How to Go About Having Anal Sex for the First Time
From a Woman's Point of View
This was written by Misty.. and it would behoove all you guys out there to read it slowly and carefully. If you want your lady to indulge in anal sex with you, then you'd better go about it the right way, the first time, cause if you don't... you probably won't even get a second chance with her. Misty wrote this, in response to a man's question about just how to go about indoctrinating his lady-love into the world of anal sex.
"Anal sex is very rewarding from my point of view, I get some real powerful orgasms from it however there are times I cannot do it because it hurts. There seems no way of knowing until it hurts if it is going to hurt but 90% of the time its ok. I was a girl who never had even had the idea of anal sex when my boyfriend first talked to me about it, and I reluctantly agreed to try it. I don't know how sexual you or how much of this you would be willing to do but this is what happened to me. We talked about it and set a date to try it - the day came around so we went out and got a nice bottle of wine (Mateuse Rose) we drank it and he slowly massaged my entire body from head to toe, then he started kissing my shoulders and continued to seduce me ever so slowly while we kept drinking, this really relaxed me which I did not know at the time. After a while he went down on me and gave me an amazing blow job but stopped just short of giving me an orgasm. After the blow he rolled me over and slowly started kissing the small of my back and then (a complete shock to me) he started kissing my ass, slowly he worked down to my ass hole and started licking it and using his tongue penetrate my butt hole a little, This felt amazing and again almost gave me an orgasm right away. after a few minutes of this, he rolled me over and continued to blow my pussy while using his fingers on my pussy. After about 10 minutes of heaven I noticed he had slipped a finger deep in my ass, but cant tell you when he actually did it as it was just a natural progression and felt like magic. While he fingered my asshole, and sucked on my clit, bringing me to orgasm a couple of times, his cock got rock hard (no shit) then once I was really loose he rolled me over (not bent over but lying on my tummy) and slowly climbed on top of me again, kissing my neck and shoulders, I could feel his cock all hot as it rubbed up against my leg and butt checks and slowly he started to fuck me (in my pussy) still kissing me and getting me to completely relax, then without making any fuss, he drew out of my pussy and just nuzzled his tip of his cock against my asshole, and slowly just poked it against it until it slipped in. He then slowly but very deeply fucked fucked my ass until he dropped a great wad up my asshole. Wow, I am a little wet just writing this now, so forgive me, anyway this is what I suggest you do.
Spend a relaxing night alone, and enjoy the entire night, remember she is dreading this ( I was ) so your job is to relax her. slowly drink wine, or spirits but not beer and just mellow out. Treat her like a goddess, and be patient. Keep a tube of KY jelly handy but out of sight, then fool about, just normal foreplay, then play with her asshole, but don't try to fuck her in the ass right away or you will never get it. Use a little jelly and just try to slip in a finger, not deep to start off with, just a little once you get a finger in your 90 % of the way there, it seems your ass resists but once something has entered it size is not really a problem. Once you get a finger up play about a little, don't try to spread her ass wide, (that all comes months later) just enjoy it, then roll her over and gently fuck her pussy, and after a while once your cock is all slippery take it out and cover it in jelly, thats right even though its already wet, cover it in jelly then just poke slowly if it hurts stop for a little and make her relax again, but if your gentle you will shoot a load up her ass and she should enjoy it. Once you get your cock up her ass, play with her clit with your fingers this kills the pain dead, plus will if done right give her an orgasm.
In the mind if you do it nice the first time and all goes ok, you will get it again, but if you force and hurt her the chances of you getting your cock up there again is next to none.
Take your time over the first few months, each time it will get easier to do it but if she says no just stop and try again another day, never push it.
After about 2 - 3 months of doing this once a week, you will be getting into more forcefully and fun anal sex, try other positions, its great, and the girls I know who like anal sex, really get a taste for it.
Good luck and let me know how you get on."