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A quick warning to anyone who’s about to read this: It’s definitely not going to be a story that’s very well written. It’s not that I’m aiming for a poor quality story, but I write about as well as a gimp dances and I don’t really know how I’m going to go about telling all this. I figure I’ll start off telling a bit about myself and then just write down whatever comes to mind.
Well, I can see how people would see me as a loser if I had to break down my life in a few lines. On the plus side I have a good social life, a steady girlfriend, and I don’t look all that bad. Then again, the down side brings my skinny figure, the fact that I barely have enough money to put gas in my piece of shit car every month, I still live with my parents, no job, and no real future as far as I can see. I know it’ll never happen, but what I really need about right now is something real good to drop down into my lap to get myself some money. That’s besides the point though. I’ve got a real easy going personality. Most people mistake my being a passive person for me being a real pushover. Not true though. What I am though, is rather shy. A bit of a pussy too, in the sense that I tend to back out of things a lot.
My sex life hasn’t gone any farther than the basic heterosexual exp with a few ladies until just a couple days ago. Well, that’s slightly not true. My sex life, with other people, was the basic heterosexual deal. By myself I’ve experimented around with my body since I was about 16. Only lately, in the last several months, have I really gotten into it though. Other than masturbation, I’m mostly talking about anal play. I was sixteen when I first slipped a finger in. I didn’t go too far into it then though, I’d mess around with little objects that I could find around the house. Markers, hotdogs, a couple fingers, and other things along those lines. Like I said, I didn’t really get into it then. Hell, until I was nineteen I’d only indulge in some anal play maybe once every couple months.
About a half of a year ago though, I’ve been doing these types of things a great deal more often, and pushing it so much more than I ever had before. Usually when no one’s home I’ll go into the bathroom with some lotion and lock the door. Either that or I’d wait until everyone was asleep and do it. Most of the time I’d wait till no one was home though.
A big reason I do that is because of the mess that always came with this type of fun.
– That brought something to mind, and keep in mind I’m a little ignorant to many aspects of sex, why is it that I’ve always got to stay in the bathroom to do anal play? The way things typically go is this, I’ll take something in the bathroom with me, let’s say it’s my Mom’s dildo, and I’ll start to pump it in and out of me for no more than thirty seconds and then I can’t help but not hold back my urge to take a crap. Now up to this part, it seems somewhat logical to me. So after I get off the toilet and clean off the dildo, which always gets very dirty, I start back up again. Normally the second time around, it’s a minute into it. Then I’ll have to shit again. This’ll happen a good three or four times before, each time I’ll get on the toilet while leaving the toy in the sink until I can get up to wash it off some, I can just use the toy anyways I please. Now I may not be a bookworm when it comes to reading up about anal play, but I’ve never heard of anything like that at all. I figure if I asked anyone about this, they’d just tell me that it’s very common for me to get the sensation of needing to crap. That’s why I’ve tried holding out, not letting up after the first, or even after the second time on the toilet and just keep pumping it in and out of me. Almost every time I do that though, it ends up coming out on its own making either my hand, the floor, or a towel very dirty. I’d love for anyone to respond to this and enlighten me. I’d be up for any suggestions, discussion, whatever. –
As I said, I’ve been pushing things farther than I ever have lately. The biggest thing I ever use to use was my Mom’s dildo. It was about as average as it could be, just like my dick. About six inches long, maybe six and a half, and not all that wide, but not skinny or anything. That was very big to me until recently. I stepped up to things like bananas, necks of bottles, and the biggest yet are these very wide, and somewhat short, plastic bottles of soap I have in the bathroom. What sucks the most about them is that they are just as broad on one side as they are on the other side. So I had to be good and worn in before I tried. Now, keep in mind my idea of very wide isn’t all that wide. It sure as hell seems like it when I’m shoving it into my ass though.
Normally when I did it late at night, as I’ve grown a liking to over the last month, I tend to work it in and pretty much just leave it in. I still make sure to keep a dark colored towel around which I use every time, but it’s nothing like what goes on in the bathroom. What I’ve taken a liking to is getting myself loosened up, then taking the soap bottle and using it as a butt plug. I’m not sure it works as well as a butt plug should, but one thing I do know is that it’s a real challenge to get it in and poker oyna then sit in my computer chair while it’s lodged into my ass. For the first few minutes of me sitting there, I have some pretty funny looking posture. It eventually finds a place to stay in there. From there, I’ll pay some attention to my dick. I’m a big fan of Literotica, EasyGals, and if I’m running out of things to look at, I’ll go to TheHun.
It wasn’t until almost a year ago that I started looking at things other than the basic porn. Now, I go straight to Gay, Tran-sexual, and Fetish. Those are the things I read the most. Sometimes I’ll look into Non Consent, Anal, and Incest every so often when the title seems appealing. All the reading and viewing of these genres is probably what provoked me to get into the anal stuff. And eventually, I made myself a name on Yahoo that I decided to go around chat in. I’m sure you remember me mentioning I back out of things a lot, well, you can imagine how many times I was online and someone that lived near me wanted to hook up and I just closed the IM box over the last four months. Until a couple nights ago, but I’m getting to that. If I went into those chats more than once every couple weeks, I imagine no one would believe me when I told them that I’ve never been with a man, yet over a four month time period, I was looking for a first. I would like to clear up that despite my Odd thing is that I wasn’t looking for anything special. Well, in a sense I was. Not special, but specific. Every time they found out I’d never been with a guy, they told me how they’d treat me really good, make sure I like it, blah blah blah. That’s just not what I was looking for. I wanted someone to say “I want to fuck you and then leave.” I didn’t want to go around saying that though. Don’t ask me why, but it just seems… weird.
Then on Tuesday night, it happened. He messaged me after I took my pager from my usual “Invisible” to “Available”. Out of nowhere came a message that I figure would wind up just like all the rest, nowhere. With his consent, I actually copied the transcript just so I could put it on this. If you’re not in the mood to read it, don’t sweat it. I’m sure if you skip over it, you can figure out what all was said.
tulsamaster_9: its been a couple months since i talked to you
(I don’t remember ever talking to this guy. He was on my list and seemed to remember me though.)
newbottomboy19: Ya’. I know. I don’t really get online all that often.
tulsamaster_9: thats cool
tulsamaster_9: so whats up?
newbottomboy19: Not much. What’s up with you?
tulsamaster_9: sitting here looking for something to do. or maybe i should say someone to do lol
tulsamaster_9: when was the last time a man fucked you real good?
tulsamaster_9: u there?
newbottomboy19: Sorry bout’ that.
newbottomboy19: Well, never really.
tulsamaster_9: No one pop that cherry yet???
newbottomboy19: Not as of yet.
tulsamaster_9: you have a face pic?
tulsamaster_9: your ass looks like it just got rammed for hours in your pictures
newbottomboy19: That bottle is the biggest fucking thing I ever got in me, so it made me swell up a little bit that night.
tulsamaster_9: you have pictures of your face?
newbottomboy19: Not on this computer.
newbottomboy19: I have some on my other computer though.
tulsamaster_9: i dont fuck ugly people
tulsamaster_9: go get on your other computer.
newbottomboy19: I will here soon.
newbottomboy19: Right now I’m doing these Window’s Updates.
newbottomboy19: I’ll get on the other comp as soon as I’m done though.
(That’s a lie. I don’t have another computer. I just didn’t feel like telling him “You can’t have my face pic.”)
tulsamaster_9: what do you look like?
tulsamaster_9: im 37, 195, 6’0 brown hair blue eyes
newbottomboy19: 19, 6’1, 165, brown hair, and brown eyes.
newbottomboy19: as soon as I’m through with this*
tulsamaster_9: are you ugly?
tulsamaster_9: because i can get any boy i want so i dont waste my time with ugly people
newbottomboy19: Eh’, I’m pretty normal looking. I’d like to think I’m not ugly.
tulsamaster_9: you done yet?
newbottomboy19: I’m just installing it all now.
tulsamaster_9: what are you doing tonight?
newbottomboy19: Nothing really.
tulsamaster_9: want to meet up with me?
newbottomboy19: Where do you live?
tulsamaster_9: 51st and riverside u?
newbottomboy19: 21st and Mingo.
(We were about six or seven miles away from eachother.)
tulsamaster_9: you know any secluded areas we can go to?
newbottomboy19: Not really, do you?
tulsamaster_9: what about any alleys?
newbottomboy19: What’re you looking to do anyways?
tulsamaster_9: i just wanna fuck you and leave
tulsamaster_9: I want to fuck you hard
newbottomboy19: Hmm.. that’s exactly what I’m looking for too.
tulsamaster_9: canlı poker oyna so lets hook up.
tulsamaster_9: i need to see your face
newbottomboy19: Here, I think I might have a pic on this comp. I’ll put it on my profile.
tulsamaster_9: damn not what I was expecting!
tulsamaster_9: no, in a good way
tulsamaster_9: most people who dont put there face in profile look freaky
newbottomboy19: Ok then..
tulsamaster_9: you look fucking hot though
newbottomboy19: So you’re really wanting to hook up like tonight?
tulsamaster_9: yep but first
tulsamaster_9: do you have ads?
tulsamaster_9: aids or anything like that?
newbottomboy19: No no no, I’m clean.
newbottomboy19: Now that you bring that up though I want to use protection.
tulsamaster_9: good answer
tulsamaster_9: i believe you to so i think i will fuck you bareback
tulsamaster_9: to ease your mind though ill pull out
tulsamaster_9: cum all over your face
newbottomboy19: How big are you anyways?
newbottomboy19: It’s been a while since I even did any anal play so I’m pretty tight.
tulsamaster_9: Im about 7 inches long and ive got really nice girth
tulsamaster_9: dont worry ill make it feel really good when i fuck you
Well, that’s enough of that. Copying and pasting the conversation seemed like a really good idea that night, and earlier today, now.. I realize it’s not the best way to go about writing this out. Of course, there was a little bit more of the conversation where we worked out some details. I ended up agreeing to meet him at a Quick Trip and find a secluded park. Just for the record, this guy drove a pretty expensive truck and I couldn’t help but wish that he’d try to pay me to do something. Sucks that he didn’t though. So we agreed on the place, I bought myself almost an hour to get ready and drive there. Why an hour just to drive three miles you may ask? I wanted to clean myself out so that when it came time for him to fuck me I wouldn’t have to shit and he wouldn’t get so messy. So my plan was to first use the bathroom, then find something small to stir things up inside me with, then do it again a few times until I thought he could fuck me without my shit getting everywhere. I made sure to use something very small so I could keep tight for him.
So it was about fifteen till midnight and I started my way out of the house trying not to wake everyone up, got in my car, and drove to the QT. When I got there, I saw the truck that he’d described to me with him leaning up against it. The picture he’d shown me on the net was of his face only, so when I saw him standing there, all of his stats made sense. He was exactly as he’d described to me, semi-tall and had plenty of weight. Much of which was in his belly. I got out of my car and got in the passenger side. Without a word, he was in the drivers side and starting off towards a park we thought might be empty enough for us.
I saw him glance over at me a couple times initially, but still we hadn’t talked. That all changed once he started to unbutton his pants. After he’d wiggled around enough and got his pants and boxers down he looked over to me and said “Why don’t you come over here and get your first taste of some cock.” I unbuckled and leaned down in the seat until I was face to face with it. “There you go. Wrap those bitch lips around it.” I won’t lie to you. I wasn’t eager in the least bit. Fact is: I was nervous as fuck. I surprised the hell out of myself just by showing up. Now that I was there, I couldn’t really do much about backing out. So I brought my hand out to the base of his shaft to touch my first cock, other than my own, for the first time in my life. He wasn’t lying about being thick. It’s true that he would need some coaxing before his cock became erect, but even being as short as it is, it was one thick piece of meat. I’m jealous. I’d been stroking it for a good ten or fifteen seconds before I finally licked my lips and brought them down to the head of his cock. First I started in with my tongue, getting it acquainted with every bit of the head of his penis. Then I brought it along side his cock and started to move my lips down his shaft. I only went down a couple inches on his semi-hard cock, then brought my head back up and repeated this several times, each time keeping my tongue on his cock to message it as best I could. I hear that guys give the best blowjobs, which makes sense, but in my case, I knew I wasn’t doing anything for this guy that hadn’t been done better for him before. Oh well though.
So I kept dropping my lips down a couple inches on his cock and then back up, sucking hard each time I rose up. Somewhere in the process his hand dropped to the top of my head. After a minute or two he started pushing my head down a little bit more than it was before which I resisted at first. There was a reason I only dropped down a couple inches, I was kind of afraid that if his cock touched my throat, it’d gag me till I vomited. I did give in a little bit though, dropping my head down three internet casino or four inches on rigid cock. I figured it was a good compromise. I always read about guys deepthroating cocks and what not, but the few times that he did try and push my head down farther than it was, it hit my throat and provoked several long and hard gags that I didn’t think I would recover from. Thankfully he let up and just stayed satisfied with what I was doing. After another minute or two the truck started to slow down until we came to a stop. “This looks like a good place” head said as he started lifting up on my shoulder suggesting I get up.
I leaned up from his crotch and looked around at a completely dead park. It was great. The way the park was made, the only neighboring road to the park was a long ways away, so if we did see anyone coming into the park while we were busy, we’d have time to zip up. “Ya’… where do you wanna’ go?” I said as I looked around for any benches or tables.
“I figure I’ll just lay you out in the bed of my truck.” With that he turned off the lights and made his way to the back of the truck. I followed him back to witness him drop the tailgate and motion for me to sit up on it. I jumped up into a sitting position while he let his pants go letting them drop down around his ankles. “Take your pants off man.”
Yep. No way out now. “Ok.” I kicked my shoes off real quick then dropped my pants to the ground. He leaned down to pick up the pants and slid them under the small of my back as he suggestively pushed my chest back until I was laying down on my back with my ass hanging out of the bed holding up my legs as best I could. I was a little turned on by the situation. Unfortunately it didn’t show. I was so nervous, my dick was as small as can be. Beside me was a small tube of lotion that he’d brought with him. He started off applying some directly onto my ass with his finger rubbing it in. He didn’t really press into me right away. He went back for a little bit more lube before he brought his finger back and started to push it in. It was a really awkward situation. I was just laying there flat on my back looking up at the sky while for the first time in my life my ass was being fingered by someone else. In time I started looking more at him than the sky. He took his finger out for a moment them came back with both his fingers starting to push in. This wasn’t painful or anything, but not near as smooth as just his one finger. Normally when I do two fingers, it’s not much. I have rather slender fingers, this guy on the other hand had the fat type.
No more than thirty seconds later, he took his fingers out and started lubing up his cock. After a moment or two of this he stepped up to me. “You ready?”
Trying not to sound as scared as I was I replied. “Ya.”
“Alright then boy. Get ready to take this cock up your ass.” He said placing the tip of his dick against my virgin hole. I closed my eyes and bit down on my lip bracing myself for what I imagined to be some serious pain coming my way. He started pushing in very slowly. Right from the start I knew he was going to stretch me out and cause me some real pain. It took a few seconds of pushing before the head of his cock popped into my ass. He had the type of cock that had a huge head on it. Lucky me. So with my teeth clenched I let out a muffled groan. I could feel the pain pulsating throughout my entire body. He kept pushing the rest of his shaft into me until he was about five inches deep into me. He stayed there for a minute and started wiping the lotion off along the side of my leg. When he’d got rid of most of the lotion he brought his hands up to my ankles and lifted my legs up a bit higher than they’d been when I was holding them. He kept them there as he started to bring his cock out to about the head then push it back in. He did this slowly for a short while letting me adjust to the size of it. For this I was very grateful.
He eventually started pushing in deeper until I could feel his hair tickle my ass every time he touched me. It felt like his dick was pushing into my stomach each time this happened. Then his pace started to quicken a little bit. I was still feeling an intense pain when he pushed into me, but I was yet to feel any pleasure. “So how’s it feel boy? You like me ripping open your ass with my fat cock?”
First thing that came to my mind was to lie to him, but I didn’t like it. “It really hurts” I said to him between groans. The way I said it made me sound kind of constipated..
At this point he pushed his body against me hard sending a sharp pain through my body “You just need to learn how to take cock like the bitch you are.” He pulled back hard and started pushing in faster than before, sending just a little bit more pain throughout my body than earlier. “Come on boy get into it.” He said slapping his body against mine. “Jerk that cock.” I obediently brought my hand to my soft dick and started rubbing up and down as best I could, considering it was about as small as it could get. It took me a minute to get it just a little bigger with him slamming into me, but once I did things got a lot easier from there. My ass even started to hurt less. And just like I’d read, his dick started to rub something inside me that did feel pretty good. Made my cock grow to its full potential. So there I was vigorously jerking my cock while he slapped his body into mine about as fast as he could.
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