First anal

It was pretty damn amazing for me. My first time taking it in the booty was also his first time giving it to a booty. It was about 12 years ago.

Why? Uh... We both wanted to. We had the opportunity and the time. We both really enjoyed it.
 
It was pretty damn amazing for me. My first time taking it in the booty was also his first time giving it to a booty. It was about 12 years ago.

Why? Uh... We both wanted to. We had the opportunity and the time. We both really enjoyed it.
What did you do to prepare for it
 
What did you do to prepare for it

It just so happened that I was conveniently already on the "prepared" side when it happened. He showed up right after I had taken a shower and my uh... Digestive situation wasn't an issue.
 
  • Like
Reactions: Peter Brown II
It just so happened that I was conveniently already on the "prepared" side when it happened. He showed up right after I had taken a shower and my uh... Digestive situation wasn't an issue.
I gotcha! Did you use toys first at all
 
It was romantic as all things sexy-time we're with him. My first sweetheart. My first sexual partner. I was his first too. We were poorly supervised and appropriately up to no good. It was a little painful at first, but then it felt great. I wasn't very orgasmic at the time, and almost nothing actually gave me an orgasm. I don't remember details. It was forever ago. I just remember we were both curious, and both pleased with how it went. After, we cuddled for a while, then he played his keyboard for me. So sweet.
 
First time giving anal was a kinky hook up where I pretended to know more than I did. Thankfully, my instincts are keen.:imp:

First time receiving, gender play and ass play with a more experienced partner. They had really good instincts too. :p
 
My first experience with anal was a total nightmare :(
We were having sex and he turned me over and just shoved it in my ass and tried the classic "oops, wrong hole" line. I wasn't expecting it and the pain was so excruciating and paralyzing I could barely make a sound. The asshole took advantage of this and actually continued fucking me, I had to buck him off to get him to stop :mad:

Most of my friends had similar first times so no wonder anal gets such a bad rep.
Considering my totally traumatic early experiences I'm surprised I'm so in love with it now :heart_eyes:
 
My first experience with anal was a total nightmare :(
We were having sex and he turned me over and just shoved it in my ass and tried the classic "oops, wrong hole" line. I wasn't expecting it and the pain was so excruciating and paralyzing I could barely make a sound. The asshole took advantage of this and actually continued fucking me, I had to buck him off to get him to stop :mad:

Most of my friends had similar first times so no wonder anal gets such a bad rep.

That's flat out Rape.
 
That's flat out Rape.

He was an asshole but I wouldn't go that far.
We were inexperienced and I'm sure most guys try the 'wrong hole' strategy at least once : unamused:
When I said "paralyzing" I meant it literally, I didn't scream or say stop or even "oww" or anything until the moment I bucked him off.
I gave him the benefit of the doubt.
 
  • Like
Reactions: TheUnihorn
He was an asshole but I wouldn't go that far.
We were inexperienced and I'm sure most guys try the 'wrong hole' strategy at least once : unamused:
When I said "paralyzing" I meant it literally, I didn't scream or say stop or even "oww" or anything until the moment I bucked him off.
I gave him the benefit of the doubt.

I would totally go that far, and I would advise any man reading this thread to take note of that. No guy has ever done that to me. Every time I've had anal I knew it was coming and gave permission.

I know, it is literally paralyzingly painful... And I'm sorry you had to feel that pain.
 
My first experience with anal was a total nightmare :(
We were having sex and he turned me over and just shoved it in my ass and tried the classic "oops, wrong hole" line. I wasn't expecting it and the pain was so excruciating and paralyzing I could barely make a sound. The asshole took advantage of this and actually continued fucking me, I had to buck him off to get him to stop :mad:

Most of my friends had similar first times so no wonder anal gets such a bad rep.
Considering my totally traumatic early experiences I'm surprised I'm so in love with it now :heart_eyes:
When did you first start enjoying anal?
 
My hub wants me to try anal, but I'm not really certain at all about wanting to try it.
 
  • Like
Reactions: BetterFuture