This was just short of half a year ago, so I don't remember all the details, but it keeps popping up in my fantasies so I thought I'd share.
It's also my first story here, so be gentle ;)
For a bit of background, her name is Lina(-ish), she's 22 and I'm 25. We met eachother a year and a half ago and have been in an on/off sexual relationship since then, due to longer trips out of the country.
We hadn't had sex in a whiles; she didn't like to on her period, though it doesn't bother me, and before this we had both been out of the country for a bit. Needless to say I was really horny. We were together al day for a few days getting hot and heavy when making out, but no actual intercourse. Sucks! She tries to get me off with her hands and mouth, but due to medication making it difficult for me to cum it was to no effect, but to make me even more turned on.
So we're on the bed, mostly naked, making out.. I'm licking and sucking and biting her nipples, my hand is caressing her lower back and thighs and eventually make it to her clit. She's twisting and turning and moaning that it isn't fair that we can't just fuck. I half jokingly tell her she has more options than just her pussy.. She just let's out a small groan and then goes back to moaning while I finish her off with my fingers.
She goes to the bathroom and then she comes back she lays on the bed, hiding her face in the pillow and shyly looking at me from time to time. When I ask what's up, she quietly asks "You would really like to try anal, wouldn't you?". And ooooh yes would I! I love anal! She asks me to get a towel and be slow with her.
I grab a towel from the closet and go into the bathroom. Now where did I leave that oil I got for my beard? Nowhere to be found? CRAP! The babyoil! Where is the baby oil?! In the bin when I left my old place? More crap.. Into the kitchen I go.. All I've got is this super expensive handmade olive oil from italy my mum got me.. What the hell! This is anal we're talking about! So I poor some of it into a smaller container and head back into the bedroom. And there she is, all naked and lovely..
We lay the towel out on the bed, and she lies herself down on her stomach.. I kiss her all over, and start caressing her lower back again, making my way down to her butt. Some oil on my finger and it slides in.. All the way in.. And not a single complaint about it hurting, unlike my ex.. She just says it feels "unusual" but to keep going. God she's great! I slide in another finger, and while she's starting to feel it it doesn't take long before I'me three fingers palm deep in her virgin butt hole.
I get her up on all fours and position myself behind her. Place my dick and her ass and slowly insert it. Again she is in no pain despite it being her first time, so quite soon after I'm going at it, loving the feeling. As I said before I was on medication making it hard for me to cum.. But I'm fucking my fuckbuddy in the ass for the first time, she's giving out slight moans and fondling my balls.. After just a few minutes I feel my orgasm building up and I loudly empty myself in her behind.. She giggles and smiles at me and she says; "well.. That was quick" before kissing me passionately.