What/Who got you into Anal Fun

My partner introduced me. It was strange at first, but it feels really good.

 

Hope it was an enjoyable experience and that you will want to do it again.

 

I would definitely consider it. lol

 

I had my awakening in my 50s. Started buying cock rings and a few toys. I introduced them to my wife slowly. It wasn't until I was 56 or 57 I bought a prostate massager. It was great but as most of them are, they are meant to be used and not worn. I branched out and bought a couple small plugs. Then some larger ones, and eventually a rubber dildo with suction cup. I am working slowly to introduce them to my wife because I dont believe she knows my true love of anal. To conclude my favourite in my collection is a silicone cock and ball ring strap with a stainless steel butt plug I wear out constantly, to work or other events.

 

Did you dirty talk

 

I'm a straight dude never fucked a girl in her ass. But I think I have to try it now.

 

It’s feels really good at first, as it is really tight.
But as you go it will loosen up and the sensation will get less.
It is very erotic for sure.

 

I didn't even answer my own question. A wonderful woman( 20 yrs older) I met when I was a Bartender introduced me to anal pleasure. When she went from sucking my cock , she continued on to sucking my balls, then eating and fingering my asshole. There was no looking back. When I wanted to play with my wifes ass, she asked me how I would like something poking in my ass. She was surprised when I said YES! , then she proceeded to slide her hard white plastic vibrator up my ass. Many vibrators, buttplugs and dildos have happily visited since.

 

Times have changed. Anal used to be taboo and now it seems like it isn't a big deal.

When I was younger, it was difficult to find a girl wanting to try anal. My first experience was with a gf that I inserted my finger into her ass while we had sex. She really didn't enjoy it. I really wanted to put my cock in her ass, but she said, no way. She thought my cock was too big. She said how you like it if I put my finger in you? At the time I was like no thanks. Then she did it while giving me a bj and I thought it was amazing. I've loved it ever since.

My first time having anal intercourse was with a girl I met at work. Before I even had vaginal sex with her, we tried anal. I couldn't believe that she was open to it. She had never done it before and my last gf thought I was too big for her. Anyway, this girl was remarkably relaxed and I went all the way in her. She took it like a champ and it was such a turn-on. Then we had vaginal intercourse and there was no going back to anal for her.

She would play with my ass sometimes using her finger. I asked her if she would consider pegging me and said sure. We never tried it though.

I ended up marrying a different girl. One night while we were drunk in LA on vacation, I asked my ex wife what she thought of pegging and she said maybe. We went to the Hustler store down the road, but we didn't buy a strapon for some reason I can't remember. It was until several years later that I tried pegging with a pro domme. It was amazing.

Nowadays it seems like everyone is eating ass or having anal sex like it's just regular intercourse. Progress I guess.

 

Always been interested since seeing it in porn and got a chance to try it on my girlfriend in high school, albeit both times with a condom. In college I got to bareback this Indian girl’s ass I knew from high school for the first time and I fell in love with how good it felt. There were a couple other women around that time in college that let me in their ass but nothing too memorable.

Soon after while still in college I ended up meeting this particular milf/gilf through my cousin that changed my life in terms of how I view anal sex and just how good it could be. She was a much older puerto rican woman whom he met through the Craigslist personals and had already been fucking around with. She was married with a bunch of kids, some actually older than us at the time, and was even a grandmother but was on the hunt for some young cock.

It’s a long story but my cousin got her come over and hang out one night and after getting drunk with us we tag-teamed her something serious and had a wild night. I literally just me her but the night ended with me blowing a huge load up her ass that turned out to be one of the most gratifying orgasms I can remember. She was a thick bbw with a huge ass and from the neck down could’ve been one of those instagram milfs who had an only fans. Her cheeks were incredibly soft and jiggly and her asshole was super loose but still snug so feeling that combination on my dick and in that circumstance caused me to explode up her ass. That situation is what really started my anal fetish and I’ve been chasing that “high” ever since.

I’ve gotten the pleasure to fuck quite a few chicks in the ass but the most recent and satisfying result of my fetish was a sweet situation I was in a few years ago. It’s an even longer story but a guy I got to know very well started sharing his wife with me on a regular basis and it turns out she was an anal freak. At the peak of our “arrangement” we were fucking at least 3 times a week and almost every time it included some anal. She wasn’t necessarily my type because I’ve always preferred heavier women but she had no problem keeping me aroused based on her freakiness and feel although she was slim. That whole situation just drove home the fact I really like fucking women in the ass lol

 

There have been several stages I guess. Each progressing a little bit.

In my late teens, my introduction to it was a finger in my ass during a bj. Felt great, but can't say I really thought about anal play.

Then in my 20s, I dated a kinky girl that was into playing with my ass. I guess that led me bring it up with the next girl I dated. She was the first one I ever fucked in the ass. She in turn, put her vibrator in mine. I guess that escalated things.

In my 30s, it was a dominatrix that first pegged me. Again, a step up from before.