What/Who got you into Anal Fun

Well that does give me some ideas or maybe a kneeling chair.

 

I used to lube up my wifes ass cheeks and slide my hard cock between them. Kind of a fun way to masturbate. Every once in a while the tip of my cock would catch on her asshole and she woulld let out a gentle and very quiet moan. After some discussion later, we did the same thing in the same position and she took it up her ass. It was a LONG process to get it in there and she sobbed while taking it. I'm not small so she was a champ. But she liked it up there once she got stretched and it went in. Years later a masseur who gave me a happy ending unexpectedly slid her middle finger up mine to trigger my climax and I learned how wonderful it felt. Now, it's just a normal part of sex for me.

 

A boy partner of mine showed me how it feels, I was 12, he was 13.

 

I’m would love to hear more

 

Not public

 

Once when my wife was giving me a blow job she started fingering my butt. I told her it felt good so she slid a finger into my asshole. I thought I was going to cum then. Over the next several months we progressed to using a dildo on me. It made me super hard and I would cum really hard. She told me that the real thing felt even better and I should try it
After much discussion in which I established that she was okay with it, I tried it. Only wish I would have been doing it sooner. When I told my wife about it she said it would be okay with her if I had sex with a guy when ever I wanted as long as I keep having sex with her. What a deal. I get to have my cake and eat it too. I started sucking the guy also. I now have sex with my boyfriend about twice a week and with my wife about 3 times a week. Life is good.

 

As a kid I was often constipated and my mother regularly gave me mineral oil of milk of magnesia. If those didn’t work, she’d get her red enema/douche bag and give me a full enema. I found it painful and hated it.

Then, one time when I was 14, I got a strong erection from her doing it which I tried to hide. As I sat on the toilet, the enema’s expulsion felt wonderful. I began beating off and had a massive ejaculation as the warm water was spurting out of my ass. Shortly after that when I was alone in the house I decided to give myself an enema and beat off as it was flowing out. Again it felt amazing.

Over the years I’ve had many butt plugs, prostate massagers and other anal toys. I’ve learned how to have a prostate orgasm when in a hot bath with my massager. I still love a good enema.

 

My first serious girlfriend used a dildo on me, graduated to a strap-on, the talked me into the real thing. Every step along the way I was certain I wouldn’t go any further. I was wrong, happily.

 

Same here. I wouldn't expect her to try anything, I wasn't willing to try myself.

 

My wife and I were having sex one night and it had started out with me using a vibrating dildo on her pussy. It was a fairly large on at that. I had used it on her clit and while she was cumming I put it inside her until she almost begged me to fuck her. Once I was on top of her going to town she had that dildo in her hand and was teasing my ass hole with it. The vibrations were driving me nuts. So I reached behind me and slid the thing in. She held onto it while my thrusting caused it to stimulate my prostate. It didn’t take long before I had an incredible orgasm.
I think she was very surprised that I liked it so much. We had tried anal once with me putting my cock in her and it hurt too much. So I think she wondered why it was so good for me. And possibly she was worried it had awakened a bisexuality in me. Little did she know it was all ready there.

 

My best friend (femme) on this site got me to thinking about it more and more, and then my Baby Love decided that we should try it, that he should be the guy to pop my anal cherry. We both loved it and now it's a standard part of our sex. At least 4 of our FWBs fuck my ass every time any of us get together.

 

Bet I know who your friend is…LOL! If it’s who I think, she should put out instructional videos!

 

When I was about 10 years old I started playing with my butt and it felt good so I started sticking things in it which felt even better. I’m 67 now and have numerous butt plugs and realistic dildos

 

I had my first anal amount a month ago. Alcohol was involved and the guy was much younger. He kept telling me my butt was built for anal and his dick was small, so I went ahead and let him take the plunge. It actually felt incredibly good.

 

Good way to start with them smaller! Glad you enjoyed! Did you cum or just felt good?

 

It just felt good. He came quickly. lol

 

It just felt good. He came quickly.

 

Darn! Experience is needed to fulfill your needs first;-) Sorry!!

 

The inexperience of youth. lol