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One of my sex partners is interested in trying anal. I have made attempts with a few other men in the past two years but never went through with it; the furthest I've ever went was halfway penetration since I always feel a sting, and at times pain, after slight penetration.

However, I would really like to try anal since he suggested having a threesome, which has always been one of my sexual fantasies. In the past two or three times we've had sex, he has started fingering my ass and besides the initial unease, it actually felt pretty pleasurable.

I was wondering how I can start preparing myself for anal sex (he's black and very well-hung) without hurting myself in the process. Please help, thank you! (:

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Use lots of lube and take it slow.
Use 1 finger, then 2, then just the head of the penis, then half, then all.
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Try having a couple of drinks first and always take an enema earlier that morning and yes lube lube lube always use a water based lube and tell him to go SLOW....enjoy.
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Anal sex can be very enjoyable. The first thing that should be done is comunicating when to stop and when to go. The second thing to do is make your anus "experienced" with a penis sized sex toy. Third is finding the appropiate lubrication for the both of you. You will learn this as you self experiment with using and dildo/vibrator to "masturbate." You can do this on your own or you can invite your mate to be an observer. The first time you use a dildo/vibrator use lots of lubrication on your anus and inside you anus. Also use lubricant on the sex toy. Since the dildo/vibrator has a vibrator selection, use the vibration to relax your anus and perinium: the area between your vagina and anus. When you are prepared to insert the sex toy, push down with the same muscles you use for deficating; this causes the anus to open slightly. If you are concerned with fecal matter give yourself a Fleet enema about 1-2 hours prior to anal sex. As you become more experienced with relaxing the anal tissue to allow insertion of a dildo/vibrator, you will become more comfortable with anal sex. In order to have your bf engaged and understanding you may include him in any of you practice sessions. Most important, do not use anything that "deadens" the anal tissue like analeze. Pain and discomfort are your best communication from you body to slow down or stop. Good luck.
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my girlfriend is tiny .. im rather large in the genital area.. she lets me go anal but really slow .. like playing for 30 minutes or so.. for me my precum gets her so hott she opens up nicely .. the best advice is take it extremely slow .. men can tend to rush things .. just think of her first :)
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Preparation: -Cleaning out- before any anal sex or dildoing you should clean out to avoid irritation to the area from rubbing-in fecal matter while stroking. Obviously one would prefer to avoid the embarrassment of soiling and odor as well. Enema must be done in a particular way that differs from the instructions on the Fleet's box or water bottle packaging; those applications are meant to remedy constipation and get things moving from higher up in the gut and aren't concerned with cleanliness in the lower colon/rectum. Most Important: do NOT take the enema lying down or bent over or with the body in any position but upright. This will cause fecal matter from higher in the colon to be rinsed down into the rectum only adding to your problems. Make sure the enema is warm, approx body temp, and take the enema standing up. Take in as much water as it takes to begin to feel full. If using a squeeze-type enema bottle, take care not to let a lot of air into the bottle as this will induce industrial-sized farting... or maybe you're into that... whatever. Then, holding the water in, jump up and down gently and do a few pelvic thrusts, still in the upright position. Then sit on the toilet and release the water/feces. To make sure youre thoroughly emptied, lube with a little Vaseline (protects anal/rectal lining against irritation) and finger your ass with your middle finger as vigorously and deeply as possible for several seconds. This will cause the gut to spasm slightly and force out more of the water/feces. Don't be afraid to touch it; we'll clean up when we're done. Repeat this process one or two times until the water that rinses out is mostly clean. If you have time, it's best to wait several minutes to an hour to allow the gut to absorb or expel any excess water. Play/Dilation/stretching- simply put, the more you do anal, the easier it gets. It's different from first time vaginal because it isn't instantly better by halfway through the first time. You have to want it and you have to work at it. Use plenty of lube. RELAX. Learn to be sexually submissive and trusting and GIVE IN. Don't be afraid to sh*t (if you did the enema right you'll be ok) and push back against penetration like youre trying to poop. Get a dildo. Get a butt-plug. Work with them until they're comfortable and then get a bigger one. Unless youre anatomically abnormal you can handle any human penis in your ass. Once you've done your homework you'll be in for some of the hottest most intense sex you've ever dreamed of.
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analease also can make the guy numb and then your night is put on hold until it wears off!
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How was his being Black even relevant to the query?
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Like everyone said, take it very slow, use lotsa lube and if planned ahead, take an enema. My boyfriend was really incessant about it so when I finally gave in, he listened to me every step of the way. And though it was PAINFUL!, it actually felt really good at some point. You may even notice/feel the largeness of his endowment a little less and enjoy it. 

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I love anal! I never thought I would... it always seemed to be painful. My husband works wonders on my ass! When we have sex I beg him to f**k my ass. Once it is done correct, you will always want it.

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I love anal sex from a girl using a strap-on dildo. Girls are sexy wearing dildos not to mention how it looks up my ass!

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