My Journey Into the Unnown

My Journey into the Unknown

Chapter 1 -- Masturbation and Chat Rooms

Let me start by say that my name is Dave and I was 32 years old at the time of this story, it was the mid 2000's I was living in Las Vegas and had just gone through a bitter divorce. My ex had been cheating on me for years. I knew about it but looked the other way. So yes, I was a cuckold but this is not a cuckold story.

A little about myself, I am a white male, 5' 6" tall, weighing about 145 lbs., and always thought I was decently endowed being about 5 inches. I was a swimmer in high school and college so I frequented a gym that had a lap pool 4 to 5 days a week to stay in shape.

I graduated college with a Bachelor's degree in computer science and at that time had a job in the Tech industry working from home.

After the divorce, I decided that I did not want to get into another relationship for a year or so, just wanted to get my life together. Of course, I had to have an outlet for my sexual frustrations so porn on the internet was my outlet. I found that when watching porn, I would be fixated on cocks, this got me started watching bi porn where I would fast forward through the video until the men were playing with each other.

I also frequented the adult bookstores a few times and check out the booth area. I was always able to find booths with the door open and guys with their dicks out masturbating. I was fascinated watching another man masturbate, I would just stand there and watch. Someone would always try to get me to join them, but I always declined.

I also discovered that the Web Browser I had my email through had all types of chat rooms from sports, gardening, entertainment, food, etc... to adult chatrooms for Str8, gay, bi, hell, you name it and there seemed to be a chat room for it. Therefore, when I was not online jerking to porn, I would frequent the chatrooms.

I enjoyed visiting the gay or bi chat rooms, I found chatting with other men about masturbation, sexual experiences, fantasies, or just my kinks always got me excited. I always end up nude stroking my cock and blowing my load.

My favorite chat room back then was "Las Vegas Bi Curious" where I loved talking with local men about jerking off. It was in this room I met Duke45.

I had been in the room for about an hour when I got a private chat request from Duke45, I always enjoyed the one-on-one chats with others so I accepted.

Duke45: Hi, how you doing tonight

Me: Pretty good and you

Duke45: Not bad, I've seen you pop up in the room for about 2 weeks now, we seemed to have the same interests so I figured I would see if you wanted to chat one on one

Me: Oh yeah, what are our same interests

Duke45: Jacking off

Me: Well, I do enjoy doing that

Duke45: Are you jacking now?

Me: Yes, does that excite you?

Duke45: Oh yeah, what's your cock look like

I had always shaved my body for swimming and still did, so I was pretty much hairless from my neck down.

Me: About 6 inches (of course a lie) cut and shaved

Duke45: A shaved cock makes me hornier than hell, you have any pictures

Me: No, sorry

Duke45: Are you married

Me: No, recently divorced, how about you?

Duke45: Married, wife knows I'm bi and loves to hear about my bi experiences, in fact she probably figures I'm beating off while chatting with someone right now

Me: Really

Duke45, Yup, she's at work and knows what I do when she's not here, hey take a pic and send

Me: So, she knows you're jerking right now

Duke45: Oh yes, send the pic

At this point, I was really pulling on my cock, fuck should I take one and send? I got my camera, stood in front of my mirror, and snapped a few pictures making sure my face was not showing. There was one pic with a long string of pre-cum hanging off my cock, which was the one I decided to send.

Duke45: Hello, are you still there?

Me: Yes

Duke45: I would love to see that shaved cock of yours, send a pic

Me: How do I send, email?

Duke45: Yeah, that works, Duke45@

God the naughtiness of this whole situation was so exciting, I had never sent a nude photo to anyone before, should I really do it? I opened my email, attached the photo, wrote, "Here you go" and hit send.

Me: sent

Duke45: Fuck, nice! Love the pre-cum

Me: Thanks

There was no response for about 5 minutes

Me: Lol, you still there

Duke45: Yeah, just jerking to your nice cock, ever tasted your pre-cum

Wow, what should I tell him? Ok I thought, what the fuck, do I tell him yes, oh what the hell

Me: yes

Duke45: fuck yeah, you tasting now

I scooped some on my finger and tasted

Me: yes

Duke45: Fuck you are going to make me cum

At this point I lost it and came

I cleaned myself up and turned off my computer, don't know why I did that, I just did not want to talk to Duke45 anymore that night. Of course, then I started feeling bad/guilty that I had sent the pic. Fuck, what am I doing, I have to stop this.

I did not log into the chat room the next night, but of course, the urge got to me the night after so I got naked and finally logged back into the chat room.

I was there about an hour when I saw Duke45 log on, just seeing his name pop up got me really excited and hard. Two minutes later I get the private chat request, stroking my cock I hit accept.

Duke45: You naked and stroking

Me: Yes

Duke45: Me too, been stroking to your cock pic for days now

Me: Glad to help

Duke45: Got any more

I did not want to send any more so I lied.

Me; Sorry but no

Duke45: Oh man, come on I know you did not take just one. How old are you?

Me: 32, you?

Duke45: 58, what part of town do you live in

I decided to give him a cross street that was a few blocks from where I actually lived.

Duke45: Wow we live close to each other

He gave me his cross street and fuck; he lives about 5 blocks from me

Me: Wow

Duke45: Yeah wow, send me another pic

Fuck why not, I went through the pictures from the other night, found one and sent it to him

Duke45: Nice, I knew you had more than one, have you ever jerked off with another guy?

Me: Once when I was in my teens, we just watched each other, there was no touching

Duke45: Do you fantasize about jacking with others

Me: Yes

Duke45: Feel like doing it with me, we live close and can do it at my house while the wife is at work

Fuck, this conversation was now going from just chatting to meeting, it had me excited, did I really want to do this?

Me: Don't know, I'd probably chicken out

Duke45: Let's meet, just for coffee

I was silent, didn't really know what to say but I had to stop stroking, didn't want to cum yet

Duke45: You still there, if we don't like what we see we can just have the coffee and go on our way, no harm in meeting

Me: When we would do this

Duke45: Tomorrow morning, are you free

Me: What time

Duke45: I take my wife to work at 9, could meet you at the coffee house just down the street from us around 9:30

I did not answer him for about 3 or 4 minutes

Duke45: Come on it is just a cup of coffee

Me: Ok, how will I know who you are?

Duke45: I'll be wearing a SF 49er's hat

Me: Ok

Duke45: Great see you then

I turned off my computer and got in bed, for some reason I didn't want to cum tonight, I guess I figured if I had I wouldn't have showed up for coffee. Had a hard time sleeping that night and was hornier than hell when I got up!

Chapter 2 -- First meeting

I got to the coffee house about 15 minutes early and grabbed a table outside, figured I could see who drove up with a 49er's hat and if I did not feel comfortable, I could get the hell out of there. He showed up right on time at 9:30, Duke45 was an older male in half-decent shape, a good 5 inches taller than me, did not look weird, just the everyday average looking male.

He must have sensed who I was because he came right up to me and said "Hi you here to meet me?"

"Yeah"

He smiled, "Wait here while I get a coffee." My heart was pounding, breath quickened, and all I could think about was should I just leave.

When he returned after a little awkwardness, we were soon talking about sports, hobbies and other various male-driven interests. My earlier nervousness had completely dissipated as we discovered just how many different interests and passions we shared.

He talked about his sex life, how his wife lets him explore with others up to a point.

As he spoke, I saw him shift his underwear through his shorts. I noticed the outline of his cock, hell it was hard to miss.

"And what about you?" He asked me now.

I blushed a little as he caught me looking down at his shorts.

"What about me?" My heart started beating faster as I repeated his question with a perplexed look. I told him how my ex-wife cuckolded me throughout our marriage and how I did nothing about it.

"Did you do nothing about it because you liked it, did it turn you on knowing another man was fucking your wife, cumming in her, did you ever fuck her when she came home?"

"No, I did not like any of that, I hated it!"

"OK, then what's your biggest fantasy?" He asked, watching me as he sipped his coffee.

I stared at him, "Ummm...hmmm..." trying to figure out what to say.

He was not going to wait "Do you fantasize about playing with guys?" He looked right at me and I saw his hand come over to the front of his shorts to rub the outline of his cock.

I could not believe he had just asked me that and then grabbed his cock so blatantly. I could not believe that I did not know what to say to him. My heart was thumping like hail on a metal sheet roof.

"I... I've never...ummm," those were the only mangled words I could get out of my mouth. Was he trying something here or was he just making conversation? Suddenly I was stricken dumb with the most exciting fear.

He watched me struggling with my thoughts, "Why don't we head to my house and have some fun, I live right around the corner."

I looked around for a second and said "sure."

"Which vehicle is yours?"

I pointed to my little blue ford ranger truck.

"Great follow me."

Next thing I knew I was sitting in my truck parked in front of his very nice two-story house. The front yard had desert landscaping and the front door had a big arch. He parked in front of his garage and we entered through his front door.

In his living room, I could see a nice pool in his backyard, he put his keys down and said, "Why don't you take your clothes off while I get us a couple bottles of water, in case we get thirsty."

I stood for a second unsure of myself, and then stepped out of my loafers, pulled off my tee shirt, then my shorts and finally my underwear, throwing them on a chair by the door.

I have to say standing naked in a stranger's house was one of the weirdest things I had ever done.

He came back still dressed and handed me a bottle of water. He just stared at me for a second then said, "Wow look at that fucking shaved little dick, let's head upstairs to the bedroom." I still could not believe I was naked with another man.

He pointed to the stairs and said "after you". I could feel him staring at my naked ass, which for some reason got me excited because by the time I reached the top I was as hard as I have ever been.

"Second door on the left", I entered his bedroom to see a big king-sized bed and two plush chairs with a little table in between, "fuck your dripping pre-cum already, have a seat in one of the chairs". I sat down, and then with a smile, he started to undress. Off came the shoes, then the shirt and shorts, when he stepped out of his underwear I was shocked at the size of his cock. It was long, thick, and veiny. It was a man's cock; I couldn't take my eyes off of it.

When I looked up at his face he had a slight smile, "you like?" I nodded but could not get any words out. I looked down as he started to stroke his cock, "Play with yourself", he was not really asking but telling me to. I started stroking while he removed the little table and sat across from me. "Spread your legs and slouch down a little", again not really asking but telling me too.

"Spread your legs wider, fuck look at those nice smooth balls, that smooth dick, fuck"! I could see real lust in his eyes as he spoke.

I was so excited I had to watch out so I did not cum too fast.

I watched him stroke up and down that large cock of his with one hand, and reached down and cup his big hairy balls with the other. Fuck, I had to stop stroking.

When I looked up at his face, he again had that smile, I could sense that he knew I was going to cum if I hadn't stopped.

We sat across from each other for about 10 minutes just watching and stroking. Being slouched in the chair, I had a very large pool of pre-cum on my lower stomach. I reach down dipping my finger in it.

"Lick it."

I thought my heart was pounding before. Fuck. Now it was downright racing!

I did as he asked.

"Lick some more"

I did.

"Keep going"

And I did.

As I was doing this, he started breathing heavy "oh fuck yeah, fuck here I cum" I watched as he shot rope after rope of cum onto his chest, fuck this guy could cum. I grabbed my cock and two to three strokes later I was shooting cum all over myself. Fuck that was one of the best organisms I'd had in a while!

He reached down and grabbed a couple hand towels he had on the floor, tossing one to me and using the other to clean himself up. I cleaned up and headed down stairs, as I got dressed, he stood naked watching me.

"Did you enjoy yourself?" he asked

"Yeah, I gotta get going" and I left, getting in my truck and heading home.

Chapter 3 -- Second Meeting

When I got home, I quickly jumped in the shower. All I could think about was why, why had I done that. Fuck I was not attracted to him, he was an older man, but that cock, it excited me, was I gay?

I was a nervous wreck all day. I did not log into the chat room that night, afraid I would have to talk to Duke45, as I laid in bed all I could think about was his cock, I fell asleep thinking of his cock and even dreamed about his cock!

The next morning as I took my shower I kept thinking of his cock and started to masturbate, I stopped before I came. I lathered up my cock and balls, grabbed my razor and started shaving my pubic area. I kept thinking how he like looking at my smooth cock and balls. Fuck why am I thinking of him, was I doing this for him?

I didn't log into the chat room the next few nights, but every time I masturbated, I would think of that cock, finally I got naked and decided to log into the chat room. I did not see Duke45 logged on, was I disappointed or relieved? I did not really partake in any of the conversations just kept waiting to see him log on, but he never did that night.

The next night when I logged on there he was, fuck just seeing his name got me hard. It was about 15 minutes later when he finally requested a private chat, of course I accepted.

Duke45: Hey there, you feeling better now.

Me: Hey back at you, I am fine, why would you ask that

Duke45: No reason, I had fun with you that day, how about you

Me: Yeah, I had fun

Duke45: Let's do it again

I grabbed my cock and started stroking, what should I say, fuck!

Me: Maybe, when?

Duke45: I'm not free tomorrow but I'm free the next morning, come on let's do it again

Me: Sure, same time?

Duke45: Yes, just come to the house

Fuck, I would get to see that cock again, it excited me so much that I came.

The next morning, I had made up my mind, I'm not going to do it again, by that night I was changing my mind, and by the next morning I had showered, shave myself and was getting in my truck to head over, fuck I was shaking all the way to his house.

I knocked on his door and waited till he opened, as I stepped in, I saw that he was clad in just a robe, "get naked and let's head up to the bedroom." I had only worn a tee shirt, gym shorts and my flip-flops, no underwear. I was naked in seconds again tossing my clothes on the chair. He just stood watching me with a smug smile. I turned and headed up the stairs and into his bedroom, all the while knowing he was behind me looking at my naked form. I should have asked him to get naked also, but I did not, being naked in front of a clothed person is such a turn on.

I sat in the chair while he finally discarded his robe. He stood looking at me stroking his cock, I was mesmerized again, could not look away.

"Come here, I'd like to feel that smooth little dick of yours."

I stood and walked over to him, he grabbed my hard cock, fuck just as he did that a large drop of pre-cum fell into his hand. "Fuck yeah, you like that don't you?"

"Oh yeah"

"Have you ever wanted to touch someone else's cock?"

"Yeah"

"Then go ahead, feel my cock, I know you want to."

I could not believe how nervous I was, my heart was beating out of my chest. I reached out and lightly ran my hand over it. God, it felt so hot, long and hard. I could not believe it; I was actually holding his cock in my hand. I slowly started to rub my fingers up and down, feeling every vein and bulge.

"Go ahead it won't break, stroke it!"

He started stroking me harder, so I grabbed his and did the same.

"Your little dick is really leaking now, grab some of your pre-cum and use it as lube."

I did just that, he released my cock, grabbed my hand and brought his cock over to mine, "stroke them together." Fuck, his cock was now pushed against my pubic bone, I was about two or more inches from his. The feeling of rubbing one's cock against another was amazing, fuck I was more excited now than I had ever been with my ex-wife.

His breathing was starting to get heavy, "let's get on the bed."

I turned but did not let go of his cock, he told me to lie on my back. This again was more of an order than a request. I let go of his cock and laid down on my back, "scoot up a little and spread your legs". He reached into the nightstand and pulled out a bottle of lube, poured some on his cock then took my hand "stroke me."

I just stared at his cock, stroking it, wanting to lean over and take it in my mouth. I was just about to do it when I felt his hand rubbing my cock and feeling my balls. "Fuck, you're so smooth!" He was not stoking me anymore but rubbing all over my smoothness. He got on the bed and straddled my leg. "So smooth, so soft."

God, it felt so good!

All of the sudden he jumped off the bed, "roll over, I want to see your ass." Again, I did not question him, just did as he said. He grabbed my hips and swung them, so my ass was now facing him. "Very nice." He reached under and rubbed my balls; my cock was now leaking all over his sheets. He started rubbing my ass, squeezing the cheeks, and then I felt him spread me open.

I let out a moan as he traced my opening, "don't fucking move", he then stepped back.

I looked over my shoulder and he was just staring at me stoking that beautiful cock again. He walked up to me again and reached under for my cock rubbing the head to get some of my pre-cum, he spread my cheeks again and started rubbing my cum over my ass. When he touched my opening, I moaned again.

"You like that don't you?"

"Fuck yeah"

He started to press his finger into me, and I started to move forward, "you don't want me to do that?"

I moaned again but did not want that, the look on my face when I turned to look at him must have stopped him. He smiled and said, "roll over again."

He then got between my legs, put his cock against mine, and started stroking.

The electric sensation of his cock rubbing against mine was something I still remember to this day. I could feel every massive vein in his shaft working against my cock, sending waves of pleasure through my body.

"You like this don't you?"

"Yes"

"Me too"

I reached out and took over for him. I couldn't get just one hand around our cocks, so I use both. My pre-cum was lubing both of our cocks, soon his cock was the only one moving, rubbing against mine. He started breathing hard again, I started to let go, "don't I'm almost there." He now put his hands on the bed, leaned over as if he was fucking me.