Ok, me and my girlfriend have been dating since we were 12. We are now 20, and we've had the best relationship ever. We're NEVER got into a big arguement, and everything goes well. We also are good at sex and shit like that. The only thing i dont know stuff about is anal sex. I've ate my girl out, fingered her, first 1 then to 4, shes givin me head, deep throated my cock, gaven me a hand job, i even fisted her once. Anyways, we're pretty much done everything except for anal, and everything we've done before, nothing has EVER went wrong at all. Now, we're going to have anal sex, and i fear that i will screw up majorly, and i DONT want to ruin anything in our relationship.
Anyways, my girl wants anal sex. She's talked about it alot, and she seems to be in it all of a sudden. I sometimes hear her talking to her friends about it, and it seems like her friends really love it. Anyways, about 2 weeks after, me and my girl has tried some playing around. I washed my hands, she was well relaxed, and everything was set. So anyway, after she gave me head and such, i started to finger her with 2 fingers. It then came up to 4. For some reason, my girl LOVES it when i put 4 fingers in her, she loves it to damn much. Anyways, she then told me to stick a finger in her ass. My fingers werent that lubed, and at the time we didnt have any lube either. So she took my hand, and started to lick, suck, and spit on my 4 fingers until it was completely lubed. I didnt mind it at all, but i wanna know something, is it bad if she did that to my fingers? Is there anything wrong with it? I just didnt seem right lickin my own fingers, so she did it for me, and she liked it, is that ok?
Anyways, i started to pet her ass hole, and i started to go in circles on it. It was completely soaked, and then i slowly inserted a finger up her ass nice and slow. It was going slow, and i was kissing her, rubbing her, giving her eye contact and everything. She seemed to be moaning and she told me to go deeper. Soon, my whole finger was in her ass, and she told me to keep it in there cause she said it felt way to good. I kept it in for about 2 minutes, and while in it, i wiggled my finger ALOT. I then began to stroke and stroke nice and slow and she seemed to like it alot. She then told me to stick 2 fingers, and well, i did. I kept on going nice and slow. I did it until it was totally deep and all the way in. She loved it. But then, since it was her first time, she started to bleed. She didnt say anything, and she didnt want me to stop. When she saw the blood on my finger, she had no sign of pain, and she told me to keep going. Anyways, it was pretty cool. It seems weird havin fingers up a girls ass, and it feels like jello once its up there. 
So anyways, i kept on doing it until i heard her parents car door shut. We knew they were home and i didnt want them to see neither did she. I quickly pulled my finger out, washed it with soap, and it was all good. But since i did this so fast, i dont know what really happened to my finger and such. So i got a few questions.
1: Does it reek when you finger a girl up the anal? Does it smell bad at all? Some say yes, some say no, but i dunno, does it smell bad?
2:Do you get any waste on your fingers when your finished? We did it around half an hour after she finished using the bathroom, and she seemed pretty clean, but i dunno, it was right after she used the bathroom. So yea, some peepz say it can happen and u can get some on you, but is it true?
3:Was i doing it correctly? And is it ok to let her suck my fingers? Also, she wants me to stuck 3, and then 4 fingers up her ass next week, and then my cock. Should i stick 4 fingers up there and is it clean? Thanks peepz.
Blue Finger, welcome to the strange and wonderful world of anal play.
I read your post and thought it was great! You are fortunate to have a woman in your life who likes to experiment in bed and isn't shy or afraid to ask you for something new.
Your technique isn't bad. But let me broaden the scope of your vision. In my experience anal play can be great but it really is best combined with fingering or eating her pussy.
Try this out next time:
1) Start off slowly. Foreplay is key, as we've all read in here. Kiss her, tease her, play with her breasts, etc. Good advice is posted all over the board.
2) When you're fingering her, straddle her waist with your upper body, facing her feet. She should be on her back. Be sure to prop yourself up on our elbow. Your weight, unchecked, on her body is uncomforatble.
3) Don't just play with her pussy. Explore it! Yes, it sounds like you know one another very well, but relive the initial exploration. Gently explore every lucious fold of her pussy and begin to play with her clit. You know what I'm talking about, so I won't even go there.
4) With the arm that is straddling her... take your hand and gently spread the cheeks of her ass. Gently move your fingers up and down the crack of her ass cheeks... do not go straight for her anus. Get a good lubricant (tip: If you want to stay away from lubricants like KY or sex shop lubricants, I have found the Aloe Vera Gel works great! Banana Boat sells a huge bottle with a nozzle dispenser. Do not buy the medicated gel - it might sting.) Put a generous amount on your index and ring finger... then begin massaging the crack of her ass again, this time, hesistating over the anus and applying a bit of pressure. DO NOT stop playing with her clitoris with your other hand.
5) Put more lubricant on your index finger and slowly begin to insert is into her anus. Move in and out at first, not going deep at all. TAKE YOUR TIME! This will help relax her sphincter muscle. Apply more lubircant and go a little deeper. Repeat. Continue until you have pushed your finger into her anus as far as it will go. Continue to move in and out, slowly... unless she is really into it and then you can pick up the pace. DO NOT BANG AWAY.
6) Your lady seems to like multiple fingers... after her sphincter is relaxed, relube you ring and index finger and go for two. Go slow.
7) Now, if your lady has reacted like mine reacts, it's time to try something new. While you continue to play with her ass, take you other hand, grabs hers, squeeze a lot of lubricant into her plam and then guide her hand to lubricate your penis. By now, she will get an idea of where you're going. If she's against it, do not insist. If she says nothing, you shouldn't either.
8) Go back to playing with her clit and anus for a few minutes. Then, pull back, get off of her, and slide either next to her or under her. Apply more lubricant to your penis, especially the head. Then press it up against her anus. If she hasn't said "no way" then you're going to have fun trying something new. GENTLY push your penis against her anus, moving your hips back and forth slowly. Be patient. Her sphincter muscle will give. Continue, slowly. The anus is much more delicate when it comes to penetration than the vagina. If you are going to do this, I stress the going slowly part. Even after you have fully penetrated her.
9) Do not stop playing with her clit. Reach over and please her. Do not stop doing this.
In my experience, this leads to a different (pychologically-speaking) orgasm. My wife has said that when she reaches orgasm this way they are much deeper and last longer. Of course, I can only speak from my own experience. This might not apply in your case or that of others.
For a fun twist, while you are still just starting to explore her anus or have begun finger her anus, bend your head down and go down on her. This drives my wife up the walls.
Good luck exploring this new world.
aight, thanks alot for your help man. And yea, we're gonna be starting it again next week.
Nothing wrong with licking/sucking fingers. After all, shes had her mouth around you're penis, so whats wrong with doing it to a finger?
Your questions then...
1. If you stick your finger under your nose, then yeah going to smell some after you've done anal fingering. Not enough though that you're going to be smelling it across the room or anything.
2. Yes, its my experience that you can occaisionally get some on you. But your finger is already coated with bacteria and all the other "nasty" stuff thats in their anus, so its just a matter of having enough on it to be visible. Even if you do get some on you it wouldn't really bother me that much.
3. Sounds like you pretty much did ok. The only thing that would concern me is her bleeding. I'd go slow and use a LOT of lube (real lube- not spit) before I moved into the 3-4 fingers in her. And if she does start bleeding again you should probably stop. Even if she is enjoying it the pleasure could be overriding pain from it. You really don't want to tear something back there. Other than that, just remember not to put your fingers in her vagina once they've been in her anus- theres bacteria in there that can cause infections. Once you do move to actual anal sex, you should probably wear a condom for the same reason.