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First time Anal

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Rookie Scribe
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I will be giving anal to my lady for the first time. Its first time for us. She is very anxious and apprehensive. Any tips and suggestions to making it pleasurable ?
Lurker
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There are lots of places you can source on the internet for info. Some simple basics... be clean, be empty, use lots of lube, go slow and if she wants you to stop, then stop!
Candyman
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Cyndy has a number of good idea and suggestions. I would add if she has never had a finger there, you take your time preparing and beginning now. Lube - lots and lots of lube, water based - and start with a finger. Progress to two, then a small dildo. Maybe a medium sized dildo, one about the same size as your cock. Allow her to get used to them slowly. By slowly I mean over days and days. Weeks and months if necessary.

I know some ladies enjoy having a small plug they wear for a while, just to get used to the intrusion. That is something else to consider. But whatever you do, do not think you can accomplish this all in one evening. It just doesn't happen like in the stories you read.

If you try this and rush it, she will not only NOT enjoy it, but you will never EVER get a second chance.
"I expect nothing. I fear no one. I am free." Nikos Kazantzakis


Active Ink Slinger
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The primary rule of anal sex is go slow! A butt hole was not digested to be fucked. But with time your girl friend or boyfriend can learn to love it. You can buy some wonderful butt plug sets. You can get them at your favorite adult book store or on line. Butt plugs are soft and designed to go in a butt. The sets consist of four or more butt plugs of various sizes. Start with the smallest first. Now the second rule of anal sex is use lots of lube. You can never use too much. You might to to help her use the plugs a ready for a week. With time, the anal muscle will relax .Also, only put your cock inside her when SHE is ready. With time, she will learn to love it. Anal is great method of birth control.
The romantic bi guy.

Stay horny my friend.
Lurker
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Open mind is the prerequisite. Her ass will open only if her mind does. Take it slow, starting with your tongue and fingers to condition her to the very idea that anal play is pleasurable. Gradually move up to multiple fingers, toys, and eventually your cock depending on how much she is able to accommodate. Be patient, once you do manage to get your cock in her ass for the first time, she may still not be ready for a proper fucking yet. Just let her get accustomed to the feeling and leave it to the next times before you actually start thrusting, proceeding little by little each time. If you don't rush it, it shouldn't take too many more tries from that point until you're able to have wild anal sex with her.
Active Ink Slinger
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Ditto what everyone has said. Based on my experience, and my advice, take your time with her, make sure she is fully aroused and relaxed. Start with your fingers and lots of lube. Stimulate her clit at the same time and it will become easier and the process will be shorter (Me, I like giving oral so I licked her clit). Remember this, it isn't a one time thing where you do it once and she's fully ready every subsequent time, its a process and will likely take several attempts until your successful. However, if you take your time and make sure she's fully aroused, you may find her begging for some backdoor action.