My first time was with the man who would become my husband. We had played around a bit teasing each other's asses (there was no way I was going to let him if he didn't have some skin in the game!) We were going home for Christmas and I knew we would have so stop overnight somewhere since we were leaving after work. So I decided I would give my boyfriend a very special Christmas present.
I brought along lube and a couple of toys and a sexy little baby doll nightie he liked. We stopped in some no name roadside motel for the night in heavy snow. After we settled in, I went in the bathroom to change. when I came out he was very excited. We started to make out and at the right point I started to play with his ass. He eagerly started playing with my ass. Caressing my little pucker with his tongue and finger. When I handed him the lube, his fingers grew more bold.
He was very gentle with me (as I knew he would be). When I handed him our anal toy he was really excited since we had only used it once before. I told him to take it slow since this was part of his Christmas present. Well he ate my pussy and teased my ass with the toy, until finally I relaxed and he slid it in. He took it real slow letting me accept the toy. All the while playing with my clit and lapping away at my pussy.
After a while I was really excited and the toy felt really good. So I asked him if he wanted the rest of his present. He almost shouted yes, and then I told him he could cum in my ass. He was so eager, so I reminded him to go slow and easy.
He rolled me on my knees and played with the toy in my ass for a while until I said I was ready. He left the toy in me while he lubed his cock. When he was ready he gently slipped the toy out of my ass. Then very gently I felt his cock press against my ass. I dropped my head and shoulders down onto the bed and told him to go real slow but stop when I tell him to. He grabbed my hips and slowly pressed against me. Since the toy was almost as thick as his cock I was well prepared. When the pressure built on my puckered hole, I pushed back on him and his cock promptly popped out and slid up my ass crack. He apologized and I assured him it was alright. He lined up again and pressed against me slowly. I pushed back and this time relaxed enough the head popped in. There was that intense burning sort of pain that everyone who has done anal recognizes.
I gasped and I guess moaned because he asked if I was alright. I told him to hold still and he stayed there -- gripping my ass in his hands and the head of his cock inside me. Because I was so turned on, well lubed and reasonably stretched from the toy the burning sensation started to pass pretty quickly. I'm sure it felt like forever for him, but eventually I told him to push a little bit in. That wasn't so painful, but so intensely invasive -- my boyfriend's cock was sliding into my ass. A year ago I'd have said no way, but now my ass was his Christmas present. Slowly bit by bit I had him slip his cock into my ass. He kept telling me how great it felt and finally, he was buried in all the way.
He was so gentle with me. After just holding his cock in my ass, he slowly eased out just a little, added lube and then slid back in. Over I don't know how long he got me to further relax and his (frequently re-lubed) cock could slide farther and farther. Eventually he was fucking my ass with long slow strokes, swearing about how good I felt. I just relaxed and let him have his fun. His cock felt pretty good in my ass -- although I think it was because it was his cock and I so wanted him to enjoy it.
I didn't get off on it, but it felt good to give him so much pleasure. Eventually he came in my ass and his present was complete. Clean-up wasn't horrible, but it certainly was more difficult than regular sex. We have done it a few times since, but I really need to be in the right mood and feeling confident about all of my bodily functions.