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Introduction:

This is the story on how I come to enjoy anal play
This is my first attempt at writing, so please provide me constructive criticism. If you're not curious about male anal play or you know you don't like it, then this is not the story for you. All names have been changed to protect the (not so) innocent.

I'm your typical IT guy that has always been sexually charged. I've always gotten my fair share of tail and my ex has even often called me a man-whore simply because of the number of women I've been with. However, I do not refer to myself as a man-whore -- I simply enjoy sex and I enjoy the variations you get in the routine with different women.

This is my story of how I've become interested in anal play.

The first time that I remember experimenting with anal play was when I was a kid, somewhere around 5 or 6. I had a fascination with my ass and the feelings that I got from playing with it. Even though I wasn't really big into playing with my "junk" at that point in time, I've always enjoyed the feeling I got from inserting items in my ass. Whether it was a finger, or in the case when I was 5 marbles, it's always given me that "good" feeling. I remember laying down for my nap and I had a container of marbles next to my bed. They were so nice and smooth. I'd put them in my mouth and swirl them around and they'd slide so easily next to each other. I was always playing with my butt and I had the bright idea of if they felt so awesome in my mouth, the feeling of them in my butt would be just as good if not better. So, as you can imagine, I removed one of them from my mouth, made sure that it was all lubed up from my saliva and tried to push one in my ass. Because my ass was dry, it didn't go very well, but the sensation I got from it was pretty incredible. I put a bit more saliva on my finger and lubed myself up even more to get it in. Once I was all ready, I tried to put it in again and low and behold it slipped right in. What a feeling it was once it popped by my sphincter! If one felt that good, more than one must feel better. Boy was I right! Before I realized it, I had counted 5 marbles in my ass and the feeling of them all in there sliding around together as I would squeeze was incredible.

After a few minutes of playing with the marbles in my ass by squeezing and shifting my body, that's when the problem appeared and the fear set in -- how the hell was I going to get them out? Well, things always come out when you go to the bathroom and take a #2, so a little bit of pushing like I do in the bathroom should get them out, right? Well, is 4 out of 5 bad? So then I got scared. It's pretty embarrassing for a 5 year old to tell his mom what he'd done and how to fix it… However, a bit of time on the porcelain throne and everything came out OK -- 5 out of 5 now out.

I think that experience kind of ruined me for a bit because I really don't remember much past that point in terms of any playing around with my butt.

Fast forward a few years, and that's when I started playing more and more with my junk (aka penis). I was probably somewhere around 11 when I really started exploring the sensations I was getting from playing with myself. I really discovered that my dick had other purposes than just to pee out of. There were a lot of things that lead up to this that really got me going.

Around that time, my mom and dad had a walk-in closet in their room. This closet was "off limits" as it was where things were kept that "weren't for kids". For instance, all the guns in the house were in there, at christmas time that's where they hid our gifts, and then I discovered the mother load. There was a shelf on two sides of the small room that was lined with the kind of boxes that you put magazines in and they were each dated by year - from 1971 to 7979. My dad had been collecting Playboy and Hustler magazines for years and they were all organized by year in these boxes. This was my first introduction to porn. I would sneak one out of the box and then put everything back the way I found it. I'd take the magazine into my room and hide it under my bed and pull it out when I wanted to do the deed. I would even read the magazines from cover to cover with my favorite part being the stories at the end of the book. This is where I first discovered that other people liked anal play as well -- but it seemed it was only the women that ever got their ass played with.

This made me wonder, are guys not supposed to like having their butt played with? Every time I read a story that a woman wrote and she talked about how it felt to have her ass fucked, it sounded very similar to what I was feeling when I would play with my ass. This kind of got me worried.

Society and the general closed mindedness of people that you find in most country folk in the midwest, I started hearing that only "gay" men like it in the ass. This concerned me. I didn't like guys (in that way), I really liked looking at women. Even in the pictures that I'd see in the magazine, the women were what I was looking at, not the guys. Sure, I'd compare myself to the guys in the magazine, but it was completely a comparison thing, never a desire thing. But the women, the curves of their breasts, the shapeliness of their asses, and the pussy. Wow, the pussy. I couldn't wait until I met one of those in real life because I never met one in print that I didn't like! I wasn't sure what I'd do with it yet, but from the pictures in the folds of the magazine and from the stories I was reading I was forming an idea. The anticipation of my first "meal at the Y" was really starting to take form. So with all of that, I couldn't be gay, right? Now you can call me confused.

About this time in my childhood, probably 12, my parent's moved me to a room in the basement of our house. I was ecstatic! I finally had my own room (previously I shared with my much younger brother) and it was away from where everyone else stayed. Now that I look back on it, I'm thinking that my parents did it more for themselves rather than for me. I would "hear noises" coming from their room at night and this move happened shortly after I had mentioned something to them one day. I wasn't stupid, I knew what they were doing and I was very intrigued to say the least. Everything that I've been reading about was actually happing in the room next to me.

Now that I had my own room, it was easier to sneak a magazine out and at night I'd examine it more thoroughly from cover to cover. I could play with my shit whenever I wanted and I had more freedom to explore my body. Even though there was the societal "no-no" of guys liking their ass played with, I still did it. The damn feeling of it was incredible, especially while I was stroking myself. I couldn't understand why I hadn't heard others liking this but I never mentioned it to anyone because I didn't want the label of being called the "gay guy".

As I said before, I grew up in the country in the midwest and the closest neighbor was a little under a mile away. The closest house with someone my age to play with was about 3 miles away. My grandparents lived about a mile away and my uncle (which is only about 9 years older than I) lived with my grandparents at the time. He helped them farm so it was just easier for him to live there than to get his own place. I would go over there and play pool, video games, ride around trails on 3-wheelers or we'd play with his model railroad. At the time Pong was the newest thing out (later to be replaced with the Atari). One time I came over and he was watching a movie on a reel-to-reel projector they had. He had taken out the projection bulb and simply put a flashlight on the side of the projector so it wouldn't project, but you could look through the lens to see the movie. This was my first introduction to porn videos.

I must have sat there for hours (or at least it seemed that way) watching the 3 movies that he had. Of course, they were all in black and white and they looked like they were filmed in the 40s. Realistically, they were probably filmed in the 70s but they were definitely interesting. I remember one of the scenes vividly where theres a woman hanging from a set of monkey bars by her hands and knees and a guy standing on the ladder on one side. She's bouncing back and forth while the guy is taking her. Not knowing if he was fucking her pussy or ass, I had two conflicting feelings while watching it. The primary feeling was what it would feel like if I was the guy and my cock was the one going in and out. I was envious to say the least. The other was the sensations she was feeling. I could see by the expression on her face that she was really enjoying it. That's where I got it in my head that I wanted to make EVERY girl that I ever had sex with feel that good. I think that movie was the single most important thing in my life that made me a non-selfish lover. Always please the woman and she will do things for you that she never thought she would (this is very important concept for later in my story).

The next scene was, you guessed it, an anal scene. Something that wasn't extremely popular back then, but there was still a scene on it. Damn, now that I think back, these must have been some pretty "raunchy" videos! The scene started as every scene does, chick walking in up to a guy some kissing and rubbing, etc. It quickly moves to the guy sucking on the woman's tits. I was watching intently at the care he placed on ensuring that he gave both of her nipples equal play and was fascinated by the way they perked up. Back then, my description of her breasts would simply have been "they're huge", but now in my older and more experienced days I'd say that she was a borderline C to D. The supple kneading of each breast and the sucking and nibbling on each nipple seemed to go forever. The way she would throw her head back and part her mouth while rubbing the guys head and back was a clear indication that she was feeling hints of ecstasy. Note to self: pay attention to breasts and nipples! The attention he paid to her whole body with kisses, sensitive touches and light drag of tongue all over seemed to only add to her excitement. And then the plunge between her legs. Kissing, licking, nibbling everywhere around her pussy really threw her into a show of bliss. Then the focus on "the little man in the boat". A full display of exactly WHAT made her lose her mind.

Then he licked her rosebud… WOW I thought. I could pretty much feel mine being rubbed with my wet finger (in my own mind). I knew exactly what she was feeling. He was now paying attention to not only her pussy, but to her asshole as well and the pleasure was evident in her actions. He would shift the focus of his tongue from her pussy to her ass and her writhing was unbearable to watch. Then he did it, he pushed a finger in her ass. Slowly sliding it in and out. Licking her pussy while fingering her ass. Wow. My mind was now spinning. Two fingers, she squirmed more and without any doubt all in pleasure. All of this ended in what appeared to be an orgasm -- or at least what I associated to what I experienced when I would cum.

He then rose up, removed his fingers and replaced them with his cock. Wow, exactly what I feel both when I'm stroking myself as well as when I'm fingering myself. Two of the best things that I've ever felt are happening in one shot of the camera. I wasn't ever focused on his cock in her ass, it was the focus of what she's feeling with something in her ass -- fingers or a cock. Same with the guy, it wasn't the fact that he was in her ass, I was concentrating on the feeling that he was experiencing from his cock being engulfed by something -- ass, pussy, mouth, hand or whatever.

Now, later in life, I've come to the realization that porn is all staged and they're acting. But at my young age and just being exposed to the "art" I had no clue. In my mind, this display was someone being recorded live and all the feelings of ecstasy were real. And I wanted to be that guy providing what he was. But, I also wanted to be that woman when there was so much attention being paid to her ass.

Later that night, I re-enacted the scene on myself by exactly what I was seeing in my head. What was in my head was everything that I was paying attention to in the movie. I was paying attention to the feeling I was experiencing when I was playing with my ass. First a wet finger rubbing the outside. Man that felt good. Just the pure sensation of something effortlessly sliding over every nerve ending around my ass. Then I slowly started inserting a single finger in my ass. Saliva wasn't proving to be a very good lubricant as it kept feeling as though I was drying up. So I went to my personal bathroom and got my lotion (often the lube for my masturbating). A little bit of lotion on my finger definitely felt better. Finally I got one finger slid in as far as I could get it. It felt good in my ass and the sensation of something around my finger always gave me a good idea as to what to expect around my dick when I finally meet my first pussy or ass. I've ever only had a single finger in my butt before and that's always felt good enough to satisfy my desires.

After seeing the movie and how her pleasure seemed to escalate as things went on -- one finger to two fingers and then progressing to a cock in her ass -- really enticed me. I figured what the hell, let me try a second finger. I applied a little more lotion to my fingers and rubbed the second one up. I then put both fingers at the opening of my ass and began to slowly push. It definitely provided a different feeling! There was a bit of not a pain, but a pressure that only added to what I've felt in the past. I liked it! Pretty soon I had both fingers up and over the second knuckle and realized that I was harder than I had ever been before. Another pump of lotion into my other hand and I started stroking like I've never stroked before. Holy shit the sensation was incredible. In my mind I not only was feeling the intense pleasure the woman must have been feeling, but I was also feeling what I envisioned to be exactly what the guy was feeling. Incredible. I exploded all over my stomach and chest with more spunk than I think I've ever shot before. My head was swimming. I've never felt an orgasm so powerful before and I was hooked.

My private sessions continued sporadically for the next year or so until I finally entered high school. Up to this point, I was in a small country school of about 20 kids close to my age, the girls were few, they were all neighbors (to an extent) and none of them were really sexual other than the random kiss -- which was a big thing. Again, keep in mind this is a country community in the midwest in the mid 80's where majority of the girls were pretty reserved.

High school though was another story. High school was "in town" where there were now a couple hundred kids and the boy/girl ratio was closer to 50/50. The chance of finding a girl that was less reserved and more sexually aware was much higher. Because I lived in the country, I had to drive myself to school. Busses didn't run back then to bring you to school so the state would issue a license to drive to and from school and school events -- something I abused quite often.

I had been talking to several girls in school and a couple of them started taking a liking to me (in the sense of boyfriend/girlfriend). However, there was one that I had heard rumors about that had "gone all the way". One night the high school team had a football game and I had asked her to go to the game with me. Jenny accepted and we agreed to meet later that night at the game. I hung out with the guys beforehand and when I got to the game Jenny was already in the bleachers. I went and sat with her through the whole game and we talked about small stuff in between watching the highlights of the game. After the game was over, she asked me if I could drive her home (another blatant abuse of my driving to and from school events). Of course I agreed and we got in my car to drive her home.

On the way, she was directing me how to get to her house by avoiding main streets so I wouldn't get caught by the cops (as I'd already had a reputation with them) and we ended up on a road outside of town which was no where near where I knew she lived. She told me to pull over to a hidden driveway where she said no cars would see us. When I finally pulled the car in and shut it off, she leaned over to kiss me. BINGO I thought, here we go! We kissed for a while and then some heavy groping started. I flashed back to my "notes to self" from the various movies I've seen up to this point and made sure to pay special attention to the kissing, kissing and nibbling on her ears and neck, and especially to the breasts and nipples. I had her down to no shirt and I could tell that she was pretty hot by this time and I was hard as a rock!

She then told me to sit back, slide my seat all the way back and take my pants down to my ankles. YES I thought as I did exactly as she instructed. She commenced to kissing me more and slowly stroking my cock and massaging my balls. This was my first experience with a girl and damn it felt much better than when I'm doing it to myself. She then leaned over and put the head of my dick in her mouth. Ho-ly shit! That was all I could say. I had never anticipated that this would feel as good as it did. The warmth of her mouth around my dick only made me lean back more. She was giving me an extremely sloppy blow job and as her saliva slowly slicked up my balls that made the massaging feel ten times better than it had dry.

Since this was my first blow job, I knew I wasn't going to last long and I wanted to prolong this as long as I could. Because I've always been one to verbally express what I like, I asked her to stop sucking me and give me a kiss. I insisted that she keep rubbing my balls though. That felt too damn good for her to stop but it was the kind of good that was going to make me cum. We continued to kiss for a while and I started to suck on her pencil eraser nipples, all the while she's still rubbing on my balls. She'd definitely done this before because there wasn't a spot that she didn't massage. Occasionally she would rub the underside of my balls and hit my perineum. Every time she did, that caused an audible moan to come from me. After a couple times of hitting it, she realized the hint and made that more of a focal point for the time being.

With everything going on, my body involuntarily slid forward on the seat so I could lean back more and my knees automatically separated. She went right back to sucking on my cock (as things were starting to lose their slipperiness). With the saliva factory now producing again on my dick and balls I was getting too close for comfort and I wanted to prolong as much as possible. She kept expertly massaging my scrotum and perineum. The only thing that I could do was try to think about the football game, car parts, anything to keep my mind somewhat at bay.

Then she did it. She slipped a finger further back and started rubbing my ass. I had completely lost control of my body by and and a definite moan of approval escaped my lips. My guess is that she took that as the green light to stick her finger in my ass.

I couldn't believe it, my first blow job and the girl had actually stuck a finger in my ass! I started to think that maybe guys liking their ass plaid with wasn't so unusual. Otherwise how would she know to do that?

She no more than got past the second knuckle and I completely lost control. I bucked in my seat like I've never bucked before. Hell, I half choked her when my hips come up and my dick rammed into the back of her throat. I shot cum in her mouth, all over her, all over me, and all over the car. Thank goodness for vinyl upholstery!

After that, she was done. She gave me a nice long kiss and then started putting her clothes back on. I was kind of confused and I wanted to please her the way that she had pleased me but she said with a wink that making me cum like that was good enough for her, for now. She really had to be getting home so her parents wouldn't be missing her.

Jenny and I dated for a little bit and things had progressed into full blown sex. She still loved blowing me and playing with my ass. I even had the opportunity to experience my first "meal at the Y" and I must say I was hooked. However, that's a story for another time since this one is all about how I got into anal play. Jenny liked to have a finger in her ass, but we never progressed to anal sex. I wasn't really disappointed as the pussy was definitely good, but I now yearned to experience the feel of an ass around my cock. A finger in an ass versus a finger in the pussy was a different feeling and I knew that it'd have the same effect on my dick.

I had more sex with other girls throughout my 4 years of high school to the tune of about 20 different ones. Most of them in neighboring towns (when I got a full fledged license) so I wouldn't get the reputation locally of being a man-whore (in a small town, it's very easy to do). However none of them were as open to ass play as Jenny was. I had guessed that Jenny was just more freaky than the average girl and I would have to accept that.

I've now accepted that I too must be freakier than the average guy. How does one keep fulfilling their "freakish" tendencies without obtaining a negative reputation? Confused… Everything kept going back to what had been drilled in my mind that only gay guys "like it in the ass" but it's clearly evident that I'm only into girls. My entire life I've never been attracted in the least to any guy. So, instead I resorted to pleasing myself.

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This is the end of my childhood. I've got part 2 ready to post and part 3 in the works. Please provide comments if I should continue or not. Thanks!
2 comments

anonymous readerReport

2012-04-23 00:22:13
You faggots are fucked up. Go stick a carrot up your ass. Oh by the way, you can't write either.

anonymous readerReport

2012-03-06 20:44:10
too much back story, good job though

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