This happened a few years back and was the first time I had a vibrator in my ass. Since then I've had it a few times and once with a strap on.
My gf at the time was not keen on anal, she had never tried it but just didn't like the idea. I tried to persuade her so many times and it was a hard no. So I tried one last role of the dice. I said what would it take to let me fuck your ass, and she said 'you know my vibrator how about I use that in your ass and if you take it all you can fuck mine'. I had no experience of anything I my ass at the time and it looked pretty big but I really wanted her so badly. I said yes.
So we went out one Saturday night and had a few drinks and when we got back it wasn't long before we were kissing and cloths being torn off. I was hard instantly looking at her cute curves and shaven pussy and just had to taste her. She lay back on the bed and beckoned me between her thighs and I worked my tongue around her sensitive clit and then down dipping first into her pussy and then her tight ass.
As soon as I touched that puckered hole she shook her head and said 'you first'. And out came the toy and the lube. She playfully pulled me onto the bed and lay me down face first onto a pillow. I lay still as she poured lube between my ass cheeks then using one finger she teased my asshole before pushing the finger inside. I shivered. She slowly worked up to two fingers. Then more lube and I felt the buzz of the vibrator tingle my hole. She was clearly enjoying this so I played along and lifted my hips so she could see my hard cock and balls as she played.
The toy went in and I felt it vibrate deep and intense right though to my balls which she was now gently massaging before working along my shaft. She knew just how to touch me stroking from root to tip as the lube added to the motion. I was enjoying it a lot more than expected. I looked over my shoulder and asked if it was my turn now?
She pulled out the vibe and dropped it on the floor and went on all fours. Her fingers teased her pussy and she rubbed her clit hard. I lined the tip of olmy cock against her asshole and the length was already slippery with lube. I added more for good measure and pushed the tip ever so gently. She sighed as the tip popped in. I held it there so she could get used to it. Then ever so slowly pushed deeper.
We took out time slowly building to a good pace all the while she stroked her clit and fingered her pussy. I held her hips in my hands desparate to cum in her ass and feeling the pressure build. I could see she was building too...I increased the pace and so did she. We fucked harder and faster until I shouted I was going to cum and then blew my load deep in her ass. Shaking and twitching I emptied every last drop. And this set her over the edge cumming and gripping me tighter milking my cum.
Let's just say it was the first but it wasn't the last time we both enjoyed anal 😉