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….