Pandora's Tight Box

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Anal initiated to anal obsessive.
1.4k words
4.08
113.9k
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As I recall it was 7 years ago, almost to the day that I was first initiated into the world of anal sex. Let's just say it was an eye opening experience and is now one of one of my biggest obsessions. I guess in order to explain it I should go back a little bit further in time, back when I was younger and more "innocent" shall we say. When I was around 21, I can remember a boyfriend asking me to masturbate for him and I was so embarrassed that I just wouldn't do it, who knows maybe I just wasn't comfortable with it then, and well, look at me know.

I knew from the first moment I saw him that I wanted to feel him inside me, but I never would have guessed at that time that I would eventually crave him deep in my ass. I used to follow him around a little, watching, creaming my panties and then when I was home alone I would franticly finger my sopping pussy while I fantasized about him fucking me and licking my clit. Eventually, I had my chance and one drunken night I jumped all over him and can still remember how wet my pussy was waiting for him to touch it. I was impressed that he went right for the gold and stayed clear of my small breasts and his fingers were good but I wanted so much more. So, basically we quickly got down to business fucked for a while, which was great but I was pretty drunk, so I ended up finishing him off by swallowing his load. I still remember him tapping on my shoulder, I guess trying to be somewhat of a gentleman letting me know that he was going to cum, and I can still remember thinking, "what is your problem, let me taste you already". I've never been much of a spitter and I suppose after that there would have been no going back, even if I had wanted to.

So, after we had fucked a couple times he brought up the subject of toys, and amazingly enough I was all over that. Little did I know that was the beginning of our small fascination with everything adult. Anyway, a couple times after that, I'm not sure if it was boredom or just wondering what he could get me to do, he brought up anal sex. I said no at first, adamant that it wasn't going to happen, and he pretty much tried to blow me off after that, so I caved, said we could try it once, but I wasn't really interested. I can remember that like it was yesterday too, well, parts of it anyway. I'm sure that I was wet, I'm sure that ate my pussy, I'm sure that he fucked my pussy for a while, I'm sure I sucked his cock for a bit, and I'm also sure he was ready for it, probably just appeasing me until he could get my ass ready. I was still so unsure, but I wanted to please him and I was suppose slightly curious. I was bent over the bed, doggie style was our favorite position, anyway he began to stretch and finger my ass. I remember that I wasn't so concerned about the possible pain associated it, but was more worried that I would be embarrassed if I were to get shit on his dick. He got pretty excited and fingered my ass harder and I didn't think it was so bad, but then the next thing I knew he was anxious and pressing his hard cock on my puckered hole. I tightened at the intrusion, and that only served to egg him on.

I kept moaning over and over that it wasn't going to fit; that it was too big, and there was no way it would go in. Then, suddenly I proclaimed, "Oh it went in!" I begged him to just leave it there so I could get used to his cock invading me and he tried for a second and then started stroking me, telling me it wouldn't be long. It was that long, well, maybe 30 seconds or so, but some of the longest of my life. Afterwards it was so sore and big and he loved staring at the large hole he had left behind from fucking my ass so hard with his dick. Just like having a mouth full of cum, there was no more saying no to the anal sex, after that he was obsessed and had to have it all the time. I'm not sure when he eventually converted me to an ass freak too, but I grew to need it. After a while I would even beg for him to bury his cock in my ass, and he would stick other toys in me, either my pussy or my ass, or I would masturbate while he fucked me in the back door. For those of you that don't think it's pleasurable, I don't know what to say, perhaps it's not for everyone, but I had the most incredible orgasms with him deep in my ass, more powerful than anything else I have ever experienced.

Over the next 6 years we did a lot of things, doggie style remained my favorite, and after I got a boob job I found that there was nothing more arousing then getting fucked in the ass with a dildo in my pussy and watching my new larger chest in the mirror. Even better was when he would get really turned on and pull my hair while he hammered me, and I loved watching the look on his face and I loved seeing the look on mine.

Funny, he never really did like me licking or sucking on his balls, but he loved when I would lick his ass, actually he used to beg for it, and I used to love licking it while I would watch him jerk off. Of all things, it's sort of crazy because I loved seeing his dick in his hand, perhaps because unlike my first experiences I loved masturbating in front of him, for some reason it felt so intimate.

It's been over a year since he's been in my ass, he's moved on to someone else, and even though I love it, I'm not sure if I would be comfortable doing the things we did together with someone else. It was amazing, the best sex I've ever had, and I still get wet thinking about it. Even now, my pussy is soaking, and I am rubbing my swollen pussy lips together thinking about it. As much as I don't want to at times, I can't help but get nostalgic and when I do, I need to feel it in my ass, I finger myself and think about all of the sinful things we used to do together and how he we used to fuck in public, and I miss it so much. I wonder if I will ever experience anything so powerful again.

Another thing I loved was tasting my pussy on his lips and I guess for that reason and the simple male fantasy he always wanted to see me with someone else, we never did get around to it but we used to talk about it, the whole threesome thing, and I wasn't so sure about that but it did get me wet thinking about it, and what even made me more horny was thinking about someone else sucking my clit while he fucked my ass, and there are days I wish we would have done that too. Even naughtier is sometimes when I feel really full and have to go take a crap I get so horny and wet and then as I'm going I spontaneously orgasm. I'm not sure if I should thank him or hate him for introducing me to a world of pleasure that I don't know if I can do with anyone else. I wonder at times, if he still thinks about those days, with his cock buried deep inside my tight asshole, as he tried to split me in two, and if grips his hard cock and rubs it as hard as I rub my swollen clit. It's then right before I give in to a blissful orgasm that I wonder if he still thinks about me and if he misses it as much as I do.

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AnonymousAnonymousover 1 year ago

This is A NUMBER 1 Most Realistic Story I have read in all of Literotica. This came across as absolutely honest, unfiltered, and unexaggerated. I especially appreciated the side comments about feelings about specific acts. Her honesty and apparent lack of distortion to "make her look better" are a delightful breath of fresh air. I wish all Literotica stories (especially anal) were as honest!

AnonymousAnonymousalmost 19 years ago
Love The Tight One!

Wonderful story! I can only hope it is all true for her! I know I would love to help her keep things going like this!

songman60songman60almost 19 years ago
A very torrid "tail"

Kudos to you, tight box. A very well-written story on one of my favorite activities as well. I get the distinct impression he is gone now. If you miss it so much, I will proudly volunteer to substitute in his stead.

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