I was dating this girl and at the time, neither of us had much experience with anal sex. I wanted desperately to try it with her because she had the most incredible ass! I told her as much and she thought she was being cute when she said, "Only if I can do you first." Well, I wish I could have captured the look on her face when I said yes. It didn't take long for her to realize I was serious and she decided to go through with it.
She didn't bother to strip, I think she thought I might change my mind and was anxious to see my reaction. She definitely was turned on being in control. She removed my clothes completely, taking her time so I could contemplate her every move and when she had me nude she sat between my legs positioning me on my back completely stretched out.
She made a fuss over drizzling the oil over my cock from some height and then gripping it and tracing each vein as she stroked it; Her hand inverted going up and over the top and right side up coming back down. She brought me to the edge several times with the sweet friction of her grip on my cock-head but refused to let me ejaculate. I was literally humping her hand before long. And I was moaning like a banshee, rapid shallow breathing, and almost pitiful moaning.
When she was ready, she left me there twitching and straining. My eyes were closed in pleasure through most of her ministrations, but I couldn’t resist opening them to see what she was going to do next. In one hand she held up a vibe, which she was intently stroking with her other greased up hand. It wasn't very thick, maybe three-quarters of an inch at its thickest and barely six inches long.
I didn't think it was possible, but I got harder at the sight. I never had anything in my ass before not even a finger, so this was a giant leap for me. Logically, I knew that the muscles in my ass were connected to the ones that make you cum so I was totally into it. I bent my legs at the knees and scooted down closer to her so she could fulfill her end of our arrangement.
First, she took one of her fingers and traced my anus. Then, gently but firmly she circled it the way water does when going down the drain. If I was moaning before, I was gasping for air now. After slipping her finger in, she eased it out and back several times, testing for resistance before pulling out and going back to jacking me off, satisfied things were ready to proceed.
She pressed the cold head of the vibe against my tight hole and I almost scooted down on it trying to recapture the ecstasy from her prior invasion. But she held me in place with a vice-like grip on the base of my cock preventing me from moving.