My Lifelong Journey

By Jacob Jackson

Published on Dec 9, 2018

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The following is a work of fiction that follows a young boy on his journey from curiosity and enjoyment of nudity with his friends to becoming a slut as an adult.

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A little background on myself. My name is Jacob and for as long as I can remember, I have been intrigued and fascinated by nudity. My own as well as others. Male or female, it just didn't matter. Nudity just excited me. After reading "The Emperor's New Cloths" where the Emperor walks around (unknowingly) naked and watching "The Beniker Gang" where in one scene a boy strips completely naked in front of three adults and acts like a wolf, fantasies of being naked in front of others overtook me. Problem is, while that was a very real fantasy of mine, I was a bit shy. While I wanted to be naked in front of people I was too timid to actually strip in front of others. So I figured I would start by trying to get others naked with me and then maybe I would be more comfortable getting naked.

I had a friend named Jordan, he was a year younger than I was. When I was 12 I came up with a game to get one of us naked that went along with "Legends of the Hidden Temple". With their being eight teams, we each picked four teams. When one was eliminated we lost a piece of clothing. Socks and shoes, shirt, pants, underwear. By the end of the game one would be completely naked. He was in favor with it, though we only played once.

It was down to the final competition, both wearing nothing but our boxers. His team won, and I had to slide off my boxers. I say there naked for the last five minutes of the show, then got dressed and left. We never played again though, but my interest continued to grow. I knew I had to find more people to get naked with and also to get them to be naked as well.

I wasn't sure what would happen when we were naked, I just really enjoyed the idea of being naked with others, and seeing as many people naked as I could.

My journey actually began a few days later with the start of Spring Break.

Shortly after waking up, a little before noon, I went over to my friend Colleen's house to see if she wanted to hangout. She was a year older and a grade ahead of me.

knock knock

"Hey Jake! What's up?" Said Colleen

"Nada, just wondering if you wanna chill." I replied.

"I've got friends over, but you can come over and join us."

"Who is there?"

"Just Brian and Susan"

Brian and Susan were twins, and two years younger. My mind started racing at the possibility with all four of us there.

"Sounds great. What should we do?" I asked.

"Doesn't matter. It's raining out so we're stuck inside."

"How about truth or dare" I though aloud.

"Sounds fun. I'm sure they wouldn't mind"

I followed Colleen in to her room and found Brian and Susan sitting on the floor against the bed.

"Hey guys!" I exclaimed.

"Jake!!!" Brian and Susan cheered!

"How about a fun game if truth or dare" asked Colleen

"That's boring" replies Brian

"Yeah" continued Susan

"Well, let's just make it dare then. And instead of giving dares to people, we write a bunch down on pieces of paper and pull them out of a hat. That way, we have to be care what we dare because we could get out own."

"Sounds fair" said Colleen

"Much more exciting" replied Brian

"And risky," worried Susan, "but I'm in."

We each got a pen and a small pad of paper and started writing down a dare. Wanting to see how far people would go, I started small

"Show off your underwear for 10 seconds" was the only "risky" dare I put in. It was pulled by Brian and he was a little hesitant but followed through. Everyone laughed, so I figured I'd push things further.

This time we each wrote five dares. I wrote out "Leave the room and take off all your clothes in front of someone, put them back on and come back" and "strip to your underwear and stay that way the rest of the day" when they were all in the hat it became obvious I was the only one daring such things, but since no one knew who it was from no one argued.

"Hey Susan, I got strip in front of someone... since we've seen each other plenty of times growing up, I choose you"

"I guess it's not a big deal" answered Susan. They left the room and I told Colleen that I had to strip to my underwear and showed her the card. Colleen giggle as I started to strip off.

When Brian and Susan returned, I was wearing only my boxers and was tenting.

"Nice place undies Jake" laughed Brian

"Yeah, glad its not me." Said Susan.

At that point I decided it was time for someone to get naked, so the next dare I wrote out was "strip completely naked in front of everyone and stay that was for the whole day" and Susan grabbed it.

"What the..." she said

"Rules are rules" said Susan

"Yeah. I've got to sit in my boxers" I protested.

"And I had to get naked with you" replied Brian

"But I'm front of everyone?" Said Susan

"Yup" said Colleen.

Susan slowly stripped and stood naked in front of everyone before sitting down again.

We decided to play one more round. Time to go for the gusto... "suck Jake or Brian's dick"

If I I pulled it... I would pretend it was something else, maybe get naked. But Susan pulled it.

"Gross" said Susan

"Cool" said Brian

"It was you wasn't it Brian? Just to get back at me for seeing you naked."

"No it wasn't, but I won't turn it down"

Colleen and I looked at each other.

"Just put it in for a couple of seconds and that will count" chirped Colleen

"Yeah, that will complete the dare and no way Brian really enjoys it since

it will be over before it starts.

Susan bowed her head and knelt in front of Brian and pulled down his pants. I was hypnotized by his cock. It was huge, even bigger than mine. Susan opened her mouth and took it in bobbing three times.

"There" she said.

She refused to play any more and both her and Brian got dressed and left. I followed them out and went home myself hoping I'd get to see Brian naked again sometime, but all three started ignoring me. They must have figured out I was behind all those dares.

As I went through high school, I stopped playing naked games with other kids, and nothing more happened until the year I turned 23.

My girlfriend and I had broken up and I was feeling exceptionally horny. I wanted a blow job and didn't care who gave me one. So I turned my attention to Craig's List. I figured getting a guy to suck me off would be easier, so I posted an ad in the M4M section.

It read: "Looking for a host who will strip me completely naked as soon as I walk in the door, lead somewhere else in the house leaving my cloths at the door and give me a blowjob with no reciprocation"

I received about six emails, but the one that stood out was from Terry. We walked back and forth, and he eventually convinced me to come over to his place which was the town over.

On my drive over, I thought about chickening out. This would be the first time I was fully nude with an adult male. But my hormones and horniness won out.

knock knock

The door opened and there stood a tall man wearing a t-shirt and sweatpants.

"Terry?"

"Hi Jake".

He ushered me in, the door shut and he immediately started taking off my cloths. First came my shoes, then my socks, my shirt, pants and eventually my boxers. I was completely naked. He started walking away and I shyly followed.

"First time with a man?" He asked.

"Yea, kinda nervous." I replied.

He pointed me to sit on the couch and got between my legs and started sucking.

"Ahhhh" I moaned. It was the best blowjob I'd ever had. I swear I came twice. When he was done he got up.

"That was great" I said.

"Come back anytime" he replied. He walked me to the door. I nodded my head knowing I'd never see him again. When I got home though, I shattered regretting not trying something with him... anything. I never knew I had the urge to play with another man. See them sure, but play with them? This was a new avenue for me. Had I emailed him again or returned to his house, I know Terry would have allowed me to experiment. But I chose to find someone else, and went back to Craig's List and posted again in the M4M section.

This time it said: "Looking to jerk off my first cock."

Since it was the middle of the day, I did not receive many emails. After an hour I finally got one from a gentleman named Chris.

"I get a lunch break in 30 minutes. Meet me at the forest preserve and we can get each other off"

This could fulfill two fantasies. Being naked in public and playing with a cock. When I arrived he was already there. I followed him deep into the woods and he dropped his pants. Following his lead I dropped mine. I reached out and grabbed my very first cock and started stroking it, as he did to mine. I came quickly and then lost interest in finishing him off. Wether it was cause my nerves of getting overcame me or my cumming cooled off my desire, I let go of his cock. He finished stroking himself off, we pulled up our pants and went our own ways.

While it was only a few minutes, I liked having another man's cock in my hand, and knew I wanted to do it again in a location where I could be more relaxed. Someplace inside. So back to Craig's List I went. This would be my third different man in a week, which kind of excites me.

My new ad read: "Looking for a host for my first real time."

His name was Jed. We talked a bit over email.

"What are you looking to do?" Jed wrote.

"Well for starters, I want to be stripped fully nude as soon as the door closes. Everything off. Socks, shoes, everything"

"I can do that," Jed replied, "what else?"

"Lead me away from my cloths to another room where I can jerk you off."

"Can I play with you too?"

"Sure," I said, "just let me finish with you first"

"Come over at 10 tonight"

I gave him my word and we set it up.

As 10pm arrived I had a mixture of excitement and nerves.

knock knock

Jed answered the door wearing only a bathrobe and motioned me in. With delicate care he stripped me naked. I left my cloths at the door an followed him upstairs to his room. He closed the door and removed his robe before laying on the bed. I laid next to him and grabbed his cock and slowly started stroking. After a minute, I don't know why I did it, I leaned in and took his cock in my mouth, bobbed once and took it out. I went back to stroking. A minute later I took it in again, again only bobbing once. I guess that was too much for him as he started stroking me even though I asked him to wait til I was done.

As soon as he took hold of my cock and started stroking, I released his and enjoyed what he was doing. Shortly after I came, for dressed and left.

Cumming was definitely what kept me from doing everything I wanted, so I needed to find a way to keep me from backing out. I knew it would have to be a group meeting, and kinda forced.

Back to Craig's List the next day I posted an add looking for two men.

It read: Trying again to experience cock for the first time. After I cum I lose interest in playing so I need a little help.

Only one couple emailed me. Mark and his partner Tim. We set up a meeting for later in the day.

When I arrived, I was greeted by two men already naked. They ripped off my cloths and pushed me to my knees and stood in front of me. I reached out and took each one in my hand and started stroking each. Mark moves closer and pushed his cock against my mouth and forced it in, and it stayed in while he face fucked me. I couldn't take it out if I wanted to. He came down my throat as his partner came on my face.

After they were done, they had me take a shower to get cleaned up. When I came out, they had invited friends over. A lot of them, at least five. This was more than I expected. I was terrified but excited at the same time. They had me lay on the bed where Mark started sucking me off. Two of the men stood on either side of me and I grabbed each of their cocks and started stroking. Tim straddled my chest at put his cock in my mouth and I started sucking.

Suddenly I saw a flash. Someone took a picture. As the three men cam and I recovered from my own orgasm, they showed me a Polaroid of myself from the chest up stroking two men while sucking another.

"This should help you experience all the cock you could ever want" said Mark. "You will come over every Saturday night, and do whatever we want. Or we will publish this photo for the world to see."

I did not want that. So I agreed to be their slut.

As weeks went on, I must have sucked off dozens of cocks. Some repeats, some new. Some old, some who had to be fresh out of high school at very least. I hoped they were not younger, but you never know.

I had become their personal slut... and I started to enjoy it, even look forward to it. They didn't even need the photo to blackmail me anymore.

They had given me what I wanted. The encouragement to do what I have always wanted since I was a child playing naked games with friends.

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