Boy's First Time

by Dillon

21 Sep 2017 2783 readers Score 8.3 (32 votes) PDF Mobi ePub Txt


**Sorry it took so long to come up with Chapter 4. I sorta hit writers block, lost interest, and then lost my password etc etc. But now, I'm back. So hopefully you all like the new stuff as much or more than the previous 3 chapters. As usual, comments and compliments are welcome. I'm all about customer service..lol**


After our unplanned free show at the fishing hole, we continued on to the mall. It was a fairly uneventful mall trip. We did the typical things, hit up the
food court, waste $20 at the arcade, wonder in all of our favorite stores, just window shopping.

" While we're here, I really need to go in Game Stop and see if they have any PS3 controllers I actually like" said Justin.

" Okay.. I'm gonna go get a refill on this Dr.Pepper and go to the bathroom while you do that..I'll meet you over by the escalator" I replied.

" That's cool, I shouldn't be long.. don't go flirting with any other boys while you're all by yourself" Justin said with a laugh.

" I'll try not to, but you know me..attention whore extraordinaire" I replied sarcastically.

Walking back into the food court, still fairly sore from the night before and earlier that day, I had that feeling that everyone knew what I had been up to..like being naked in front of your whole class or something.

I noticed a lot of guys taking double looks, longer looks than you give the average person just walking by..but whatever I said to myself as I kept walking to the food court.

I'm at the drink station, topping off my drink when I feel a hand on my shoulder, and before I can turn to look I hear " Rough night huh?"

Startled, I turn around to see it's one of the men from earlier, from the fishing spot..

" Haha, yeah, just a little bit I guess" I said while blushing.

" Oh now he's self conscious & shy, but not while being absolutely RAILED in public, knowing he's being watched.. That's strange" The man said with a grin.

" Yeah..I guess in the moment, all of that goes out of the window..that was a first for me" I stammered.

" No reason to be shy now, I've already seen you in all your glory..So you here alone?" The man asked.

"No, he's here with me, he's somewhere on the other side of the mall, some video game store..not my style, so I came back over here to wait and kill time" I replied.

"Well, I have a little time to kill myself.. would you like to take a little walk, maybe somewhere more private?" He asked.

" Uh..uhmm..S-s-sure.." I nervously replied.

" It'll be OK, not like I'm gonna kidnap you haha, I just wanna walk and talk..get to know you" He said.

" Well, I guess that's cool.. I'm supposed to meet him in a few minutes, but he'll live..He can just text me when he's done with his shopping" I replied.

So me and the unknown man walk toward the food court exit, I notice him looking me over, probably undressing me with his eyes, and god knows what else.

We walk outside the mall, and across the parking lot to this little area with picnic tables, which I guess was also the smoking area.

" So, what's your name? How old are you? Tell me about you" The man asked enthusiastically.

" My name is Dillon, and I'm barely legal..I'm above the age of consent..Umm..still in school.. idk..I'm bad talking about myself" I replied.

" Wow, what a cute name, sexy.. As long as I won't go to jail messing with you, I'm good" He said with a chuckle.

" Well, who said you were going to get to mess with me?" I replied with a smirk.

" Please, no one knowingly lets 2 men watch them have sex in broad daylight, in public, and then not put out" He said.

" Well, according to him, we're official, BF/GF..So.." I replied.

" You guys are also what? 17-18? He means that right now, cause it's new, that's all that keeps a young guy interested in other young guys, cause it's new and exciting..they never actually carry on relationships,it's going to be all sex, when he wants it.." He replied.

" That may be true, but right now, our relationship is like..2 days old..I have no complaints so far" I replied.

" So, you answer some questions for me now..How old are you? What's your name?" I asked.

" Sure thing cutey, I'm Andrew, 33 years old.. I have a boring office job,computer programming IT crap..Divorced 2 yrs ago, no kids..and know how to treat a boy right" He said with a laugh.

" We'll that's good to know for future reference..Do you live around here?" I asked.

" Not immediately in this area, I live about 30 minutes away, but my job is right around the corner from where we met earlier..I usually take my lunch down there, relax, maybe rub one out..if it's a nice sunny day.." He replied.

" That's cool, that was my first time ever even going down to that spot..it's a good spot for outdoor play" I replied.

" Yeah it is, and I've never seen anyone there until today, when my co worker and myself saw you and your friend.. It was too hot to not jerk to, and I would have felt bad not leaving a tip for such a performance..that's what that $100 was for" He said with a grin.

" Well I'm glad you enjoyed it, but he took the money..that's what he's shopping with right now" I said in a pissed off tone.

" Here's another $100, just for you cutie..keep it to yourself, you deserve it..and there's more where that came from" He said with a grin.

" Wow, thanks!And I catch your drift, you want to be like my sugar daddy? But then your note said you wanted to watch me and him?" I asked confused.

" I'd love to have you all to myself..But I'd also pay to watch you two go at it" He said.

" I gotcha.. He seemed real interested in getting paid for this..so you may get that experience soon" I said.

" I sure hope so, my friend is married, super sketchy, he won't be involved,he doesn't want anyone to see or recognize him." He said.

" Oh okay.. Yeah I can understand that..I'm not out, and don't want anyone finding out..especially parents etc" I said.

" Me too, we can be extremely discrete, yet daring at the same time" He replied.

" That's what we've been doing so far" I replied.

I felt a vibration in my pocket..I had a phone call from Justin, and like 20 texts..

" Shit..it's him..and he's pissed..I need to answer this.." I said..

" Hey what's up? You done?" I asked.

" Yeah, I am..I'm standing here at the door, seeing you over there sitting with some guy, all off to the side..WTF is this about? You seriously talking to other guys?!?!?" Justin said angrily.

" I'm just talking to someone, killing time.. what is wrong with you?" I replied.

" Whatever..I'm going home..have fun with your new friend" Justin replied even more angry.

" What'd he say? That didn't sound good..." Andrew said in a concerned tone.

" He saw us over here by ourselves, and apparently thinks I now belong to you" I replied.

" Shit, I wish you did.." He said with a laugh.

" Just trying to lighten the mood, sorry..but really..That's that young guy bullshit mentality I was talking about earlier" He added.

" Don't get me wrong, I like what me and him have, or had..But I really didn't take it that serious, it was fun,exciting,new,all sorts of things rolled into 1" I replied.

" Yeah, it's mainly about sex though right?" He asked.

" I think so..I mean,this all started in a late night game of truth or dare and snowballed" I replied.

" Oh really? That's interesting..So you guys became official after a game of T or D?" He asked.

" Basically.. T or D, very passionate and steamy sex, making out.." I replied.

" He wouldn't act that way if he really cared, he just wants to fuck..all the other stuff is just decoration for the experience I'd put money on it" He replied.

" You should call him, and talk to him.. if that's what it is, you can still fuck him, but let me treat you good.." He added

" Yeah.. I'll do that.." I replied.

" Here's my phone number, call or text whenever.." He said.

" Okay,cool. Well, I'm gonna go.. I'll call him on the walk home and see what's what..Thanks for your advice Andrew" I said with a innocent smile.

" Not a problem, been there and done that enough to know..Just glad I could be of help to you, be careful on the walk home cutie" He said with a wink.

As I was walking away, I looked back at Andrew several times, he never took his eyes off me..I could feel him undressing me with his eyes, fucking me with his eyes..

Andrew had a very hard, seductive vibe..Like he was a legit Daddy, who really knew how to treat his boy. And the way Justin acted, just proved to me he's not a Daddy, or he would have came and disciplined me, not acted like a bitch on the phone.

" Well, here goes nothing.." I said to myself as I dialed Justin's number.

Of course he didn't answer..So I sent him a very long text, asking him what the deal is..As I continued my walk home.

20 minutes later, I'm within sight of my house, when I feel my phone go off.. I look down to see it is a text from Justin..

" Hey..I got in way over my head with you..We don't have any business being in a relationship..the sex is amazing, but I'm not gay..I like girls too..but I wanna mess around with you..Can we be that? fuck buddies?" He asked.

" Just so you know, it's not like I really thought we were serious..it was fun to think it, act like it, but I knew better..I knew it was just sex.." I replied.

" Sorry for being a jerk earlier..are we cool?" He asked.

" Yeah we're good..but just so you know, I'm not gonna be your on demand booty call if we're not exclusive to each other..I'm sure you're still with that girl too.." I replied.

" That's cool..If either of us wants any, we will text ahead of time and arrange something..Deal?" He asked.

" Deal.But whatever you or I do, protection is a must with whoever it is..Deal?" I replied.

" Double deal.Done. Hey, I gotta go..Mom's home..Talk to you later" He said as he hung up on me.

" That was weird, and went amazingly smoother than expected" I said to myself with a laugh.

I continued my walk home, to find my parents were gone yet again, note on the fridge- " We're going to be gone a few days, a family emergency, We will call you tomorrow and fill you in".

Awesome, the whole place to myself for god knows how long..

I should call Andrew right now, and let him show me how a real man fucks..The thought of it sent trembles down my spine,along with a tingling all over my body.

Nervously, I dialed his number...

" Hello?" Andrew answered.

" Heyy, it's Dillon..From earlier.." I replied..

" Oh hey! How are you? I really didn't expect to hear from you this soon, or at all" He replied with a laugh.

" Yeah haha, I too your advice, and called him on the way home..and it was exactly as you said..Just wants to be fuck buddies, his booty call" I said.

" I knew it..But hey, you got some good sex out of it, and had no expectation for a relationship right?" He asked

"Yeah pretty much.. We're probably still gonna fuck more, but who knows when..he seemed shady on the phone..and I know he has a girlfriend too" I replied.

" Well, if you want, we can be new friends, if you know what I mean"He replied.

" Yeah, I think I know what you mean..Or I wouldn't be calling you" I replied sarcastically with a laugh.

" Ooh, so you're cute AND a total smartass? Sounds like someone needs a spanking.." He replied in a seductive tone.

" Oh yeah, I've been real bad today Daddy, you wouldn't even believe" I said innocently.

" I would believe it, I witnessed a good chunk of your naughtiness with my own eyes..if you were even naughtier, it's going to take a lot of spanking" He replied.

" Trust me, it's gonna wear you out to discipline my ass Daddy" I replied.

" Well, I can't wait..And you're such a good boy, quick learner, already calling me Daddy..didn't even have to be told" He said.

" So, you want to meet up tonight?" He asked.

" Sure! I can't seem to get enough, total anal virgin Friday, Saturday 5pm total cockwhore.." I replied

" Well, it's only been 2 days,and a grand total of how many times?" He asked.

" I lost count, maybe 2 or 3 times" I replied.

" You're far, far from being worn out..You're not even broken in boy" He replied.

" So, what are doing tonight Dillon?" He asked.

" Idk, you tell me, you're in charge Daddy" I replied.

" Well, if it's okay with you, I thought we could have an actual date..I'd like to take you to a nice dinner, get to know you more..if that's okay?" He asked.

" Anything is okay with me, but we can't go anywhere around here? The discretion,secret thing?" I asked.

" Yeah, I know, It's not a big deal..We will go out of town somewhere no one knows us.." He replied.

" Cool with me Daddy..I'll get a shower and get ready, I'll call you when I'm all fresh and clean for you" I said.

" Yeah, get real good and clean.. Daddy wants you looking and smelling good" He said with a laugh.

The end.


Sorry if this was long winded, but I had to set up Chapter 5, in as much detail as possible. Forgive me. Chapter 5 will be out soon.Comments,complaints,compliments  welcome!

by Dillon

Email: [email protected]

Copyright 2024