So this is something that I've honestly never tried...but have thought about it. I'm a straight man interested in doing it with a woman - one that I'd be involved in. Women, what do you like? Do you have to use tons of lubrication? What technique do you prefer? Should I use a condom (not sure how I feel about diving straight in without anything on...) Any advice would be helpful to read...
When it comes to Anal Sex, it matters not whether it's Gay or Straight, with a man or a woman - the mechanics are identical - inserting a penis into an anus. Condom usage is always to be advised, as there is always going to be an element of risk - the evaluation off that risk, though, is a personal thing. Obviously, if your partner is someone who you either know to have sex with others, or if you're unsure of, then the risk is much higher. However, with Anal Sex we are not simply talking about the standard STDs, as there is always the risk of faecally borne bacteria, which is found in all healthy digestive systems, but the risk of tranference & subsequent infection is one that has to be decided for yourself. As for lube - you can never use too much lube, although you will need more if you use a condom than if you choose to go bareback.
you CAN use too much lube, actually. it gets slammed up there and if he's pounding deep, then it creates a "lube enema" situation. also with slightly smaller guys, I wanted more friction. now I use lots of lube (but not too much!) almost got my guy in all the way (but he's really big...)
If it is a monogamous situation and you are sure you are both STD free, I always prefer no condom. Make sure you use enough lube (first on you and then on her). The single use packets are a good guide to go by. As far as how to do it, I always hated it before my current boyfriend. It hurt and felt uncomfortable. I have found that if I am on top to begin with, it makes it much easier. I make him lay there (without thrusting) until I ease it in the whole way. It can be uncomfortable at first, but once he's in it is pleasant. With me being on top, I am able to control the movements and reach orgasm from my clitoris rubbing against him. If the girls tenses up it will be harder and painful, so trying to relax the sphincter muscles is a must. Also, once it is comfortably in, try not to pull it out until you are done. Reinsertion can be painful and uncomfortable.
Another tip for the penetratee - the natural instinctive reaction as soon as you feel anything starting to be inserted is tighten the sphincter, as if trying to stop a bowel movement. In reality, you should force yourself to do the exact opposite & push as if you are constipated & trying to squeeze one out.
Here is a short tutorial I typed up a while back. It's how *I* learned.. The key to this is to take your time and go slow. You learn how to control your butt and sphincter muscles. You learn how to RELAX THEM and you get used to the feeling of it all. Anal play for beginners Disclaimer: I am NOT a doctor and I do NOT play one on TV. This is the way *I* learned how to discover anal play. As usual care needs to be practiced. GO VERY SLOWLY. First start off with a TRIMMED index finger. You may even want to put on a latex glove first to help make it even smoother. Use KY or the drug store brand of KY and lube the finger well. Place it VERY GENTLY near the anus and lightly circle the hole with the finger. DON'T INSERT YET. Just circle it for a few minutes. After a few minutes without insert, just put the finger over the anus and gently press a bit without entering. Just apply a bit of pressure. Do this over and over a few times and after a few minutes SLOWLY begin to insert JUST THE FINGER *TIP* in about a quarter of an inch then take it out. Do this a few times then go a LITTLE further in. Repeat this until you have you whole finger in. DO NOT FORCE IT, IF HE OR SHE OR YOU SAYS STOP, STOP! Within a week or so of trying this the person should be fairly used to the finger and inserting and pumping it in and out should become easy. Also try moving the finger around while inserted, back & forth,etc. Orgasms ARE VERY VERY INTENSE when you leave your finger or butt plug or dildo in. Soon you will want to try something slightly bigger than your finger. Try your middle finger or graduate to a SMALL butt plug. Same rules apply to the new toy as did with the finger. Start off using the finger as usual then after getting loose begin with the plug. Plugs have flared bottoms to prevent them from going all the way in. If you graduate to dildos later get ones with a flared base or ones that have the balls at the bottom. This prevents them from slipping all the way in. You don't need a trip to the ER to retrieve it, that would SUCK! After a while you will become very used to anal play and you won't need much time to prep for your session. You'll loosen up very quickly after you learn how to relax your anal muscles. It takes me less than 5 minutes to go from start to riding a 8 inch silicon dildo like a bucking bronco! GITTYUP LITTLE DOGGIE! The key to learning anal play/sex is to TAKE YOUR TIME.
Congratulations tommyhot ! That is the most in depth pre anal play advise I have ever read on here & it's the best information that any virgin to anal play should read. Well done! I can't imagine what damage / pain someone would go thru if they just forced a large dildo in if no lube was used first?