Who initiated your first anal experience?

The first time you experienced anal sex (either give or receiving) who initiated it? You or your partner? How did it happen? Who brought up the subject? Did you enjoy it? Did your partner enjoy it? Do you still like it and how often do you do it?

My first experience of anal came as a surprise. We had never really talked about trying it, one night myself and an ex where having a marathon sex session, probably about 3 hours of sex and orgasms with little rest periods in between. Anyway I was sitting on the arm chair and she was fucking me reverse cowgirl style, while she was pounding me my cock slipped out, she reached between her legs and grabbed my cock, she positioned herself over me a slid my cock into her, but it wasn't her pussy, she had put my cock in her ass, and she slowly began fucking me again. I was taken by surprise but was extremely turned on, I let her take full control and it was fantastic!! We both came within a few mins. We had anal many times after that. My wife now only allows anal once every few months, she really enjoys it when it happens tho!

So what are your experiences and stories? Don't be shy!!

 

The first time was with my long term GF when we were both young. Its not something I remember discussing at all, or even having any great desire to do so. But one night we were both a bit stoned, drunk and frisky and having nice sex - and - well, I just found at some point my cock right up against her asshole which was already nice and wet from her juices leaking all over it - and I just pushed it in, and we both went Ooh yeah!
I was very slow and gentle with her and with one hand played with her clit. We both came and fell apart on the bed happy. I said, that was my first time doing that - she said, me too!
Dont think we did it again after that though it was an enjoyable one off. Since then I married someone else and we went through a phase of doing it quite often, then we both sort of went off the idea, because really, up the vagina feels better. I do love to lick her ass though.

 

The guy did.
I think my attitude was, "why not?" It was quite okay!

Still do it after 25 years

 

Silk896 is "why not" your motto when it comes to all things sex play? I tend to have the attitude that I'll try anything at least 3 times to see if I like it, because you never can tell after just one go!!

 

First time for me and her was when I was 19, my gf was 17 and it was me who initiated it. We were at my house and I don't know why but I had the bright idea to try it and she was cool with it. Grabbed some baby oil from the medicine cabinet and lubed all up and then went for the gold. It was a bit painful for her as I was a dumbass not knowing what I was doing. Was great for me, not so much for her I gather, but it didn't turn her off and we had quite a few other anal encounters including one that blew my mind, but that's another story

 

My husband originally initiated anal play for us by licking and fingering. I was a little apprehensive at first but then started getting really turned on by it, eventually he asked if he could put his cock in my ass and we both loved it! Now we probably have anal every couple of months.
More recently I have been soooo horny at the thought of him getting penetrated anally and seeing him have a massive boner so I played around with his butt and lubed up my vibrator and gently inserted it. He was so hard and I sucked his dick until he came (which wasn't a long time) afterwards he was just like "ehh, it was ok" like he didn't want to admit he loved it :-/

Meanwhile I'm a bit wet just thinking about it.

 

Back then, it probably was. I think I had done pretty much the full gamut of hetero variants by the time I was 21 or 22.
Some good, some not so good.

These days, I'm a little more circumspect.

 

I was having vaginal sex with a gf in college when she suddenly rolled over flat on her stomach, spread her legs slightly, looked at me over her shoulder and gave me a big sweet smile. I'll never forget how it felt when I entered her, the tightness around the shaft of my penis and the warmth and softness of her rectum around the head. God, I wish I had that girl again!

 

Would you say you had more good than bad silk896? I've had good and bad, but I reckon the good out weighs the bad..... Had some good in your fair city too!! Stayed in the "Bundoora" area. (Not sure I spelt that correctly!)

 

i don't know, does me dropping the soap count as "initiating?"

 

Woman I was seeing. mid fuck she was on top. and suddenly stopped pulled off. Next thing I was aware of was a slightly strange feeling and when I put my hand down I found a vacant pussy . it felt great

 

My Master taught me. We had been together for probably four or five weeks. He had spanked me, and licked and fingered my little asshole to fabulous orgasms for me.

Over dinner at a white-tablecloth restaurant, He informed me that my ass would be welcoming His sizable cock later that evening. I was excited but scared too.

It was scary, a little painful and very wonderful (twice that night and once the next morning).

We've done it almost every day for the eight months since then. No longer painful, ever more wonderful.

 

That's also how I got my first taste of anal. The fact that she simply grabbed my cock and guided it in her asshole was amazingly kinky, and it didn't take long until I had to ejaculate in her ass.

 

Anal was not something we discussed but was something I was interested to try. I started out by licking my girlfriends asshole then fingered her with some lube while giving her oral.

This continued for a few months, then during doggy I'd have her lie on her stomach and take my cock out of her pussy and rub it across her asshole; we never discussed Anal but she is always happy to try new things so one morning I was doing this and with some lube gently gave it a go. Only really just got the head of my cock in the first time, she was/is so tight that taking it out practically dragged the condom off that first time.

We now have Anal probably every other day, always clean so no problems there and it feels great without a condom. I'd still love to fuck her ass balls deep but we are still taking it slow and only take the head of my cock during anal

 

first time I masturbated to words alone!

 

So may I ask bluntly, since there wasn't an enema involved... was there poo???

 

Nope!! Perfectly clean afterwards, actually now that I think of it, I had anal sex quite a few times and there's never been any mess. Always showered afterwards though just to be sure. Hot shower after great sex usually leads to a little more fun!!

 

She must have came prepared that night so!

 

I was a teen and did not want to lose my virginity so I agreed to it. It hurt and I pooped on him a little- I was horrified!!! We did not use lube either!

 

"Bad Santa". "you probably couldn't poop right for a monh"