Losing Your Anal Virginity- Tips for the Newbies


Gay Guys - Tips on Losing Your Anal Virginity

So you wanna play with the big boys, eh? Well don’t worry, everyone is always a little nervous their first time. But the good news is there are plenty of things you can do to make the experience more enjoyable. In fact, you might like it so much you’ll be wondering why it took you so long to bend over and take it in the first place.

Having a good first experience takes more than just lube, a long lasting hard-on, and a patient “top.” It’s always best to prepare yourself.

Trust me. Your first time is going to be the basis of your entire “bottoming” life. If it’s a bad one, it might prevent you from experimenting further down the road. But if it’s good… great balls of fire, you’re in for the time of your life. Yeehaw!

  • Educate Yourself On Proper Hygiene

Since it’s your first time, you won’t know how crucial hygiene maintenance is yet. But trust me, you’ll learn real quick. Make sure you douche properly and take proper care of your eating habits before you put anything inside you, otherwise, you’re in for a rather disgusting discovery.

For a more detailed breakdown on hygiene, read The Do’s and Don’t of Bottoming.

  • Know What You’re Getting Into

It’s never a good idea to grab a penis and shove it inside before knowing how it feels. This will cause SERIOUS cuts or ruptures that will leave your ass throbbing for days.

Practice on yourself first. Buy a dildo or use your fingers, and work the elasticity of your hole to the point of little or no pain. For the next few days, work on lessening the window of pain so when it comes time for the real thing you will have a better idea of your tolerance.

*Note: If you decide to invest in a practice dildo, make sure it’s the size of an average penis (or above). This way, the pain won’t be nearly as much when you are penetrated by a real man.

  • Space It Out

After you’ve practiced on yourself, your ass isn’t going to like you very much. Don’t worry, this is completely normal, your hole was just stretched out for the first time! Give yourself a few days before having sex, otherwise, you will still be sore and it might prevent you from going all in.

  • Choose The Right Guy

This might be easier said than done. You don’t want to have your first time be with some horny toad who doesn’t respect you. These guys will shove it inside and couldn’t care less if it’s painful or not.

Not trusting your “top” will also make you less relaxed, which is one thing you should never be when you’re bottoming. Having someone you can rely on will ease your tension and allow you to be looser.

  • Work Your Way Up

Start by getting him to massage your cheeks, finger you a little, and up the level of foreplay activities. Not only will this get you more relaxed, looser and ready for penetration, but it will also increase your adrenaline and heart rate, creating a much more climactic experience.

*Note: if you’ve practiced beforehand, your tolerance may be higher. But if you haven’t, it may take longer to get over the pain than you had hoped, but be patient. Allow the anus (and anal tube) to loosen up in its own time – it could be 5 to 20 minutes. But once it is, the rest will be a breeze.

  • Don’t Overestimate Lube

Lube is your best friend. Be sure you use plenty before and during. It allows a slicker access for his penis to enter, which ultimately will be less painful for you.

*Note: Use water-based lubricants. They’re smooth and slick, not sticky and messy like silicone or oil-based lubes. Because they’re water-soluble, skin and mucous membranes will absorb them, creating longer lasting lubrication and an easier clean up.

  • Practice With Movements

Your first time with a real man is different than the time you’ve practiced at home because his movements are out of your control. Anal sex must be built on positions that are comfortable for you. Everyone’s pipes are shaped differently. Take this time to get to know yours.

*Note: A simple side-to-side motion may be more comfortable than an in-and-out thrust. Work with what you have and get a feel for what you like. Once you know it, milk it for all its worth.

  • Kiss, Spank, and Rub

Sometimes intimate contact will make us forget the pain. Grab your man’s ass, kiss him, pour your heart into his, and get him to do the same. If done right, the connection you create will replace the pain you may be feeling. And before you know it, you’re begging him to give you more.