What was your first anal sex like?

Contributor: RonLee RonLee
Quote:
Originally posted by couples1
My first time having anal sex was about two years after I got divorced. At the time I had a very good male friend that used to accompany me to functions and events. He works with me and I had known him for quite a couple of years already. He also ... more
Ah my very first GF and I had anal rather than vaginal sex because she was, with good reason, terrified of becoming pregnant. I must have done it right because even after we began having regular "conventional" intercourse she asked for anal quite frequently.
11/28/2014
Contributor: MrClark MrClark
My first girlfriend was already experienced with anal sex; however, she knew this was something I was curious about. I'd done significant amounts of reading and had experience playing with toys anally myself, which kind of is a first anal experience on it's own. Anyway, after we had been dating for a while and began having vaginal sex, she asked if I wanted to try it while we were having sex one evening. So after taking a break so she could give herself a quick enema, I started slowly playing with her anus with my fingers of one hand and liberal amounts of lube, while kissing her. Once I'd worked her up to the point three fingers could be inserted, along with quite a lot of lube she told me to fuck her in the ass. Doing it in missionary it was tricky to get it in the correct hole initially, which I seem to find to be the case even now; however, once I was in it was quite the experience helped in part that my ex could get off through anal sex too. I struggle to ejaculate through sex; however, had one of the most mind blowing orgasms when my ex came while I was in her butt and her sphincter began clamping down on me while I was in her.

My personal experience with anal happened when I was in middle school and have no real memories of the experience; however, the impetus for it was that I found some porn with anal sex, anal toy play, anal fisting, etc... I was curious both what it felt like as figured my butt should have the same kind of feelings as that of a woman. I also was curious if something as large as my fist or a baseball bat could actually fit and be as enjoyable as some of the women seemed to indicate. I've also found porn since with the opposite kind of reaction to such large insertions; however, from personal experience it can be enjoyable if done right. Thankfully, I took a lot of time to find info on what happened off set and good practices for anal play/sex before I got started. I think in a lot of cases people see anal in porn and think you can just take large objects anally with no prep/warm up/lube.
05/01/2016
Contributor: Andykh Andykh
My first experience was on a drunk nite with my wife and i and it was pretty painful. But since then it hasn't been no where near as bad
05/01/2016
Contributor: Tasha Tasha
Quote:
Originally posted by sexcandy12
for both men and woman, how was you first time getting it in the ass? much pain? not as bad as you thought?? was it accidental?
I've been masturbating anally basically since...I started masturbating so when it finally came time to have sex, I asked my partner to try it. (I prepped for it before hand.) The look on his face was priceless. He wouldn't do it. (Youth and inexperience.) I don't think he thought of me the same ever since. LOL

My second partner ever was more than willing to try it and thank goodness it turned out great. I ran the show and had to coach him to start slow and work it and out easy, but he did well. I was even able to have an orgasm from it...which actually made him cum too, but I was totally fine with the outcome. I was actually just happy to have finally tried it and finished without any embarrassments or "casualties", lol.
01/05/2017
Contributor: Nanuk Nanuk
Living room. Leather couch. When we figured that didn't work, we went to the carpet. Rug burn. Hit my head on the coffee table. Not enough lube. Two teenage gay boys that had no idea what they were doing. It's pretty laughable now.
02/02/2017
Contributor: RonLee RonLee
Quote:
Originally posted by Nanuk
Living room. Leather couch. When we figured that didn't work, we went to the carpet. Rug burn. Hit my head on the coffee table. Not enough lube. Two teenage gay boys that had no idea what they were doing. It's pretty laughable now.
LOL!
Oh, I do indeed understand that sort of thing.
Been there done that myself, granted quite a very long time ago.
02/02/2017
Contributor: xdresserx xdresserx
Quote:
Originally posted by sexcandy12
for both men and woman, how was you first time getting it in the ass? much pain? not as bad as you thought?? was it accidental?
It went well for me. I had used various sizes of dildos on my ass for years and had a good idea how it would feel to have a real cock in me. Some of the dildos which i used were bigger by far than the first cock which I rode on, so I knew that I could take it to the hilt. There were new sensations with a real cock, the heat of his cock was a good feeling and also the fact that I could actually feel his pulse as his cock throbbed inside me. I ended up cumming strongly without even touching my cock. My prostate had become very aroused and I had the hardest erection ever. A great sensation.
01/12/2020