The first time you were plugged.

My first plugging was about 25 years ago. It was a medium sized Butinsky plug. It was a wonderful experience and I still use plugs regularly. I like to wear them out and sometimes at work. Just love the feeling of being plugged.

My first plugging experience was with an plug that I personally made on a lathe some (many) decades ago. We had this "tech class - workshop" in last year of elementary school were we learned all kind of tech things - some simple electrics (battery, lamp, switch, such things), mechanics (lever, sprocket, etc) and also woodworking. I remember loving it and lathe was a machine I really got a grip on. At that time I also found some porn and started exploring sexuality and of course, lathe was a perfect tool to make something dildo like (usually it came out like it even if you didn't want to - well on a lathe everything comes out at least cylindrical and then add some grooves and make a part of it thinner and voila - there's your dildo). I remember lacquering it and one day I brought it home, I had a few hours till parents would be home and of course got the porn and the "dick" out . Seeing what did they do with such things in the porn mag, I had to try the same. I remember that it was really hard getting it in my butt (nobody told me some preparation or lube would be nice... oh on the pics everything looks so smooth, easy and enjoyable) and then some of it was left sticking out of me (it was quite long, fortunately, so it didn't get "swallowed" up), I could see myself in a mirror and it seemed to me somewhat awkward with that pole sticking out. Not feeling anything special or even remotely like it seemed it would feel like in the mag, I removed it and of course it had some shit on it - doh... at first I thought how I'd get rid of it, cleaning shit wasn't something I was looking forward to and as it did not anything special to me, I thought maybe throwing it out of the window. On the second thought, I realized that it surely would be found and could be linked back to me, so I reluctantly washed it and put it in the drawer underneath some other stuff. Didn't use it again and after some time I eventually got rid of it.

I got my first "real" plug - a smallish jelly plug - quite a few years later in a shop out of my home town, and by then I knew the secrets of the trade so it was oh so much fun! When I learned about the dangers of materials such as jelly (although it held up so well I thought it was silicone, but when I did the flame test on it, it did burn) and it got replaced by silicone toys. I remember going out once with it and while it stayed in OK at first, it started slipping out after some time (to my absolute horror) and I remember turning my back against the wall on the street to try to "casually" push it back up in place with my hand. Thinking of that makes me blush even now, after all these years. But that little thingie started my obsession with plugs, having so much fun with them!

Happy plugging!

My first plugging experience was similar to yours, @afternine. When I was a horny teenager, I made a dildo-shaped object from a squared piece of wood using a file and sandpaper. The feeling was not particularly great, even though I used plenty of Vaseline as lubricant. And of course it did not take very long until the wooden object started to smell.

I bought my first real butt plug shortly I left my parents' house. My firsts attempts were extremely frustrating since I could not get the plug in. However, with increasing exercise and plenty of lube, I finally managed to insert the plug. I still remember how amazing it felt when the widest part slipped in and my sphincter closed behind it. I was hooked from that moment on!

I wish I could remember my first time... Must have been something special considering how much pleasure I get from it nowadays.

My first was just putting a condom on the vibrator my wife used. I was alone and wanted to know what a vibrator up the butt felt like.

After that I went out and bought a smallish one. Of course I bought bigger and better after that. Love the vibrating in the butt feeling.

My first time was with an inflatable vibrating plug I ordered with my first pay packet. I was so horny I didn’t even think about warming up and just shoved it in after lubing up. Wow, the pain! I didn’t know what to do with myself! I was so sore for a couple of days, I obviously strained the sphincter muscle. Quite funny looking back on it now.

Since then I’m regularly plugged. I’ve actually had the same butt plug as that first one but have had four new ones as I’ve used it so much since then and is my favourite plug.

The first time I actually used a plug was years after I had started experimenting putting things in my ass. I was travelling and stopped at a Lions den along the interstate. Funny to think about now. I was embarrassed and actually told the sales woman I was looking for a beginners plug for my girlfriend. I finally picked out the doc Johnson medium. I thought it was huge at the time. The next 3 hours was a long drive and I couldn't stop looking at it and my ass was starving to see what an actual toy felt like instead of household items and veggies. When I got home I did a quick clean out, didn't even unload the truck, and then started working it in and out until it finally popped in. Goodness what a feeling. I was hooked. To this day, maybe from nastalgia, I still consider that one of my favorite plugs amongst my many toys. Just talking about it makes me want to go home, get it out and put it in for a few days.

I bought myself a Doc Johnson medium plug and some KY Jelly, lube it up and managed to get in on the the first attempt, I had used some 'improvised' anal sex toys and a 6 inch dildo so I was reasonably used to being penetrated... I was amazing, i loved the stretch of it going in and the fullness when it sat in me. Did not take long for me to have a massive cum and i have been using plugs ever since.

You might say I love them 😄

I got my first butt plug on a business trip to San Francisco about 25 years ago. I had a lot of anal toy experience with vegetables and other homemade stuff but never an actual plug. Went to a porn shop and saw my first plug and knew right then I had found my new best friend. Rushed back to my hotel room got that bad boy in me and has been a downhill journey ever since.

I remember had to flush out with a plastic water bottle laying in the tub of warm water. Then just relaxing with that first plug in me. Kept taking it out and admiring its wonderful shape. Even wore it around most of the next day. Have been totally hooked ever since.

Plugged right now and slept with it in me last night. Actually last three nights ha. Have come a long way from that first plug.

I do t remember the first time so much but the first time I had a decent size plug in that feeling of being stretched to the point of almost hurting. Feeling full ones fully inserted was amazing . The orgasm that followed was something else the anal contractions where so strong and I've never felt them before .

I just got my first one a couple weeks ago. I like the feel but it was too small It is a Doc Johnson Mood Naughty in small size. Last week I got a bigger one Not a Doc Johnson but is looks the same as the smaller one only in a large size. I have worn them both out in public, which is a real thrill but both of them irritate my perineum after a while. I read some other posts that mentioned this and said it takes a while for the skin down there to toughen up. I am really liking the plugged lifestyle though. Wish I had tried them sooner.

My wife insists I have a tampon in my anus while she is on her period. After a few months she got me 3 different sized plugs. So I now wear one of those instead as I can keep them in all day. Wow what a rush.

I was 15 or so and managed to get a doc Johnson triple ripple! I was hooked, I used to wear it to a neighbors hot tub by myself and then sleep with it all night.

Wasnt until I was about 29. A certain girlfriend had two buttplugs, the thin blue one and the big fat black one. The first one used on me was the blue one. She was quite dom and told me to get head down ass up on the bed, then to reach back and spread my cheeks wide open for her. She took her time lubing my anus, always loved playing with my ass. Then she slowly inserted the plug, taking her sweet time. She made me keep it in quite a while and made me show it to her as I walked around the house. She took her time removing it too, then took care of my puffy red bottom hole afterwards. She was a very naughty, nasty girl!

I was 22 yo at a riends house

The first time I am plugged is today, about an hour ago. I purchased a couple of goodies from amazon to add to my collection.

https://www.amazon.com/dp/B0D8KBQV9P?ref=ppx_yo2ov_dt_b_fed_asin_title

This is a portable enema bag, not a big deal, but silicon, should last a while, kind of small though.

https://www.amazon.com/dp/B0CZRLPLQC?ref=ppx_yo2ov_dt_b_fed_asin_title

This one is a nozzle I haven't seen before. I had to lubricate the heck in order to get it in, I guess that's why they call me a tight ass.

The hose is kind of small, won't fit my normal enema hose so I'm working in the shop making an adaptor from delrin.

I did pull it out once, was not difficult, also reinserted it, not difficult, I must be stretched somewhat.

It's comfortable, hardly know it's there, ha ha

I became curious about anal stimulation some time during my first couple years of college. I commuted to campus, so storage of my toys wasn't much of a concern beyond my parents getting more curious than I expected them to be. I actually started with a horrible plastic p-spot wand that did hardly anything for me. Eventually, I got a basic anal trainer kit, but only ever made my way to the second plug. Eventually I added some dildos, beads, and a couple different types of plugs, one of which was vibrating, but I got rid of most of them when I moved. Now I only have a glass plug, the Pipedream Icicles No. 45. Big enough to feel full and to wear out in public when I want to, but not big enough to cause long-term discomfort when wearing it for prolonged sessions (which, tbh, only last a few hours at most).

A number of years ago I found an”adult book store “ that also had a decent selection of toys. Along with the various magazines such as Enema Erotica, Enema Digest, Waterworks, and other magazines, I bought a medium sized butt plug and an anal vibrator. They were the first objects other than the enema nozzle that were actually intended to go in your ass. Prior to that it was just various things like fingers, pens, hairbrush handles and the like. After using them on myself during masturbation I decided to try to get my wife to use them on me, and for me to use them on her too. She was quite hesitant at first, her not being all that interested in anal play or enemas. She had to be really warmed up before using them on her, but when I had the anal vibrator in her ass while doing oral on her the results were very good.