15. “Personally, I don’t understand some peoples’ obsession, when there’s a perfectly good vagina right next door. Only a few GFs over my long and varied love life were into it, and for them it was like an occasional naughty treat. On these occasions there’s an extra hotness factor added in mentally. As for the raw physical characteristics of tightness and friction, vaginal is better in the long run. I once had a GF who was down for it any time, and we both got bored of it really quickly TBH. On the other hand, a different GF had done some rotten things and we broke up; while making up months later we were in bed spooning naked when suddenly her ass cheeks then asshole started gobbling my cock like Pac-Man, a one-off event that was hotter than molten tungsten.”
^ Jump up to: a b c Kilchevsky A, Vardi Y, Lowenstein L, Gruenwald I (January 2012). "Is the Female G-Spot Truly a Distinct Anatomic Entity?". The Journal of Sexual Medicine. 9 (3): 719–26. doi:10.1111/j.1743-6109.2011.02623.x. PMID 22240236. Lay summary – G-Spot Does Not Exist, 'Without A Doubt,' Say Researchers - The Huffington Post (19 January 2012).
10. Getting the tip in hurts the most, because the head of the penis is the widest part. Once you're past that and up to the shaft, it'll feel a little better. Remember how much regular sex hurt at first, for some of us? (Unless I guess the guy's shaft is the same width as his head, in which case are you guys gonna break up when he has to go back to Xavier's Academy for Gifted Youngsters?)
“Awkwardness doesn’t mean you’re not close with your partner or in a healthy relationship, it’s because we’re taught from a young age that sex is a taboo topic,” Levkoff says. “Bringing up to a partner a potential thing that you want to try is going to be uncomfortable regardless of what it is. I think that we forget that a part of sexual intimacy means being vulnerable and being able to have those conversations. That’s a human thing. It’s part of being sexually mature.”
The anus was designed to hold in feces. The anus is surrounded with a ring-like muscle, called the anal sphincter, which tightens after we defecate. When the muscle is tight, anal penetration can be painful and difficult. Repetitive anal sex may lead to weakening of the anal sphincter, making it difficult to hold in feces until you can get to the toilet. However, Kegel exercises to strengthen the sphincter may help prevent this problem or correct it.
It can be scary when you're trying something new, especially when it involves a body part you're not use to anyone touching. But try to relax as much as possible, because it will make anal sex better, Pitagora says. "Anoreceptive sex is enhanced by an openness to the experience, trust of the insertive partner, an associated sense of arousal, and the ability to overcome the stereotypical taboo," they once wrote in a paper. Bottom line, do whatever it takes to feel as comfortable as possible, because when you're relaxed you'll enjoy the experience more.

Take things slowly, use plenty of lubrication, and stop if it becomes too painful. Don’t aim to have full penis penetration your first go-round. Try using a finger, and then upgrade to two or three fingers. A toy might be a good option, too, as you grow more comfortable with the sensation. After the first time or two, you and your partner will likely find that the pleasure trumps any initial discomforts.
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