tagAnalHow I Fill My Ass

How I Fill My Ass

byrockhard231©

Gone are the days of having a nice and tight asshole. I was fine with that though, because I loved the feeling of stretching my ass out.

I remember the first time I played with my ass. I was a 18, naked, hiding under the covers. I didn't know much about masturbation other than I liked doing it. I was fingering my pussy slowly, taking in the feeling of my hairy mound, the juices around my finger. As I started to slide my finger in and out at a faster pace I adjusted my hand to get as deep as I could with my finger. I kept up my pace, feeling the tingling of an orgasm on its way. As I was now furiously fingering my wet slit, my other fingers hung below, and in the fury of my masturbation, brushed against my asshole. A whole new tingling feeling was sent through my groin. It felt amazing. I kept one finger in my pussy and lightly brushed my tight little hole with my other finger. Again, an amazing feeling came from what felt like deep within me. Curious, I slowly rubbed around my tight puckered asshole, as I slowly slid a finger deep into my vagina. The feeling was sensational, and after some slightly more aggressive rubbing, my body was tense as an orgasm washed through me. I lay there, with a finger still in my pussy, wondering how else I might play with my newly found hole. Little did I know, that day ignited a passion that led to some real hot and steamy fun.

The next time I played with myself after that I was even more curious. I started slow again; caressing my boobs, pinching my nipples, rubbing my hand up and down my whole vagina. But then I went straight to my asshole. I started to rub it, while still playing with my boobs. It felt great but I wanted more. I slowly slipped the tip of my finger into my asshole, then quickly out again. It was so tight, and felt so good to tease. Wanting even more, I fully slid my finger into my ass. My tight hole enveloped my finger, and I could feel deep inside me like never before. It was such a full feeling, I couldn't help but rub my now pulsating clit. I slowly moved my finger around, sliding it out and in at different lengths to feel different levels of being full. It didn't take long before my body was convulsing with an orgasm, as my ass clenched even tighter around my finger. Longing for that feeling, I didn't stop there.

Over the next few years I learned lots of ways of how to enjoy playing with my asshole. It wasn't long before I started inserting more fingers. I loved to violently finger my ass with just one finger so I could stretch it to make room for more. Lube was a necessity for me. I loved the feeling of sliding things up my ass. I went through a phase of sticking random objects into my ass. It started with a toothbrush, which was much longer than my finger. It reached deep into my ass, which made fingering my pussy at the same time orgasmic. I then tried a hairbrush, slightly thicker than my fingers. It stretched out my asshole just enough to love it. I would fuck my ass hard and fast with that brush, barely having to touch my clit to bring on an orgasm. If I was feeling really naughty, I would stick the toothbrush deep into my ass then fuck my pussy with the brush. Filling both holes felt so good, satisfying my need to be filled. Anything round found its way into my ass; pens and pencils were long and fun, make-up tubes were slightly thicker, good for short, fast fucks. One of my favorites was a bottle of shampoo I had. It came in a long thin bottle, and although it was hard to insert, once I got it inside my ass, I could lower myself almost completely down it. Taking that bottle stretched my asshole more than my fingers could at the time. Taking it deep while being that stretched out left my pussy dripping and begging to be played with. I spent many showers with that shampoo bottle in my ass.

I'll never forget the first time I did anal. I was 19, and had a boyfriend for a few months now. He was as horny as I was, and any free time we had was spent with his dick in my mouth or his face shoved between my legs. I told him I liked to play with my ass, so the next time he played with me, one hand kept fingering my pussy, the other snuck down, circling my clenched little asshole, before he slid his finger in. He slowly fingered my ass and kept pounding my pussy with his other fingers. Having someone else fill both my holes felt amazing, and a tingling feeling came deep within my ass, spreading to my pussy as my body clenched around his fingers and an orgasm came over me. After that he was addicted to my asshole too. He loved to go down on me, then lick from my clit, down my slit to my asshole, where'd he circle it, lubing it up enough to stick a finger in. He would then go back to licking my clit while fingering my ass, leaving me helpless to my orgasms. After that I had to let him fuck it.

The next time we were going to have sex I told him I wanted him to fuck me in the ass. He was overjoyed, but we were both still nervous about it. His cock was thin, maybe 6 inches in length, but rock hard. I took it in my mouth, rubbing my tongue against the head of his cock. I made sure to be sloppy as he went balls deep into my mouth. After some sucking I then asked him to lube up me. He went between my legs, focusing on licking and teasing my waiting asshole. I lay on my back on the edge of the bed; legs spread in the air and told him to fuck me. He pressed the head of his cock against my asshole, before slowly entering with the rest of his cock. It took a little bit of stretching at first, but he was soon balls deep in my ass. It felt so full as his rock hard cock slid in and out of me. He started to pick up the pace, as his erect member slid deep into me, then quickly back out again, leaving me longing for more. My pussy was now leaking with excitement, running down and adding to the mess around my asshole. I slowly rubbed my clit as he picked up his pace again, really fucking my ass now.

He held my legs in the air as he pounded my ass, hard and fast, balls slapping against me. I matched his pace on my pulsing clit, as I could feel we were both close. As my asshole was now stretched and used to the abuse, he fucked harder and deeper, his cock filling my asshole, making me scream in pleasure. I couldn't take it anymore, the fullness of his cock in my ass and my fingers against my sensitive clit, and orgasm like no other came over me. My asshole clenched tightly around his cock, a tingling feeling washed throughout my whole body, as my muscles clenched, my pussy erupted my juices out, spraying my boyfriend in front of me. This set him off, and after another hard pump into my ass, I felt his cock swell as he released his cum deep into my asshole. Feeling his hot load inside my asshole set me off again, as I rubbed my clit, my body convulsed, and more of my juices squirted out of me. He pulled out of my ass as I lay there, squirming as the final convulsions pass through me. My still gaping asshole leaked his cum, as it ran down my ass, adding to the pool of my juices below me. My bare pussy slowly leaked the last of my juices, as I continued laying there in our mess, overjoyed with the sensation of having my asshole filled. That was to this day, the best orgasm I've ever had.

Unfortunately, that relationship didn't last, but the feeling of having my asshole fucked did. After having tried anal I decided I needed a toy to help me when a guy wasn't around. I tried a slim glass dildo; it was hard and smooth, but too easy to glide in and out of my ass. I wanted a challenge. I next bought a realistic looking 8 inch dildo, complete with balls and everything. I had fun with this one. The head of the dildo would start to stretch my ass, as I slid it in taking all 8 inches. This cock filled me like none before. Because it was silicone, I could be rough when I fucked myself, aggressively filling my hole while the balls bounced off my ass. I could slam it in, then pull it out, showing my wanting and gaping asshole, then slam it back in again. It felt so good inside me; I would sometimes leave it inserted then watch a movie. Feeling how stretched out and big my asshole was once I removed it really turned me on. This led to my butt plug collection.

I had a plug for every occasion, and there were few times I would go without one in. One that I wore to work was the smallest, just a simple thing, but it definitely made work more interesting. I am a secretary, so a bit boring day to day. But no-one knows that my asshole is being slightly stretched out each day. Every time I get up then sit back down, I can feel it push against my hole, sending sparks throughout my groin.

I have plugs that are ribbed, some with vibrators built in, some that are long and skinny, and some slightly curved. I have an obsession, which explains the plug I currently have in. It.is.big. It's bead style with a suction base. I had to stick it to the floor then lower myself onto it, using my weight to push down. The first bead, the size of a golf ball, got swallowed into my asshole quite easily, but the second was much bigger. It was the size of a baseball, and after some wriggling around, I slowly stretched my asshole around it, as it disappeared deep into my ass. The third bead was too big for me, no matter how hard I tried. It was the size of a grapefruit, and no matter how hard I stretched my ass I couldn't envelope it inside of me. So I kept the other two beads inside of me, and wrote this story. Every once in a while I would start to pull them out, feeling my asshole stretch open as the bead slid out of my ass, only to push it back in, further filling my used ass. I can't help but daydream of everything else I can stick inside of me, further stretching my once tight little hole. Suggestions are welcome :)

Report Story

byrockhard231© 3 comments/ 19622 views/ 11 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartfrondop, kroane and 9 other people favorited this story! 

Recent
Comments
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Chillibeer01/08/18

I don't know how true this is but give or take a few details this is EXACTLY how I discovered anal play. I played while masturbating for a long time because my bf was huge. I desperately wanted him inmore...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous01/04/18
by 21stcv01/03/18

suggestions

how about a big fist? or a horse cock dildo?

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 3 User Comments  or
Click here to leave your own comment on this submission!

Add a
Comment

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel