How did you discover pleasure in your hole?

[backdoorjimmy]

I've been reading the replies in a different thread about being taught to jack off and wonder how everyone discovered their holes. It's a place we're taught to stay away from when we're little because it's "dirty" back there.

I discovered my hole in a weird, spontaneous moment where I felt the urge to stick my finger up my butt when I was sitting in the bathtub. It felt so good, and I started doing it all the time. I'd go hide somewhere and finger my ass 5-10 times a day because I needed to do it. My room, the bathroom, the backyard, behind the sectional in the living room and even in the dark in the kitchen while everyone else was watching tv.

What was your "ooh, that feels good!" moment like with your hole?

 

[bullrv]

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. 

[NastyRigPig]

About 6 months after my stepdad started fucking me I discovered I really liked it. 

[bareback-flipflop]

It happened quite late, I was around 18. 
I was just curious. I knew that something could happen down there. And as my father’s nunchaku seemed suitable, I tried it  (then I had no idea about lubes, so I used body lotion) and I liked it. From then, that tool became my top lover for years. LoL 

[bredbiyou]

Similar to what I wrote a few weeks ago in the thread about how we learned to masturbate, my discovery was the result of curiosity followed-up by experimentation.

At the time, I had had a single experience with vaginal sex. So I knew firsthand how good it could feel to have one's cock inside a warm fleshy hole. But back then, it was harder for me to imagine getting actual pleasure from my ass. Growing up, I experienced frequent bouts of constipation. Due to the constipation itself and the occasional suppositories that I was given as a result, I only knew that if I was aware of any feelings in my ass they were generally ones of discomfort.

I knew I was turned on by the thought of sex with guys, and I understood that anal sex was one of the main ways that guys had sex with each other. Because my own ass was a source of pain and discomfort, I just assumed that it was the same for most people. And because of that, I naively also assumed that the top position (even though I wouldn't become aware of that term for another year or so) would be the default position for most gay and bi men. I figured that any time two guys hooked up there'd be intense bargaining over who gets to fuck who. I imagined that most encounters probably resulted in flip fucks, with the 'losing' partner having to endure his fucking first, while hoping that the top would finish as quickly as possible, praying that he wouldn't renege on his promise to switch positions after he'd cum.

Then I was chatting with someone on a LGBT peer support line, and I mentioned that one of the things that made me nervous about trying to find a boyfriend without my parents finding out, was what if I go through all that trouble and risk of being 'outed', and I end up meeting someone only to find out that he's unwilling to accept an equal split when when it comes to fucking vs being fucked. She responded with something that I'd never even considered, informing me that there are lots of guys who really enjoy being the receptive partner, including some who enjoy that role exclusively. That seemed unfathomable to me, because I knew that fucking felt great. Why would someone consistently forego that in order to take it up the ass - something which I assumed felt uncomfortable at best? I decided I needed to experiment and find out for myself.

Absent access to actual cock, I turned to household items. I noticed that one of the (appropriately named) joysticks for our family computer didn't have a molded handle grip, but was rather round, smooth, and not intimidatingly thick. I actually bought condoms for the experiment when my mom sent me to the nearby mall to pick up a few groceries. I wanted to keep the joystick relatively clean by not inserting it into my ass uncovered. I didn't buy any lube. The condoms were pre-lubed with a spermicidal jelly. But I also remembered that we did have a bottle of baby oil in the bathroom. I knew from sex ed that oil was bad for latex, but I figured it would be okay since I only wanted to get a sense of what it felt like and would probably be done before the latex had a chance to break down. I remember coating my hole with it, then laying on my back with my legs elevated, and slowly pressing the handle into my ass. The handle was tapered, so once the tip pushed through, the rest of the shaft followed quite easily. To my surprise, there was no real discomfort. I didn't immediately feel that it was pleasurable. But it certainly wasn't a bad feeling. It just felt kind of odd having this hard foreign object lodged inside me. I started to slide it in and out, and that too became easier as the oil and the jelly began to get spread around inside my rectum.

And then as I laid there and continued to fuck myself, my life's path changed on the spot, as I began to relax and found myself imagining, "what if this was someone's actual cock? What if at that moment I could gaze up at somebody whose cock was thrusting inside me and I could see the pleasure on his face? How exciting would it be to watch a man shudder in climax while still inside me, knowing that it was my body that gave him that orgasm?" And I had other transgressive thoughts like, "how horrified would my parents be if their son disregarded his conservative homophobic evangelical upbringing to not only have sex outside of marriage, but gay sex? And not just any gay sex, but as the receptive partner who's submissively offering up his hole to be used, similar to how a woman gets fucked?" And when I snapped out of those thoughts, I glanced down at my own cock. It was hard as it had ever been, and was leaking precum. It was in that moment that I started to get a glimpse of how much potential pleasure I could get through my ass. Any notion that I'd previously held that guys must only enjoy topping, immediately vanished. The real question was whether I'd ever want to do anything other than bottom. And that was also the beginning of my realization that shame could be harnessed for my own sexual gratification too.

[ConversionPerv]

30 minutes ago, bredbiyou said:

The real question was whether I'd ever want to do anything other than bottom. And that was also the beginning of my realization that shame could be harnessed for my own sexual gratification too.

Amen, brother.

[BlindRawFucker1]

I don't really remember how I discovered that playing with my hole could feel good.  I know that it most likely happened somewhere between the ages of 8-10.

 

I started with my fingers.  As I got older, I used things like carrots or glass bottles.  I also used my whitecane several times, which didn't feel all that great.

 

But no matter how much I played down there, the thought of a guy putting his dick in there scared me and grossed me out.

 

It wasn't until my late 20s that I discovered the overwhelming pleasure of bottoming.  Amazingly, there was absolutely no pain.  I was in heaven.

 

Even now, initial penetration hardly results in any discomfort.

[Guest VBchaser]

It wasn’t until about 7 years ago that I inserted something inside my hole. I was so desperate to try, I took a rounded  toothbrush travel holder and lubed it with baby oil and took my own virginity. It wasn’t the best feeling but I couldn’t go deep because it wasn’t very long. The only thing I found with a reasonably rounded tip was the handle to the plunger. I used a generous amount of cellophane wrap to cover the handle; applied a generous portion of baby oil and slowly slid 5-6 inches of the handle. I would rather have a bare lubed dick in me spurting. 

[Anonversecuck]

There’s no physical pleasure in my hole for me. The few times I’ve bottomed, it’s been for the same man and it wasn’t because it felt good in my hole. It’s more of a mind fuck than anything physical. 
 

Being so vulnerable and giving your ass to another man is just such a mental fuck for me. Like I’m giving this guy the most precious part of me, and it doesn’t feel good, but that doesn’t matter because in some fucked up way I derive pleasure from being taken like a bitch. I’m sure there are a few that understand what I’m saying here lol. 

[shinelover]

I think I was in my early teens when I just started getting that urge. Somehow I just knew that I needed something up my butt. My bed at the time had a loose spindle that was funnily shaped like a slim butt plug, so I worked it loose and started trying to get it in my hole.

Not the most comfortable thing I've ever had in there, but it certainly got things started.

[C10H15N]

Started fingering myself around six or seven.  Worked up to toothbrush handles, hairbrush handles - whatever looked fun in the bathroom during my bath.  Had my first orgasm at twelve and had something up my ass by my third jackoff session.  

[NastyRigPig]

It was about 6 months after my stepfather started fucking me.

[ronnie4u]

Oh !  I was a skinny , white , boy growing up - had a group of guys having j.o. sessions -tasting our cum - accidently caught 2 guys - white / black having sex - learned about sucking black dick and became friends - transforming into a fem boy - sucking dicks - learning toys - name of my hole - cunt .  Then sent to my Uncle place - my cousin / 22 yrs old - sharing bed and room with my cousin . Smoking Weed , Drinking , Eating - J.O. sessions - ( Untold about night pills - thought aspirins ) . Being used and having Dick every night for 2 weeks ! Then my Dad - surprising but could no refuse ! Then mom - dad divorced - mom on Black Boys - Wonderful times of Dicks !  

[Guest shyslut]

It took me a long time honestly. When I was in middle school I knew that it was "supposed" to feel good but it just never felt good to me. I also hated the idea of topping so I just messed around with my hole hoping it would feel good someday. I kinda gave up after a while, but I would still let guys fuck me. Then I got an average size dildo like a year ago, and it suddenly started feeling amazing!! I don't know what changed but now I can't get enough :))

[NWUSHorny]

I didn't discover it on my own.  I still don't like fingers, my own or otherwise, or toys. I did love it the 1st time I got a dick up there and still do.