I love it when he fingers my ass when he is licking my pussy. But his cock feel like it is going to tear my ass apart when we have tried anal. Do you have any experience with this? Is there a good way to get used to having a nice hard cock get int here without hurting me? He doesn't pressure me to do it, I just like to try everything at least once.

That “tear your apart” feeling means it’s not ready for whatever’s been put inside of it hon.  If fingers feel good then we know your ass likes penetration.  I’ve had times where I have had a twinge of discomfort and I make him stop whatever forward movement he’s doing and just breath through it.  It always passes quickly and is replaced by that luscious pressure that drives my clit crazy.  Until your ass is use to taking things regularly here are some general warm up tips:

1. Never attempt anal when you are not feeling perfect relaxed and ready to go down there.  If you are stressed or not feeling clean you will likely tense up as he penetrates you.

2. At least 5 minutes of finger play and in your case perhaps a small dildo in between the size of his fingers and cock.  Think of it as a gradual stretching and warm up of the muscle.  If you don’t stretch it out first it’s not going to work out well for you.  Perhaps he can work in a nice glass plug and then proceed to massage you until you are squirming and ready to go.

3. LUBE…and not pussy lube it’s too thin.  Anal lube is your best friend.  For me…my ass doesn’t like a lot of them…I feel burning as soon as it enters my ass.  So try out some water based and silicone anal lube and see what you like.  If all else fails use Vaseline. Spit doesn’t count as lube and neither does pre-cum.

4.  Try different positions…for the longest time I wanted to be on top and in control of the initial penetration before we’d switch where he was more in control.  Above all have him take his time.  If you experience pain…have him stop and wait a minute before resuming movement.  If you don’t feel the discomfort dissipate quickly you need more prep or lube. Never let a man fuck you if it hurts.  Your ass is made up of delicate tissues that can tear easily…and never use desensitizing lubes!  You can always try playing on your own with a dildo…my ass prefers glass ones…and see if you can get yourself to a point where penetration is comfortable so you know what your body needs to get there.  Bath time is always a good time to relax and experiment :)

Ok I feel pretty dumb with this question but if anywhere was a safe place to ask it would be here! Ok so two nights ago I purchased my very first dildo. I was nervous about the girth but with a little work and patience it slipped in my virgin hole like a dream! After working a bit more I was able to really get to it and fuck myself on it like an old pro, lol. But in the heat of riding my new favorite ride I ... Well how do I put this? I tried to go all the way down on it an I felt like it bottomed out in my ass! Is there a way it can do that? Or do you think it was the quick forceful push I made onto an area that was girthier that my ass wasn't ready for that caused that feeling? Did I really bottom out a mere 7" cock in my ass? All insight you might be able to give me will be appreciated! Thx D

Well darling...here is a diagram of what is going on inside your ass.  Basically  there is a bend where the rectum turns into the colon so depending on how long and jarring the penetration was you may  feel like you bottomed out.  I think the more you fuck yourself the easier your ass will take toys.  Perhaps warm up a little more slowly when feeding the length in before riding it like a pro :)

You show her how pleasurable it can be.  A few tips:

1. Baby steps…don’t bring up the end goal…get her talking about it.  Tell her you really want to explore how pleasurable her ass can be for her. Don’t make it about how badly you want to get inside her tight ass….if she was going to do it for you she would have done it by now.  You need to enlighten her with what she’s been missing out on.  Make it about her not you.   Assure her that you will go so…no penetration until she is ready.

2. Plan a special night where she is aware that you will start exploring her ass.  Don’t expect to just ambush her with assplay.  Chicks need to feel clean and prepared for sex.  If they are worried about odor, cleanliness, etc…be prepared to be shut down.  The key to anything anal is for her to be relaxed.  (If she seems concerned with cleanliness, there are some tips and videos in the link below.)

3. Start with your usual foreplay and some massaging to get her relaxed.  Spend lots of time teasing her pussy using some light touching and rubbing around her asshole.  Her pucker is a bundle of nerves that will drive her crazy.  Get her to flip onto her stomach.  Massage her ass every once and a while spreading her cheeks to hold her ass open for your inspection.  Groan like you’ve just seen the most erotic sight of your life to eliminate any self consciousness.  She will feel vulnerable but oh so naughty to know you are so turned on by the sight.  Continue to rub and tease until she is arching for more.   Place a few kisses on her ass cheeks…even a little nibble…get your hot breath close to her asshole and if she doesn’t shy away…lick.  There really is nothing as delicious as a hot, wet tongue against your asshole.  Finger or rub her clit while you do this and give her a wicked hot orgasm. 

4.  Afterwards talk to her about how she liked it.  Determine is she is happy to keep the assplay at that level or if she is ready for more.  When she is ready to try penetration start with the same prep to get her relaxed and turned on.  Use anal lube and rub a generous amount onto her hole.  Rub it continuously…think of her hole like an elastic…if you work it enough it will loosen and stretch.  Your finger tip should just slip in when it’s ready.  Don’t go any further….it can take a virgin ass a few minutes to fully take a finger.  Just hold it in her ass and work it in really, really slowly.  If you don’t do it right it will hurt.  Game over.  You got one shot to make it good for her so do your home work about assplay. 

5.  Check out my assplay advice page below and learn your stuff…it will pay off in the end.  Better yet…try it on your own ass first so you know first hand what she will be feeling!  Lots of couples explore assplay together…it puts them on a level playing field…you could always suggest that to her.


Good luck hon!  :) xoxoxo