fumbled with it. Finally I got it undone and slid his pants down slowly. Because I was maintaining eye contact, I didn’t see it but I felt his thick cock spring out of his pants and smack me beneath my chin and I yelped both in excitement and surprise,

He laughed as he looked down at me. “Does my boy want to look at Daddy’s cock now?”

I nodded.

“Look at it, boy.” He smacked me in the face with it.

I finally got to take in its beauty. It was a little longer than mine but it was thicker than I had seen in person. I kept staring at it as I heard him say, “You may touch it, boy.”

I was lost in the moment as I reached out and held it, the weight of it was shocking as I started to slowly stroke it.

Daddy moaned, “Look at my stud, boy, stroking Daddy’s cock like an absolute pro.”

I kept stroking him for a few minutes until he sat down beside me and we started stroking together. Him stroking me and me stroking him as best I could.

“My boy has the most beautiful big balls, I can’t wait to watch you explode”

I moaned as he pumped my cock and then he stopped and in a much more aggressive tone said:

“Boy, why the fuck did you stop stroking me?”

He looked angry and I realized I had lost myself in my own pleasure.

“I’m so sorry, Daddy, I just I’ve uh well uh…” I tried to form sentences but decided to just start stroking him like my life depended on it. He watched me but at this point, it was clear my pleasure didn’t matter on the same level his did.

After stroking for a few more minutes he said, “Daddy is going to cum soon. I'm going to stand up and cum all over your cock and those big balls, and then I want to watch you use it to stroke yourself. Keep stroking me while I’m standing until I say stop.”

Hearing this I moaned much louder than I anticipated and he laughed, “Mmm I love an eager cum slut,” as he stood and started stroking him with one hand and rubbing his balls with the other.

He moaned and said, “Okay, get ready for your reward.”

He pushed me back against the couch with my legs wide and he stood over me and almost like I knew what to say I moaned:

“Cum all over my cock, Daddy; I crave feeling your seed!”

That caused him to grunt and then unleash a torrent of hot Daddy cum all over my cock, balls, and stomach. I didn’t even have time to reach down as we both stared in amazement as my cock twitched and without hands I came all over my stomach.

Panting and covered in cum I looked up at him, “I’m so sorry, Daddy. That’s never happened.”

“That was one of the hottest things I’ve ever seen. Let me get you a towel.” He walked into a bedroom and came back with a towel.

After cleaning up, I sat there exhausted and smiling when I heard him say, “Shit, look at the time! It’s 12:50, my reservation is only until 1. You’ve got to go,” as he hurried me to get dressed.

“Daddy will email you soon. I hope you enjoyed this. You are going to be so much fun to train.”

For some reason, this seemed to be the biggest compliment I had ever received and I moaned, “Thank you, Daddy.”

As I walked out and headed up the stairs, there was another older man walking down the stairs. I kept my head down still embarrassed at what I had done. Out of the corner of my eye I saw him do a double take as he walked by and then I realized he was walking into Daddy’s apartment. As the door was closing I heard the man say:

“Jesus Tom that is a stud walking out with cum on him. When you gonna sh…”

The door shut and I didn’t hear the rest. I did however look down and realized a rope of cum had splashed down my neck and was clearly visible.

“Who was that? What did Daddy mean, 'reservation'? I can’t believe I have cum dripping down my neck.” Those were my thoughts as I got into my car.

I drove back to campus, took a shower, and realized I had to submit a paper. As I opened my laptop, I saw an email from Daddy with the subject line, “Next Time.”

Part 2 coming soon. Please feel free to leave comments and tips. I would appreciate a follow and a like.