Your honest ANAL experience

[fireman0922]

Anal is subjective. Some like, some don't ......!
Let's see what it has to offer. Share your HONEST ANAL experience, the does, the donnots, the pros and cons, the best and the worse.
Help us understand the concept better by sharing your experiences.

To be honest, I haven't tried it only because I'm scared that it would quickly turn into something ugly and uncomfortable.

I have always fantasized about about anal sex, maybe it's the naughtiness, the taboo.....but always was turned on by the thought of it.
Then in my mid 20s I met a woman who was willing to let me try. It was absolutely amazing watching her asshole stretch around my cock as she lowered herself back onto me. I was hooked immediately!.
After that I always told the women I dated I was interested, some where willing, some were not. I always loved when a woman who had a bad past experience with anal was willing to let me try. It became a challenge to me to change their experience. I loved going slow, taking my time, slowly stretching them until they were ready, it was always a huge victory in my mind when the woman ended up loving anal.
In my 30s I had a girlfriend who was open to the idea but very hesitant. So it took me a while before she left me try. Whenever I'd go down on her I would play with her asshole, just massaging at first, then licking, eventually she started letting me finger her. Over time it became our normal routine every time I'd go down, I'd have one or 2 fingers inside her ass, her ass was definitely ready but her mind wasn't there yet.

One day while she was sucking my cock she looked up at me and asked what my fascination was with anal sex, as she returned to sucking my cock, I was explaining my answer as best I could. She then said, "what if I wanted to finger your ass?" As she asked the question her fingers were already sliding between my ass cheeks and once her finger started massaging my asshole it felt really amazing. My response was "go slow like I have done with you" She reached over to the night stand and poured some oil on her hand and went back to my ass. I spread my legs giving her better access. As a dominant male this was very unnatural and I felt very vulnerable but I stuck with it.
She started to massage my asshole then slip on finger inside slowly, allowing me to relax then she'd go deeper....taking her time.
Once I relaxed enough and she was able to finger my ass she resumed my blow job. She had me cumming in seconds, to this day I have never had more powerful climaxes than from getting fingered and blown at the same time. It's always so fucking intense.
That same night she let me fuck her ass for the very first time. Anal sex became a regular part of our sex life. She said she always liked vaginal sex better, but anal was a very close 2nd.

 

[lokiboy]

Anal is subjective. Some like, some don't ......!
Let's see what it has to offer. Share your HONEST ANAL experience, the does, the donnots, the pros and cons, the best and the worse.
Help us understand the concept better by sharing your experiences.

To be honest, I haven't tried it only because I'm scared that it would quickly turn into something ugly and uncomfortable.

I was always interested in it ever since I learned (porn) that it's something you can do. Every gf I've had, I've at least slipped a finger in her ass. A few have let me use toys, and 3 have let me use my cock. My first experience was perfect - sexy gf, anal virgin too, was happy to try it with me (both really loved each other), I properly prepped her, listened to her, and went slow. I talked her through it, telling her how good it felt, how sexy she was, etc. I fucked her for a while, enjoying the feeling (she did too, said it only hurt a little during penetration), and was able to fuck her hard and fast when I was ready to cum. We talked after and she told me what she enjoyed about it.

The next girl I did it with was almost the complete opposite. It was not a loving relationship, we were bad for each other. But I told her I wanted to do it one night during regular sex (which was so bad that I was about to stop anyway, without even cumming), and she agreed. She'd never do it before, but I only spent little time prepping her, with just 'natural' lube, and started guiding my cock in. She made an 'ah!' sound when I first penetrated her (just got the head in), and instead of asking if she was ok or wanted me to stop, I said "I just need need to get it all the way in", to which she nodded (concentrating, with her eyes closed). I thrust forward a second time, not hard, but it went all the way in. She made a louder 'AH!' sound, and then I held still and asked if she was OK. To which she said 'uhmm.. yes.. I love it in my ass!'. I don't know if she was lying to make me happy, or if she actually liked it, but I figured she was an adult and knew I would stop if she wanted. So I proceeded to fuck her ass exactly how I felt like fucking it - long medium-paced strokes at first, then quick faster/harder short strokes after a while. I wasn't trying to hurt her, but I also wasn't worrying about it. We went to sleep after I came in her ass. The next day, I didn't ask her how she felt or liked it, but she must have at least a little bit because she smiled, turned around, bent over, and spread her ass, for me to fuck it again in the shower that morning.