Describe your first anal sex experience with a woman?

I haven't had anal sex with a woman...probably because I am a woman and we don't usually do the anal play together when we fool around. The first time my then boyfriend (now husband) and I had anal sex was quite by accident. We were on his (Army) roomates bed and he was pounding away on me doggy style and it slipped out and went right up my backside. OUCH! He was quite an ass about the hole thing. Instead of staying and consoling me--he ran off to "wash" himself. What a jerk huh? I couldn't sit without wincing for a week. A wonder I married the guy a few years later. However it' a very different story now. We know how to have very pleasurable anal sex (while DPing is nice too) so we've come a long way!

my first wife finally relented to me for anal sex . I dont remember using any lube and I could only get the head in her butt. It was hurting her and I held still hoping she would get used to it and relax. She didnot and she moved around a little and clenched her anal muscles which helped cause me to cum. I didnot thrust into her ,instead I just felt my penis swell up and I ejaculated inside her rear end.It was good for me as I got her anal cherry ,but I was unable to thrust into her ass.

Not long after we had gotten married my wife and I were watching a sex show in Mexico. There was a young couple having sex on stage and when enough money was tossed on the stage for them to have anal sex they did so. The woman really enjoyed it. Her pussy was dripping wet and she came several times. Later, in our motel room my wife wanted to try it. It took a while but before long my wife was having huge orgasms from anal sex.

I was 16 and going out with a girl who had low self esteem and would do anything I wanted. Mostly I just liked her to suck my cock, and sometimes vaginal sex, but I eventually suggested anal sex and she complied without question. It was OK, nice and tight, but there was some crap on my cock afterwards which turned me off. So I went back to asking her to blow me constantly.

where in Mexico did you see the sex show?

My first anal sex experience with a woman was when I was bartending. She was an older Redhead, with a great mature body.We went up to her place and started to fool around. She went from sucking my cock, to sucking and licking my ball, then going further over my taint, then right to my asshole. She licked and ate my ass which felt unbelievable. There was no way I was about to stop her, nor do I think I could have. She was in a frenzy, licking and little bites with her tongue poking in. That was soon replaced with her finger, first one, then two, then three. She began to suck my cock again while she fingerfucked me with three fingers. I was putty in her hands. Not finding any resistance to her advances, she went for the dildo and proceeded to give me my first anal experience with a woman. Maybe this wasn't the story you expected, but it's my first.