Hooked up with a girl who was REALLY into anal [M23/F19] | 2016

So there was a girl who I kinda knew because she had had this friends with benefits-style relationship with a buddy of mine for a little while. This guy told me a few stories about her and they always related to butt-stuff. He said that she preferred butt stimulation even over vaginal or clitoral stuff, to the point where one time they were doing a bit of heavy petting at a party when she put her hand down the back of her trousers and fingered her asshole until she came. For the rest of that night he noticed that she would occasionally sniff and lick her own fingers.

I didn't know whether to fully believe this guy, as it sounded like he was just boasting about having a kinky fuck-buddy, but I figured that I didn't have much to lose and said that I would be really interested in hooking up with her and seeing what she was like. My buddy was keen for the idea and promised to introduce me properly and talk me up at a party we were all going to be at the next week.

At the party my buddy was as good as his word and I had a few drinks with this girl and we got on well. I could tell that we were never going to be soul mates, but I found her attractive: she had a pretty face and although she was a little on the plump side with a round belly, but she carried her weight well and had huge tits. I told her my place wasn't too far away and asked if she was interested in coming back, she said that she was. When we got to my place we wasted no time stripping off. I sat on the couch and she sat on me. As we made out and explored one another's bodies, I was impressed by how her entire body felt soft yet firm, she wasn't floppy or saggy anywhere and her huge tits were capped with big pink areolas.

I have this strategy when I am trying to get girls into anal that I offer them a massage and gradually work my way to touching them around the butthole. If their body language is receptive then I take things further, if it isn't then I leave it alone. I thought that this would be a good strategy to use on this girl. So I offered her a massage, she enthusiastically agreed and we moved to the bedroom, where I instructed her to lay down on her front while I went and heated some oil. I spent a while massaging her back and shoulders before moving down to her legs, then moving back up her inner thigh. Her body felt amazing under my hands, she was so soft in places, yet still firm and tight. I put it down to her being young and also fairly physically active, despite being a bit overweight.

As I massaged further up her thigh, she spread her legs wide for me. I could see her pussy was soaking wet. As I glided my hands over her labia and her buttocks, she thrust her ass out slightly towards me in frustration and I saw her butthole clearly for the first time. It was lovely: completely hairless, almost as pale as the rest of her butt and it had that ever so slightly pushed-in look.

I spread her butt cheeks as I massaged the crack of her ass, careful to gently touch her asshole as I moved over it, but didn't apply too much pressure. I saw her asshole contract as she moaned and thrust her hips back towards me slightly. I pressed a thumb lightly on her asshole and I felt the muscles easily give way as it slid in. She bucked with pleasure as I pushed my thumb deep into her asshole. She writhed and quickly came as I masturbated her with my thumb. I kept my thumb in her asshole, but gave her a few seconds to recover as I realised that I hadn't even touched her pussy yet. I looked at and it was so wet that she was leaking out and creating a wet patch on the bed. I rotated my hand and with my thumb still in her ass, I put a couple of fingers in her cunt. It was hot, wet and quite loose. Encouraged, I put my other two fingers in her pussy and tried to touch my thumb to my fingers through the fleshy wall separating her asshole and her cunt, causing her to writhe and moan in ecstasy.

I spent the next half an hour or so masturbating her in various ways involving her asshole, cunt and clit, usually using two, if not all three at the same time. She seemed insatiable, cumming over and over. Usually I'm more than happy to pleasure a girl for as long as she needs, but in this case even I got to the point where I wanted to move on. Eventually I gave her one last orgasm and withdrew my now wet, sticky and incredible smelling fingers. I got some more hot oil, applied it heavily to my cock and pushed it in her ass. Even after all the fingering, I went in surprisingly easy. There didn't seem to be any pain, she just moaned heavily and pushed back towards me receptively, trying to get my cock deeper into her asshole. As I fucked her, I realised how amazing her voluptuous ass felt against my hips.

It had been a sexy evening and all the build-up ensured that I wasn't going to last particularly long. Before too long I began to shoot a huge load in her ass. As I started, she said, amongst her moans 'oh my god, I can feel you cumming in my ass!' (I asked her later and she said she could feel both the contractions of my cock and my cum shooting out into her ass) and clenched her asshole so tight on my cock it felt like it might snap!

After we were finished, I slowly withdrew my cock out of her ass. Some of my cum spilled out of her asshole, ran past her cunt and pooled with her pussy juices on the bed. I lay down next to her and we were so exhausted and satisfied that we just fell asleep covered in a mixture of oil and our own juices.

The next morning she woke me with an oiled titjob with her huge boobs, which felt amazing. After that we showered together and I gave her a rimjob; unsurprisingly she enjoyed it immensely.

Hope you enjoyed! Comments/feedback welcome.