What/Who got you into Anal Fun

Did you discover it felt good on your own or did you have a partner who turned you onto it?
I was blessed to have had an older woman bring me along for a while. Early in the marraige, anything anal was off base. Once you understand, you pass it along to your partner. My problem is that we are older and my wife has passed it back. I really enjoy anal/prostate stimulation by myself , with my wifes old toys. The only problem is that you always want more. I never thought that in my senior years, I would become an anal/cum slut. Its fun and it feels great, no why not? I just cut my lawn with one of our buttplugs in my ass. The bouncing on the tractor seat had my cock drouling precum .

 

It was many years ago. My Wife at the time and I had a great sex life (that wasn't why we split. that's another story) But I asked her one day if I could do her Anally. She told me she would let me, but only if I knew what it felt like first.
So she got a strap-on with a very lifelike dildo and I let her take me from behind. What she didn't plan for was that I liked it, really liked it.So she now allowed me to do her, and we'd trade off me doing her and her doing me.

 

Experimenting when I was in junior high. Just started with a finger and discovered it felt good. Now at 57yo I wear butt plugs regularly since I love the feeling of being stuffed.

 

When I was a young boy (age about 5 or 6) I found it very pleasurable to touch my anal skin. A little steel chain pulled slowly along my anal cleft felt so good. After few years my interest started to rise. What was that mystic hole? Would it feel even better inside? So, little by little, my anal toys have been growing bigger and bigger by the years. First it was a small pen, and now over 45 years later there has been many kinds of dildos and toys. I've had strap-on fuck and anal fisting too. And my anal journey is still going strong.

 

My present wife turned me on to the pleasures of anal sex and am glad she did. It wasn't something I was interested in until she began work my ass while sucking my cock. She turned me into an anal slut and I'm so glad she did.

 

A college girlfriend would always finger me, and a later girlfriend (who knew i liked to be fingered) had her way with me with a strap on. I was hooked; she pegged me a lot but we broke up before she could introduce a real penis to me.

 

When my wife saw how much I was enjoying Anal Play, she got the itch for something in her cute pucker. I just bought new buttplugs and gave her the smaller two and kept the larger one for me. It was like a wake up call for her. I jerked off as we bumped and gyrated our butts together.

 

I never thought about it much for myself until a few years ago. I had always wanted to try anal in the traditional sense of fucking a girl in the ass, but still to this day have never had the opportunity. My wife had a bad experience many years ago with a previous boyfriend and has no interest in trying it again, to my dismay.
But a couple of years ago my wife and I both started going totally smooth and shaving everything clean in our “bikini areas”. As such we naturally started touching each other everywhere down there, and when she would touch me around the butthole area, I discovered that I really liked it. She lets me touch her butthole too, but not all the time. As for me, I can’t get enough of it. So that’s how I got into it.
I would love to go further and introduce small buttplugs and some light fingering for the both of us. Baby steps to get her more comfortable with it.

 

nope never

 

I lost a bet in a Yahoo Video Chat Room - Truth or Dare

 

First time was with my neighbour just a young lad at the time she was much older than me. It felt great but it ended quickly lost control cum too quick.

 

My first time was with a girlfriend when I was in my 20s. I really don’t know how we got there but do remember that it was easier than it can sometimes be and became a regular thing that we both loved. I was hooked.

Since then I’ve found that women either absolutely love it or have no interest at all. I’ve had women who said they’d never do it, try it and become totally into it and one that was so into it that she prepped like a porn star and it was an expected part of every session.

Once I get a woman to cum from anal, she’s desperate for it thereafter. Apparently that’s a very different kind of orgasm.

I’ve never been with a woman who wanted to penetrate me though. Not sure how I’d react frankly.

 

A neighbor showed it to me, and then we practiced for a long time.

 

This response is incredibly accurate.

My first was with a FWB in my early/mid 20s, she was in a very pitiful marriage, they only got married cause she got knocked up, they had no sex life, me and her had incredible chemistry and the sex was unreal and unlike her hubby i did my best to make sure she had an orgasm, one night as we were texting she asked if i'd ever done anal, i said i hadn't and she said neither had she but she'd always wanted to try she just never met anyone she trusted enough, not long after she was eager to give it a try, there was a lot of lube and it went in a little easier than expected and she got a lot more of it a lot quicker than expected.

In my experience i've met plenty that said they had no interest, only to try it "just once" and LOVE it

Had one FWB, very vanilla in bed but had an incredible ass, i started out fingering her ass while eating her pussy or fucking her doggy style, after a lot of convincing and lube she let me in finally, that first time she insisted she didn't like it and it was painful, then a few weeks later she showed up for a booty call, she was a little drunk and much to my suprise asked for anal, it became a regular thing after that.

Another FWB, first time i talked her into it ended up having a full body squirting orgasm, took us both by suprise and she was hooked.

Had a co-worker fuck buddy, i was late 20s, her early 40s and her sex drive was always in over drive she watched a lot of porn and hubby was vanilla. Said 2 husbands over 20ish years neither had ever wanted to fuck her in the ass, claimed she'd fingered her ass but never worked up the nerve to try anything bigger, she was also a squirter and anal took very little convincing, then she was hooked and she was the pornstar type and would prep for it, we quickly escalated to DP with toys

 

I did it with a G/F at Uni, she was a virgin and we were spooning and I was rubbing my wet knob up and down the cleft in her buttocks and it just went in. I still remember the feeling of the hole opening up round me. As she didn't pull away or pull it out again I asked if I could go on, so I did and shot into her ass. I did it four times over the next week or so before she lost her virginity, but she still volunteered it to me every so often. "Do you want to do it in the back one?" was her usual way of saying it. I even remember doing it as a quickie, no foreplay or touching her, just bend her overm, drop her pants, into her ass and cum. We were together for four years before she told me it was 'horrible' and she hated it. My next G/F was a nurse and we were together for seven days before I just put it into her ass one night, and she was happy enough. We did anal all the time, there were times I had to actually make myself do 'normal' vaginal sex in order to keep her happy. My current partner of many years now hates it, did it a few times to please me, said it was 'horrible' (same phrase as the first girl!!) and now will never do it again no matter how much I try. I miss it but it has to be both agreeing to it, or not at all.

 

For me, it became an obsession to know what it felt like to be a woman getting fucked; then one Friday night I was home alone watching porn, stroking at my leisure, when the man in the scene before me pulled out the woman's pussy, moved downward, and pushed that hard, slippery cock balls-deep in her ass -- I thought, "Damn, he could be doing that to ME!!!" That was hardest, hottest, longest cum I ever had, and even while I was hanging on to my wildly bursting dick, with that scalding hot cum raining down all over my face & chest & hair, I knew that I would do whatever it took to feel a hard dick probing MY ass like that! I've since been fucked many, many times by many different hard, man-hungry men and LOVED EACH TIME IT'S HAPPENED ...!!!

 

When I was in my early teens me and a friends found some jerk book on the side of the road. So we took them into the woods to look at them. Most of them were straight but a few were gay. So we are looking and we are both getting hard, then we decide to get naked and start jerking off. When we got to the gay books that's when we started think about what we were seeing and if we wanted to try it. First we just started rubbing each others dick, then we sucked each other and thought we may be on to something that felt really good. I tried to put my finger in my ass and found out it didn't work dry. I spit on my finger and started playing with my asshole, then I finally slid my finger in and told him that it felt good. So now we are both naked fingering our buttholes with rageing hardons. I got his dick good and wet then he slid it in my ass it hurt but felt good too. I think the load he put in my ass would have filled a quart bottle. After a while of my ass dripping and telling him what it felt like it was his turn. That was the first time for either of use had shoot a load in anthing other than our hand. We spent a lot of time naked in the woods after that. I have loved have feeling something in my ass for over fifty years now. To tell the truth there's a dildo in my ass now and it's been there for the last three hours.

 

^^^ Has one of those stand up desks.

 

I learned from a kid down the street and we use to mess around when we were both about 12 years old. We would jerk each other off and then started sucking and it eventually lead to anal.

 

We started with soft silicone buttplugs and just graduated to the jeweled polished plugs which feel more stimulating.They are Fun