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 realized 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 ministrations and when she had me nude 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 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 cum. 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 through most of this, but I opened them to see what she was up to. In her other hand she held up a vibe, and she was stroking it with her greased hand. It wasn't very thick, maybe three quarters of an inch at it's 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. Gently but firmly circling it like water going down a 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. It was clear she was in charge of the pace and I wasn't going to cum until she allowed it. Thinking back I didn't even realize it was no longer her finger she was using to probe me.
When it popped into me, my cock throbbed in a way I never felt before. Each stroke of her hand made me moan and gasp, I was a mess. An incoherent ball of crazed lust on the brink of an explosion. But she didn't move the vibe yet. Just left me impaled like that. Gasping and sweating, my eyes glazed over when they weren't rolled back into my head.
She flipped the sucker on low and sat there, still and immobile. Her eyes riveted to the scene before her and her hand frozen at the base of my drooling cock, watching it twitch. Slowly she started to ease the length of it out of me as her hand corkscrewed up my shaft to the head of my cock her fingers dancing over the tip and back down.
At this point I'm tossing my head from side to side, hissing and begging for her to make me cum between moans and gasps. Every thrust causing me to grunt almost like a wounded animal. I may not have been tied down, but I didn't dare do anything to break her trance and cause her to stop either. She obliged, picking up the pace stroking my cock tighter and faster as she drove the vibe deeper and with purpose. Occasionally she would stop stroking and just rub the pad of her thumb over the head of my cock mixing my pre-cum with the already copious amount of lube drenching my cock. This has me pulling up the sheets now, balling them up in my fists. With each thrust of the vibe I was sure I was about to blow, but she managed to prolong things a bit by regulating her grip on my cock and changing the depth of her thrusts.
Just when I thought she couldn't find any other ways to torture me, she leaned close to my shoulder and traced my collar bone with her tongue. Then, after biting it she began to taunt me asking if this was what I wanted to do to her ass.
That was it. I never came so hard or so much in my life. The first shot launched so forcefully I almost hit my chin. Jet after jet of hot cum was squirting across my chest. My ass bearing down, straining to shoot the vibe across the room. It took minutes for the throws of my orgasm to subside. When I was done convulsing, I melted back into the bed unable to lift my head. I could hardly wait to get my hands on her ass and show her I can give as good as I got.