Catfishing the best friend became a dipping of the toe [MM]
Several years ago, I became very bored, horny, and into online sex chat rooms. I was just becoming an adult and was eager for more and more ways to put my hard cock to use.
One day, I stumbled upon an older woman who was amazing to talk to. We chatted for about an hour before moving the conversation to Yahoo Messenger (throwback). On there, over the next few days, the conversation got hotter and heavier. I would send pictures of my throbbing member. She would send pictures of her long nails gliding along her pussy from her desk chair.
My best friend, Taylor, was equally as horny with fewer outlets. Still a virgin as he headed into adulthood, he was Mr. PornHub. One day while we were playing Xbox, I mentioned this woman I had been chatting with and encouraged him to checkout the chat room.
I left about an hour after. By the time I got home, I had a text from him saying “logging on.” I wished him luck and sprinted up my stairs to my computer to do the same. The chat room wasn’t too busy and, based on the logs of when people logged on, I was able to quickly tell which one was him.
At that point, I don’t know what hit me.
I’d never had any gay or bi thoughts. I was 18. I could’ve fucked a wall and been satisfied. But, for whatever reason, I chatted Taylor and acted like I was what I knew his type was: a bodacious 40-something, hungry for young cock. He immediately bit. I didn’t know where I was going with this. Maybe I was hoping to just help a buddy out and get his juices going, but I let it evolve. Eventually, he said that he needed to get some schoolwork done and asked if we could continue this on a chat site. I agreed.
Within minutes, I opened my phone to a picture of my best friend’s hard cock. I was mind fucked. I didn’t know how to react at first. I then sadistically kept the gag going and sent him a picture of a random MILF from the Internet and logged off.
That evening, he gave me the play-by-play of his masturbation session and sent me a picture to prove how much of a mess he made in his sheets. I told him I did the same, but left out which type of genitalia I used. I was enamored by my best friend’s cock.
We had discussed not having plans for the following day while we played Xbox the day prior. I woke up that following morning to a video of his throbbing cock and his balls slapping back and forth as he stroked his cock towards the camera. I immediately began sweating. Instead of responding, I sent him a text as me and asked what he was up to. He said nothing and asked if I wanted to swing by. His parents were out, but we could order in lunch and chill. I agreed.
My heart raced. Do I tell him? How am I going to contain my hard-on if he even mentions his recent MILF encounter?
I knocked on his door maybe 15 minutes after I agreed, my penis still tucked into the waistband of my sweatpants. He wore a similar pair of grey joggers as he opened the door. We plopped down on the couch and started watching ESPN. I asked him what’s new and he started to detail how amazing the site I recommended was. He provided vivid detail of this sexy woman who chatted him late into the night until he finally couldn’t stop his river from flowing. I glanced over and saw he couldn’t contain his pants situation once again. He was tenting mere inches away from me.
He caught my stare and I asked if he wanted me to step outside while he took care of that. He nervously laughed and said, “Maybe she’ll help me later.” I almost smirked and said, “Or ‘she’ could help you now,” but bit my tongue.
I ended up taking a big risk anyway.
“Do you want to throw a video on the TV and just do it at the same time? It’s not really gay or anything. Trust me, it’s taking a lot for me to keep in my pants after seeing her too.”
His jaw dropped. I saw his mental wheels churning.
As he kept thinking, I said, “Fuck it,” and slid my sweats down and popped my cock out the button hole of my boxer briefs. I elbowed him and said, “Let’s just try it.”
Little did he know, I already knew what to expect out of his package so he didn’t need to stress. We seemed to be of similar length anyway.
As I began to stroke, he finally did the same, first rubbing over the pants before sliding it down and letting his cock slap his chest. I nearly came on the spot seeing this cock that I dreamt about the evening prior up close. Confusing thoughts of my sexuality began to swirl, but I was feeling incredible.
It didn’t even take a minute before we started just looking at each other and not what was on the screen. We’d never discussed sexuality. We were both straight. But something was happening. Without even asking, he grabbed my cock and began to stroke me. I slid closer to him and reached my hand below his ass and squeezed him tight. He paused to pull his shirt off and I did the same. What the f was happening.
He finally spoke.
“I knew it was you, by the way.”
Too stunned to speak, I moved away for a second, paused, and then attacked his cock. He knew who he was teasing. We had crossed some unspoken line, but clearly we’re both in on it. We didn’t kiss, but began just aggressively groping each other. I pushed him off the couch and onto his knees and buried my face in his ass. I was a man possessed and starting rimming him like I knew what I was doing. I then slid around on the floor and put his cock in my mouth. In just 24 hours + 10 years of friendship, it felt comfortable enough.
He moaned and said he was getting too close. I stopped, laid down on the floor, and asked him
to suck me too. I grabbed his buzzed head and shoved him down further on my cock.
I then rolled over and asked him to touch my ass. I had once fingered my ass and hit the prostate perfectly for an incredible orgasm. I hoped he could stimulate that same spot and he quickly did. With a gentle finger in, he rubbed until he found the spot and I yelled for him to stop before I exploded.
I then uttered what only a “straight” man would say when possessed: “You can fuck it if you want.”
Source: reddit.com/r/Erotica/comments/12k8i7g/mild_catfishing_became_first_time_18mm