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The couple I had my first threesomes with, she would always want to play with my hole. It had never been particularly my thing, but with her it seemed whatever position we got into, I'd get a finger at least one knuckle deep in there. Then she started using a bullet vibe on me, and said how she'd love to peg me with a strapon, which I had to think about for a while.

In the meantime I began to enjoy it, and started to include anal play in masturbation, with beads and then my first prostate vibe. OMG, once I had my first prostate orgasm there was no turning back. My bum is and always will be vegetarian (no meat), but guys, the prostate is an amazing and sensational thing and you should go play with it.

I eventually agreed for my friend to peg me, and for us to share a double ended dildo. The first time was a bit painful - we found it hilarious in fact, particularly her husband watching on - but I learned to get myself prepared for it, and it became much more comfortable. And very enjoyable.

I've been pegged by a few women now, and they all seemed to get very excited by the experience. Me too!

My last partner was particularly adept at giving a prostate massage with her finger - and sometimes two fingers. We both loved butt plugs too, and fucking while plugged is another amazing sensation. I have a number of plugs and prostate vibes now among my toy collection, and I wouldn't be without them.

There was a time maybe up til about 25 years ago I would never have thought I'd take anything up my toosh. Now, I strongly recommend it to any guy.

HT

Was exploring as a teen & found it was extremely pleasurable.
I've a lot of different things in my ass, but the best by far was a good elbow deep fisting from my wife

I got into anal play while visiting massage parlors too. Worked next to one. Met some of the girls working on their cars and got invited. The second time I got massaged, the masseuse started by giving me a table shower, taking time to clean me down there. Later on the table, I noticed that she had put a finger from a vinyl glove on her left middle finger. While jacking me off, she slid that finger, covered in oil, into my ass and massaged my prostate. I came immediately. Loved that feeling. Second wife and I enjoyed several anal toys. ( keeping them clean is imperative) I have never been able to have a cock in my ass. I have tried ( pain and the feeling of having to poo) I have learned though, that regular play, and enjoying larger and larger toys as you get stretched out some is the way to enjoy it. Just get some good toys, and plenty of lube. Experiment and have fun!

I’ve been playing with my butthole for as long as I can remember. Like before I knew anything about sex. Once my dick started getting hard I had regular orgasms around 9 or 10. With that I quickly figured out that my ass liked to be filled and stretched. Once I got old enough to buy toys I used those, eventually got a real dick in it. I’ve loved anal play my entire life, never get enough of giving or getting. It’s my only natural talent, it never hurt, I can take really big toys, absolutely crave feeling the cum squirting in. Sadly I don’t get any real dick, been many years. It’s a bitterly frustrating way to live. But as our recent pics show my wife is still an expert at working my hole out. I’d love to find several tops guys to DP me but probably never happen.

When I first fingered myself when I was like 5

Self exploration before puberty

As a xxxxxxxxxxxx, Felt good, so i would try slim objects like candles. Been liking it ever since. Was first penetrated in my 40's ... sometimes good, sometimes a little painful - just too big a diameter to handle. since then, i've used vibrators and butt plugs.

When i was younger i was not really into anal, but one day hubby got me a small buttplug as a gift. For some time i forgot about it, until my hubby asked if i had tryed it out yet. I was pretty nervous, but after i got it in, it felt really good. After this i was hooked, and now i got a couple of large buttplugs that we use often before analsex.

For about 60 years l have been fascinated by sexual organs male and female,and in my twenties l had my first real gay sex.
it took another 40 years before l tried anal as a top l had been buggered in my twenties a few time,but always as a bottom.
And then a good friend of mine asked me to fuck him and so l became versatile.
Now in my late 70s i`m bottom again,full circle.

I went to a masseuse who gave really good full body nude massages. After a while they got more intimate and she would massage my ass and ran her fingers over my anus while massaging my balls with the oil.She said it helps to relieve tension. soon she advanced to inserting her finger into my anus and massaging my p gland. Soon my cock was fully erect and I was ejaculating thick ropes of cum onto my stomach. A really great experience for sure!

I started playing with my ass when I like 6 or so.

When i was 19yo my 26 yo GF enjoyed taking it in the back door and i enjoyed giving it to hear. We went our seperate ways and the gal i married at 25yo didnt enjoy getting her booty banged. So for the next 17 yrs i only got booty a handful of times. After we divorced i statred meeting lots of open minded, adventurous , kinky , bi ladies. Several of them loved it in the ass and demanded it. While playing in 3somes with other ladies, younger ones especially . My playmates would encourage these young ladies to give up the booty to me, many times letting me take their anal cherri. They showed and helped me how to get those tight asses to relax. Soon i was a regular pro and went on a quest to convert every ladie i entertained to an anal whore.

I wish i had a dollar for everytime one would say " i will never like it in my ass" within 1 or 2 times with me they were asking " will you fuck me in the ass" ? No ,I would tell them. PLEASE? Please what ? I would say. PLEASE FUCK MY ASS ! I have never met a lady i didnt convert. I have never been with a virgin , but i have taken dozens of anal cherries .

I started meeting cucked couples and found that dynamic very interesting and so much fun. The wives were dom to hubby but submissive to me. Many times i would take the wives anal cherrie as hubby sat and watch me violate his wifes virgin asshole. The wives would be saying OMG! Look at that honey he is fucking my virgin asshole!! Doesn't that look so HOT!! Look at that big hard cock stretching my tight asshole ! God it feels so good honey.

I let a couple of beautiful playmates try to give me a finger , but because i am to much of an alpha male..... being sub just does not work for me. Just the opposite and it turns me off.

Anal lover and converter forever!!