What was the position that you lost your anal virginity to?

On my knees, back arched, looking over my shoulder to watch it go in. Then face on the floor turned to one side, drooling and babbling gibberish as he fucked me ridiculous... :D
 
I was fucking a FWB doggy, with a little bit of hair pulling, and when I slid my thumb into her ass, she started begging for it. So it was sort of mutual agreement.

It was her first time too, and we were both in our forties! What had we been waiting for, I wonder?

(In my case, it was pretty much waiting for a willing partner :) )
 
Standing up in the shower....it was a disaster...the ex wanted to show me that she wasn't as sexually inhibited as I thought she was, so on our anniversary we got a room looking over the ocean that had a hot tub on the balcony.....and after we had sex there, she suggested we take a shower together. Both of those events were unlike her, and I was VERY appreciative of her trying new things.

Then came the shower....it basically went like this:

1. We both soaped each other up....so far so good.

2. She suddenly turned and bent over and rubbed her ass against my cock - VERY nice.

3. She reached up and gripped my cock and placed it at the entrance to her ass....I was feeling lucky....this was perfect!

4. She then told me to take it slowly....so I told her to wait a moment and I'd grab some lube.

5. She was irritated that I would suggest that and ruin her mood....she wanted it...now....OK...

6. I pressed against her ass opening...just pressure, not forcing my way in....

7. She then starts the very understandable squawking about how it hurt, and that she knew this wasn't for her.

8. I tried again to get her some lube, but she wasn't having any of it...and pushed back further...which of course hurt more.

9. To her credit, she backed all the way up so I was fully inside her...but she then forbade me from moving at all because it hurt her.

10. I finally slipped out a short time later when I was no longer erect......

That episode described the sexual side of the marriage.
 
On my knees. It was an idea my hi school buddy and I came up with since our girlfriends wouldn't let us do it to them. We flipped a coin to see who went first. :D
 
Doggie style...he was drunk and the wrong hole got fucked. Not that much fun when you aren't expecting it.
 
No. It wasn't my hubby. I was single at the time and I do believe I shed a tear or two.:eek::eek:
The problem was I couldn't really stop him till he was done. ...I know...too much info...stopping now.
 
No. It wasn't my hubby. I was single at the time and I do believe I shed a tear or two.:eek::eek:
The problem was I couldn't really stop him till he was done. ...I know...too much info...stopping now.

Never too much info...we're here to listen...and sympothize. ;)
 
Cowgirl, facing him, in the back of a truck in a parking lot. We were both virgins before that, so I'm not really sure why we both decided we wanted to do that, but I'm glad we did. It was the first of many times with him and other men.
 
I did my first anal doggy style(boring), she was having a great time, as we made sure to go slow.
 
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