When did you discover ??.......

[Modude]

That you enjoyed playing with your ass ? or.....having your ass played with ?.....

[Fiddlestyx]

I was probably 12 or 13, but then kinda forgot about it until my 20s when I discovered a few women who enjoyed anal sex or just their asses played with. At that point I thought "oh yeah, I remember that felt nice".

[Jozyxt]

I remember speculating about how it would feel to get fucked from a single digit age. I enjoyed self ass play from middle school. The first woman that put her finger in me just slid it a little bit in. I really enjoyed it but couldn’t tell her how much. She licked the finger one time which was really hot.

The first women to rim me sent me into heaven. Pretty soon we were 69 rimming.

I still haven’t found a woman that really loved using a vibrator on me

[cornholejoe]

when me and my late wife started doing it to each other later on she move to a strapon and started using it on me and i loved it

[nu2curious]

A long time ago when a girl I was out with was playing around and kept getting closer then she licked her finger and inserted it bumping up against my prostate sending me into the strongest orgasm I'd ever had. Oh yes, I enjoyed that very much !

[BiGuyinMA]

I think for me it was when I was about 11-12yo. Started out just fingering myself before working up to a magic marker (a larger sharpie) about 3/4" dia. Back then that felt huge and made me feel very daring (and slutty) LOL... Fast forward 45 years and my dildo collection includes one close to the diameter of a coke can.

[chongster]

Don't know exactly but I have always liked it. I know when I was young and straight once in a while a girl would touch my ass hole while I was fucking her and that would put me over the edge right away. The first time I ever was penetrated a girl friend put her vibrator in me while giving me a bj. Another girl friend liked using butt toys on me and we moved on to her pegging me with a small strap on. That was really hot at the time and we both enjoyed it very much.
I only have been fucked by another guy once and really didn't enjoy it much for some reason. With other guys I suck and fuck them, I would let a guy fuck me again if it came up but most of the guys I hook up with are bottoms.

[MidTownBob]

One day about 30 years ago I was masturbating when the family was out. For some reason I was suddenly overcome by curiosity of what a cock would feel like in my ass. My ex-wife had a dildo at the time, so I lubed it and my ass up and slid it in. I loved it!

From then on, I started to finger my ass and massage my prostate as a regular part of masturbation. Needless to say, I was hooked.

[KDaddy23]

Growing up, the one thing I hated was having to have my temperature taken rectally. Feeling that thing sliding into my butt felt so weird! But I would get to feel a man pressing his knob against my hole and, man, that felt pretty good and felt even better the first time one of my friends got his dick in me. Hurt a little, felt a little weird but the good feelings erased the weirdness and, well, okay. I still hated that damned rectal thermometer - I just didn't resist or protest anymore because if I could take a dick in my ass, the thermometer wasn't really a problem, was it?

[Modude]

Growing up, the one thing I hated was having to have my temperature taken rectally. Feeling that thing sliding into my butt felt so weird! But I would get to feel a man pressing his knob against my hole and, man, that felt pretty good and felt even better the first time one of my friends got his dick in me. Hurt a little, felt a little weird but the good feelings erased the weirdness and, well, okay. I still hated that damned rectal thermometer - I just didn't resist or protest anymore because if I could take a dick in my ass, the thermometer wasn't really a problem, was it?

No, I wouldn't think so !!....

[KDaddy23]

Well, I figured out what really bothered me about that damned thermometer: It was me not feeling good for some reason. Either the doctor would show up and shove it in my ass - and that was when they made house calls - or my mom, being a nurse, would do it and it was bad enough that I wasn't feeling good and... rectal thermometer. I was so happy when I could hold a thermometer in my mouth even if I had to hold it there myself! Having a finger in there or, better, a dick was so much better and even finding out how good it could feel if the dick wasn't in me but bumping up or pressing against my hole. It just felt so good... and even more so when the guy doing it could and would cream me.

Didn't like cleaning up the resulting mess so much...

[Modude]

One day about 30 years ago I was masturbating when the family was out. For some reason I was suddenly overcome by curiosity of what a cock would feel like in my ass. My ex-wife had a dildo at the time, so I lubed it and my ass up and slid it in. I loved it!

From then on, I started to finger my ass and massage my prostate as a regular part of masturbation. Needless to say, I was hooked.

In my case, I was probably 13-14 and I would lay in bed at night thinking about different sexual things I had heard about.
One of the things that I was the most curious about was hearing about one boy fucking another boy, it was said that one boy would stick his dick into the other boy's butt hole. There were different opinions on if it was better than fucking a girl, about the same, or not as good. One thing was for sure, there was no chance of a getting a guy pregnant, but at the time I thought it was all made up because how in the world do you stick something as big as your average cock into the average asshole ??.
So one night after my parents had went to bed, I went to the bathroom and got a good finger full of Vaseline which I wiped into some toilet paper and took back to my room. I had found an old plastic handled hairbrush that my mom had thrown away, the handle was slightly bigger around and longer than my cock so I thought it would be a good thing to try. I had washed the handle good, so I put some lube on it and my hole and started to slowly push it in....to my surprise, it slid in easily and hurt for just a couple of seconds after which, it started feeling REALLY good. I started fucking myself with it, pretending it was another boy's cock.....after a couple of minutes I started getting a strange feeling around my cock and balls, a warm feeling, kind of like I needed to pee but somehow different.
I kept fucking my ass and all at once, a hot,thick, white, creamy bunch of stuff squirted out of my cock and went all over my belly and chest, it felt sooooo good and I realized that I had cum for the first time. It's been almost 50 years ago but I remember it like it was yesterday.
Ah to be young, dumb and full of cum lol.......and I still slide a dildo up my ass every now and then, and it still feels REALLY good.....

[Tight1-4u]

my very first sexual experience was 8-10 years old.. got a hand job and head the same night.. from a male cousin same age.. then when 11-12 got sent to the farm for the summer.. was fucked every day by my 19 yo cousin and 3 of his friends.. I grew to want need to be being fucked and went looking fo it.. I was their cum dump!!! So I guess that summer.. then my junior year in high school my football coach fucked me every day till I graduated.. starting of senior year high school first female experience with coaches wife then a lot of the girls.. but still knew that I loved being fucked and still do..

[TRICK69]

In my 40s I experimented with cucumbers then graduated to dildoes. I now frequently pleasure my ass.

[CockHummer]

I was in my late 30's I think. It came about in response to me trying to be thoughtful of my ex-wife (or at least, so I thought).

I no longer recall where I was coming home from, but I was on a stretch of road where there was an X-rated bookstore. I'd never been in one in my life, but I decided, "What the fuck? I had no idea what they would sell, never having been in one before, so I just patiently looked around to see what was up. The things that most caught my eye? A dildo, a set of three progressively larger butt plugs for gradually loosening the anus, which came with an incredible penis shaped vibrator that had like 9 different powerful modes of vibration, and a quite thick porn mag on anal sex.

My ex had a beautiful ass, and she loved anal sex, but it was mostly my tongue and a few fingers. She had a problem in that she loved sex but could never allow herself to have an orgasm, as the sensations, instead of being wonderful as they are for most people, were just too powerful, and she disliked it, so I was investigating means to help her learn to relax and ease the feelings and maybe let herself cum. Since she couldn't enjoy cumming, she never masturbated, but she did appear, in spite of it all, to really enjoy having sex with me--we'd just have to take breaks along the way, and I had to be satisfied with being the only one to cum. I told myself I got those toys and the mag to help her on her journey to maybe cum and maybe masturbate. She liked anal. She'd beg me, "Fuck my ass," but she meant with my tongue and fingers, and I was hopeful she'd get to where a bigger part of me would go in there.

I had to be honest with myself, though. I knew as I was driving home that the dildo was turning me on. I wanted to play with it. Of course I would be playing with it! And I'm looking at this athletic Adonis on the magazine cover and his huge enough to be in printed porn cock, and I knew that I would be studying the magazine, maybe more than she. Okay, almost certainly more than she. After I gave them to her, and she seemed excited with the gifts, she found some sex toy lubricant somewhere, and I bought a locking, bulky brief case to keep it all in, so none of our three young sons would be snooping in our closet and find the toys.

In all honesty, I have no recollection of whether she ever used them. Perhaps I never knew. Let's just say, they did not go unused.

I was a family doctor, and of course, I had nights on call, when the phone could ring at any time, and I might need to go to the hospital. My ex tired of that fairly promptly, so whenever I was on call, she would sleep in the guest bedroom downstairs. Did I just say that my ex happily let me have our bedroom and the brief case full of sex toys to myself whenever I was on call? I did, didn't I? I promptly put a lock on our bedroom door, just to assure that no one would walk in on me while I was playing with the toys.

I went all over the place. I'm a tall, thin man, not in the least bit feminine or effeminate, but somehow I managed to fit in her nighties, bras, and panties. I would dress up like her and then put one of my shirts on a bed pillow, have a pair of jeans hanging off the bottom of that, and then I'd have the dildo hanging out through my fly on the jeans and give myself a blowjob.

Once I got used to the dildo, I practiced taking it in my mouth and throat as far as I could. Then it was time to try getting fucked in the ass. It felt so horny, I just kept pushing and pushing. It was a style that I don't think you can find anymore. It had no balls and no suction cup base, so it was all pretty much the girth of the shaft, and the next thing I know, I've pushed all 8" of it up inside of me, with the smooth, round part (the head) that might slip out more easily facing in the wrong direction (for that purpose, anyway). I feared I was going to become an emergency room story to tell, but somehow it popped right out. At least I knew I never had to worry about that again. Well, and then there was an even more convincing reason I never had to worry about that again.

I got my eye on the cock shaped vibrator. I had just found out that it felt really good to have a pretty good approximation of a cock stuffed up my ass, so I decided to answer the question, "What about a vibrating pretty good approximation of a cock stuffed up my ass?" I lubricated the thing. I set it up so the far end was jammed against a pillow and it could not slide away from me as I assured myself that it was going to fuck me whether it wanted to or not. I slid my anus down over it and turned the power on. I thought I was in heaven! Feeling like I had a big cock up my ass, combined with the strong vibration sensation, which was meant for stimulating a clit, but my prostate sure didn't know that, produced these incredible orgasms, like nothing I'd ever had before. So much for the dildo! After that, it was just a suck toy (I say "just," but I still enjoyed it).

The Anal Sex Mag turned out to be an "I wish I were her" fantasy source for me. I would read stories about these big, muscular guys with their huge, hard cocks and the girls they wanted to fuck in the ass, and how they would get them, and I would fantasize that I was one of the girls. Any of that had me coming really hard. After I'd had the toy cocks up my ass, I didn't even need to bother using one when I read those fantasies. I could recall what it had felt like, and that left me a hand free to turn the pages and a hand free to jerk my cock. I think those were some of the best gifts I ever gave my ex, that she barely touched and I had a ball with.

[Jozyxt]

Another recollection came to me. I remember being fascinated with my hole as a young boy. And of course you can;t see it. I spoke about it to my mother, who being the calm and practical person she was, suggested I look at it in a mirror then took me to her bedroom to use the full length mirror.

I dared not touch my ass where her present, but later used the bathroom mirror and di touch myself. And of course smelled my finger and eventually tasted it. I found the smell and taste of my ass after a bath enjoyable. I suppose that prepared me to get into rimming my GF with such passion when she opened that door for me.