Hmm, I may be odd in that I have always enjoyed anal stimulation with previous boyfriends.
With my current fuck buddy I was the one who bought up the topic of anal sex. He'd done it before and heartily agreed.
After really good vanilla sex followed by oral he lubed up and pushed the head in. There was some discomfort/pressure with the first couple of inches so he stopped and let me get used to having him there for maybe a minute or two. We were doing it doggy style and I remember he gently massaged the small of my back and butt. Don't know if that helped to relax my sphincter, but it felt nice. Next thing I knew he was balls deep, and I yelped! Once again he did the hold still and back massage. Then started the long, slow strokes, he applied more lube and without even realizing it I was backing up to meet each thrust and soon I had my first anal orgasm. :05: The rest as they say is history.
:biggrin1: A butt slut was born.
I had asked some of my gay friends for tips, prior to doing it and they all agreed, that we should go slow, use lots of lube, and that I should be on top. When the time came it never even occurred to me to be on top. I like doggy style and I trust him so I knew it would be okay, and it was.
We have since tried anal sex in a variety of positions
Me on my back with my legs over his shoulders = hurt like hell.
Reverse Cowgirl = Very nice :05: bonus I can easily reach my clit
Cowgirl = Nice for easy clitoral stimulation, but awkward for my long legs.
On our sides (Spooning) with his top leg over mine = Very Nice
Doggy Style = Great! This is our personal fave. :smile: Feels great for him, feels great for me; we can both reach my clit for stimulation.
* NOTE: I can and often have an analgasm without clitoral stimulation. :05: Apparently this is unusual . . .
** NOTE: The first time we did anal he used a lubricated condom, the next week we went bareback. It hurt a lot more the 2nd time, even with lots of lube it was like being an anal virgin again. Never underestimate the usefulness of a condom. It definetely helped to grease the gate as it were. :smile:
My fuck buddy is average (7x5) not huge, so maybe if she were to try anal with a smaller guy first . . .