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He tried to put it in, but it just hurt too much. I don't think he used lube, and it's just really tight. Maybe I'd do it again with the right person if I had a lot of trust in him.

Either way, it's not something at the top of my list. My high school sweetheart was raised strictly Catholic and was 'saving it for marriage.

His being exceedingly well-endowed made taking it slowly and using plenty of lube the obvious choice. The oddest thing I noticed was that the initial penetration would generate a tight sensation in my throat, similar to what you might feel after a bad scare.

But it was an exciting feeling, not scary at all. It's a slow but pleasantly luxurious sensation of being gently and benignly pulled inside out.

It certainly was extremely erotic, and I felt aware of my entire body as an erogenous zone. I discovered I was able to orgasm via anal penetration, and anal play is something I enjoy to this day.

At one point in high school, I was having more anal than regular sex. He feels bigger than ever and completely fills you up.

That means lots of lube, starting small with a pinky finger just like in Fifty Shades , then working your way up to small toys or butt plugs.

After that, anal can be amazing! It is super-intense, and your lover has to be extremely delicate and careful and be a good listener and super patient—and you as the receiver have to have a lot of trust in that.

The anus is, after all, an exit, not an entrance, and so it could really, really hurt. This is not an act that should ever be undertaken with a random dude or at a random moment; you both have to want it, and you both have to be prepared.

No assholes allowed in the asshole! I think that's one of the best parts of the whole ordeal. It takes so much time, trust, and communication that it just amplifies everything physical going on because you are so connected with your partner.

Lots of lube, slow, gentle motions, and patience move it quickly to the next phase, which is an exciting, pleasurable pressure. I find that I can have stronger orgasms while being penetrated anally, but these are clitoral or vaginal orgasms, not anal orgasms—those are quite elusive.

For me, it's probably the added stimulation, the intimacy, and the emotional intensity of anal that make orgasms stronger.

But if the angle is wrong in anal sex, with too much of a sharp upward or downward angle, a sting-y and unpleasant pain can be the result.

Having the right angle of entry is important for me. Also, pegging someone with a strap-on can be very pleasurable with an insert-able double-ended dildo, or even just the harness or base of the strap-on grinding up against the clitoris.

Weight Loss. United States. Type keyword s to search. Today's Top Stories. Vegan In-N-Out Burgers. If you've yet to add anal to the menu but are curious to taste test it, there are some things you should know first: Try anal training.

If you're worried about tearing or pain, you can work your way up to full-blown anal by starting with a butt plug, anal beads , or fingers. The biggest challenge, she says, is getting the sphincter to relax enough for something to penetrate it.

Don't stress, it's not unusual for it to take a few tries. Then, slowly lower your booty onto his penis, and adjust to the snug, full feeling.

As you move, having your partner touch your clit or hold a vibrator against it, Mackenzie Riel, relationship and sex expert with sex-toy company Too Timid , tells Health.

This position is one of the most intimate for anal sex—and when paired with a pillow to lift up your hips, one of the most enjoyable, says Sinclair.

Lay back with a small, firm pillow positioned under your hips and then another, softer pillow under your head. Have your partner support his body weight with his hands and enter you slowly.

Once you and your partner have found a rhythm that feels good, reach between your legs to stimulate your clitoris using your fingers or a vibrator.

Your partner is in control, but you can easily communicate with your eyes, voice, or touch that you want him to go faster or slower, or not enter you too deeply or go even deeper.

It's so comfortable, it helps the muscles of the anus relax, she says. Lie on your sides, with you on the inside and your partner curled around you spoon-style.

As you play little spoon, your partner can slowly ease inside you inch by inch. Again, the penetrating partner has most of the control here, but you can back up your booty if you want it deeper or faster.

Your partner can hold you tight and kiss your ears and neck as you adjust to the feel of him, which makes this anal variation so intimate.

But it's also a very orgasmic position, especially since you or your partner can easily reach down and play with your clitoris or nipples.

Use a lot of lube. Use protection. Use a condom, and make sure to use an oil-based lube rather than a water or silicone based one, which can break down latex.

Go slowly. Slower than that. Try different positions. Stop if you feel pain. Enter and withdraw slowly.

Ramming in and yanking out is deeply uncomfortable.

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