first anal

[alexossale]

I didn't see anywhere to put this so here goes
I met my girlfriend shortly out of high school. She lived at home with her parents and sister. Things moved along from groping to heavy petting to oral(lots and lots of it!) after a while after getting both of us good and sloppy wet she would slide the lips of her shaved pussy up and down my dick(but no penetration). She would also slide me up and down the crack of her ass.

Then one night she grabbed my cock and put it up against her asshole. I moved back for a second and she whispered "where are you going?". My heart raced and I said "I'll go wherever you want." As she pushed herself back I couldn't believe how tight she was and I heard her let out a soft moan as she grabbed the bed. I let her control how fas/far things went. Once she got the head in she began to rock ever so slightly. After a bit I asked if she was ok, she didn't say anything just nodded and pushed in the last bit. As I reached around to her pussy I found her to be absolutely soaking wet, I mean thick wet pussy juice. After hearing her moaning into the pillow and digging her nails into my leg, pulling me into her, I came hard. After cleaning off her ass and back, she asked how as it, I was blown away, I was amazed she did that! I asked how she did, she said it hurt for a second or two then felt great and once I started fingering her it sent her over the top.

We've revisited it quite a few times since

[alexossale]

I think she wanted to be a "good girl" and not have intercourse till after we were married but she wanted more than oral and getting fingered lol. Every time we did it I never asked for it, but she knew I wanted it. Her parents had a covered bench swing that we would frequent after swimming in her pool. Once after an evening swim we were on the swing, me sitting, her laying on her side with her head on my chest. Of course my hands found their way into her one piece swimsuit. I began rubbing her smooth slit until I could feel not the wetness from water but wetness from pussy. As I was doing that she had reached into my shorts and began stroking me and I was rock hard after a second. She tugged my shorts down enough to spring me free and started going down on me. As I fingered her pussy I began sliding my wet fingers back to her ass, pressing my finger up agains her hole but not entering all the way.

[alexossale]

Sorry I posted before I finished
After she is good and wet she stands up and pulls aside he swimsuit, showing me her pale little ass. She grabs my dick and slides it between her cheeks, guiding it to her tight little hole. Once there she begins to sit down on me. She slowly starts to wiggle herself down my shaft, every once in a while I would spread her ass to help her on her way down. Once she was all the way down she started slowly moving up and down on me, her tight ass gripping me. I had to stop her a few times telling her "I need a second....if you move, you're getting an ass full of cum". She listened then resumed with even more enthusiasm moving faster and harder, reaching back spreading her cheeks wide. She must have sensed it coming, she pulled me out just as I came all over our towels. After we composed ourselves, we headed inside. She went into the bathroom to change out of her swimsuit. I went in after her and I saw her suit hanging up and the crotch looked like someone covered it in honey

[captaintrips]

I'm sorry to report that my first Anal experience was not nearly as pleasant or rewarding. This was around 40 years ago now.

I was living with my GF and being in our early 20's, we fucked every spare moment we had. One Sunday morning I've got her in a doggy style and am banging away for all its worth when, you guessed it, I came out, slipped a couple of centimetres higher and went back in at full throttle. It was a genuine accident your honour! But my girl screamed like a stuck pig, which in a way she was, and launched herself forward and off the bed like an Exocet missile looking for a British destroyer.

I was working as a techie in a theatre at the time and was then subjected to a homophobic (that word didn't exist then) tirade about how I had been "infected" by "my gay actor friends". Things were never quite the same again and about two week later she came back from a party to tell me she was moving out and moving in with a guy she had met who was definitely not "queer".

I can't say that I was too devastated by that as she one of my GFs who had nice tits and pussy but no brain.

But it was thirty years or so before I had my next anal experience which was planned and much more enjoyable.

[PuffyNips]

My first time doing anal on a girl almost didn't happen... because of me.

I was in college. I had a steady girlfriend. We fucked often. There was this one evening where I was laying on her bed. She was on top facing towards my feet and bobbing up and down on my cock. Every minute or so she'd ride up too high and my cock would slip out. She'd reach her hand back and reinsert me back into her pussy.

But then on one errant thrust, she reached back and positioned my cock on her asshole. She started to slowly lower herself onto me. It took like 30 seconds for me to realize what was happening. And you know what I did?

I said, "Wait, stop, I'm going in the wrong hole." I squirmed and wrench my cock free from her anus. I was thinking good thing I noticed and managed to pull out before it went in too far....

Yes, I was that dumb and naive!

She used her hand again and stuck me back inside her ass.

I said, "No, that's the wrong hole again..."

She turned her head back towards me and said, "It's okay. I want it there..."

Lightbulb. Oh. She wants it there. Oh. She wants to try anal. Oh. And I almost stopped her. Oh. I'm an idiot.

[gbdick]

We got married and soon were fucking like rabbits. We were constantly trying new things so one day she got on the bed with her ass up and had a tube of lube in her hand and said, "Why don't we try ass fucking?" Wow that was cool. I got on the bed, lubed everything up, and slowly slipped it in. Well, she liked it too. She started cumming hard over and over. It was great. I fucked her ass hard and she loved it. I soon came and filled it up. From then on I fucked her ass at least once a week and every week she had her period. She still likes it. Below are some pictures of her getting fucked in the ass by me. Enjoy

[carameldelight]

My wife and I had only been fucking for maybe a year when she let me fuck her ass the first time. We were fucking like rabbits for that time but it was very vanilla sex; I would lick her and then we would fuck missionary until I came on her belly. One night we were staying in her friend's apartment. We were drinking and having a good time. We were sleeping in the spare bedroom when alcohol mixed with hormones and we were fucking. Her pussy has always been incredibly wet but when alcohol is involved it doubles. After a few pumps her pussy creams down her ass crack and she soaks both of us. On this night I noticed her legs were back a little further than normal and I'm fucking her at a different angle. My cock and balls are soaked and she's making the sheet below us wet with her juices. As we're fucking she starts rotating her hips and I fall out. I didn't think anything about it the first time so I went back into her pussy. We fuck a little while longer and she does the same thing only this time she raises her hips a little. I still don't get the hint so I slide back into her pussy. Almost immediately she wiggles me out again and raises her hips. Now I'm sitting back trying to figure out what she wants. We had never discussed anal sex before, she had never told me she had experience in it and I sure as hell didn't, but here she had wiggled me out of her pussy 3 times. There wasn't any lube anywhere handy so I thought I would see what she would do if I put the head of my dick up against her asshole. I didn't get any response either way so I slowly pushed. I thought I would get slapped or she would jump away but she didn't. I was in shock I was in any girl's ass let alone her's and I didn't want to mess up the moment so I tried to be as gentle as I could going as slow as I could. Once the head popped in she flinched so I stopped and then tried going the slow and steady route some more but she wasn't having any of it. She started to fuck herself on my dick. I got the hint and started fucking her and before long I was balls deep in her ass fucking her for all she was worth.