Your first time with a sex toy into the anus

@Omniphile your reference to a zip disk made me laugh! I thought 'this guy must be my age' and you are. It's hard to imagine today that those were state-of-the-art once, holding unimaginable amounts of data.

I came very late to anal play (having fantasised about it for many years). First experience was not great. Awful, in fact. It was during a Prison / Strip Search role play. The 'guard' knew my hole was virgin. I was tense / nervous as hell. He had very big fingers and (probably) did not lube me up enough. Realistic alright...but a horribly painful experience .

Fast forward 9 months, I found a more sympathetic, patient guy. Over 2 -3 sessions he loosened my hole and I learned how to begin to relax. I got myself a slim female vibrator and found I could take it...and I liked it... a lot. I progressed to bigger dildos and subsequently met a few guys who, to my astonishment, wanted to fuck me!! Nowadays...I just love it......

For me I would say in my late teens

The first time ca. when I was 15 years old. Thicker pen, wood handle, candle...recently metal spray bottle. I was not brave enough to buy. But this barrier, has just crossed. Thanks to Zity, Buttwoman and to the others.

The first time I ever did this was in a real life play examination with a play doctor I met here,

I was 42 so I was very late in learning these things as I had had a daft religious life up to then,

I was nervous, unsure and embarrassed that I was enjoying it so much,

The person I was with i trusted to the hilt and still do, I have too, he took pictures,lol.

They are the only pictures that have ever been taken of me in my life in that way,any sexual or game way.

I hope he has destroyed them lol.

Peace,

Caz

I remember first becoming interested in my anus when I was maybe about 9 or 10. I was small enough to stand up on the bathroom counter-top and bend over to get a good look at my hole for the first time. Around the same time, I started looking for objects outside to insert there, using smooth sticks and even playing with discarded cigarette butts. In retrospect, that was kind of nasty, but I think I was excited by the fact that even touching cigarettes was forbidden as a kid - so putting the ends in my ass was especially stimulating. Over time, I experimented with things like a toothbrush handle and other improvised "toys."

When I was in college, there was an adult bookstore about half an hour away. I spent hours browsing the place, which was filled with porn videos (VHS in those days) and a cornucopia of sex toys. It was there I bought my first real anal sex toy - a dildo that contained a vibrator. It took some practice, but eventually with plenty of lube, I was able to sit on it down to the root and masturbate to the delicious feeling of my hole being stretched open. I actually bought several similar vibrators over a period of time, as I'd feel guilty about it and throw them away later on.

I had a close call once when I was living off campus with a roommate. I thought he was gone to work, and decided to push the envelope a bit by stripping down in the living room for a good masturbation session with my vibrator/ dildo and a porno on the VCR. I was enjoying myself, riding my newest toy, when I heard a stirring upstairs. It turns out he was home and had been sleeping, and I heard him walk across the floor to the bathroom. I don't think I've ever moved so fast in my life to turn off the movie, grab my stuff and run with my clothes to the downstairs bathroom. I suspect he must have heard the video, but don't know if he figured out what it was. In any event, he never mentioned anything about it to me.

My first sex toys were definitely "found" objects. Somewhere around 10 yrs old was a dining room candlestick-. Cucumber from the garden and remember it was a warm summer day and I rubbed off the burrs so as not to prick myself and inserted just the tip with a bit of spit.

My girl Robin was first to actually put a true vibrator up my butt while we were romping. It was a skinny 10" and she did her level best to bury it in my ass. She was fucking me in the ass and sucking me off and I had one of my best all time at that time orgasms. I was hooked.

At age three, after my first enema experience. One of my toys had a short, small diameter metal spindle that I inserted. It wasn't exactly pleasurable and caused slight bleeding, but the die was cast for more to follow in years to come.

At age 20 in college after a party my GF at the time went back to the dorms we tried it out on each other first vaginally then I went on all fours I felt her hand underneath my belly it was her way of telling me to arch more then she slowly but deeply inserted it in my anus it hurt we only went for about 5 minutes then stopped

My first time with an actual sex toy in my ass was when I was 15 , but since I was 12 I always used a different range of household items.

I remember being in my teen years, and later on, my wife wanted to try it as well with me. Our latest addition was a cock cage, and it's been the best one so far. we have tried lots of sex toys over the course of the years as we feel more intimacy in our relationship with them. Butt plugs were my wife's favorite back in the day, but she has gotten more engaged into domination games, and I'm not against a cock cage as long as it's not too uncomfortable. Unfortunately, most of them are too restrictive, but the one I got is a vibrating cock cage toy, making the experience even better.

Mine was when I was 14 and I had the plastic end of a brand new plunger that had a plastic beaded like tapered handle i sat.down on it mmmmm

It was about 15 years ago. I was never really into the anal thing before, but I had heard about prostate massages and that they can be good for your prostate health. I read information on it and tried it using the tip of a music drumstick. It felt wonderful! After a bit more practice, I bought an Aneros prostate massager and have been using it ever since. It's made for the purpose and contoured to fit. I've heard you can have a great orgasm with this but I never can make it “to the finish line”. I always wind up finishing business via the front end, if you catch my drift!

In my teens / 20's I used mostly cucumbers and anything i could grab quickly. Bought my first sex toy in my later 20's and have never looked back!

I've been anally curious from a young age. My first anal ‘toy’ was an unsharpened pencil with a smooth rounded head on one end. I was in the shower and used hair conditioner as lube. I was around 8 or 9 years old at the time. Another one I remember using around the same time was an eyedropper (again, with a rounded head) I found in the medical cabinet. Both were a success and made me into who I am today 😄 I got my first actual sex toy around when I was 16yo - a small slender butt plug.

I think back to the first butt plug I had and how long it took me to get it inside. Now, so very many years later I don't think I'd even notice it if it slipped in.

My first anal toy was in the corn field near my house at the age of 13 or so. I'd have my pick of whatever size “dildo” I wanted to use.

Don’t remember what the first thing was that I played with but have been doing it since six or seven! Anything that looked interesting or safe and reasonable and I would try it! Lots of variety and pleasant memories!

The closest I have came is an enema. I have never had an actual toy in my anus.

I forget, they all kinda run together. It can't be that memorable if I forgot.

When I was married I think I was like 23. I got super drunk and she completely slide her vibrator in me. I sobered up pretty quick after that.

For me, I remember the handle of the tools by the fireplace. I was the only one up once morning. Pulled my PJ bottoms down, I tilted the tool out of the tool rack and backed my naked up on it. It was not a large handle, it it was ribbed. It felt really good going up my butt. Rocked back and forth on it, it was only about 4 inched deep, but it felt really good up my butt. I was hooked from then on. Turned me into a butt man from then on.

I was 19 and the girl I was dating asked if she could put her toy in my ass. I then told her if it makes her happy. It was a 5 inch vibrater. She had me on all 4s bent over. She left it in me and had me eat her pussy. She had never been so wet there before.

My first time was with a hairbrush and Vaseline at age 9 boy was it painful but pure Bliss

Well after the whole enema bulb thing I tried some vaseline and the handle of the plunger…slid right in and I got this huge erection. 🥰

Might have jacked off more than once with it in my butt…

If we're talking actual sex toys it must have been when I was in my early 20's and it was a dildo. I think I was 25 when I purchased my first butt plug and that turned into a life long love affair! From my early teens until I got my first dildo it was self made toys and various household items that found their way into my ass.😉

I guess I'd have to been 42 I mean I had Cox in my ass before but not sex toys till about 10 years ago and it was just a standard dildo

On my own at 10, it was a cigar tube with Vaseline, which was amazing! That is until my 17 yo cousin that was staying with us caught me playing with it. He and I had jerked off before so he offered to help. Tube was soon replaced by 7 inch and thick penis Once a week at night after my Sunday evening enema. That went on for a year until he graduated.

I was in my 20s. I was finally out on my own and had bought a dildo to try because I was curious about anal play at the time as I had never tried it.

I was in my mid-late 60’s and had a strong desire to have something invade my ass. I secretly bought a plug and dildo online so my wife wouldn’t know about it. She is very vanilla. The plug went in very easily and felt so good! The dildo was another story. It was only 1.75 inches in diameter, but really hurt going in despite lubing up and taking it slow! In time however, my hole “accepted” it and now craves to be occupied! Now, I have something ”up there” several days a week and really love the feeling! Don’t be afraid to try it! You’ll be hooked….