How did you discover pleasure in your hole?

[CumBustion]

The father of a childhood friend molested me for years. I still remember the day he stuck his lotioned fingers into my hole while playing with my lil peen and balls. It felt painful at first, getting my cherry broken into. Then I remember feeling this odd, tingly sensation. He kept it up until I felt a jolt of lightning shooting thru my body. His fingers pressed deep into my hole as my body shook involuntarily. Waves of this painful pleasure hit me. I later figured out that he made me orgasm, even though I wasn’t old enough to physically ejaculate. 
 

A few months later, it progressed to rape/sodomy. 

[Guest]

Honestly; my uncle popped my cherry so I’d say about two weeks into him fucking me daily. 

[ronnie4u]

My Mom , a Italian woman / big tits , was a party / bar hopping female enjoyed giving me enamas when I was young - a few hits on a joint !  

[damsonffpig]

Almost by instinct....first time with a guy......I was a teen (claimed to be 18 to get in....) but was much less.... and he was around 40, hung and fit.......he offered to massage my back in the sauna..........his touch alone was a massive turn on then when the end of his raw cock touched the crack of my arse, I instinctively leaned forward and spread my cheeks .......he only got the head of his cock in my first ring before I  just blew a massive teen load right across the sauna cabin........I felt so anxious that I would be caught, but just wanted more.......I then started playing with my hole more and more...and getting as much cock as possible and all BB ...pre charged loads....

[theplayerking]

Receiving my first rim job while in college. 

[ronnie4u]

On 9/7/2020 at 6:28 PM, damsonffpig said:

Almost by instinct....first time with a guy......I was a teen (claimed to be 18 to get in....) but was much less.... and he was around 40, hung and fit.......he offered to massage my back in the sauna..........his touch alone was a massive turn on then when the end of his raw cock touched the crack of my arse, I instinctively leaned forward and spread my cheeks .......he only got the head of his cock in my first ring before I  just blew a massive teen load right across the sauna cabin........I felt so anxious that I would be caught, but just wanted more.......I then started playing with my hole more and more...and getting as much cock as possible and all BB ...pre charged loads....

Extremely HOT and Beautiful - you and others developing such Big Beautiful Cunts - wishing I was your Brother or neighbor - wanting mine be like yours -  Help me Please !  

[ronnie4u]

On 9/2/2020 at 9:14 PM, bullrv said:

Got the dreaded jelly finger treatment at the doctor's office when I was having awful stomach pains. Didn't feel particularly pleasurable at the time, though it did get me thinking that it might be interesting to play around back there. Eventually discovered on my own how good it could feel using fingers, pens, and a little souvenir baseball bat. 

Oh My !  I been thinking o a Doctor for a long time - Pleasures for my cunt hole !  Love to be in the stir ups - fingering me - tools - maybe put tina up my cunt hole - be his personal toy - stretching my cunt or a Top with the equipt. straps - dugs - stretching my cunt hole - him and his friends - hanging cocks from my lips - Help me - being used  and bused - developng a Huge Rosebud !

[YourNoLimitsBottom]

I came to it later in life, and lord do I regret waiting that long!

I watched a lot of porn, and more often than not identified with the woman in the video. I know most of the noises she made was acting, but damn, she plays it up that it feels good! I wanted to know how it felt, and without a pussy I had to try the third most used hole (third most used in straight porn that is!).

I started with a finger in the shower. I am a runner, and coupled with never having had anything inserted into my ass I am very tight. It took some soap to lube my finger enough to slide it in. I imagined the guy sliding in would feel how tight that I am and it would excite him more, and the thought of pleasing him made the sensation all the more pleasurable for me. I finger-fucked myself, enjoying the sensations and imagining how my tight ass would make him feel. To this day I get a lot of pleasure knowing I am pleasing him, and luckily we tend to feed off each other, the more I please him, the more he pleases me, etc.

It wasn't long after a few finger-fucks in the shower that I bought my first dildos. Yeah, I bought multiple types (length, girth, vibrating). I used them to fuck myself as often as I could. Living alone, there were no places off limits to do it. I enjoyed using them while talking to guys in online chat rooms.

And it wasn't long after that that I took my first real cock. I've been a cock-slut ever since. In my mouth is great, in my ass is mind-blowing.

My only regret as I said above is that I didn't start sooner!

[Phallarchist]

I wish I could say that a man forced the discovery on me, but the truth is I started reading extensively on homosexuality early on. As soon as I understood the concept of rectal intercourse, I started inserting cylindrical objects and dreaming about being fucked by an excellent older boy who had become the center of my erotic attention. I eventually found the right motion and hit my prostate consistently. Orgasm ensued.

It turns out I learned the wrong lesson. While it's nice when I get it, I shouldn't expect rectal pleasure. Being fucked doesn't always feel good physically and it doesn't need to. The point of giving myself to a man is to serve him and have him inside me. I want the man to concentrate entirely on the pleasure building in the glorious length he is repeatedly shoving into me. If I happen have an orgasm, it must be after his, or at a point when the resulting anal contractions would maximize his stimulation. His release is essential. Mine is irrelevant.

In that sense, I think a sudden, uncomfortable initiation puts a young faggot on the right path, one of service and routine self-sacrifice to the male imperative. Pleasure, if it comes, is primarily a function of being useful to the man. His satisfaction must be total before any notion of cunt pleasure can arise.

[satyricon1]

Started sticking a finger up my ass when I was 6-7 years old.   Felt extremely pleasant, though I never gave myself an orgasm.  Quit playing with it when I discovered masturbation at age 13 -- came back to hole playing in my 40s -- used cucumbers and zucchini (always great fun to check out in grocery store with sex toys on the belt); still enjoy a nice dildo or plug stretching my ass.

[funpozbottom]

Around age 7 or 8, I became interested in my hole. I found I liked touching it, gently probing, and looking at it in the mirror. Sometimes a toy soldier would need to hide in a foxhole ...

[Boacat]

Up until around age 30, I had only fucked, never got fucked at all. I did (and still do) love to suck dick.  I met a guy off some site and went to his place to suck him off.  We hit it off and it became a regular thing where at least once a week I would suck him dry. This continued for a few months and he talked me into letting him fuck me.  He was very gentle and took his time.  That's how discovered what I had been missing.

[Guest]

i discovered as a teen when my clothes were ripped off me, and my cheeks were spread by someone else besides me. it was a great feeling and hearing how nice and hot ass i had and then feeling his finger inside of me graduating to his cock and the feel of his cock inside of me. and finally men cumming inside of me and the best getting an orgasm from being fucked without ever touching my cock.

[bibearbtm]

From what I remember, I first became aware of the pleasure my asshole can give me at age 11 when I let my grandmother's little sheltie lick it.  I would also let her bigger male samoyed lick me, too, but he'd try to mount me.  I used to let him but kept my underwear on so he couldn't penetrate me.  It was hot and thrilling feeling his pointy dick poke me through my underwear. One day the curiosity got the better of me and I moved my underwear aside and felt him probing directly at my hole.  Right afterward, he shoved his big dick up my ass and I felt it grow and get thicker.  While it hurt a little, it also felt amazing.  From that time on until I left for college, I'd let the Samoyed fuck me as often as I could.  Most of the time he didn't tie but he did once.   I also fucked myself with broom handles, screw driver handles, slim lotion bottles, etc. Looking back now, I sure wish I had found an older male play buddy to also fuck me, but I had to wait until I was 23 and married.  

[Guest Descartes70817]

I found out by accident just as I reached puberty. In my youth I was sent to a military boarding school in England which only issued MOD toilet paper.

This TP is more like tracing paper than toilet paper, except it wasn’t remotely soft, but it had one thing in common, which is that when it gets wet your fingers will go straight through it, and that was exactly what happened to me one day, and I just found it immensely pleasurable and I got hard instantly.