Dan and Jennifer answer a question from a man whose girlfriend wants to peg him with a strap-on. If his girlfriend had read my post Bend Over Boyfriend: How to Make HIM Want Anal Sex,  he wouldn’t be writing Dan and Jennifer for advice.

Porn stars Darryl Hanah and Lana give detailed tips on anal, squirting, and lube.

For many people, anal sex is the ultimate taboo. Many people are attracted to it precisely because it’s so taboo and mysterious. Others haven’t tried it yet and are curious.

What Is Anal Sex?
Anal sex is the act of placing a finger, an erect penis, or object into the anus of another person to give and receive sexual pleasure. Some people also enjoy oral stimulation of the anus, known as analingus or rimming.

Does Anal Sex Hurt?
Anal sex should not hurt. If it hurts, you’re doing it wrong. With enough lubricant and enough patience, it’s entirely possible to enjoy anal sex as a safe and fulfilling part of your sex life. If you follow these 10 Steps to Great First-Time Anal Sex, you can ensure that your first anal sex experience is pleasurable rather than painful. (more…)

Blogger Jessie Whitfield confesses that her boyfriend has such a beautiful butt that she wants to do him with a strap-on, but he’s not so keen on the idea at first. Things might have gone smoother if she had read my post Bend Over Boyfriend: How to Make HIM Want Anal Sex, but she managed to do all right anyway.

My boyfriend’s butt is beautiful. It’s pretty. It’s plump. It fits in the palm of my hand. I can’t keep my hands off it, and simply touching it turns me on. I’ve spanked it, kissed it, rubbed it, grabbed it, bit it — and now I want to stick something in it.  A strap-on dildo to be exact. I want to bend that boy over, face down, bum up, and do him in the most dirty of ways. I want to make his prostate gland giddy with anal afternoon delight.

So last November I said to him, “I want to do you in the butt with a strap-on. I think it’s only fair.” He’s not only put his peen in my vajayjay, he’s poked me in the tush too.

“Um, no.”  He laughed nervously and changed the subject. Needless to say, this no-bullshit approach did not work. Read more

At The Virginity Project, a husband tell how his wife took his anal virginity. What did it feel like the first time?

I put my arms back and got lost in the music, which was pounding and loud.  The pushing returned but this time I did not resist.  Slowly, slowly, the dildo pressed in and then all of a sudden it just slid forward.

I moaned and gasped, ‘Ohmygod.’

‘Mmmm,’ she said, ‘Here’s some more.’

With that, she pushed in even further.  Another ‘Ohmygod’ from me.  Then the thrusting began.  ‘Keep with me,’ she said.  I did, mimicking what she’d done for me hundreds of times before – bucking my hips in rhythm to meet her thrusts.  I couldn’t believe it. Read more

Anonymous at AlterNet explains why he agreed to be a bend-over boyfriend and what the experience was like. His first time didn’t go that well, but the second…

The first time my girlfriend fucked me in the ass it was with a small purple strap-on dildo that her ex-girlfriend had shipped from Ohio. Like any lady should before taking her man’s anal virginity, my girlfriend took me for a night on the town beforehand. Walking home, after dinner and a long stop at a bar, we decided it was about time I made good on an earlier promise to let her screw me for a change.

Butt sex wasn’t my idea. As far as anal is concerned, I’m not exactly a connoisseur. That goes for giving as well as receiving. Read more

According to a federal study released in 2005, 40 percent of men and 35 percent of women surveyed in 2002 said they have had anal sex with an opposite-sex partner. Given that five of my top ten posts all-time are about anal sex, I’m sure the numbers haveonly  increased since then. That means that  a lot of couples have moved beyond anal sex for beginners and are looking for way to make anal sex even hotter. Here are five advanced anal sex techniques to try. (more…)

NewsMutiny provides today’s insane gentlemen with twelve tips for scoring with women.  I think I’ve met some of the insane gentlemen this article is aimed at, so I just hope they always remember the last tip.

• Offering to buy a woman a drink in a bar is a good first step towards scoring. If she says she’s not thirsty or simply doesn’t drink, try offering her the five bucks you were going to spend on the beverage to come back to your place.
• Most women want to be pursued, so if they run away, by all means go after them. Regardless of what they might scream at you, to others to petition their assistance, or throw in your path to impede your chase, rest assured you are scoring big points by fulfilling a deep-seated subconscious desire.
• Practice makes perfect. Gluing a picture of the object of your desire’s face over an inflatable sex doll will allow you to practice your kissing and intercourse technique so you’ll be sure to impress her when it’s time for the real thing. Read more

In this episode of CherryTV, the women share their tongue techniques – pushing the boundaries of oral sex by teasing the anus. Watch Fellatio & the Backdoor.

Can a penis be too big for anal sex? Probably not, though size does matter. However, a big penis doesn’t have to be a deal breaker. With proper preparation, enough lubrication, the right position, and relaxation techniques, having anal sex with a big penis can be comfortable and pleasurable. (more…)